RDX: Difference between revisions

Latest revision as of 15:46, 10 November 2025

Template:Short description Script error: No such module "other uses". Template:Use mdy dates Template:Chembox RDX (Research Department Explosive or Royal Demolition Explosive), or hexogen,^[1] also known by other names, is an organic compound with the formula (CH₂N₂O₂)₃. It is white, odorless, tasteless, and widely used as an explosive.^[2] Chemically, it is classified as a nitroamine alongside HMX, which is a more energetic explosive than TNT. It was used widely in World War II and remains common in military applications. It is lower performing and more toxic than modern replacements such as TKX-50.^[3]

RDX is often used in mixtures with other explosives and plasticizers or phlegmatizers (desensitizers); it is the explosive agent in C-4 plastic explosive and a key ingredient in Semtex. It is stable in storage and is considered one of the most energetic and brisant of the military high explosives,^[4] with a relative effectiveness factor of 1.60.

Name

RDX is also less commonly known as cyclonite, hexogen (particularly in Russian, French and German-influenced languages), T4, and, chemically, as cyclotrimethylene trinitramine.^[5] In the 1930s, the Royal Arsenal, Woolwich, started investigating cyclonite to use against German U-boats that were being built with thicker hulls. The goal was to develop an explosive more energetic than TNT. For security reasons, Britain termed cyclonite "Research Department Explosive" (R.D.X.).^[6] The term RDX appeared in the United States in 1946.^[7] The first public reference in the United Kingdom to the name R.D.X. appeared in 1948; its authors were: the Managing Chemist, ROF Bridgwater; the Chemical Research and Development Department, Woolwich; and the Director of Royal Ordnance Factories, Explosives.^[8]

Usage

Template:More citations needed section

File:Bombing up 106 Squadron Lancaster WWII IWM CH 12541.jpg

Armourers prepare to load Template:Cvt Medium Capacity bombs into the bomb-bay of an Avro Lancaster B Mark III of No. 106 Squadron RAF at RAF Metheringham before a major night raid on Frankfurt. The stencilled lettering around the circumference of each bomb reads "RDX/TNT".

RDX was widely used during World War II, often in explosive mixtures with TNT such as Torpex, Composition B, Cyclotols, and H6. RDX was used in one of the first plastic explosives. The bouncing bomb depth charges used in the "Dambusters Raid" each contained Template:Convert of Torpex;^[9] The Tallboy and Grand Slam bombs designed by Barnes Wallis also used Torpex.

RDX is believed to have been used in many bomb plots, including terrorist plots.

RDX is the base for a number of common military explosives:

Composition A: Granular explosive consisting of RDX and plasticizing wax, such as composition A-3 (91% RDX coated with 9% wax)^[10] and composition A-5 (98.5 to 99.1% RDX coated with 0.95 to 1.54% stearic acid).^[11]
Composition B: Castable mixtures of 59.5% RDX and 39.4% TNT with 1% wax as desensitizer.^[12]
Composition C: The original composition C was used in World War II, but there have been subsequent variations including C-2, C-3, and C-4. C-4 consists of RDX (91%); a plasticizer, dioctyl sebacate (5.3%); and a binder, which is usually polyisobutylene (2.1%); and a specially manufactured mineral oil (1.6%).^[13]
Composition CH-6: 97.5% RDX, 1.5% calcium stearate, 0.5% polyisobutylene, and 0.5% graphite^[14]
DBX (Depth Bomb Explosive): Castable mixture consisting of 21% RDX, 21% ammonium nitrate, 40% TNT, and 18% powdered aluminium, developed during World War II, it was to be used in underwater munitions as a substitute for Torpex employing only half the amount of then-scarce RDX,^[4]^[15] as the supply of RDX became more adequate, however, the mixture was shelved
Cyclotol: Castable mixture of RDX (50–80%) with TNT (20–50%) designated by the amount of RDX/TNT, such as Cyclotol 70/30
HBX: Castable mixtures of RDX, TNT, powdered aluminium, and D-2 wax with calcium chloride
H-6: Castable mixture of RDX, TNT, powdered aluminum, and paraffin wax (used as a phlegmatizing agent)
PBX: RDX is also used as a major component of many polymer-bonded explosives (PBX); RDX-based PBXs typically consist of RDX and at least thirteen different polymer/co-polymer binders.^[16] Examples of RDX-based PBX formulations include, but are not limited to: PBX-9007, PBX-9010, PBX-9205, PBX-9407, PBX-9604, PBXN-106, PBXN-3, PBXN-6, PBXN-10, PBXN-201, PBX-0280, PBX Type I, PBXC-116, PBXAF-108, etc.Script error: No such module "Unsubst".
Semtex (trade name): Plastic demolition explosive containing RDX and PETN as major energetic components ^[17]
Torpex: 42% RDX, 40% TNT, and 18% powdered aluminium; the mixture was designed during World War II and used mainly in underwater ordnance ^[18]

Outside military applications, RDX is also used in controlled demolition to raze structures.^[19] The demolition of the Jamestown Bridge in the U.S. state of Rhode Island was one instance where RDX shaped charges were used to remove the span.^[20]

Synthesis

RDX is classified by chemists as a hexahydro-1,3,5-triazine derivative. In laboratory settings (industrial routes are described below separately) it is obtained by treating hexamine with white fuming nitric acid.^[21]

File:Synthesis hexogen.svg

This nitrolysis reaction also produces methylene dinitrate, ammonium nitrate, and water as by-products. The overall reaction is:^[21]

C₆H₁₂N₄ + 10 HNO₃ → C₃H₆N₆O₆ + 3 CH₂(ONO₂)₂ + NH₄NO₃ + 3 H₂O

The conventional cheap nitration agent, called "mixed acid", cannot be used for RDX synthesis because concentrated sulfuric acid conventionally used to stimulate the nitronium ion formation decomposes hexamine into formaldehyde and ammonia.

Modern syntheses employ hexahydro triacyl triazine as it avoids formation of HMX.^[22]

History

RDX was used by both sides in World War II. The US produced about Template:Convert per month during WWII and Germany about Template:Convert per month.^[23] RDX had the major advantages of possessing greater explosive force than TNT and required no additional raw materials for its manufacture. Thus, it was also extensively used in World War I^[23]

Germany

RDX was reported in 1898 by Georg Friedrich Henning (1863-1945), who obtained a German patent^[24] for its manufacture by nitrolysis of hexamine (hexamethylenetetramine) with concentrated nitric acid.^[25] In this patent, only the medical properties of RDX were mentioned.^[25]

During WWI, Heinrich Brunswig (1865-1946) at the private military-industrial laboratory Template:Ill (Center for Scientific-Technical Research) in Neubabelsberg studied the compound more closely and in June 1916 filed two patent applications, one for its use in smokeless propellants^[26] and another for its use as an explosive, noting its excellent characteristics.^[27]^[28] The German military hadn't considered its adoption during the war due to the expense of production^[29] but started investigating its use in 1920, referring to it as hexogen.^[30]

Research and development findings were not published further until Edmund von Herz,^[31] described as an Austrian and later a German citizen, rediscovered the explosive properties of RDX^[29] and applied for an Austrian patent in 1919, obtaining a British one in 1921^[32] and an American one in 1922.^[33] All patents described the synthesis of the compound by nitrating hexamethylenetetramine.^[32]^[33] The British patent claims included the manufacture of RDX by nitration, its use with or without other explosives, its use as a bursting charge and as an initiator.^[32] The US patent claim was for the use of a hollow explosive device containing RDX and a detonator cap containing it.^[33] Herz was also the first to identify the cyclic nature of the molecule.^[29]

In the 1930s, Germany developed improved production methods.^[30]

During World War II, Germany used the code names W Salt, SH Salt, K-method, the E-method, and the KA-method. These names represented the identities of the developers of the various chemical routes to RDX. The W-method was developed by Wolfram in 1934 and gave RDX the code name "W-Salz". It used sulfamic acid, formaldehyde, and nitric acid.^[34] SH-Salz (SH salt) was from Schnurr, who developed a batch-process in 1937–38 based on nitrolysis of hexamine.^[35] The K-method, from Knöffler, involved addition of ammonium nitrate to the hexamine/nitric acid process.^[36] The E-method, developed by Ebele, proved to be identical to the Ross and Schiessler process described below.^[37] The KA-method, also developed by Knöffler, turned out to be identical to the Bachmann process described below.^[38]

The explosive shells fired by the MK 108 cannon and the warhead of the R4M rocket, both used in Luftwaffe fighter aircraft as offensive armament, both used hexogen as their explosive base.^[39]

UK

In the United Kingdom (UK), RDX was manufactured from 1933 by the research department in a pilot plant at the Royal Arsenal in Woolwich, London, a larger pilot plant being built at the RGPF Waltham Abbey just outside London in 1939.^[40]^[41] In 1939 a twin-unit industrial-scale plant was designed to be installed at a new Template:Convert site, ROF Bridgwater, away from London and production of RDX started at Bridgwater on one unit in August 1941.^[40]^[42] The ROF Bridgwater plant brought in ammonia and methanol as raw materials: the methanol was converted to formaldehyde and some of the ammonia converted to nitric acid, which was concentrated for RDX production.^[8] The rest of the ammonia was reacted with formaldehyde to produce hexamine. The hexamine plant was supplied by Imperial Chemical Industries. It incorporated some features based on data obtained from the United States (US).^[8] RDX was produced by continually adding hexamine and concentrated nitric acid to a cooled mixture of hexamine and nitric acid in the nitrator.^[8] The RDX was purified and processed for its intended use; recovery and reuse of some methanol and nitric acid also was carried out.^[8] The hexamine-nitration and RDX purification plants were duplicated (i.e. twin-unit) to provide some insurance against loss of production due to fire, explosion, or air attack.^[40]

The United Kingdom and British Empire were fighting without allies against Nazi Germany until the middle of 1941 and had to be self-sufficient. At that time (1941), the UK had the capacity to produce Template:Convert (160,000 lb) of RDX per week; both Canada, an allied country and self-governing dominion within the British Empire, and the US were looked upon to supply ammunition and explosives, including RDX.^[43] By 1942, the Royal Air Force's annual requirement was forecast to be Template:Convert of RDX, much of which came from North America (Canada and the US).^[42]

Canada

A different method of production to the Woolwich process was found and used in Canada, possibly at the McGill University department of chemistry. This was based on reacting paraformaldehyde and ammonium nitrate in acetic anhydride.^[44] A UK patent application was made by Robert Walter Schiessler (Pennsylvania State University) and James Hamilton Ross (McGill, Canada) in May 1942; the UK patent was issued in December 1947.^[45] Gilman states that the same method of production had been independently discovered by Ebele in Germany prior to Schiessler and Ross, but that this was not known by the Allies.^[25]^[44] Urbański provides details of five methods of production, and he refers to this method as the (German) E-method.^[37]

UK, US, and Canadian production and development

At the beginning of the 1940s, the major US explosive manufacturers, E. I. du Pont de Nemours & Company and Hercules, had several decades of experience of manufacturing trinitrotoluene (TNT) and had no wish to experiment with new explosives. US Army Ordnance held the same viewpoint and wanted to continue using TNT.^[46] RDX had been tested by Picatinny Arsenal in 1929, and it was regarded as too expensive and too sensitive.^[43] The Navy proposed to continue using ammonium picrate.^[46] In contrast, the National Defense Research Committee (NDRC), who had visited The Royal Arsenal, Woolwich, thought new explosives were necessary.^[46] James B. Conant, chairman of Division B, wished to involve academic research into this area. Conant therefore set up an experimental explosives research laboratory at the Bureau of Mines, Bruceton, Pennsylvania, using Office of Scientific Research and Development (OSRD) funding.^[43]

Woolwich method

In 1941, the UK's Tizard Mission visited the US Army and Navy departments and part of the information handed over included details of the "Woolwich" method of manufacture of RDX and its stabilisation by mixing it with beeswax.^[43] The UK was asking that the US and Canada, combined, supply Template:Convert (440,000 lb) of RDX per day.^[43] A decision was taken by William H. P. Blandy, chief of the Bureau of Ordnance, to adopt RDX for use in mines and torpedoes.^[43] Given the immediate need for RDX, the US Army Ordnance, at Blandy's request, built a plant that copied the equipment and process used at Woolwich. The result was the Wabash River Ordnance Works run by E. I. du Pont de Nemours & Company.^[47] At that time, this works had the largest nitric acid plant in the world.^[43] The Woolwich process was expensive: it needed Template:Convert of strong nitric acid for every pound of RDX produced.^[48]

By early 1941, the NDRC was researching new processes.^[48] The Woolwich or direct nitration process has at least two serious disadvantages: (1) it used large amounts of nitric acid and (2) at least one-half of the formaldehyde is lost. One mole of hexamethylenetetramine could produce at most one mole of RDX.^[49] At least three laboratories with no previous explosive experience were instructed to develop better production methods for RDX; they were based at Cornell, Michigan, and Pennsylvania State universities.^[43]Template:Efn Werner Emmanuel Bachmann, from Michigan, successfully developed the "combination process" by combining the Ross and Schiessler process used in Canada (aka the German E-method) with direct nitration.^[38]^[43] The combination process required large quantities of acetic anhydride instead of nitric acid in the old British "Woolwich process". Ideally, the combination process could produce two moles of RDX from each mole of hexamethylenetetramine.^[49]

The expanded production of RDX could not continue to rely on the use of natural beeswax to desensitize the explosive as in the original British composition (RDX/BWK-91/9). A substitute stabilizer based on petroleum was developed at the Bruceton Explosives Research Laboratory in Pennsylvania, with the resulting explosive designated Composition A-3.^[43]^[50]

Bachmann process

The National Defence Research Committee (NDRC) instructed three companies to develop pilot plants. They were the Western Cartridge Company, E. I. du Pont de Nemours & Company, and Tennessee Eastman Company, part of Eastman Kodak.^[43] At the Eastman Chemical Company (TEC), a leading manufacturer of acetic anhydride, Werner Emmanuel Bachmann developed a continuous-flow process for RDX utilizing an ammonium nitrate/nitric acid mixture as a nitrating agent in a medium of acetic acid and acetic anhydride. RDX was crucial to the war effort and the current batch-production process was too slow. In February 1942, TEC began producing small amounts of RDX at its Wexler Bend pilot plant, which led to the US government authorizing TEC to design and build Holston Ordnance Works (H.O.W.) in June 1942. By April 1943, RDX was being manufactured there.^[51] At the end of 1944, the Holston plant and the Wabash River Ordnance Works, which used the Woolwich process, were producing Template:Convert (50 million pounds) of Composition B per month.^[52]

The Bachmann process yields both RDX and HMX, with the major product determined by the specific reaction conditions.^[53]

Military compositions

The United Kingdom's intention in World War II was to use "desensitised" RDX. In the original Woolwich process, RDX was phlegmatized with beeswax, but later paraffin wax was used, based on the work carried out at Bruceton. In the event the UK was unable to obtain sufficient RDX to meet its needs, some of the shortfall was met by substituting amatol, a mixture of ammonium nitrate and TNT.^[42]

Karl Dönitz was reputed to have claimed that "an aircraft can no more kill a U-boat than a crow can kill a mole".^[54] Nonetheless, by May 1942 Wellington bombers began to deploy depth charges containing Torpex, a mixture of RDX, TNT, and aluminium, which had up to 50 percent more destructive power than TNT-filled depth charges.^[54] Considerable quantities of the RDX–TNT mixture were produced at the Holston Ordnance Works, with Tennessee Eastman developing an automated mixing and cooling process based around the use of stainless steel conveyor belts.^[55]

Terrorism

A Semtex bomb was used in the Pan Am Flight 103 (known also as the Lockerbie) bombing in 1988.^[56] A belt laden with Template:Convert of RDX explosives tucked under the dress of the assassin was used in the assassination of former Indian prime minister Rajiv Gandhi in 1991.^[57] The 1993 Bombay bombings used RDX placed into several vehicles as bombs. RDX was the main component used for the 2006 Mumbai train bombings and the Jaipur bombings in 2008.^[58]^[59] It also is believed to be the explosive used in the 2010 Moscow Metro bombings.^[60]

Traces of RDX were found on pieces of wreckage from 1999 Russian apartment bombings^[61]^[62] and 2004 Russian aircraft bombings.^[63] FSB reports on the bombs used in the 1999 apartment bombings indicated that while RDX was not a part of the main charge, each bomb contained plastic explosive used as a booster charge.^[64]^[65]

Ahmed Ressam, the al-Qaeda Millennium Bomber, used a small quantity of RDX as one of the components in the bomb that he prepared to detonate in Los Angeles International Airport on New Year's Eve 1999–2000; the bomb could have produced a blast forty times greater than that of a devastating car bomb.^[66]^[67]

In July 2012, the Kenyan government arrested two Iranian nationals and charged them with illegal possession of Template:Convert of RDX. According to the Kenyan Police, the Iranians planned to use the RDX for "attacks on Israeli, US, UK and Saudi Arabian targets".^[68]

RDX was used in the assassination of Lebanese Prime Minister Rafic Hariri on February 14, 2005.^[69]

In the 2019 Pulwama attack in India, 250 kg of high-grade RDX was used by Jaish-e-Mohammed. The attack resulted in the deaths of 44 Central Reserve Police Force (CRPF) personnel as well as the attacker.^[70]

Two letter bombs sent to journalists in Ecuador were disguised as USB flash drives which contained RDX that would detonate when plugged in.^[71]

Stability

RDX has a high nitrogen content and a high oxygen to carbon ratio, (O:C ratio), both of which indicate its explosive potential for formation of N₂ and CO₂.

RDX undergoes a deflagration to detonation transition (DDT) in confinement and certain circumstances.^[72]

The velocity of detonation of RDX at a density of 1.80 g/cm³ is 8750 m/s.^[73]Script error: No such module "Unsubst".

It starts to decompose at approximately 170 °C and melts at 204 °C. At room temperature, it is very stable. It burns rather than explodes. It detonates only with a detonator, being unaffected even by small arms fire. This property makes it a useful military explosive. It is less sensitive than pentaerythritol tetranitrate (PETN). Under normal conditions, RDX has a Figure of Insensitivity of exactly 80 (RDX defines the reference point).^[74]Script error: No such module "Unsubst".

RDX sublimes in vacuum, which restricts or prevents its use in some applications.^[75]

RDX, when exploded in air, has about 1.5 times the explosive energy of TNT per unit weight and about 2.0 times per unit volume.^[55]^[76]

RDX is insoluble in water, with solubility 0.05975 g/L at temperature of 25 °C.^[77]

Toxicity

The substance's toxicity has been studied for many years.^[78] RDX has caused convulsions (seizures) in military field personnel ingesting it, and in munition workers inhaling its dust during manufacture. At least one fatality was attributed to RDX toxicity in a European munitions manufacturing plant.^[79]

During the Vietnam War, at least 40 American soldiers were hospitalized with composition C-4 (which is 91% RDX) intoxication from December 1968 to December 1969. C-4 was frequently used by soldiers as a fuel to heat food, and the food was generally mixed by the same knife that was used to cut C-4 into small pieces prior to burning. Soldiers were exposed to C-4 either due to inhaling the fumes, or due to ingestion, made possible by many small particles adhering to the knife having been deposited into the cooked food. The symptom complex involved nausea, vomiting, generalized seizures, and prolonged postictal confusion and amnesia; which indicated toxic encephalopathy.^[80]

Oral toxicity of RDX depends on its physical form; in rats, the LD50 was found to be 100 mg/kg for finely powdered RDX, and 300 mg/kg for coarse, granular RDX.^[79] A case has been reported of a human child hospitalized in status epilepticus following the ingestion of 84.82 mg/kg dose of RDX (or 1.23 g for the patient's body weight of 14.5 kg) in the "plastic explosive" form.^[81]

The substance has low to moderate toxicity with a possible human carcinogen classification.^[82]^[83]^[84] Further research is ongoing, however, and this classification may be revised by the United States Environmental Protection Agency (EPA).^[85]^[86] Remediating RDX-contaminated water supplies has proven to be successful.^[87] It is known to be a kidney toxin in humans and highly toxic to earthworms and plants, thus army testing ranges where RDX was used heavily may need to undergo environmental remediation.^[88] Concerns have been raised by research published in late 2017 indicating that the issue has not been addressed correctly by U.S. officials.^[89]

Civilian use

RDX has been used as a rodenticide because of its toxicity.^[90]

Biodegradation

RDX is degraded by the organisms in sewage sludge as well as the fungus Phanaerocheate chrysosporium.^[91] Both wild and transgenic plants can phytoremediate explosives from soil and water.^[92]^[93] One by-product of the environmental decomposition is R-salt.^[94]

Alternatives

FOX-7 is considered to be approximately a 1-to-1 replacement for RDX in almost all applications.^[95]^[96] TKX-50 is considered to be a high-performance replacement.^[97]

Notes

Template:Notelist

References

Template:Reflist

Bibliography

Template:Refbegin

Script error: No such module "citation/CS1".
Script error: No such module "citation/CS1".
Script error: No such module "citation/CS1".
Script error: No such module "citation/CS1".. See also Template:ISBN.
Urbański translation openlibrary.org, Macmillan, NY, 1964, Template:ISBN.

Template:Refend

External links

Template:Sister project

ADI Limited (Australia). Archive.org leads to Thales group products page that shows some military specifications.
NLM Hazardous Substances Databank (US) – Cyclonite (RDX)
CDC – NIOSH Pocket Guide to Chemical Hazards
nla.gov.au, Army News (Darwin, NT), October 2, 1943, p 3. "Britain's New Explosive: Experts Killed in Terrific Blast", uses "Research Department formula X"
nla.gov.au, The Courier-Mail (Brisbane, Qld.), September 27, 1943, p 1.

Template:Authority control

Template:Convulsants Template:GABA receptor modulators Template:Rodenticides

↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ ^a ^b Cite error: Invalid <ref> tag; no text was provided for refs named Army TM
↑ Cite error: Invalid <ref> tag; no text was provided for refs named Davis
↑ Template:Harvtxt
↑ Script error: No such module "Footnotes".
↑ ^a ^b ^c ^d ^e Cite error: Invalid <ref> tag; no text was provided for refs named sfb
↑ Sweetman, John (2002) The Dambusters Raid. London: Cassell Military Paperbacks. p. 144.
↑ Script error: No such module "Citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "Citation/CS1".
↑ Cite error: Invalid <ref> tag; no text was provided for refs named Hampton
↑ Script error: No such module "citation/CS1". OP 1664 states 21% "aluminum nitrate", but the immediately following text refers to ammonium nitrate.
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ ^a ^b Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ ^a ^b Template:Harvtxt
↑ Cite error: Invalid <ref> tag; no text was provided for refs named Henning
↑ ^a ^b ^c Template:Harvtxt
↑ Template:Cite patent
↑ Template:Cite patent
↑ Script error: No such module "citation/CS1".
↑ ^a ^b ^c Script error: No such module "citation/CS1".
↑ ^a ^b Cite error: Invalid <ref> tag; no text was provided for refs named Gartz
↑ Template:Harvtxt credits "G. C. V. Herz" for the patent, but the patentee is Edmund von Herz.
↑ ^a ^b ^c Cite error: Invalid <ref> tag; no text was provided for refs named Herz-British
↑ ^a ^b ^c Cite error: Invalid <ref> tag; no text was provided for refs named Herz-US
↑ Template:Harvtxt
↑ Template:Harvtxt
↑ Template:Harvtxt
↑ ^a ^b Template:Harvtxt
↑ ^a ^b Template:Harvtxt
↑ Script error: No such module "citation/CS1".Template:Dead link
↑ ^a ^b ^c Cite error: Invalid <ref> tag; no text was provided for refs named cocroft
↑ Cite error: Invalid <ref> tag; no text was provided for refs named Akhavan
↑ ^a ^b ^c Cite error: Invalid <ref> tag; no text was provided for refs named hornby
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Template:Harvtxt
↑ ^a ^b Cite error: Invalid <ref> tag; no text was provided for refs named Gilman
↑ Cite error: Invalid <ref> tag; no text was provided for refs named Schiessler
↑ ^a ^b ^c Template:Harvtxt
↑ Template:Harvtxt
↑ ^a ^b Template:Harvtxt These pages need to be checked. Page 13 may actually be page 18.
↑ ^a ^b Template:Harvtxt
↑ Script error: No such module "citation/CS1".
↑ Cite error: Invalid <ref> tag; no text was provided for refs named Bachmann-Sheehan
↑ Template:Harvtxt
↑ Script error: No such module "citation/CS1".
↑ ^a ^b Template:Harvtxt
↑ ^a ^b Template:Harvtxt
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1"., pages 165-171.
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".Template:Cbignore
↑ Script error: No such module "citation/CS1".Template:Dead link
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "Citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "Citation/CS1".
↑ Template:Harvtxt
↑ Script error: No such module "citation/CS1".
↑ Annotated Reference Outline for the Toxicological Review of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX). U.S. Environmental Protection Agency (November 23, 2010)
↑ ^a ^b Script error: No such module "Citation/CS1".
↑ Script error: No such module "Citation/CS1".
↑ Script error: No such module "Citation/CS1".
↑ Faust, Rosmarie A. (December 1994) Toxicity summary for hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX). Oak Ridge National Laboratory
↑ Script error: No such module "Citation/CS1".
↑ Script error: No such module "Citation/CS1".
↑ Muhly, Robert L. (December 2001) Update on the Reevaluation of the Carcinogenic Potential of RDX. U.S. Army Center for Health Promotion and Preventive Medicine (CHPPM) "white paper"
↑ Script error: No such module "citation/CS1".
↑ Newell, Charles (August 2008). Treatment of RDX & HMX Plumes Using Mulch Biowalls. GSI Environmental, Inc.
↑ Script error: No such module "citation/CS1".
↑ Lustgarten, Abrahm, Canadian Research Adds to Worry Over an Environmental Threat the Pentagon Has Downplayed for Decades, a study released late last year gives environmental experts a way to quantify how much RDX, a chemical used in military explosives, is spreading into surrounding communities, Propublica, January 9, 2018
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "Citation/CS1".
↑ Script error: No such module "Citation/CS1".
↑ Script error: No such module "Citation/CS1".
↑ Script error: No such module "Citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".
↑ Script error: No such module "citation/CS1".

[1] Script error: No such module "citation/CS1".

[2] Script error: No such module "citation/CS1".

[Klapötke1-3] Script error: No such module "citation/CS1".

[Army_TM-4] Cite error: Invalid <ref> tag; no text was provided for refs named Army TM

[Davis-5] Cite error: Invalid <ref> tag; no text was provided for refs named Davis

[MM-18-6] Template:Harvtxt

[7] Script error: No such module "Footnotes".

[sfb-8] Cite error: Invalid <ref> tag; no text was provided for refs named sfb

[9] Sweetman, John (2002) The Dambusters Raid. London: Cassell Military Paperbacks. p. 144.

[10] Script error: No such module "Citation/CS1".

[11] Script error: No such module "citation/CS1".

[12] Script error: No such module "citation/CS1".

[atf-13] Script error: No such module "Citation/CS1".

[Hampton-14] Cite error: Invalid <ref> tag; no text was provided for refs named Hampton

[15] Script error: No such module "citation/CS1". OP 1664 states 21% "aluminum nitrate", but the immediately following text refers to ammonium nitrate.

[16] Script error: No such module "citation/CS1".

[17] Script error: No such module "citation/CS1".

[Ordnance_1947-18] Script error: No such module "citation/CS1".

[Beebe_Pherson_2011-19] Script error: No such module "citation/CS1".

[20] Script error: No such module "citation/CS1".

[ReferenceA-21] Script error: No such module "citation/CS1".

[22] Script error: No such module "citation/CS1".

[Urbanski-78-23] Template:Harvtxt

[Henning-24] Cite error: Invalid <ref> tag; no text was provided for refs named Henning

[urbanski-25] Template:Harvtxt

[26] Template:Cite patent

[27] Template:Cite patent

[28] Script error: No such module "citation/CS1".

[:0-29] Script error: No such module "citation/CS1".

[Gartz-30] Cite error: Invalid <ref> tag; no text was provided for refs named Gartz

[31] Template:Harvtxt credits "G. C. V. Herz" for the patent, but the patentee is Edmund von Herz.

[Herz-British-32] Cite error: Invalid <ref> tag; no text was provided for refs named Herz-British

[Herz-US-33] Cite error: Invalid <ref> tag; no text was provided for refs named Herz-US

[urbanski-W-34] Template:Harvtxt

[urbanski-SH-35] Template:Harvtxt

[urbanski-K-36] Template:Harvtxt

[urbanski-E-37] Template:Harvtxt

[urbanski-KA-38] Template:Harvtxt

[39] Script error: No such module "citation/CS1".Template:Dead link

[cocroft-40] Cite error: Invalid <ref> tag; no text was provided for refs named cocroft

[Akhavan-41] Cite error: Invalid <ref> tag; no text was provided for refs named Akhavan

[hornby-42] Cite error: Invalid <ref> tag; no text was provided for refs named hornby

[baxter-253-259-43] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Template:Harvtxt

[Gilman-44] Cite error: Invalid <ref> tag; no text was provided for refs named Gilman

[Schiessler-45] Cite error: Invalid <ref> tag; no text was provided for refs named Schiessler

[baxter-253-254-46] Template:Harvtxt

[47] Template:Harvtxt

[MM-13-48] Template:Harvtxt These pages need to be checked. Page 13 may actually be page 18.

[Elder-6-49] Template:Harvtxt

[50] Script error: No such module "citation/CS1".

[Bachmann-Sheehan-51] Cite error: Invalid <ref> tag; no text was provided for refs named Bachmann-Sheehan

[52] Template:Harvtxt

[53] Script error: No such module "citation/CS1".

[Baxter-42-54] Template:Harvtxt

[baxter-257&259-55] Template:Harvtxt

[56] Script error: No such module "citation/CS1".

[57] Script error: No such module "citation/CS1".

[58] Script error: No such module "citation/CS1".

[59] Script error: No such module "citation/CS1".

[60] Script error: No such module "citation/CS1".

[61] Script error: No such module "citation/CS1".

[62] Script error: No such module "citation/CS1"., pages 165-171.

[63] Script error: No such module "citation/CS1".

[Mironov-64] Script error: No such module "citation/CS1".

[FSB-65] Script error: No such module "citation/CS1".

[febninth-66] Script error: No such module "citation/CS1".

[comp-67] Script error: No such module "citation/CS1".

[68] Script error: No such module "citation/CS1".

[69] Script error: No such module "citation/CS1".Template:Cbignore

[70] Script error: No such module "citation/CS1".Template:Dead link

[71] Script error: No such module "citation/CS1".

[72] Script error: No such module "Citation/CS1".

[73] Script error: No such module "citation/CS1".

[74] Script error: No such module "citation/CS1".

[75] Script error: No such module "Citation/CS1".

[76] Template:Harvtxt

[77] Script error: No such module "citation/CS1".

[78] Annotated Reference Outline for the Toxicological Review of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX). U.S. Environmental Protection Agency (November 23, 2010)

[Schneider1977-79] Script error: No such module "Citation/CS1".

[80] Script error: No such module "Citation/CS1".

[81] Script error: No such module "Citation/CS1".

[82] Faust, Rosmarie A. (December 1994) Toxicity summary for hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX). Oak Ridge National Laboratory

[83] Script error: No such module "Citation/CS1".

[84] Script error: No such module "Citation/CS1".

[85] Muhly, Robert L. (December 2001) Update on the Reevaluation of the Carcinogenic Potential of RDX. U.S. Army Center for Health Promotion and Preventive Medicine (CHPPM) "white paper"

[86] Script error: No such module "citation/CS1".

[87] Newell, Charles (August 2008). Treatment of RDX & HMX Plumes Using Mulch Biowalls. GSI Environmental, Inc.

[88] Script error: No such module "citation/CS1".

[89] Lustgarten, Abrahm, Canadian Research Adds to Worry Over an Environmental Threat the Pentagon Has Downplayed for Decades, a study released late last year gives environmental experts a way to quantify how much RDX, a chemical used in military explosives, is spreading into surrounding communities, Propublica, January 9, 2018

[Bodeau-90] Script error: No such module "citation/CS1".

[91] Script error: No such module "Citation/CS1".

[92] Script error: No such module "Citation/CS1".

[93] Script error: No such module "Citation/CS1".

[94] Script error: No such module "Citation/CS1".

[95] Script error: No such module "citation/CS1".

[96] Script error: No such module "citation/CS1".

[Klapötke2-97] Script error: No such module "citation/CS1".

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[15]

[16]

[17]

[18]

[19]

[20]

[21]

[22]

[23]

[24]

[25]

[26]

[27]

[28]

[29]

[30]

[31]

[32]

[33]

[34]

[35]

[36]

[37]

[38]

[39]

[40]

[41]

[42]

[43]

[44]

[45]

[46]

[47]

[48]

[49]

[50]

[51]

[52]

[53]

[54]

[55]

[56]

[57]

[58]

[59]

[60]

[61]

[62]

[63]

[64]

[65]

[66]

[67]

[68]

[69]

[70]

[71]

[72]

[73]

[74]

[75]

[76]

[77]

[78]

[79]

[80]

[81]

[82]

[83]

[84]

[85]

[86]

[87]

[88]

[89]

[90]

[91]

[92]

[93]

[94]

[95]

[96]

[97]

@@ Line 73: / Line 73: @@
   }}
 }}
-'''RDX''' ('''Research Department Explosive''' or '''Royal Demolition Explosive''') or '''hexogen''',<ref>{{Cite web|title=RDX explosive|url=https://www.britannica.com/technology/RDX|access-date=2021-09-27|website=britannica.com}}</ref> among other names, is an [[organic compound]] with the formula (CH<sub>2</sub>N<sub>2</sub>O<sub>2</sub>)<sub>3</sub>. It is white, odorless, and tasteless, widely used as an [[explosive]].<ref>{{cite book |last1=Field |first1=Simon Quellen |title=Boom!: The Chemistry and History of Explosives |date=July 1, 2017 |publisher=Chicago Review Press |isbn=978-1613738054 |pages=89–94}}</ref> Chemically, it is classified as a [[nitroamine]] alongside [[HMX]], which is a more energetic explosive than [[trinitrotoluene|TNT]]. It was used widely in [[World War II]] and remains common in [[Military science|military applications]].
+'''RDX''' ('''Research Department Explosive''' or '''Royal Demolition Explosive'''), or '''hexogen''',<ref>{{Cite web|title=RDX explosive|url=https://www.britannica.com/technology/RDX|access-date=2021-09-27|website=britannica.com}}</ref> also known by other names, is an [[organic compound]] with the formula (CH<sub>2</sub>N<sub>2</sub>O<sub>2</sub>)<sub>3</sub>. It is white, odorless, tasteless, and widely used as an [[explosive]].<ref>{{cite book |last1=Field |first1=Simon Quellen |title=Boom!: The Chemistry and History of Explosives |date=July 1, 2017 |publisher=Chicago Review Press |isbn=978-1613738054 |pages=89–94}}</ref> Chemically, it is classified as a [[nitroamine]] alongside [[HMX]], which is a more energetic explosive than [[trinitrotoluene|TNT]]. It was used widely in [[World War II]] and remains common in [[Military science|military applications]].  It is lower performing and more toxic than modern replacements such as [[TKX-50]].<ref name="Klapötke1">{{citation|author=Niko Fischer, Dennis Fischer, Thomas M. Klapötke, Davin G. Piercey, Jörg Stierstorfer |date=2012 |doi=10.1039/C2JM33646D |issue=38 |pages=20418–20422 |periodical=Journal of Materials Chemistry |title=Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate |volume=22}}<!-- auto-translated from German by Module:CS1 translator --></ref>
 RDX is often used in mixtures with other explosives and [[plasticizer]]s or [[phlegmatized|phlegmatizers]] (desensitizers); it is the explosive agent in [[C-4 (explosive)|C-4]] plastic explosive and a key ingredient in [[Semtex]]. It is stable in storage and is considered one of the most energetic and [[brisance|brisant]] of the military [[high explosive]]s,<ref name="Army TM"/> with a [[relative effectiveness factor]] of 1.60.
 ==Name==
-RDX is also less commonly known as '''cyclonite''', hexogen (particularly in Russian, French and German-influenced languages), '''T4''', and, chemically, as '''cyclotrimethylene trinitramine'''.<ref name= Davis/> In the 1930s, the [[Royal Arsenal]], [[Woolwich]], started investigating cyclonite to use against German [[U-boat]]s that were being built with thicker hulls. The goal was to develop an explosive more energetic than [[TNT]]. For security reasons, Britain termed cyclonite "Research Department Explosive" (R.D.X.).<ref name="MM-18">{{Harvtxt|MacDonald and Mack Partnership|1984|p=18}}</ref> The term ''RDX'' appeared in the United States in 1946.<ref>{{Harvnb|Baxter III|1968|pp=27, 42, 255–259}}</ref> The first public reference in the United Kingdom to the name ''R.D.X.'' appeared in 1948; its authors were: the Managing Chemist, [[ROF Bridgwater]]; the Chemical Research and Development Department, Woolwich; and the Director of [[Royal Ordnance Factories]], Explosives.<ref name= sfb/>
+RDX is also less commonly known as '''cyclonite''', '''hexogen''' (particularly in Russian, French and German-influenced languages), '''T4''', and, chemically, as '''cyclotrimethylene trinitramine'''.<ref name= Davis/> In the 1930s, the [[Royal Arsenal]], [[Woolwich]], started investigating cyclonite to use against German [[U-boat]]s that were being built with thicker hulls. The goal was to develop an explosive more energetic than [[TNT]]. For security reasons, Britain termed cyclonite "Research Department Explosive" (R.D.X.).<ref name="MM-18">{{Harvtxt|MacDonald and Mack Partnership|1984|p=18}}</ref> The term ''RDX'' appeared in the United States in 1946.<ref>{{Harvnb|Baxter III|1968|pp=27, 42, 255–259}}</ref> The first public reference in the United Kingdom to the name ''R.D.X.'' appeared in 1948; its authors were: the Managing Chemist, [[ROF Bridgwater]]; the Chemical Research and Development Department, Woolwich; and the Director of [[Royal Ordnance Factories]], Explosives.<ref name= sfb/>
 ==Usage==
@@ Line 88: / Line 88: @@
 RDX is the base for a number of common military explosives:
-*[[Composition A]]: Granular explosive consisting of RDX and plasticizing wax, such as composition A-3 (91% RDX coated with 9% wax)<ref>{{cite journal |last1=Pichtel |first1=John |title=Distribution and Fate of Military Explosives and Propellants in Soil: A Review |journal=Applied and Environmental Soil Science |date=2012 |volume=2012 |issue=Article ID 617236 |page=3 |publisher=Hindawi|doi=10.1155/2012/617236 |doi-access=free }}</ref> and composition A-5 (98.5 to 99.1% RDX coated with 0.95 to 1.54% [[stearic acid]]).<ref>{{cite book |last1=Ritchie |first1=Robert |title=Tech. Report ARLCD-TR-84004, Improving Quality and Performance of Leads Loaded with Composition A-5 |date=March 1984 |publisher=Large Caliber Weapons Systems Laboratory, US Army ARDC |location=Dover, NJ |page=7 |url=http://apps.dtic.mil/dtic/tr/fulltext/u2/a140430.pdf |archive-url=https://web.archive.org/web/20170215004357/http://www.dtic.mil/dtic/tr/fulltext/u2/a140430.pdf |url-status=live |archive-date=February 15, 2017 |access-date=November 9, 2018}}</ref>
+*[[Composition A]]: Granular explosive consisting of RDX and plasticizing wax, such as composition A-3 (91% RDX coated with 9% wax)<ref>{{cite journal |last1=Pichtel |first1=John |title=Distribution and Fate of Military Explosives and Propellants in Soil: A Review |journal=Applied and Environmental Soil Science |date=2012 |volume=2012 |issue=Article ID 617236 |page=3 |publisher=Hindawi|doi=10.1155/2012/617236 |doi-access=free |bibcode=2012ApESS201217236P }}</ref> and composition A-5 (98.5 to 99.1% RDX coated with 0.95 to 1.54% [[stearic acid]]).<ref>{{cite book |last1=Ritchie |first1=Robert |title=Tech. Report ARLCD-TR-84004, Improving Quality and Performance of Leads Loaded with Composition A-5 |date=March 1984 |publisher=Large Caliber Weapons Systems Laboratory, US Army ARDC |location=Dover, NJ |page=7 |url=http://apps.dtic.mil/dtic/tr/fulltext/u2/a140430.pdf |archive-url=https://web.archive.org/web/20170215004357/http://www.dtic.mil/dtic/tr/fulltext/u2/a140430.pdf |url-status=live |archive-date=February 15, 2017 |access-date=November 9, 2018}}</ref>
 *[[Composition B]]: Castable mixtures of 59.5% RDX and 39.4% [[trinitrotoluene|TNT]] with 1% wax as [[desensitizer]].<ref>{{cite web |last1=DOD |title=MIL-C-401E, Composition B, Rev. C |url=http://everyspec.com/MIL-SPECS/MIL-SPECS-MIL-C/MIL-C-401E_45540/ |website=EverySpec |access-date=November 9, 2018 |page=3 |date=March 13, 1974}}</ref>
 *[[Composition C]]: The original composition C was used in World War II, but there have been subsequent variations including C-2, C-3, and [[C-4 (explosive)|C-4]]. C-4 consists of RDX (91%); a plasticizer, [[dioctyl sebacate]] (5.3%); and a binder, which is usually polyisobutylene (2.1%); and a specially manufactured mineral oil (1.6%).<ref name="atf">{{cite journal|last1=Reardon|first1=Michelle R.|last2=Bender|first2=Edward C.|year=2005|title=Differentiation of Composition C4 Based on the Analysis of the Process Oil|journal=Journal of Forensic Sciences|volume=50|issue=3|pages=1–7|doi=10.1520/JFS2004307|url=http://www.astm.org/DIGITAL_LIBRARY/JOURNALS/FORENSIC/PAGES/JFS2004307.htm|publisher=Bureau of Alcohol, Tobacco, Firearms, and Explosives, Forensic Science Laboratory|location=Ammendale, MD|issn=0022-1198|url-access=subscription}}</ref>
@@ Line 110: / Line 110: @@
 The conventional cheap [[nitration]] agent, called "mixed acid", cannot be used for RDX synthesis because concentrated sulfuric acid conventionally used to stimulate the [[nitronium ion]] formation decomposes hexamine into formaldehyde and ammonia.
-Modern syntheses employ [[Hexahydro-1,3,5-triazine|hexahydro triacyl triazine]] as it avoids formation of HMX.<ref>{{cite book |last1=Gilbert |first1=E. E. |last2=Leccacorvi |first2=J. R. |last3=Warman |first3=M. |chapter=23. The Preparation of RDX from 1,3,5-Triacylhexahydro-''s''-triazines |title=Industrial and Laboratory Nitrations |editor1-first=Lyle F. |editor1-last=Albright |editor2-first=Carl |editor2-last=Hanson |series=ACS Symposium Series |volume=22 |pages=327–340 |doi=10.1021/bk-1976-0022.ch023 |date=1 June 1976|isbn=978-0-8412-0306-8 }}</ref>
+Modern syntheses employ hexahydro triacyl triazine as it avoids formation of HMX.<ref>{{cite book |last1=Gilbert |first1=E. E. |last2=Leccacorvi |first2=J. R. |last3=Warman |first3=M. |chapter=23. The Preparation of RDX from 1,3,5-Triacylhexahydro-''s''-triazines |title=Industrial and Laboratory Nitrations |editor1-first=Lyle F. |editor1-last=Albright |editor2-first=Carl |editor2-last=Hanson |series=ACS Symposium Series |volume=22 |pages=327–340 |doi=10.1021/bk-1976-0022.ch023 |date=1 June 1976|isbn=978-0-8412-0306-8 }}</ref>
 ==History==
-RDX was used by both sides in [[World War II]]. The US produced about {{convert|15,000|LT|t}} per month during WWII and Germany about {{convert|7,000|LT|t|order=flip}} per month.<ref name=Urbanski-78>{{Harvtxt|Urbański|1967|p=78}}</ref> RDX had the major advantages of possessing greater explosive force than [[trinitrotoluene|TNT]] and required no additional raw materials for its manufacture. Thus, it was also extensively used in [[World War I]]<ref name=Urbanski-78/>
+RDX was used by both sides in World War II. The US produced about {{convert|15,000|LT|t}} per month during WWII and Germany about {{convert|7,000|LT|t|order=flip}} per month.<ref name=Urbanski-78>{{Harvtxt|Urbański|1967|p=78}}</ref> RDX had the major advantages of possessing greater explosive force than [[trinitrotoluene|TNT]] and required no additional raw materials for its manufacture. Thus, it was also extensively used in [[World War I]]<ref name=Urbanski-78/>
 ===Germany===
-RDX was reported in 1898 by Georg Friedrich Henning (1863-1945), who obtained a [[Germany|German]] [[patent]]<ref name="Henning" /> for its manufacture by [[nitrolysis]] of hexamine ([[hexamethylenetetramine]]) with concentrated nitric acid.<ref name=urbanski>{{Harvtxt|Urbański|1967|pp=77–119}}</ref> In this patent, only the medical properties of RDX were mentioned.<ref name=urbanski/>
+RDX was reported in 1898 by Georg Friedrich Henning (1863-1945), who obtained a [[Germany|German]] [[patent]]<ref name="Henning" /> for its manufacture by nitrolysis of hexamine ([[hexamethylenetetramine]]) with concentrated nitric acid.<ref name=urbanski>{{Harvtxt|Urbański|1967|pp=77–119}}</ref> In this patent, only the medical properties of RDX were mentioned.<ref name=urbanski/>
-During [[World War I|WWI]], Heinrich Brunswig (1865-1946) at the private military-industrial laboratory {{Ill|Zentralstelle für wissenschaftlich-technische Untersuchungen|de}} (Center for Scientific-Technical Research) in [[Neubabelsberg]] studied the compound more closely and in June 1916 filed two patent applications, one for its use in [[smokeless propellant]]s<ref>{{Cite patent|country=DE|number=298539|title=Verfahren zur Herstellung eines Geschoßtreibmittels, das gegen Schlag verhältnismäßig unempfindlich ist|pubdate=1919-09-22|gdate=1916-06-15|assign1=Zentralstelle für wissenschaftlich-technische Untersuchungen GmbH}}</ref> and another for its use as an explosive, noting its excellent characteristics.<ref>{{Cite patent|country=DE|number=299028|title=Verfahren zur Herstellung von Sprengstoffen und Detonationsüberträgern|pubdate=1919-10-15|gdate=1916-06-15|assign1=Zentralstelle für wissenschaftlich-technische Untersuchungen GmbH}}</ref><ref>{{Cite book |last=Gartz |first=Jochen |url=https://books.google.com/books?id=UNogAQAAIAAJ&q=Brunswig |title=Vom griechischen Feuer zum Dynamit: eine Kulturgeschichte der Explosivstoffe |date=2007 |publisher=Mittler |isbn=978-3-8132-0867-2 |pages=153 |language=de}}</ref> The German military hadn't considered its adoption during the war due to the expense of production<ref name=":0">{{Citation |last=Kristensen |first=Tor Erik |title=heksogen |date=2024-03-05 |work=Store norske leksikon |url=https://snl.no/heksogen |access-date=2024-10-31 |language=no}}</ref> but started investigating its use in 1920, referring to it as hexogen.<ref name="Gartz" />
+During WWI, Heinrich Brunswig (1865-1946) at the private military-industrial laboratory {{Ill|Zentralstelle für wissenschaftlich-technische Untersuchungen|de}} (Center for Scientific-Technical Research) in [[Neubabelsberg]] studied the compound more closely and in June 1916 filed two patent applications, one for its use in [[smokeless propellant]]s<ref>{{Cite patent|country=DE|number=298539|title=Verfahren zur Herstellung eines Geschoßtreibmittels, das gegen Schlag verhältnismäßig unempfindlich ist|pubdate=1919-09-22|gdate=1916-06-15|assign1=Zentralstelle für wissenschaftlich-technische Untersuchungen GmbH}}</ref> and another for its use as an explosive, noting its excellent characteristics.<ref>{{Cite patent|country=DE|number=299028|title=Verfahren zur Herstellung von Sprengstoffen und Detonationsüberträgern|pubdate=1919-10-15|gdate=1916-06-15|assign1=Zentralstelle für wissenschaftlich-technische Untersuchungen GmbH}}</ref><ref>{{Cite book |last=Gartz |first=Jochen |url=https://books.google.com/books?id=UNogAQAAIAAJ&q=Brunswig |title=Vom griechischen Feuer zum Dynamit: eine Kulturgeschichte der Explosivstoffe |date=2007 |publisher=Mittler |isbn=978-3-8132-0867-2 |pages=153 |language=de}}</ref> The German military hadn't considered its adoption during the war due to the expense of production<ref name=":0">{{Citation |last=Kristensen |first=Tor Erik |title=heksogen |date=2024-03-05 |work=Store norske leksikon |url=https://snl.no/heksogen |access-date=2024-10-31 |language=no}}</ref> but started investigating its use in 1920, referring to it as hexogen.<ref name="Gartz" />
-Research and development findings were not published further until Edmund von Herz,<ref>{{Harvtxt|Urbański|1967|p=125}} credits "G. C. V. Herz" for the patent, but the patentee is Edmund von Herz.</ref> described as an Austrian and later a German citizen, rediscovered the explosive properties of RDX<ref name=":0" /> and applied for an Austrian patent in 1919, obtaining a British one in 1921<ref name="Herz-British" /><!-- Also FR51577A and CH88759A --> and an American one in 1922.<ref name="Herz-US" /> All patents described the synthesis of the compound by nitrating [[hexamethylenetetramine]].<ref name="Herz-British" /><ref name="Herz-US" /> The British patent claims included the manufacture of RDX by nitration, its use with or without other explosives, its use as a bursting charge and as an initiator.<ref name="Herz-British" /> The US patent claim was for the use of a hollow explosive device containing RDX and a detonator cap containing it.<ref name="Herz-US" /> Herz was also the first to identify the cyclic nature of the molecule.<ref name=":0" />
+Research and development findings were not published further until Edmund von Herz,<ref>{{Harvtxt|Urbański|1967|p=125}} credits "G. C. V. Herz" for the patent, but the patentee is Edmund von Herz.</ref> described as an Austrian and later a German citizen, rediscovered the explosive properties of RDX<ref name=":0" /> and applied for an Austrian patent in 1919, obtaining a British one in 1921<ref name="Herz-British" /><!-- Also FR51577A and CH88759A --> and an American one in 1922.<ref name="Herz-US" /> All patents described the synthesis of the compound by nitrating hexamethylenetetramine.<ref name="Herz-British" /><ref name="Herz-US" /> The British patent claims included the manufacture of RDX by nitration, its use with or without other explosives, its use as a bursting charge and as an initiator.<ref name="Herz-British" /> The US patent claim was for the use of a hollow explosive device containing RDX and a detonator cap containing it.<ref name="Herz-US" /> Herz was also the first to identify the cyclic nature of the molecule.<ref name=":0" />
 In the 1930s, Germany developed improved production methods.<ref name="Gartz" />
-During World War II, Germany used the code names W Salt, SH Salt, K-method, the E-method, and the KA-method. These names represented the identities of the developers of the various chemical routes to RDX. The W-method was developed by Wolfram in 1934 and gave RDX the code name "W-Salz". It used [[sulfamic acid]], formaldehyde, and nitric acid.<ref name="urbanski-W">{{Harvtxt|Urbański|1967|pp=107–109}}</ref> SH-Salz (SH salt) was from Schnurr, who developed a batch-process in 1937–38 based on nitrolysis of hexamine.<ref name="urbanski-SH">{{Harvtxt|Urbański|1967|pp=104–105}}</ref> The K-method, from Knöffler, involved addition of [[ammonium nitrate]] to the hexamine/nitric acid process.<ref name="urbanski-K">{{Harvtxt|Urbański|1967|pp=105–107}}</ref> The E-method, developed by Ebele, proved to be identical to the Ross and Schiessler process described below.<ref name="urbanski-E">{{Harvtxt|Urbański|1967|pp=109–110}}</ref> The KA-method, also developed by Knöffler, turned out to be identical to the Bachmann process described below.<ref name="urbanski-KA">{{Harvtxt|Urbański|1967|pp=111–113}}</ref>
+During World War II, Germany used the code names W Salt, SH Salt, K-method, the E-method, and the KA-method. These names represented the identities of the developers of the various chemical routes to RDX. The W-method was developed by Wolfram in 1934 and gave RDX the code name "W-Salz". It used [[sulfamic acid]], formaldehyde, and nitric acid.<ref name="urbanski-W">{{Harvtxt|Urbański|1967|pp=107–109}}</ref> SH-Salz (SH salt) was from Schnurr, who developed a batch-process in 1937–38 based on nitrolysis of hexamine.<ref name="urbanski-SH">{{Harvtxt|Urbański|1967|pp=104–105}}</ref> The K-method, from Knöffler, involved addition of ammonium nitrate to the hexamine/nitric acid process.<ref name="urbanski-K">{{Harvtxt|Urbański|1967|pp=105–107}}</ref> The E-method, developed by Ebele, proved to be identical to the Ross and Schiessler process described below.<ref name="urbanski-E">{{Harvtxt|Urbański|1967|pp=109–110}}</ref> The KA-method, also developed by Knöffler, turned out to be identical to the Bachmann process described below.<ref name="urbanski-KA">{{Harvtxt|Urbański|1967|pp=111–113}}</ref>
 The explosive shells fired by the [[MK 108 cannon]] and the warhead of the [[R4M rocket]], both used in [[Luftwaffe]] fighter aircraft as offensive armament, both used hexogen as their explosive base.<ref>{{Cite book|url=https://books.google.com/books?id=YMY9DwAAQBAJ&pg=PT17|title=World War 2 In Review No. 23: Boeing B-17 Flying Fortress|last=Press|first=Merriam|publisher=Lulu Press|year=2017|isbn=9781387322572|pages=17}}{{Dead link|date=August 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
 ===UK===
-In the [[United Kingdom]] (UK), RDX was manufactured from 1933 by the research department in a pilot plant at the Royal Arsenal in Woolwich, [[London]], a larger pilot plant being built at the [[Waltham Abbey Royal Gunpowder Mills|RGPF Waltham Abbey]] just outside London in 1939.<ref name=cocroft/><ref name=Akhavan/> In 1939 a twin-unit industrial-scale plant was designed to be installed at a new {{convert|700|acre|ha|adj=on}} site, [[ROF Bridgwater]], away from [[London]] and production of RDX started at Bridgwater on one unit in August 1941.<ref name=cocroft/><ref name=hornby/> The ROF Bridgwater plant brought in ammonia and methanol as raw materials: the methanol was converted to formaldehyde and some of the ammonia converted to nitric acid, which was concentrated for RDX production.<ref name=sfb/> The rest of the ammonia was reacted with formaldehyde to produce hexamine. The hexamine plant was supplied by [[Imperial Chemical Industries]]. It incorporated some features based on data obtained from the United States (US).<ref name=sfb/> RDX was produced by continually adding hexamine and concentrated nitric acid to a cooled mixture of hexamine and nitric acid in the nitrator.<ref name=sfb/> The RDX was purified and processed for its intended use; recovery and reuse of some methanol and nitric acid also was carried out.<ref name=sfb/> The hexamine-nitration and RDX purification plants were duplicated (i.e. twin-unit) to provide some insurance against loss of production due to fire, explosion, or air attack.<ref name=cocroft/>
+In the [[United Kingdom]] (UK), RDX was manufactured from 1933 by the research department in a pilot plant at the Royal Arsenal in Woolwich, [[London]], a larger pilot plant being built at the [[Waltham Abbey Royal Gunpowder Mills|RGPF Waltham Abbey]] just outside London in 1939.<ref name=cocroft/><ref name=Akhavan/> In 1939 a twin-unit industrial-scale plant was designed to be installed at a new {{convert|700|acre|ha|adj=on}} site, ROF Bridgwater, away from London and production of RDX started at Bridgwater on one unit in August 1941.<ref name=cocroft/><ref name=hornby/> The ROF Bridgwater plant brought in ammonia and methanol as raw materials: the methanol was converted to formaldehyde and some of the ammonia converted to nitric acid, which was concentrated for RDX production.<ref name=sfb/> The rest of the ammonia was reacted with formaldehyde to produce hexamine. The hexamine plant was supplied by [[Imperial Chemical Industries]]. It incorporated some features based on data obtained from the United States (US).<ref name=sfb/> RDX was produced by continually adding hexamine and concentrated nitric acid to a cooled mixture of hexamine and nitric acid in the nitrator.<ref name=sfb/> The RDX was purified and processed for its intended use; recovery and reuse of some methanol and nitric acid also was carried out.<ref name=sfb/> The hexamine-nitration and RDX purification plants were duplicated (i.e. twin-unit) to provide some insurance against loss of production due to fire, explosion, or air attack.<ref name=cocroft/>
 The United Kingdom and [[British Empire]] were fighting without allies against [[Nazi Germany]] until the middle of 1941 and had to be [[self-sufficient]]. At that time (1941), the UK had the capacity to produce {{convert|70|LT|tonne}} <!-- {{convert|71000|kg|lb}} -->(160,000&nbsp;lb) of RDX per week; both [[Canada]], an allied country and self-governing dominion within the British Empire, and the US were looked upon to supply ammunition and explosives, including RDX.<ref name=baxter-253-259>{{Harvtxt|Baxter III|1968|pp=253–239}}</ref> By 1942, the [[Royal Air Force]]'s annual requirement was forecast to be {{convert|52000|LT|tonne}} of RDX, much of which came from North America (Canada and the US).<ref name=hornby/>
@@ Line 137: / Line 137: @@
 ===UK, US, and Canadian production and development===
-At the beginning of the 1940s, the major US explosive manufacturers, [[duPont|E. I. du Pont de Nemours & Company]] and [[Hercules Inc.|Hercules]], had several decades of experience of manufacturing [[trinitrotoluene]] (TNT) and had no wish to experiment with new explosives. US Army Ordnance held the same viewpoint and wanted to continue using TNT.<ref name=baxter-253-254>{{Harvtxt|Baxter III|1968|pp=253–254}}</ref> RDX had been tested by [[Picatinny Arsenal]] in 1929, and it was regarded as too expensive and too sensitive.<ref name=baxter-253-259/> The Navy proposed to continue using [[ammonium picrate]].<ref name=baxter-253-254/> In contrast, the [[National Defense Research Committee]] (NDRC), who had visited The Royal Arsenal, Woolwich, thought new explosives were necessary.<ref name="baxter-253-254"/> [[James B. Conant]], chairman of Division B, wished to involve academic research into this area. Conant therefore set up an experimental explosives research laboratory at the [[United States Bureau of Mines|Bureau of Mines]], [[Bruceton, Pennsylvania]], using [[Office of Scientific Research and Development]] (OSRD) funding.<ref name=baxter-253-259/>
+At the beginning of the 1940s, the major US explosive manufacturers, [[duPont|E. I. du Pont de Nemours & Company]] and [[Hercules Inc.|Hercules]], had several decades of experience of manufacturing trinitrotoluene (TNT) and had no wish to experiment with new explosives. US Army Ordnance held the same viewpoint and wanted to continue using TNT.<ref name=baxter-253-254>{{Harvtxt|Baxter III|1968|pp=253–254}}</ref> RDX had been tested by [[Picatinny Arsenal]] in 1929, and it was regarded as too expensive and too sensitive.<ref name=baxter-253-259/> The Navy proposed to continue using [[ammonium picrate]].<ref name=baxter-253-254/> In contrast, the [[National Defense Research Committee]] (NDRC), who had visited The Royal Arsenal, Woolwich, thought new explosives were necessary.<ref name="baxter-253-254"/> [[James B. Conant]], chairman of Division B, wished to involve academic research into this area. Conant therefore set up an experimental explosives research laboratory at the [[United States Bureau of Mines|Bureau of Mines]], [[Bruceton, Pennsylvania]], using [[Office of Scientific Research and Development]] (OSRD) funding.<ref name=baxter-253-259/>
 ====Woolwich method====
@@ Line 144: / Line 144: @@
 By early 1941, the NDRC was researching new processes.<ref name="MM-13"/> The Woolwich or direct nitration process has at least two serious disadvantages: (1) it used large amounts of nitric acid and (2) at least one-half of the formaldehyde is lost. One mole of hexamethylenetetramine could produce at most one mole of RDX.<ref name="Elder-6">{{Harvtxt|Elderfield|1960|p=6}}</ref> At least three laboratories with no previous explosive experience were instructed to develop better production methods for RDX; they were based at [[Cornell University|Cornell]], [[University of Michigan|Michigan]], and [[Pennsylvania State University|Pennsylvania State]] universities.<ref name=baxter-253-259/>{{efn|These were not the only laboratories to work on RDX, Gilman's 1953 account of the Ross–Schiessler method was based on unpublished work from laboratories at the Universities of Michigan, Pennsylvania, Cornell, Harvard, Vanderbilt, McGill (Canada), Bristol (UK), Sheffield (UK), Pennsylvania State College, and the UK's research department.}} [[Werner Emmanuel Bachmann]], from Michigan, successfully developed the "combination process" by combining the Ross and Schiessler process used in Canada (aka the German E-method) with direct nitration.<ref name=urbanski-KA/><ref name=baxter-253-259/> The combination process required large quantities of acetic anhydride instead of nitric acid in the old British "Woolwich process". Ideally, the combination process could produce two moles of RDX from each mole of hexamethylenetetramine.<ref name="Elder-6"/>
-The expanded production of RDX could not continue to rely on the use of natural beeswax to desensitize the explosive as in the original British composition (RDX/BWK-91/9). A substitute stabilizer based on petroleum was developed at the [[Bruceton, Pennsylvania|Bruceton]] Explosives Research Laboratory in Pennsylvania, with the resulting explosive designated Composition A-3.<ref name=baxter-253-259/><ref>{{Cite book |last=Rowland |first=Buford |url=https://books.google.com/books?id=EqNZ5hjPOVMC&pg=PA208 |title=U.S. Navy Bureau of Ordnance in World War II |date=1953 |publisher=Bureau of Ordnance, Department of the Navy |language=en}}</ref>
+The expanded production of RDX could not continue to rely on the use of natural beeswax to desensitize the explosive as in the original British composition (RDX/BWK-91/9). A substitute stabilizer based on petroleum was developed at the Bruceton Explosives Research Laboratory in Pennsylvania, with the resulting explosive designated Composition A-3.<ref name=baxter-253-259/><ref>{{Cite book |last=Rowland |first=Buford |url=https://books.google.com/books?id=EqNZ5hjPOVMC&pg=PA208 |title=U.S. Navy Bureau of Ordnance in World War II |date=1953 |publisher=Bureau of Ordnance, Department of the Navy |language=en}}</ref>
 ====Bachmann process====
-The  [[National Defense Research Committee|National Defence Research Committee]]  (NDRC) instructed three companies to develop pilot plants. They were the Western Cartridge Company, E. I. du Pont de Nemours & Company, and [[Eastman Chemical Company|Tennessee Eastman Company]], part of Eastman Kodak.<ref name=baxter-253-259/> At the [[Eastman Chemical Company]] (TEC), a leading manufacturer of acetic anhydride, [[Werner Emmanuel Bachmann]] developed a continuous-flow process for RDX utilizing an ammonium nitrate/nitric acid mixture as a nitrating agent in a medium of acetic acid and acetic anhydride. RDX was crucial to the war effort and the current batch-production process was too slow. In February 1942, TEC began producing small amounts of RDX at its Wexler Bend pilot plant, which led to the US government authorizing TEC to design and build [[Holston Ordnance Works]] (H.O.W.) in June 1942. By April 1943, RDX was being manufactured there.<ref name=Bachmann-Sheehan/> At the end of 1944, the Holston plant and the [[Newport Chemical Depot|Wabash River Ordnance Works]], which used the Woolwich process, were producing {{convert|25000|ST|tonne}} (50 million pounds) of [[Composition B]] per month.<ref>{{Harvtxt|MacDonald and Mack Partnership|1984|p=32}}</ref>
+The National Defence Research Committee (NDRC) instructed three companies to develop pilot plants. They were the Western Cartridge Company, E. I. du Pont de Nemours & Company, and [[Eastman Chemical Company|Tennessee Eastman Company]], part of Eastman Kodak.<ref name=baxter-253-259/> At the Eastman Chemical Company (TEC), a leading manufacturer of acetic anhydride, Werner Emmanuel Bachmann developed a continuous-flow process for RDX utilizing an ammonium nitrate/nitric acid mixture as a nitrating agent in a medium of acetic acid and acetic anhydride. RDX was crucial to the war effort and the current batch-production process was too slow. In February 1942, TEC began producing small amounts of RDX at its Wexler Bend pilot plant, which led to the US government authorizing TEC to design and build [[Holston Ordnance Works]] (H.O.W.) in June 1942. By April 1943, RDX was being manufactured there.<ref name=Bachmann-Sheehan/> At the end of 1944, the Holston plant and the Wabash River Ordnance Works, which used the Woolwich process, were producing {{convert|25000|ST|tonne}} (50 million pounds) of Composition B per month.<ref>{{Harvtxt|MacDonald and Mack Partnership|1984|p=32}}</ref>
 The Bachmann process yields both RDX and [[HMX]], with the major product determined by the specific reaction conditions.<ref>{{cite book |last1=Yinon |first1=Jehuda |title=Toxicity and Metabolism of Explosives |date=30 June 1990 |publisher=CRC Press |isbn=978-1-4398-0529-9 |page=166 |url=https://books.google.com/books?id=BD3c7FN4x5YC |language=en}}</ref>
@@ Line 154: / Line 154: @@
 The United Kingdom's intention in World War II was to use "desensitised" RDX. In the original Woolwich process, RDX was [[phlegmatized]] with beeswax, but later [[paraffin wax]] was used, based on the work carried out at Bruceton. In the event the UK was unable to obtain sufficient RDX to meet its needs, some of the shortfall was met by substituting [[amatol]], a mixture of ammonium nitrate and TNT.<ref name=hornby/>
-[[Karl Dönitz]] was reputed to have claimed that "an aircraft can no more kill a U-boat than a crow can kill a [[Mole (animal)|mole]]".<ref name=Baxter-42>{{Harvtxt|Baxter III|1968|page=42}}</ref> Nonetheless, by May 1942 [[Vickers Wellington|Wellington bombers]] began to deploy [[depth charge]]s containing [[Torpex]], a mixture of RDX, TNT, and aluminium, which had up to 50 percent more destructive power than TNT-filled depth charges.<ref name=Baxter-42/> Considerable quantities of the RDX–TNT mixture were produced at the Holston Ordnance Works, with [[Tennessee Eastman]] developing an automated mixing and cooling process based around the use of stainless steel [[conveyor belt]]s.<ref name="baxter-257&259">{{Harvtxt|Baxter III|1968|pp=257 & 259}}</ref>
+[[Karl Dönitz]] was reputed to have claimed that "an aircraft can no more kill a U-boat than a crow can kill a [[Mole (animal)|mole]]".<ref name=Baxter-42>{{Harvtxt|Baxter III|1968|page=42}}</ref> Nonetheless, by May 1942 [[Vickers Wellington|Wellington bombers]] began to deploy [[depth charge]]s containing Torpex, a mixture of RDX, TNT, and aluminium, which had up to 50 percent more destructive power than TNT-filled depth charges.<ref name=Baxter-42/> Considerable quantities of the RDX–TNT mixture were produced at the Holston Ordnance Works, with [[Tennessee Eastman]] developing an automated mixing and cooling process based around the use of stainless steel [[conveyor belt]]s.<ref name="baxter-257&259">{{Harvtxt|Baxter III|1968|pp=257 & 259}}</ref>
 ===Terrorism===
@@ Line 178: / Line 178: @@
 The [[Explosive velocity|velocity of detonation]] of RDX at a density of 1.80 g/cm<sup>3</sup> is 8750&nbsp;m/s.<ref>{{Cite book |last=Klapötke |first=Thomas M. |title=Chemistry of High-Energy Materials |edition= 2nd |date=2012-05-29 |publisher=De Gruyter |language=en |doi=10.1515/9783110273595 |isbn=978-3-11-027359-5}}</ref>{{page needed|date=January 2025}}
-It starts to decompose at approximately 170&nbsp;°C and melts at 204&nbsp;°C. At [[room temperature]], it is very stable. It burns rather than explodes. It detonates only with a [[detonator]], being unaffected even by [[small arms]] fire. This property makes it a useful military explosive. It is less sensitive than pentaerythritol tetranitrate ([[PETN]]). Under normal conditions, RDX has a [[Figure of Insensitivity]] of exactly 80 (RDX defines the reference point).<ref>{{Cite book |last=Akhavan |first=Jacqueline |title=The Chemistry of Explosives |date=2022-03-07 |publisher=The Royal Society of Chemistry |isbn=978-1-83916-446-0 |language=en |doi=10.1039/9781839168802}}</ref>{{page needed|date=January 2025}}
+It starts to decompose at approximately 170&nbsp;°C and melts at 204&nbsp;°C. At [[room temperature]], it is very stable. It burns rather than explodes. It detonates only with a [[detonator]], being unaffected even by [[small arms]] fire. This property makes it a useful military explosive. It is less sensitive than pentaerythritol tetranitrate ([[PETN]]). Under normal conditions, RDX has a Figure of Insensitivity of exactly 80 (RDX defines the reference point).<ref>{{Cite book |last=Akhavan |first=Jacqueline |title=The Chemistry of Explosives |date=2022-03-07 |publisher=The Royal Society of Chemistry |isbn=978-1-83916-446-0 |language=en |doi=10.1039/9781839168802}}</ref>{{page needed|date=January 2025}}
 RDX [[sublimation (chemistry)|sublimes]] in [[vacuum]], which restricts or prevents its use in some applications.<ref>{{cite journal
@@ Line 205: / Line 205: @@
 ==Toxicity==
-The substance's toxicity has been studied for many years.<ref>[http://www.epa.gov/ncea/iris/pdfs/Litsearch_RDX.pdf Annotated Reference Outline for the Toxicological Review of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX)]. U.S. Environmental Protection Agency (November 23, 2010)</ref> RDX has caused convulsions (seizures) in military field personnel ingesting it, and in [[munition]] workers inhaling its dust during manufacture. At least one fatality was attributed to RDX toxicity in a European munitions manufacturing plant.<ref name="Schneider1977">{{cite journal |doi=10.1016/0041-008X(77)90144-2 |pmid=854927 |title=Toxicology of cyclotrimethylenetrinitramine: Distribution and metabolism in the rat and the miniature swine |journal=Toxicology and Applied Pharmacology |volume=39 |issue=3 |pages=531–41 |date=March 1977 |last1=Schneider |first1=N. R. |last2=Bradley |first2=S. L. |last3=Andersen |first3=M. E. |bibcode=1977ToxAP..39..531S }}</ref>
+The substance's toxicity has been studied for many years.<ref>[https://web.archive.org/web/20120505082445/http://www.epa.gov/ncea/iris/pdfs/Litsearch_RDX.pdf Annotated Reference Outline for the Toxicological Review of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX)]. U.S. Environmental Protection Agency (November 23, 2010)</ref> RDX has caused convulsions (seizures) in military field personnel ingesting it, and in [[munition]] workers inhaling its dust during manufacture. At least one fatality was attributed to RDX toxicity in a European munitions manufacturing plant.<ref name="Schneider1977">{{cite journal |doi=10.1016/0041-008X(77)90144-2 |pmid=854927 |title=Toxicology of cyclotrimethylenetrinitramine: Distribution and metabolism in the rat and the miniature swine |journal=Toxicology and Applied Pharmacology |volume=39 |issue=3 |pages=531–41 |date=March 1977 |last1=Schneider |first1=N. R. |last2=Bradley |first2=S. L. |last3=Andersen |first3=M. E. |bibcode=1977ToxAP..39..531S }}</ref>
 During the [[Vietnam War]], at least 40 American soldiers were hospitalized with [[C-4 (explosive)|composition C-4]] (which is 91% RDX) intoxication from December 1968 to December 1969. C-4 was frequently used by soldiers as a fuel to heat food, and the food was generally mixed by the same knife that was used to cut C-4 into small pieces prior to burning. Soldiers were exposed to C-4 either due to inhaling the fumes, or due to ingestion, made possible by many small particles adhering to the knife having been deposited into the cooked food. The symptom complex involved nausea, vomiting, generalized seizures, and prolonged [[postictal state|postictal confusion]] and amnesia; which indicated [[toxic encephalopathy]].<ref>{{cite journal |last1=Ketel |first1=W. B. |last2=Hughes |first2=J. R. |title=Toxic encephalopathy with seizures secondary to ingestion of composition C-4: A clinical and electroencephalographic study |journal=Neurology |date=1 August 1972 |volume=22 |issue=8 |pages=871–6 |doi=10.1212/WNL.22.8.870 |pmid=4673417 |s2cid=38403787}}</ref>
@@ Line 211: / Line 211: @@
 Oral toxicity of RDX depends on its physical form; in rats, the LD50 was found to be 100&nbsp;mg/kg for finely powdered RDX, and 300&nbsp;mg/kg for coarse, granular RDX.<ref name="Schneider1977" /> A case has been reported of a human child hospitalized in [[status epilepticus]] following the ingestion of 84.82&nbsp;mg/kg dose of RDX (or 1.23 g for the patient's body weight of 14.5&nbsp;kg) in the "plastic explosive" form.<ref>{{cite journal |last1=Woody |first1=R.C. |last2=Kearns |first2=G.L. |last3=Brewster |first3=M.A. |last4=Turley |first4=C.P. |last5=Sharp |first5=G.B. |last6=Lake |first6=R.S. |title=The Neurotoxicity of Cyclotrimethylenetrinitramine (RDX) in a Child: A Clinical and Pharmacokinetic Evaluation |journal=Journal of Toxicology: Clinical Toxicology |date=1986 |volume=24 |issue=4 |pages=305–319 |doi=10.3109/15563658608992595 |pmid=3746987}}</ref>
-The substance has low to moderate toxicity with a [[possible human carcinogen]] classification.<ref>Faust, Rosmarie A. (December 1994) [https://web.archive.org/web/20050411005431/http://cira.ornl.gov/documents/RDX.pdf Toxicity summary for hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX)]. [[Oak Ridge National Laboratory]]</ref><ref>{{cite journal |doi=10.1016/j.chemosphere.2006.12.005 |pmid=17275885 |title=Age dependent acute oral toxicity of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) and two anaerobic ''N''-nitroso metabolites in deer mice (''Peromyscus maniculatus'') |journal=Chemosphere |volume=67 |issue=11 |pages=2267–73 |year=2007 |last1=Smith |first1=Jordan N. |last2=Liu |first2=Jun |last3=Espino |first3=Marina A. |last4=Cobb |first4=George P. |bibcode=2007Chmsp..67.2267S }}</ref><ref>{{cite journal |doi=10.1016/j.mrgentox.2007.01.006 |pmid=17360228 |title=Examination of the mutagenicity of RDX and its ''N''-nitroso metabolites using the ''Salmonella'' reverse mutation assay |journal=Mutation Research/Genetic Toxicology and Environmental Mutagenesis |volume=629 |issue=1 |pages=64–9 |year=2007 |last1=Pan |first1=Xiaoping |last2=San Francisco |first2=Michael J. |last3=Lee |first3=Crystal |last4=Ochoa |first4=Kelly M. |last5=Xu |first5=Xiaozheng |last6=Liu |first6=Jun |last7=Zhang |first7=Baohong |last8=Cox |first8=Stephen B. |last9=Cobb |first9=George P. |bibcode=2007MRGTE.629...64P }}</ref> Further research is ongoing, however, and this classification may be revised by the [[United States Environmental Protection Agency]] (EPA).<ref>Muhly, Robert L. (December 2001) [https://web.archive.org/web/20091112035039/http://www.mass.gov/dep/cleanup/compliance/rdxwhite.pdf Update on the Reevaluation of the Carcinogenic Potential of RDX]. [[U.S. Army Center for Health Promotion and Preventive Medicine]] (CHPPM) "white paper"</ref><ref>{{cite web |title=Hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) (CASRN 121-82-4)|url=http://www.epa.gov/iris/subst/0313.htm|publisher=epa.gov|access-date=January 1, 2014}}</ref> Remediating RDX-contaminated water supplies has proven to be successful.<ref>Newell, Charles (August 2008). [https://web.archive.org/web/20140116190908/http://www.serdp.org/content/download/4725/68763/file/ER-0426-FR.pdf Treatment of RDX & HMX Plumes Using Mulch Biowalls]. GSI Environmental, Inc.</ref> It is known to be a kidney toxin in humans and highly toxic to earthworms and plants, thus army testing ranges where RDX was used heavily may need to undergo environmental remediation.<ref>{{cite book|last1=Klapötke|first1=Thomas M.|title=Chemistry of high-energy materials|date=2012|publisher=De Gruyter|location=Berlin [u.a.]|isbn=978-311027358-8|edition=Second}}</ref> Concerns have been raised by research published in late 2017 indicating that the issue has not been addressed correctly by U.S. officials.<ref>Lustgarten, Abrahm, ''[https://www.propublica.org/article/canadian-research-adds-to-worry-over-an-environmental-threat-the-pentagon-has-downplayed-for-decades Canadian Research Adds to Worry Over an Environmental Threat the Pentagon Has Downplayed for Decades, a study released late last year gives environmental experts a way to quantify how much RDX, a chemical used in military explosives, is spreading into surrounding communities]'', Propublica, January 9, 2018</ref>
+The substance has low to moderate toxicity with a [[possible human carcinogen]] classification.<ref>Faust, Rosmarie A. (December 1994) [https://web.archive.org/web/20050411005431/http://cira.ornl.gov/documents/RDX.pdf Toxicity summary for hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX)]. [[Oak Ridge National Laboratory]]</ref><ref>{{cite journal |doi=10.1016/j.chemosphere.2006.12.005 |pmid=17275885 |title=Age dependent acute oral toxicity of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) and two anaerobic ''N''-nitroso metabolites in deer mice (''Peromyscus maniculatus'') |journal=Chemosphere |volume=67 |issue=11 |pages=2267–73 |year=2007 |last1=Smith |first1=Jordan N. |last2=Liu |first2=Jun |last3=Espino |first3=Marina A. |last4=Cobb |first4=George P. |bibcode=2007Chmsp..67.2267S }}</ref><ref>{{cite journal |doi=10.1016/j.mrgentox.2007.01.006 |pmid=17360228 |title=Examination of the mutagenicity of RDX and its ''N''-nitroso metabolites using the ''Salmonella'' reverse mutation assay |journal=Mutation Research/Genetic Toxicology and Environmental Mutagenesis |volume=629 |issue=1 |pages=64–9 |year=2007 |last1=Pan |first1=Xiaoping |last2=San Francisco |first2=Michael J. |last3=Lee |first3=Crystal |last4=Ochoa |first4=Kelly M. |last5=Xu |first5=Xiaozheng |last6=Liu |first6=Jun |last7=Zhang |first7=Baohong |last8=Cox |first8=Stephen B. |last9=Cobb |first9=George P. |bibcode=2007MRGTE.629...64P }}</ref> Further research is ongoing, however, and this classification may be revised by the [[United States Environmental Protection Agency]] (EPA).<ref>Muhly, Robert L. (December 2001) [https://web.archive.org/web/20091112035039/http://www.mass.gov/dep/cleanup/compliance/rdxwhite.pdf Update on the Reevaluation of the Carcinogenic Potential of RDX]. [[U.S. Army Center for Health Promotion and Preventive Medicine]] (CHPPM) "white paper"</ref><ref>{{cite web |title=Hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) (CASRN 121-82-4)|url=http://www.epa.gov/iris/subst/0313.htm|archive-url=https://web.archive.org/web/20000930012028/http://www.epa.gov/IRIS/subst/0313.htm|url-status=dead|archive-date=September 30, 2000|publisher=epa.gov|access-date=January 1, 2014}}</ref> Remediating RDX-contaminated water supplies has proven to be successful.<ref>Newell, Charles (August 2008). [https://web.archive.org/web/20140116190908/http://www.serdp.org/content/download/4725/68763/file/ER-0426-FR.pdf Treatment of RDX & HMX Plumes Using Mulch Biowalls]. GSI Environmental, Inc.</ref> It is known to be a kidney toxin in humans and highly toxic to earthworms and plants, thus army testing ranges where RDX was used heavily may need to undergo environmental remediation.<ref>{{cite book|last1=Klapötke|first1=Thomas M.|title=Chemistry of high-energy materials|date=2012|publisher=De Gruyter|location=Berlin [u.a.]|isbn=978-311027358-8|edition=Second}}</ref> Concerns have been raised by research published in late 2017 indicating that the issue has not been addressed correctly by U.S. officials.<ref>Lustgarten, Abrahm, ''[https://www.propublica.org/article/canadian-research-adds-to-worry-over-an-environmental-threat-the-pentagon-has-downplayed-for-decades Canadian Research Adds to Worry Over an Environmental Threat the Pentagon Has Downplayed for Decades, a study released late last year gives environmental experts a way to quantify how much RDX, a chemical used in military explosives, is spreading into surrounding communities]'', Propublica, January 9, 2018</ref>
 ==Civilian use==
@@ Line 217: / Line 217: @@
 ==Biodegradation==
-RDX is degraded by the organisms in [[sewage sludge]] as well as the fungus ''[[Phanerochaete|Phanaerocheate chrysosporium]]''.<ref>{{cite journal |year= 2000|journal=Applied Microbiology and Biotechnology|title=Microbial degradation of explosives: biotransformation versus mineralization |last1=Hawari |first1=J. |last2=Beaudet |first2=S. |last3=Halasz |first3=A. |last4=Thiboutot |first4=S. |last5=Ampleman |first5=G. |pages=605–618 |volume=54 |pmid=11131384 |issue=5 |doi=10.1007/s002530000445|s2cid=22362850}}</ref> Both wild and transgenic plants can [[phytoremediation|phytoremediate]] explosives from soil and water.<ref>{{cite journal |title=Phytoremediation of explosives (TNT, RDX, HMX) by wild-type and transgenic plants|date=December 2012|journal=Journal of Environmental Management |last1=Panz |first1=K. |last2=Miksch |first2=K. |pages=85–92|volume=113 |pmid= 22996005 |doi=10.1016/j.jenvman.2012.08.016|bibcode=2012JEnvM.113...85P }}</ref><ref>{{cite journal |doi=10.1016/j.ecoleng.2007.09.005 |title=Treatment of RDX using down-flow constructed wetland mesocosms |journal=Ecological Engineering |volume=32 |issue=1 |pages=72–80 |year=2008 |last1=Low |first1=Darryl |last2=Tan |first2=Kui |last3=Anderson |first3=Todd |last4=Cobb |first4=George P. |last5=Liu |first5=Jun |last6=Jackson |first6=W. Andrew |bibcode=2008EcEng..32...72L }}</ref> One by-product of the environmental decomposition is [[R-salt]].<ref>{{Cite journal |last=Rothstein |first=Sarah A. |last2=Dubé |first2=Pascal |last3=Anderson |first3=Stephen R. |date=2017 |title=An Improved Process Towards Hexahydro-1,3,5-trinitroso-1,3,5-triazine (TNX) |journal=Propellants, Explosives, Pyrotechnics |language=en |volume=42 |issue=2 |pages=126–130 |doi=10.1002/prep.201600149 |issn=1521-4087}}</ref>
+RDX is degraded by the organisms in [[sewage sludge]] as well as the fungus ''[[Phanerochaete|Phanaerocheate chrysosporium]]''.<ref>{{cite journal |year= 2000|journal=Applied Microbiology and Biotechnology|title=Microbial degradation of explosives: biotransformation versus mineralization |last1=Hawari |first1=J. |last2=Beaudet |first2=S. |last3=Halasz |first3=A. |last4=Thiboutot |first4=S. |last5=Ampleman |first5=G. |pages=605–618 |volume=54 |pmid=11131384 |issue=5 |doi=10.1007/s002530000445|s2cid=22362850}}</ref> Both wild and transgenic plants can [[phytoremediation|phytoremediate]] explosives from soil and water.<ref>{{cite journal |title=Phytoremediation of explosives (TNT, RDX, HMX) by wild-type and transgenic plants|date=December 2012|journal=Journal of Environmental Management |last1=Panz |first1=K. |last2=Miksch |first2=K. |pages=85–92|volume=113 |pmid= 22996005 |doi=10.1016/j.jenvman.2012.08.016|bibcode=2012JEnvM.113...85P }}</ref><ref>{{cite journal |doi=10.1016/j.ecoleng.2007.09.005 |title=Treatment of RDX using down-flow constructed wetland mesocosms |journal=Ecological Engineering |volume=32 |issue=1 |pages=72–80 |year=2008 |last1=Low |first1=Darryl |last2=Tan |first2=Kui |last3=Anderson |first3=Todd |last4=Cobb |first4=George P. |last5=Liu |first5=Jun |last6=Jackson |first6=W. Andrew |bibcode=2008EcEng..32...72L }}</ref> One by-product of the environmental decomposition is [[R-salt]].<ref>{{Cite journal |last1=Rothstein |first1=Sarah A. |last2=Dubé |first2=Pascal |last3=Anderson |first3=Stephen R. |date=2017 |title=An Improved Process Towards Hexahydro-1,3,5-trinitroso-1,3,5-triazine (TNX) |journal=Propellants, Explosives, Pyrotechnics |language=en |volume=42 |issue=2 |pages=126–130 |doi=10.1002/prep.201600149 |issn=1521-4087}}</ref>
 ==Alternatives==
-[[FOX-7]] is considered to be approximately a 1-to-1 replacement for RDX in almost all applications.<ref>{{cite web |url = http://apps.dtic.mil/dtic/tr/fulltext/u2/a530896.pdf |title = FOX-7 for Insensitive Boosters Merran A. Daniel, Phil J. Davies and Ian J. Lochert |archive-url=https://web.archive.org/web/20170303024719/http://www.dtic.mil/dtic/tr/fulltext/u2/a530896.pdf |archive-date=3 March 2017 |url-status=live}}</ref><ref>{{cite web |url = http://www.eurenco.com/content/explosives/defence-security/high-explosives/insensitive-explosives/fox-7/ |title = Fox-7 EURENCO ''Indeed, DADNE (FOX-7) has been shown to increase the burning rate in propellants more than RDX does, which is very interesting in high performance propellants.'' |access-date = August 3, 2017 |archive-date = August 4, 2017 |archive-url = https://web.archive.org/web/20170804113029/http://www.eurenco.com/content/explosives/defence-security/high-explosives/insensitive-explosives/fox-7/ |url-status = dead }}</ref>
+[[FOX-7]] is considered to be approximately a 1-to-1 replacement for RDX in almost all applications.<ref>{{cite web |url = http://apps.dtic.mil/dtic/tr/fulltext/u2/a530896.pdf |title = FOX-7 for Insensitive Boosters Merran A. Daniel, Phil J. Davies and Ian J. Lochert |archive-url=https://web.archive.org/web/20170303024719/http://www.dtic.mil/dtic/tr/fulltext/u2/a530896.pdf |archive-date=3 March 2017 |url-status=live}}</ref><ref>{{cite web |url = http://www.eurenco.com/content/explosives/defence-security/high-explosives/insensitive-explosives/fox-7/ |title = Fox-7 EURENCO ''Indeed, DADNE (FOX-7) has been shown to increase the burning rate in propellants more than RDX does, which is very interesting in high performance propellants.'' |access-date = August 3, 2017 |archive-date = August 4, 2017 |archive-url = https://web.archive.org/web/20170804113029/http://www.eurenco.com/content/explosives/defence-security/high-explosives/insensitive-explosives/fox-7/ |url-status = dead }}</ref>  [[TKX-50]] is considered to be a high-performance replacement.<ref name="Klapötke2">{{citation|author=Niko Fischer, Dennis Fischer, Thomas M. Klapötke, Davin G. Piercey, Jörg Stierstorfer |date=2012 |doi=10.1039/C2JM33646D |issue=38 |pages=20418–20422 |periodical=Journal of Materials Chemistry |title=Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate |volume=22}}<!-- auto-translated from German by Module:CS1 translator --></ref>
 ==Notes==
@@ Line 247: / Line 247: @@
 | issue= 5
 | year= 1949
-| doi= 10.1021/ja01173a092}}</ref>
+| doi= 10.1021/ja01173a092| bibcode= 1949JAChS..71.1842B
+}}</ref>
 <ref name= cocroft>{{Citation |first=Wayne D.|last=Cocroft |title=Dangerous Energy: The archaeology of gunpowder and military explosives manufacture |location=Swindon |publisher=[[English Heritage]] |isbn=1-85074-718-0 |year=2000|pages=210–211}}</ref>
@@ Line 475: / Line 476: @@
 | year= 1925
 | doi= 10.1021/ja01688a017
+| bibcode=1925JAChS..47.2754H
 | ref= none}}
 *{{Citation
@@ Line 491: / Line 493: @@
 {{Commons category|RDX}}
 * [https://web.archive.org/web/20081206125325/http://www.adi-limited.com/2-01-050-030-000.html ADI Limited (Australia)]. [https://web.archive.org/web/*/http://www.adi-limited.com/2-01-050-030-000.html Archive.org] leads to [https://web.archive.org/web/20110716214813/http://www.thalesgroup.com/assets/0/95/389/392/e93b97ee-e77e-43fa-8f7c-07d4061bc14d.pdf?LangType=2057 Thales group products page] that shows some military specifications.<!-- The link is borderline. Without the specs, it would just be an ad. EL could be discarded. -->
-* [http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@na+@rel+cyclonite NLM Hazardous Substances Databank (US) – Cyclonite (RDX)]
+* [https://www.nlm.nih.gov/toxnet/index.html NLM Hazardous Substances Databank (US) – Cyclonite (RDX)]
 * [https://www.cdc.gov/niosh/npg/npgd0169.html CDC – NIOSH Pocket Guide to Chemical Hazards]
 * [http://nla.gov.au/nla.news-article38338874 nla.gov.au], Army News (Darwin, NT), October 2, 1943, p 3. "Britain's New Explosive: Experts Killed in Terrific Blast", uses "Research Department formula X"

RDX: Difference between revisions

Latest revision as of 15:46, 10 November 2025

Contents

Name

Usage

Synthesis

History

Germany

UK

Canada

UK, US, and Canadian production and development

Woolwich method

Bachmann process

Military compositions

Terrorism

Stability

Toxicity

Civilian use

Biodegradation

Alternatives

Notes

References

Bibliography

Further reading

External links

Navigation menu

RDX: Difference between revisions

Latest revision as of 15:46, 10 November 2025

Name

Usage

Synthesis

History

Germany

UK

Canada

UK, US, and Canadian production and development

Woolwich method

Bachmann process

Military compositions

Terrorism

Stability

Toxicity

Civilian use

Biodegradation

Alternatives

Notes

References

Bibliography

Further reading

External links

Navigation menu

Search