View source for 1,2-Dichloroethane

{{Use dmy dates|date=October 2023}}
{{chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 477203605
| Name           = 1,2-Dichloroethane
| ImageFileL1    = 1,2-dichloroethane.svg
| ImageNameL1    = 1,2-Dichloroethane
| ImageFileR1    = 1,2-dichloroethane-3D-vdW.png
| ImageNameR1    = 1,2-Dichloroethane
| PIN            = 1,2-Dichloroethane
| OtherNames     = Ethylene dichloride<br/>Ethylene chloride<br/>1,2-DCA<br/>1,2-DCE
<br/>DCE<ref>{{cite web |title=Standard Abbreviations and Acronyms |url=http://pubs.acs.org/paragonplus/submission/joceah/joceah_abbreviations.pdf |author=Staff writer |website=The Journal of Organic Chemistry |quote= DCE: 1,2-dichloroethane}}</ref><br/>Ethane dichloride<br/>Dutch liquid, Dutch oil<br/>Freon 150
| Section1       = {{Chembox Identifiers
| SMILES = ClCCCl 
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H4Cl2/c3-1-2-4/h1-2H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WSLDOOZREJYCGB-UHFFFAOYSA-N 
| 3DMet = B01041 
| CASNo = 107-06-2 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13837650
| PubChem = 11
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 27789
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 16370
| DrugBank = DB03733
| EC_number = 203-458-1
| Gmelin = 49272
| Beilstein = 605264
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 55163IJI47
| RTECS = KI0525000  
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C06752
  }}
| Section2       = {{Chembox Properties
| C=2 | H=4 | Cl=2
| Appearance = Colorless liquid
| Odor = characteristic, pleasant chloroform-like odor<ref name=PGCH/>
| Density = 1.253&nbsp;g/cm{{sup|3}}, liquid  
| Solubility = 0.87&nbsp;g/100 mL (20&nbsp;°C)  
| MeltingPtC = −35
| BoilingPtC = 84
| Viscosity = 0.84&nbsp;[[Pascal second|mPa·s]] at 20&nbsp;°C  
  }}
| Section3       = {{Chembox Structure
| Dipole = 1.80&nbsp;[[Debye|D]]  
  }}
| Section7       = {{Chembox Hazards
| MainHazards = Toxic, flammable, possibly carcinogenic
| NFPA-H = 2  
| NFPA-F = 3   
| NFPA-R = 0
| NFPA-S = 
| FlashPtC = 13
| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|302|315|319|335|350}}
| PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|261|264|270|271|280|281|301+312|302+352|303+361+353|304+340|305+351+338|308+313|312|321|330|332+313|337+313|362|370+378|403+233|403+235|405|501}}
| PEL = TWA 50 ppm C 100 ppm 200 ppm [5-minute maximum peak in any 3 hours]<ref name=PGCH>{{PGCH|0271}}</ref>
| ExploLimits = 6.2–16%<ref name=PGCH/>
| IDLH = Ca [50 ppm]<ref name=PGCH/>
| REL = Ca TWA 1 ppm (4 mg/m{{sup|3}}) ST 2 ppm (8 mg/m{{sup|3}})<ref name=PGCH/>
| LC50 = 3000 ppm (guinea pig, 7&nbsp;[[hour|h]])<br/>1000 ppm (rat, 7&nbsp;h)<ref name=IDLH>{{IDLH|107062|Ethylene dichloride}}</ref>
| LCLo = 1217 ppm (mouse, 2&nbsp;h)<br/>1000 ppm (rat, 4&nbsp;h)<br/>3000 ppm (rabbit, 7&nbsp;h)<ref name=IDLH/>
  }}
| Section8       = {{Chembox Related
| OtherFunction_label = [[haloalkane]]s  
| OtherFunction = [[Methyl chloride]]<br/>[[Methylene chloride]]<br/>[[1,1,1-Trichloroethane]]  
| OtherCompounds = [[Ethylene]]<br/>[[1,1-Dichloroethane]]<br/>[[Vinyl chloride]]
  
  }}
}}

The [[chemical compound]] '''1,2-dichloroethane''', commonly known as '''ethylene dichloride''' ('''EDC'''), is a [[chlorinated hydrocarbon]].  It is a colourless [[liquid]] with a [[chloroform]]-like [[odour]]. The most common use of 1,2-dichloroethane is in the production of [[vinyl chloride]], which is used to make [[polyvinyl chloride]] (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts.<ref>{{Cite web |title = Toxic Substances – 1,2-Dichloroethane |url = https://wwwn.cdc.gov/TSP/index.aspx?toxid=110 |website = ATSDR |access-date = 2015-09-23}}</ref> 1,2-Dichloroethane is also used generally as an intermediate for other [[organic chemical compound]]s, and as a [[solvent]]. It forms [[azeotrope]]s with many other [[solvent]]s, including water (at a boiling point of&nbsp;{{Cvt|70.5|C|F K|abbr=|disp=or}}) and other [[chlorocarbons]].<ref>Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, Trevor Mann "Chlorinated Hydrocarbons" in ''Ullmann's Encyclopedia of Industrial Chemistry''. 2006, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a06_233.pub2}}.</ref>

==History==
In 1794, physician [[Jan Rudolph Deiman]], merchant [[Adriaan Paets van Troostwijk]], chemist Anthoni Lauwerenburg, and botanist Nicolaas Bondt, under the name of Society of Dutch Chemists ({{langx|nl|Gezelschap der Hollandsche Scheikundigen}}), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas, [[ethylene]]) and [[chlorine]] gas.<ref>Deimann, van Troostwyk, Bondt and Louwrenburgh (1795) [https://books.google.com/books?id=SFAyAQAAMAAJ&pg=PA173 "Ueber die Gasarten, welche man aus Verbindungen von starker Vitriolsäure und Alkohol erhält"] (On the types of gases which one obtains from combinations of strong vitriolic acid and alcohol), ''Chemische Annalen'' ... , '''2''' :  195-205, 310-316, 430-440.  The production and characterization of 1,2-dichloroethane appear on pages 200-202.  The investigators were trying to detect the presence of carbon (''Kohl'') in ethylene (''Luft'', literally, "air") by adding chlorine (''zündend Salzgas'', literally, "burning gas from salt").  Instead of the expected soot, an oil (''Oehl'') formed.</ref> Although the ''Gezelschap'' in practice did not do much in-depth scientific research, they and their publications were highly regarded. Part of that acknowledgement is that 1,2-dichloroethane was called "Dutch oil" in old chemistry.  This is also the origin of the archaic term "olefiant gas" (oil-making gas) for ethylene, for in this reaction it is ethylene that makes the Dutch oil.  "Olefiant gas" is the etymological origin of the modern term "olefins", the family of hydrocarbons of which ethylene is the first member.

==Production==
Nearly 20 million tons of 1,2-dichloroethane are produced annually in the [[United States]], [[Western Europe]], and [[Japan]].<ref>{{cite journal
| author=J.A. Field
| author2=R. Sierra-Alvarez
| name-list-style=amp
| year=2004
| title=Biodegradability of chlorinated solvents and related chlorinated aliphatic compounds
| journal=Rev. Environ. Sci. Biotechnol.
| volume=3
| issue=3
| pages=185–254
| doi=10.1007/s11157-004-4733-8
| bibcode=2004RESBT...3..185F
| s2cid=36536985
}}</ref> Production is primarily achieved through the [[iron(III) chloride]]-[[Catalysis|catalysed reaction]] of ethylene and chlorine:
:{{chem2|H2C\dCH2 (g) + Cl2 (g) -> ClC2H4Cl (l)}} ([[Standard enthalpy of reaction|Δ''H''<sup>⊖</sup><sub>r</sub>]] = −218 kJ/mol)

1,2-dichloroethane is also generated by the [[copper(II) chloride]]-catalysed [[oxychlorination]] of ethylene:
:{{chem2|H2C\dCH2 + 2 HCl}} + {{sfrac|1|2}} {{chem2|O2 -> ClC2H4Cl + H2O}}

==Uses==

===Vinyl chloride production===
Approximately 95% of the world's production of 1,2-dichloroethane is used in the production of [[vinyl chloride]] [[monomer]] (VCM) with [[hydrogen chloride]] as a byproduct. VCM is the precursor to [[polyvinyl chloride]].

:{{chem2|ClC2H4Cl -> H2C\dCHCl + HCl}}

The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via the [[oxychlorination]] route described above.<ref>{{cite web|url=https://www.ihs.com/products/ethylene-dichloride-chemical-economics-handbook.html|title=Ethylene Dichloride – Chemical Economics Handbook (CEH) – IHS Markit|website=ihs.com|access-date=8 April 2018}}</ref>

===Other uses===
1,2-Dichloroethane has been used as degreaser and paint remover but this use has phased out due to its [[toxicity]]. As a useful 'building block' reagent, it is used as an intermediate in the production of diverse organic compounds such as [[ethylenediamine]] and higher [[ethyleneamines]].<ref name = kirk>{{Kirk-Othmer | title = Diamines and Higher Amines, Aliphatic | author1 = Srivasan Sridhar | author2 = Richard G. Carter | doi = 10.1002/0471238961.0409011303011820.a01.pub2 | year = 2001 | mode = cs1}}</ref> In the laboratory it is occasionally used as a source of [[chlorine]], with elimination of ethene and chloride.

Via several steps, 1,2-dichloroethane is a precursor to [[1,1,1-trichloroethane]]. Historically, before leaded petrol was phased out, chloroethanes were used as an additive in petrol to prevent lead buildup in engines.<ref name="Seyferth">{{cite journal | author = Seyferth, D. | title = The Rise and Fall of Tetraethyllead. 2 | journal = [[Organometallics]] | year = 2003 | volume = 22 | issue = 25 | pages = 5154–5178 | doi = 10.1021/om030621b| doi-access =  }}</ref>

==Safety==
1,2-Dichloroethane is highly [[flammable]]<ref>"1,2-Dichoroethane MSDS." Mallinckrodt Chemicals. 19 May 2008. Web. <http://hazard.com/msds/mf/baker/baker/files/d2440.htm>.</ref> and releases [[hydrochloric acid]] when combusted:

:{{chem2|ClC2H4Cl}} + {{sfrac|5|2}} {{chem2|O2 -> 2 CO2 + H2O + 2 HCl}}

It is also [[toxic]] (especially by inhalation due to its high [[vapour pressure]]) and possibly [[carcinogen]]ic. Its high [[solubility]] and 50-year [[half-life]] in [[anoxic waters|anoxic]] [[aquifer]]s make it a perennial pollutant and health risk that is very expensive to treat conventionally, requiring a method of [[bioremediation]].<ref>{{cite journal
| author=S. De Wildeman
| author2=W. Verstraete
| name-list-style=amp
| date=25 March 2003
| title=The quest for microbial reductive dechlorination of C2 to C4 chloroalkanes is warranted
| journal=Appl. Microbiol. Biotechnol.
| volume=61
| issue=2
| pages=94–102
| doi=10.1007/s00253-002-1174-6
| pmid=12655450
| s2cid=72921
}}</ref> While the chemical is not used in consumer products manufactured in the U.S., a case was reported in 2009 of molded plastic consumer products (toys and holiday decorations) from [[China]] that released 1,2-dichloroethane into homes at levels high enough to produce cancer risk.<ref>{{cite web|url=http://www.rodale.com/plastic-christmas-ornaments?page=0%2C0|title=Toxic Christmas: Plastic Ornaments May Pollute Your Air|website=rodale.com|access-date=8 April 2018|archive-url=https://web.archive.org/web/20120318162835/http://www.rodale.com/plastic-christmas-ornaments?page=0,0|archive-date=18 March 2012|url-status=dead}}</ref><ref>{{cite journal
| author=Doucette, WJ
| author2=Hall, AJ
| author3=Gorder, KA
| name-list-style=amp
| date=Winter 2010
| title=Emissions of 1, 2-Dichloroethane from Holiday Decorations as a Source of Indoor Air Contamination
| journal=Ground Water Monitoring & Remediation
| volume= 30
| issue=1
| pages=67–73
| doi=10.1111/j.1745-6592.2009.01267.x
| bibcode=2010GMRed..30a..67D
| citeseerx=10.1.1.1013.1487
| s2cid=96563330
}}</ref>

Substitutes are recommended and will vary according to application. [[Dioxolane]] and [[toluene]] are possible substitutes as solvents. [[Dichloroethane]] is unstable in the presence of [[aluminium]] and, when moist, with [[zinc]] and [[iron]].{{citation needed|date=June 2016}}

==References==
{{reflist}}

==External links==
* [https://web.archive.org/web/20050908231559/http://www.scholarly-societies.org/history/1790ghs.html Gezelschap der Hollandsche Scheikundigen]
* [https://archive.today/20130102043336/http://www.chemicalland21.com/arokorhi/industrialchem/organic/ETHYLENE%20DICHLORIDE.htm  ChemicalLand compound database]
* [http://environmentalchemistry.com/yogi/chemicals/cn/Ethylene%A0Dichloride.html Environmental Chemistry compound database]
* [https://web.archive.org/web/20080304085557/http://chemdat.merck.de/pls/pi03/web2.search_page2?text=100955&lang=4 Merck Chemicals database]
* [https://web.archive.org/web/20060820040740/http://www.npi.gov.au/database/substance-info/profiles/33.html National Pollutant Inventory – 1,2 Dichlorethane Fact Sheet]
* [http://www.epa.gov/ttn/chief/le/ethyldi.pdf Locating and estimating air emissions from sources of ethylene dichloride, EPA report EPA-450/4-84-007d, March 1984]

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{{DEFAULTSORT:Dichloroethane, 1, 2-}}
[[Category:IARC Group 2B carcinogens]]
[[Category:Organochloride insecticides]]
[[Category:Chloroalkanes]]
[[Category:Plastics]]
[[Category:Halogenated solvents]]
[[Category:Fuel additives]]