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{{Short description|Organic compounds with the formula (CH3)2C6H4}}
{{Short description|Organic compounds with the formula (CH3)2C6H4}}
[[File:IUPAC-cyclic.svg|thumb|400px|The three xylene isomers: [[o-Xylene|''o''-xylene]], [[m-Xylene|''m''-xylene]], and [[p-Xylene|''p''-xylene]]]]
:[[File:IUPAC-cyclic.svg|class=skin-invert-image|thumb|400px|The three xylene isomers: [[o-Xylene|''o''-xylene]], [[m-Xylene|''m''-xylene]], and [[p-Xylene|''p''-xylene]]]]
In [[organic chemistry]], '''xylene''' or '''xylol''' ({{ety|el|''ξύλον'' (xylon)|wood}};<ref>{{LSJ|cu/lon1|ξύλον|ref}}.</ref><ref>{{OEtymD|xylene}}</ref> [[IUPAC name]]: '''dimethylbenzene''') is any of three [[organic compound]]s with the formula {{chem2|(CH3)2C6H4}}. They are derived from the substitution of two [[hydrogen]] atoms with [[methyl group]]s in a [[benzene]] ring; which hydrogens are substituted determines which of three [[structural isomers]] results. It is a colorless, flammable, slightly greasy liquid of great industrial value.<ref name="Ullmann"/>
In [[organic chemistry]], '''xylene''' or '''xylol''' ({{ety|el|''ξύλον'' (xylon)|wood}};<ref>{{LSJ|cu/lon1|ξύλον|ref}}.</ref><ref>{{OEtymD|xylene}}</ref> [[IUPAC name]]: '''dimethylbenzene''') is any of three [[organic compound]]s with the formula {{chem2|(CH3)2C6H4}}. They are derived from the substitution of two [[hydrogen]] atoms with [[methyl group]]s in a [[benzene]] ring; which hydrogens are substituted determines which of three [[structural isomers]] results. It is a colorless, flammable, slightly greasy liquid of great industrial value.<ref name="Ullmann"/>
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==Industrial production==
==Industrial production==
Xylenes are produced by the [[methylation]] of [[toluene]] and [[benzene]].<ref name="Ullmann" /><ref>Martindale, David C. and Kuchar, Paul J., [https://web.archive.org/web/20180717100321/http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&p=1&u=/netahtml/PTO/search-bool.html&r=1&f=G&l=50&co1=AND&d=PTXT&s1=5043502.PN.&OS=PN/5043502&RS=PN/5043502 Production of xylenes from light aliphatic hydrocarbons via dehydrocyclodimerization and methylation], United States Patent No. 5,043,502, 1991-8-27. Accessed 2012-4-28.</ref> Commercial or [[chemical purity|laboratory-grade]] xylene produced usually contains about 40–65% of [[m-Xylene|''m''-xylene]] and up to 20% each of [[o-Xylene|''o''-xylene]], [[p-Xylene|''p''-xylene]] and [[ethylbenzene]].<ref>{{cite web |title=Xylene (Mixed Isomers), Air Toxic Hazard Summary |url=http://www.epa.gov/airtoxics/hlthef/xylenes.html |publisher=United States Environmental Protection Agency |access-date=8 February 2015}}</ref><ref name="Kandyala">{{cite journal | last1 = Kandyala | first1 = Reena | last2 = Raghavendra | first2 = Sumanth Phani C. | last3 = Rajasekharan | first3 = Saraswathi T. | year = 2010 | title = Xylene: An overview of its health hazards and preventive measures | journal = J Oral Maxillofac Pathol | volume = 14 | issue = 1| pages = 1–5 | doi = 10.4103/0973-029X.64299 | pmid = 21180450 | pmc=2996004 | doi-access = free }}</ref><ref name="Sweden">[http://apps.kemi.se/flodessok/floden/kemamne_eng/xylen_eng.htm Xylene] ({{webarchive |url=https://web.archive.org/web/20110811152832/http://apps.kemi.se/flodessok/floden/kemamne_eng/xylen_eng.htm |date=August 11, 2011 }}), Swedish Chemicals Agency, apps.kemi.se, 2010. Accessed 2012-4-28.</ref> The ratio of isomers can be shifted to favor the highly valued ''p''-xylene via the patented UOP-''Isomar'' process<ref>{{cite web |title=Capturing Opportunities for ''Para''-xylene Production |url=http://www.uop.com/?document=uop-capturing-opportunities-for-para-xylene-production-tech-paper&download=1 |publisher=UOP, A Honeywell Company |access-date=8 February 2015}}</ref> or by [[transalkylation]] of xylene with itself or trimethylbenzene. These conversions are catalyzed by [[zeolite]]s.<ref name="Ullmann" />
Xylenes are produced by the [[methylation]] of [[toluene]] and [[benzene]].<ref name="Ullmann" /><ref>Martindale, David C. and Kuchar, Paul J., [https://web.archive.org/web/20180717100321/http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&p=1&u=/netahtml/PTO/search-bool.html&r=1&f=G&l=50&co1=AND&d=PTXT&s1=5043502.PN.&OS=PN/5043502&RS=PN/5043502 Production of xylenes from light aliphatic hydrocarbons via dehydrocyclodimerization and methylation], United States Patent No. 5,043,502, 1991-8-27. Accessed 2012-4-28.</ref> Commercial or [[chemical purity|laboratory-grade]] xylene produced usually contains about 40–65% of [[m-Xylene|''m''-xylene]] and up to 20% each of [[o-Xylene|''o''-xylene]], [[p-Xylene|''p''-xylene]] and [[ethylbenzene]].<ref>{{cite web |title=Xylene (Mixed Isomers), Air Toxic Hazard Summary |url=http://www.epa.gov/airtoxics/hlthef/xylenes.html |archive-url=https://web.archive.org/web/20150208045404/http://www.epa.gov/airtoxics/hlthef/xylenes.html |url-status=dead |archive-date=February 8, 2015 |publisher=United States Environmental Protection Agency |access-date=8 February 2015}}</ref><ref name="Kandyala">{{cite journal | last1 = Kandyala | first1 = Reena | last2 = Raghavendra | first2 = Sumanth Phani C. | last3 = Rajasekharan | first3 = Saraswathi T. | year = 2010 | title = Xylene: An overview of its health hazards and preventive measures | journal = J Oral Maxillofac Pathol | volume = 14 | issue = 1| pages = 1–5 | doi = 10.4103/0973-029X.64299 | pmid = 21180450 | pmc=2996004 | doi-access = free }}</ref><ref name="Sweden">[http://apps.kemi.se/flodessok/floden/kemamne_eng/xylen_eng.htm Xylene] ({{webarchive |url=https://web.archive.org/web/20110811152832/http://apps.kemi.se/flodessok/floden/kemamne_eng/xylen_eng.htm |date=August 11, 2011 }}), Swedish Chemicals Agency, apps.kemi.se, 2010. Accessed 2012-4-28.</ref> The ratio of isomers can be shifted to favor the highly valued ''p''-xylene via the patented UOP-''Isomar'' process<ref>{{cite web |title=Capturing Opportunities for ''Para''-xylene Production |url=http://www.uop.com/?document=uop-capturing-opportunities-for-para-xylene-production-tech-paper&download=1 |publisher=UOP, A Honeywell Company |access-date=8 February 2015}}</ref> or by [[transalkylation]] of xylene with itself or trimethylbenzene. These conversions are catalyzed by [[zeolite]]s.<ref name="Ullmann" />
[[ZSM-5]] is used to facilitate some isomerization reactions leading to mass production of modern plastics.
[[ZSM-5]] is used to facilitate some isomerization reactions leading to mass production of modern plastics.
The side effects of exposure to low concentrations of xylene ({{nowrap|< 200 ppm}}) are reversible and do not cause permanent damage. Long-term exposure may lead to headaches, irritability, depression, insomnia, agitation, extreme tiredness, tremors, hearing loss, impaired concentration and short-term memory loss.<ref>{{Cite web | url=http://www.inchem.org/documents/ehc/ehc/ehc190.htm | title=Xylenes (EHC 190, 1997)}}</ref>{{clarify |reason=short-term memory loss? |date=June 2016}} A condition called [[chronic solvent-induced encephalopathy]], commonly known as "organic-solvent syndrome" has been associated with xylene exposure. There is very little information available that isolates xylene from other solvent exposures in the examination of these effects.<ref name=":0" />
The side effects of exposure to low concentrations of xylene ({{nowrap|< 200 ppm}}) are reversible and do not cause permanent damage. Long-term exposure may lead to headaches, irritability, depression, insomnia, agitation, extreme tiredness, tremors, hearing loss, impaired concentration and short-term memory loss.<ref>{{Cite web | url=http://www.inchem.org/documents/ehc/ehc/ehc190.htm | title=Xylenes (EHC 190, 1997)}}</ref>{{clarify |reason=short-term memory loss? |date=June 2016}} A condition called [[chronic solvent-induced encephalopathy]], commonly known as "organic-solvent syndrome" has been associated with xylene exposure. There is very little information available that isolates xylene from other solvent exposures in the examination of these effects.<ref name=":0" />
Hearing disorders have been also linked to xylene exposure, both from studies with experimental animals,<ref>{{Cite journal |last1=Gagnaire |first1=F. |last2=Marignac |first2=B. |last3=Langlais |first3=C. |last4=Bonnet |first4=P. |date=July 2001 |title=Ototoxicity in rats exposed to ortho-, meta- and para-xylene vapours for 13 weeks |journal=Pharmacology & Toxicology |volume=89 |issue=1 |pages=6–14 |doi=10.1034/j.1600-0773.2001.d01-129.x |doi-broken-date=15 February 2025 |issn=0901-9928 |pmid=11484912}}</ref><ref>{{Cite journal |last1=Gagnaire |first1=F. |last2=Marignac |first2=B. |last3=Blachère |first3=V. |last4=Grossmann |first4=S. |last5=Langlais |first5=C. |date=2007-03-07 |title=The role of toxicokinetics in xylene-induced ototoxicity in the rat and guinea pig |journal=Toxicology |volume=231 |issue=2–3 |pages=147–158 |doi=10.1016/j.tox.2006.11.075 |issn=0300-483X |pmid=17210216|bibcode=2007Toxgy.231..147G }}</ref> as well as clinical studies.<ref>{{Cite journal |last1=Fuente |first1=Adrian |last2=McPherson |first2=Bradley |last3=Cardemil |first3=Felipe |date=September 2013 |title=Xylene-induced auditory dysfunction in humans |journal=Ear and Hearing |volume=34 |issue=5 |pages=651–660 |doi=10.1097/AUD.0b013e31828d27d7 |issn=1538-4667 |pmid=23598724|s2cid=45206975 |hdl=10533/134303 |hdl-access=free }}</ref><ref>{{Cite journal |last1=Draper |first1=T. H. J. |last2=Bamiou |first2=D.-E. |date=April 2009 |title=Auditory neuropathy in a patient exposed to xylene: case report |journal=The Journal of Laryngology & Otology |volume=123 |issue=4 |pages=462–465 |doi=10.1017/S0022215108002399 |pmid=18439334 |issn=1748-5460|url=http://discovery.ucl.ac.uk/70543/1/S0022215108002399.pdf |archive-url=https://web.archive.org/web/20170809163223/http://discovery.ucl.ac.uk/70543/1/S0022215108002399.pdf |archive-date=2017-08-09 |url-status=live }}</ref><ref>{{Cite journal |last1=Fuente |first1=Adrian |last2=McPherson |first2=Bradley |last3=Hood |first3=Linda J. |date=November 2012 |title=Hearing loss associated with xylene exposure in a laboratory worker |journal=Journal of the American Academy of Audiology |volume=23 |issue=10 |pages=824–830 |doi=10.3766/jaaa.23.10.7 |issn=1050-0545 |pmid=23169198|hdl=10533/137495 |hdl-access=free }}</ref>
Hearing disorders have been also linked to xylene exposure, both from studies with experimental animals,<ref>{{Cite journal |last1=Gagnaire |first1=F. |last2=Marignac |first2=B. |last3=Langlais |first3=C. |last4=Bonnet |first4=P. |date=July 2001 |title=Ototoxicity in rats exposed to ortho-, meta- and para-xylene vapours for 13 weeks |journal=Pharmacology & Toxicology |volume=89 |issue=1 |pages=6–14 |doi=10.1034/j.1600-0773.2001.d01-129.x |issn=0901-9928 |pmid=11484912}}</ref><ref>{{Cite journal |last1=Gagnaire |first1=F. |last2=Marignac |first2=B. |last3=Blachère |first3=V. |last4=Grossmann |first4=S. |last5=Langlais |first5=C. |date=2007-03-07 |title=The role of toxicokinetics in xylene-induced ototoxicity in the rat and guinea pig |journal=Toxicology |volume=231 |issue=2–3 |pages=147–158 |doi=10.1016/j.tox.2006.11.075 |issn=0300-483X |pmid=17210216|bibcode=2007Toxgy.231..147G }}</ref> as well as clinical studies.<ref>{{Cite journal |last1=Fuente |first1=Adrian |last2=McPherson |first2=Bradley |last3=Cardemil |first3=Felipe |date=September 2013 |title=Xylene-induced auditory dysfunction in humans |journal=Ear and Hearing |volume=34 |issue=5 |pages=651–660 |doi=10.1097/AUD.0b013e31828d27d7 |issn=1538-4667 |pmid=23598724|s2cid=45206975 |hdl=10533/134303 |hdl-access=free }}</ref><ref>{{Cite journal |last1=Draper |first1=T. H. J. |last2=Bamiou |first2=D.-E. |date=April 2009 |title=Auditory neuropathy in a patient exposed to xylene: case report |journal=The Journal of Laryngology & Otology |volume=123 |issue=4 |pages=462–465 |doi=10.1017/S0022215108002399 |pmid=18439334 |issn=1748-5460|url=http://discovery.ucl.ac.uk/70543/1/S0022215108002399.pdf |archive-url=https://web.archive.org/web/20170809163223/http://discovery.ucl.ac.uk/70543/1/S0022215108002399.pdf |archive-date=2017-08-09 |url-status=live }}</ref><ref>{{Cite journal |last1=Fuente |first1=Adrian |last2=McPherson |first2=Bradley |last3=Hood |first3=Linda J. |date=November 2012 |title=Hearing loss associated with xylene exposure in a laboratory worker |journal=Journal of the American Academy of Audiology |volume=23 |issue=10 |pages=824–830 |doi=10.3766/jaaa.23.10.7 |issn=1050-0545 |pmid=23169198|hdl=10533/137495 |hdl-access=free }}</ref>
Xylene is also a skin irritant and strips the skin of its oils, making it more permeable to other chemicals. The use of impervious gloves and masks, along with respirators where appropriate, is recommended to avoid occupational health issues from xylene exposure.<ref name=":0" />
Xylene is also a skin irritant and strips the skin of its oils, making it more permeable to other chemicals. The use of impervious gloves and masks, along with respirators where appropriate, is recommended to avoid occupational health issues from xylene exposure.<ref name=":0" />
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==See also==
==See also==
* [[Alkylbenzene]]
* {{annotated link|Alkylbenzene}}
* [[C2-Benzenes]]
* {{annotated link|C2-Benzenes}}
* [[Hydrodealkylation]]
* {{annotated link|Hydrodealkylation}}
* [[Transalkylation]]
* {{annotated link|Transalkylation}}
* [[Xylene cyanol]]
* {{annotated link|Xylene cyanol}}
==References==
==References==
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*[https://www.cdc.gov/niosh/npg/npgd0670.html NIOSH Pocket Guide to Chemical Hazards] (''p''-Xylene)
*[https://www.cdc.gov/niosh/npg/npgd0670.html NIOSH Pocket Guide to Chemical Hazards] (''p''-Xylene)
The mixture is referred to as both xylene and, more precisely, xylenes. Mixed xylenes refers to a mixture of the xylenes plus ethylbenzene. The four compounds have identical molecular formulasTemplate:Chem2. Typically the four compounds are produced together by various catalytic reforming and pyrolysis methods.[4]
Several million tons are produced annually.[3] In 2011, a global consortium began construction of one of the world's largest xylene plants in Singapore.[5]
History
Xylene was first isolated and named in 1850 by the French chemist Auguste Cahours (1813–1891), having been discovered as a constituent of wood tar.[6]
ZSM-5 is used to facilitate some isomerization reactions leading to mass production of modern plastics.
Properties
The physical properties of the isomers of xylene differ slightly. The melting point ranges from Template:Convert (m-xylene) to Template:Convert (p-xylene)—as usual, the para isomer's melting point is much higher because it packs more readily in the crystal structure. The boiling point for each isomer is around Template:Convert. The density of each isomer is around Template:Convert and thus is less dense than water. The odor of xylene is detectable at concentrations as low as 0.08 to 3.7 ppm (parts of xylene per million parts of air) and can be tasted in water at 0.53 to 1.8 ppm.[9]
Xylenes form azeotropes with water and a variety of alcohols. The azeotrope with water consists of 60% xylenes and boils at 94.5 °C.[3] As with many alkylbenzene compounds, xylenes form complexes with various halocarbons.[12] The complexes of different isomers often have dramatically different properties from each other.[13]
Xylenes are used as a solvent in printing, rubber, and leather industries. It is a common component of ink, rubber, and adhesives.[15] In thinning paints and varnishes, it can be substituted for toluene where slower drying is desired, and thus is used by conservators of art objects in solubility testing.[16] Similarly it is a cleaning agent, e.g., for steel, silicon wafers, and integrated circuits. In dentistry, xylene can be used to dissolve gutta percha, a material used for endodontics (root-canal treatments). In the petroleum industry, xylene is also a frequent component of paraffin solvents, used when the tubing becomes clogged with paraffin wax.
Laboratory use
Xylene is used in the laboratory to make baths with dry ice to cool reaction vessels,[17] and as a solvent to remove synthetic immersion oil from the microscope objective in light microscopy.[18] In histology, xylene is the most widely used clearing agent.[19] Xylene is used to remove paraffin from dried microscope slides prior to staining. After staining, microscope slides are put in xylene prior to mounting with a coverslip.
Generally, two kinds of reactions occur with xylenes: those involving the methyl groups and those involving the ring C–H bonds. Being benzylic and hence weakened, the C–H bonds of the methyl groups are susceptible to free-radical reactions, including halogenation to the corresponding xylene dichlorides (bis(chloromethyl)benzenes), while mono-bromination yields xylyl bromide, a tear gas agent. Oxidation and ammoxidation also target the methyl groups, affording dicarboxylic acids and the dinitriles. Electrophiles attack the aromatic ring, leading to chloro- and nitroxylenes.[3]
Health and safety
Xylene is flammable but of modest acute toxicity, with LD50 ranges from 200 to 5000 mg/kg for animals. Oral LD50 for rats is 4300 mg/kg. The principal mechanism of detoxification is oxidation to methylbenzoic acid and hydroxylation to hydroxylene.[3]
The main effect of inhaling xylene vapor is depression of the central nervous system (CNS), with symptoms such as headache, dizziness, nausea and vomiting. At an exposure of 100 ppm, one may experience nausea or a headache. At an exposure between 200 and 500 ppm, symptoms can include feeling "high", dizziness, weakness, irritability, vomiting, and slowed reaction time.[20][21]
The side effects of exposure to low concentrations of xylene (< 200 ppm) are reversible and do not cause permanent damage. Long-term exposure may lead to headaches, irritability, depression, insomnia, agitation, extreme tiredness, tremors, hearing loss, impaired concentration and short-term memory loss.[22]Template:Clarify A condition called chronic solvent-induced encephalopathy, commonly known as "organic-solvent syndrome" has been associated with xylene exposure. There is very little information available that isolates xylene from other solvent exposures in the examination of these effects.[20]
Hearing disorders have been also linked to xylene exposure, both from studies with experimental animals,[23][24] as well as clinical studies.[25][26][27]
Xylene is also a skin irritant and strips the skin of its oils, making it more permeable to other chemicals. The use of impervious gloves and masks, along with respirators where appropriate, is recommended to avoid occupational health issues from xylene exposure.[20]
↑Cahours, Auguste (1850) "Recherches sur les huiles légéres obtenues dans la distillation du bois" (Investigations of light oils obtained by the distillation of wood), Compte rendus, 30 : 319-323; see especially p. 321. From p. 321: "Je le désignerai sous le nomme xylène." (I will designate it by the name of xylene.) Note: Cahours' empirical formula for xylene is incorrect because chemists at that time used the wrong atomic mass for carbon (6 instead of 12).
↑Samet, Wendy, (comp.), Appendix I, Painting Conservation Catalog, American Institute for Conservation of Historic and Artistic Works, conservation-wiki.com, September 1997. Accessed 2012-04-28.
