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Xylene

Xylene (from Greekξύλον xylon, "wood"), xylol or dimethylbenzene is any one of three isomers of dimethylbenzene, or a combination thereof. With the formula (CH3)2C6H4, in each of the three compounds a benzene ring is substituted by two methyl groups. They are all colorless, flammable, slightly greasy liquids. They are of great industrial value. 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 empirical formulas C8H10. Typically the four compounds are produced together by various catalytic reforming and pyrolysis methods.

Xylenes are an important petrochemical produced by catalytic reforming and also by coal carbonisation in the manufacture of coke fuel. They also occur in crude oil in concentrations of about 0.5–1%, depending on the source. Small quantities occur in gasoline and aircraft fuels.

Xylenes are produced mainly as part of the BTX aromatics (benzene, toluene, and xylenes) extracted from the product of catalytic reforming known as reformate.

Several million tons are produced annually. In 2011, a global consortium began construction of one of the world's largest xylene plants in Singapore.

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.

Xylenes are produced by the methylation of toluene and benzene. Commercial or laboratory-grade xylene produced usually contains about 40-65% of m-xylene and up to 20% each of o-xylene, p-xylene and ethylbenzene. The ratio of isomers can be shifted to favor the highly valued p-xylene via the patented UOP-Isomar process or by transalkylation of xylene with itself or trimethylbenzene. These conversions are catalyzed by zeolites.

ZSM-5 is used to facilitate some isomerization reactions leading to mass production of modern plastics.

The physical properties of the isomers of xylene differ slightly. The melting point ranges from −47.87 °C (−54.17 °F) (m-xylene) to 13.26 °C (55.87 °F) (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 140 °C (284 °F). The density of each isomer is around 0.87 g/mL (7.26 lb/U.S. gallon or 8.72 lb/imp gallon) 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.

Xylene isomers
General
Common name Xylene o-Xylene m-Xylene p-Xylene
Systematic name Dimethylbenzene 1,2-Dimethylbenzene 1,3-Dimethylbenzene 1, 4-Dimethylbenzene
Other names Xylol o-Xylol;
Orthoxylene
m-Xylol;
Metaxylene
p-Xylol;
Paraxylene
Molecular formula C8H10
SMILES Cc1c(C)cccc1 Cc1cc(C)ccc1 Cc1ccc(C)cc1
Molar mass 106.16 g/mol
Appearance Clear, colorless liquid
CAS number [1330-20-7] [95-47-6] [108-38-3] [106-42-3]
Properties
Density and phase 0.864 g/mL, liquid 0.88 g/mL, liquid 0.86 g/mL, liquid 0.86 g/mL, liquid
Solubility in water Practically insoluble
Soluble in non-polar solvents such as aromatic hydrocarbons
Melting point −47.4 °C (−53.3 °F; 226 K) −25 °C (−13 °F; 248 K) −48 °C (−54 °F; 225 K) 13 °C (55 °F; 286 K)
Boiling point 138.5 °C (281.3 °F; 412 K) 144 °C (291 °F; 417 K) 139 °C (282 °F; 412 K) 138 °C (280 °F; 411 K)
Viscosity 0.812 cP at 20 °C (68 °F) 0.62 cP at 20 °C (68 °F) 0.34 cP at 30 °C (86 °F)
Hazards
SDS Xylenes o-Xylene m-Xylene p-Xylene
EU pictograms


NFPA 704
2
3
0
Flash point 30 °C (86 °F) 17 °C (63 °F) 25 °C (77 °F) 25 °C (77 °F)
H & P phrases H225, H226, H304, H312, H312, H315, H319, H332, H335, H412

P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+310, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P312, P321, P322, P331, P332+313, P337+313, P362, P363

RTECS number ZE2450000 ZE2275000 ZE2625000
Related compounds
Related aromatic
hydrocarbons
Toluene, mesitylene, benzene, ethylbenzene
Related compounds Xylenols - types of phenols
Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100kPa)
Infobox disclaimer and references

Xylenes form azeotropes with water and a variety of alcohols. With water the azeotrope consists of 60% xylenes and boils at 94.5 °C. As with many alkylbenzene compounds, xylenes form complexes with various halocarbons. The complexes of different isomers often have dramatically different properties from each other.

Terephthalic acid and related derivatives

p-Xylene is the principal precursor to terephthalic acid and dimethyl terephthalate, both monomers used in the production of polyethylene terephthalate (PET) plastic bottles and polyester clothing. 98% of p-xylene production, and half of all xylenes produced is consumed in this manner. o-Xylene is an important precursor to phthalic anhydride. The demand for isophthalic acid is relatively modest so m-xylene is rarely sought (and hence the utility of its conversion to the o- and p-isomers).

Solvent applications and industrial purposes

Xylenes are used as a solvent in printing, rubber, and leather industries. It is a common component of ink, rubber, and adhesives. 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. 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, and as a solvent to remove synthetic immersion oil from the microscope objective in light microscopy. In histology, xylene is the most widely used clearing agent. 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.

Precursor to other compounds

In one large scale application, para-xylene is converted to terephthalic acid. The major application of ortho-xylene is as a precursor to phthalate esters, used as plasticizer. Meta-xylene is converted to isophthalic acid derivatives, which are components of alkyd resins.

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.

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.

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.

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.[clarification needed] 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.

Hearing disorders have been also linked to xylene exposure, both from studies with experimental animals, as well as clinical studies.

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.

Xylenes are metabolized to methylhippuric acids. The presence of methylhippuric acid can be used as a biomarker to determine exposure to xylene.

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  7. Martindale, David C. and Kuchar, Paul J., 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.
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  13. Clark J. E.; Luthy, R. V. (1955). "Separation of Xylenes". Ind. Eng. Chem. 47 (2): 250–253. doi:10.1021/ie50542a028.
  14. Stevenson, Cheryl D; McElheny, Daniel J; Kage, David E; Ciszewski, James T; Reiter, Richard C (1998). "Separation of Closely Boiling Isomers and Identically Boiling Isotopomers via Electron-Transfer-Assisted Extraction". Analytical Chemistry. 70 (18): 3880. doi:10.1021/ac980221b.
  15. ICIS, Paraxylene-Orthoxylene | Prices, News & Market Analysis, icis.com, 2012. Accessed 2012-4-28.
  16. Bostik, Safety Data Sheet Blu-Tack Archived September 11, 2011, at the Wayback Machine, No. 13135, Bostik Corp., 2007-6. Accessed 2012-4-28.
  17. Samet, Wendy, (comp.), Appendix I, Painting Conservation Catalog, American Institute for Conservation of Historic and Artistic Works, conservation-wiki.com, 1997-9. Accessed 2012-4-28.
  18. "Cooling baths". UC Davis Chem Wiki. 2013-10-02. Retrieved8 February 2015.
  19. Cargille, John (1985) [1964], "Immersion Oil and the Microscope", New York Microscopical Society Yearbook, archived from the original on 2011-09-11, retrieved2011-03-10
  20. Carson, Freida; Hladik, Christa (2009). Histotechnology: A Self-Instructional Text (3 ed.). American Society for Clinical Pathology Press. p. 35. ISBN 9780891895817.
  21. Kandyala, Reena; Raghavendra, Sumanth Phani C.; Rajasekharan, Saraswathi T. (2010-01-01). "Xylene: An overview of its health hazards and preventive measures". Journal of Oral and Maxillofacial Pathology. 14 (1): 1–5. doi:10.4103/0973-029X.64299. ISSN 0973-029X. PMC2996004. PMID 21180450.
  22. "ACUTE TOXICITY SUMMARY: XYLENES"(PDF). Archived from the original(PDF) on October 22, 2015.
  23. "Xylenes (EHC 190, 1997)".
  24. Gagnaire, F.; Marignac, B.; Langlais, C.; Bonnet, P. (July 2001). "Ototoxicity in rats exposed to ortho-, meta- and para-xylene vapours for 13 weeks". Pharmacology & Toxicology. 89 (1): 6–14. doi:10.1034/j.1600-0773.2001.d01-129.x. ISSN 0901-9928. PMID 11484912.
  25. Gagnaire, F.; Marignac, B.; Blachère, V.; Grossmann, S.; Langlais, C. (2007-03-07). "The role of toxicokinetics in xylene-induced ototoxicity in the rat and guinea pig". Toxicology. 231 (2–3): 147–158. doi:10.1016/j.tox.2006.11.075. ISSN 0300-483X. PMID 17210216.
  26. Fuente, Adrian; McPherson, Bradley; Cardemil, Felipe (September 2013). "Xylene-induced auditory dysfunction in humans". Ear and Hearing. 34 (5): 651–660. doi:10.1097/AUD.0b013e31828d27d7. hdl:10533/134303. ISSN 1538-4667. PMID 23598724. S2CID 45206975.
  27. Draper, T. H. J.; Bamiou, D.-E. (April 2009). "Auditory neuropathy in a patient exposed to xylene: case report"(PDF). The Journal of Laryngology & Otology. 123 (4): 462–465. doi:10.1017/S0022215108002399. ISSN 1748-5460. PMID 18439334.
  28. Fuente, Adrian; McPherson, Bradley; Hood, Linda J. (November 2012). "Hearing loss associated with xylene exposure in a laboratory worker". Journal of the American Academy of Audiology. 23 (10): 824–830. doi:10.3766/jaaa.23.10.7. hdl:10533/137495. ISSN 1050-0545. PMID 23169198.
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  30. Inoue, O.; Seiji, K.; Kawai, T.; Watanabe, T.; Jin, C.; Cai, S. X.; Chen, Z.; Qu, Q. S.; Zhang, T.; Ikeda, M. (1993). "Excretion of methylhippuric acids in urine of workers exposed to a xylene mixture: Comparison among three xylene isomers and toluene". International Archives of Occupational and Environmental Health. 64 (7): 533–539. doi:10.1007/bf00381104. PMID 8482596. S2CID 21534640.
  31. Kira S. (1977). "Measurement by gas chromatography of urinary hippuric acid and methylhippuric acid as indices of toluene and xylene exposure". Occupational and Environmental Medicine. 34 (305–309): 305–309. doi:10.1136/oem.34.4.305. PMC1008281. PMID 588486.
Wikimedia Commons has media related toXylenes.

Xylene
Xylene Language Watch Edit 160 160 Redirected from Xylol Xylene from Greek 3ylon xylon wood 1 2 xylol or dimethylbenzene is any one of three isomers of dimethylbenzene or a combination thereof With the formula CH3 2C6H4 in each of the three compounds a benzene ring is substituted by two methyl groups They are all colorless flammable slightly greasy liquids They are of great industrial value 3 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 empirical formulas C8H10 Typically the four compounds are produced together by various catalytic reforming and pyrolysis methods 4 The three xylene isomers o xylene m xylene and p xylene Contents 1 Occurrence and production 2 History 3 Industrial production 4 Properties 5 Applications 5 1 Terephthalic acid and related derivatives 5 2 Solvent applications and industrial purposes 5 3 Laboratory use 5 4 Precursor to other compounds 6 Chemical properties 7 Health and safety 8 See also 9 References 10 External linksOccurrence and production EditXylenes are an important petrochemical produced by catalytic reforming and also by coal carbonisation in the manufacture of coke fuel They also occur in crude oil in concentrations of about 0 5 1 depending on the source Small quantities occur in gasoline and aircraft fuels Xylenes are produced mainly as part of the BTX aromatics benzene toluene and xylenes extracted from the product of catalytic reforming known as reformate 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 EditXylene 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 Industrial production EditXylenes are produced by the methylation of toluene and benzene 3 7 Commercial or laboratory grade xylene produced usually contains about 40 65 of m xylene and up to 20 each of o xylene p xylene and ethylbenzene 8 9 10 The ratio of isomers can be shifted to favor the highly valued p xylene via the patented UOP Isomar process 11 or by transalkylation of xylene with itself or trimethylbenzene These conversions are catalyzed by zeolites 3 ZSM 5 is used to facilitate some isomerization reactions leading to mass production of modern plastics Properties EditThe physical properties of the isomers of xylene differ slightly The melting point ranges from 47 87 C 54 17 F m xylene to 13 26 C 55 87 F 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 140 C 284 F The density of each isomer is around 0 87 g mL 7 26 lb U S gallon or 8 72 lb imp gallon 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 Xylene isomersGeneralCommon name Xylene o Xylene m Xylene p XyleneSystematic name Dimethylbenzene 1 2 Dimethylbenzene 1 3 Dimethylbenzene 1 4 DimethylbenzeneOther names Xylol o Xylol Orthoxylene m Xylol Metaxylene p Xylol ParaxyleneMolecular formula C8H10SMILES Cc1c C cccc1 Cc1cc C ccc1 Cc1ccc C cc1Molar mass 106 16 g molAppearance Clear colorless liquidCAS number 1330 20 7 95 47 6 108 38 3 106 42 3 PropertiesDensity and phase 0 864 g mL liquid 0 88 g mL liquid 0 86 g mL liquid 0 86 g mL liquidSolubility in water Practically insolubleSoluble in non polar solvents such as aromatic hydrocarbonsMelting point 47 4 C 53 3 F 226 K 25 C 13 F 248 K 48 C 54 F 225 K 13 C 55 F 286 K Boiling point 138 5 C 281 3 F 412 K 144 C 291 F 417 K 139 C 282 F 412 K 138 C 280 F 411 K Viscosity 0 812 cP at 20 C 68 F 0 62 cP at 20 C 68 F 0 34 cP at 30 C 86 F HazardsSDS Xylenes 12 o Xylene m Xylene p XyleneEU pictograms NFPA 704 230Flash point 30 C 86 F 17 C 63 F 25 C 77 F 25 C 77 F H amp P phrases H225 H226 H304 H312 H312 H315 H319 H332 H335 H412 P210 P233 P240 P241 P242 P243 P261 P264 P271 P273 P280 P301 310 P302 352 P303 361 353 P304 312 P304 340 P305 351 338 P312 P321 P322 P331 P332 313 P337 313 P362 P363RTECS number ZE2450000 ZE2275000 ZE2625000Related compoundsRelated aromatic hydrocarbons Toluene mesitylene benzene ethylbenzeneRelated compounds Xylenols types of phenolsExcept where noted otherwise data are given for materials in their standard state at 25 C 100 kPa Infobox disclaimer and references Xylenes form azeotropes with water and a variety of alcohols With water the azeotrope consists of 60 xylenes and boils at 94 5 C 3 As with many alkylbenzene compounds xylenes form complexes with various halocarbons 13 The complexes of different isomers often have dramatically different properties from each other 14 Applications EditTerephthalic acid and related derivatives Edit p Xylene is the principal precursor to terephthalic acid and dimethyl terephthalate both monomers used in the production of polyethylene terephthalate PET plastic bottles and polyester clothing 98 of p xylene production and half of all xylenes produced is consumed in this manner 10 15 o Xylene is an important precursor to phthalic anhydride The demand for isophthalic acid is relatively modest so m xylene is rarely sought and hence the utility of its conversion to the o and p isomers Solvent applications and industrial purposes Edit Xylenes are used as a solvent in printing rubber and leather industries It is a common component of ink rubber and adhesives 16 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 17 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 Edit Xylene is used in the laboratory to make baths with dry ice to cool reaction vessels 18 and as a solvent to remove synthetic immersion oil from the microscope objective in light microscopy 19 In histology xylene is the most widely used clearing agent 20 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 Precursor to other compounds Edit In one large scale application para xylene is converted to terephthalic acid The major application of ortho xylene is as a precursor to phthalate esters used as plasticizer Meta xylene is converted to isophthalic acid derivatives which are components of alkyd resins 3 Chemical properties EditGenerally 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 EditXylene 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 21 22 The side effects of exposure to low concentrations of xylene lt 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 23 clarification needed 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 21 Hearing disorders have been also linked to xylene exposure both from studies with experimental animals 24 25 as well as clinical studies 26 27 28 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 21 Xylenes are metabolized to methylhippuric acids 29 30 The presence of methylhippuric acid can be used as a biomarker to determine exposure to xylene 30 31 See also Edito Xylene m Xylene p Xylene Xylene cyanol Hydrodealkylation Transalkylation AlkylbenzeneReferences Edit 3ylon Liddell Henry George Scott Robert A Greek English Lexicon at the Perseus Project Harper Douglas xylene Online Etymology Dictionary a b c d e f g h Fabri Jorg Graeser Ulrich Simo Thomas A 2000 Xylenes Ullmann s Encyclopedia of Industrial Chemistry doi 10 1002 14356007 a28 433 ISBN 978 3527306732 Cannella William J 2000 Xylenes and Ethylbenzene Kirk Othmer Encyclopedia of Chemical Technology doi 10 1002 0471238961 2425120503011414 a01 ISBN 0471238961 Tremblay Jean Francois 2011 Making Aromatics in Singapore Chemical amp Engineering News Archive 89 38 18 19 doi 10 1021 cen v089n038 p018 Cahours Auguste 1850 Recherches sur les huiles legeres 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 designerai sous le nommexylene 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 Martindale David C and Kuchar Paul J 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 Xylene Mixed Isomers Air Toxic Hazard Summary United States Environmental Protection Agency Retrieved 8 February 2015 a b Kandyala Reena Raghavendra Sumanth Phani C Rajasekharan Saraswathi T 2010 Xylene An overview of its health hazards and preventive measures J Oral Maxillofac Pathol 14 1 1 5 doi 10 4103 0973 029X 64299 PMC 2996004 PMID 21180450 a b Xylene Archived August 11 2011 at the Wayback Machine Swedish Chemicals Agency apps kemi se 2010 Accessed 2012 4 28 Capturing Opportunities for Para xylene Production UOP A Honeywell Company Retrieved 8 February 2015 SIRI Xylenes Materials Safety Data Sheet MSDS No X2000 Vermont Safety Information Resources Inc 1997 9 8 Accessed 2012 4 27 Clark J E Luthy R V 1955 Separation of Xylenes Ind Eng Chem 47 2 250 253 doi 10 1021 ie50542a028 Stevenson Cheryl D McElheny Daniel J Kage David E Ciszewski James T Reiter Richard C 1998 Separation of Closely Boiling Isomers and Identically Boiling Isotopomers via Electron Transfer Assisted Extraction Analytical Chemistry 70 18 3880 doi 10 1021 ac980221b ICIS Paraxylene Orthoxylene Prices News amp Market Analysis icis com 2012 Accessed 2012 4 28 Bostik Safety Data Sheet Blu Tack Archived September 11 2011 at the Wayback Machine No 13135 Bostik Corp 2007 6 Accessed 2012 4 28 Samet Wendy comp Appendix I Painting Conservation Catalog American Institute for Conservation of Historic and Artistic Works conservation wiki com 1997 9 Accessed 2012 4 28 Cooling baths UC Davis Chem Wiki 2013 10 02 Retrieved 8 February 2015 Cargille John 1985 1964 Immersion Oil and the Microscope New York Microscopical Society Yearbook archived from the original on 2011 09 11 retrieved 2011 03 10 Carson Freida Hladik Christa 2009 Histotechnology A Self Instructional Text 3 ed American Society for Clinical Pathology Press p 35 ISBN 9780891895817 a b c Kandyala Reena Raghavendra Sumanth Phani C Rajasekharan Saraswathi T 2010 01 01 Xylene An overview of its health hazards and preventive measures Journal of Oral and Maxillofacial Pathology 14 1 1 5 doi 10 4103 0973 029X 64299 ISSN 0973 029X PMC 2996004 PMID 21180450 ACUTE TOXICITY SUMMARY XYLENES PDF Archived from the original PDF on October 22 2015 Xylenes EHC 190 1997 Gagnaire F Marignac B Langlais C Bonnet P July 2001 Ototoxicity in rats exposed to ortho meta and para xylene vapours for 13 weeks Pharmacology amp Toxicology 89 1 6 14 doi 10 1034 j 1600 0773 2001 d01 129 x ISSN 0901 9928 PMID 11484912 Gagnaire F Marignac B Blachere V Grossmann S Langlais C 2007 03 07 The role of toxicokinetics in xylene induced ototoxicity in the rat and guinea pig Toxicology 231 2 3 147 158 doi 10 1016 j tox 2006 11 075 ISSN 0300 483X PMID 17210216 Fuente Adrian McPherson Bradley Cardemil Felipe September 2013 Xylene induced auditory dysfunction in humans Ear and Hearing 34 5 651 660 doi 10 1097 AUD 0b013e31828d27d7 hdl 10533 134303 ISSN 1538 4667 PMID 23598724 S2CID 45206975 Draper T H J Bamiou D E April 2009 Auditory neuropathy in a patient exposed to xylene case report PDF The Journal of Laryngology amp Otology 123 4 462 465 doi 10 1017 S0022215108002399 ISSN 1748 5460 PMID 18439334 Fuente Adrian McPherson Bradley Hood Linda J November 2012 Hearing loss associated with xylene exposure in a laboratory worker Journal of the American Academy of Audiology 23 10 824 830 doi 10 3766 jaaa 23 10 7 hdl 10533 137495 ISSN 1050 0545 PMID 23169198 HIPPURIC and METHYL HIPPURIC ACIDS in urine PDF NIOSH Manual of Analytical Methods NMAM Fourth ed a b Inoue O Seiji K Kawai T Watanabe T Jin C Cai S X Chen Z Qu Q S Zhang T Ikeda M 1993 Excretion of methylhippuric acids in urine of workers exposed to a xylene mixture Comparison among three xylene isomers and toluene International Archives of Occupational and Environmental Health 64 7 533 539 doi 10 1007 bf00381104 PMID 8482596 S2CID 21534640 Kira S 1977 Measurement by gas chromatography of urinary hippuric acid and methylhippuric acid as indices of toluene and xylene exposure Occupational and Environmental Medicine 34 305 309 305 309 doi 10 1136 oem 34 4 305 PMC 1008281 PMID 588486 External links EditWikimedia Commons has media related to Xylenes Chisholm Hugh ed 1911 Xylene Encyclopaedia Britannica 11th ed Cambridge University Press NIOSH Pocket Guide to Chemical Hazards o Xylene NIOSH Pocket Guide to Chemical Hazards m Xylene NIOSH Pocket Guide to Chemical Hazards p Xylene Xylene Hazard Summary EPA Mixed Isomers The Ear Poisons The Synergist American Industrial Hygiene Association November 2018 Retrieved from https en wikipedia org w index php title Xylene amp oldid 1053534515, wikipedia, wiki, book,

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