Xylene

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File:IUPAC-cyclic.svg
The xylene isomers

A xylene (from Greek ξυλος, xylos, "wood") is an aromatic hydrocarbon consisting of a benzene ring with two methyl substituents. The three isomeric xylenes each have a molecular formula of C8H10, though the more informative semi-structural formula C6H4(CH3)2 is also used commonly. The xylenes are major petrochemicals, produced by catalytic reforming and also by coal carbonisation in the manufacture of coke fuel. Representing about 0.5–1% of crude oil (depending on the source), xylenes are found in small quantities in gasoline and airplane fuels. Xylenes are mainly produced as part of the BTX aromatics (benzene, toluene and xylenes) extracted from the product of catalytic reforming known as "reformate". The mixture is a slightly greasy, colourless liquid commonly encountered as a solvent. It was named in 1851, having been discovered as a constituent of wood tar. Several million tons are produced annually.[1] In 2011, a global consortium began construction of one of the world’s largest xylene plants in Singapore.[2]


The most common xylene application in the oilfield is as solvent for removing asphaltene or wax deposits.

Production

Xylenes are produced by dehydrocyclodimerization and by methylating of toluene and benzene.[1][3] Via the Isomar process, the ratio of isomers can be shifted to favor p-xylene, which is most valued. This conversion is catalyzed by zeolites.[1]

Properties

Xylenes encompass three isomers of dimethylbenzene. The isomers are distinguished by the designations ortho- (o-), meta- (m-), and para- (p-), which specify to which carbon atoms (of the benzene ring) the two methyl groups are attached. Counting the carbon atoms around the ring starting from one of the ring carbons bonded to a methyl group, and counting towards the second methyl group, the o-isomer has the IUPAC name of 1,2-dimethylbenzene, the m-isomer is 1,3-dimethylbenzene, and the p-isomer is 1,4-dimethylbenzene.

Some chemical and physical properties differ from isomer to isomer. The melting point ranges from −47.87°C (m-xylene) to 13.26°C (p-xylene). The boiling point for each isomer is around 140°C. The density of each 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. Xylene in air can be smelled at concentrations as low as 0.08 to 3.7 ppm (parts of xylene per million parts of air) and can begin to be tasted in water at 0.53 to 1.8 ppm.

Xylene Isomers
General
Common name Xylenes o-Xylene m-Xylene p-Xylene
Systematic name Dimethylbenzenes 1,2-Dimethylbenzene 1,3-Dimethylbenzene 1,4-Dimethylbenzene
Other names Xylols 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 0.62 cP at 20°C 0.34 cP at 30°C
Hazards
MSDS Xylenes[4] o-Xylene m-Xylene p-Xylene
EU Classification Harmful (Xn)
NFPA 704
3
0
Flash point 30°C 17°C 25°C 25°C
R/S statement R10, R20/21, R38: (S2), S25
RTECS number ZE2450000 ZE2275000 ZE2625000
Supplementary data page
Structure & properties n, εr, etc.
Thermodynamic data Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
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, 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 90 °C. As with many alkylbenzene compounds, xylenes form complexes with various halocarbons.[5] The complexes of different isomers often have dramatically different properties from each other.[6]

Applications

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 xylene, is consumed in this way.[7][8] 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

Xylene is used as a solvent. In this application, the mixture of isomers is often referred to as xylenes or xylol. Solvent xylene often contains a small percentage of ethylbenzene. Like the individual isomers, the mixture is colorless, sweet-smelling, and highly flammable. Areas of application include printing, rubber, and leather industries. It is a common component of ink, rubber, adhesive,[9] and leather industries. 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.[10] 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 asphaltene and paraffin solvents; used to remove organic deposits in the production or processing systems.

Laboratory uses

It 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.[11] In histology, xylene is the most widely used clearing agent.[12] 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

Although conversion to terephthalic acid is the dominant chemical conversion, xylenes are precursors to other chemical compounds. For instance chlorination of both methyl groups gives the corresponding xylene dichlorides (bis(chloromethyl)benzenes) whilst monobromination yields xylyl bromide, a tear gas-agent used in World War I.

Safety

Xylenes are not highly toxic as indicated by the high values of the LD50, which range from 200 to 4000 mg/kg for animals. The principal mechanism of detoxification is oxidation to methylbenzoic acid and hydroxylation to hydroxylene.[1] However, the material safety data sheet (MSDS) rating assigned is for a moderate hazard, indicating safe handling precautions should include goggles, protective clothing, ventilation, and proper gloves, with storage of the material in a cool, dry, well-ventilated location since it is highly flammable.[4]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 Fabri, Jörg, Graeser, Ulrich, and Simo, Thomas A., Xylenes, Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a28_433.
  2. ↑ Tremblay, Jean-François, Making Aromatics In Singapore, Chem. Eng. News, 89 (38), 2011-9-19, pp 18–19. Accessed 2012-4-28.
  3. ↑ 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.
  4. ↑ 4.0 4.1 SIRI, Xylenes Materials Safety Data Sheet, MSDS No. X2000, Vermont Safety Information Resources, Inc., 1997-9-8. Accessed 2012-4-27.
  5. ↑ Script error
  6. ↑ Stevenson, Cheryl D., McElheny, Daniel J., Kage, David E., Ciszewski, James T., and Reiter, Richard C., "Separation of Closely Boiling Isomers and Identically Boiling Isotopomers via Electron-Transfer-Assisted Extraction", Analytical Chemistry, 70 (18), 1998-8-8, 3880-3885. doi:10.1021/ac980221b
  7. ↑ Xylene, Swedish Chemicals Agency, apps.kemi.se, 2010. Accessed 2012-4-28.
  8. ↑ ICIS, Paraxylene-Orthoxylene | Prices, News & Market Analysis, icis.com, 2012. Accessed 2012-4-28.
  9. ↑ Bostik, Safety Data Sheet Blu-Tack, No. 13135, Bostik Corp., 2007-6. Accessed 2012-4-28.
  10. ↑ 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.
  11. ↑ Cargille, John (1964 (revised 1985)), "Immersion Oil and the Microscope", New York Microscopical Society Yearbook, http://www.cargille.com/immersionoilmicroscope.shtml
  12. ↑ Script error

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