o-Xylene

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o-Xylene
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Template:Longitem 67796
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UN number 1307
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance Colorless liquid
Density 0.88 g/ml
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Solubility in ethanol very soluble
Solubility in diethyl ether very soluble
Vapor pressure 7 mmHg (20°C)[2]
Template:Longitem −77.78·10−6 cm3/mol
Template:Longitem 1.50545
Viscosity 1.1049 cP at 0 °C
0.8102 cP at 20 °C
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Explosive limits 0.9%-6.7%[2]
Template:Longitem 100 ppm[4] (TWA), 150 ppm[4] (STEL)
Template:Longitem m-xylene
p-xylene
toluene

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o-Xylene (ortho-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2, with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of m-xylene and p-xylene, the mixture being called xylene or xylenes. o-Xylene is a colourless slightly oily flammable liquid.[7]

Production and use

Petroleum contains about one weight percent xylenes. Most o-xylene is produced by cracking petroleum, which affords a distribution of aromatic compounds, including xylene isomers. m-Xylene is isomerized to o-xylene. Net production was approximately 500,000 tons in the year 2000.

o-Xylene is largely used in the production of phthalic anhydride, which is a precursor to many materials, drugs, and other chemicals.[7] Related to their easy oxidation, the methyl groups are susceptible to halogenation. When treated with elemental bromine, these groups are brominated, yielding xylylene dibromide:[8]

C6H4(CH3)2 + 2 Br2 → C6H4(CH2Br)2 + 2 HBr

Toxicity and exposure

Xylenes are not acutely toxic, for example the LD50 (rat, oral) is 4300 mg/kg. Effects vary with animal and xylene isomer. Concerns with xylenes focus on narcotic effects.[7]

References

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  5. ↑ O-xylene toxicity
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