o-Xylene
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.[1]
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.[1] Related to their easy oxidation, the methyl groups are susceptible to halogenation. When treated with elemental bromine, these groups are brominated, yielding xylylene dibromide:[2]
- 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.[1]
References
- ↑ a b c Template:Ullmann
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