Occidental Chemical Corporation

George Piotrowski

Sanjay K Mandal

Kevin R Benson

John Hickey

Michael J Fifolt

William S Derwin

Robert L Bell

James Franc

Disclosed is a method for making high purity .alpha.-chloroxylenes. A composition is formed of about 15 to about 80 wt % of a xylene and about 20 to about 85 wt % of a solvent. The solvent can be toluene, ring halogenated toluene, benzotrichloride, ring halogenated benzotrichloride, benzotrifluoride, ring halogenated benzotrifluoride, .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-hexafluorometaxylene, .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-hexafluoroparaxylene, or a mixture thereof. The composition is heated to about 70 to about 160.degree. C. No base is present in the composition. Chlorine gas is sparged through the composition and chlorine free radicals are generated therein. The chlorine free radicals can be generated either with UV light or by means of a chlorine free radical initiator.

Method of making .alpha.-chloroxylenes

Disclosed is a method of preparing an aromatic compound having the general formula ##STR1## where R is CF.sub.3, OCF.sub.3, OC.sub.2 F.sub.5, CN, NCO, or COCl, m is 0, 1, or 2, n is 0, 1, or 2, q is 1 or 2, and q+m+n is an integer from 1 to 5. A vapor is prepared of a substrate having the general formula ##STR2## and a chlorinating agent. The mixture is reacted at a temperature above the boiling point of the substrate but below its decomposition temperature. The amount of chlorinating agent is about 0.5 to about 2 times the amount stoichiometrically required to replace the nitro groups on the substrate with chlorine. Unreacted substrate and partially reacted substrate are condensed from the product mixture and are recycled. The substrate is preferably in contact with the chlorinating agent before it is vaporized.

Preparation of nuclear chlorinated aromatic compounds

Disclosed is a method of chlorinating a side chain of a aromatic or heterocyclic ether. The aromatic or heterocyclic ether is mixed with a fluorine-containing aliphatic solvent. The aromatic or heterocyclic ether is contacted with chlorine radical at an elevated temperature which results in its chlorination. The chlorinated product is preferably insoluble in the solvent and separates, forming two phases. The solvent phase can be recycled and reused.

Side chain chlorination of aromatic and heterocyclic ethers

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Cheektowaga, NY, United States of America

George Piotrowski