Occidental Chemical Corporation

Hooker Chemicals & Plastics Corporation

Byron R Cotter

David Y Tang

Henry C Lin

Frederick J Goetz

Fredrick J Goetz

James J Maul

Joseph A Pawlak

Frederick J Goetz, Sr

A process for the preparation of pentahaloethoxy benzoyl halide compounds comprising

Process for the preparation of pentahaloethoxy benzoyl halide compounds

4,4-dihalohexahydrophthalic anhydrides of the formula ##STR1## where Y is chlorine or fluorine, are prepared by the reaction of hydrogen fluoride with 4-chlorotetrahydrophthalic anhydride. The 4,4-dihalohexahydrophthalic anhydrides of this invention can be dehydrohalogenated by reaction with basic alumina to prepare a mixture of 4-fluorotetrahydrophthalic anhydride isomers of the formula ##STR2## The 4-fluorotetrahydrophthalic anhydrides can then be dehydrogenated by reaction with a dehydrogenation catalyst to prepare 4-fluorophthalic anhydride.

4,4-dihalohexahydrophthalic anhydrides and 4-fluorotetrahydrophthalic

A process for the preparation of 3-chloro-4-fluoro-5-nitrobenzotrifluoride and 3,4-difluoro-5-nitrobenzotrifluoride by reaction of 3,4-di-chloro-5-nitrobenzotrifluoride and 4-chloro-3,5-dinitrobenzotrifluoride, respectively, with an alkali metal fluoride.

3,4-difluoro-5-nitrobenzotrifluoride and preparation of

Diphenyl ethers of the formula ##STR1## wherein m is 1-3, n is 1 or 2, R is hydrogen, carboxy, carboxylate salt or ester, formyl oxime, cyano, alkyl, alkoxy, chloro, bromo, or N, N-dialkyl amino, are prepared by reacting a chloro-fluoro-benzotrifluoride of the formula ##STR2## wherein m and n are as defined above with a nitro-phenoxide of the formula ##STR3## where R is defined above, and M is a cation of an alkali metal or an alkaline earth metal.

Method for the preparation of nitrodiphenyl ethers

Chloro-aromatic compounds of the formula ##STR1## wherein 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; q+m+n is less than 6; and when q is 1, m is 2; are prepared by the vapor phase chloro-denitration reaction of a chlorinating agent with a nitro-aromatic compound of the formula ##STR2## where R, m, n and q are as defined above.

3-chloro-4-fluoro-5-nitrobenzotrifluoride

Trifluoromethylbenzoyl chlorides or bromides are prepared by contacting trichloromethylbenzoyl chlorides or tribromomethylbenzoyl bromides with trifluoromethylbenzoyl fluorides in the presence of a halogen transfer catalyst.

Process for the preparation of trifluoromethylbenzoyl chlorides and

Trifluoromethylbenzoyl chlorides are prepared by the reaction of trichloromethylbenzoyl chlorides or tribromomethylbenzoyl bromides with about 3 moles or less of hydrogen fluoride in the presence of a halogen transfer catalyst.

Preparation of trifluoromethyl-benzoyl halides

A method for the preparation of aromatic amines comprises reacting hydrogen fluoride with a phenyl carbamic fluoride.

Method for the preparation of benzenamines

Chloro-aromatic compounds of the formula ##STR1## wherein R is CF.sub.3, OCF.sub.3, OC.sub.2 F.sub.5, CN, NCO, or COCl, m is 0 or 1, and n is 0 or 1 are prepared by the vapor phase chloro-denitration reaction of a chlorinating agent with a nitro-aromatic compound of the formula ##STR2## where R, m, and n are as defined above.

Preparation of nuclear chlorinated aromatic compounds

Diphenyl esters of the formula ##STR1## wherein R is hydrogen, carboxy, carboxylate salt or ester, formyl, cyano, alkyl, alkoxy, chloro, bromo, or N, N-dialkyl amino, are prepared by reacting a chloro-fluoro-benzotrifluoride with a nitro-phenoxide of the formula ##STR2## where R is defined above, and M is a cation of an alkali metal or an alkaline earth metal.

A method for the preparation of a 2-(trifluoromethyl)phenyl carbamic fluoride comprises isomerizing N-(trifluoromethyl)-anthraniloyl fluoride in the presence of hydrogen fluoride to 2-(trifluoromethyl)phenyl carbamic fluoride.

Method for the preparation of 2-(trifluoromethyl)phenyl carbamic fluoride

A method and a useful catalyst composition for the production of aromatic nitriles for the corresponding nuclearly halogenated aromatic compounds which contain from 1 to 4 halogen atoms substituted selected from chlorine, bromine and iodine are described. The method involves the steps of heating the halogenated aromatic compound to a temperature of at least 100.degree. C. for a period of at least 2 hours in the presence of potassium cyanide and a catalyst composition comprised of:

Process for the preparation of aromatic nitriles

A process for the separation of 2,6-dichlorobenzaldehyde from an isomeric mixture of dichlorobenzaldehyde comprises dissolving the isomeric mixture in a water-immiscible organic solvent, contacting the solvent with an aqueous sodium bisulfite solution, separating the aqueous solution and recovering 2,6-dichlorobenzaldehyde from the organic solvent.

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Grand Island, NY, United States of America

Byron R Cotter