Occidental Chemical Corporation

Hooker Chemicals & Plastics Corporation

James J Maul

David Y Tang

Henry C Lin

Richard D Carlson

Arthur M Foster

Lawrence B Fertel

Byron R Cotter

Bobby F Dannels

Victor A Pattison

Karl W Seper

Garra C Lester

Disclosed are novel compounds having the formula ##STR1## where A is O or NR, each R' independently selected from hydrogen, R, or M, R is alkyl, aryl, alkaryl, or aralkyl from C.sub.1 to C.sub.12, and M is a cation. Also disclosed is a method of making those compounds and a method of making a mixture of 3,5-difluorobenzoic acid and 1,3-difluorobenzene by reacting 3,5-dichlorophthalic anhydride with a fluorinating agent to produce 3,5-difluorophthalic anhydride, reacting the 3,5-difluorophthalic anhydride with water to produce 3,5-difluorophthalic acid, and decarboxylating the 3,5-difluorophthalic acid.

Difluorophthalic compounds and their preparation

Novel halogenated trifluoromethylbenzenes have the structural formula ##STR1## wherein X is halogen, preferably Cl, F or Br, and R is a group selected from the group consisting of --COOH, --C(O)NH.sub.2 and --CN. These compounds are intermediates for pesticidal trifluoromethyl diphenyl ethers and are converted thereto by replacing the fluorine para to the trifluoromethyl with substituted phenoxy group in aromatic nucleophilic substitution. A novel intermediate which is converted by reaction with cuprous cyanide and HONO to compound having the above structural formula where X is F and R is --CN is 2,3-difluoro-5-(trifluoromethyl)aniline and has the formula ##STR2##

Halogenated trifluoromethylbenzenes

p-Trifluoromethyl benzaldehydes are prepared by the catalytic reduction reaction of p-trifluoromethyl benzonitriles with hydrogen in an aqueous formic acid media in the presence of a nickel/aluminum alloy catalyst.

Catalytic reduction of nitriles to aldehydes

A process for the preparation of pentahaloethoxy benzoyl halide compounds comprising

Process for the preparation of pentahaloethoxy benzoyl halide compounds

A process for the preparation of 3-chloro-4,5-difluorobenzonitrile comprising the steps of

Process for the preparation of halo aromatic compounds

A process is disclosed for purifying and stabilizing a mixture of regular chlorotrifluoroethyelne telomers of formula RCXCl(CF.sub.2 CFCl).sub.n Br from bromine-containing irregular telomer impurities of similar molecular weight. The telomer mixture is produced by reacting chlorotrifluoroethylene with a telogen of formula RCXClBr, where R is CF.sub.2 Br, or Cl, and X is Cl or F. The telomer mixture is then chlorinated using either elevated temperature alone (100.degree. C.-350.degree. C.), or a combination of elevated temperatures (100.degree. C.-200.degree. C.) and light energy primarily of the wavelength region greater than about 3000.degree.A. Under these conditions, CFClBr telomer end group of the regular or normal telomer is chlorinated to form --CFCl.sub.2 end groups, while the bromine-containing irregular telomer impurities (whose bromine-containing end groups are substantially only --CF.sub.2 Br) are substantially not chlorinated. The desired regular telomers can then be readily separated from the higher boiling impurities by distillation. Any --CF.sub.2 Br groups present in the isolated regular telomer are then further stabilized by prolonged chlorination under the above conditions or at elevated temperatures (100.degree. C.-350.degree. C.) with irradiation by a UV lamp.

Selective chlorination of chlorotrifluoroethylene telomers

A process for the preparation of high purity 5-chloroisophthaloyl chloride comprises reacting isophthaloyl chloride with liquid chlorine in the presence of a Lewis acid catalyst at a temperature of about 55.degree. Celsius to 80.degree. Celsius under autogenous pressure.

Synthesis of high purity 5-chloroisophthaloyl chloride

A process for the preparation of chloro-difluorobenzene compounds of the formula ##STR1## where R is CN or CF.sub.3, comprises the steps of (A) reacting an alkali metal fluoride with 4-chloro-3,5-dinitrobenzonitrile or 4-chloro-3,5-dinitrobenzotrifluoride to form the corresponding 4-fluoro-3,5-dinitrobenzonitrile or 4-fluoro-3,5-dinitrobenzotrifluoride product.

A process for the preparation of meta-substituted diaryl ethers comprises reacting an ortho-haloaryl compound with a phenol compound in a non-aqueous medium in the presence of an alkaline metal base. In a specific embodiment m-phenoxytoluene is prepared by reacting orthochlorotoluene with phenol in the presence of an alkaline metal hydroxide in a substantially non-aqueous liquid medium.

Preparation of meta-substituted diaryl ethers

Halogenated derivatives of the Diels-Alder adducts of norbornenes and halocyclopentadienes are excellent fire retardant additives for polymers free of nitrogen in the monomeric units of the polymer chain, the additive-containing polymers being characterized by exceptional heat stability; excellent mechanical properties and improved molding characteristics.

Halogen containing fire retardant additive with improved heat stability

A process for the preparation of compounds of the formula

Liquid phase fluorination process

Halogenated derivatives of the Diels-Alder adducts of norbornenes and halocyclopentadienes are excellent fire retardant additives for polymers, which additives are characterized by exceptional heat stability.

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Grand Island, NY, United States of America

James J Maul