Occidental Chemical Corporation

Hooker Chemicals & Plastics Corporation

Michael J Fifolt

William S Derwin

Arthur M Foster

Michael C Savidakis

Sanjay K Mandal

David Y Tang

Ronald F Spohn

Mohan Singh Saran

Michael C Hausladen

Donald H Campbell

David C Johnson

Kevin R Benson

Charles M Cook

Daniel R Thielen

John Hickey

John Forcucci

Lawrence B Fertel

Bobby F Dannels

Mary K Cocoman

Viesturs Lesins

Mark E Lindrose

James G Colson

Victor F Cooke

Rudolph F Mundhenke

Walter M Opalinski

Arthur H Morth

William L Rueter

George Piotrowski

Frank P Bermel

F Howard Day

James Franc

Disclosed is a method of isolating the aromatic product formed when a substrate having the general formula

Isolation of products from selective dehalogenation of haloaromatics

Disclosed is a method of separating the meta isomer of a haloalkylbenzene having the general formula

Reducing meta content of isomeric mixtures of halo substituted alkylbenzenes

Ring halogenation of aromatic compounds

Disclosed is a method of making 3,5-dichloro-p-toluoyl chloride. A mixture is prepared of methyl-3,5-dichloro-4-methylbenzoate, about 1 to about 1.4 equivalents of an &agr;,&agr;,&agr;-trichloromethylbenzene, and about 0.01 to about 0.2 equivalents of a catalyst selected from the group consisting of ammonium septamolybdate, ammonium dimolybdate, and mixtures thereof. The mixture is heated to a temperature of about 150 to about 180&deg; C.

Method of making 3,5-dichloro-p-toluoyl chloride

Disclosed is a method of halogenating the ring of an aromatic compound. The aromatic compound is contacted with a halogenating agent in the presence of a heterogeneous catalyst. The catalyst is the calcination reaction product of:

Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst and about 0.001 to about 0.1 equivalents of an iodine-containing cocatalyst at a temperature of ambient to about 100.degree. C.

Chlorination and bromination of aromatic compounds at atmospheric

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 process for making an .alpha.,.alpha.,.alpha.-trifluoromethoxybenzene by reacting an .alpha.,.alpha.,.alpha.-trichloromethoxybenzene or an .alpha.,.alpha.,.alpha.-tribromomethoxybenzene with gaseous hydrogen fluoride in the presence of a catalyst of antimony pentachloride, molybdenum pentachloride, molybdenum dichloride dioxide, molybdenum oxide, or a mixture thereof. The hydrogen fluoride is used in an amount of about 1 to about 1.4 times stoichiometric and is at about atmospheric pressure. The reaction is performed at about 30 to about 100.degree. C.

Method of making trifluoromethoxybenzenes

Disclosed is a method of making trichloromethoxybenzene. A mixture is prepared of anisole and a source of chlorine free radicals, such as chlorine or sulfuryl chloride. The reaction is performed in a solvent, which can be either benzotrifluoride, orthochlorobenzotrifluoride, metachlorobenzotrifluoride, parachlorobenzotrifluoride, or dichlorobenzotrifluoride. The mixture is exposed to actinic radiation, such as ultraviolet light, which generates the chlorine free radicals.

Method of making trichloromethoxybenzene

Telomers are prepared by reacting chlorotrifluoroethylene with 1,2-dibromo-2-chlorotrifluoroethane (CBrClFCF.sub.2 Br) in the presence of a redox catalyst system comprising a metal halide selected from the group consisting of FeCl.sub.3, FeBr.sub.3, CuBr.sub.2, CuCl.sub.2, TiCl.sub.4, VCl.sub.3, and NiCl.sub.2, and a reducing agent selected from the group consisting of Fe, Ni, Cu, Ti, V and benzoin. The preferred catalyst system is ferric chloride and nickel. The telomers of this invention have the structural formula ##STR1## where n is in the range of 1 to 10, and are useful for preparing non-flammable hydraulic fluids.

Telomers prepared from chlorotrifluoroethylene and

A process for the electrophilic ring fluorination of aromatic compounds which comprises reacting a fluorinating agent from the group consisting of CF.sub.3 OF and CF.sub.2 (OF).sub.2 with an aromatic compound of the formula ##STR1## where X is selected from the group consisting of ##STR2## and ##STR3## and Y is selected from the group consisting of --H, --CF.sub.3, --CN, --NO.sub.2, --Cl, and CH.sub.3.

Electrophilic fluorination of aromatic compounds

Non-flammable hydraulic fluids which are particularly useful for replacing existing hydraulic fluids in hydraulic systems employing acrylonitrile-butadiene rubber and fluoroelastomer seals are disclosed. The non-flammable hydraulic fluids of the present invention comprise a fluorinated chlorotrifluoroethylene oil, a refined naphthenic oil, a phenolic antioxidant, a sulfur corrosion inhibitor, a metal deactivator, and an aliphatic ester. The fluorinated chlorotrifluoroethylene oil is present in an amount of at least about 75% by volume of the hydraulic fluid. In addition to being non-flammable, such hydraulic fluids are compatible with both the seals and brass components which contact the hydraulic fluid in hydraulic systems.

Non-flammable hydraulic fluids

Telomers formed by reacting chlorotrifluoroethylene with fluoroxytrifluoromethane are disclosed. The telomerization reaction is conducted in either liquid chlorotrifluoroethylene without a solvent or in solution. The telomers thus formed can optionally be fluorinated by reaction with a suitable fluorinating agent to improve their stability.

Preparation of chlorotrifluoroethylene telomers with

A telomerization process comprises reacting chlorotrifluoroethylene with bisfluoroxydifluoromethane. The telomerization reaction is conducted in either liquid chlorotrifluoroethylene without a solvent or in solution. The telomers thus formed can optionally be fluorinated by reaction with a suitable fluorinating agent to improve their stability.

Non-flammable hydraulic fluids which are particularly useful for replacing existing hydraulic fluids in hydraulic systems employing acrylonitrile-butadiene rubber and Viton or PNF seals are disclosed. The non-flammable hydraulic fluids of the present invention comprise a fluorinated chlorotrifluoroethylene oil, an aliphatic ester, a liquid polyester or polyether, a hydrocarbon oil having a low wax content, and a phenolic antioxidant. The chlorotrifluoroethylene oil is present in an amount of at least about 75% by volume of the hydraulic fluid. Such hydraulic fluids are useful in applications where the flammability of existing fluids poses a significant risk of combustion or explosion due to the possibility of leakage of the fluid from the hydraulic system.

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Grand Island, NY, United States of America

Michael J Fifolt