Occidental Chemical Corporation

Sanjay K Mandal

Kevin R Benson

Michael J Fifolt

William S Derwin

George Piotrowski

John Hickey

James Franc

Disclosed is a method of making an &agr;-chloro-&agr;,&agr;-difluoro aromatic compound. An &agr;,&agr;,&agr;-trichloro aromatic compound having the general formula

Method of making &agr;-chloro-&agr;,&agr;-difluoro 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 removing a soluble antimony compound from a liquid in which it is dissolved. The liquid is contacted with a hydrated compound, particularly a hydrated compound that forms carbonate ions, bicarbonate ions, or both in the liquid, such as carbonic acid or hydrates of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonium carbonate, or ammonium bicarbonate. An antimony compound is formed that is insoluble in the liquid and it is separated from the liquid.

Method of purifying liquid products by removing soluble antimony

Disclosed is a method of fluorinating a substrate having the general formula ##STR1## where each R is independently selected from halogen, alkyl from C.sub.1 to C.sub.12, aryl from C.sub.6 to C.sub.12, alkoxide from C.sub.1 to C.sub.12, aryloxide from C.sub.6 to C.sub.12, nitro, amino, alkylamino from C.sub.1 to C.sub.12, and arylamino from C.sub.6 to C.sub.12, each X is independently selected from halogen and at least one X is chlorine or bromine, each m is independently selected from 0 to 5, n is 0 or 1, p is 0 or 1, q is 0 or 1, and n+p+q is 1. The substrate is heated to a temperature of about 40 to about 100.degree. C. and is reacted with a fluorinating agent in the presence of about 0.05 to about 2 wt % molybdenum trioxide. The composition of the substrate, the catalyst, and the fluorinating agent is also disclosed.

Molybdenum trioxide catalyzed fluorination reactions

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 preparing brominated substituted anilines. A mixture in water is formed of a substituted aniline having the general formula ##STR1## where each R is independently selected from halogen, alkyl and haloalkyl from C.sub.1 to C.sub.12, aryl, alkaryl, and aralkyl from C.sub.6 to C.sub.12, R does not occupy all three 2, 4, and 6 positions, and n is 1 to 4. To the suspension is added about 1.0 to about 1.1 equivalents of bromine for each bromine atom to be substituted onto the aromatic ring of said substituted aniline. No acid is present during the reaction.

Method of preparing brominated substituted anilines

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.

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Grand Island, NY, United States of America

Sanjay K Mandal