Abstract: Disclosed is a method of isolating the aromatic product formed when a substrate having the general formula is dehalogenated, forming a product mixture of copper salts and aromatic product, where X is the halogen removed from the substrate to form the aromatic product, R′ is COOH, COOR, COR, CN, COH(R)2, or SO3H, each R″ is independently selected from halogen, R, or OR or two vicinal R″ groups form one or more fused aromatic rings, R is alkyl from C1 to C18 or aryl from C6 to C18, and n is 1 to 4. Water in an amount about 1 to about 5 times the amount of the substrate is added to the product mixture, forming an organic phase that contains the aromatic product and an aqueous phase that contains the copper salts. If the density of the organic phase differs from the density of said aqueous phase by less than 0.1 g/cc, a suitable solvent is added to the product mixture in an amount sufficient to increase the differences between the organic and aqueous phases to at least 0.

Abstract: Disclosed is a method of separating the meta isomer of a haloalkylbenzene having the general formula from a mixture with at least one other isomer, where X is Cl or Br and R is alkyl from C2 to C12 or cycloalkyl from C3 to C8. About 0.0001 to about 5 wt % of a Friedel-Crafts catalyst is added to the mixture and the mixture is exposed to a brominating agent which preferentially brominates the meta isomer. The mixture is then heated at a temperature above the boiling point of the other isomers but below the boiling point of the brominated meta isomer.

Abstract: 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° C.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 3,4,6-trifluorophthalic acid is prepared in high yield by reaction of a 3,4,6-trichloro-N-substituted phthalimide with potassium fluoride at temperatures in the range of 200.degree. to 270.degree. C. in the absence of a catalyst to form the corresponding trifluoro-N-substituted phthalimide which, in turn, is hydrolyzed to form the 3,4,6-trifluorophthalic acid.

Abstract: Disclosed is a method of making 3-methoxy-2,4,5-trifluorobenzoic acid. A tetrafluorophthalimide is reacted with an alkali metal hydroxide to produce a mixture of alkali metal salts of 4-hydroxy-3,5,6-trifluoro-N-alkylphthalamic acid and 3-hydroxy-2,4,5-trifluoro-N-alkylbenzamide. Those products are reacted with a methylating agent to produce 4-methoxy-3,5,6-trifluoro-N-alkylphthalamic acid and 3-methoxy-2,4,5-trifluoro-N-alkylbenzamide. Those products are reacted with an acid to produce 4-methoxy-3,5,6-trifluorophthalic acid and 3-methoxy-2,4,5-trifluorobenzoic acid. Finally, the 4-methoxy-3,5,6-trifluorophthalic acid is reacted with a decarboxylating agent to produce additional 3-methoxy-2,4,5-trifluorobenzoic acid.

Abstract: A process for the selective hydrodefluorination of a tetrafluorophthalimide compound of the formula ##STR1## where X is 1 and R is a monovalent organo group; or X is 2 and R is a divalent organo group; comprises reacting (I) the tetrafluorophthalimide with zinc in an aqueous alkali metal hydroxide medium. The product may be hydrolyzed to form 3,4,6-trifluorophthalic acid.

Abstract: 3,4,6-Trifluorophthalic acid may be decarboxylated in a controlled manner to form 2,4,5-trifluorobenzoic acid by heating the phthalic acid in a dipolar aprotic solvent in the absence of any catalyst.

Abstract: Disclosed is a method of making 3-hydroxy-2,4,5-trifluorobenzoic acid. A aqueous solution is prepared of an alkali metal base and a tetrafluorophthalimide. The solution is heated to produce a mixture of a salt of a 4-hydroxy-3,5,6-trifluorophthalamic acid and a salt of a 3-hydroxy-2,4,5-trifluorobenzamide. The solution is neutralized with acid to form a precipitate of the 4-hydroxy-3,5,6-trifluorophthalamic acid and the 3-hydroxy-2,4,5-trifluorobenzamide. The precipitate is reacted with a mineral acid to produce 3-hydroxy-2,4,5-trifluorobenzoic acid.

Abstract: Disclosed is a method of selectively removing chlorine atoms in the order of fifth position first, fourth position second, and third position third from a chlorophthalic compound having at least two ring chlorine atoms such as a chlorophthalic acid or a chlorophthalic anhydride. The chlorophthalic compound is reacted in solution with a hydrodechlorinating metal in the presence of a base.

Abstract: It has been discovered that 3,4,6-trifluorophthalic anhydride may be decarboxylated by heating in a polar aprotic solvent to yield 2,4,5-trifluorobenzoic acid.