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US 4,381,406 AGranted
Process for making allylic esters of tetrachlorophthalic acid
AssigneeFMC Corporation
InventorJoseph H. Finley
Life of this patent
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Abstract
Allylic esters of tetrachlorophthalic acid are formed using allylic alcohol both as a reactant and a solvent. In the first step, the alcohol and a base are reacted with tetrachlorophthalic anhydride to form the half-ester sodium salt. In the second step, the sodium salt is reacted with allylic halide to form the diester which crystallizes from solution. The excess solvent may be treated to recover the raw materials or recycled.
Claims17
The method of producing a diallylic ester of tetrachlorophthalic acid comprising the steps of:
- (a) forming a salt of the monoallylic ester of tetrachlorophthalic acid by reacting tetrachlorophthalic anhydride with
- (i) a sufficient excess of allylic alcohol, over the amount to form the said monoallylic ester, to comprise at least part of a solvent to maintain in solution or suspension the said salt formed in (a), and
- (ii) a sufficient amount of a base to form said salt,
- (b) adding to the product of step (a) a sufficient amount of an allylic halide to convert the salt of the monoallylic ester to the diester of tetrachlorophthalic acid and heating to accelerate the reaction,
- (c) cooling the solution produced in step (b) to crystallize the said allylic diester of tetrachlorophthalic acid from solution, and
- (d) separating the thus-created allylic diester of tetrachlorophthalic acid from the remaining solvent.
3 more elements
The method of producing diallyl tetrachlorophthalate comprising the steps of:
- (a) forming the sodium salt of monoallyl tetrachlorophthalate by heating tetrachlorophthalic anhydride with allyl alcohol at a temperature of about 90.degree. -95.degree. C. in the presence of a sufficient amount of sodium carbonate to form the sodium salt of the monoallyl tetrachlorophthalate which is produced and in the presence of a catalytic amount of triethylamine, said allyl alcohol being present in an amount of at least 10 moles per mole of tetrachlorophthalic anhydride, the excess allyl alcohol acting as a solvent for the reactants,
- (b) adding to the product of step (a) sufficient allyl chloride to convert the sodium salt of monoallyl tetrachlorophthalate to diallyl tetrachlorophthalate and heating in a closed vessel to a temperature of about 100.degree. C.-110.degree. C. until the diallyl ester is formed, and
- (c) cooling the product of step (b) to crystallize the diallyl tetrachlorophthalate from solution in the excess allyl alcohol.
Dependencies are inferred from the claim text.