Process for preparation of .beta.-hydroxy esters by reaction of organic carboxylic acids and vicinal epoxides
AssigneeThe Dow Chemical Company
InventorArthur E. Gurgiolo
Life of this patent
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Abstract
A synergistic catalytic effect is realized in the esterification reaction between an organic carboxylic acid and a vicinal epoxide by using a catalyst system comprising: (a) a compound containing an amino and/or ammonium nitrogen atom, in combination with (b) a soluble compound containing an ionizable atom of iron or chromium.
Claims16
In the process of preparing a .beta.-hydroxyester comprising reacting by contacting an organic carboxylic acid and a vicinal epoxide at a temperature between about 60.degree. C and 130.degree. C, the improvement comprising conducting said process in the presence of a catalytic amount of a catalytic composition comprising:
- (a) a first catalytic compound having at least one amino or ammonium nitrogen atom and selected from the group consisting of ammonia, ethylenediamine, diethylenetriamine, alkylamine, dialkylamine, trialkylamine, trialkanolamine, dialkylarylamine, diarylalkylamine, triarylamine, triaralkylamine, trialkarylamine, dialkylaralkylamine, dialkylalkarylamine, 5- or 6-membered heterocyclic aliphatics which include amino nitrogen within the ring, pyridine, a cross-linked ion-exchange resin bearing a plurality of tertiary amine or quaternary ammonium sites, and tetraalkyl ammonium halides, in combination with (b) a second catalytic compound, which is soluble in each of said acid and epoxide reactants, having an ionizable atom of iron or chromium and is selected from the group consisting of iron halides, chromium halides, ferric alkanoate of 1 to 12 carbon atoms, ferric sulfate, ferric nitrate, ferric alkoxides, and ferric acrylate or methacrylate;
- the mole ratio of (a) to (b) being from 1:10 to 10:1.
A process for preparing a bis(.beta.-hydroxyalkyl) ester of an aromatic dicarboxylic acid which comprises reacting said aromatic dicarboxylic acid with a 1,2-alkylene oxide in the presence of (a) a catalyst selected from the group consisting of amines and quaternary ammonium salts, and (b) at least one iron compound which is soluble in each of said aromatic dicarboxylic acid and 1,2-alkylene oxide reactants.
Dependencies are inferred from the claim text.