Abstract
A series of new alkyl-glycidyl esters of dicarboxylic acids which could be used as PVC plasticizers were synthesized. The method adopted is a new synthetic process which can be carried out in two stages. During the first stage, the carboxylic acid anhydride reacts with the salt of the alcohol, and the sodium salt produced reacts with epichlorhydrin in the presence of a catalyst to yield an alkyl-glycidyl ester. The specific reactions give pure products in high yields. The reaction of phthalic acid bisodium salt with epichlorhydrin, as well as the reaction of phthaloyl chloride with glycidol, gave diglycidyl phthalate in 36% and 22% yields, respectively.
Similar content being viewed by others
References
Zlatanos, S.N., A.N. Sagredos and V.P. Papageorgiou,J. Am. Oil Chem. Soc. 62:1575 (1985).
Kester, E.B., C.J. Gaiser and M.E. Lazar,J. Org. Chem. 8:550 (1943).
Maerker, G., E.J. Saggese and W.S. Port,J. Am. Chem. Soc. 38:194 (1961).
Otsubo, K., K. Waki and K. Senda,Japan 68 18:522 (1969).
Heilman, W.J.,U.S.A. 3 661:938 (1972).
Katsurada, H., H. Masaharu and S. Yutaka,Japan. Kokai 75 76:012 (1976).
Georgescu, M.,Rom. RO 78:510 (1983).
Bacus, C.L., D.P. Sandru and U.H. Hedwig,84:820 (1985).
Maerker, G., J.F. Carmichael and W.S. Port,J. Org. Chem. 26:2681 (1961).
Zondler, H., D. Trachsler and F. Lohse,Ger. Offen. 2:602, 157 (1976).
Chizh, G.K., N.K. Moshchinskaya and V.S. Olifer,U.S.S.R. 405:880 (1974).
Heer, A., and W. Schaffner,Ger. Offen. 2:027, 568 (1971).
Mearker, G., J. Garmichael and W. Port,J. Org. Chem. 2681 (1961).
Sorokin M.F., L.G. Shode, A.I. Kuz'Min and A.G. Ruchkina,Viniti 5439:81 (Russ) (1983).
Ritz, J., H. Hotze and H. Mummenthey,Ger. Offen. 2:907, 997 (1980).
Sugawara, Y., H. Naito, S. Nakamura and N. Maruyama,Jpn. Tokkyo Koho 80 04:333 (1980).
Massy, D.J.R.,Brit. 1:172, 743 (1970).
Sugawara, Y., H. Naito, S. Nakamura and N. Maruyama,Jpn. Kokai 128:650 (1978).
Kuleshova, I.D., Va. L. Raskin, L.A. Mirkind, A.G. Kornienko and G.M. Klyachko,U.S.S.R. 757:571 (1980).
Author information
Authors and Affiliations
About this article
Cite this article
Zlatanos, S.N., Sagredos, A.N. A new method of synthesis of alkyl-glycidyl esters of dicarboxylic acids in high yields. J Am Oil Chem Soc 67, 661–664 (1990). https://doi.org/10.1007/BF02540418
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02540418