CONVENIENT SELECTIVE MONOACYLATION OF 1,N-DIOLS CATALYZED BY ION-EXCHANGE RESINS

被引：40

作者：

NISHIGUCHI, T ^{[1
]}

FUJISAKI, S ^{[1
]}

ISHII, Y ^{[1
]}

YANO, Y ^{[1
]}

NISHIDA, A ^{[1
]}

机构：

[1] YAMAGUCHI UNIV,FAC ENGN,DEPT CHEM ENGN & APPL CHEM,UBE,YAMAGUCHI 755,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 05期

关键词：

D O I：

10.1021/jo00084a043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several 1,n-diols, ranging from 1,2-ethanediol to 1,16-hexadecanediol, were selectively monoacylated by transesterification in ester/octane solvent mixtures catalyzed by strongly acidic ion-exchange resins. This method of selective esterification is quite simple and practical. The selectivity for monoester formation and initial rates of monoester formation depended on the ester/octane ratio of the solvents. The reasons for the selectivity are as follows: (1) The sulfonic acid-type ion-exchange resins usually contain 50-80% water, and a strongly acidic aqueous layer is formed on the surface of the resins. (2) A partition equilibrium between the aqueous layer and the aprotic ester/octane layer is setup, and diols have higher partition coefficients than the product monoesters. (3) Acylation of the alcohols occurs in the aqueous layer and/or at the interface between the aqueous and the nonaqueous liquid layer. (4) The formed monoesters move away from the aqueous layer into the aprotic layer.

引用

页码：1191 / 1195

页数：5

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