New one-pot syntheses of ketals and acetals from oleic acid

被引：6

作者：

Godard, Anais ^{[1
,2
]}

Thiebaud-Roux, Sophie ^{[1
,2
]}

De Caro, Pascale ^{[1
,2
]}

Vedrenne, Emeline ^{[1
,2
]}

Mouloungui, Zephirin ^{[1
,2
]}

机构：

[1] Univ Toulouse, INPT ENSIACET, LCA, ENSIACET, F-31030 Toulouse, France

[2] INRA, UMR CAI 1010, F-31030 Toulouse, France

来源：

INDUSTRIAL CROPS AND PRODUCTS | 2014年 / 52卷

关键词：

Hydrogen peroxide; Oleic acid; Acetal; Ketal; Supported catalysis; Tungstophosphoric acid; ISOPROPYLIDENE DERIVATIVES; HYDROGEN-PEROXIDE; OXIDATION;

D O I：

10.1016/j.indcrop.2013.10.011

中图分类号：

S2 [农业工程];

学科分类号：

0828 ;

摘要：

Ketals derived from unsaturated fatty acids, such as oleic acid (OA), are widely used as intermediates in the synthesis of various polymers, biologically active compounds and other high-value derivatives. We propose the study of new conditions for one-pot syntheses of ketals and acetals from oleic acid, using acetone or different alcohols as both reactant and solvent. OA was oxidized in a batch reactor in the presence of hydrogen peroxide (H2O2, 30%) as an oxidant and a peroxo-tungsten anion supported on resin as the catalyst. We investigated the influence of several parameters of this process, using 9,10-dihydroxyoctadecanoic acid as the target molecule. The best operating conditions resulted in an OA conversion above 80%, with a good yield (60%) obtained for the OA/H2O2/{PO4[WO(O-2)(2)](4)}(3-) system supported on a resin, at 70 degrees C for 16 h in acetone. The hydroxyl moiety was oxidized, generating the corresponding aldehyde derivative, when alcohols were used as the solvent. (C) 2013 Elsevier B.V. All rights reserved.

引用

页码：111 / 117

页数：7

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