Study of the O-glycidylation of natural phenolic compounds. The relationship between the phenolic structure and the reaction mechanism

被引：66
作者：
Aouf, Chahinez [1 ,2 ,3 ]
Le Guerneve, Christine [1 ,2 ,3 ]
Caillol, Sylvain [4 ]
Fulcrand, Helene [1 ,2 ,3 ]
机构：
[1] INRA, UMR Sci Oenol 1083, F-34060 Montpellier, France
[2] Montpellier SupAgro, UMR Sci Oenol 1083, F-34060 Montpellier, France
[3] Univ Montpellier I, UMR Sci Oenol 1083, F-34060 Montpellier, France
[4] Inst Charles Gerhardt, CNRS, UMR 5253, Equipe Ingn & Architecture Macromol,ENSCM, F-34296 Montpellier, France
来源：
TETRAHEDRON | 2013年 / 69卷 / 04期
关键词：
Natural phenolic compounds; O-glycidylation; Reactivity; Mechanism; Bio-based epoxy resin pre-polymers; LIQUID-PHASE; BISPHENOL-A; POLYPHENOLS; KINETICS; LIGNIN; POLYMERS; RESIN;
D O I：
10.1016/j.tet.2012.11.079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The O-alkylation reaction by epichlorohydrin of some natural phenolic compounds such as 4-methylcatechol, gallic acid, protocatechuic acid, pyrogallol and resorcinol was investigated. Phenolic compounds reacted first with epichlorohydrin in the presence of benzyltriethylammonium chloride as phase transfer catalyst. Then, an aqueous solution of sodium hydroxide was added. It was demonstrated that the two competitive mechanisms involved in the O-alkylation reaction were highly dependent of the starting material. The O-alkylated products obtained in this reaction could be further used as bisphenol A substitutes in the synthesis of epoxy resins pre-polymers. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1345 / 1353
页数：9
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