Study of the O-glycidylation of natural phenolic compounds. The relationship between the phenolic structure and the reaction mechanism |
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Authors: | Chahinez Aouf Christine Le Guernevé Sylvain Caillol Hélène Fulcrand |
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Affiliation: | 1. INRA, UMR 1083 Sciences pour l''?nologie, F-34060 Montpellier, France;2. Montpellier SupAgro, UMR 1083 Sciences pour l''?nologie, F-34060 Montpellier, France;3. Université Montpellier I, UMR 1083 Sciences pour l''?nologie, F-34060 Montpellier, France;4. Institut Charles Gerhardt, UMR CNRS 5253, Equipe Ingénierie et Architecture Macromoléculaire, ENSCM, 34296 Montpellier, France |
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Abstract: | ![]() 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. |
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