维生素E的催化合成路线分析
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摘要
维生素E具有多种特异的生理活性,同时也是一种优良的抗氧化剂,已经逐渐成为维生素领域中的焦点,市场需求不断增加。目前合成维生素E占据市场的80%以上,提升维生素E的产量和生产效率势在必行。天然维生素E包括四种生育酚类物质和四种生育三烯酚类物质,其中α-生育酚含量最大,生理活性也最高。本综述简要介绍α-生育酚的合成路线,其中包括2,3,5-三甲基氢醌和异植物醇的合成以及它们二者缩合的反应。本文着重阐述路线的设计和催化剂的选择,并对存在的问题及潜在的解决办法进行评述和展望。
Vitamin E compounds are biologically active and are frequently used as antioxidants.The demand for Vitamin E compounds has increased significantly in recent years,and at present,more than 80% of the market demand for Vitamin E is fulfilled by its synthetic counterparts.Therefore,it is imperative to increase the production of Vitamin E.Vitamin E compounds contain tocopherol and tocotrienol derivatives,and α-tocopherol,which dominates the sound,is the most biologically active.This review covers the methods of preparation of α-tocopherol,focusing on the synthesis routes,chemical reactions,and corresponding catalysts.The synthesis of Vitamin E,including preparation of2,3,5-trimethylhydroquinone(TMHQ),preparation of isophytol,and condensation of TMHQ and isophytol are discussed in detail.The disadvantages and issues related to the preparation methods are also included.In general,the preparation of TMHQ comprises three steps:(1) methylation of m-cresol to 2,3,6-trimethylphenol,(2) oxidation of 2,3,6-trimethylphenol to 2,3,5-trimethylbenzoquione(TMBQ),and(3) hydrogenation of TMBQ to TMHQ.Recently,a novel and attractive method using isophorone,which can be produced by self-condensation of acetone,as a source for synthesizing TMHQ has been developed.Among these procedures,it is important to attain high selectivity in the oxidative reactions,including oxidation of 2,3,6-trimethylphenol and isophorone(α-isophorone or β-isophorone),and to replace H2 O2,a common oxidant,by oxygen or air.One of the methods of preparation of isophytol using citral as a source has been abandoned because of shortage of oil of litsea cubeba,which is a natural source of citral.Linalool,produced from 6-methyl-5-hepten-2-one,is a key intermediate in the main process of preparation of isophytol.Both BASF SE and Roche have developed effective methods for the preparation of 6-methyl-5-hepten-2-one,respectively.Semi-hydrogenation of alkynols plays a key role in the whole process.The selectivity,especially at high conversion is directly related to the profit;therefore,it is of great importance for industries.The condensation of TMHQ and isophytol is essentially a Friedel-Crafts alkylation reaction catalyzed by acids.Similar reactions include methylation of m-cresol.Bronsted acids are usually effective for these reactions;however,it is difficult to recover these catalysts from the homogeneous systems.Therefore solid acid has a great potential in this area and it is also a promising topic to reduce the loss of acid sites when using acid-immobilized catalysts.The supply of various sources of the reactants and the local policy need to be considered while choosing an appropriate method for the preparation of Vitamin E.
Vitamin E compounds are biologically active and are frequently used as antioxidants.The demand for Vitamin E compounds has increased significantly in recent years,and at present,more than 80% of the market demand for Vitamin E is fulfilled by its synthetic counterparts.Therefore,it is imperative to increase the production of Vitamin E.Vitamin E compounds contain tocopherol and tocotrienol derivatives,and α-tocopherol,which dominates the sound,is the most biologically active.This review covers the methods of preparation of α-tocopherol,focusing on the synthesis routes,chemical reactions,and corresponding catalysts.The synthesis of Vitamin E,including preparation of2,3,5-trimethylhydroquinone(TMHQ),preparation of isophytol,and condensation of TMHQ and isophytol are discussed in detail.The disadvantages and issues related to the preparation methods are also included.In general,the preparation of TMHQ comprises three steps:(1) methylation of m-cresol to 2,3,6-trimethylphenol,(2) oxidation of 2,3,6-trimethylphenol to 2,3,5-trimethylbenzoquione(TMBQ),and(3) hydrogenation of TMBQ to TMHQ.Recently,a novel and attractive method using isophorone,which can be produced by self-condensation of acetone,as a source for synthesizing TMHQ has been developed.Among these procedures,it is important to attain high selectivity in the oxidative reactions,including oxidation of 2,3,6-trimethylphenol and isophorone(α-isophorone or β-isophorone),and to replace H2 O2,a common oxidant,by oxygen or air.One of the methods of preparation of isophytol using citral as a source has been abandoned because of shortage of oil of litsea cubeba,which is a natural source of citral.Linalool,produced from 6-methyl-5-hepten-2-one,is a key intermediate in the main process of preparation of isophytol.Both BASF SE and Roche have developed effective methods for the preparation of 6-methyl-5-hepten-2-one,respectively.Semi-hydrogenation of alkynols plays a key role in the whole process.The selectivity,especially at high conversion is directly related to the profit;therefore,it is of great importance for industries.The condensation of TMHQ and isophytol is essentially a Friedel-Crafts alkylation reaction catalyzed by acids.Similar reactions include methylation of m-cresol.Bronsted acids are usually effective for these reactions;however,it is difficult to recover these catalysts from the homogeneous systems.Therefore solid acid has a great potential in this area and it is also a promising topic to reduce the loss of acid sites when using acid-immobilized catalysts.The supply of various sources of the reactants and the local policy need to be considered while choosing an appropriate method for the preparation of Vitamin E.
引文
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