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2,2,6,6-四甲基哌啶氧自由基/Ca(ClO)2催化氧化甲基葡糖苷制备葡醛酸

马彦,赵林林,刘华庆,袁华*,吴元欣   

  1. (武汉工程大学, 绿色化工过程省部共建教育部重点实验室,湖北省新型反应器与绿色化学工艺重点实验室 武汉 430073)
  • 收稿日期:2011-06-20 修回日期:2011-09-08 出版日期:2012-05-10 发布日期:2012-05-10
  • 通讯作者: 袁华,教授; Tel:027-87194980; Fax:027-87195671; E-mail:yuanhua@mail.wit.edu.cn; 研究方向：有机合成化学
  • 基金资助:
    国家自然科学基金(20936003)湖北省自然科学基金(2010CDB11106)资助项目

Preparation of Glucuronic Acid by Selective Oxidation of Methyl Glucoside with 2,2,6,6-Tetramethylpiperidinyloxy/Ca(ClO)2

MA Yan, ZHAO Linlin, LIU Huaqing, YUAN Hua*, WU Yuanxin   

  1. (Key Laboratory for Green Chemical Process of Ministry of Education,Hubei Key Laboratory of Novel
    Chemical Reactor and Green Chemical Technology,Wuhan Institute of Technology,Wuhan 430073,China)
  • Received:2011-06-20 Revised:2011-09-08 Published:2012-05-10 Online:2012-05-10

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摘要： 采用2,2,6,6-四甲基哌啶氧自由基/Ca(ClO)-2体系选择氧化甲基葡萄糖苷（简称甲苷）合成了葡萄糖甲苷酸盐，再用硫酸酸解葡萄糖甲苷酸盐，得到葡萄糖醛酸和副产物硫酸钙。 考察了氧化工艺条件对葡萄糖醛酸收率的影响；用pH计监控反应过程，反应中间体和终产物用UV和HPLC检测。 结果表明，该体系对甲苷伯羟基的氧化具有较好的催化活性和反应选择性，葡萄糖醛酸收率达到92%，且金属离子易于去除。 和传统的淀粉HNO3氧化法工艺相比，该方法具有资源节约、环境友好的特点。

关键词: 四甲基哌啶氧自由基/Ca(ClO)2催化体系, 甲基葡萄糖苷, 葡萄糖醛酸, 选择氧化

Abstract: Glycoside acid salt was prepared by selective oxidation from methyl glucoside with  2,2,6,6-tetramethylpiperidinyloxy（TEMPO）/Ca(ClO)2 system. Glucuronic acid and by-products calcium sulfate were obtained by following-up acidification and hydrolization with 2 mol/L H2SO4. The effects of catalytic oxidation conditions on the yield of glucuronic acid were studied. The reaction process was monitored by measuring the pH value of reaction system, the intermediate and products were determined by UV and HPLC. The results showed that the TEMPO/Ca(ClO)2 system had high activity and good selectivity for the catalytic oxidation of glycoside with a 92% yield of glucuronic acid, and Ca2+ ion in the reaction system can be easily removed. Comparing to traditional technology of HNO3 oxidation, this process is more environmental-friendly and conserves more resources.

Key words: tetramethylpiperidinyloxy/Ca(ClO)2 system, methyl glucoside, glucuronic acid, selective oxidation

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