甜味剂三氯蔗糖的合成及结构表征.pdf

第23卷第12期
化学研究与应用
Vol 23 No 12
2011年12月
Chemical Research and Application
Dec.,2011
文章编号:1004-1656(2011)12-166605
甜味剂三氯蔗糖的合成及结构表征
冷一欣”,张兆,黄春香,林富荣
(常州大学石油化工学院,江苏常州213164)
摘要:以蔗糖为原料,运用单基团保护法,制备蔗糖6-乙酯,用 Vilsmeier试剂氯代蔗糖6-乙酯制备三氯蔗糖-
6-乙酯,氢氧化钾脱除三氯蔗糖6-乙酯的乙酰基,制得三氯蔗糖。考察了反应物摩尔比、反应温度、反应时间
等对反应的影响。结果表明:蔗糖6-乙酯的最佳合成条件为n(蔗糖):n(原乙酸三乙酯)=1:2.5,0℃反应
4h,收率为70.2%;三氯蔗糖6-乙酯的最佳合成条件为n(蔗糖6-乙酯):n( Vilsmeier)=1:18.5,110℃反应
2h,收率为51.9%;以氢氧化钾为脱乙酰基剂制得三氯熊糖,收率为78.1%,产物结构经IR、HNMR、C
NMR表征分析。
关键词:蔗糖;蔗糖6-乙酯;三氯蔗糖6-乙酯;脱乙酰基剂;三氯蔗糖
中图分类号:0629.12文献标识码:A
Synthesis and characterization of sweetener sucralose
LENG Yi-xin", ZHANG Zhao, HUANG Chun-xiang, LIN Fu-rong
School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
Abstract: Sucrose-6-ester was synthesized by monogroup protected synthesis, using sucrose as the raw material. Sucrose-6-ester was
selective chlorinated by Vilsmeier reagent to obtain sucralose-6-ester. Sucralose was obtained from sucralose-6-ester by deacetyla
tion, using KOH as the deacetylation agent. The effects of the major factors, such as the molar ratio of raw material, reaction tempera
ture and reaction time were systematically studied. The optimum conditions of acet lation were as follows: sucrose-to-triethyl ortho
etate molar ratio was 1: 2. 5, the reaction temperature was 0, and the reaction time was 4h. The yield of sucrose-6-ester was
70.2%. The optimum conditions of conation were as follows: sucrose-6-ester-to-vilsmeier molar ratio was 1: 18. 5, the reaction
temperature was 110, and the reaction time was 2h. The yield of sucralose-6-ester was 51.9%o. Using KOH as the deacetylation a-
gent and the yield of sucralose was 78. 1%. Sucralose was characterized by IR, H NMR and"C NMR.
Key words: sucrose; sucrose-6-ester; sucralose-6-ester; deacetylation agent; sucralose
卤代燕糖衍生物是一类以蔗糖为原料经卤族剂3?。三氯蔗糖的合成方法主要有全基团保护
类元素取代而成的新型甜味剂。其优异的特点法、酶-化学法和单基团保护法1。全基团
是高甜度(34、低熱量、无毒、抗龋。其中又以三保护法合成路线长、原料成本较高、工艺流程复
氯蔗糖最具代表性,化学名为4,1',6-三氯4,1,6-杂、消耗大;酶-化学法投资成本高、产物提纯难;单
三脱氧半乳型蔗糖?,是目前世界上高甜度非营养基团保护法合成路线较短、产率较高。但在单基
性甜味剂开发研究较高水平的产物?,甜度是蔗糖团保护法合成中,合成技术要求高,中间产物蔗糖
的600倍以上,是一种非常具有开发前途的甜味6-乙酯和三氯蔗糖6-乙酯的合成是该合成路线的
收稿日期:201003-21;修回日期:2011-07-12
联系人简介:冷一欣(1961-),女,教授,研究方向:绿色化学品及药物中间体的合成。Emai:rxslyxen(@yahoo.com.cn