三氯蔗糖-6-乙酸酯的合成及其工艺优化

doi:10.7506/spkx1002-6630-201322021

食品科学 ›› 2013, Vol. 34 ›› Issue (22): 106-110.doi: 10.7506/spkx1002-6630-201322021

三氯蔗糖-6-乙酸酯的合成及其工艺优化

冷一欣，刘晓成，苏继光，张云，武玉真，黄成龙，万屹东

1.常州大学石油化工学院，江苏省绿色催化材料与技术重点实验室，江苏常州 213164；
2.常茂生物化学工程股份有限公司，江苏常州 213034

收稿日期:2013-01-17 修回日期:2013-10-22 出版日期:2013-11-25 发布日期:2013-12-05
通讯作者: 冷一欣 E-mail:rxslyxcn@yahoo.com.cn

Synthesis and Process Optimization of Sucralose-6-acetate

LENG Yi-xin，LIU Xiao-cheng，SU Ji-guang，ZHANG Yun，WU Yu-zhen，HUANG Cheng-long，WAN Yi-dong

1. Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China；2. Changmao Biochemical Engineering Co. Ltd., Changzhou 213034, China

Received:2013-01-17 Revised:2013-10-22 Online:2013-11-25 Published:2013-12-05

摘要/Abstract

摘要：

用SOCl2和N,N-二甲基甲酰胺(DMF)合成Vilsmeier试剂，氯化蔗糖-6-乙酸酯制得三氯蔗糖-6-乙酸酯，并经IR、1H NMR确认其结构。考察投料物质的量比、向反应体系中所添加甲苯的比例、还原反应过程中pH值及氯代温度。结果表明：在80℃条件下最适宜制备Vilsmeier试剂；n(Vilsmeier试剂):n(蔗糖-6-乙酸酯)=11:1，m(甲苯):m(DMF)=1:10，还原反应中pH7.5；反应分3个阶段，一氯代在70℃、二氯代在90℃、三氯代在110℃最适宜进行氯代反应；合成三氯蔗糖-6-乙酸酯收率达到55.7%。

关键词: 蔗糖-6-乙酸酯, 三氯蔗糖-6-乙酸酯, Vilsmeier试剂, 氯代

Abstract:

Sucrose-6-acetate was chlorinated in the presence of Vilsmeier reagent, which was synthesized with SOCl2 and
DMF. The structure of the sucralose-6-acetate obtained was confirmed by IR and 1H NMR. Chlorination temperature, the
molar ratio of reaction substrates, the amount of toluene added and pH in the reduction reaction were optimized. The most
suitable temperature to prepare the Vilsmeier reagent was 80 ℃. The molar ratio of Vilsmeier reagent to sucrose-6-acetate
was 11:1 and mass ratio of toluene to N,N-dimethylformamide was 1:10. The optimized pH was 7.5 in the reduction reaction.
This chlorination reaction was divided into three steps with three chlorination temperatures of 70, 90 ℃ and 110 ℃, respectively.
The yield of sucralose-6-acetate under the optimized reaction conditions was 55.7%.

Key words: sucrose-6-acetate, sucralose-6-acetate, Vilsmeier reagent, chlorination

中图分类号:

TS 202.3

冷一欣，刘晓成，苏继光，张云，武玉真，黄成龙，万屹东. 三氯蔗糖-6-乙酸酯的合成及其工艺优化[J]. 食品科学, 2013, 34(22): 106-110.

LENG Yi-xin，LIU Xiao-cheng，SU Ji-guang，ZHANG Yun，WU Yu-zhen，HUANG Cheng-long，WAN Yi-dong. Synthesis and Process Optimization of Sucralose-6-acetate[J]. FOOD SCIENCE, 2013, 34(22): 106-110.

参考文献

[1] 韦异, 栗晖, 张英等. 柱色谱分离提纯三氯蔗糖[J]. 食品科学, 2002, 29(5): 87-89.

[2] 李鹏飞, 李宗石, 乔卫红. 非营养型甜味剂—三氯蔗糖[J]. 化工进展, 2005, 24(11): 1253-1256.

[3] MUFTI K S, KHAN R A. Process for the preparation of 4,1′,6′-trichloro-4,1′,6′-trideoxy galactose sucrose(TGS):US: 4380476 [P].1983-4-19.

[4] HOUGH L, PHADNIS S P, TARELLI E. The preparation of 4,6-dichloro-4,6-deoxy-6′-chlorodeoxy -β-D-galactose sucrose and the conversion of chlorinated derivation into anhydrides[J]. Carbohydr Res, 1975, 44(1): 37-44.

[5] 郑建仙, 李璇, 袁尔东. 全基团保护法制备三氯蔗糖的研究[J]. 食品与发酵工业, 2002, 33(2): 1-6.

[6] NAVIA J L. Process for synthesizing sucrose derivatives by regioselective reaction: US: 4950746 [P]. 1990-08-21.

[7] 马志玲, 王延平, 彭志英. 单酯法合成高甜度甜味剂—三氯蔗糖的研究[J]. 食品科学, 2002, 23 (5): 51-54.

[8] CLARK J D, LEMAYR R R. Method for the synthesis of sucrose-6-esters: US: 6939962 [P]. 2005-09-6.

[9] 陈金娥. 超级甜味剂三氯蔗糖的开发与研究[J]. 酿酒科技, 2007, 28(2): 29-34.

[10] KHAN R A, SANKEY G H, SIMPSON P J. Chlorination of sugars: US: 5136031 [P]. 1992-08-4.

[11] JONES J D,HACKING A J,CHEETHAM P J. Biological method for protection of 6-position of sucrose and its use in synthesis of disaccharide high-intensity sweeter[J]. Biotech&Bioeng. 1992. 39(2): 203-210.

[12] BENNETT C,DORDICK J S,HACKING A J, et al. Biocatalytic synthesis of disaccharide high-intensity sweeterner sucralose via a tetrachlororaffinose intermediate[J]. Biotech&Bioeng, 1992, 39(2): 211-217.

[13] CLARK J D, et al. An improved method for the synthesis of sucrose-6-esters: EP: 1305326 [P]. 2003-05-2.

[14] WALKUP R E, NAVIA J L, et al. Sucrose-6-ester chlorination: US: 4980463 [P]. 1990-11-25.

[15] 陆正清. 三氯蔗糖合成工艺研究[D]. 南京: 东南大学, 2006.

[16] QUENEAU Y, FITREMANN J, TROMBOTTO S. The chemistry of unprotected sucrose:the selectivity issue[J]. C.R.Chimie, 2004, 7(2): 177-188.

[17] 李晔, 晏日安, 李晓光, 等. 三氯蔗糖的基团迁移法合成研究[J]. 食品科学, 2004, 25(1): 50-52.

[18] 陆正清. 蔗糖-6-乙酸酯氯化工艺的研究[J]. 食品科技, 2007, (3): 158-161.

[19] 张建军. N-N二甲基甲酰胺与甲苯相互作用的1H NMR研究[J]. 河北师范大学学报(自然科学版), 1993, 1: 41-44.

[20] 李松林, 周亚平, 刘俊吉. 物理化学(下册)[M]. 第五版. 北京: 高等教育出版社, 2009: 542-543.

三氯蔗糖-6-乙酸酯的合成及其工艺优化

Synthesis and Process Optimization of Sucralose-6-acetate

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