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Synthesis of trichloro-cane-6-ethyl ester

A technology of sucralose and synthesis method, which is applied in the direction of chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of excessive DMF, environmental pollution, and unavailability, and achieve simple operation, high yield, and low toxicity. low effect

Inactive Publication Date: 2007-01-17
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the inert solvent that it adopts is poisonous substances such as benzene, toluene, carbon tetrachloride, and the DMF in this invention wherein is greatly excessive and can't be utilized, easily pollutes the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] The ratio of the amount of feed materials is sucrose-6-ethyl ester: bis(trichloromethyl) carbonate=3:7; the volume weight of tertiary amine containing N-formyl group and bis(trichloromethyl) carbonate Ratio (ml / g) = 1:1, the feeding amount of sucrose-6-ethyl ester is 5g (0.013mol), the feeding amount of bis(trichloromethyl)carbonate is 10g (0.030mol), containing N-formyl The tertiary amine of the group is N,N-dimethylformamide, the amount is 10ml, and the volume of tetrahydrofuran for dissolving sucrose-6-ethyl ester and bis(trichloromethyl)carbonate is 10ml each.

[0015] Put the tertiary amine containing N-formyl group into a 100ml four-necked flask equipped with mechanical stirring, thermometer, reflux condenser, water separator, and constant pressure dropping funnel. The temperature of the system was reduced to 0°C in an ice salt bath, and the tetrahydrofuran solution of bis(trichloromethyl)carbonate was added dropwise. Control the reaction temperature not to exceed 5°C...

Embodiment 2

[0017] The ratio of the amount of feed material is sucrose-6-ethyl ester: bis(trichloromethyl) carbonate = 1:3; the volume weight of tertiary amine containing N-formyl group and bis(trichloromethyl) carbonate Ratio (ml / g) = 1:1, the feeding amount of sucrose-6-ethyl ester is 10g (0.026mol), and the feeding amount of bis(trichloromethyl) carbonate is 23g (0.078mol), containing N-methyl The tertiary amine of the acyl group is N,N-dimethylformamide, the dosage is 23ml, and the volume of tetrahydrofuran for dissolving sucrose-6-ethyl ester and bis(trichloromethyl)carbonate is 20ml each. Other operations are the same as in Example 1. Concentrated and crystallized on a rotary evaporator to obtain the product (6.64g, 0.015mol) with a molar yield of 58%.

Embodiment 3

[0019] The ratio of the amount of feed material is sucrose-6-ethyl ester: bis(trichloromethyl) carbonate = 1:2; the volume weight of tertiary amine containing N-formyl group and bis(trichloromethyl) carbonate Ratio (ml / g) = 1:1, the feeding amount of sucrose-6-ethyl ester is 5g (0.013mol), the feeding amount of bis(trichloromethyl)carbonate is 10g (0.03mol), containing N-formyl The tertiary amine of the group is N,N-dimethylformamide, the amount is 10ml, and the volume of tetrahydrofuran for dissolving sucrose-6-ethyl ester and bis(trichloromethyl)carbonate is 10ml each. Other operations are the same as in Example 1. The crystallization was concentrated on a rotary evaporator to obtain the product (3.10 g, 0.0071 mol) with a molar yield of 54.4%.

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PUM

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Abstract

Synthesis of trichloro-cane sugar-6-ethyl ester is carried out by dissolving carbonic ether into butylene oxide, dripping tertiary containing N-formoly at 0-5degree to obtain Vilsmeier reagent, dripping butylene oxide solution containing cane sugar-6-ethyl ester at 0-5degree, reacting at 110-120degree for 4-6hrs, regulating reactive liquid by alkali liquor to neutralization, extracting by ethyl acetate, de-coloring by active carbon, and re-crystallizing to obtain trichloro-cane sugar-6-ethyl ester crystal. The proportion of carbonic ether and tertiary containing N-formoly is 1:4-5. It is simple, safe, has no environmental pollution and higher purity. It can be used for industrial production.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing sucralose-6-ethyl ester, a key intermediate for preparing food sweetener sucralose. (2) Background technology [0002] Sucralose (sucralose, molecular formula C 12 H 19 O 8 Cl 3 , Molecular weight 397.64) is a low-energy high-sweetness sweetener, its sweetness is 600-800 times that of sucrose. It is formed by replacing the three hydroxyl groups at positions 4, 1', and 6'with chlorine atoms in the sucrose molecule. The key process of sucralose synthesis is the synthesis of its intermediate sucralose-6-ethyl ester. There are 8 hydroxyl groups in the sucrose molecular structure, and its relative reactivity is 6 and 6'>4>1'>2>3 , 3', 4'. To prepare sucralose-6-ethyl ester, the 6-hydroxyl group of sucrose must be protected and then used for selective chlorination. [0003] In the preparation of sucralose, all synthetic routes involve a chlorination step. Chlorination is a key issue in the synthes...

Claims

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Application Information

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IPC IPC(8): C07H13/02C07H5/02
Inventor 苏为科陈志卫陈运强陈炯明王艳丽
Owner ZHEJIANG UNIV OF TECH
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