Synthesis method of trichloro-cane-6-ethyl ester

A technology for sucralose and a synthesis method, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve problems such as unavailability, excessive DMF, environmental pollution, etc., and achieves simple operation, high yield, and toxicity. low effect

Inactive Publication Date: 2008-07-16
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 feeding material is sucrose-6-ethyl ester: two (trichloromethyl) carbonate=3: 7; the volume weight of the tertiary amine containing N-formyl group and two (trichloromethyl) carbonate Ratio (ml / g)=1:1, the dosage of sucrose-6-ethyl ester is 5g (0.013mol), the dosage of bis(trichloromethyl)carbonate is 10g (0.030mol), containing N-formyl The tertiary amine of the group is N,N-dimethylformamide, and its consumption is 10ml, and the volumes of tetrahydrofuran dissolved in sucrose-6-ethyl ester and bis(trichloromethyl)carbonate are each 10ml.

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

Embodiment 2

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

Embodiment 3

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

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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 synthesis method of the key intermediate sucralose-6-ethyl ester 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 whose sweetness is 600-800 times that of sucrose. It is formed by replacing the three hydroxyl groups at the 4, 1', and 6' positions of the sucrose molecule with chlorine atoms. 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 of sucrose must be protected, and then selectively chlorinated with sucralose. [0003] In the preparation of sucralose, all synthetic routes involve the chlorination step, which is a key issue i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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