Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of preparation method of sucrose-6-acetate

A technology of trimethyl orthoacetate and sucrose, which is applied in the field of food sweetener intermediates, can solve the problems of greatly increased DMF usage, DMF loss, and high production costs, and achieve lower production costs, reduced consumption, and high conversion rates Effect

Active Publication Date: 2019-01-01
ZHEJIANG NHU CO LTD
View PDF9 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the continuous vacuum removal of water in this production method, on the one hand, the energy consumption is seriously wasted; on the other hand, too much DMF is taken out in the continuous distillation, and the loss of DMF is obvious, and additional solvent needs to be added in the subsequent reaction, resulting in a large increase in the use of DMF and high production costs.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 80.0g (0.234mol) sucrose and 600ml DMF into a 1000ml three-neck flask, stir, heat to 75°C to dissolve the sucrose completely, cool down to 55°C, add 22.4g (0.187mol) trimethyl orthoacetate and 0.32g para Toluenesulfonic acid, keep warm for 1h. After testing, the mass percentage of methanol in the system is about 0.5%. Then vacuumize under the condition of -0.098MPa, recover DMF50ml. After testing, the mass percentage of methanol in the system is about 0.08%. Add 6.6 g of trimethyl orthoacetate, and continue the heat preservation reaction for 0.5 h. Lower the reaction temperature to 30°C, add 37g of water, and react for 1h. Then add 1.2g of tert-butylamine and 37g of water, and react at 30°C for 3h. After recovering most of the solvent, a syrupy liquid was obtained, which was detected by HPLC and contained 76.4 g (0.199 mol) of sucrose-6-acetate, with a molar yield of 85.0%.

Embodiment 2

[0030] Add 80.0g (0.234mol) sucrose and 600ml DMF into a 1000ml three-neck flask, stir, heat to 75°C to dissolve the sucrose completely, cool down to 55°C, add 23.9g (0.199mol) trimethyl orthoacetate and 0.48g para Toluenesulfonic acid, keep warm for 0.5h. After testing, the mass percentage of methanol in the system is about 0.6%. Then vacuumize under the condition of -0.099MPa to recover DMF40ml. After testing, the mass percentage of methanol in the system is about 0.1%. Add 5.6 g of trimethyl orthoacetate, and continue the heat preservation reaction for 0.5 h. Lower the reaction temperature to 30°C, add 37g of water, and react for 1h. Then add 1.2g of tert-butylamine and 37g of water, and react at 30°C for 3h. After recovering most of the solvent, a syrupy liquid was obtained, which was detected by HPLC and contained 74.9 g (0.195 mol) of sucrose-6-acetate, with a molar yield of 83.3%.

Embodiment 3

[0032] Add 80.0g (0.234mol) sucrose and 600ml DMF into a 1000ml three-neck flask, stir, heat to 75°C to dissolve the sucrose completely, cool down to 60°C, add 25.3g (0.211mol) trimethyl orthoacetate and 0.48g para Toluenesulfonic acid, keep warm for 0.5h. After testing, the mass percentage of methanol in the system is about 0.7%. Then vacuumize under the condition of -0.099MPa, recover DMF80ml. After testing, the mass percentage of methanol in the system is about 0.05%. Add 2.6 g of trimethyl orthoacetate, and continue the heat preservation reaction for 1 h. Lower the reaction temperature to 30°C, add 37g of water, and react for 1h. Then add 1.2g of tert-butylamine and 37g of water, and react at 30°C for 3h. After recovering most of the solvent, a syrupy liquid was obtained, which was detected by HPLC and contained 71.9 g (0.187 mol) of sucrose-6-acetate, with a molar yield of 79.9%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of sucrose-6-acetate. In an existing method, some reaction processes are complicated, the purity and the yield of sucrose-6-ester are low, and production cost is high. The preparation method comprises the following steps: dissolving sucrose into organic solvent; in the presence of p-toluenesulfonic acid, adding trimethyl orthoacetate which is equivalent to 70 to 95 percent of molar weight of the sucrose, and starring at the temperature of 50 to 65DEG C for reacting; removing methanol generated by reacting through adopting intermittent vacuumizing, and supplementing a small amount of trimethyl orthoacetate for continuously reacting until the reaction is finished; after the reaction is complete, adding a proper amount of water for hydrolyzing to generate sucrose-4-ester and the sucrose-6-ester, then adding a proper amount of tert-butylamine and water for converting the sucrose-4-ester into the sucrose-6-ester. The preparation method disclosed by the invention has the advantages that the conversion rate of the sucrose is high, the utilization rate of the trimethyl orthoacetate is high, the purity and the yield of sucrose-6-ester are high, and the cost of a subsequent product, namely sucralose is reduced.

Description

technical field [0001] The invention relates to a food sweetener intermediate, in particular to a preparation method of sucrose-6-acetate. Background technique [0002] Sucralose, also known as sucralose, or TGS for short, is a high-intensity sweetener that can be used in a variety of foods and beverages. Sucrose-6-acetate is an important intermediate in the synthesis of sucralose, which is obtained by protecting the 6-carboxyl group of sucrose with a suitable group protecting agent. At present, the methods for synthesizing sucrose-6-acetate mainly include orthoester method and dibutyltin oxide method. [0003] US4889928 discloses a preparation method of sucrose-6-acetate, which utilizes the reaction of sucrose and trimethyl orthoacetate to generate sucrose-4,6-cyclic ester, and adds water to open the ring to generate sucrose-4-ester and sucrose-6- ester, followed by conversion of sucrose-4-ester to sucrose-6-ester under alkaline conditions. In this method, since sucrose ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/06C07H1/00
Inventor 王晓军车来宾王昌泽晏文武曹家明
Owner ZHEJIANG NHU CO LTD