A kind of preparation method of sucrose-6-acetate

A technology of acetate and sucrose, applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of inconvenient post-treatment of catalysts, many reaction steps, and high cost

Active Publication Date: 2021-06-29
WANHUA CHEM GRP CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The trimethyl orthoacetate method has the unfavorable factors of high cost and low yield, and the organotin method has the unfavorable factors of high toxicity of organotin reagents
[0004] Patents US005470969A, CN109575090A, and CN104817597A refer to the method of using dibutyltin oxide catalyst to catalyze sucrose and acetic anhydride to prepare sucrose-6-acetate. This method produces more waste solvents, solvent recovery is troublesome and energy consumption is high, and at the same time Organotin reagents are troublesome to deal with and highly toxic
[0005] Patents CN101041676A and CN105254684A mention that sucrose and trimethyl orthoacetate undergo esterification reaction under the catalysis of p-toluenesulfonic acid, add water for hydrolysis reaction, then add organic amine for conversion reaction, and finally distill to obtain sucrose-6-acetate However, there are many reaction steps, low selectivity, troublesome post-processing, and high cost.
[0006] Patent CN101693729A mentions that sucrose reacts with excess ethyl acetate to obtain sucrose-6-acetate under the action of carbonate and benzyltriethylamine chloride as a catalyst. The reaction temperature is high, the operation is troublesome, and the cost is high.
[0007] In view of the deficiencies in the above-mentioned processes, it is urgent to develop a novel preparation method of sucrose-6-acetate to overcome the current production problems of large environmental pollution, low selectivity, troublesome post-treatment of catalysts, and energy consumption of solvent recovery. advanced questions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example

[0035] Catalyst 1:

[0036] 83.2g of potassium tetrachloroplatinate, 99.3g of N-hydroxyphthalimide were mixed in 500g of distilled water, 158.5g of biboronic acid pinacol ester was mixed in 1000g of distilled water, and then the two solutions were mixed and Raise the temperature to 30°C and stir for 1 hour; add 99.3g of neutral alumina and mix under stirring to obtain slurry A;

[0037] Heat the slurry A and the alkaline precipitant B (30wt% sodium carbonate solution) to 30°C respectively, and slowly add the alkaline precipitant B to the slurry A until the pH of the system is 8, and control the reaction temperature of the precipitation process to 30°C ; Then aging at 70°C for 2h to obtain the slurry;

[0038] The slurry was filtered, washed with deionized water to obtain a filter cake, and the filter cake was dried at 100°C for 5 hours, then calcined at 400°C for 15 hours, crushed and pressed into tablets to obtain Catalyst 1.

[0039] After ICP analysis, it is determined th...

Embodiment 1

[0057] Catalyst 1 (102.7 g) was added to a round bottom flask equipped with a mechanical stirrer, thermocouple and dropping funnel, then the flask was heated to about 30°C. Sucrose (684.6g, 2mol) and 1-acetyl-1H-1,2,3-triazol[4,5-B]pyridine (389.2g, 2.4mol) were dissolved in 3423g DMF, and the solution was dissolved in about Add dropwise to the round bottom flask over 3 hours while maintaining the reaction temperature at about 30°C using an external cooling bath. After the addition was complete, the reaction mixture was stirred for a further 6 hours. The solid catalyst was removed by filtration, the reaction liquid was separated, the solvent DMF was distilled off from the reaction liquid, and the obtained crude product was thermally crystallized in methanol to obtain the product sucrose-6-acetate as a white solid.

Embodiment 2

[0059] Catalyst 2 (41.1 g) was added to a round bottom flask equipped with a mechanical stirrer, thermocouple and dropping funnel, and the flask was heated to about 40°C. Sucrose (342.3g, 1mol) and 1-acetyl-1H-1,2,3-triazol[4,5-B]pyridine (243.2g, 1.5mol) were dissolved in 1027g DMAC, and the solution was dissolved in about The round bottom flask was added dropwise over 2 hours while maintaining the reaction temperature at about 40°C using an external cooling bath. After the addition was complete, the reaction mixture was stirred for a further 5 hours. The solid catalyst was removed by filtration, the reaction solution was separated, the solvent DMAC was removed from the reaction solution, and the obtained crude product was thermally crystallized in methanol to obtain the product sucrose-6-acetate as a white solid.

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Abstract

The invention discloses a preparation method of sucrose-6-acetate. Under the action of a supported platinum catalyst, sucrose and 1-acetyl-1H-1,2,3-triazol[4,5-B]pyridine Esterification occurs with high selectivity to generate sucrose-6-acetate, and the product is separated by crystallization in solution; the supported platinum catalyst is expressed as Pt / X / Z-Y, wherein X is selected from N-hydroxyl-ortho Phthalimide, 1-Hydroxybenzotriazole, N-Hydroxymaleimide, N-Hydroxysuccinimide, 2,2,6,6-Tetramethylpiperidine Oxide, Y It is selected from neutral alumina, silica, molecular sieve, kaolin, and Z is selected from pinacol diborate, biscatechol borate, diphenyltetramethylsilane, and hexamethylsilane. The process of the invention avoids the problems of the use of highly toxic reagents and difficulty in solvent recovery in the prior art, and the conversion rate of raw materials and product selectivity can reach more than 90%.

Description

technical field [0001] The invention relates to a production method of sucrose-6-acetate, in particular to a production method of sucrose and 1-acetyl-1H-1,2,3-triazol[4,5-B]pyridine through the esterification reaction The method for sucrose-6-acetate belongs to the field of chemical technology. [0002] technical background [0003] The food additive industry has always needed a novel method for preparing sweetener molecules. Sucralose is a new type of sweetener first developed by the British Taylor Company. It is the only functional sweetener using sucrose as a raw material. The sweetness is 600 times that of sucrose. Sucrose-6-acetate is an important intermediate for the synthesis of sucralose. The current industrialized methods are trimethyl orthoacetate method and organotin method. The trimethyl orthoacetate method has the disadvantages of high cost and low yield, and the organotin method has the disadvantage of high toxicity of organotin reagents. [0004] Patents US...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/04C07H1/00B01J31/22B01J35/10
CPCB01J31/1691B01J35/1023B01J35/1028B01J35/1042B01J2231/49B01J2531/0238B01J2531/828C07H1/00C07H13/04
Inventor 刘杰张静郭斌任一臻陈来中张永振
Owner WANHUA CHEM GRP CO LTD
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