Green synthesis method of sucralose-6-acetate

A green synthesis, sucralose technology, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve difficult problems such as processing, and achieve the effect of convenient post-processing, high yield and high purity

Pending Publication Date: 2019-06-18
JK SUCRALOSE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Traditional Vilsmeier salts can be prepared by reacting thionyl chloride, phosgene, solid phosgene, etc. with DMF (N,N-dimethylformamide). However, a large a

Method used

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  • Green synthesis method of sucralose-6-acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In 2.5 moles of 1,4-dioxane, add 0.5 moles of DMF and 0.5 moles of phthaloyl chloride, react at 40°C for 3 hours, the generated Vilsmeier salt precipitates, and is filtered and dried to obtain a white solid Vilsmeier salt. Yield 98%.

[0024] Add 9 moles of Vilsmeier salt to 4000 mL of 1,1,2-trichloroethane solvent to make a suspension, then add dropwise to the pre-synthesized 1 mole of sucrose-6-acetate dry syrup, control the temperature below 0°C and stir. After the dropwise addition, the temperature was naturally raised to room temperature, and then slowly raised to 113° C. over 10 hours, and kept for 2.5 hours. After the reaction was completed, the crude product of sucralose-6-acetate was obtained through neutralization, solvent removal, water dissolution, decolorization and crystallization, with a yield of 94%. The liquid chromatogram of this crude product sees figure 1 .

Embodiment 2

[0026] In 4 moles of tetrahydrofuran, 0.5 moles of DMF and 0.5 moles of 3-chlorophthaloyl chloride were added and reacted at 30°C for 4 hours. The resulting Vilsmeier salt precipitate was filtered and dried to obtain white solid Vilsmeier salt with a yield of 98%.

[0027] Add 8 moles of Vilsmeier salt to 4000 mL of DMF solvent to make a solution, then dropwise add it to the pre-synthesized 1 mole of sucrose-6-acetate dry syrup, control the temperature below 0°C and stir. After the dropwise addition, the temperature was naturally raised to room temperature, and then slowly raised to 110° C. over 12 hours, and kept for 1.5 hours. After the reaction was completed, the crude product of sucralose-6-acetate was obtained through neutralization, solvent removal, water dissolution, decolorization and crystallization, with a yield of 92%.

Embodiment 3

[0029] In 3 moles of methyl tert-butyl ether, add 0.5 moles of DMF and 0.5 moles of 3,5-dimethylphthaloyl chloride, and react at 45°C for 2.5 hours. The resulting Vilsmeier salt precipitate is filtered and dried to obtain a white solid Vilsmeier salt, yield 97%.

[0030] Add 10 moles of Vilsmeier salt to 4000 mL of toluene solvent to make a suspension, then add dropwise to the pre-synthesized 1 mole of sucrose-6-acetate dry syrup, control the temperature below 0 ° C and stir. After the dropwise addition, the temperature was naturally raised to room temperature, and then slowly raised to 115° C. over 8 hours, and kept for 3 hours. After the reaction was completed, the crude product of sucralose-6-acetate was obtained through neutralization, solvent removal, water dissolution, decolorization and crystallization with a yield of 90%.

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Abstract

The invention discloses a green synthesis method of sucralose-6-acetate. The green synthesis method comprises the steps that step 1, benzene ring substituted phthaloyl chloride and DMF are adopted toreact in a non-polar organic solvent to generate Vilsmeier salt; step 2, the Vilsmeier salt and sucrose-6-acetate are chloridized in a polar organic solvent to obtain the product sucralose-6-acetate.The green synthesis method of the sucralose-6-acetate has the advantages that no sulfur dioxide gas is released in the reaction, the problem that tail gas sulfur dioxide and hydrogen chloride gas aredifficultly separated in a traditional process is avoided, the difficulty of tail gas treatment is greatly reduced, and the method is a novel green chlorination process; the separation purity of the Vilsmeier salt is high, and the reaction yield is high; acid anhydride produced during the preparation of the Vilsmeier salt can be rechlorinated to generate acyl chloride to be recycled, thereby reducing the production cost; the chlorination process is simpler in operation, more convenient in post-treatment and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of pharmaceutical chemical synthesis and relates to a green synthesis method of sucralose-6-acetate. Background technique [0002] The production of sucralose includes three steps of esterification, chlorination and deacylation, among which the most critical step to determine product yield, quality, cost, etc. is the chlorination reaction of Vilsmeier salt. Preparation of Vilsmeier salt can use thionyl chloride, phosgene, solid phosgene, etc. to react with DMF (N, N-dimethylformamide). Considering factors such as production cost and safety, domestic production enterprises basically use chlorine Sulfoxide, the process has been basically mature and finalized. [0003] The Vilsmeier salt prepared by thionyl chloride releases a large amount of acid gases such as sulfur dioxide and hydrogen chloride during the chlorination heating process. In the early stage of tail gas treatment, alkali absorption method was used. The h...

Claims

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Application Information

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IPC IPC(8): C07H13/06C07H1/00
Inventor 朱国廷陈宜武徐萍王平安倪晓春孙同云沈彬
Owner JK SUCRALOSE
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