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Modified sucrose-6-ester chloridization process

A sucrose, process technology, applied in the field of improved sucrose-6-ester chlorination process, can solve problems such as improper temperature

Inactive Publication Date: 2008-03-12
MAITE SHANGHAI BIOLOGICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Similarly, Chortyk found that a certain molar amount of chlorinating reagent was critical for the sufficient chlorination of sucrose esters, but excessive chlorinating reagents or improper addition of concentration or temperature would lead to the decomposition of sucrose esters (Chortyk, O.T., "Chemically Synthesized Sugar Esters for the Control of Soft-Bodied Arthropods", US Patent 6,608,039, August 19, 2003.)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of Sucrose-6-Ester

[0027] Inject 34.2 kg of sucrose and 140 liters of DMF into a four-port reaction kettle equipped with a stirring device, and heat the solution to 90°C. Stir for 30 minutes. The resulting clear solution was cooled to 40°C, 14 kg of N,N-dimethylacetamide dimethyl acetal was added dropwise, and stirred at 40°C to 50°C for another 2.5 hours. After part of the solution was removed under vacuum, the mixture was cooled to below 20°C and 14 liters of water were added. Acetic acid was added and stirred for 30 minutes to adjust the pH of the mixture to 6.5. HPLC analysis showed that the sucrose-6-ester content was 29.2% (yield 85%).

Embodiment 2

[0029] Mix 1.5 kg sucrose with 3000 ml DMF, stir, and add 863 ml trimethyl orthoacetate and 3 ml concentrated sulfuric acid at 60 °C. After heating for 2 hours, it was cooled to 25°C. Add 0.3ml of concentrated sulfuric acid and 470ml of water. At this point the temperature rose to about 40°C. Cool to 25°C. After 30 minutes, add 6g of calcium chloride, and react for one hour so that the 4-ethyl ester group is moved to the 6-position. The reaction was quenched with 21 ml of a 1:10 concentrated sulfuric acid:water mixture. Insoluble material (calcium sulfate) was removed by filtration. After the filtrate was concentrated under reduced pressure at 80-85°C to form a slurry, it was dissolved with 3000ml of hot methanol. Crystallization was seeded with 7.5 g of sucrose-6-ethyl ester for 4 hours. The product was collected, washed with methanol (250ml x 6 times), and dried under vacuum at 45°C. Yield 990 g, 48% yield, containing 80% sucrose-6-ethyl ester.

Embodiment 3

[0031] Synthesis of Sucralose-6-ester

[0032] 35 g of the sucrose-6-ester of Example 1 was vacuum condensed to a paste and diluted with 150 ml of DMF. Cool to below 0°C. Slowly add 50 g of thionyl chloride dropwise into a four-necked bottle filled with 150 ml of DMF, and control the temperature not higher than 25°C. After the thionyl chloride was added dropwise, dilute sucrose-6-ester was added, and the reaction was continued for 30 minutes. Warm slowly to 110-115°C and allow to react for 3.5 hours. Cool to below 20°C. The solution was neutralized to neutral with NaOH. DMF was removed under reduced pressure. 200 ml of water were added and extracted with ethyl acetate. The organic phases are mixed, condensed, crystallized and recrystallized. 25.3 g of high-purity sucralose-6-acetate was obtained.

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PUM

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Abstract

The present invention describes an improved sucrose-6-ester selective chlorination method, which comprises (1) the three hydroxides in a mol of sucrose -6 - hydroxy ester are processed with moderate amount of 1.75-4.5 mol of chloride reagent; and (2) adopts five-stage method to control the reaction temperature, the reaction time, the feeding speed and the feeding method. The process can enhance the purity of the sucralose-6-ester, and simplify the final recrystallization step of the sucralose. Through the control over the reaction temperature, the reaction time, the feeding speed and the feeding method in the stage 5, the synthesis rate of the sucralose-6-ester is maximized. The mol of chloride reagent used in the reaction is controlled within 1.75 to 4.5. In this say, unnecessary by products are not generated, and higher product and purity are achieved. The present invention provides simpler recrystallization approach and much lower manufacturing cost.

Description

field of invention [0001] The present invention relates to an improved chlorination process of sucrose-6-ester. Background technique [0002] The chlorination of carbohydrates has been studied for many years using a variety of chlorination reagents. Its general significance is to develop a better method for bleaching pulp in the papermaking process. For example, Barham disclosed the use of liquid chlorine to chlorinate carbohydrate esters in cellulose (Barham, H.N., "Chlorination of Carbohydrate Esters", US Patent 2,562,883, August 7, 1951.). Among them, 6 times the molar equivalent of chlorine is needed to achieve the desired chlorination effect. Boehm discusses the chlorination of cellulose using a solution of thionyl chloride in pyridine, arguing that a significant molar excess of chlorine must be present (Boehm, R.L., "Chlorination of Cellulose with Thionyl Chloride in a Pyridine Medium", J. Org. Chem, 23 (1716-1720), 1958.). Recently, McDonough and Reeve studies hav...

Claims

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Application Information

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IPC IPC(8): C07H13/06C07H5/02
Inventor 罗毅潘欣刘齐斌王小曾
Owner MAITE SHANGHAI BIOLOGICAL TECH
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