Process for synthesis of methylation-beta-cyclodextrin with dimethyl carbonate and beta-cyclodextrin

A technology of dimethyl carbonate and cyclodextrin, applied in the field of synthesizing methylated-β-cyclodextrin from dimethyl carbonate and β-cyclodextrin, can solve the problem of increasing risks and restricting methylation-β-cyclodextrin dextrin application and other issues, to achieve the effects of environmental friendliness, high average substitution degree and high conversion rate

Inactive Publication Date: 2009-08-19
PUYANG VOCATIONAL & TECHN COLLEGE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although these methods are all carried out at normal temperature and pressure, and the reaction conditions are mild, toxic substances such as dimethyl sulfate or methyl halide are used, which increases the risk of scientific research and production processes, and also restricts methylation. - Application of β-cyclodextrin as a pharmaceutical excipient

Method used

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  • Process for synthesis of methylation-beta-cyclodextrin with dimethyl carbonate and beta-cyclodextrin
  • Process for synthesis of methylation-beta-cyclodextrin with dimethyl carbonate and beta-cyclodextrin
  • Process for synthesis of methylation-beta-cyclodextrin with dimethyl carbonate and beta-cyclodextrin

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Experimental program
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Embodiment 1

[0018] Embodiment 1: In the three-necked round-bottom flask with reflux condenser and stirring, add 10g β-cyclodextrin (8.8mmol) and stir in 57g dimethylformamide DMF until clarification, then add 8.6g K 2 CO 3 After stirring for 10 minutes, add 3 mL (34 mmol) of dimethyl carbonate, continue to stir, and control the temperature in an ice-water bath to 0° C., and react for 2 hours. The reaction process is monitored by thin-layer chromatography (TLC). After the reaction, the potassium carbonate K was removed by centrifugation. 2 CO 3 and suspended solids, the pressure is 150-260Pa, the liquid phase temperature is 60-85°C, the solvent dimethylformamide DMF and unreacted dimethyl carbonate are distilled off under reduced pressure, the solution is concentrated to syrup, and added to it after cooling 100mL of acetone was stirred, and the acetone was filtered off, and the solid powder obtained was soaked in anhydrous ether for 16 hours, soaked three times to obtain 4.52 grams of th...

Embodiment 2

[0019] Embodiment 2: In the three-necked round-bottomed flask with reflux condenser and stirring, add 5gβ-cyclodextrin (4.4mmol) and 57g dimethylformamide DMF and stir until clarification, then add 4.0g potassium carbonate K 2 CO 3 After stirring for 10 minutes, add 5 mL (56.7 mmol) of dimethyl carbonate, continue to stir, heat in a water bath to control the temperature at 50° C., and react for 12 hours. The reaction process is monitored by TLC. After the reaction, K was removed by centrifugation 2 CO 3 and suspended solids, the pressure is 150-260Pa, the liquid phase temperature is 60-85°C, the solvent DMF and unreacted dimethyl carbonate are distilled off under reduced pressure, the solution is concentrated to syrup, after cooling, add 100mL acetone to it, stir, The acetone was filtered off, and the obtained solid powder was soaked in anhydrous ether for 24 hours, soaked twice to obtain 3.45 g of the product, the yield of β-cyclodextrin was 69%, and the average degree of s...

Embodiment 3

[0020] Embodiment 3: In the three-necked round-bottomed flask with reflux condenser and stirring, add 5g β-cyclodextrin (4.4mmol) and 57g dimethylformamide DMF and stir until clarification, then add potassium carbonate 1.0gK 2 CO 3 After stirring for 10 minutes, add 16.5 mL (185 mmol) of dimethyl carbonate, continue to stir, and react at 95° C. for 24 hours. The reaction process is monitored by TLC. After the reaction, K was removed by centrifugation 2 CO 3 and suspended solids, the pressure is 150-260Pa, the liquid phase temperature is 60-85°C, the solvent dimethylformamide DMF and unreacted dimethyl carbonate are distilled off under reduced pressure, the solution is concentrated to syrup, and added to it after cooling 100mL of acetone was stirred, and the acetone was filtered off, and the obtained powder solid was soaked in anhydrous ether for 24 hours, soaked twice to obtain 3.32 grams of the product, the yield of β-cyclodextrin was 66.4%, and the average degree of substi...

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Abstract

The invention relates to environmentally-friendly methylating reagent methyl carbonate which replaces methylating reagents toxic to human body and endangering environment (such as dimethyl sulfate or halomethane) to synthesize environmentally-friendly methylated beta-cyclodextrin and a process of synthesizing the methylated beta-cyclodextrin with beta-cyclodextrin. The process comprises the following procedures: allowing the beta-cyclodextrin to react with the methyl carbonate in dimethyl formamide organic solvent in the presence of K2CO3, removing the K2CO3 and other insoluble substances by filtration after complete reaction, depressurizing to distill the solvent, condensing the solution; precipitating the product, filtering, soaking the crude product with absolute ethyl ether, and drying to obtain the product. The process is characterized by replacing methylated reagents toxic to human body and endangering environment (such as dimethyl sulfate or halomethane) with the environmentally-friendly methylated reagent namely methyl carbonate to react with the beta-cyclodextrin to synthesize the environmentally-friendly methylated beta-cyclodextrin. The process has the advantages of simple condition, high conversion of the beta-cyclodextrin, and high average degree of substitution of the product, and environmentally friendly characteristic.

Description

technical field [0001] The invention relates to a synthesis process of methylated-β-cyclodextrin, in particular to a method of using green methylating reagent dimethyl carbonate to replace methyl sulfate such as dimethyl sulfate or methyl halide which is toxic to human body and risky to the environment. Synthesis of green methylated-β-cyclodextrin dimethyl carbonate and β-cyclodextrin synthesis of methylated-β-cyclodextrin technology. Background technique [0002] β-cyclodextrin has a cavity molecular structure and the characteristics of inner hydrophilic and outer hydrophobic, and can be widely used in separation, medicine, catalysis, etc.; however, due to the low solubility of the β-cyclodextrin parent and the inclusion properties limitations, so that its application is limited. Methylated-β-cyclodextrin, as a derivative molecule with high solubility and good inclusion performance among β-cyclodextrin derivatives, is often used in drug inclusion to improve drug applicatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16
Inventor 甘永江李清霞张毅民张运申赵瑜藏
Owner PUYANG VOCATIONAL & TECHN COLLEGE
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