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Method for synthesizing 2-methyl-2-propyl-1,3-propanediol dimethyl carbonate compound

A propylene glycol carbonate diester and synthesis method technology, applied in the direction of organic chemistry, can solve the problems of high sealing requirements of reaction equipment, troublesome phosgene environmental protection, and hidden safety hazards, and achieve the elimination of large safety hazards, low cost, and three wastes little effect

Inactive Publication Date: 2009-04-22
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Before the present invention provides, this product is generally synthesized by phosgene method, although phosgene method synthetic carbamate medicine is technically mature, but, in phosgene (COCl 2 ) method of industrial production process, the sealing requirements of the reaction equipment are very high, and the investment is also relatively large. The phosgene in the tail gas will cause great trouble from the perspective of environmental protection.
In production, there must be an additional set of equipment for producing and storing phosgene, and there are still great safety hazards in the process

Method used

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  • Method for synthesizing 2-methyl-2-propyl-1,3-propanediol dimethyl carbonate compound
  • Method for synthesizing 2-methyl-2-propyl-1,3-propanediol dimethyl carbonate compound
  • Method for synthesizing 2-methyl-2-propyl-1,3-propanediol dimethyl carbonate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] According to 2-methyl-2-propyl-1,3-propanediol: trichloromethyl chloroformate: the molar ratio of organic amine catalyst substance is 1:0.5:0.2 feeding intake, 2-methyl-2-propyl-1 , 3-propanediol 30g; Trichloromethyl chloroformate 22.46g; Organic solvent chlorobenzene 120g; Organic amine catalyst is N, N-dimethylaniline, feeding quality 5.49g;

[0021] Dissolve 2-methyl-2-propyl-1,3-propanediol and organic amine catalyst in some organic solvents, cool down to -5~15°C, slowly add trichloromethyl chloroformate dissolved in a small amount of organic solvents dropwise Solution, react at 50 ℃ after completion of dropwise addition, track and monitor the reaction end point with gas chromatography, until the completion of the reaction, the chlorobenzene used to dissolve 2-methyl-2-propyl-1,3-propanediol and the organic amine catalyst and The total amount of organic solvent chlorobenzene for dissolving trichloromethyl chloroformate is 120g.

[0022] After the reaction is comple...

Embodiment 2

[0024] According to 2-methyl-2-propyl-1,3-propanediol: trichloromethyl chloroformate: the molar ratio of organic amine catalyst substance is 1:0.5:0.5 feeding intake, 2-methyl-2-propyl-1 , 3-propanediol 30g; Trichloromethyl chloroformate 22.46g; Organic solvent chlorobenzene 120g; Organic amine catalyst is N, N-dimethylaniline, feeding quality 13.73g;

[0025] The reaction was carried out at a temperature of 30° C., and other operations were the same as in Example 1 to obtain 25.20 g of 2-methyl-2-propyl-1,3-propanediol carbonate, with a yield of 70.2% and a purity of 98.1%.

Embodiment 3

[0027] According to 2-methyl-2-propyl-1,3-propanediol: trichloromethyl chloroformate: the molar ratio of organic amine catalyst substance is 1:0.7:0.5 feeding intake, 2-methyl-2-propyl-1 , 3-propanediol 30g; Trichloromethyl chloroformate 31.45g; Organic solvent cyclohexanone 180g; Organic amine catalyst is N, N-dimethylaniline, feeding quality 13.73g;

[0028] The reaction was carried out at -5°C, and other operations were the same as in Example 1 to obtain 28.07 g of 2-methyl-2-propyl-1,3-propanediol carbonate, with a yield of 82.1% and a purity of 98.1%.

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Abstract

The invention relates to a method for synthesizing a 2-methyl-2-propyl-1, 3-propanediol diester carbonate compound by using trichloromethyl chloroformate, which comprises the following steps: using 2-methyl-2-propyl 1, 3-propanediol and the trichloromethyl chloroformate as raw materials to completely react with each other under the action of an organic amine catalyst in an organic solvent at a temperature of between 5 DEG C below zero and 50 DEG C, and separating and purifying reaction solution to obtain the 2-methyl-2-propyl-1, 3-propanediol diester carbonate, wherein the molar ratio of the 2-methyl-2-propyl 1, 3-propanediol to the trichloromethyl chloroformate to the organic amine catalyst is 1 to 0.5-2.5 to 0.2-2.5. The method adopts the trichloromethyl chloroformate to prepare the key intermediate 2-methyl-2-propyl-1, 3-propanediol diester carbonate of carisoprodol, has high yield, safety, no pollution, and simple operation and is a synthetic route with broad industrialization prospect.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing 2-methyl-2-propyl-1,3-propanediol carbonate diester. (2) Background technology [0002] 2-Methyl-2-propyl-1,3-propanediol carbonate is the key intermediate of Calipodol, also known as Calipodol, which is the center of development in the United States in the 1960s Sexual skeletal muscle relaxants, recorded in the United States Pharmacopoeia (27th edition), the main production areas are Switzerland, Italy, and India. Ranked 26th, 28th, and 24th in the list of best-selling generic drugs, with corresponding sales of 182, 231, and 280 million U.S. dollars. Experts predict that by 2010, the global sales of this market are expected to exceed 40 billion US dollars. [0003] Before the present invention provides, this product is generally synthesized by phosgene method, although phosgene method synthetic carbamate medicine is technically mature, but, in phosgene (COCl 2 ) method of industrial production ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06
Inventor 李坚军苏为科蒲通金林勇
Owner ZHEJIANG UNIV OF TECH
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