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Chemical synthesis method of pyroglutamic acid alcohol and intermediates thereof

A pyroglutamic acid alcohol, chemical synthesis technology, applied in organic chemistry and other directions, can solve the problems of harsh equipment requirements, poor operating conditions, large catalyst consumption, etc., and achieves less demanding equipment requirements, easy subsequent purification, and operating conditions good effect

Inactive Publication Date: 2010-12-29
SICHUAN TONGSHENG AMINO ACID CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Before the present invention was made, when synthesizing pyroglutamic acid, the salt or ester of glutamic acid was selected as raw material for dehydration cyclization, as document CN1398853A, DE3735263 records, so not only can introduce corresponding impurity, but pyroglutamic acid is easy It is soluble in water, which brings great inconvenience to the subsequent separation. At the same time, there is no corresponding purification method in the separation and purification, which results in a long production cycle of pyroglutamic acid and low quality.
[0003] When synthesizing pyroglutamic acid ester, in the past, use glutamic acid esterification-extraction, concentration-cyclization-distillation purification to obtain product pyroglutamic acid ethyl ester, as " chemical reagent ", vol.22No4.Dec., 2000( Hubei University Journal) is recorded; its process route is long, catalyst consumption is big, and alkali consumption is many, operating condition is relatively poor, is difficult for subsequent purification, and equipment requirement is harsh, contains acid and other impurity in the product and is difficult for removal, is unfavorable for product The preservation and the synthesis of subsequent product pyroglutamic acid alcohol, the product yield is also very low
[0004] And when synthesizing pyroglutamin alcohol, most select sodium borohydride as the reducing agent, and the yield is high, but the post-treatment adopts chromatographic column separation, complicated operation, long cycle, low yield, and is not easy for industrialized production

Method used

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  • Chemical synthesis method of pyroglutamic acid alcohol and intermediates thereof
  • Chemical synthesis method of pyroglutamic acid alcohol and intermediates thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Add 60kg of glutamic acid to a 200L electric heating stainless steel reaction tank, stir and dehydrate in an oil bath at 220-290°C, keep the reaction at 140°C for 55 minutes, put it into 10L of water, stir and cool, and centrifuge to obtain the crude product. The crude product is saturated with water at 65°C, centrifugally filtered, cooled to 35°C to crystallize, centrifugally washed and dried to obtain the fine product of pyroglutamic acid. The mother liquor was concentrated and refined, and a total of 28kg of refined pyroglutamic acid was collected, with a yield of 54% (based on the theoretical yield of glutamic acid feeding), and a melting point of 159-161°C, [α] 20 =—11.6 (C=2, H 2 O).

Embodiment 2

[0023] Add 80kg of glutamic acid to a 200L electric heating stainless steel reaction tank, stir and dehydrate in an oil bath at 250-270°C, keep the reaction at 160°C for 50 minutes, put it into 10L of water, stir and cool, and centrifuge to obtain the crude product. The crude product is saturated with water at 50°C, centrifugally filtered, cooled to 30°C to crystallize, centrifugally washed and dried to obtain the refined product of pyroglutamic acid. The mother liquor was concentrated and refined, and a total of 37kg of refined pyroglutamic acid was collected, with a yield of 53.8% (based on the theoretical yield of glutamic acid feeding), and a melting point of 158.5-161°C, [α] 20 =—11.5 (C=2, H 2 O).

Embodiment 3

[0025] Add 60kg of glutamic acid to a 200L electric heating stainless steel reaction tank, stir and dehydrate in an oil bath at 220-250°C, keep the reaction at 140°C for 55 minutes, put it into 10L of water, stir and cool, and centrifuge to obtain the crude product. The crude product is saturated with water at 65°C, centrifugally filtered, cooled to 35°C to crystallize, centrifugally washed and dried to obtain the fine product of pyroglutamic acid. The mother liquor was concentrated and refined, and a total of 28kg of refined pyroglutamic acid was collected, with a yield of 54% (based on the theoretical yield of glutamic acid feeding), and a melting point of 159-161°C, [α] 20 ==—11.5(C=2,H 2 O).

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Abstract

The invention provides a chemosynthesis method of pyroglutamic acid alcohol and intermediates thereof, i.e., pyroglutamic acid and pyroglutamic acid ester, wherein, glutamic acid is used as raw material which is dehydrated and cyclized in a heating environment to generate pyroglutamic acid which is then reacted with absolute alcohol under the effect of catalyst to generate pyroglutamic acid ester; finally, pyroglutamic acid ester is dissolved in organic solvent to be reduced by reducing agent to generate pyroglutamic acid alcohol. The chemosynthesizing method has the advantages that the raw material is easy to get, the process route is short, catalyst and acid consumption are little, the operation environment is good, the yield coefficient is high, the cost is low, the purity is high and the method is easy for industrialization.

Description

technical field [0001] The invention relates to a chemical synthesis method of pyroglutamic acid alcohol and its intermediates, especially using glutamic acid as a raw material, dehydration and cyclization in a heating environment to generate pyroglutamic acid, and then pyroglutamic acid is used as a catalyst Then react with anhydrous alcohol to generate pyroglutamic acid ester, and finally dissolve pyroglutamic acid ester in an organic solvent and reduce it with a reducing agent to generate pyroglutamic acid alcohol. As a natural heat preservation agent, pyroglutamic acid is widely used in cosmetics and daily products. Its derivatives used to synthesize pyroglutamic acid are widely used in the chemical industry. The main raw material of methyl / ethyl glutamate; pyroglutamate is not only the main raw material for the synthesis of pyroglutamate alcohol and the intermediate of other drugs, but also the raw material for the synthesis of 2-pyrrolidone-5-carboxylic acid long-chain f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/26
Inventor 伍万兵范兆林蒲国波陈书娟
Owner SICHUAN TONGSHENG AMINO ACID CO LTD
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