Preparation method of L-hydroxyproline monocrystal

A technology of hydroxyproline and single crystal, which is applied in the field of preparation of L-hydroxyproline single crystal, which can solve the problems of low quality of ordinary crystal products, randomness and difficulty in large-scale industrial production, and achieve low solvent pollution and low pollution , easy to transport and store, no discoloration effect

Active Publication Date: 2017-10-13
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention aims at the problems of low quality common crystal products existing in the preparation process of L-hydroxyproline in the prior art, large randomness in production and difficulty in large-scale industrial production, etc., and provides a single crystal of L-hydroxyproline preparation method

Method used

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  • Preparation method of L-hydroxyproline monocrystal
  • Preparation method of L-hydroxyproline monocrystal
  • Preparation method of L-hydroxyproline monocrystal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Weigh respectively 13.11 g of ordinary L-hydroxyproline powder and 15.20 g of ethylene glycol monomethyl ether in a substance ratio of 1:2; mix and stir at 75° C. for 55 min to make L-hydroxyproline Dissolve completely in alcohol monomethyl ether; Add simultaneously the L-hydroxyproline of 6wt% tetrabutylammonium bromide / ethylene glycol deep eutectic solvent 0.79g and 1.5wt% based on the L-hydroxyproline powder mass Amino acid single crystal seed crystal 0.20g; stop the reaction after mixing and stirring for 6 minutes while maintaining a constant temperature; use program cooling to cool the solution at 0.3°C / min in the range of 75-65°C, and at 0.5°C in the range of 65-40°C Cool down at 1.5°C / min in the range of 40-20°C, and then keep aging at 20°C for a period of time until no single crystal of L-hydroxyproline is precipitated. Filter, wash, and vacuum-dry to obtain a white needle-like L-hydroxyproline single crystal. The whole crystallization process takes about 3 hou...

Embodiment 2

[0036] Weigh 13.11g of ordinary L-hydroxyproline powder and 22.80g of ethylene glycol monomethyl ether, mix and stir at 65°C for 60min until completely dissolved; while maintaining constant temperature, add tetraethylammonium chloride / glycerine Alcohol deep eutectic solvent 0.79g and L-hydroxyproline single crystal seed 0.20g; stop the reaction after mixing and stirring for 6 minutes; cool down at 0.4°C / min in the range of 65-55°C, and at 0.8°C in the range of 55-40°C ℃ / min cooling, in the range of 40-20 ℃ according to 2 ℃ / min cooling, and then keep 20 ℃ aging for a period of time until there is no longer L-hydroxyproline single crystal precipitation. Filter, wash, and vacuum-dry to obtain a white needle-like L-hydroxyproline single crystal. The whole crystallization process takes about 3 hours, and the filtered mother liquor is reused. After the obtained L-hydroxyproline single crystal was placed in the air for 24 hours, no agglomeration occurred, and the moisture absorption...

Embodiment 3

[0038]Weigh 26.22g of ordinary L-hydroxyproline powder and 45.60g of ethylene glycol monomethyl ether, mix and stir at 50°C for 80min until completely dissolved; add tetramethylammonium bromide / glycerol low 1.75g ​​of eutectic solvent and 0.40g of L-hydroxyproline single crystal seed; stop the reaction after mixing and stirring for 8 minutes; cool down at 0.5°C / min in the range of 50-45°C, and at 0.6°C / min in the range of 45-40°C Cool down for 1.5°C / min in the range of 40-20°C, and then keep aging at 20°C for a period of time until no single crystal of L-hydroxyproline is precipitated. Filter, wash, and vacuum-dry to obtain a white needle-like L-hydroxyproline single crystal. The whole crystallization process takes about 3 hours, and the filtered mother liquor is reused. After the obtained L-hydroxyproline single crystal was placed in the air for 24 hours, no agglomeration occurred, and the moisture absorption was determined to be 1.79wt%, which was far lower than the common ...

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Abstract

The invention belongs to the field of chemistry, and particularly relates to a preparation method of an L-hydroxyproline monocrystal. The preparation method comprises the following steps: (1) weighing L-hydroxyproline powder and ethylene glycol monomethyl ether according to proportions; (2) mixing and stirring for 15 to 120 minutes under 30 to 85 DEG C, and enabling L-hydroxyproline to be completely dissolved in the ethylene glycol monomethyl ether; (3) simultaneously adding a quaternary ammonium salt eutectic solvent and an L-hydroxyproline monocrystal seed; (4) stopping reacting after mixing and stirring for 5 to 10 minutes under the condition of keeping a constant temperature; (5) gradually cooling to 20 to 30 DEG C by adopting programmed cooling, and then aging for a certain time until no L-hydroxyproline monocrystal is separated out; (6) filtering, washing, and vacuum drying, thus obtaining a white needle-like L-hydroxyproline monocrystal. By adopting the technical scheme of the invention, an obtained L-hydroxyproline monocrystal product is high in quality, is not easy to absorb moisture and deliquesce, has no color change and is good in thermal stability; the technical operating conditions are mild, volume production efficiency is high, the period is short, a solvent is difficult to volatize, the pollution is small, cyclic utilization can be realized, and three wastes are not generated.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a preparation method of L-hydroxyproline single crystal. Background technique [0002] L-Hydroxyproline (C 5 h 9 NO 2 , the structural formula is as figure 1 shown), an important imino neutral amino acid, is an important component of collagen and has the largest content. [0003] L-Hydroxyproline was obtained from gelatin by Fischer in 1902, but it was ignored for a long time. In recent years, people have gradually discovered that L-hydroxyproline is an important component of mammalian collagen, and has many important physiological functional properties and unique biological activities. The research and development of L-hydroxyproline has attracted the attention of industries such as biology, pharmacy, food and cosmetics. The content of L-hydroxyproline is an important indicator for detecting physiological behaviors such as collagen metabolism, bone resorption, and canc...

Claims

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Application Information

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IPC IPC(8): C07D207/16
CPCC07B2200/13C07D207/16
Inventor任红威俞磊连少翰段二红李雪牛建瑞
OwnerHEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY