A kind of preparation method of L-hydroxyproline single crystal

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 specifically relates to a preparation method of L-hydroxyproline single crystal. Background technique

[0002] L-Hydroxyproline (C 5 H 9 NO 2 , Structural formula such as figure 1 Shown), an important imino-neutral amino acid, is an important component of collagen and has the most content.

[0003] L-Hydroxyproline was obtained from gelatin by Fischer in 1902, but it did not receive attention 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 functions 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, cancer metastasis in the...

Examples

Embodiment 1

[0034] Weigh 13.11g of ordinary L-hydroxyproline powder and 15.20g of ethylene glycol monomethyl ether in a ratio of 1:2; mix and stir at 75°C for 55 minutes to make L-hydroxyproline in ethylene Alcohol monomethyl ether is completely dissolved; at the same time, 6wt% tetrabutylammonium bromide / ethylene glycol eutectic solvent 0.79g and 1.5wt% L-hydroxyproline based on the mass of L-hydroxyproline powder are added Amino acid single crystal seed crystal 0.20g; mixed and stirred for 6 min under the condition of keeping constant temperature, the reaction was stopped; the temperature of the solution was reduced in the range of 75-65℃ according to 0.3℃ / min, and 0.5℃ in the range of 65-40℃ Cool down at a temperature of 1.5°C / min in the range of 40-20°C, and then keep the temperature at 20°C for a period of time until no L-hydroxyproline single crystal precipitates. Filtration, washing, and vacuum drying to obtain white needle-like L-hydroxyproline single crystals. The entire crystall...

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 60 minutes until completely dissolved; while maintaining constant temperature, add tetraethylammonium chloride / glycerol Alcohol eutectic solvent 0.79g and L-hydroxyproline single crystal seed crystal 0.20g; mixed and stirred for 6min, the reaction was stopped; at 65-55℃, the temperature was lowered at 0.4℃ / min, and at 55-40℃, it was at 0.8 Cool down at a temperature of 2°C / min in the range of 40-20°C, and then keep the temperature at 20°C for a period of time until no L-hydroxyproline single crystal is precipitated. Filtration, washing, and vacuum drying to obtain white needle-like L-hydroxyproline single crystals. The entire crystallization process takes about 3h, and the filtered mother liquor is reused. The obtained L-hydroxyproline single crystal was placed in the air for 24 hours without agglomeration. The moisture absorption was determined to b...

Embodiment 3

[0038] Weigh 26.22g of ordinary L-hydroxyproline powder and 45.60g of ethylene glycol monomethyl ether, mix and stir at 50℃ for 80min to completely dissolve; add tetramethylammonium bromide / glycerol low at 50℃ 1.75g ​​of eutectic solvent and 0.40g of L-hydroxyproline single crystal seed crystal; mixed and stirred for 8 minutes and then stopped the reaction; in the range of 50-45℃, the temperature will be reduced according to 0.5℃ / min, and in the range of 45-40℃ according to 0.6℃ / The temperature is lowered in minutes, and the temperature is lowered at 1.5°C / min in the range of 40-20°C, and then kept at 20°C for aging for a period of time until no L-hydroxyproline single crystal is precipitated. Filtration, washing, and vacuum drying to obtain white needle-like L-hydroxyproline single crystals. The entire crystallization process takes about 3h, and the filtered mother liquor is reused. The obtained L-hydroxyproline single crystal was placed in the air for 24 hours without agglo...

Technical field

[0001] The invention belongs to the field of chemistry, and specifically relates to a preparation method of L-hydroxyproline single crystal. Background technique

[0002] L-Hydroxyproline (C 5 H 9 NO 2 , Structural formula such as figure 1 Shown), an important imino-neutral amino acid, is an important component of collagen and has the most content.

[0003] L-Hydroxyproline was obtained from gelatin by Fischer in 1902, but it did not receive attention 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 functions 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, cancer metastasis in the...

Examples

Embodiment 1

[0034] Weigh 13.11g of ordinary L-hydroxyproline powder and 15.20g of ethylene glycol monomethyl ether in a ratio of 1:2; mix and stir at 75°C for 55 minutes to make L-hydroxyproline in ethylene Alcohol monomethyl ether is completely dissolved; at the same time, 6wt% tetrabutylammonium bromide / ethylene glycol eutectic solvent 0.79g and 1.5wt% L-hydroxyproline based on the mass of L-hydroxyproline powder are added Amino acid single crystal seed crystal 0.20g; mixed and stirred for 6 min under the condition of keeping constant temperature, the reaction was stopped; the temperature of the solution was reduced in the range of 75-65℃ according to 0.3℃ / min, and 0.5℃ in the range of 65-40℃ Cool down at a temperature of 1.5°C / min in the range of 40-20°C, and then keep the temperature at 20°C for a period of time until no L-hydroxyproline single crystal precipitates. Filtration, washing, and vacuum drying to obtain white needle-like L-hydroxyproline single crystals. The entire crystall...

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 60 minutes until completely dissolved; while maintaining constant temperature, add tetraethylammonium chloride / glycerol Alcohol eutectic solvent 0.79g and L-hydroxyproline single crystal seed crystal 0.20g; mixed and stirred for 6min, the reaction was stopped; at 65-55℃, the temperature was lowered at 0.4℃ / min, and at 55-40℃, it was at 0.8 Cool down at a temperature of 2°C / min in the range of 40-20°C, and then keep the temperature at 20°C for a period of time until no L-hydroxyproline single crystal is precipitated. Filtration, washing, and vacuum drying to obtain white needle-like L-hydroxyproline single crystals. The entire crystallization process takes about 3h, and the filtered mother liquor is reused. The obtained L-hydroxyproline single crystal was placed in the air for 24 hours without agglomeration. The moisture absorption was determined to b...

Embodiment 3

[0038] Weigh 26.22g of ordinary L-hydroxyproline powder and 45.60g of ethylene glycol monomethyl ether, mix and stir at 50℃ for 80min to completely dissolve; add tetramethylammonium bromide / glycerol low at 50℃ 1.75g ​​of eutectic solvent and 0.40g of L-hydroxyproline single crystal seed crystal; mixed and stirred for 8 minutes and then stopped the reaction; in the range of 50-45℃, the temperature will be reduced according to 0.5℃ / min, and in the range of 45-40℃ according to 0.6℃ / The temperature is lowered in minutes, and the temperature is lowered at 1.5°C / min in the range of 40-20°C, and then kept at 20°C for aging for a period of time until no L-hydroxyproline single crystal is precipitated. Filtration, washing, and vacuum drying to obtain white needle-like L-hydroxyproline single crystals. The entire crystallization process takes about 3h, and the filtered mother liquor is reused. The obtained L-hydroxyproline single crystal was placed in the air for 24 hours without agglo...

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