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A kind of preparation method of l-prolinol

A technology of prolinol and pyroglutamic acid, which is applied in the field of L-prolinol preparation, can solve the problems of high price of raw material L-proline and high production cost, etc., and is suitable for large-scale industrial production, The effect of short process route and high yield

Active Publication Date: 2019-06-18
BEIJING GREENCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method utilizes catalytic hydrogenation to basically achieve green synthesis, and has the advantages of short process route, high yield, and simple post-treatment. However, the raw material L-proline used in this method is expensive, so the preparation cost remains high.

Method used

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  • A kind of preparation method of l-prolinol
  • A kind of preparation method of l-prolinol
  • A kind of preparation method of l-prolinol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] (1) Preparation of molybdenum atom modified ruthenium carbon catalyst

[0056] Weigh 47.26g of activated carbon powder and disperse it in 200mL of deionized water; weigh 6.723g of ruthenium chloride trihydrate and dissolve it in 100mL of deionized water; under stirring conditions, mix the two and absorb for 1 hour; weigh 1.911g of molybdic acid Ammonium solid ((NH 4 ) 6 Mo 7 o 24 4H 2 (0), be dissolved in 50mL deionized water, gradually add in the above-mentioned gac solution under stirring condition; After stirring and absorbing for 1 hour, add sodium borohydride aqueous solution (1.2g sodium borohydride is dissolved in 100mL deionized water) gradually, react 1 at room temperature Hours later, filter with suction, wash 5 times with deionized water to near neutrality, and dry in an oven at 80° C. for 12 hours to obtain a molybdenum atom-modified ruthenium carbon catalyst, wherein the mass percentage of ruthenium is 5 wt%, and the mass percentage of molybdenum The c...

Embodiment 2

[0063] Preparation of L-prolinol

[0064] In a 2L autoclave, add 400g of L-pyroglutamic acid, 380ml of acetic acid, and 1000ml of water, and add the molybdenum atom-modified ruthenium carbon catalyst prepared in Example 1 (1) (ruthenium content: 5wt%, molybdenum content: 2wt%) 60 g, reacted for 18 hours under the condition that the hydrogen pressure was 7.5 MPa and the temperature was 105°C. Cool down to room temperature, release the pressure, and filter. The filter cake ruthenium carbon sleeve was used for the next reaction, and the filtrate was concentrated under reduced pressure to obtain about 450 g of L-prolinol crude product. The crude product was rectified to obtain 292 g of L-prolinol with a purity of 99.4% (GC), and a yield of 91%. The obtained product is consistent with the reference substance (GC analysis).

Embodiment 3

[0066] Preparation of L-prolinol

[0067] In a 20L there-necked flask, add 4kg of L-pyroglutamic acid, 4L of acetic acid, and 10L of water, stir and dissolve, add the molybdenum atom-modified ruthenium carbon catalyst prepared in Example 1 (1) (ruthenium content: 5wt%, molybdenum content: 2wt%) 600g. Under stirring, vacuum suction into the 20L autoclave. Under the conditions of hydrogen pressure of 8 MPa and temperature of 110° C., the reaction was carried out for 20 hours. Cool down to room temperature, release the pressure, and filter. The filter cake ruthenium carbon sleeve was used for the next reaction, and the filtrate was concentrated under reduced pressure to obtain about 4.2 kg of L-prolinol crude product. The crude product was rectified to obtain 2.9kg of L-prolinol with a purity of 99.3% (GC), and a yield of 90%. The obtained product is consistent with the reference substance (GC analysis).

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Abstract

The invention relates to a preparation method of L-prolinol, which is prepared from cheap L-pyroglutamic acid as a raw material by high-pressure hydrogenation reduction with a transition metal atom-modified ruthenium-carbon catalyst. The catalytic activity of the modified ruthenium-carbon catalyst is significantly higher than that of the existing commercial ruthenium-carbon catalyst, so that the lactam hydrogenation reaction of L-pyroglutamic acid, which is difficult to implement, can be smoothly carried out. The preparation method of L-prolinol provided by the invention has the following benefits: the process route is short, the yield is high (up to about 90%), the post-treatment is simple, the catalyst can be reused for more than 20 times, acid water can be recycled after distillation, green synthesis is basically realized, no waste water and waste residues are generated, a large amount of solid waste and waste water generated by reduction of hydroborate and lithium aluminum hydride are avoided, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for preparing L-prolinol, in particular to a method for preparing L-prolinol by high-pressure hydrogenation reduction of L-pyroglutamic acid, which belongs to the technical field of organic synthesis. Background technique [0002] L-prolinol is an important chiral chemical reagent. It is not only a raw material for the synthesis of new materials such as excellent optical materials and chiral polymers, but also a synthetic chiral drug such as avanafil, duloxetine, and Important chiral sources or intermediates of poxetine, evanafil, tolvaptan and other drugs. In recent years, with the rapid development of asymmetric catalytic technology, L-prolinol has become an excellent ligand for metal coordination catalysis, and is widely used in asymmetric metal alkylation reactions, Michael addition reactions, phase transfer catalysis, etc. in organic synthesis. [0003] There are two traditional methods for synthesizing L-prolin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/08B01J23/648B01J23/652B01J23/656B01J23/89
CPCY02P20/584
Inventor 宫宁瑞
Owner BEIJING GREENCHEM TECH
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