Hydrogenation catalyst for doxycycline production and preparation method and application thereof

A hydrogenation catalyst, doxycycline technology, applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, catalytic reaction, etc. and other problems, to achieve the effect of easy recovery, good gas-liquid distribution, and reduction of isomerization reactions

Active Publication Date: 2020-03-27
扬州联博药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the traditional process of using Pd / C as hydrogenation catalyst and nitrogen-containing compounds such as quinoline pyridine polyamines as ligands has poor selectivity, difficult recovery of ligands, and wide pore size distribution of loaded activated carbon, which has a certain impact on the conversion rate of the reaction. Influence, occasionally there will be material blocking phenomenon

Method used

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  • Hydrogenation catalyst for doxycycline production and preparation method and application thereof
  • Hydrogenation catalyst for doxycycline production and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] put R 1 -N 3 (R 1 for polystyrene) with R 2 -CH≡CH(R 2 is the ligand binap) in anhydrous THF (tetrahydrofuran) solvent with cuprous chloride as a catalyst to stir until the reaction is completed, filter dry and wash with alcohol before use.

[0028] Stir 1kg of polystyrene load (n=500, m=1, and the modification group is binap) in 20kg of 42% ethanol, add a hydrochloric acid solution containing 0.02kg of palladium chloride and stir, stir for 1 hour, stir at a temperature of 25°C, and cool After reaching 10°C, add 9kg of 11α-chlorometacycline p-toluenesulfonate, pass hydrogen to react for 7h, filter after completion of the reaction, and separate the palladium-polystyrene supported catalyst and the reaction solution.

[0029] Compared with the results of using Pd / C as catalyst under the same conditions, the relative content of doxycycline was increased by 6.7%, the relative content of 6-epidoxycycline was decreased by 42.7%, and the yield of doxycycline was increased b...

Embodiment 2

[0031] 1kg polystyrene load (n=500, m=3, the modification group is quinoline, the preparation method is the same as that of Example 1, R 2 For ligand quinoline), stir in 20kg 42% ethanol, add hydrochloric acid solution containing 0.02kg palladium chloride and stir, stir for 1 h, stirring temperature is 25 ℃, after cooling to 10 ℃, add 9kg 11α-chlorometacycline The p-toluenesulfonate was passed through hydrogen to react for 8 hours, and after the reaction was completed, the palladium-polystyrene supported catalyst and the reaction solution were separated by filtration.

[0032] Compared with the results of using Pd / C as catalyst under the same conditions, the relative content of doxycycline was increased by 6.1%, the relative content of 6-epidoxycycline was decreased by 35.3%, and the yield of doxycycline was increased by 2.0%.

Embodiment 3

[0034] Put 1kg of the polystyrene load (n=500, m=3, the modification group is quinoline) filter cake obtained in Example 2 into a chromatographic column with an inner diameter of 15cm, rinse with 200mL of ethanol and 200mL of purified water, and then use 1.7 L 0.3mol / L thiourea and 0.2mol / L hydrochloric acid aqueous solution were washed, and the washing solution was collected. The washing solution was adsorbed and recovered by cation exchange resin and then eluted with hydrochloric acid to obtain PdCl 2 The recovery rate of palladium is 99.1%; the recovered thiourea can be recycled and used in the next round of catalyst recovery process. The eluted polystyrene load was soaked in ammonia water, and rinsed with water and ethanol respectively for use after rinsing.

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Abstract

The invention discloses a hydrogenation catalyst for doxycycline production and a preparation method and application thereof, and belongs to the technical field of compound preparation and hydrogenation industrial catalyst use. The catalyst is composed of PdCl2 and a polystyrene load, the polystyrene load uses polystyrene as a carrier for terminal modification, straight-chain alkane triazole is used as a linking group and a nitrogen-containing ligand is used as a modification group A. The preparation method of the catalyst is simple, the yield and the purity of doxycycline are finally optimized in the doxycycline production process, the doxycycline can be recycled and the catalytic effect is stable.

Description

technical field [0001] The invention belongs to the technical field of compound preparation and hydrogenation industrial catalyst use, and in particular relates to a hydrogenation catalyst for doxycycline production and a preparation method and application thereof. Background technique [0002] Doxycycline, also known as doxycycline hydrochloride or deoxyoxytetracycline hydrochloride, is mainly used as an antibiotic drug for the treatment of fast violet staining-positive cocci and negative bacilli infections, and can also be used for typhus, scrub typhus, etc. The infection of Ketids is also effective for amoebic dysentery and atypical pneumonia. At present, the production process of doxycycline is based on oxytetracycline as raw material, which is obtained by chlorination, dehydration, hydrogenation, transformation and purification. In the production process of doxycycline, the hydrogenation reaction process is the most important step in the entire process route, and it is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/06B01J27/13C07C231/12C07C237/26
CPCB01J31/06B01J27/13C07C231/12C07C2603/46B01J2231/645C07C237/26
Inventor 黄忠明王天池陈佳业苏令倪再欣章留留金亮
Owner 扬州联博药业有限公司
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