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Method for preparing penicillin-G-1-(S)-oxide

A technology of penicillin sulfoxide and penicillin, which is applied in the field of preparation of penicillin sulfoxide, can solve the problems of reduced production efficiency and output, long production cycle, and poor product quality, and achieve the effects of reduced labor intensity, reduced production cycle, and simple operation

Inactive Publication Date: 2011-02-16
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantages of this method are: the three processes are independent of each other and carried out separately, the process is more complicated, the production cycle is long, and the product quality is poor
Moreover, in the crystallization process of dilute acid to adjust the pH value, a large amount of water resources are consumed and a large amount of waste acid solution is produced, which not only reduces production efficiency and output, but also causes a large amount of waste and pollution

Method used

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  • Method for preparing penicillin-G-1-(S)-oxide
  • Method for preparing penicillin-G-1-(S)-oxide
  • Method for preparing penicillin-G-1-(S)-oxide

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Get 500mL penicillin fermented liquid, the penicillin concentration 6g / L in the fermented liquid. Weigh 0.5g of activated carbon into the penicillin fermentation broth, stir for 10 minutes to decolorize, after the decolorization is completed, measure 500mL of butyl acetate and add to the fermentation broth and stir, adjust the pH value of the penicillin fermentation broth to 1.5 with 2mol / L dilute sulfuric acid aqueous solution for extraction. After continuing to stir for 30 minutes, the solution was transferred to a separatory funnel, and the butyl acetate phase was separated from the fermentation broth to obtain a 6 g / L penicillin butyl acetate solution. It was added to the crystallizer and stirred at a constant temperature of -5°C. Measure 7.5mL of peracetic acid solution with a concentration of 8% and cool it down to -5°C, then add it into the crystallizer at a rate of 0.12mL / min to carry out oxidation reaction crystallization. After the dropwise addition of the ox...

Embodiment 2

[0028] Take by weighing 35g penicillin salt, be dissolved in 500mL water, obtain the aqueous solution that penicillin salt concentration is 70g / L. Weigh 1.5 g of activated carbon and add penicillin saline solution, stir and decolorize for 20 minutes. After decolorization is completed, measure 500 mL of ethyl acetate and add penicillin saline solution to stir, and use 1 mol / L dilute sulfuric acid aqueous solution to adjust the pH value of penicillin saline solution to 2.0 for extraction. After continuing to stir for 30 minutes, the solution was transferred to a separatory funnel, and the ethyl acetate phase was separated from the aqueous solution to obtain a 70 g / L penicillin ethyl acetate solution. It was added to the crystallizer and stirred at a constant temperature of 0°C. Measure 46.7mL of peracetic acid solution with a concentration of 30% and cool it down to 0°C, then add it into the crystallizer at a speed of 2.33mL / min to carry out oxidation reaction crystallization. ...

Embodiment 3

[0030] Get 500mL penicillin fermented liquid, the penicillin concentration 30g / L in the fermented liquid. Weigh 2 g of activated carbon and add it to the penicillin fermentation broth, stir and decolorize for 30 minutes. After the decolorization is completed, measure 500 mL of methyl acetate and add it to the fermentation broth and stir. Use 2 mol / L dilute sulfuric acid aqueous solution to adjust the pH of the penicillin fermentation broth to 2.5 for extraction. After continuing to stir for 30 minutes, the solution was transferred to a separatory funnel, and the methyl acetate phase was separated from the fermentation broth to obtain a 30 g / L penicillin methyl acetate solution. It was added to the crystallizer and stirred at a constant temperature of 5°C. Measure 12.5 mL of hydrogen peroxide solution with a concentration of 30% and cool it down to 5°C, then slowly add it into the crystallizer at a rate of 1.25 mL / min to carry out oxidation reaction crystallization. After the ...

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Abstract

The invention relates to a method for preparing penicillin-G-1-(S)-oxide. In the method, penicillin G is used as a raw material, and the oxidization of the penicillin G and the crystallization of penicillin-G-1-(S)-oxide which is the oxidization product of the penicillin G are performed at the same time. A penicillin-G-1-(S)-oxide crystal product is obtained by directly adding an oxidant into penicillin G organic phase solution, reacting and crystallizing, the oxidization reaction and the crystallization are performed at the same time, and the crystal product directly precipitates in organic solution. Compared with the conventional direct oxidization process, the method has the advantages that: the operation flow is simplified considerably; the operation is simple and convenient; the labor intensity is lowered; and the production period is shortened obviously. The process of extracting the penicillin G from the organic phase back to a water phase and the process of regulating pH value with diluted acid and crystallizing are saved, so the consumption of waster resources is reduced greatly, the discharge of waste acid liquor is reduced, and the problem of environmental pollution is alleviated obviously. The high-performance liquid chromatography (HPLC) content of the product reaches over 99.0 percent, and the weight yield of products with a main particle size over 30 mu m is over 90 percent.

Description

technical field [0001] The invention belongs to the technical field of chemical engineering crystallization, and in particular relates to a method for preparing penicillin sulfoxide by oxidation reaction crystallization using penicillin as a raw material. Background technique [0002] The chemical name of Penicillin Sulfoxide is 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-( 2S, 5R, 6R)-, 4-oxide, the molecular formula is C 16 h 18 o 5 N 2 S, molecular weight is 350.2, its chemical structure formula is as follows. [0003] [0004] Penicillin sulfoxide is an important intermediate for the preparation of 7-amino-desacetoxycephalosporanic acid (7-ADCA), and 7-ADCA is one of the two major nuclei of cephalosporin antibiotics. It is an important precursor for the production of cephalosporins such as cephalexin, cefadroxil, and cephradine. Therefore, the production quality and yield of penicillin sulfoxide directly affect...

Claims

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Application Information

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IPC IPC(8): C07D499/46C07D499/04
Inventor 王静康井丁丁王永莉张美景侯宝红尹秋响鲍颖龚俊波
Owner TIANJIN UNIV
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