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Application of supported catalyst in continuous preparation of penicillin sulfoxide ester

A supported catalyst, penicillin technology, applied in molecular sieve catalysts, physical/chemical process catalysts, organic chemistry, etc., can solve the problems of difficult removal of catalyst metabolites, inability to recycle, increase production costs, etc., to reduce synthesis and purification. Difficulty, fast reaction rate, and the effect of improving product quality

Active Publication Date: 2022-05-06
SHENYANG RES INST OF CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, there are mainly two methods for synthesizing penicillin sulfoxide ester with penicillin G potassium as a raw material. The first method uses about 15% peracetic acid as an oxidizing agent to oxidize. In the post-treatment process of this method, a large amount of alkali needs to be used to neutralize a large amount of Acetic acid, a large amount of sodium bisulfite quenches excess peracetic acid, so a large amount of industrial wastewater and waste salt are produced, which is not conducive to environmental protection and increases production costs
The second method uses vanadium pentoxide or sodium tungstate catalyst and hydrogen peroxide as the oxidant to oxidize. The catalyst metabolites are not easy to remove, which affects product quality. At the same time, these metal catalysts cannot be recycled, resulting in waste of resources.

Method used

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  • Application of supported catalyst in continuous preparation of penicillin sulfoxide ester
  • Application of supported catalyst in continuous preparation of penicillin sulfoxide ester
  • Application of supported catalyst in continuous preparation of penicillin sulfoxide ester

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Embodiment 1-13

[0039] 1. Penicillin G potassium ester synthesis:

[0040]4L of dichloromethane, 2Kg of penicillin G potassium, 1.165Kg of p-nitrobenzyl bromide and 100g of triethylbenzyl ammonium chloride were successively added into a 10-liter glass reactor. Stir and heat up, reflux for 6-7 hours, HPLC tracking, after the reaction is completed, cool down to room temperature, add 2L of water, stir evenly, let stand for 30 minutes, and release the organic phase. The aqueous phase was extracted twice with 0.5 L of dichloromethane, the organic phases were combined, and the organic phase was rinsed twice with 0.5 L of water, and the rinsed organic phase was set aside. The concentration of penicillin G potassium ester was 27.66%.

[0041] 2. Preparation of catalyst:

[0042] The supported catalyst is prepared by the impregnation method. Under the protection of nitrogen, the transition metal salt and the coordination metal are added and dissolved in the solvent (the amount of solvent should be d...

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Abstract

The invention belongs to the technical field of chemistry and chemical engineering. The invention specifically relates to an application of a supported catalyst in continuous preparation of penicillin sulfoxide ester. A carrier of the supported catalyst is an ordered mesoporous material SBA-15, an active component of the supported catalyst is a metal salt, and the mass of the active component metal salt is 1-10% of the mass of the ordered mesoporous material SBA-15. Under the action of a supported catalyst, hydrogen peroxide and penicillin G potassium ester are subjected to a continuous flow oxidation reaction, an oxidation reaction solution is subjected to a continuous flow quenching reaction with a sodium hydrogen sulfite aqueous solution, and a quenching reaction solution is subjected to post-treatment to obtain the penicillin sulfoxide ester. The catalyst provided by the invention has the advantages of simple preparation, high catalytic efficiency, high selectivity and the like, and can be recycled after simple activation. By adopting the supported catalyst disclosed by the invention, the reaction conversion rate of penicillin sulfoxide ester preparation can reach 99.5%, the selectivity can reach 100%, the separation yield can reach 95.9%, and the content can reach 99.3%.

Description

technical field [0001] The invention belongs to the technical field of chemistry and chemical engineering. Specifically, it is the application of a supported catalyst in the continuous preparation of penicillin sulfoxide ester. Background technique [0002] Cephalosporin antibiotics have the advantages of strong selectivity to bacteria, low toxicity to human body, broad-spectrum antibacterial, strong antibacterial effect, and less allergic reactions than penicillins, and are widely used. As an important intermediate in the synthesis of cephalosporin antibiotics, penicillin sulfoxide (GESO) has a wide range of applications and broad market prospects. There are currently four methods for the synthesis of penicillin sulfoxide (GESO) reported in the literature: m-chloroperoxybenzoic acid oxidation, peracetic acid oxidation, oxygen catalytic oxidation, and hydrogen peroxide oxidation. In 1963, Eli Lilly and Company of the United States converted penicillin skeleton to cephalosp...

Claims

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Application Information

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IPC IPC(8): C07D499/04C07D499/46B01J29/03
CPCB01J29/0341C07D499/46C07D499/04B01J2229/18Y02P20/584
Inventor 柴宝山周龙王云华邢久歌王志强焦佳媛韩涛王旭东朱君王珂鄢冬茂
Owner SHENYANG RES INST OF CHEM IND
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