CN104762359A - Recycling process of amoxicillin in enzymatically synthesized amoxicillin mother liquor - Google Patents
Recycling process of amoxicillin in enzymatically synthesized amoxicillin mother liquor Download PDFInfo
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- CN104762359A CN104762359A CN201510176060.3A CN201510176060A CN104762359A CN 104762359 A CN104762359 A CN 104762359A CN 201510176060 A CN201510176060 A CN 201510176060A CN 104762359 A CN104762359 A CN 104762359A
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- amoxycilline trihydrate
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Abstract
The invention discloses a recycling process of amoxicillin in enzymatically synthesized amoxicillin mother liquor. The process comprises the following steps: concentrating the amoxicillin mother liquor through the adoption of nanofiltration membrane high-power concentration equipment, feeding the concentrated liquor in a reaction tank, sufficiently reacting the 6-APA in the concentrated liquor with methyl D-(-)-4-hydroxy-phenylglycinate under the effect of penicillin G acylase so as to generate the amoxicillin. The recycling process disclosed by the invention has the advantages that through the nanofiltration concentration, not only the amoxicillin in the mother liquor is recycled, but also the 6-APA contained in the mother liquor participates the enzymatic synthesis reaction to be translated into the amoxicillin, the aim of extremely recycling the amoxicillin in the mother liquor is achieved, and the recycling process has more economy.
Description
Technical field
The present invention relates to a kind of mother liquid recovery process, particularly relate to the recovery process of amoxycilline Trihydrate bp in the mother liquor of a kind of enzymatic clarification amoxycilline Trihydrate bp, belong to pharmaceutical technology sectors, environmental protection treatment technical field.
Background technology
Amoxycilline Trihydrate bp is a kind of the most frequently used β-lactam antibitics, has a broad antifungal spectrum.At present, the synthetic method of amoxycilline Trihydrate bp has chemical method and enzyme process two kinds of techniques.Chemical method synthesis amoxycilline Trihydrate bp relates to a large amount of organic solvent, while being detrimental to health, go back serious environment pollution.Amoxycilline Trihydrate bp transformation efficiency prepared by enzyme method technique is high, and impurity is few, avoids organic solvent and participates in reaction, greatly reduce the pollution of harm to operator and environment.In the technique of enzymatic clarification amoxycilline Trihydrate bp, although add excessive D-HPG methyl esters to improve the transformation efficiency of 6-APA, but after the completion of reaction, often still the compositions such as a large amount of 6-APA, amoxycilline Trihydrate bp and D-HPG methyl esters can be contained in mother liquor, therefore to reclaim this part mother liquor be very necessary, there is very considerable economic worth.A kind of method utilizing nanofiltration to reclaim D-HPG and 6-APA in the mother liquor of enzymatic clarification amoxycilline Trihydrate bp is disclosed in patent CN102392060A.The recoverying and utilizing method of effective constituent in the mother liquor of a kind of enzymatic clarification amoxycilline Trihydrate bp is disclosed in patent CN102816803A, the method, first through resin isolation D-HPG and 6-APA, recycles ultrafiltration removal of impurities, nanofiltration concentration and recovery D-HPG.Recycled mainly for D-HPG in mother liquor and 6-APA in above-mentioned patent.
At present, still not relevant technology while contained amoxycilline Trihydrate bp, makes 6-APA participation enzymic synthesis reaction contained in mother liquor change into amoxycilline Trihydrate bp and is reclaimed, reclaim amoxycilline Trihydrate bp in mother liquor to the full extent to reach in recovery mother liquor.
Summary of the invention
The object of this invention is to provide the recovery process of amoxycilline Trihydrate bp in the mother liquor of a kind of enzymatic clarification amoxycilline Trihydrate bp, reclaim the amoxycilline Trihydrate bp in the complete mother liquor of crystallization to the full extent.
For realizing object of the present invention, inventor provide following technical scheme.
A recovery process for amoxycilline Trihydrate bp in the mother liquor of enzymatic clarification amoxycilline Trihydrate bp, comprises following operation steps:
(1) get enzymatic clarification amoxycilline Trihydrate bp and amoxycilline Trihydrate bp crystallization complete after mother liquor, with ammoniacal liquor regulable control mother liquor pH6.0 ~ 7.0 that concentration is 5 ~ 15%, pour among high power thickening equipment, make it carry out circulation by nanofiltration membrane to concentrate, the molecular weight cut-off of described nanofiltration membrane is 150 ~ 500 dalton; Control temperature 10 ~ 20 DEG C in concentration process, and observation concentrated solution goes out brilliant situation at any time; When concentrated mother liquor starts crystalline substance, stop concentrated;
(2) step (1) concentrated solution 20ml is got as sample, measure D-HPG in this sample, 6-APA, amoxycilline Trihydrate bp and D-HPG methyl esters content and calculate the amount of substance of contained 6-APA and D-HPG methyl esters in concentrated solution with this, to guarantee that the ratio participating in 6-APA and the D-HPG methyl esters amount of substance reacted in concentrated solution is for 1:1.05, amount of substance as D-HPG methyl esters contained in concentrated solution is not enough, then another reinforcing body D-HPG methyl esters is supplied;
(3) step (2) concentrated solution is dropped into enzyme reaction tank, react under the effect of penicillin G acylase, in described penicillin G acylase and concentrated solution, the mass ratio of contained 6-APA is 1:1, effective constituent 6-APA and D-HPG methyl esters in concentrated solution are fully reacted and generates amoxycilline Trihydrate bp, detect 6-APA in reaction process to remain, when 6-APA is residual be less than 2g/L time, reaction terminates;
(4) after reaction terminates, by concentration be 15 ~ 25% hydrochloric acid out-feed liquid pH is transferred to 0.5 ~ 1.5, make it dissolve completely, filter, under ice-water bath cooling, the ammoniacal liquor that concentration is 5 ~ 15% is added in lysate, material liquid pH is made to be 4.0 ~ 6.0, after growing the grain 1.5h, suction filtration, gained sample is cleaned, dries, is weighed, and calculates the rate of recovery at 1.0 ~ 1.9g/L.
Preferably, the recovery process of amoxycilline Trihydrate bp in the mother liquor of above-mentioned enzymatic clarification amoxycilline Trihydrate bp, comprises following operation steps:
(1) get enzymatic clarification amoxycilline Trihydrate bp and amoxycilline Trihydrate bp crystallization complete after mother liquor, with the ammoniacal liquor regulable control mother liquor pH6.5 that concentration is 10%, pour among high power thickening equipment, make it carry out circulation by nanofiltration membrane and concentrate, the molecular weight cut-off of described nanofiltration membrane is 300 dalton; In concentration process, control temperature is at 15 DEG C, and observation concentrated solution goes out brilliant situation at any time; When concentrated mother liquor starts crystalline substance, stop concentrated;
(2) step (1) concentrated solution 20ml is got as sample, measure D-HPG in this sample, 6-APA, amoxycilline Trihydrate bp and D-HPG methyl esters content and calculate the amount of substance of contained 6-APA and D-HPG methyl esters in concentrated solution with this, to guarantee that the ratio participating in 6-APA and the D-HPG methyl esters amount of substance reacted in concentrated solution is for 1:1.05, amount of substance as D-HPG methyl esters contained in concentrated solution is not enough, then another reinforcing body D-HPG methyl esters is supplied;
(3) step (2) concentrated solution is dropped into enzyme reaction tank, react under the effect of penicillin G acylase, in described penicillin G acylase and concentrated solution, the mass ratio of contained 6-APA is 1:1, effective constituent 6-APA and D-HPG methyl esters in concentrated solution are fully reacted and generates amoxycilline Trihydrate bp, detect 6-APA in reaction process to remain, when 6-APA is residual be less than 2g/L time, reaction terminates;
(4) after reaction terminates, by concentration be 20% hydrochloric acid out-feed liquid pH is transferred to 1.0, make it dissolve completely, filter, under ice-water bath cooling, the ammoniacal liquor that concentration is 10% is added in lysate, material liquid pH is made to be 5.0, after growing the grain 1.5h, suction filtration, gained sample is cleaned, dries, is weighed, and calculates the rate of recovery at 1.85g/L.
The recovery process of amoxycilline Trihydrate bp in the mother liquor of enzymatic clarification amoxycilline Trihydrate bp of the present invention, while its advantage is amoxycilline Trihydrate bp contained by recovery mother liquor, also make 6-APA participation enzymic synthesis reaction contained in mother liquor change into amoxycilline Trihydrate bp to be reclaimed, to reach the object reclaiming amoxycilline Trihydrate bp in mother liquor to the full extent.The present invention, by concentrating mother liquor, greatly reduces the pollution of dialyzate to environment, and the aftertreatment of dialyzate is more prone to, reduce in the past to energy loss, the equipment loss of mother liquid disposal, add profit, there is larger economic worth, be worth promoting in production.
Accompanying drawing explanation
The recovery process schema of amoxycilline Trihydrate bp in the mother liquor of Fig. 1 enzymatic clarification amoxycilline Trihydrate bp of the present invention.
Embodiment
Below in conjunction with specific embodiment, content of the present invention is further described in detail.
The recovery process of amoxycilline Trihydrate bp in the mother liquor of embodiment 1 enzymatic clarification amoxycilline Trihydrate bp of the present invention
(1) get enzymatic clarification amoxycilline Trihydrate bp and amoxycilline Trihydrate bp crystallization complete after mother liquor 270L, with the ammoniacal liquor regulable control mother liquor pH6.5 of 10%, pour among high power thickening equipment, make it carry out circulation by nanofiltration membrane to concentrate, the molecular weight cut-off using film during nanofiltration is 300 dalton, control temperature 15 DEG C in concentration process, and observation concentrated solution goes out brilliant situation at any time; When concentrated mother liquor starts crystalline substance, stop concentrated, final concentrated solution volume is 14L;
(2) step (1) concentrated solution 20ml is got as sample, measure D-HPG in this sample, 6-APA, amoxycilline Trihydrate bp and D-HPG methyl esters content and calculate the amount of substance of contained 6-APA and D-HPG methyl esters in concentrated solution with this, in table 1.The quality of 6-APA is about 212.94g, amount of substance be 0.986mol, the quality of D-HPG methyl esters is about 151.48g, amount of substance be 0.837mol, it is 1:1.05 that amount of substance due to D-HPG methyl esters contained in concentrated solution does not meet the ratio participating in 6-APA and the D-HPG methyl esters amount of substance reacted, so another reinforcing body D-HPG methyl esters 35.81g (0.198mol) is supplied;
(3) step (2) concentrated solution is dropped into enzyme reaction tank, add 213g penicillin G acylase, react under the effect of penicillin G acylase, effective constituent 6-APA and D-HPG methyl esters in concentrated solution are fully reacted and generates amoxycilline Trihydrate bp, detect 6-APA in reaction process to remain, when 6-APA is residual be less than 2g/L time, reaction terminates;
(4) after reaction terminates, with 20% hydrochloric acid, out-feed liquid pH is transferred to 1.0, makes it dissolve completely, filter, under ice-water bath cooling, in lysate, add 10% ammoniacal liquor, make material liquid pH be 5.0, after growing the grain 1.5h, suction filtration, gained sample is cleaned, dries, is weighed, and can obtain amoxycilline Trihydrate bp dry powder 500g, and the rate of recovery is 1.85g/L.
In order to investigate the amoxycilline Trihydrate bp quality condition of recovery of the present invention, the product of contriver to embodiment 1 detects, specifically in table 2.
Table 1 amoxycilline Trihydrate bp original nut liquid and each component content of concentrated solution
| Experiment lot number | D-acid/(g/L) | 6-APA/(g/L) | Amoxycilline Trihydrate bp/(g/L) | Methyl esters/(g/L) |
| Before original nut liquid adjusts pH | 1.56 | 1.22 | 2.04 | 0.94 |
| After original nut liquid adjusts pH | 1.55 | 1.32 | 2.02 | 0.94 |
| Final concentrated solution | 15.12 | 15.21 | 16.46 | 10.82 |
Table 2 disposing mother liquor amoxycilline Trihydrate bp dry powder quality situation
From detected result, the present invention reclaims and the amoxycilline Trihydrate bp of resynthesis from mother liquor, and each side index all meets version " Chinese Pharmacopoeia " standard in 2010.
The recovery process of amoxycilline Trihydrate bp in the mother liquor of embodiment 2 enzymatic clarification amoxycilline Trihydrate bp of the present invention
(1) get enzymatic clarification amoxycilline Trihydrate bp and amoxycilline Trihydrate bp crystallization complete after mother liquor 270L, with the ammoniacal liquor regulable control mother liquor pH6.0 of 5%, pour among high power thickening equipment, make it carry out circulation by nanofiltration membrane to concentrate, the molecular weight cut-off using film during nanofiltration is 150 dalton, control temperature 10 DEG C in concentration process, and observation concentrated solution goes out brilliant situation at any time; When concentrated mother liquor starts crystalline substance, stop concentrated, final concentrated solution volume is 20L;
(2) step (1) concentrated solution 20ml is got as sample, measure D-HPG in this sample, 6-APA, amoxycilline Trihydrate bp and D-HPG methyl esters content and calculate the amount of substance of contained 6-APA and D-HPG methyl esters in concentrated solution with this, in table 3.The quality of 6-APA is about 182.80g, amount of substance be 0.845mol, the quality of D-HPG methyl esters is about 128.60g, amount of substance be 0.710mol, it is 1:1.05 that amount of substance due to D-HPG methyl esters contained in concentrated solution does not meet the ratio participating in 6-APA and the D-HPG methyl esters amount of substance reacted, so another reinforcing body D-HPG methyl esters 32.07g (0.177mol) is supplied;
(3) step (2) concentrated solution is dropped into enzyme reaction tank, add 182.80g penicillin G acylase, react under the effect of penicillin G acylase, effective constituent 6-APA and D-HPG methyl esters in concentrated solution are fully reacted and generates amoxycilline Trihydrate bp, detect 6-APA in reaction process to remain, when 6-APA is residual be less than 2g/L time, reaction terminates;
(4) after reaction terminates, with 20% hydrochloric acid, out-feed liquid pH is transferred to 0.5, makes it dissolve completely, filter, under ice-water bath cooling, in lysate, add 5% ammoniacal liquor, make material liquid pH be 4.0, after growing the grain 1.5h, suction filtration, gained sample is cleaned, dries, is weighed, and can obtain amoxycilline Trihydrate bp dry powder 376g, and the rate of recovery is 1.39g/L.
In order to investigate the amoxycilline Trihydrate bp quality condition of recovery of the present invention, the product of contriver to embodiment 2 detects, specifically in table 4.
Table 3 amoxycilline Trihydrate bp original nut liquid and each component content of concentrated solution
| Experiment lot number | D-acid/(g/L) | 6-APA/(g/L) | Amoxycilline Trihydrate bp/(g/L) | Methyl esters/(g/L) |
| Before original nut liquid adjusts pH | 1.49 | 1.37 | 1.54 | 0.51 |
| After original nut liquid adjusts pH | 1.47 | 1.35 | 1.53 | 0.52 |
| Final concentrated solution | 13.82 | 9.14 | 10.32 | 6.43 |
Table 4 disposing mother liquor amoxycilline Trihydrate bp dry powder quality situation
From detected result, the present invention reclaims and the amoxycilline Trihydrate bp of resynthesis from mother liquor, and each side index all meets version " Chinese Pharmacopoeia " standard in 2010.
The recovery process of amoxycilline Trihydrate bp in the mother liquor of embodiment 3 enzymatic clarification amoxycilline Trihydrate bp of the present invention
(1) get enzymatic clarification amoxycilline Trihydrate bp and amoxycilline Trihydrate bp crystallization complete after mother liquor 270L, with the ammoniacal liquor regulable control mother liquor pH7.0 of 15%, pour among high power thickening equipment, make it carry out circulation by nanofiltration membrane to concentrate, the molecular weight cut-off using film during nanofiltration is 500 dalton, control temperature 20 DEG C in concentration process, and observation concentrated solution goes out brilliant situation at any time; When concentrated mother liquor starts crystalline substance, stop concentrated, final concentrated solution volume is 12L;
(2) step (1) concentrated solution 20ml is got as sample, measure D-HPG in this sample, 6-APA, amoxycilline Trihydrate bp and D-HPG methyl esters content and calculate the amount of substance of contained 6-APA and D-HPG methyl esters in concentrated solution with this, in table 5.The quality of 6-APA is about 196.20g, amount of substance be 0.907mol, the quality of D-HPG methyl esters is about 166.32g, amount of substance be 0.918mol, it is 1:1.05 that amount of substance due to D-HPG methyl esters contained in concentrated solution does not meet the ratio participating in 6-APA and the D-HPG methyl esters amount of substance reacted, so another reinforcing body D-HPG methyl esters 6.16g (0.034mol) is supplied;
(3) step (2) concentrated solution is dropped into enzyme reaction tank, add 196.20g penicillin G acylase, react under the effect of penicillin G acylase, effective constituent 6-APA and D-HPG methyl esters in concentrated solution are fully reacted and generates amoxycilline Trihydrate bp, detect 6-APA in reaction process to remain, when 6-APA is residual be less than 2g/L time, reaction terminates;
(4) after reaction terminates, with 20% hydrochloric acid, out-feed liquid pH is transferred to 1.5, makes it dissolve completely, filter, under ice-water bath cooling, in lysate, add 15% ammoniacal liquor, make material liquid pH be 6.0, after growing the grain 1.5h, suction filtration, gained sample is cleaned, dries, is weighed, and can obtain amoxycilline Trihydrate bp dry powder 436g, and the rate of recovery is 1.61g/L.
In order to investigate the amoxycilline Trihydrate bp quality condition of recovery of the present invention, the product of contriver to embodiment 3 detects, specifically in table 6.
Table 5 amoxycilline Trihydrate bp original nut liquid and each component content of concentrated solution
| Experiment lot number | D-acid/(g/L) | 6-APA/(g/L) | Amoxycilline Trihydrate bp/(g/L) | Methyl esters/(g/L) |
| Before original nut liquid adjusts pH | 1.81 | 1.12 | 2.21 | 0.86 |
| After original nut liquid adjusts pH | 1.80 | 1.24 | 2.17 | 0.83 |
| Final concentrated solution | 16.54 | 16.35 | 18.28 | 13.86 |
Table 6 disposing mother liquor amoxycilline Trihydrate bp dry powder quality situation
From detected result, the present invention reclaims and the amoxycilline Trihydrate bp of resynthesis from mother liquor, and each side index all meets version " Chinese Pharmacopoeia " standard in 2010.
Below be only the preferred embodiment of the present invention; not in order to limit the present invention, to those skilled in the art, under the premise without departing from the principles of the invention; the some improvement that can also make, retouching, equivalent replacement, all should be included within protection scope of the present invention.
Claims (2)
1. the recovery process of amoxycilline Trihydrate bp in the mother liquor of enzymatic clarification amoxycilline Trihydrate bp, is characterized in that, comprise following operation steps:
(1) get enzymatic clarification amoxycilline Trihydrate bp and amoxycilline Trihydrate bp crystallization complete after mother liquor, with ammoniacal liquor regulable control mother liquor pH6.0 ~ 7.0 that concentration is 5 ~ 15%, pour among high power thickening equipment, make it carry out circulation by nanofiltration membrane to concentrate, the molecular weight cut-off of described nanofiltration membrane is 150 ~ 500 dalton; Control temperature 10 ~ 20 DEG C in concentration process, and observation concentrated solution goes out brilliant situation at any time; When concentrated mother liquor starts crystalline substance, stop concentrated;
(2) step (1) concentrated solution 20ml is got as sample, measure D-HPG in this sample, 6-APA, amoxycilline Trihydrate bp and D-HPG methyl esters content and calculate the amount of substance of contained 6-APA and D-HPG methyl esters in concentrated solution with this, to guarantee that the ratio participating in 6-APA and the D-HPG methyl esters amount of substance reacted in concentrated solution is for 1:1.05, amount of substance as D-HPG methyl esters contained in concentrated solution is not enough, then another reinforcing body D-HPG methyl esters is supplied;
(3) step (2) concentrated solution is dropped into enzyme reaction tank, react under the effect of penicillin G acylase, in described penicillin G acylase and concentrated solution, the mass ratio of contained 6-APA is 1:1, effective constituent 6-APA and D-HPG methyl esters in concentrated solution are fully reacted and generates amoxycilline Trihydrate bp, detect 6-APA in reaction process to remain, when 6-APA is residual be less than 2g/L time, reaction terminates;
(4) after reaction terminates, by concentration be 15 ~ 25% hydrochloric acid out-feed liquid pH is transferred to 0.5 ~ 1.5, make it dissolve completely, filter, under ice-water bath cooling, the ammoniacal liquor that concentration is 5 ~ 15% is added in lysate, material liquid pH is made to be 4.0 ~ 6.0, after growing the grain 1.5h, suction filtration, gained sample is cleaned, dries, is weighed, and calculates the rate of recovery at 1.0 ~ 1.9g/L.
2. the recovery process of amoxycilline Trihydrate bp in the mother liquor of a kind of enzymatic clarification amoxycilline Trihydrate bp according to claim 1, is characterized in that, comprise following operation steps:
(1) get enzymatic clarification amoxycilline Trihydrate bp and amoxycilline Trihydrate bp crystallization complete after mother liquor, with the ammoniacal liquor regulable control mother liquor pH6.5 that concentration is 10%, pour among high power thickening equipment, make it carry out circulation by nanofiltration membrane and concentrate, the molecular weight cut-off of described nanofiltration membrane is 300 dalton; In concentration process, control temperature is at 15 DEG C, and observation concentrated solution goes out brilliant situation at any time; When concentrated mother liquor starts crystalline substance, stop concentrated;
(2) step (1) concentrated solution 20ml is got as sample, measure D-HPG in this sample, 6-APA, amoxycilline Trihydrate bp and D-HPG methyl esters content and calculate the amount of substance of contained 6-APA and D-HPG methyl esters in concentrated solution with this, to guarantee that the ratio participating in 6-APA and the D-HPG methyl esters amount of substance reacted in concentrated solution is for 1:1.05, amount of substance as D-HPG methyl esters contained in concentrated solution is not enough, then another reinforcing body D-HPG methyl esters is supplied;
(3) step (2) concentrated solution is dropped into enzyme reaction tank, react under the effect of penicillin G acylase, in described penicillin G acylase and concentrated solution, the mass ratio of contained 6-APA is 1:1, effective constituent 6-APA and D-HPG methyl esters in concentrated solution are fully reacted and generates amoxycilline Trihydrate bp, detect 6-APA in reaction process to remain, when 6-APA is residual be less than 2g/L time, reaction terminates;
(4) after reaction terminates, by concentration be 20% hydrochloric acid out-feed liquid pH is transferred to 1.0, make it dissolve completely, filter, under ice-water bath cooling, the ammoniacal liquor that concentration is 10% is added in lysate, material liquid pH is made to be 5.0, after growing the grain 1.5h, suction filtration, gained sample is cleaned, dries, is weighed, and calculates the rate of recovery at 1.85g/L.
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| CN105567777A (en) * | 2016-03-07 | 2016-05-11 | 内蒙古常盛制药有限公司 | Method for recycling amoxicillin mother solution |
| CN108358951A (en) * | 2018-02-09 | 2018-08-03 | 国药集团威奇达药业有限公司 | The method that Amoxicillin is recycled from the mother liquor of enzymatic clarification Amoxicillin |
| CN109371095A (en) * | 2018-12-06 | 2019-02-22 | 广州市力鑫药业有限公司 | A kind of method of enzymatic clarification Amoxicillin |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105567777A (en) * | 2016-03-07 | 2016-05-11 | 内蒙古常盛制药有限公司 | Method for recycling amoxicillin mother solution |
| CN108358951A (en) * | 2018-02-09 | 2018-08-03 | 国药集团威奇达药业有限公司 | The method that Amoxicillin is recycled from the mother liquor of enzymatic clarification Amoxicillin |
| CN108358951B (en) * | 2018-02-09 | 2019-05-24 | 国药集团威奇达药业有限公司 | The method of Amoxicillin is recycled from the mother liquor of enzymatic clarification Amoxicillin |
| CN109371095A (en) * | 2018-12-06 | 2019-02-22 | 广州市力鑫药业有限公司 | A kind of method of enzymatic clarification Amoxicillin |
| CN109371095B (en) * | 2018-12-06 | 2021-08-20 | 广州市力鑫药业有限公司 | Method for synthesizing amoxicillin by enzyme method |
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