CN102392060A - Recovering method of effective components in amoxicillin enzymatic synthesis mother liquor by utilizing nanofiltration - Google Patents
Recovering method of effective components in amoxicillin enzymatic synthesis mother liquor by utilizing nanofiltration Download PDFInfo
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- CN102392060A CN102392060A CN2011102909617A CN201110290961A CN102392060A CN 102392060 A CN102392060 A CN 102392060A CN 2011102909617 A CN2011102909617 A CN 2011102909617A CN 201110290961 A CN201110290961 A CN 201110290961A CN 102392060 A CN102392060 A CN 102392060A
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Abstract
The invention discloses a recovering method of effective components in amoxicillin enzymatic synthesis mother liquor by utilizing nanofiltration. The method comprises the following steps: (1) regulating pH of the mother liquor; (2) hydrolyzing amoxicillin in the mother liquor by utilizing penicillin acylase, thus only D-hydroxyphenylglycine and 6-amino-penicillanic acid (6-amino-penicillanic acid) exist in the other liquor; (3) preparing concentrated mother liquor by nanofiltration; and (4) separating and recovering the D-hydroxyphenylglycine and the 6-amino-penicillanic acid (6-amino-penicillanic acid) by isoelectric point crystallization. The method has the advantages that: the recycling rate of an inactive lateral chain can be improved regarding certain amoxicillin synthetase with high hydrolysis activity, so that the enzymatic synthesis of amoxicillin is more economical.
Description
Technical field
The present invention relates to the recovery method of effective ingredient in the mother liquor of the synthetic amoxycilline Trihydrate bp of a kind of enzyme process; Particularly relate to and a kind ofly concentrating, to the recovery method of nonactive side chain D-UK 25842 and parent nucleus 6-amino-penicillanic acid in the mother liquor of the synthetic amoxycilline Trihydrate bp of enzyme process through nanofiltration.
Background technology
There are two kinds of methods usually synthetic amoxycilline Trihydrate bp promptly: chemical synthesis and enzymic synthesis method.The synthetic amoxycilline Trihydrate bp of chemical method relates to more chemical reaction step and harsh reaction conditions; Low temperature environment like-50 degree; In reaction process, need with an organic solvent and chemical reagent; Like methylene dichloride, DMAC N,N, pyridine, triethylamine, acetone, pivaloyl chloride etc., unfriendly to environment.
The synthetic amoxycilline Trihydrate bp of enzyme process is parent nucleus and active side chain under the neutral environment of penicillin acylated enzyme catalysis, room temperature condition; Stir in the aqueous phase solution and can accomplish; Reduced production link widely, avoided the use of organic solvent and reagent, whole process is than environmental protection.Simultaneously, on quality product, enzyme process synthetic amoxycilline Trihydrate bp purity is higher than chemical method synthetic product, and drug safety and stability of drug are higher, and therefore, enzyme process synthetic amoxycilline Trihydrate bp quite receives clinician and patient's favor.
Just because of this, the Technology of enzyme process amoxycilline Trihydrate bp more and more receives pharmacy corporation and investigator's concern in recent years.Disclose the method for the synthetic beta-lactam antibiotics of a kind of enzymatic in the U.S. Pat 6048708, this method is used the antibiotic parent nucleus of higher concentration and the transformation efficiency that the side chain donor improves parent nucleus.
In general, enzyme process synthesizes the amoxycilline Trihydrate bp, in order to make the transformation efficiency height of parent nucleus; The supply of active side chain all is excessive, like this, receives the influence of amoxycilline Trihydrate bp synthetic enzyme hydrolytic activity; The hydrolysis meeting of side chain produces a part of nonactive side chain-D-UK 25842; Therefore contain corresponding nonactive side chain, parent nucleus and a small amount of amoxicillin products in the mother liquor, the hydrolytic activity of enzyme is high more, and residual volume is just big more; The economy of the synthetic amoxycilline Trihydrate bp of enzyme process is had a greatly reduced quality, become the bottleneck of amoxycilline Trihydrate bp enzyme method technique Industry Promotion.Therefore, the recycling to these materials is very important.
Patent CN96199571 has introduced the recovery method of microbiotic mother liquor, and its method is decomposed into its initial compounds for through behind the microbiotic in the enzymic hydrolysis mother liquor, separates parent nucleus and acylating agent hydrolysate through reducing pH then.Yet in our experiment; Simulate its method and handle the amoxycilline Trihydrate bp mother liquor, can not obtain the effect of its description, its reason is: in our enzyme process amoxycilline Trihydrate bp mother liquor; The concentration of 6-amino-penicillanic acid parent nucleus and D-UK 25842 is lower, can not realize crystallization without concentrating.Therefore the present invention concentrates through nanofiltration, and the concentration of 6-amino-penicillanic acid parent nucleus and D-UK 25842 is significantly improved, thereby realizes the Crystallization Separation of 6-amino-penicillanic acid parent nucleus and D-UK 25842.
The present invention relates to the recovery method of the nonactive side chain of effective ingredient and parent nucleus in the mother liquor of a kind of enzyme process amoxycilline Trihydrate bp, wherein nonactive side chain refers to the hydrolysate D-UK 25842 of amoxycilline Trihydrate bp side chain, and parent nucleus is a 6-amino-penicillanic acid.Through reclaiming side chain and parent nucleus, can promote enzyme process synthetic transformation efficiency indirectly, reduce raw-material consumption, thereby reduce production costs.
Reclaim D-UK 25842,6-amino-penicillanic acid in the mother liquor of amoxycilline Trihydrate bp; Must realize the separation of amoxycilline Trihydrate bp in the mother liquor, D-UK 25842,6-amino-penicillanic acid; Yet these three kinds of materials all contain amino and carboxyl on chemical structure; Belong to amphoteric substance, the iso-electric point of three kinds of materials is comparatively approaching, and therefore simple dependence isoelectric point crystallization does not reach isolating purpose.
The present invention relates to a kind of elder generation the synthetic amoxycilline Trihydrate bp of enzyme process mother liquor is handled, make the amoxycilline Trihydrate bp be hydrolyzed to 6-amino-penicillanic acid and D-UK 25842, through nanofiltration the effective ingredient in the mother liquor is concentrated again.And then utilize the concentration difference of 6-amino-penicillanic acid and D-UK 25842, through isoelectric point crystallization a large amount of D-UK 25842 Crystallization Separation are come out.
Mother liquor staple behind the separation D-UK 25842 is a 6-amino-penicillanic acid, can return the source of the synthetic amoxycilline Trihydrate bp of enzyme process directly as the lysate of 6-amino-penicillanic acid, directly recycling; The D-UK 25842 forms active side chain, as amoxycilline Trihydrate bp synthetic starting raw material through esterification.
Summary of the invention
The object of the present invention is to provide a kind of recovery method that utilizes nanofiltration to effective ingredient in the mother liquor of the synthetic amoxycilline Trihydrate bp of enzyme process, comprised the steps:
A kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp, it comprises the steps:
(1) regulate mother liquor pH: utilize alkali with mother liquor pH regulator to 9.0～9.5, alkali is any of ammoniacal liquor or sodium hydroxide, and the crystalline particle of the trace in the mother liquor is all dissolved, and each effective ingredient is dissolved in the mother liquor with the form of salt;
(2) utilize Semacylase to handle above-mentioned mother liquor, make amoxycilline Trihydrate bp and D-UK 25842 methyl esters in the mother liquor be hydrolyzed to D-UK 25842 and 6-amino-penicillanic acid.
(3) nanofiltration concentrates the above-mentioned mother liquor that utilizes Semacylase to handle, and along with the nanofiltration round-robin carries out, water and small amounts of inorganic salt will be removed by dialysis, and effective ingredient D-UK 25842 and 6-amino-penicillanic acid will be concentrated in the mother liquor, and concentration improves;
(4) isoelectric point crystallization Separation and Recovery 6-amino-penicillanic acid and D-UK 25842: concentration difference and the iso-electric point difference of utilizing D-UK 25842 and 6-amino-penicillanic acid; Through above-mentioned mother liquor is dripped acid; Acid is hydrochloric acid; Regulate pH to 3.5-5.0, most D-UK 25842s are separated from mother liquor with the crystalline form, thereby realize separating of D-UK 25842 and 6-amino-penicillanic acid.
A kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp; Use in the mother liquor after Semacylase is handled and no longer contain the amoxycilline Trihydrate bp; Residual amoxycilline Trihydrate bp is decomposed into parent nucleus 6-amino-penicillanic acid and nonactive side chain D-D-pHPG in the mother liquor, so that the Separation and Recovery of effective ingredient.
A kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp, said step (3) uses the method for nanofiltration that mother liquor is concentrated, and concentrates the film that uses nanofiltration to use and is the daltonian nf membrane of 100-150 as molecular weight cut-off.Concentrate through nanofiltration, make that the concentration of effective ingredient significantly improves in the mother liquor, to improve the recovery of D-UK 25842 in the crystalline deposit process that helps postorder.
A kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp, the mother liquor after the process nanofiltration concentrates, D-UK 25842 concentration is 50～60g/l.And the concentration of 6-amino-penicillanic acid is different because of the hydrolytic activity of amoxycilline Trihydrate bp synthetic enzyme, differs greatly, and is generally 4～10g/l.
A kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp, the D-UK 25842 after the separation can be passed through preparation D-UK 25842 methyl ester hydrochloride, are used further to the synthetic amoxycilline Trihydrate bp of enzyme process raw material; Isolating mother liquor can be used for the synthetic amoxycilline Trihydrate bp of enzyme process directly as raw material.
The invention has the advantages that: the present invention adopts nanofiltration to concentrate means, can make the enrichment method of effective constituent in coldcondition, no phase transformation, has protected effective constituent to exempt from the destruction that severe condition (such as evaporation concentration) are brought.Utilize ammoniacal liquor or sodium hydroxide,, control under these pH conditions, improve enzymic hydrolysis efficient on the one hand, avoid the racemization under the condition of crossing alkali of left-handed D-pHPG simultaneously mother liquor pH regulator to 9.0～9.5.The D-pHPG of racemization can't directly supply next step use.The 6-APA solution that reclaims enrichment need not crystallization, can continue to replenish 6-APA directly as the 6-APA lysate, has improved the utilization ratio of 6-APA, thereby has improved the amoxycilline Trihydrate bp yield, and the amoxycilline Trihydrate bp yield preferably reaches 95%, more preferably reaches more than 97%.D-pHPG obtains reclaiming efficiently, and the recovery preferably reaches 85%, more preferably reaches more than 90%, and the COD discharging significantly reduces.Nanofiltration gained dialyzate can be used as enzyme process amoxycilline Trihydrate bp raw material methyl esters dissolving water, and 6-APA dissolving water etc. reduce the use of water from the source, realize cleaner production, and are energy-saving and cost-reducing, contamination-reducing synergistic.
Description of drawings
Fig. 1 is a process flow sheet of the present invention.
Embodiment
Embodiment 1: a kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp, it comprises the steps:
(1) regulate mother liquor pH: get amoxycilline Trihydrate bp mother liquor 2000ml, performance liquid chromatography detects the content of each composition in the mother liquor, and detected result is seen table 1.Utilize ammoniacal liquor or sodium hydroxide,, the crystalline particle of the trace in the mother liquor is all dissolved, each effective ingredient is dissolved in the mother liquor with the form of salt mother liquor pH regulator to 9.0～9.5;
(2) utilize Semacylase to handle above-mentioned mother liquor; Make amoxycilline Trihydrate bp and D-UK 25842 methyl esters in the mother liquor be hydrolyzed to D-UK 25842 and 6-amino-penicillanic acid: to add Semacylase 90～150g; Controlled temperature was handled above-mentioned mother liquor 3～10 hours for 15 ℃～25 ℃, made amoxycilline Trihydrate bp and D-UK 25842 methyl esters in the mother liquor be hydrolyzed to D-UK 25842 and 6-amino-penicillanic acid.
(3) nanofiltration concentrates: Semacylase is separated, used molecular weight cut-off to be the daltonian nf membrane of 100-150, nanofiltration concentrates above-mentioned mother liquor; Along with the nanofiltration round-robin carries out; Water and small amounts of inorganic salt will be removed by dialysis, and effective ingredient D-UK 25842 and 6-amino-penicillanic acid will be concentrated in the mother liquor, and concentration improves; Concentrate the long-pending 470ml of being of stepmother's liquid, each material concentration detected result is seen table 1.
(4) isoelectric point crystallization Separation and Recovery 6-amino-penicillanic acid and D-UK 25842: to the mother liquor dripping hydrochloric acid after concentrating; Regulate pH to 5.0; Most D-UK 25842s are separated from mother liquor with the crystalline form; The crystal of separating out detects through performance liquid chromatography, and purity can reach more than 95%, and each material concentration detected result is seen table 1 in the mother liquor after the crystallization.Obtain 23.86g dry powder after the D-D-pHPG crystal drying, the recovery is 94.23%.
(5) mother liquor that detects after separating the D-UK 25842 through performance liquid chromatography contains 6-amino-penicillanic acid; Can be directly as the lysate of 6-amino-penicillanic acid; Be used for the synthetic amoxycilline Trihydrate bp of enzyme process, apply mechanically enzyme process amoxycilline Trihydrate bp, back yield and reach 95.7% (6-APA with new input calculates).
Each composition Liquid Detection result in table 1 mother liquor
Claims (8)
1. a method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp is characterized in that it comprises the steps:
(1) regulates mother liquor pH: utilize alkali with mother liquor pH regulator to 9.0～9.5, the crystalline particle of the trace in the mother liquor is all dissolved, each effective ingredient is dissolved in the mother liquor with the form of salt;
(2) utilize Semacylase to handle above-mentioned mother liquor, make amoxycilline Trihydrate bp and D-p-hydroxyphenylglycine methyl ester in the mother liquor be hydrolyzed to D-UK 25842 and 6-amino-penicillanic acid general.
(3) nanofiltration concentrates the above-mentioned mother liquor that utilizes Semacylase to handle, and along with the nanofiltration round-robin carries out, water and small amounts of inorganic salt will be removed by dialysis, and effective ingredient D-UK 25842 and 6-amino-penicillanic acid will be concentrated in the mother liquor, and concentration improves;
(4) isoelectric point crystallization Separation and Recovery 6-amino-penicillanic acid and D-UK 25842: through above-mentioned mother liquor is dripped acid; Regulate pH to 3.5-5.0; Most D-UK 25842s are separated from mother liquor with the crystalline form, thereby realized separating of D-UK 25842 and 6-amino-penicillanic acid.
2. a kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp according to claim 1 is characterized in that the alkali that said step (1) is mentioned is any of ammoniacal liquor or sodium hydroxide.
3. a kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp according to claim 1; It is characterized in that; Residual amoxycilline Trihydrate bp is decomposed into parent nucleus 6-amino-penicillanic acid and nonactive side chain D-UK 25842 in the mother liquor after the use Semacylase is handled, so that the Separation and Recovery of effective ingredient.
4. a kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp according to claim 1; It is characterized in that; Said step (3) uses the method for nanofiltration that mother liquor is concentrated, and concentrates the film that uses nanofiltration to use and is the daltonian nf membrane of 100-150 as molecular weight cut-off.
5. a kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp according to claim 1 is characterized in that, the mother liquor after concentrating through nanofiltration, and D-UK 25842 concentration is 50～60g/l.
6. a kind of method of utilizing nanofiltration to reclaim effective ingredient in the mother liquor of enzyme process amoxycilline Trihydrate bp according to claim 1 is characterized in that the acid of said step (4) is hydrochloric acid.
7. one kind is utilized nanofiltration to reclaim the purposes that D-UK 25842 in the mother liquor of enzyme process amoxycilline Trihydrate bp can prepare D-UK 25842 methyl ester hydrochloride, also is used further to the raw material of the synthetic amoxycilline Trihydrate bp of enzyme process.
8. one kind is utilized the isolating mother liquor in nanofiltration recovery enzyme process amoxycilline Trihydrate bp to be used for the synthetic amoxycilline Trihydrate bp of enzyme process directly as raw material.
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| CN102816803A (en) * | 2012-09-10 | 2012-12-12 | 华北制药集团先泰药业有限公司 | Method for recycling active ingredients in amoxicillin mother liquor synthesized by enzymatic method |
| CN103045474A (en) * | 2013-01-07 | 2013-04-17 | 厦门市天泉鑫膜科技股份有限公司 | Recovery equipment and technology for hydroxy phenylglycine in amoxicillin synthetic mother solution |
| CN103553952A (en) * | 2013-10-11 | 2014-02-05 | 孟兰尊 | Method for recovering alpha-amino-p-hydroxyphenylacetic acid in solution |
| CN104357528A (en) * | 2014-10-29 | 2015-02-18 | 国药集团威奇达药业有限公司 | Method for comprehensively recovering effective ingredients in amoxicillin mother liquid prepared by enzyme process |
| CN104628587A (en) * | 2015-02-12 | 2015-05-20 | 山东鲁抗立科药业有限公司 | Method for recovering D-p-hydroxyphenylglycine in amoxicillin production waste liquid |
| CN105254520A (en) * | 2015-10-12 | 2016-01-20 | 国药集团威奇达药业有限公司 | Recovery method for D-hydroxyphenylglycine in amoxicillin crystallization mother liquor of enzymatic synthesis |
| CN105349608A (en) * | 2015-12-16 | 2016-02-24 | 厦门市天泉鑫膜科技股份有限公司 | Method for recycling phenylglycine in cefalexin crystallization mother liquid |
| 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 |
| CN105838771A (en) * | 2015-01-16 | 2016-08-10 | 上海凯鑫分离技术股份有限公司 | Recovery process of amoxicillin crystal mother solution |
| CN114105797A (en) * | 2021-09-10 | 2022-03-01 | 上海城建职业学院 | Method for recovering D-p-hydroxyphenylglycine from crystallization mother liquor |
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| CN102816803A (en) * | 2012-09-10 | 2012-12-12 | 华北制药集团先泰药业有限公司 | Method for recycling active ingredients in amoxicillin mother liquor synthesized by enzymatic method |
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| CN105838771B (en) * | 2015-01-16 | 2019-09-27 | 上海凯鑫分离技术股份有限公司 | Amoxicillin crystalline mother solution recovery process |
| CN104628587B (en) * | 2015-02-12 | 2016-06-22 | 艾美科健（中国）生物医药有限公司 | A kind of amoxicillin of reclaiming produces the method for D-pHPG in waste liquid |
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| CN105254520B (en) * | 2015-10-12 | 2017-07-07 | 国药集团威奇达药业有限公司 | The recovery method of D D-pHPGs in the crystalline mother solution of enzymatic clarification Amoxicillin |
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| CN114105797A (en) * | 2021-09-10 | 2022-03-01 | 上海城建职业学院 | Method for recovering D-p-hydroxyphenylglycine from crystallization mother liquor |
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