CN105838771A - Recovery process of amoxicillin crystal mother solution - Google Patents
Recovery process of amoxicillin crystal mother solution Download PDFInfo
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- CN105838771A CN105838771A CN201510023940.7A CN201510023940A CN105838771A CN 105838771 A CN105838771 A CN 105838771A CN 201510023940 A CN201510023940 A CN 201510023940A CN 105838771 A CN105838771 A CN 105838771A
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- amoxicillin
- mother solution
- water
- recovery process
- crystalline mother
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Abstract
The invention relates to a recovery process of an amoxicillin crystal mother solution. The process includes enzymolysis, filtration, electrodialysis, concentration, crystallization and other steps. The process provided by the invention realizes the recovery and utilization of HPG and 6-APA, reduces the cost of enzymatic preparation of amoxicillin, at the same time realizes inorganic salt recovery, and is friendlier to the environment.
Description
Technical field
The present invention relates to three-protection design, particularly relate to a kind of amoxicillin crystalline mother solution recovery process.
Background technology
Amoxicillin, has another name called amoxicillin, and chemical name is (2S, 5R, 6R)-3,3-dimethyl-6-((R)-(-)-2-
Methyl-2-(4-p-hydroxybenzene) acetylamino)-7-oxo-4-thia-1-azabicyclo (3.2.0) heptane-two-formic acid
Trihydrate.For beta-lactam broad ectrum antibiotic, synthesized by suppression bacteria cell wall, to streptococcus pneumoniae,
The gram positive bacterias such as Hemolytic streptococcus, and the gram negative bacteria such as escherichia coli, salmonella has well
Antibacterial activity.The generally synthesis of amoxicillin has two kinds of methods, respectively chemical synthesis and Enzyme optrode.Enzyme
Method synthesis is parent nucleus 6-amino-penicillanic acid (6-APA) with activity side chain p-hydroxybenzene glycine methyl ester at penicillium sp
Complete under element acylated enzyme catalysis effect.Its reaction condition is gentle, technological process is short, it is to avoid organic solvent and chemistry
The use of reagent, whole process environmental protection.Its product quality is better than chemical synthesis simultaneously.
During using enzymatic clarification amoxicillin, for improving the conversion ratio of 6-APA, during feeding intake
Often add the active side chain of excess.And in course of reaction, amount of activated side chain, such as: D-para hydroxybenzene is sweet
Propylhomoserin methyl ester, is hydrolyzed into nonactive side chain D-pHPG under the effect of PA ase
(HPG).Therefore in the crystalline mother solution of enzymatic clarification amoxicillin, containing nonactive side chain HPG, active side
Chain D-para hydroxybenzene glycine methyl ester, amoxicillin and 6-amino-penicillanic acid.The most still contain substantial amounts of
Inorganic salinity.In the enzymatic clarification technique of amoxicillin, the how mentioned component in effective recycling mother solution,
Become the important topic of enzymatic clarification amoxicillin.
CN1207742A discloses the crystalline mother solution of a kind of beta-lactam antibiotic enzymatic clarification and reclaims β-interior acyl
The technique of amine core.It utilizes the hydrolysis enzyme viability that acylase has in different condition, by the activity in crystalline mother solution
Surveyor's chain and beta-lactam antibiotic hydrolysis so that in system, substance classes reduces, the most nonactive side chain and β-
The existence of lactam core, thus reduce crystallization difficulty, it is achieved the recovery of beta-lactam core.
But due to synthesis and the change of purifying process, said method cannot realize directly reclaiming.CN102392060
Disclose and a kind of utilize nanofiltration to reclaim the technique of effective ingredient in enzymatic amoxicillin mother solution.It uses penicillin
Active side chain in acylase hydrolysis crystalline mother solution and amoxicillin so that with HPG and 6-APA in mother solution system
It is main.But due to not up to crystallisation concentration, employing nanofiltration concentration, promote to HPG concentration, by reconciling PH
Obtain solid HPG.After crystallization, mother solution is as dissolving 6-APA solvent, is back to use in technique.
But it is as the improvement of amoxicillin synthesis technique and extraction process, activity side chain and amoxicillin in mother solution
Content reduces further, and inorganic salt therein increases relatively, uses above-mentioned technique, owing to nanofiltration is difficult to be concentrated to
Crystallization desired concn, causes the difficulty of disposing mother liquor.
Summary of the invention
The purpose of the present invention, it is simply that in order to solve the problem that above-mentioned prior art exists, it is provided that a kind of amoxicillin knot
Brilliant mother liquid recovery process.
In order to achieve the above object, present invention employs techniques below scheme: a kind of amoxicillin crystalline mother solution reclaims
Technique, comprises the following steps:
A, enzymolysis
PA ase is added, by the amoxicillin in mother solution and activity side chain water in the crystalline mother solution of amoxicillin
Solve, generate 6-APA and nonactive side chain HPG；
B, filtration
Being filtered through microfilter by mother solution through enzymolysis, and remove particle therein, filtered solution enters
Next step, the enzyme reuse retained；
C, electrodialysis
Step B gained filtered solution importing electrodialysis system is carried out electrodialysis process, obtains fresh water and dense water, HPG,
6-APA and unhydrolysed amoxicillin and activity side chain stay in fresh water, and the ion in liquid enters in dense water,
Realize ion to separate with organic, realize the concentration of ion simultaneously；Fresh water enters next step, and dense water imports and steams
Send out device to be evaporated concentrating, obtain the crystallization of inorganic salt；
D, concentration
Step C gained fresh water importing membrance concentration system being concentrated, obtain filter liquor and concentrated solution, concentrated solution enters
Enter next step；
E, isoelectric point crystallization
By step D gained concentrated solution inorganic acid for adjusting pH to HPG isoelectric point, IP, HPG crystallization, filter,
Obtain HPG crystallization, reclaim HPG, crystalline mother solution reuse.
Before step B gained filtered solution imports electrodialysis system, regulation pH is 5-9.
Before step B gained filtered solution imports electrodialysis system, first pass through film separation system and remove the color in filtered solution
Element and colloid.
Before step C gained fresh water imports membrance concentration system, first pass through film separation system and remove the pigment in filtered solution
And colloid.
The pore size filter of described microfilter filter element is 1 micron-50 microns.
Before step C gained fresh water imports membrance concentration system, regulation pH is 9-10.
The film that described membrance concentration system uses is more than 98% to the rejection of magnesium sulfate, or retains sodium chloride
Rate is more than 90%, and operation temperature controls at 10-40 DEG C, and operation Stress control is at 1-4Mpa.
The molecular weight that dams of the film that described film separation system is used is 800-10000, and operation temperature controls
10-40 DEG C, operation Stress control is at 0.1-2Mpa.
Pole hydromining in described electrodialysis system is with 0.5%～1.0% sodium-chloride water solution or pure through electrodialysis
The dense water changed, initial dense tank uses tap water or softens water or pure water or the filter liquor of above-mentioned steps D.
Described electrodialysis system uses the mode that multi-machine parallel connection or multimachine series connection or multi-machine parallel connection series connection combine,
To improve the mesohalobic concentration of dense water.
Electrodialysis system involved in the present invention includes being become galvanic power supply, delivery pump and electric osmose from alternating current
Parser.The critical piece of electrodialyzer is anion exchange membrane (abbreviation cavity block), cation exchange membrane (abbreviation sun
Film), dividing plate and electrode.The passage that compartment is liquid stream process that dividing plate is constituted.The compartment of material process is desalting chamber,
The compartment of dense water process is enriched chamber.I.e. the salinity of material is removed, at dense hydroecium, salinity is concentrated simultaneously.
Usual cavity block, anode membrane are alternately arranged with dense water and diluted gasket, and plus pair of electrodes just one electrodialyzer of composition.
The thin film that ion is had selective penetrated property that ion exchange membrane is made up of macromolecular material.Main point of sun from
Proton exchange (CM is called for short anode membrane) and two kinds of anion exchange membrane (AM is called for short cavity block).Anode membrane due to
Film body fixed base is with negatively charged ions, optional through cation；Cavity block is owing to film body fixed base is with positive charge
Ion, optional through anion.Anode membrane passes through cation, and cavity block is referred to as the selection of film through the performance of anion
Permeability.
The most basic working cell of electrodialyzer is referred to as film pair.One film is to constituting a diluting compartment and a concentration
Room.Under the effect of DC electric field, utilize the selective penetrated property of ion exchange membrane, cation permeable anode membrane, cloudy from
Son is through cavity block, and the ion of desalting chamber migrates to enriched chamber, and the ion of enriched chamber is nothing due to the selective penetrated property of film
Normal direction desalting chamber migrates.So salt concentration of diluting compartment is gradually lowered, the salt concentration of adjacent enriched chamber accordingly by
Edge up height.
This technique use Millipore filtration techniques mother solution is carried out pretreatment.Through pretreatment, enzyme hydrolysis can be removed
Particle in liquid, including immobilized enzyme particle and other float.
Filtered solution through pretreatment enters electrodialysis system.Filtered solution is divided into two parts: dense water and fresh water.Wherein
Side chain, 6-APA and unhydrolysed antibiotic and activity side chain etc. are stayed in fresh water, the ion in filtered solution, as
Sulfate ion, chloride ion, sodium ion, ammonium ion etc., under electric drive, enter into dense water end (W.E.) through film, real
Existing ion separates with organic, realizes the concentration of ion simultaneously.And the fresh water inorganic salt in fresh water end is removed.
And the dense water of dense water end (W.E.) is removed the overwhelming majority due to Organic substance, and through initial concentration.This dense water enters vaporizer
It is evaporated concentrating, obtains the crystallization of inorganic salt.After electrodialysis process, salt in the water outlet of fresh water end i.e. fresh water
Clearance reach more than 90%.
The fresh water that electrodialysis produces, enters membrance concentration system after adjusting pH9-10.Under the driving of pressure, water passes through,
Form permeate.Organic substance therein includes HPG, 6-APA, a small amount of amoxicillin and non-complete hydrolysis
Activity side chain is dammed, and along with water is through film, in the liquid that dams, concentration increases, and obtains the concentrated solution of film.In concentrated solution
HPG concentration reaches 50mg/ml-65mg/ml.
The technique of the present invention achieves the recycling of HPG, 6-APA, reduces enzyme process and prepares amoxicillin
Production cost；It is simultaneously achieved the recovery of inorganic salt and the recycling of water, to more environment-friendly.
Detailed description of the invention
Embodiment 1
The crystalline mother solution 100L of amoxicillin, containing HPG1-13mg/ml, amoxicillin 1-5mg/ml, D-to hydroxyl
Base Phenylglycine methyl ester 0-5mg/ml, 6 aminopenicillanic acid 0-5mg/ml, electrical conductivity 10-40ms/cm.Add
PA ase, under the conditions of pH8-9, makes amoxicillin and D-para hydroxybenzene glycine methyl ester be hydrolyzed into HPG
And 6-APA.Enzymolysis solution after having hydrolyzed filters through microfilter, and filtrate is stored in tank.This filtrate adjusts pH
To 6-8.5, it is pumped up into electrodialysis system.Through electrodialysis process, obtain fresh water 85-98L, its electrical conductivity≤
2ms/cm.Dense water conductivity reaches 110-180ms/cm.This fresh water enters membrance concentration system.
Above-mentioned through electrodialytic fresh water, it is pumped up, into membrance concentration system, controlling pressure 1.5-40MPa, temperature 1-40
Degree Celsius, water passes through film, HPG and 6-APA etc. is concentrated.Treat that HPG is concentrated into 50mg/ml, collect and concentrate
Liquid enters next step.
Through the concentrated solution of membrance concentration, slow acid adding adjusts pH to about 5, HPG to analyse from mother solution with the form of crystallization
Go out.Separated, obtain HPG crystallization.This crystallization purity reaches 95%..
Embodiment 2
The crystalline mother solution 100L of amoxicillin, containing HPG2.3mg/ml, amoxicillin 2.1mg/ml, D-to hydroxyl
Phenylglycine methyl ester 0.8mg/ml, 6 aminopenicillanic acid 0.6mg/ml, electrical conductivity 40ms/cm.Add penicillin
Acylase, under the conditions of pH8-9, make amoxicillin and D-para hydroxybenzene glycine methyl ester be hydrolyzed into HPG and
6-APA.Enzymolysis solution after having hydrolyzed filters through microfilter, and filtrate is stored in tank.This filtrate adjusts pH extremely
6-8.5, is pumped up into electrodialysis system.Through electrodialysis, obtain fresh water 90L, its electrical conductivity≤2ms/cm.
Dense water conductivity reaches 110ms/cm.Fresh water enters membrance concentration system.
Above-mentioned fresh water, adjusts PH9.1-9.3, is pumped up, into membrance concentration system, controlling pressure 1.5-40MPa, temperature 1-40
Degree Celsius, water passes through film, HPG and 6-APA etc. is concentrated.Treat that HPG is concentrated into 60-65mg/ml, collect
Concentrated solution enters next step.
Through the concentrated solution of membrance concentration, slow acid adding adjusts pH to about 5, HPG to analyse from mother solution with the form of crystallization
Go out.Separated, obtain HPG crystallization.This crystallization purity reaches 95%.Crystallization yield reaches 80-90%.
Embodiment 3:
By the electrodialysis fresh water in embodiment 2, enter film separation system through pump.Employing filtering accuracy is the molecule that dams
The film of amount 800-2500, controls pressure 1-3Mpa, temperature 1-40 degree Celsius, HPG and 6-APA etc. through film,
Pigment colloid etc. is dammed.A small amount of water is added in concentrated solution end, with the HPG by being deposited in concentrated solution end during terminal
And the film of dialysing such as 6-APA, to improve the response rate.Obtain permeate to concentrate and crystallization through membrance concentration system again.
Improved technique, obtains HPG purity and increases, and reaches 96%, and colourity reduces.Crystalline mother solution simultaneously
Colourity reduces, and favourable 6-APA recycles.
Embodiment 4:
By in embodiment 2 through enzymolysis and the filtrate of filtration, be directly entered film separation system through pump.Use and filter essence
Degree is the film of the molecular weight 800-2500 that dams, and controls pressure 1-3Mpa, temperature 1-40 degree Celsius, HPG and 6-APA
Deng through film, pigment colloid etc. is dammed.Add a small amount of water during terminal in concentrated solution end, concentrated solution end will be deposited in
HPG and 6-APA etc. dialysed film, to improve the response rate.Obtain permeate enter electrodialysis system and after
Continuous step.Realize same technological effect.
Embodiment 5:
Embodiment 1 reclaims the crystalline mother solution after HPG, wherein HPG20-30mg/ml, 6-APA 7-10mg/ml,
Electrical conductivity is more than 30ms/cm.After this crystalline mother solution entrance electrodialysis system carries out desalination, repeat embodiment 1 follow-up
Step, reclaims HPG therein further.
Claims (10)
1. an amoxicillin crystalline mother solution recovery process, it is characterised in that comprise the following steps:
A, enzymolysis
PA ase is added, by the amoxicillin in mother solution and activity side chain water in the crystalline mother solution of amoxicillin
Solve, generate 6-APA and nonactive side chain HPG；
B, filtration
Being filtered through microfilter by mother solution through enzymolysis, and remove particle therein, filtered solution enters
Next step, the enzyme reuse retained；
C, electrodialysis
Step B gained filtered solution importing electrodialysis system is carried out electrodialysis process, obtains fresh water and dense water, HPG,
6-APA and unhydrolysed amoxicillin and activity side chain stay in fresh water, and the ion in liquid enters in dense water,
Realize ion to separate with organic, realize the concentration of ion simultaneously；Fresh water enters next step, and dense water imports and steams
Send out device to be evaporated concentrating, obtain the crystallization of inorganic salt；
D, concentration
Step C gained fresh water importing membrance concentration system being concentrated, obtain filter liquor and concentrated solution, concentrated solution enters
Enter next step；
E, isoelectric point crystallization
By step D gained concentrated solution inorganic acid for adjusting pH to HPG isoelectric point, IP, HPG crystallization, filter,
Obtain HPG crystallization, reclaim HPG, crystalline mother solution reuse.
Amoxicillin the most according to claim 1 crystalline mother solution recovery process, it is characterised in that: step B
Before gained filtered solution imports electrodialysis system, regulation pH is 5-9.
Amoxicillin the most according to claim 1 crystalline mother solution recovery process, it is characterised in that: step B
Before gained filtered solution imports electrodialysis system, first pass through film separation system and remove the pigment in filtered solution and colloid.
Amoxicillin the most according to claim 1 crystalline mother solution recovery process, it is characterised in that: step C
Before gained fresh water imports membrance concentration system, first pass through film separation system and remove the pigment in filtered solution and colloid.
Amoxicillin the most according to claim 1 crystalline mother solution recovery process, it is characterised in that: described micro-
The pore size filter of hole filter element is 1 micron-50 microns.
Amoxicillin the most according to claim 1 crystalline mother solution recovery process, it is characterised in that: step C
Before gained fresh water imports membrance concentration system, regulation pH is 9-10.
Amoxicillin the most according to claim 1 crystalline mother solution recovery process, it is characterised in that: described film
The film that concentration systems uses is more than 98% to the rejection of magnesium sulfate, or the rejection of sodium chloride is more than 90%,
Operation temperature controls at 10-40 DEG C, and operation Stress control is at 1-4Mpa.
8. according to the amoxicillin crystalline mother solution recovery process described in claim 3 or 4, it is characterised in that: institute
The molecular weight that dams stating the film that film separation system is used is 800-10000, and operation temperature controls at 10-40 DEG C,
Operation Stress control is at 0.1-2Mpa.
Amoxicillin the most according to claim 1 crystalline mother solution recovery process, it is characterised in that: described electricity
Pole hydromining in electrodialysis system is with 0.5%～1.0% sodium-chloride water solution, or the dense water through electrodialysis purification,
Initial dense tank uses tap water or softens water or pure water or the filter liquor of above-mentioned steps D.
Amoxicillin the most according to claim 1 crystalline mother solution recovery process, it is characterised in that: described electricity
Electrodialysis system uses the mode that multi-machine parallel connection or multimachine series connection or multi-machine parallel connection series connection combine, to improve dense water
Mesohalobic concentration.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108084206A (en) * | 2018-02-09 | 2018-05-29 | 国药集团威奇达药业有限公司 | The method that ampicillin is recycled from the mother liquor of enzymatic clarification ampicillin |
| CN111269076A (en) * | 2020-03-12 | 2020-06-12 | 山东钧睿科技服务有限公司 | Recovery treatment process for β -lactam antibiotic centrifugal mother liquor synthesized by enzyme method |
| CN113214103A (en) * | 2021-04-23 | 2021-08-06 | 内蒙古常盛制药有限公司 | Subsequent treatment method for enzymatic synthesis of D-p-hydroxyphenylglycine |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108084206A (en) * | 2018-02-09 | 2018-05-29 | 国药集团威奇达药业有限公司 | The method that ampicillin is recycled from the mother liquor of enzymatic clarification ampicillin |
| CN111269076A (en) * | 2020-03-12 | 2020-06-12 | 山东钧睿科技服务有限公司 | Recovery treatment process for β -lactam antibiotic centrifugal mother liquor synthesized by enzyme method |
| CN113214103A (en) * | 2021-04-23 | 2021-08-06 | 内蒙古常盛制药有限公司 | Subsequent treatment method for enzymatic synthesis of D-p-hydroxyphenylglycine |
| CN113214103B (en) * | 2021-04-23 | 2023-05-02 | 内蒙古常盛制药有限公司 | Subsequent treatment method for synthesizing D-p-hydroxyphenylglycine by using enzymatic method |
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