CN107987113A - A kind of method that erythromycin oxime is directly prepared using erythromycin fermentation liquid - Google Patents
A kind of method that erythromycin oxime is directly prepared using erythromycin fermentation liquid Download PDFInfo
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- CN107987113A CN107987113A CN201711399756.8A CN201711399756A CN107987113A CN 107987113 A CN107987113 A CN 107987113A CN 201711399756 A CN201711399756 A CN 201711399756A CN 107987113 A CN107987113 A CN 107987113A
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- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
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Abstract
The present invention relates to a kind of method that erythromycin oxime is directly prepared using erythromycin fermentation liquid, this method is first filtered erythromycin fermentation liquid with membrane filter method, organic solvent extracts, the thick alkali of erythromycin is made in dehydration and decolorization, freezing and crystallizing, oximate is made in oximation reaction afterwards, finally by the extraction of oximate organic solvent, dehydration and decolorization, crystallization is freezed, filtration drying obtains erythromycin oxime.The present invention gives full play to the advantage of this enterprise production erythromycin raw material, the technical process that thiocyanic acid is crystallized with erythromycin into salt is got rid of, directly by the use of preparing the thick alkali of intermediate erythromycin of erythromycin thiocyanate as the starting material of synthesis of erythromycin A9 oximes, so as to simplify technique, technological process is shortened, reduces production cost, environmental pollution is small, product yield is high, and quality is good.
Description
Technical field
The present invention relates to technical field of medicine synthesis, directly prepared using erythromycin fermentation liquid more particularly to one kind red mould
The method of plain oxime.
Background technology
Erythromycin oxime（Erythromycin A 9- oximes）It is mould as azithromycin, clarithromycin, roxithromycin, Ketek and Tai La
The key intermediate of second and third generation macrolide antibiotics of the downstreams such as element, its quality and yield directly influence azithromycin,
The quality and cost of the antibiotic such as clarithromycin, roxithromycin, Ketek and Tulathromycin.
In the prior art, the synthesis of erythromycin oxime is using erythromycin thiocyanate or erythromycin as starting material mostly（It is main
It is all Erythromycin A component to want component）, with polar solvent（Methanol, ethanol etc.）Dissolve erythromycin thiocyanate or erythromycin, azanol
Inorganic acid salt and organic base, carry out the oximate of Erythromycin A by certain time at a certain temperature complete, be down to afterwards
Room temperature adds water oximate is fully precipitated and dissolves inorganic salts etc., filters to obtain oximate, adds polar solvent（Methanol, ethanol etc.）,
Adding liquid caustic soda dissolves oximate, and water, which is added dropwise, separates out erythromycin oxime crystallization, dry erythromycin oxime after filtering.Erythromycin A 9- oximes
Synthetic reaction equation it is as follows：
The essence of above-mentioned synthetic method is the oximation reaction carried out to Erythromycin A.But Erythromycin A unstable chemcial property, lead to
The raw material of erythromycin oxime is re-used as after the erythromycin thiocyanate or erythromycin that often are required for being crystallized into Nature comparison stabilization
Use.This mode, crystallize the Erythromycin A of extraction yield directly influence after oximation reaction the product quality of erythromycin oxime and
Yield, while the crystallization extraction process of Erythromycin A is complicated, process is various, and organic solvent addition is more, and environmental pollution is big, and production is useless
Water is more, ultimately causes production cost increasing.
The content of the invention
The purpose of the present invention is that the defects of overcoming the above-mentioned prior art, there is provided a kind of technique is simple, high income, cost
The method that erythromycin oxime is directly prepared using erythromycin fermentation liquid that is low, polluting small, good product quality, be adapted to industrialized production.
The technical solution taken for achieving the above object is：
A kind of method that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that its processing step is：
1）It is then that gained is dense by erythromycin fermentation liquid successively using ultrafiltration membrance filter plus water dialysis and NF membrane concentration
Contracting liquid is extracted into organic solvent in alkaline conditions, and gained organic phase is dehydrated with adsorbent, decolorization, is depressurized afterwards dense
Contracting, freezes crystallization, and filtration drying obtains the thick alkali of erythromycin；
2）With polar solvent by the inorganic acid salt of the thick alkali of above-mentioned erythromycin and azanol, water miscible alkali soluble solution, oximation reaction, mistake
Filter separates to obtain erythromycin oximate；
3）Above-mentioned gained erythromycin oximate is extracted with organic solvent in alkaline conditions, standing separation, gained organic phase is inhaled
Attached dose of dehydration, decolorization, are concentrated under reduced pressure, and freeze crystallization, and filtration drying obtains erythromycin oxime.
Process 1）Described in erythromycin fermentation liquid before ultrafiltration membrance filter is carried out first with lye adjust pH7.5~8.5.
Process 1）Described in ultrafiltration membrane be organic plate membrane or ceramic membrane that aperture is 5~50nm, ultra-filtration process pressure control
System is in 0.1~0.3MPa, pH7.5~8.5.
Process 1）Described in during NF membrane concentration, filtrate pH controls are in 6.5~7.5, pressure control
3.8MPa, gained concentrate 1~3g/100ml of concentration, NF membrane is the film that molecular cut off is more than 700.
Process 1）With process 3）Described in organic solvent for ethyl acetate, butyl acetate, amyl acetate, dichloromethane, three
Chloromethanes or methyl tertiary butyl ether(MTBE), its dosage are 0.05~1.0 times of erythromycin fermentation liquid quality.
Lye solution used when either reconciling pH or to control the lye used in alkaline condition be that mass concentration is 5
~30% sodium hydroxide solution, ammonia spirit or sodium carbonate liquor.
Process 1）With process 3）Described in adsorbent be activated carbon, diatomite or polymeric retention aid filtering agent, its dosage is organic
The 0.5~2.0% of phase quality.
Process 2）Described in polar solvent be methanol or ethanol, its dosage is 1~5 times of the thick alkali weight of erythromycin, preferably
1.0~3.0 times.
Process 2）In, the thick alkali of erythromycin：The inorganic acid salt of azanol：Water miscible alkali molar ratio is=1:0.1-3.0:0.1-
3.0, preferably 1:0.1-1.0:The inorganic acid salt of 0.1-1.0, wherein azanol are hydroxylamine hydrochloride or aqueous hydroxylamine solution, water miscible alkali
For sodium acid carbonate, sodium hydroxide or triethylamine.
The process 2）Middle oximation reaction process is：Insulated and stirred is anti-under 6.6~6.9,30~40 DEG C of temperature conditionss of pH
24~48 hr are answered, reaction gradient heating is then controlled, raises 1~5 DEG C per hour, be raised to 55~65 DEG C always and maintain stirring 8 again
~12 it is small when, it is complete to oximation reaction, be then cooled to less than 10 DEG C, be separated by filtration to obtain erythromycin oxime.
Process 1）With process 3）Described in freezing crystallization refer to 2~4h of insulated and stirred under -5 DEG C~-15 DEG C temperature conditionss.
The present invention gives full play to the advantage of this enterprise production erythromycin raw material, has got rid of thiocyanic acid and has been crystallized with erythromycin into salt
Technical process, directly using preparing of the thick alkali of intermediate erythromycin of erythromycin thiocyanate as synthesis of erythromycin A9- oximes
Beginning raw material, so as to simplify technique, shortens technological process, reduces production cost；Second, the present invention is carried with membrane filtration technique
Erythromycin A is taken, reduces the use of organic solvent, makes technological operation more easy, production link is more environmentally-friendly, Erythromycin A production
Quality and extract yield are further enhanced, so that ensure that the product quality of erythromycin oxime and the raising of yield, the 3rd,
The present invention extracts oximate with organic solvent in alkaline conditions, standing separation, gained organic solvent solution is dehydrated with adsorbent,
Decolorization, is concentrated under reduced pressure, and freezes crystallization, and filtration drying obtains erythromycin oxime, fundamentally effectively prevent erythromycin thiocyanate
Interference of the middle thiocyanate radical to subsequently synthesizing, and the thiocyanate radical of follow-up erythromycin thiocyanate A9- oximes dissociate removal process,
The accessory substance generation that high pH environment during dissociating continues alkaline degradation is effectively prevent, so as to improve product yield, is reduced
Environmental protection treatment pressure.
To sum up, the method that the present invention utilizes erythromycin fermentation liquid directly to prepare erythromycin oxime is very suitable for industrial metaplasia
Production, its technique is simple, and production cost is low, and environmental pollution is small, and product yield is high, and quality is good.
Embodiment
The present invention is explained with example, it should be understood that example is to be used to illustrate rather than to this below
The limitation of invention.The scope of the present invention is determined with core content according to claims.
In following embodiments, erythromycin fermentation liquid is fermentation obtained by 7 days cultivation and fermentations using streptomyces erythreus microorganism
Liquid pH=6.0~7.0, temperature are 32~36 DEG C, and fermentation unit is generally 6000~9000 μ/mL.
In following embodiments,
The ultrafiltration membrane is the organic plate membrane or ceramic membrane that aperture is 5~50nm, albumen that molecular cut off is more than 10,000 and
Impurity, ultra-filtration process pressure are controlled in 0.1~0.3MPa, pH7.5~8.5.
NF membrane is the film that molecular cut off is more than 700, in nanofiltration concentration process filtrate pH controls 6.5~7.5,
Pressure control is 3.8MPa, 1~3g/100ml of gained concentrate concentration.
Embodiment 1
50L erythromycin fermentation liquids are taken, under conditions of pH8.0, pressure 0.2MPa, using the organic board-like of 5~50nm of aperture
Film is filtered, during peristaltic pump stream add pure water to dialyse；Gained filtrate 110L carries out rolling NF membrane concentration, molecular cut off
For more than 700 film, concentration process filtrate pH controls are 6.5~7.5, and pressure control is 4.0MPa, gained concentrate concentration
For 2.23g/100ml；Concentrate adds 50L butyl acetates, stream plus 10% sodium hydroxide solution, is extracted, extraction process pH
Control stands split-phase, isolated upper strata butyl acetate solution, adds the filtering of 1% activated carbon, vacuum distillation 10.0~10.5
Butyl acetate solution is concentrated, is cooled to less than -5 DEG C crystallizations, insulated and stirred 2hr, is centrifugally separating to obtain the thick alkali of erythromycin.After drying
The thick alkali of gained erythromycin, Erythromycin A content are 90.8%, and water content is below 0.5%, the yield of crystallization process Erythromycin A
95.2%。
The thick alkali of 1Kg erythromycin will be obtained, adds to the glass reaction kettle of 5L, sequentially adds 2.5L absolute ethyl alcohols, hydrochloric acid
Azanol 400g and sodium acid carbonate 360g, stirring and dissolving react 24 hr in 40 DEG C of insulated and stirreds, then control reaction gradient heating,
Per hour raise 1 DEG C, be raised to always 65 DEG C maintain again stirring 8 it is small when, it is complete to oximation reaction, be then cooled to less than 10 DEG C,
It is separated by filtration, obtained erythromycin oximate.
25L butyl acetates, stream plus 20% sodium hydroxide solution are added in erythromycin oximate, is extracted, extraction process pH
Control stands split-phase, isolated upper strata butyl acetate solution, adds the filtering of 1% activated carbon, vacuum distillation 10.0~10.5
Butyl acetate solution is concentrated, is cooled to less than -5 DEG C crystallizations, insulated and stirred 4hr, is centrifugally separating to obtain erythromycin oxime.Institute after drying
Erythromycin oxime is obtained, Erythromycin E oxime content is 91.2%, and erythromycin Z oxime contents are 3.6%, Erythromycin A 9- oximes yield 91.2%.
Embodiment 2
50L erythromycin fermentation liquids are taken, under conditions of pH8.2, pressure 0.22MPa, using the organic plates of 5~50nm of aperture
Formula film is filtered, during peristaltic pump stream add pure water to dialyse, gained filtrate 110L carries out nanofiltration concentration, and molecular cut off is
More than 700 film, concentration process filtrate pH controls are 6.5~7.5, and pressure control is 3.9MPa, gained concentrate concentration
2.12g/100ml ；Concentrate adds 10L dichloromethane, stream plus stream plus 10% ammonium hydroxide, is extracted, extraction process pH controls
9.0~9.5, split-phase is stood, isolated lower floor's dichloromethane solution, adds the filtering of 1.5% diatomite, vacuum distillation concentration
Dichloromethane solution, is cooled to less than -15 DEG C crystallizations, insulated and stirred 3hr, is centrifugally separating to obtain the thick alkali of erythromycin.Institute after drying
The thick alkali of erythromycin is obtained, Erythromycin A content is 92.8%, and water content is below 0.5%, the yield 96.6% of crystallization process Erythromycin A.
The thick alkali of 1Kg erythromycin will be obtained, adds to the glass reaction kettle of 5L, sequentially adds 1.5L absolute methanols, hydrochloric acid
Azanol 450g and sodium acid carbonate 400g, stirring and dissolving, reacts 36 hr in 35 DEG C of insulated and stirreds, then controls reaction gradient liter
Temperature, per hour raise 2.5 DEG C, be raised to always 55 DEG C maintain again stirring 12 it is small when, it is complete to oximation reaction, be then cooled to 10
Below DEG C, it is separated by filtration, obtained erythromycin oximate.
Erythromycin oximate adds 5L dichloromethane, stream plus 10% ammonia spirit, is extracted, and extraction process pH controls exist
9.0~9.5, split-phase is stood, isolated lower floor's dichloromethane solution, adds the filtering of 1.5% diatomite, vacuum distillation concentration two
Chloromethanes solution, is cooled to less than -15 DEG C crystallizations, insulated and stirred 2hr, is centrifugally separating to obtain erythromycin oxime.Gained is red after drying
Mycin oxime, Erythromycin E oxime content are 92.7%, and erythromycin Z oxime contents are 1.8%, Erythromycin A 9- oximes yield 92.8%.
Embodiment 3
50L erythromycin fermentation liquids are taken, under conditions of pH7.8, pressure 0.16MPa, using the organic plates of 5~50nm of aperture
Formula film is filtered, during peristaltic pump stream add pure water to dialyse, gained filtrate 160L carry out nanofiltration concentration, NF membrane for retention
Molecular weight is more than 700 film, and 6.5~7.5, pressure control be 3.8MPa for concentration process filtrate pH controls, and gained concentrates
Liquid concentration 2.22g/100ml；Concentrate adds 20L methyl tertiary butyl ether(MTBE)s, stream plus stream plus 15% sodium carbonate liquor, is extracted,
Extraction process pH controls stand split-phase, isolated upper layer methyl tertbutyl ether solution, it is high to add 0.5% 9.5~10.0
Molecule filter aid, vacuum distillation concentration t-butyl methyl ether solution, is cooled to less than -10 DEG C crystallizations, insulated and stirred 2hr,
It is centrifugally separating to obtain the thick alkali of erythromycin.After drying gained the thick alkali of erythromycin, Erythromycin A content be 91.6%, water content 0.5% with
Under, the yield 95.8% of crystallization process Erythromycin A.
The thick alkali of 1Kg erythromycin will be obtained, adds to the glass reaction kettle of 5L, sequentially adds 2.5L absolute methanols, hydrochloric acid
Azanol 500g and sodium acid carbonate 450g, stirring and dissolving, reacts 48 hr in 30 DEG C of insulated and stirreds, then controls reaction gradient liter
Temperature, per hour raise 5 DEG C, be raised to always 60 DEG C maintain again stirring 10 it is small when, it is complete to oximation reaction, be then cooled to 10 DEG C
Hereinafter, it is separated by filtration, obtained erythromycin oximate.
Erythromycin oximate adds 10L methyl tertiary butyl ether(MTBE)s, stream plus 15% sodium carbonate liquor, is extracted, extraction process pH
Control stands split-phase, isolated upper layer methyl tertbutyl ether solution, adds 1% polymeric retention aid filtering agent mistake 9.5~10.0
Filter, vacuum distillation concentration t-butyl methyl ether solution, is cooled to less than -10 DEG C crystallizations, insulated and stirred 2hr, is centrifugally separating to obtain
Erythromycin oxime.Gained erythromycin oxime after drying, Erythromycin E oxime content are 91.8%, and erythromycin Z oxime contents are 2.6%, erythromycin
A9- oximes yield 91.8%.
Claims (11)
- A kind of 1. method that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that its processing step is：1）It is then that gained is dense by erythromycin fermentation liquid successively using ultrafiltration membrance filter plus water dialysis and NF membrane concentration Contracting liquid is extracted into organic solvent in alkaline conditions, and gained organic phase is dehydrated with adsorbent, decolorization, is depressurized afterwards dense Contracting, freezes crystallization, and filtration drying obtains the thick alkali of erythromycin；2）With polar solvent by the inorganic acid salt of the thick alkali of above-mentioned erythromycin and azanol, water miscible alkali soluble solution, oximation reaction, mistake Filter separates to obtain erythromycin oximate；3）Above-mentioned gained erythromycin oximate is extracted with organic solvent in alkaline conditions, standing separation, gained organic phase is inhaled Attached dose of dehydration, decolorization, are concentrated under reduced pressure, and freeze crystallization, and filtration drying obtains erythromycin oxime.
- 2. the method described in accordance with the claim 1 that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that mistake Journey 1）Described in erythromycin fermentation liquid before ultrafiltration membrance filter is carried out first with lye adjust pH7.5~8.5.
- 3. the method described in accordance with the claim 1 that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that mistake Journey 1）Described in ultrafiltration membrane be organic plate membrane or ceramic membrane that aperture is 5~50nm, the control of ultra-filtration process pressure 0.1~ 0.3MPa, pH7.5~8.5.
- 4. the method described in accordance with the claim 1 that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that mistake Journey 1）Described in during NF membrane concentration, filtrate pH controls are 6.5~7.5, and pressure control is 3.8MPa, and gained is dense Contracting liquid 1~3g/100ml of concentration, NF membrane are the film that molecular cut off is more than 700.
- 5. the method described in accordance with the claim 1 that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that mistake Journey 1 and process 3））Described in organic solvent be ethyl acetate, butyl acetate, amyl acetate, dichloromethane, chloroform or first Base tertbutyl ether, its dosage are 0.05~1.0 times of erythromycin fermentation liquid quality.
- 6. according to the method that erythromycin oxime is directly prepared using erythromycin fermentation liquid described in claim 1 or 2, its feature exists In, lye solution used when either reconciling pH or to control the lye used in alkaline condition be that mass concentration is 5~30% Sodium hydroxide solution, ammonia spirit or sodium carbonate liquor.
- 7. the method described in accordance with the claim 1 that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that mistake Journey 1）With process 3）Described in adsorbent be activated carbon, diatomite or polymeric retention aid filtering agent, its dosage is the 0.5 of organic phase quality ~2.0%.
- 8. the method described in accordance with the claim 1 that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that mistake Journey 2）Described in polar solvent be methanol or ethanol, its dosage is 1~5 times of the thick alkali weight of erythromycin, preferably 1.0~3.0 Times.
- 9. the method described in accordance with the claim 1 that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that mistake Journey 2）In, the thick alkali of erythromycin：The inorganic acid salt of azanol：Water miscible alkali molar ratio is=1:0.1-3.0:0.1-3.0, preferably 1: 0.1-1.0:The inorganic acid salt of 0.1-1.0, wherein azanol are hydroxylamine hydrochloride or aqueous hydroxylamine solution, and water miscible alkali is bicarbonate Sodium, sodium hydroxide or triethylamine.
- 10. the method described in accordance with the claim 1 that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that The process 2）Middle oximation reaction process is：The insulated and stirred reaction 24~48 under 6.6~6.9,30~40 DEG C of temperature conditionss of pH Hr, then controls reaction gradient heating, raises 1~5 DEG C per hour, when being raised to 55~65 DEG C always and maintaining stirring 8~12 small again, It is complete to oximation reaction, less than 10 DEG C are then cooled to, is separated by filtration to obtain erythromycin oxime.
- 11. the method described in accordance with the claim 1 that erythromycin oxime is directly prepared using erythromycin fermentation liquid, it is characterised in that Process 1）With process 3）Described in freezing crystallization refer to 2~4h of insulated and stirred under -5 DEG C~-15 DEG C temperature conditionss.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108948114A (en) * | 2018-09-06 | 2018-12-07 | 黄石世星药业有限责任公司 | One kind being applied to the impurity-removing method of 9- (E)-erythromycin oxime |
| CN112745369A (en) * | 2020-12-24 | 2021-05-04 | 宁夏启元药业有限公司 | Method for synthesizing erythromycin cyanamide by using erythromycin thiocyanate oxime |
| CN113150044A (en) * | 2021-04-28 | 2021-07-23 | 宜昌东阳光生化制药有限公司 | Purification method of erythromycin thiocyanate |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108948114A (en) * | 2018-09-06 | 2018-12-07 | 黄石世星药业有限责任公司 | One kind being applied to the impurity-removing method of 9- (E)-erythromycin oxime |
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| CN112745369A (en) * | 2020-12-24 | 2021-05-04 | 宁夏启元药业有限公司 | Method for synthesizing erythromycin cyanamide by using erythromycin thiocyanate oxime |
| CN113150044A (en) * | 2021-04-28 | 2021-07-23 | 宜昌东阳光生化制药有限公司 | Purification method of erythromycin thiocyanate |
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