CN108558908B - A kind of desalination method of ceftazidime mother liquor and the preparation method of cefotaxime - Google Patents
A kind of desalination method of ceftazidime mother liquor and the preparation method of cefotaxime Download PDFInfo
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- CN108558908B CN108558908B CN201810571646.3A CN201810571646A CN108558908B CN 108558908 B CN108558908 B CN 108558908B CN 201810571646 A CN201810571646 A CN 201810571646A CN 108558908 B CN108558908 B CN 108558908B
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- mother liquor
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B25/00—Phosphorus; Compounds thereof
- C01B25/16—Oxyacids of phosphorus; Salts thereof
- C01B25/26—Phosphates
- C01B25/30—Alkali metal phosphates
- C01B25/305—Preparation from phosphorus-containing compounds by alkaline treatment
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C1/00—Ammonia; Compounds thereof
- C01C1/24—Sulfates of ammonium
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D5/00—Sulfates or sulfites of sodium, potassium or alkali metals in general
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/12—Separation; Purification
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Cephalosporin Compounds (AREA)
Abstract
The present invention provides the preparation methods of a kind of desalination method of ceftazidime mother liquor and cefotaxime, the preparation method of cefotaxime includes by cefotaxime hydrochloride salt, ceftazidime mother liquor is obtained after generating and separating cefotaxime crystal using specific acid adjusting isoelectric point again after adjusting pH；It removes the inorganic salts in ceftazidime mother liquor: gained ceftazidime mother liquor being cooled to -5 ~ 8 DEG C, pH value is adjusted to 5.5 ~ 7.5 using inorganic base, obtains solidliquid mixture, separating inorganic salts solid and liquid；Inorganic base is at least one of sodium hydrate solid, sodium hydrate aqueous solution, sodium bicarbonate solid, sodium bicarbonate aqueous solution, sodium carbonate solid, aqueous sodium carbonate, ammonia, ammonium hydroxide.The method of the present invention is simple and easy, and equipment investment is few, can directly obtain the biggish inorganic salts solid of particle, only need solid-liquid separating equipment that can simply and efficiently remove inorganic salts from ceftazidime mother liquor, processing cost is greatly reduced, reduces environmental pollution, there is wide range of industrial applications prospect.
Description
Technical field
The present invention relates to the production technologies of cefotaxime, concretely relate to a kind of desalination method of ceftazidime mother liquor
And the preparation method of cefotaxime.
Background technique
Cefotaxime is the Third generation Cephalosporins antibiotic formulated by GlaxoSmithKline PLC company, to Grain-positive or yin
Property bacterium all have strong effect, to Pseudomonas aeruginosa, Escherichia coli, klebsiella bacillus, proteus, enterococcus, detection of Salmonella, will congratulate
Bacterium, NEISSERIA GONORRHOEAE, Neisseria meningitidis, S. aureus L-forms, hemolytic streptococcus, pneumococcus and aerobacteria etc. have strong resist
Bacterium activity, especially for Pseudomonas aeruginosa, cefotaxime is the strongest antibiotic of effect.The medical injection of cefotaxime is cephalo
His pyridine pentahydrate and sodium carbonate or arginic aseptic mixture.
In the synthesis process of cefotaxime, need to crystallize cefotaxime hydrochloride salt to obtain the production of cefotaxime target
Object generallys use sulfuric acid, hydrochloric acid etc. and adjusts isoelectric point, in this way, not only to remain a large amount of cefotaximes in ceftazidime mother liquor
Effective component and impurity, also introduce inorganic salts.The presence of inorganic salts directly affects cefotaxime effective component in mother liquor
Recycling, so that mother liquor is difficult to be recycled, if not only causing the waste of the substances such as cefotaxime directly as discharging of waste liquid,
And it will increase dramatically the cost of sewage treatment.
In the prior art, it generallys use membrane separation technique to be recycled the product in mother liquor, such as
CN101774709A discloses a kind of processing method using membrane separation technique concentration and separation ceftazidime mother liquor, on the one hand, should
Method needs to buy membrane separation plant, and it is expensive, and the solvent tolerance of film is weak, once it is remained in mother liquor organic molten
Agent then has extremely strong destructiveness to film, shortens the service life of film, increase production cost；On the other hand, mother liquor is carried out
Also it can make impurity enriched in mother liquor while concentration, then there is certain quality risk when recycling the effective component in mother liquor.
Therefore, the method for needing to develop inorganic salts in a kind of novel removal ceftazidime mother liquor, simply, efficiently to remove
Inorganic salts in mother liquor, and gained inorganic salts are recycled, save production cost.
Summary of the invention
An object of the present invention is to provide a kind of desalination method of ceftazidime mother liquor, female to solve existing cefotaxime
Liquid recovery and treatment method step is complicated, problem at high cost.
The second object of the present invention is to provide a kind of preparation method of cefotaxime, to solve the preparation of existing cefotaxime
In the process, contain inorganic salts in generated mother liquor, it is difficult to the problem of being recycled.
An object of the present invention is achieved in that
Ceftazidime mother liquor is cooled to -5 ~ 8 DEG C by a kind of desalination method of ceftazidime mother liquor, using inorganic base by pH
Value is adjusted to 5.5 ~ 7.5, obtains solidliquid mixture, separates inorganic salts solid and liquid in solidliquid mixture.
The ceftazidime mother liquor be cefotaxime hydrochloride salt is first adjusted into pH to 5.5 ~ 5.6, then using phosphoric acid,
At least one of sulfuric acid, dihydric phosphate solid or biphosphate saline solution adjust isoelectric point, generate and separate cefotaxime
Obtained solution after crystal.
Existing method can be used, cefotaxime hydrochloride is prepared, it can also be by being commercially available cefotaxime hydrochloric acid
Salt；Existing method can be used in the process that cefotaxime hydrochloride salt crystallizes obtained cefotaxime crystal.
Optionally, cefotaxime dihydrochloride is dissolved in water or other optional solvents, sodium hydroxide is added thereto, it will
PH to 5.5 ~ 5.6, then at least one of phosphoric acid, sulfuric acid, dihydric phosphate solid or biphosphate saline solution adjust etc. electricity
Point.
Preferably, the mass concentration of the phosphoric acid is 5% ~ 45%；The mass concentration of the sulfuric acid is 5% ~ 50%；The phosphoric acid
The mass concentration of dihydro saline solution is 20% ~ 50%.
Preferably, the initial pH of the ceftazidime mother liquor is 3.2 ~ 4.5.
The inorganic base be sodium hydrate solid, sodium hydrate aqueous solution, sodium bicarbonate solid, sodium bicarbonate aqueous solution,
At least one of sodium carbonate solid, aqueous sodium carbonate, ammonia, ammonium hydroxide.
Preferably, the mass concentration of the sodium hydrate aqueous solution is 5% ~ 100%；The quality of the sodium bicarbonate aqueous solution
Concentration is 5% ~ 100%；The mass concentration of the aqueous sodium carbonate is 5% ~ 100%；The mass concentration of the ammonium hydroxide be 5% ~
100%。
After the pH for adjusting ceftazidime mother liquor using inorganic base, 10 ~ 90min is stirred, solidliquid mixture is obtained.
The solidliquid mixture is separated using solid-liquid separating equipment；The solid-liquid separating equipment is centrifuge, nutsch filter, plate
Frame filter or three-in-one filter.
Gained inorganic salts solid is dried in vacuo 1 ~ 6h at 30 ~ 50 DEG C, inorganic salt powder can be obtained.
The second object of the present invention is to what is be achieved:
A kind of preparation method of cefotaxime, includes the following steps:
(a) by cefotaxime hydrochloride salt, pH to 5.5 ~ 5.6 is adjusted at 0 ~ 10 DEG C, then use phosphoric acid, sulfuric acid, phosphorus
At least one of acid dihydride salt solid or biphosphate saline solution adjust isoelectric point, after generating and separating cefotaxime crystal,
Obtain ceftazidime mother liquor；
(b) inorganic salts in ceftazidime mother liquor are removed: gained ceftazidime mother liquor in step (a) is cooled to -5 ~ 8
DEG C, pH value is adjusted to 5.5 ~ 7.5 using inorganic base, obtains solidliquid mixture, separates the inorganic salts solid in solidliquid mixture
And liquid.
In step (a), existing method can be used, cefotaxime hydrochloride is prepared, it can also be by being commercially available cephalo
His thiamine hydrochloride；Existing method can be used in the process that cefotaxime hydrochloride salt crystallizes obtained cefotaxime crystal.
Optionally, cefotaxime dihydrochloride is soluble in water, it is added sodium hydroxide thereto, then with phosphoric acid, sulfuric acid, phosphorus
At least one of acid dihydride salt solid or biphosphate saline solution adjust isoelectric point.
Preferably, the initial pH of gained ceftazidime mother liquor is 3.2 ~ 4.5.
Preferably, the mass concentration of the phosphoric acid is 5% ~ 45%；The mass concentration of the sulfuric acid is 5% ~ 50%；The phosphoric acid
The mass concentration of dihydro saline solution is 20% ~ 50%.
In step (b), the inorganic base is sodium hydrate solid, sodium hydrate aqueous solution, sodium bicarbonate solid, bicarbonate
At least one of sodium water solution, sodium carbonate solid, aqueous sodium carbonate, ammonia, ammonium hydroxide.
Preferably, the mass concentration of the sodium hydrate aqueous solution is 5% ~ 100%；The quality of the sodium bicarbonate aqueous solution
Concentration is 5% ~ 100%；The mass concentration of the aqueous sodium carbonate is 5% ~ 100%；The mass concentration of the ammonium hydroxide be 5% ~
100%。
After the pH for adjusting ceftazidime mother liquor using inorganic base, 10 ~ 90min is stirred, solidliquid mixture is obtained.
The solidliquid mixture is separated using solid-liquid separating equipment, the solid-liquid separating equipment is centrifuge, nutsch filter, plate
Frame filter or three-in-one filter.
Gained inorganic salts solid is dried in vacuo 1 ~ 6h at 30 ~ 50 DEG C, inorganic salt powder can be obtained.
Ceftazidime mother liquor desalination method of the invention can directly obtain the biggish inorganic salts solid of particle, therefore, only need
Inorganic salts can be simply and efficiently removed from ceftazidime mother liquor using conventional solid-liquid separating equipment, without utilizing film
Other separation equipments such as separation do not need to carry out the second investment to equipment, reduce production cost, simplify production technology；Desalination
Ceftazidime mother liquor afterwards, which may be recovered, applies or continues subsequent processing, significantly reduces the place of ceftazidime mother liquor
Cost is managed, is reduced environmental pollution.In addition, resulting inorganic salts solid can be used as valuable chemical intermediate, it to be used for other works
Finished product sale is made in skill, generates economic benefit, reduces production cost.
The method of the present invention is simple and easy, and equipment investment is few, has preferable economic benefit and environmental benefit, is suitble to scale
Production has extensive prospects for commercial application.
Specific embodiment
Below with reference to embodiment, the present invention is further elaborated, and following embodiments are only as explanation, not with any
Mode limits the scope of the invention.
Agents useful for same is commercially available in embodiment or is prepared by method well known within the skill of those ordinarily skilled.Following realities
Applying example realizes the purpose of the present invention.
Embodiment 1
60g cefotaxime dihydrochloride raw material is added into 90ml purified water, opens and stirs, 0 ~ 10 DEG C of temperature control, Xiang Qi
PH value is adjusted to 5.60 by middle addition sodium hydroxide, then it is brilliant that 0.06g is added to 4.5 in the phosphorus acid for adjusting pH for being 20% with mass concentration
Kind, continue the phosphoric acid tune pH to 3.75 for being 20% with mass concentration, after the separation of cefotaxime crystal, obtains 260mL cefotaxime
Mother liquor.
Initial pH=3.75 of ceftazidime mother liquor, are cooled to -5 DEG C for mother liquor, adjust pH to 5.5 with sodium hydrate solid,
90min is stirred, solidliquid mixture is obtained；Solidliquid mixture is filtered by nutsch filter, after obtaining sodium sulphate wet-milling and desalination
Mother liquor, the mother liquor after desalination can carry out recovery in the preparation process of cefotaxime, or carry out subsequent processing；By sodium phosphate
Wet-milling is placed in vacuum oven, and 50 DEG C of temperature control, dry 1h obtains sodium phosphate powder 12.3g, KF=1.5%.
Embodiment 2
Cefotaxime is prepared using the method for embodiment 1, terminal pH is 4.50, ceftazidime mother liquor 254mL is obtained, at the beginning of
Mother liquor is cooled to 0 DEG C by beginning pH=4.50, is adjusted pH to 7.5 with the aqueous sodium carbonate that mass concentration is 10%, is stirred 10min,
Obtain solidliquid mixture；Solidliquid mixture is filtered by laboratory three-in-one filter, after obtaining sodium phosphate wet-milling and desalination
Mother liquor, the mother liquor after desalination can carry out recovery in the preparation process of cefotaxime, or carry out subsequent processing；By phosphoric acid
Sodium wet-milling is placed in vacuum oven, and 45 DEG C of temperature control, dry 3h obtains sodium phosphate powder 11.7g, KF=0.66%.
Embodiment 3
Using 60g cefotaxime dihydrochloride as raw material, cefotaxime product is prepared using the method for embodiment 1, it is different
Be used in crystallization process mass concentration for 50% sulfuric acid regulation solution pH, terminal pH=3.20, by cefotaxime crystal
After separation, 226mL ceftazidime mother liquor is obtained.
Mother liquor is cooled to 8 DEG C by initial pH=3.20 of ceftazidime mother liquor, adjusts pH to 6.7 with sodium bicarbonate solid,
30min is stirred, solidliquid mixture is obtained；Solidliquid mixture is filtered by nutsch filter, after obtaining sodium sulphate wet-milling and desalination
Mother liquor, the mother liquor after desalination can carry out recovery in the preparation process of cefotaxime, or carry out subsequent processing；By sodium sulphate
Wet-milling is placed in vacuum oven, and 40 DEG C of temperature control, dry 4h obtains sodium sulfate powder 17.4g, KF=0.98%.
Embodiment 4
Ceftazidime mother liquor 233mL is obtained using the method for embodiment 1, mother liquor is cooled to 4 DEG C by initial pH=3.52,
PH to 6.7 is adjusted with the ammonium hydroxide that mass concentration is 15%, 30min is stirred, obtains solidliquid mixture；Solidliquid mixture is passed through into pumping
Filter filtering, the mother liquor after obtaining ammonium sulfate wet-milling and desalination, mother liquor after desalination can in the preparation process of cefotaxime into
Row recovery, or carry out subsequent processing；Ammonium sulfate wet-milling is placed in vacuum oven, 40 DEG C of temperature control, dry 4h obtains sulfuric acid
Ammonium powder 16.5g, KF=1.01%.
Embodiment 5
Using 60g cefotaxime dihydrochloride as raw material, cefotaxime product is prepared using the method for embodiment 1, it is different
It is the mixed solution for the sodium dihydrogen phosphate for using mass concentration to be 25% for 20% phosphoric acid and mass concentration in crystallization process, it will
After the separation of cefotaxime crystal, 241mL ceftazidime mother liquor is obtained.
Mother liquor is cooled to 2 DEG C by initial pH=4.20 of ceftazidime mother liquor, the sodium hydroxide water for being 30% with mass concentration
Solution adjusts pH to 7.0, stirs 15min, obtains solidliquid mixture；Solidliquid mixture is passed through into laboratory three-in-one filter mistake
It filters, the mother liquor after obtaining sodium phosphate wet-milling and desalination, the mother liquor after desalination can be recycled in the preparation process of cefotaxime
It applies, or carries out subsequent processing；Phosphate wet-milling is placed in vacuum oven, 45 DEG C of temperature control, dry 2h obtains sodium phosphate powder
13.1g, KF=0.77%.
Embodiment 6
Respectively in embodiment 1,2,3, desalination is forward and backward, and the residual ion in ceftazidime mother liquor is measured, gained knot
Fruit is as shown in table 1.From table 1 it follows that the zwitterion concentration after desalination in ceftazidime mother liquor is greatly reduced.
Salinity contrast table before and after 1 mother liquor desalination of table
Claims (10)
1. a kind of desalination method of ceftazidime mother liquor, which is characterized in that ceftazidime mother liquor is cooled to -5 ~ 8 DEG C, using nothing
PH value is adjusted to 5.5 ~ 7.5 by machine alkali, obtains solidliquid mixture, separates inorganic salts solid and liquid in solidliquid mixture.
2. the desalination method of ceftazidime mother liquor according to claim 1, which is characterized in that the ceftazidime mother liquor is
By cefotaxime hydrochloride salt, pH to 5.5 ~ 5.6 is first adjusted, then use phosphoric acid, sulfuric acid, dihydric phosphate solid or di(2-ethylhexyl)phosphate
At least one of hydrogen salt aqueous solution adjusts isoelectric point, generates and separates obtained solution after cefotaxime crystal.
3. the desalination method of ceftazidime mother liquor according to claim 2, which is characterized in that the ceftazidime mother liquor
Initial pH is 3.2 ~ 4.5.
4. the desalination method of ceftazidime mother liquor according to claim 1, which is characterized in that the inorganic base is hydroxide
Sodium solid, sodium hydrate aqueous solution, sodium bicarbonate solid, sodium bicarbonate aqueous solution, sodium carbonate solid, aqueous sodium carbonate, ammonia
At least one of gas, ammonium hydroxide.
5. the desalination method of ceftazidime mother liquor according to claim 4, which is characterized in that the sodium hydrate aqueous solution
Mass concentration be 5% ~ 100%；The mass concentration of the sodium bicarbonate aqueous solution is 5% ~ 100%；The aqueous sodium carbonate
Mass concentration is 5% ~ 100%；The mass concentration of the ammonium hydroxide is 5% ~ 100%.
6. the desalination method of ceftazidime mother liquor according to claim 1, which is characterized in that adjust cephalo using inorganic base
After the pH of his pyridine mother liquor, 10 ~ 90min is stirred, solidliquid mixture is obtained.
7. the desalination method of ceftazidime mother liquor according to claim 1, which is characterized in that using solid-liquid separating equipment point
From the solidliquid mixture, the solid-liquid separating equipment is centrifuge, nutsch filter, plate filter or three-in-one filter.
8. the desalination method of ceftazidime mother liquor according to claim 1, which is characterized in that gained inorganic salts solid exists
It is dried in vacuo 1 ~ 6h at 30 ~ 50 DEG C, inorganic salt powder can be obtained.
9. a kind of preparation method of cefotaxime, which comprises the steps of:
(a) by cefotaxime hydrochloride salt, pH to 5.5 ~ 5.6 is adjusted at 0 ~ 10 DEG C, then use phosphoric acid, sulfuric acid, di(2-ethylhexyl)phosphate
At least one of hydrogen salt solid or biphosphate saline solution adjust isoelectric point to obtain after generating and separating cefotaxime crystal
Ceftazidime mother liquor；
(b) inorganic salts in ceftazidime mother liquor are removed: gained ceftazidime mother liquor in step (a) being cooled to -5 ~ 8 DEG C, is adopted
PH value is adjusted to 5.5 ~ 7.5 with inorganic base, obtains solidliquid mixture, separates inorganic salts solid and liquid in solidliquid mixture
Body.
10. the preparation method of cefotaxime according to claim 9, which is characterized in that in step (b), the inorganic base
For sodium hydrate solid, sodium hydrate aqueous solution, sodium bicarbonate solid, sodium bicarbonate aqueous solution, sodium carbonate solid, sodium carbonate
At least one of solution, ammonia, ammonium hydroxide.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101774709A (en) * | 2010-01-21 | 2010-07-14 | 济南大学 | Treating method of ceftazidime mother liquor |
| CN107722040A (en) * | 2017-10-10 | 2018-02-23 | 南京志坤环保科技有限公司 | A kind of membrane separating method and device for recycling ceftazidime mother liquor |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101774709A (en) * | 2010-01-21 | 2010-07-14 | 济南大学 | Treating method of ceftazidime mother liquor |
| CN107722040A (en) * | 2017-10-10 | 2018-02-23 | 南京志坤环保科技有限公司 | A kind of membrane separating method and device for recycling ceftazidime mother liquor |
Non-Patent Citations (1)
| Title |
|---|
| 头孢他啶的合成工艺改进;郑玉林;《中国药物化学杂志》;20100630;第20卷(第3期);第198-200页 * |
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