CN105622617A - Method for performing clean recovery on sildenafil citrate mother liquor - Google Patents
Method for performing clean recovery on sildenafil citrate mother liquor Download PDFInfo
- Publication number
- CN105622617A CN105622617A CN201610191341.0A CN201610191341A CN105622617A CN 105622617 A CN105622617 A CN 105622617A CN 201610191341 A CN201610191341 A CN 201610191341A CN 105622617 A CN105622617 A CN 105622617A
- Authority
- CN
- China
- Prior art keywords
- mother liquor
- sildenafil citrate
- carried out
- sildenafil
- cleaning recovery
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
The invention provides a method for performing clean recovery on a sildenafil citrate mother liquor. Based on a production process in the prior art, the method comprises the steps of concentrating and separating a primary crystallization mother liquor by using a nanofiltration membrane to obtain a concentrated liquid; separating the concentrated liquid to obtain an initial reaction material-sildenafil, wherein the content of sildenafil reaches 99.80% and the purity of sildenafil reaches 99.97%; and directly discharging a residual nanofiltration dialysis fluid into a rectifying tower, and recovering an organic solvent-ethanol through a vapor permeation membrane. According to the clean environment-friendly recycling process for the sildenafil citrate mother liquor, the difficult problem in nearly 100% recycling of the initial material-sildenafil is solved, the heavy environmental protection burden of production enterprises is eliminated, the potential considerable economic benefits are brought for producers, and very high economic and social values are achieved.
Description
Technical field
The invention belongs to field of pharmaceutical chemistry technology, more specifically, it relates to a kind of method that sildenafil citrate mother liquor is carried out cleaning recovery.
Background technology
Sildenafil citrate (Sildenafilcitrate); chemistry 5-[2-oxyethyl group-5-(4-methylpiperazine-1-base alkylsulfonyl) phenyl]-1-methyl-3-n-propyl-1 by name; 6-bis-hydrogen-7H-pyrazoles [4; 3-d] pyrimidine-7 ketone citrate is the selective depressant of V-type cGMP phosphodiesterase in human corpus cavernosum. Sildenafil citrate, as oral medicine, can effectively treat erection problem, and it has obtained good effect for clinical.
Existing sildenafil citrate synthesis technique, generally speaking can be summarized as following two kinds:
One is through dioxide giving, sulfonating chlorinating, sulfuryl amine, salt obtains sildenafil citrate with becoming with 2-ethoxy benzoyl chloride and compound 4-[2-ethoxy benzamide base]-1-methyl-3-n-propyl-5-methane amide. The receipts rate of condensation and sulfuryl amine respectively only 40% and 49% in this synthesis technique, and condensation and ring close product and all need chromatographic separation, therefore there is the shortcoming that total recovery is low and material consumption is high in whole bar route;
Two is closed with 4-[2-ethoxy benzamide base]-1-methyl-3-n-propyl-5-methane amide condensation, ring through sulfonating chlorinating, sulfuryl amine by 2-ethoxybenzoic acid again and become salt to obtain sildenafil citrate. In order to improve the receipts rate according to this synthetic method synthetic product and purity; application number is 201410620801.8, name is called in the patent application of " preparation method of sildenafil citrate "; by thionyl chloride in chlorosulfonation etc.; chemically improve receipts rate and the purity of product; but cannot realizing carrying out the effective constituent in mother liquor economic environmental protection recovery, energy-efficientization that more cannot realize organic solvent in mother liquor reclaims.
Therefore, above-mentioned two kinds of synthetic routes are existence process defect in last one-tenth salt step all, in mother liquor, Virga and Citric Acid part are dissociated, this can cause the reduction of product yield, and in the waste water produced in manufacture process containing too much organic substance thus cause the pollution of environment, as adopted traditional treatment process almost cannot have the Virga of economic worth by efficient recovery, organic solvent ethanol in mother liquor also cannot carry out the recovery of economical and effective, also can increase environmental protection of enterprise burden simultaneously.
In order to overcome the above-mentioned defect existing for prior art, this invention of special proposition.
Summary of the invention
It is an object of the invention to the effective constituent Virga in the mother liquor for sildenafil citrate synthesis technique and a kind of organic solvent ethanol carries out economy, environmental protection, efficient recovery are applied mechanically method that sildenafil citrate mother liquor is carried out cleaning recovery.
In order to realize above-mentioned purpose, the technical solution adopted in the present invention is:
Sildenafil citrate mother liquor is carried out a method for cleaning recovery, comprises the steps:
(A) starting raw material needed for synthesis sildenafil citrate is synthesized sildenafil citrate in retort, obtain reacting rear mother liquor after question response is complete;
(B) mother liquor plate-and-frame filter press after the reaction of step (A) gained is filtered, obtain clear mother liquor;
(C) by after the clear mother liquor adjust ph of step (B) gained, enter nanofiltration membrane component 6 and process, then obtain concentrated mother liquor and mother liquor dialyzate through separation;
(D) when the concentrated mother liquor concentration obtained when step (C) reaches 10mg��25mg/mL, moved into container for storing liquid, and container for storing liquid is placed refrigerating chamber and preserves;
(E) by concentrated mother liquor adjust ph to 3.5��6.5 in container for storing liquid, and control temperature is at 5-15 DEG C, obtains reaction raw materials Virga solid;
(F) the mother liquor dialyzate that step (C) obtains is carried out infiltration evaporation and reclaims ethanol wherein.
In the present invention, infiltration evaporation described in step (F) reclaims ethanol wherein and comprises:
A described mother liquor dialyzate is first sent into by () in the middle part of rectifying tower 1, obtaining mass percent concentration from the discharge port of rectifying tower 1 is 70��90% organic solutions;
B mass percent concentration that step (a) is obtained by () is that 70��90% organic solutions are first through superheater 2, water vapour penetration is carried out again by the vapor permeable membrane module 3 of dewatering system, retain side material through condenser 4, the final ethanol obtaining mass percent concentration and being greater than 99.0%.
In the present invention, in step (C), the concentration of described clear mother liquor is 0.3��0.8mg/mL.
In the present invention, step (C) enters nanofiltration membrane component 6 when processing, the temperature of described nanofiltration membrane 15��35 DEG C.
In the present invention, the molecular weight cut-off of nanofiltration membrane is 400��600Da, and nanofiltration membrane surface lotus is positive electricity, bear electricity or electric neutrality.
In the present invention, water from diffusion is added in the side that retains of nanofiltration membrane so that diafiltration multiple is 0��20 times of described clear mother liquor.
In the present invention, nanofiltration membrane component 6 is rolled membrane module or tubular membrane component, is selected from crosslinked fully aromatic polyamide film (APA).
In the present invention, nanofiltration membrane component 6 carries out working pressure when nanofiltration is purified and, for entering pressure 6��35bar, goes out pressure 3��32bar.
In the present invention, the position of rectifying tower 1 side line discharge is in the profit reduction and reserving section height of rectifying tower 1.
In the present invention, described mass percent concentration is after 70��90% organic solutions are warming up to 40��100 DEG C by step (b), reheats to 80��150 DEG C, then carry out water vapour penetration by the vapor permeable membrane module (3) of dewatering system.
In the present invention, the gauge pressure of vapor permeable membrane module 4 feed side is 0��0.8MPa, and the gauge pressure of per-meate side is 50��10000Pa; Vapor permeable membrane module 4 is rolled membrane module or tubular membrane component, is selected from permeable type molecular screen membrane (NaA).
A kind of method that sildenafil citrate mother liquor carries out cleaning recovery provided by the present invention, on the basis of existing technology, adds mother liquor nanofiltration removal of impurities operation and dialyzate organic solvent vapor permeable recovery process. The introducing of these two technology, solves the economy of effective constituent Virga in the sildenafil citrate mother liquor of synthesis, problem that environmental protection, high efficiente callback are applied mechanically; Also solve the economy of organic solvent ethanol in dialyzate simultaneously, problem that environmental protection, high efficiente callback are applied mechanically. Compared with prior art, keep carrying out at low temperatures due to nanofiltration membrane treatment process, thus avoid chemical substance as far as possible to decompose because of high temperature, and ensure that and do not undergo phase transition at concentration process, and while concentrated, the inorganic salt such as the organism of small-molecular-weight and sodium-chlor can pass through film, thus decrease the accumulation of impurity in concentrated solution, it is to increase the recovery that the purity of reactant Virga and concentration are next step offers convenience. The process of dialyzate is compared with traditional technology, the azeotrope that traditional technology utilizes alcohol-water to be formed in rectifying tower dewaters, there is the problem that the rate of recovery is low, purity is low and energy consumption is high, and infiltration evaporation film device can a step dewater to chemical pure rank, and there is simple to operate, rate of recovery height and the low advantage of energy consumption. A kind of method that sildenafil citrate mother liquor carries out cleaning recovery provided by the invention, sildenafil citrate can reach more than 99.5% through purity HPLC detection, and the purity of ethanol can reach more than 99.5% through GC detection, all meets country's pharmacy corporation requirement.
Accompanying drawing explanation
Fig. 1 utilizes nanofiltration membrane system to carry out the process flow sheet of removal of impurities in the present invention
Fig. 2 utilizes infiltration evaporation system to carry out the process flow sheet dewatered in the present invention
Embodiment
Embodiment 1
Sildenafil citrate mother liquor is carried out a method for cleaning recovery, specifically comprises the steps
(A) starting raw material needed for synthesis sildenafil citrate is synthesized sildenafil citrate in retort, obtain reacting rear mother liquor 500L after question response is complete;
(B) mother liquor plate-and-frame filter press after the reaction of step (A) gained is filtered, obtain clear mother liquor, and mechanical impurity;
(C) as the clear mother liquid concentration 0.3��0.8mg/mL described in step (B), temperature is within the scope of 10��15 DEG C, regulating its pH value to 4��5, then enter nanofiltration membrane component 6 and remove a large amount of impurity and calcium ions and magnesium ions, separation obtains concentrated mother liquor and mother liquor dialyzate;
(D) when the concentrated mother liquor concentration obtained when step (C) reaches 10mg��25mg/mL, moved into container for storing liquid, and container for storing liquid is placed refrigerating chamber and preserves;
(E) by concentrated mother liquor adjust ph to 3.5��6.5 in container for storing liquid, and control temperature is at 5-15 DEG C, obtains reaction raw materials Virga solid; In Virga solid, Virga content reaches 99.80% after testing, and purity is 99.97%;
(F) the mother liquor dialyzate that step (C) obtains is entered rectifying tower and organic solvent ethanol in mother liquor is carried out infiltration evaporation recovery; Specifically comprising: mother liquor dialyzate is first sent into by (a) by feedstock pump in the middle part of rectifying tower 1, obtaining mass percent concentration from the discharge port of rectifying tower 1 is 70��75% organic solutions; B mass percent concentration that step (a) is obtained by () is that 70��75% organic solutions first heat up through superheater 2, after being first warming up to 40 DEG C, reheat to 80 DEG C, then carry out water vapour penetration by the vapor permeable membrane module 3 of dewatering system. Vapor permeable membrane retain side gauge pressure 0.8MPa, per-meate side absolute pressure 1500Pa, retain side material through condenser 4, the final high purity ethanol solvent obtaining mass percent concentration and being greater than 99.5%.
Embodiment 2
Sildenafil citrate mother liquor is carried out a method for cleaning recovery, specifically comprises the steps
(A) starting raw material needed for synthesis sildenafil citrate is synthesized sildenafil citrate in retort, obtain reacting rear mother liquor 500L after question response is complete;
(B) mother liquor plate-and-frame filter press after the reaction of step (A) gained is filtered, obtain clear mother liquor, and mechanical impurity;
(C) as the clear mother liquid concentration 0.8��1.0mg/mL described in step (B), temperature is within the scope of 15��20 DEG C, regulating its pH value to 5��6, then enter nanofiltration membrane component 6 and remove a large amount of impurity and calcium ions and magnesium ions, separation obtains concentrated mother liquor and mother liquor dialyzate;
(D) when the concentrated mother liquor concentration obtained when step (C) reaches 10mg��25mg/mL, moved into container for storing liquid, and container for storing liquid is placed refrigerating chamber and preserves;
(E) by concentrated mother liquor adjust ph to 3.5��6.5 in container for storing liquid, and control temperature is at 5-15 DEG C, obtains reaction raw materials Virga solid; In Virga solid, Virga content reaches 99.82% after testing, and purity is 99.97%;
(F) the mother liquor dialyzate that step (C) obtains being entered rectifying tower and organic solvent ethanol in mother liquor is carried out infiltration evaporation recovery: specifically comprise: mother liquor dialyzate is first sent into by feedstock pump by (a) in the middle part of rectifying tower 1, obtaining mass percent concentration from the discharge port of rectifying tower 1 is 75��80% organic solutions; B mass percent concentration that step (a) is obtained by () is that 75��80% organic solutions first heat up through superheater 2, first it is warming up to 90 DEG C, reheat to 150 DEG C, then carry out water vapour penetration by the vapor permeable membrane module (3) of dewatering system. Vapor permeable membrane retain side gauge pressure 0.6MPa, per-meate side absolute pressure 1000Pa, retain side material through condenser 4, the final high purity ethanol solvent obtaining mass percent concentration and being greater than 99.5%.
Embodiment 3
Sildenafil citrate mother liquor is carried out a method for cleaning recovery, specifically comprises the steps
(A) starting raw material needed for synthesis sildenafil citrate is synthesized sildenafil citrate in retort, obtain reacting rear mother liquor 500L after question response is complete;
(B) mother liquor plate-and-frame filter press after the reaction of step (A) gained is filtered, obtain clear mother liquor, and mechanical impurity;
(C) as the clear mother liquid concentration 0.8��1.0mg/mL described in step (B), temperature is within the scope of 20��25 DEG C, regulating its pH value to 6��7, then enter nanofiltration membrane component 6 and remove a large amount of impurity and calcium ions and magnesium ions, separation obtains concentrated mother liquor and mother liquor dialyzate;
(D) when the concentrated mother liquor concentration obtained when step (C) reaches 10mg��25mg/mL, moved into container for storing liquid, and container for storing liquid is placed refrigerating chamber and preserves;
(E) by concentrated mother liquor adjust ph to 3.5��6.5 in container for storing liquid, and control temperature is at 5-15 DEG C, obtains reaction raw materials Virga solid; In Virga solid, Virga content reaches 99.8% after testing, and purity is 99.91%;
(F) the mother liquor dialyzate that step (C) obtains is entered rectifying tower and organic solvent ethanol in mother liquor is carried out infiltration evaporation recovery; Specifically comprising: mother liquor dialyzate is first sent into by (a) by feedstock pump in the middle part of rectifying tower 1, obtaining mass percent concentration from the discharge port of rectifying tower 1 is 70��75% organic solutions; B mass percent concentration that step (a) is obtained by () is that 70��75% organic solutions first heat up through superheater 2, after being first warming up to 100 DEG C, reheat to 130 DEG C, water vapour penetration is carried out again by the vapor permeable membrane module 3 of dewatering system, vapor permeable membrane retain side gauge pressure 0.5MPa, per-meate side absolute pressure 500Pa, retains side material through condenser 4, the final high purity ethanol solvent obtaining mass percent concentration and being greater than 99.5%.
Claims (10)
1. sildenafil citrate mother liquor is carried out the method for cleaning recovery by one kind, it is characterised in that, described method comprises the steps:
(A) starting raw material needed for synthesis sildenafil citrate is synthesized sildenafil citrate in retort, obtain reacting rear mother liquor after question response is complete;
(B) mother liquor plate-and-frame filter press after the reaction of step (A) gained is filtered, obtain clear mother liquor;
(C) after the clear mother liquor adjust ph of step (B) gained, nanofiltration membrane component (6) will be entered and process, then obtain concentrated mother liquor and mother liquor dialyzate through separation;
(D) when the concentrated mother liquor concentration obtained when step (C) reaches 10mg��25mg/mL, moved into container for storing liquid, and container for storing liquid is placed refrigerating chamber and preserves;
(E) by concentrated mother liquor adjust ph to 3.5��6.5 in container for storing liquid, and control temperature is at 5-15 DEG C, obtains reaction raw materials Virga solid;
(F) the mother liquor dialyzate that step (C) obtains is carried out infiltration evaporation and reclaims ethanol wherein.
2. a kind of method that sildenafil citrate mother liquor is carried out cleaning recovery according to claim 1, it is characterised in that, the infiltration evaporation described in step (F) reclaims ethanol wherein and comprises:
A described mother liquor dialyzate is first sent into by () from rectifying tower (1) middle part, obtaining mass percent concentration from the discharge port of rectifying tower (1) is 70��90% organic solutions;
B mass percent concentration that step (a) is obtained by () is that 70��90% organic solutions are first through superheater (2), water vapour penetration is carried out again by the vapor permeable membrane module (3) of dewatering system, retain side material through condenser (4), the final ethanol obtaining mass percent concentration and being greater than 99.0%.
3. a kind of method that sildenafil citrate mother liquor is carried out cleaning recovery according to claim 1, it is characterized in that, in step (C), the concentration of described clear mother liquor is 0.3��0.8mg/mL, and enter nanofiltration membrane component (6) when processing, the temperature of described nanofiltration membrane 15��35 DEG C.
4. according to a kind of described in any one in claim 1-3, sildenafil citrate mother liquor is carried out the method for cleaning recovery, it is characterized in that, described nanofiltration membrane component (6) is rolled membrane module or tubular membrane component, and nanofiltration membrane is crosslinked fully aromatic polyamide film.
5. a kind of method that sildenafil citrate mother liquor is carried out cleaning recovery according to claim 4, it is characterised in that, the molecular weight cut-off of described nanofiltration membrane is 400��600Da, and nanofiltration membrane surface lotus is positive electricity, bear electricity or electric neutrality.
6. sildenafil citrate mother liquor is carried out the method for cleaning recovery by a kind of according to claim 1 or 4, it is characterised in that, water from diffusion is added in the side that retains of described nanofiltration membrane so that diafiltration multiple is 0��20 times of described clear mother liquor.
7. a kind of method that sildenafil citrate mother liquor is carried out cleaning recovery according to claim 1, it is characterised in that, described nanofiltration membrane component (6) carries out working pressure when nanofiltration is purified and, for entering pressure 6��35bar, goes out pressure 3��32bar.
8. a kind of method that sildenafil citrate mother liquor is carried out cleaning recovery according to claim 2, it is characterised in that: the position of rectifying tower (1) side line discharge is in the profit reduction and reserving section height of rectifying tower (1).
9. a kind of method that sildenafil citrate mother liquor is carried out cleaning recovery according to claim 2, it is characterized in that, described mass percent concentration is after 70��90% organic solutions are warming up to 40��100 DEG C by step (b), reheat to 80��150 DEG C, then carry out water vapour penetration by the vapor permeable membrane module (3) of dewatering system.
10. a kind of method that sildenafil citrate mother liquor is carried out cleaning recovery according to claim 1, it is characterised in that, the gauge pressure of vapor permeable membrane module (4) feed side is 0��0.8MPa, and the gauge pressure of per-meate side is 50��10000Pa; Vapor permeable membrane module is rolled membrane module or tubular membrane component, is selected from permeable type molecular screen membrane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610191341.0A CN105622617B (en) | 2016-03-30 | 2016-03-30 | A method of sildenafil citrate mother liquor is subjected to cleaning recycling |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610191341.0A CN105622617B (en) | 2016-03-30 | 2016-03-30 | A method of sildenafil citrate mother liquor is subjected to cleaning recycling |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105622617A true CN105622617A (en) | 2016-06-01 |
| CN105622617B CN105622617B (en) | 2018-09-11 |
Family
ID=56037999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610191341.0A Active CN105622617B (en) | 2016-03-30 | 2016-03-30 | A method of sildenafil citrate mother liquor is subjected to cleaning recycling |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105622617B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109867677A (en) * | 2017-12-04 | 2019-06-11 | 广州白云山医药集团股份有限公司白云山化学制药厂 | A kind of method that recycling prepares silaenafil |
| CN113072566A (en) * | 2021-03-03 | 2021-07-06 | 内蒙古常盛制药有限公司 | Process for recovering 6-APA and salt from 6-APA mother liquor by two-stage membrane method |
Citations (4)
| 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 |
| CN104370915A (en) * | 2014-11-06 | 2015-02-25 | 成都医路康医学技术服务有限公司 | Preparation method of sildenafil citrate |
| CN104370978A (en) * | 2014-12-08 | 2015-02-25 | 山东润德生物科技有限公司 | Method and device for extracting D-ribose from D-ribose crystalline mother solution |
| CN104557605A (en) * | 2013-10-12 | 2015-04-29 | 宁夏启元药业有限公司 | Method for recovering tetracycline from tetracycline crystallization mother liquor |
-
2016
- 2016-03-30 CN CN201610191341.0A patent/CN105622617B/en active Active
Patent Citations (4)
| 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 |
| CN104557605A (en) * | 2013-10-12 | 2015-04-29 | 宁夏启元药业有限公司 | Method for recovering tetracycline from tetracycline crystallization mother liquor |
| CN104370915A (en) * | 2014-11-06 | 2015-02-25 | 成都医路康医学技术服务有限公司 | Preparation method of sildenafil citrate |
| CN104370978A (en) * | 2014-12-08 | 2015-02-25 | 山东润德生物科技有限公司 | Method and device for extracting D-ribose from D-ribose crystalline mother solution |
Non-Patent Citations (4)
| Title |
|---|
| 冯骉: "《膜分离的工程与应用》", 28 February 2006 * |
| 周正立: "《反渗透水处理应用技术及膜水处理剂》", 30 June 2005 * |
| 曹学君等: "膜分离技术在医药工业中的应用", 《国外医药抗生素分册》 * |
| 白雪杉: "渗透汽化回收制药废液中异丙醇", 《过滤与分离》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109867677A (en) * | 2017-12-04 | 2019-06-11 | 广州白云山医药集团股份有限公司白云山化学制药厂 | A kind of method that recycling prepares silaenafil |
| CN113072566A (en) * | 2021-03-03 | 2021-07-06 | 内蒙古常盛制药有限公司 | Process for recovering 6-APA and salt from 6-APA mother liquor by two-stage membrane method |
| CN113072566B (en) * | 2021-03-03 | 2023-08-01 | 内蒙古常盛制药有限公司 | Process for recovering 6-APA and salt from 6-APA mother liquor by two-stage membrane method |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105622617B (en) | 2018-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| He et al. | Experimental study on the rejection of salt and dye with cellulose acetate nanofiltration membrane | |
| CN107628930B (en) | Energy-saving process for separating methanol, isopropanol and water by heat pump extractive distillation | |
| JP2018520874A (en) | Reverse osmotic pressure method without osmotic pressure to concentrate solute-containing aqueous solution to high concentration | |
| CN105218317B (en) | The method and device that ethanol is reclaimed in a kind of hexanitrobibenzyl production | |
| Lopez et al. | Separation of organic acids from water using ionic liquid assisted electrodialysis | |
| BR112012010194B1 (en) | PROCESS FOR PRODUCTION OF XYLOSIS BY BIOMASS HYDROLYSIS OF TROPICAL FRUIT WITH SULFURIC ACID | |
| CN106517632A (en) | Concentration device and method for reverse osmosis membrane concentrated ammonium nitrate waste water | |
| CN108658785A (en) | The separation method of difficult separation system containing triethylamine | |
| CN105622617A (en) | Method for performing clean recovery on sildenafil citrate mother liquor | |
| CN101607890B (en) | Method for continuously neutralizing and extracting citric acid | |
| CN108659061A (en) | A kind of purification processing method of Sucralose crystalline mother solution | |
| CN104926690A (en) | Method and device for recycling and refining acetonitrile in ceftriaxone sodium synthesis | |
| CN104109078A (en) | Method for recovering ethanol in analginum production | |
| CN102336650B (en) | Stripping process and device for removing organic impurities in brufen sodium salt | |
| CN102344383B (en) | Method for concentrating and crystallizing L-phenylalanine | |
| Zeng et al. | A pervaporation-crystallization (PC) process for simultaneous recovery of ethanol and sodium pyruvate from waste centrifugal mother liquid | |
| CN104844420B (en) | The continuous treatment technique of neopentyl glycol condensation water cleaning mother liquor and device | |
| CN107721033A (en) | The system and method for handling salt solution | |
| CN107973711A (en) | A kind of method of Simulation moving bed separating glucose acid mother liquid of sodium | |
| CN106588641A (en) | Method for reclaiming primary crystallized mother liquor of gulonic acid | |
| CN204933271U (en) | A kind of succinic acid fermentation liquor separation and purification device | |
| CN209790924U (en) | strong brine crystallization system | |
| CN106117012B (en) | A kind of separation and recovery method of the dense room liquid of zymotic fluid electrodialysis desalination | |
| CN101195594A (en) | Production method of extracting active ingredient from wastewater of producing tobias acid | |
| CN105348043A (en) | Separating and recycling method and device for solvent-water mixture containing impurities prone to scale formation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |