CN106831894A - A kind of method that deacetylation Coupling Adsorption separates D aminoglucose hydrochlorides - Google Patents
A kind of method that deacetylation Coupling Adsorption separates D aminoglucose hydrochlorides Download PDFInfo
- Publication number
- CN106831894A CN106831894A CN201611227841.1A CN201611227841A CN106831894A CN 106831894 A CN106831894 A CN 106831894A CN 201611227841 A CN201611227841 A CN 201611227841A CN 106831894 A CN106831894 A CN 106831894A
- Authority
- CN
- China
- Prior art keywords
- minutes
- acid
- adsorption
- exchange resin
- glucosamines
- 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
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention provides a kind of method that deacetylation Coupling Adsorption separates D aminoglucose hydrochlorides; it is the acetyl group and adsorbing separation D aminoglucose hydrochlorides that the solution containing N acetyl D Glucosamines is removed N acetyl D Glucosamines after pre-treatment by being filled with the deacetylation adsorption separation device of cationic ion-exchange resin, under certain condition.The present invention instead of traditional hydrochloric acid water and frees acetyl group using the acetyl group and adsorbing separation D Glucosamine techniques of advanced removing N acetyl D Glucosamines, and condensing crystallizing separates D aminoglucose hydrochloride techniques.It is that good product quality, extract yield is high using the advantage of this method production D aminoglucose hydrochlorides, supplementary product onsumption is low, easy to operate, and environmental pollution is small.
Description
Technical field
The present invention relates to the preparation technology of D-Glucosamine Hydrochloride, specifically, it is related to a kind of deacetylation to couple
The method of adsorbing separation D-Glucosamine Hydrochloride.
Background technology
D- Glucosamines, are compounds that a hydroxyl of glucose is replaced by an amino.Molecular formula C6H13O5N,
Amino sugar, abbreviation ammonia sugar, also known as gucosamine are commonly called as, are widely present in nature.
Chemical structural formula is：
Health care and therapeutic action of the D- Glucosamines to Bones and joints have obtained the U.S., Europe and day the nineties in last century
This medical field recognizes, and ratifies it in succession as health product and marketing drugs.So far, in the Bones and joints of countries in the world listing
Most of health food all with the addition of D- Glucosamines.
Current domestic production producer mainly uses dried small shrimp crab shell Hydrolyze method and Production by Microorganism Fermentation.The defect of Hydrolyze method
Mainly include：1st, there is the anaphylactoid patient of aquatic products to many from the D- ammonia sugar hydrochloride that the aquatic products such as dried small shrimp crab shell are extracted
It is inapplicable；2nd, purifying process is complicated, and product has a fish like smell, unstable；3rd, influenceed by environmental pollution, ammonia sugar is extracted from shrimp and crab shells
Hydrochloride, inevitably by heavy metal pollution；4th, production is limited larger by raw material, it is difficult to which industrialization is extensive raw
Produce, product is also difficult to enter high-end market；5th, need to use substantial amounts of concentrated hydrochloric acid in producing, environmental protection pressure is huge.
Microbe fermentation method obtains zymotic fluid with glucose as raw material through microbial fermentation, and zymotic fluid is obtained after treatment
D- glucosamine products.Because the microorganism used in fermentation process is to the problem of resistance of D- Glucosamines, fermentation
At the end of in zymotic fluid D- Glucosamines exist in the form of 2-acetylamino-2-deoxy-D-glucose.
Current fermentation method D- Glucosamines extractive technique generally uses hydrochloric acid water solution deacetylation technique, in production process
Substantial amounts of diluted acid is produced, including the acetic acid that the reactant hydrochloric acid and deacetylation for adding are produced.Because containing certain proportion
Acetic acid, diluted acid can not return to the recycling that the deacetylated operation of hydrolysis realizes hydrochloric acid.
Such as using diluted acid as waste water, due to wherein containing hydrochloric acid and acetic acid, pH value is low, injures huge to environmentally friendly microorganism,
Diluted acid cannot be directly entered environment-friendly disposal system and be processed.Using environment friendly system is entered after alkali neutralisation treatment, because introducing
Inorganic cation, the total salt of waste water does not reach the emission request of national regulation again.Such as processed using neutralization-evaporation technology, because dilute
Acid is the mixed aqueous solution of hydrochloric acid and acetic acid, the purity of neutralizations-evaporation process afterchlorinate thing and acetate do not reach crystallize it is pure
Degree, it is impossible to crystallize out single component, the salt organic waste water highly concentrated, high after concentration still cannot be processed.
The content of the invention
The purpose of the present invention is directed to current fermentation method production D- Glucosamines and there is environmental pollution greatly, and technique is cumbersome,
The defect of high energy consumption, solves the technological difficulties that 2-acetylamino-2-deoxy-D-glucose deacetylation and D- Glucosamines are separate, there is provided
A kind of simplicity, low stain, the method for preparing D-Glucosamine Hydrochloride in high yield, inexpensive.
In order to realize the object of the invention, a kind of deacetylation Coupling Adsorption that the present invention is provided separates D- glucosamine salts
The method of hydrochlorate, comprises the following steps：
S1, will contain 2-acetylamino-2-deoxy-D-glucose solution after pre-treatment removal of impurities liquid；
S2, removal of impurities liquid are obtained being adsorbed with the saturated resin of D- Glucosamines and contained through cationic exchange resin adsorption
The raffinate phase of acetic acid, washes resin column with water, then uses inorganic acid desorption, obtains the extraction containing D-Glucosamine Hydrochloride
Phase；
S3, extract and mutually post-treated obtain D-Glucosamine Hydrochloride finished product.
Solution containing 2-acetylamino-2-deoxy-D-glucose of the present invention can be using any second containing N- disclosed in prior art
The solution of acyl-D- Glucosamines.For example, the grape of acetyl-D-amino containing N- obtained by microbe fermentation method or enzyme transforming process
The solution of sugar.
Cationic ion-exchange resin described in step S2 is selected from storng-acid cation exchange resin or Subacidity cation is exchanged
Resin, preferably storng-acid cation exchange resin.
Absorption is carried out at a temperature of 50 DEG C -150 DEG C described in step S2, preferably 75 DEG C -98 DEG C.
The total reaction time of adsorption and desorption is -600 minutes 20 minutes, preferably -300 minutes 120 minutes in step S2.
Inorganic acid described in step S2 is selected from hydrochloric acid, sulfuric acid or phosphoric acid etc., and the concentration of the inorganic acid is 2%-60%.Nothing
H in machine acid+It is 1 with the mol ratio of 2-acetylamino-2-deoxy-D-glucose in removal of impurities liquid:0.9-10.
The total reaction time of adsorption and desorption is -600 minutes 20 minutes, preferably -300 minutes 120 minutes in step S2.
Pretreatment mode described in step S1 is selected from heating, sedimentation, filtering, decolouring, desalination, concentration, crystallization, centrifugation etc.
At least one.
Post processing mode described in step S3 is selected from and decolourizes, filters, concentrating, crystallizing, being centrifuged, drying at least the one of centering
Kind.
The present invention is using the advanced acetyl group and adsorbing separation D- Glucosamines for removing 2-acetylamino-2-deoxy-D-glucose
Technique instead of traditional hydrochloric acid water and free acetyl group, and condensing crystallizing separates D-Glucosamine Hydrochloride technique.Using this method
The advantage for producing D-Glucosamine Hydrochloride is that good product quality, extract yield is high, and supplementary product onsumption is low, easy to operate, ring
Border pollution is small.
Specific embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.If not specializing, embodiment
In the conventional meanses that are well known to those skilled in the art of technological means used, it is raw materials used to be commercial goods.
The method that the deacetylation Coupling Adsorption of embodiment 1 separates D-Glucosamine Hydrochloride
Methods described is comprised the following steps that：
1st, it is the zymotic fluid of 98g/L by content containing 2-acetylamino-2-deoxy-D-glucose after 200L heat inactivations, is using aperture
The ceramic membrane filter of 5nm, pure water dialysis membrane concentrated phase obtains the filter liquor 240L that content is 80.5g/L；
2nd, 240L ceramic membrane filter liquors are pumped into and is filled with H+Type storng-acid cation exchange resin (Jiangsu Su Qing water process
Engineering Group Co., Ltd production D001 storng-acid cation exchange resins) deacetylated adsorption separation device, material dress
The middle reaction time is put for 240 minutes, reaction temperature is 90 DEG C.The resin of pure water adsorption saturation, the absorption of 12% resolving hydrochloric acid
D- Glucosamines (H in resin+It is 1 with the mol ratio of 2-acetylamino-2-deoxy-D-glucose:0.9-10), ammonia containing D- is obtained
Base glucose hydrochloride salinity is the extraction phase 86L of 220g/L, and the raffinate phase containing acetic acid；
3rd, 0.2% activated carbon is added in extracting phase to 86L, 50 DEG C of insulations are filtered after 60 minutes, and pure water filter cake is obtained
Concentration is the destainer 90L of 210g/L；
4th, 90L destainers it is concentrated, crystallization, centrifugation, drying and processing, obtain the D- glucosamine hydrochloric acids of purity 99.2%
Salt 15450g, and concentration is the mother liquor 8.1L of 356g/L.
The yield of gained D-Glucosamine Hydrochloride is 94.89% in the present embodiment.
The method that the deacetylation Coupling Adsorption of embodiment 2 separates D-Glucosamine Hydrochloride
Methods described is comprised the following steps that：
1st, it is the zymotic fluid of 95g/L by content containing 2-acetylamino-2-deoxy-D-glucose after 200L heat inactivations, is using aperture
The ceramic membrane filter of 50nm, pure water dialysis membrane concentrated phase obtains the filter liquor 235L that content is 80g/L；
2nd, 235L filter liquors are added in electrodialysis plant, it is the desalinization liquor of 58g/L that content is obtained after electrodialysis desalination
320L；
The 3rd, 320L desalinization liquors are pumped into the 001 × 7H for being filled with Shanghai Huazhen Science and Technology Co., Ltd.'s production+Type highly acid sun
The deacetylated adsorption separation device of ion exchange resin, the reaction time is 180 minutes to material in a device, and reaction temperature is 93
℃.The resin of pure water adsorption saturation, 8% resolving hydrochloric acid adsorbs the D- Glucosamines (H in resin+With N- acetyl-D-
The mol ratio of Glucosamine is 1:0.9-10), the extraction phase that concentration containing D-Glucosamine Hydrochloride is 210g/L is obtained
87L, and the raffinate phase containing acetic acid；
4th, 0.2% activated carbon is added in extracting phase to 87L, 55 DEG C of insulations are filtered after 60 minutes, and pure water filter cake is obtained
Concentration is the destainer 91L of 200g/L；
5th, 91L destainers it is concentrated, crystallization, centrifugation, drying and processing, obtain the D- glucosamine hydrochloric acids of purity 99.6%
Salt 15500g, and concentration is the mother liquor 8L of 325g/L.
The yield of gained D-Glucosamine Hydrochloride is 96.28% in the present embodiment.
The method that the deacetylation Coupling Adsorption of embodiment 3 separates D-Glucosamine Hydrochloride
Methods described is comprised the following steps that：
1st, it is the zymotic fluid of 90g/L by content containing 2-acetylamino-2-deoxy-D-glucose after 200L heat inactivations, is using aperture
The ceramic membrane filter of 50nm, pure water dialysis membrane concentrated phase.Organic rolled film mistake of molecular cut off 3000D is used after merging filtrate
Filter, concentrated phase is dialysed with pure water, obtains the filter liquor 281L that content is 62g/L；
2nd, by 281L filter liquors by loaded particles activated carbon decolorizing column, filling Zibo Dong great chemical inc
It is the decolouring desalinization liquor of 51g/L to obtain content after the cation exchange column treatment of 001 × 7 storng-acid cation exchange resin of production
335L；
3rd, 335L decolourings desalinization liquor pumps into the D001H for being filled with the production of Zibo Dong great chemical inc+Type strong acid
Property cationic ion-exchange resin deacetylated adsorption separation device, the reaction time is 300 minutes to material in a device, and reaction temperature is
87℃.The resin of pure water adsorption saturation, D- Glucosamine (H of the 10% sulfuric acid Dissociative adsorption in resin+With N- second
The mol ratio of acyl-D- Glucosamines is 1:0.9-10), the extraction that the concentration of aminoglucose sulfate containing D- is 255g/L is obtained
Phase 63.5L, and the raffinate phase containing acetic acid；
4th, 0.2% activated carbon is added in extracting phase to 63.5L, 55 DEG C of insulations are filtered after 60 minutes, and pure water filter cake is obtained
It is the destainer 67L of 240g/L to concentration；
5th, 91L destainers it is concentrated, crystallization, centrifugation, drying and processing, obtain the D- Glucosamine sulfuric acid of purity 99.1%
Salt 6500g, and concentration is the mother liquor 22.8L of 420g/L.
The yield of gained D-Glucosamine Hydrochloride is 89.31% in the present embodiment.
The method that the deacetylation Coupling Adsorption of embodiment 4 separates D-Glucosamine Hydrochloride
Methods described is comprised the following steps that：
1st, it is the zymotic fluid of 102g/L by content containing 2-acetylamino-2-deoxy-D-glucose after 200L heat inactivations, uses aperture
It is the ceramic membrane filter of 5nm, pure water dialysis membrane concentrated phase obtains the filter liquor 243L that content is 83g/L；
2nd, by 243L filter liquors by loaded particles activated carbon decolorizing column, the production of filling Shanghai Huazhen Science and Technology Co., Ltd.
D001 storng-acid cation exchange resins cation exchange column and filling Shanghai Huazhen Science and Technology Co., Ltd. production D201
It is the decolouring desalinization liquor 290L of 68g/L to obtain content after the anion-exchange column treatment of strong-base anion-exchange resin；
3rd, 290 decolouring desalinization liquors it is concentrated, crystallization, centrifugation after purity be 98.8% 2-acetylamino-2-deoxy-D-glucose
Crystal 7140g and concentration are crystalline mother solution 22.5Ls of the 550g/L containing 2-acetylamino-2-deoxy-D-glucose；
4th, crystalline mother solutions of the 22.5L containing 2-acetylamino-2-deoxy-D-glucose is pumped into and is filled with the Shanghai China scientific and technological limited public affairs of shake
Take charge of 001 × 7H of production+The deacetylated adsorption separation device of type storng-acid cation exchange resin, when material reacts in a device
Between be 120 minutes, reaction temperature be 91 DEG C.The resin of pure water adsorption saturation, 12% resolving hydrochloric acid is adsorbed in resin
D- Glucosamines (H+It is 1 with the mol ratio of 2-acetylamino-2-deoxy-D-glucose:0.9-10), glucosamine salt containing D- is obtained
Hydrochlorate concentration is the extraction phase 36L of 335g/L, and the raffinate phase containing acetic acid；
5th, 0.2% activated carbon is added in extracting phase to 36L, 55 DEG C of insulations are filtered after 60 minutes, and pure water filter cake is obtained
Concentration is the destainer 37.5L of 320g/L；
6th, 37.5L destainers it is concentrated, crystallization, centrifugation, drying and processing, obtain the D- glucosamine salts of purity 99.4%
Hydrochlorate 10200g, and concentration is the mother liquor 5.2L of 343g/L.
The yield of gained D-Glucosamine Hydrochloride is 93.74% in the present embodiment.
The method that the deacetylation Coupling Adsorption of embodiment 5 separates D-Glucosamine Hydrochloride
Methods described is comprised the following steps that：
1st, the 2-acetylamino-2-deoxy-D-glucose crystal 7140g for obtaining the step 3 of embodiment 4 is by the concentration of 400g/L plus pure
Water dissolves, obtain lysate 17.8L；
The 2nd, 17.8L lysates are pumped into the 001 × 8H for being filled with the production of Jiangsu Su Qing resins Co., Ltd+Type highly acid sun
The deacetylated adsorption separation device of ion exchange resin, the reaction time is 150 minutes to material in a device, and reaction temperature is 90
℃.The resin of pure water adsorption saturation, D- Glucosamine (H of the 10% sulfuric acid Dissociative adsorption in resin+With N- acetyl-
The mol ratio of D- Glucosamines is 1:0.9-10), the extraction phase that the concentration of aminoglucose sulfate containing D- is 382g/L is obtained
18.3L, and the raffinate phase containing acetic acid；
3rd, 0.2% activated carbon is added in extracting phase to 18.3L, 55 DEG C of insulations are filtered after 60 minutes, and pure water filter cake is obtained
It is the destainer 19L of 366g/L to concentration；
4th, 19L destainers it is concentrated, crystallization, centrifugation, drying and processing, obtain the D- Glucosamine sulfuric acid of purity 99.2%
Salt 4520g, and concentration is the mother liquor 5.8L of 419g/L.
The yield of gained D-Glucosamine Hydrochloride is 97.34% in the present embodiment.
Although above the present invention is described in detail with a general description of the specific embodiments,
On the basis of the present invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Cause
This, these modifications or improvements, belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.
Claims (10)
1. a kind of method that deacetylation Coupling Adsorption separates D-Glucosamine Hydrochloride, it is characterised in that including following step
Suddenly：
S1, will contain 2-acetylamino-2-deoxy-D-glucose solution after pre-treatment removal of impurities liquid；
S2, removal of impurities liquid obtain being adsorbed with the saturated resin of D- Glucosamines and containing acetic acid through cationic exchange resin adsorption
Raffinate phase, wash resin column with water, then use inorganic acid desorption, obtain the extraction phase containing D-Glucosamine Hydrochloride；
S3, extract and mutually post-treated obtain D-Glucosamine Hydrochloride finished product.
2. method according to claim 1, it is characterised in that the solution of 2-acetylamino-2-deoxy-D-glucose described in S1 is
The solution containing 2-acetylamino-2-deoxy-D-glucose obtained by microbe fermentation method or enzyme transforming process.
3. method according to claim 1 and 2, it is characterised in that cationic ion-exchange resin described in S2 is selected from highly acid
Cationic ion-exchange resin or weak-acid cation-exchange resin, preferably storng-acid cation exchange resin.
4. the method according to claim any one of 1-3, it is characterised in that absorption is in 50 DEG C of -150 DEG C of temperature described in S2
Carried out under degree, preferably 75 DEG C -98 DEG C.
5. the method according to claim any one of 1-4, it is characterised in that the total reaction time of adsorption and desorption in S2
It is -600 minutes 20 minutes, preferably -300 minutes 120 minutes.
6. the method according to claim any one of 1-5, it is characterised in that inorganic acid described in S2 is selected from hydrochloric acid, sulfuric acid
Or phosphoric acid, the concentration of the inorganic acid is 2%-60%.
7. method according to claim 6, it is characterised in that the H of inorganic acid used in S2+With N- acetyl-D- in removal of impurities liquid
The mol ratio of Glucosamine is 1:0.9-10.
8. the method according to claim any one of 1-7, it is characterised in that the total reaction time of adsorption and desorption in S2
It is -600 minutes 20 minutes, preferably -300 minutes 120 minutes.
9. the method according to claim any one of 1-8, it is characterised in that pretreatment mode described in S1 be selected from heating,
At least one in sedimentation, filtering, decolouring, desalination, concentration, crystallization, centrifugation.
10. the method according to claim any one of 1-9, it is characterised in that post processing mode described in S3 be selected from decolourize,
Filtering, concentration, crystallization, centrifugation, dry at least one.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611227841.1A CN106831894B (en) | 2016-12-27 | 2016-12-27 | A kind of method of deacetylation Coupling Adsorption separation D-Glucosamine Hydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611227841.1A CN106831894B (en) | 2016-12-27 | 2016-12-27 | A kind of method of deacetylation Coupling Adsorption separation D-Glucosamine Hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106831894A true CN106831894A (en) | 2017-06-13 |
| CN106831894B CN106831894B (en) | 2019-08-30 |
Family
ID=59135590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201611227841.1A Active CN106831894B (en) | 2016-12-27 | 2016-12-27 | A kind of method of deacetylation Coupling Adsorption separation D-Glucosamine Hydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106831894B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111518857A (en) * | 2020-06-11 | 2020-08-11 | 江苏海飞生物科技有限公司 | Enzyme method for producing glucosamine salt and purification method thereof |
| CN111647027A (en) * | 2020-06-11 | 2020-09-11 | 江苏海飞生物科技有限公司 | Method for separating and purifying N-acetylglucosamine |
| CN113045610A (en) * | 2020-12-20 | 2021-06-29 | 宁夏金维制药股份有限公司 | Method for extracting glucosamine from N-acetylglucosamine fermentation liquor |
| CN113717235A (en) * | 2021-10-08 | 2021-11-30 | 山东奥健营养有限责任公司 | Method for preparing glucosamine hydrochloride by using pretreated glucosamine fermentation liquor |
| CN113861247A (en) * | 2021-10-31 | 2021-12-31 | 扬州明增生物科技有限公司 | Method for extracting glucosamine hydrochloride from fermentation liquor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005056525A2 (en) * | 2003-12-09 | 2005-06-23 | Bio-Technical Resources | Deacetylation of n-acetylglucosamine |
-
2016
- 2016-12-27 CN CN201611227841.1A patent/CN106831894B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005056525A2 (en) * | 2003-12-09 | 2005-06-23 | Bio-Technical Resources | Deacetylation of n-acetylglucosamine |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111518857A (en) * | 2020-06-11 | 2020-08-11 | 江苏海飞生物科技有限公司 | Enzyme method for producing glucosamine salt and purification method thereof |
| CN111647027A (en) * | 2020-06-11 | 2020-09-11 | 江苏海飞生物科技有限公司 | Method for separating and purifying N-acetylglucosamine |
| WO2021248696A1 (en) * | 2020-06-11 | 2021-12-16 | 江苏海飞生物科技有限公司 | Separation and purification method for n-acetylglucosamine |
| US11555049B2 (en) | 2020-06-11 | 2023-01-17 | Jiangsu Harvers Biotech Co., Ltd. | Method for separation and purification of n-acetylglucosamine |
| CN113045610A (en) * | 2020-12-20 | 2021-06-29 | 宁夏金维制药股份有限公司 | Method for extracting glucosamine from N-acetylglucosamine fermentation liquor |
| CN113717235A (en) * | 2021-10-08 | 2021-11-30 | 山东奥健营养有限责任公司 | Method for preparing glucosamine hydrochloride by using pretreated glucosamine fermentation liquor |
| CN113861247A (en) * | 2021-10-31 | 2021-12-31 | 扬州明增生物科技有限公司 | Method for extracting glucosamine hydrochloride from fermentation liquor |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106831894B (en) | 2019-08-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106831894B (en) | A kind of method of deacetylation Coupling Adsorption separation D-Glucosamine Hydrochloride | |
| CN109593034B (en) | Method for preparing shikimic acid from ginkgo leaf extraction waste liquid | |
| CN101863822B (en) | Production method for extracting tryptophan from fermentation liquor by one-step refining | |
| CN109180745B (en) | Method for preparing N-acetylneuraminic acid by separating and purifying polysialic acid-containing material | |
| CN108822163B (en) | Comprehensive cyclic production method of D-glucosamine hydrochloride | |
| WO2012051774A1 (en) | Process for salting out and extracting organic acid from fermentation broth | |
| CN101486637A (en) | Method for extracting amber acid from fermentation liquor | |
| CN109265498B (en) | Method for preparing N-acetylneuraminic acid by integrated separation and purification of polysialic acid | |
| CN106397630A (en) | Method for extracting sodium hyaluronate based on membrane separation technology | |
| CN101580475A (en) | Novel process for producing valine | |
| US20230167474A1 (en) | Methods for enzymatic production of glucosamine salts and the purification methods thereof | |
| CN115160108B (en) | Process for preparing inositol and phosphoric acid | |
| CN106995398A (en) | L proline novel technology for extracting | |
| CN113135954A (en) | Process method for preparing calcium phytate and calcium lactate by using corn soaking water | |
| CN102603478B (en) | Method for separating and purifying erythritol from mother liquid obtained after repeated crystallization of erythritol | |
| CN106631852A (en) | Method for extracting L-ornithine hydrochloride from L-ornithine fermentation broth | |
| CN101665428A (en) | Method for extracting succinic acid from succinic acid fermentation liquor | |
| CN101693732B (en) | Method for extracting and purifying natamycin | |
| CN105622342B (en) | A kind of method for detaching 2,3- butanediols | |
| CN102964213B (en) | Method for recovering erythritol from erythritol crystallization mother liquor | |
| CN112409426B (en) | Preparation method of sisomicin sulfate | |
| CN104357493A (en) | Method for preparing xylitol from viscose fiber squeezed alkali liquor | |
| CN106977442A (en) | A kind of extraction process of hydroxyproline | |
| CN1089615A (en) | 1,6-hexose diphosphate method for purification | |
| CN107032983A (en) | A kind of method that utilization macroporous absorbent resin extracts separation butanedioic acid from zymotic fluid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |