CN106831895A - A kind of method of purifying N acetylglucosamines - Google Patents
A kind of method of purifying N acetylglucosamines Download PDFInfo
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- CN106831895A CN106831895A CN201710038401.XA CN201710038401A CN106831895A CN 106831895 A CN106831895 A CN 106831895A CN 201710038401 A CN201710038401 A CN 201710038401A CN 106831895 A CN106831895 A CN 106831895A
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- acetamido
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- deoxy
- glucose
- desalination
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- 238000000034 method Methods 0.000 title claims abstract description 37
- ZUQUTHURQVDNKF-KEWYIRBNSA-N 1-[(3R,4R,5S,6R)-3-amino-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]ethanone Chemical class CC(=O)C1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1N ZUQUTHURQVDNKF-KEWYIRBNSA-N 0.000 title abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 90
- 238000010612 desalination reaction Methods 0.000 claims abstract description 34
- 239000000706 filtrate Substances 0.000 claims abstract description 26
- 239000012535 impurity Substances 0.000 claims abstract description 25
- 239000011343 solid material Substances 0.000 claims abstract description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000001914 filtration Methods 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 16
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 239000013078 crystal Substances 0.000 claims abstract description 13
- 150000001413 amino acids Chemical class 0.000 claims abstract description 11
- 238000005119 centrifugation Methods 0.000 claims abstract description 8
- 238000005516 engineering process Methods 0.000 claims abstract description 7
- 239000005416 organic matter Substances 0.000 claims abstract description 5
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 44
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims description 44
- 238000007865 diluting Methods 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 239000003014 ion exchange membrane Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 235000019441 ethanol Nutrition 0.000 description 35
- 239000000047 product Substances 0.000 description 19
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 12
- 239000012530 fluid Substances 0.000 description 10
- 239000000919 ceramic Substances 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 235000001727 glucose Nutrition 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 4
- 230000004151 fermentation Effects 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000909 electrodialysis Methods 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- -1 salt ion Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MSWZFWKMSRAUBD-UHFFFAOYSA-N 2-Amino-2-Deoxy-Hexose Chemical compound NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JCZPMGDSEAFWDY-SQOUGZDYSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanamide Chemical compound NC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO JCZPMGDSEAFWDY-SQOUGZDYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000008452 baby food Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 210000003321 cartilage cell Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 231100000481 chemical toxicant Toxicity 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000001976 enzyme digestion Methods 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000036449 good health Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/42—Electrodialysis; Electro-osmosis ; Electro-ultrafiltration; Membrane capacitive deionization
- B01D61/422—Electrodialysis
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Water Supply & Treatment (AREA)
- Urology & Nephrology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention provides a kind of method of purifying N acetylglucosamines, including：Add activated carbon carries out desolventing technology to feed liquid；Wherein, feed liquid includes N acetylglucosamines；Filtration treatment is carried out to the feed liquid after decolouring, the filtrate for obtaining removes salt ion and the organic matter with electric charge, including albumen and amino acid by electroosmose process desalination removal of impurities；45 60 DEG C of solution after desalination is concentrated in vacuo to solution saturation；To the ethanol that 10% 50% volumes are added in the solution after concentration, 20 25 DEG C are cooled to, crystallize 8 12h, crystal material is obtained by filtering or centrifugation；The crystal material that will be obtained is added in ethanol solution to be carried out after alcohol washes, and filtering or centrifugation obtain white solid material；The white solid material that will be obtained dries 3 5h under the conditions of 50 80 DEG C, obtains pure white purifying N acetylglucosamines.The present invention uses electroosmose process desalination removal of impurities, and high income, purity is high, and energy consumption is low, and to feed liquid strong adaptability, simple to operate easy to automate, water saving efficiency is high.
Description
Technical field
The invention belongs to technical field of biochemistry, and in particular to a kind of method of purifying 2-Acetamido-2-deoxy-D-glucose.
Background technology
2-Acetamido-2-deoxy-D-glucose is a kind of reductive monosaccharide for having a sugariness higher, is many important polysaccharide in organism
Basic composition unit.Research display, 2-Acetamido-2-deoxy-D-glucose has the effect for suppressing growth of tumour cell；Can clinically make
It is rheumatic and the medicine of rheumatoid arthritis, 2-Acetamido-2-deoxy-D-glucose can stimulate cartilage cell's synthetic proteins many
Sugar, promotes the reparation of cartilage；Can also treat the gastrointestinal diseases such as gastrointestinal tract inflammation, dysfunction and gastric ulcer simultaneously；N- second
There is acylamino- glucose immunocompetence and good health care function to act on, can be used as the anti-of infant food additive and food
Oxidant, can also use as the sweetener of diabetic, be widely used in fields such as food, chemical industry, medical science.
The technique of production 2-Acetamido-2-deoxy-D-glucose mainly has three kinds at present：Chemical synthesis, enzymatic isolation method and microorganism hair
Ferment method.
Chemical synthesis is, with D-Glucosamine Hydrochloride as raw material, N- acetylaminos Portugal to be obtained by acetylization reaction
Grape sugar product.There can be certain danger using to toxic organic solvents in chemical synthesis technique.
Enzymatic isolation method is that chitin is obtained 2-Acetamido-2-deoxy-D-glucose by enzyme digestion reaction.Enzymatic isolation method technique is simpler, reaction
Gently, single enzyme reaction time oversize percent hydrolysis is too low, and typically using complex enzyme, but enzyme is expensive, and the reaction time
More long, hydrolysis is incomplete, and industrial production cost is too high.
Microbe fermentation method is to produce 2-Acetamido-2-deoxy-D-glucose by microbial fermentation.Apply for a patent
In 201610064158.4,2-Acetamido-2-deoxy-D-glucose zymotic fluid is obtained by fermentation first, then zymotic fluid is sterilized,
The solid impurities such as thalline are removed by ceramic membrane or plate-frame filtering after sterilizing, flocculate with chitosan removing protein is added in filtrate, added
Filtered after activated carbon decolorizing, then by ion exchange mixed bed, add alcohol low temperature condensing crystallizing in feed liquid, then with more than 95%
Ethanol is rinsed, and obtains 2-Acetamido-2-deoxy-D-glucose product.
The content of the invention
The purpose of the present invention is to solve the shortcomings of the prior art, there is provided a kind of process is simple, low production cost, yield are high
2-Acetamido-2-deoxy-D-glucose preparation method.
The embodiment provides a kind of method for purifying 2-Acetamido-2-deoxy-D-glucose, comprise the following steps：
(1) add activated carbon carries out desolventing technology to feed liquid；Wherein, feed liquid includes 2-Acetamido-2-deoxy-D-glucose；
(2) filtration treatment is carried out to the feed liquid after decolouring, the filtrate for obtaining by electroosmose process desalination removal of impurities, except desalt from
Son and the organic matter with electric charge, including albumen and amino acid；
(3) 45-60 DEG C of solution after desalination is concentrated in vacuo to solution saturation；
(4) to the ethanol that 10%-50% volumes are added in the solution after concentration, 20-25 DEG C is cooled to, crystallizes 8-12h, warp
Filtering or centrifugation obtain crystal material；
(5) the crystal material that will be obtained is added in ethanol solution to be carried out after alcohol washes, and filtering or centrifugation obtain white
Solid material；
(6) the white solid material that will be obtained dries 3-5h under the conditions of 50-80 DEG C, obtains pure white crystalline powder, i.e.,
It is purifying 2-Acetamido-2-deoxy-D-glucose.
Further, in step (2), electroosmose process desalination includes：Using dense form homogeneous ion-exchange membrane, diluting compartment with it is dense
Contracting building volume ratio is controlled to 3-5:1, in below 300 μ s/cm, operating voltage control exists for the final electrical conductivity control of solution after desalination
20-40V, flow control is in 18-25L/h.
Further, in step (1), the condition of desolventing technology is：30-60min is stirred under the conditions of 40-60 DEG C.
Further, in step (1), 2-Acetamido-2-deoxy-D-glucose is with the mass ratio of activated carbon：1:0.03-0.1.
Compared with prior art the beneficial effects of the invention are as follows：For Production by Microorganism Fermentation N- acetamido glucoses
Sugar, using electroosmose process desalination removal of impurities, can obtain yield more than 75%, and the 2-Acetamido-2-deoxy-D-glucose of purity more than 98% is produced
Product, product color is good, and quality is high, meets related quality criterion.Electroosmose process desalination removal of impurities energy ezpenditure is low, to feed liquid adaptability
By force, compact conformation, simple to operate easy to automate, the utilization rate of water is high, 70% or so water can be saved, substantially without dirt
Dye, has truly accomplished cleanly production.
Specific embodiment
Below by each implementation method, the present invention is described in detail, but it should explanation, these implementation methods are simultaneously
Non- limitation of the present invention, those of ordinary skill in the art are according in these implementation method institutes works energy, method or structure
Equivalent transformation or replacement, belong within protection scope of the present invention.
A kind of method for purifying 2-Acetamido-2-deoxy-D-glucose is present embodiments provided, is comprised the following steps：
(1) sterilize, filter：After zymotic fluid is through 95 DEG C of sterilizing 2h, the impurity such as thalline are removed by ceramic membrane filter, and wash
2-Acetamido-2-deoxy-D-glucose content is less than 0.2% into thalline residue, obtains clear filtrate.95 DEG C sterilizing be within two hours in order that
Microorganism all inactivation not regrowths, the quality of the 2-Acetamido-2-deoxy-D-glucose in zymotic fluid is not influenceed in zymotic fluid, will not yet
New impurity is produced again；It is to remove the solubilities such as the solid impurities such as thalline and some high molecular weight proteins using ceramic membrane filter
Impurity, is conducive to the operation of next step.
(2) decolourize：Add activated carbon carries out desolventing technology to feed liquid, 40-60 DEG C is heated to, in speed of agitator 200-
30-60min is persistently stirred under the conditions of 400rpm/min, completes to decolourize, filtered while hot.Wherein 2-Acetamido-2-deoxy-D-glucose and activity
The mass ratio of charcoal is 1:0.03-0.1.The purpose for adding activated carbon is to remove the color and partial impurities in zymotic fluid.This is under
The time of one step desalination removal of impurities has an impact, if decolorizing effect is bad, can extend the time of desalination removal of impurities, and decolorizing effect is bad also
Increase the ethanol consumption that alcohol washes journey, influence the outward appearance of product.
(3) filtering, desalination：Feed liquid after decolouring is filtered through film filter or sheet frame, and the filtrate for obtaining passes through electric osmose
Analysis method desalination removal of impurities, removes salt ion and the organic matter with electric charge --- the soluble impurity such as albumen, amino acid, and the time is
1h or so.The film that electroosmose process is used is dense form homogeneous ion-exchange membrane, and this film is effectively removing salt ion and band
There is the organic matter of electric charge --- while the soluble impurity such as albumen, amino acid, 2-Acetamido-2-deoxy-D-glucose can be reduced and pass through film,
So as to reduce the loss of 2-Acetamido-2-deoxy-D-glucose in desalination dedoping step；In desalination dedoping step, diluting compartment with concentration chamber body
Product is than being 3-5:1, preferably, desalination is except miscellaneous time is shorter, treating capacity is larger and N- acetyl for the effect of desalination removal of impurities under the conditions of this
The loss late of Glucosamine is minimum；Desalination to the electrical conductivity of solution is reached below 300 μ s/cm, the removal of albumen and amino acid
Rate reaches more than 96%, and operating voltage is controlled in 20-40V, and flow control is in 18-25L/h.
(4) concentrate：Solution after desalination is directly concentrated in vacuo, under the conditions of vacuum is more than 0.9MPa, temperature
Control is concentrated in vacuo to solution and reaches saturation at 45-60 DEG C.Solution after desalination is added without ethanol and is directly concentrated in vacuo,
Although adding ethanol can reduce the boiling point of solution so that the water in solution is easier to be evaporated, ethanol concentration meeting is added
So that crystal is easily separated out and speed of separating out is very fast, the product of One-step crystallization process 2-Acetamido-2-deoxy-D-glucose product under the influence of this meeting
Matter, and addition ethanol can also cause that whole cost is improved.
(5) crystallize：To the ethanol that 10%-50% volumes are added in the solution after concentration, 20-25 DEG C is cooled to, crystallizes 8-
12h, crystal material is obtained by filtering or centrifugation.It is cooled to 20-25 DEG C of crystallization to be compared with low temperature crystallization, N- acetamido glucoses
The yield and quality of sugar are basically identical, using low temperature crystallization high energy consumption, improve production cost.
(6) alcohol is washed：The solid material that will be obtained is added in ethanol solution and carries out alcohol and wash, and the volume of ethanol is solid
1-1.5 times of material, mixing speed 100-200rpm/min, filtering or centrifugation obtain white solid material, repeat alcohol and wash 3 times.
Using absolute ethyl alcohol carry out alcohol wash because 2-Acetamido-2-deoxy-D-glucose it is water-soluble especially good, if not using absolute ethyl alcohol, meeting
Reduce the yield of 2-Acetamido-2-deoxy-D-glucose.
(7) dry：The white solid material that will be obtained dries 3-5h under the conditions of 50-80 DEG C, obtains pure white crystal powder
End, the 2-Acetamido-2-deoxy-D-glucose product for as preparing.
The product color of the 2-Acetamido-2-deoxy-D-glucose prepared by the method for the present embodiment is good, better quality, receives
Rate is higher.Whole technical process is simple, energy consumption is low, substantially pollution-free, has not only saved resource, reduces production cost, and
Environmental protection.
Below by specific embodiment, the invention will be further described.
Embodiment 1
(1) 3L zymotic fluids are taken 2h is heated under the conditions of 90 DEG C, the impurity such as thalline, and water are then removed by ceramic membrane filter
2-Acetamido-2-deoxy-D-glucose content obtains 3.5L clear filtrates, N- acetylaminos in filtrate less than 0.2% in being washed till thalline residue
Glucose content is 65g/L.
(2) to 10g activated carbons are added in above-mentioned filtrate, 40 DEG C are heated to, are held under the conditions of speed of agitator 200rpm/min
Continuous stirring 30min, completes to decolourize.
(3) solution after above-mentioned decolouring obtains clear filtrate by suction filtration, and the filtrate for obtaining is removed by electroosmose process desalination
Miscellaneous, diluting compartment is 3 with enriched chamber's volume ratio:1, operating voltage is controlled in 30V, and flow control is in 25L/h, desalination to solution conductivity
Rate reaches 200 μ s/cm, and the clearance of albumen and amino acid reaches 97.3%.
(4) by the solution after above-mentioned desalination, under the conditions of vacuum 0.92MPa, temperature 60 C, it is concentrated in vacuo to solution and reaches
To saturation.
(5) to the ethanol that 20% volume is added in the solution after above-mentioned concentration, 20 DEG C are cooled to, crystallize 8h, by filtering
Obtain crystal material.
(6) be added to material obtained above carries out alcohol and washes in ethanol solution, and the volume of ethanol is solid material
1.5 times, mixing speed 100rpm/min is filtrated to get white solid material, repeats alcohol and washes 3 times.
(7) white solid material obtained above is dried into 3h under the conditions of 70 DEG C, obtains pure white crystalline powder, as
The 2-Acetamido-2-deoxy-D-glucose product for preparing.
The yield of product is 81.55%, and purity is 99.6%.
Embodiment 2
(1) 5L zymotic fluids are taken 2h is heated under the conditions of 95 DEG C, the impurity such as thalline, and water are then removed by ceramic membrane filter
2-Acetamido-2-deoxy-D-glucose content obtains 6.2L clear filtrates, N- acetylaminos in filtrate less than 0.2% in being washed till thalline residue
Glucose content is 72g/L.
(2) to 13g activated carbons are added in above-mentioned filtrate, 60 DEG C are heated to, are held under the conditions of speed of agitator 400rpm/min
Continuous stirring 30min, completes to decolourize.
(3) solution after above-mentioned decolouring obtains clear filtrate by plate-frame filtering, and the filtrate for obtaining is de- by electroosmose process
Salt removal of impurities, diluting compartment is 4 with enriched chamber's volume ratio:1, operating voltage is controlled in 20V, and flow control is in 18L/h, desalination to solution
Electrical conductivity reaches 280 μ s/cm, and albumen and amino acid clearance reach 96.8%.
(4) by the solution after above-mentioned desalination, under the conditions of vacuum 0.95MPa, temperature 45 C, it is concentrated in vacuo to solution and reaches
To saturation.
(5) to the absolute ethyl alcohol that 10% volume is added in the solution after above-mentioned concentration, 20 DEG C are cooled to, crystallize 10h, passed through
It is filtrated to get crystal material.
(6) be added to material obtained above carries out alcohol and washes in ethanol solution, and the volume of ethanol is solid material
1.5 times, mixing speed 200rpm/min is filtrated to get white solid material, repeats alcohol and washes 3 times.
(7) white solid material obtained above is dried into 4h under the conditions of 65 DEG C, obtains pure white crystalline powder, as
The 2-Acetamido-2-deoxy-D-glucose product for preparing.
The yield of product is 78.8%, and purity is 100.5%.
Embodiment 3
(1) 10L zymotic fluids are taken 2h is heated under the conditions of 95 DEG C, the impurity such as thalline are then removed by ceramic membrane filter, and
2-Acetamido-2-deoxy-D-glucose content obtains 12L clear filtrates, N- acetyl ammonia in filtrate less than 0.2% in being washed to thalline residue
Base glucose content is 78g/L.
(2) to 70g activated carbons are added in above-mentioned filtrate, 50 DEG C are heated to, are held under the conditions of speed of agitator 300rpm/min
Continuous stirring 40min, completes to decolourize.
(3) solution after above-mentioned decolouring obtains clear filtrate by plate-frame filtering, and the filtrate for obtaining is de- by electroosmose process
Salt removal of impurities, diluting compartment is 5 with enriched chamber's volume ratio:1, operating voltage is controlled in 40V, and flow control is in 25L/h, desalination to solution
Electrical conductivity reaches 150 μ s/cm, and the clearance of albumen and amino acid reaches 98.1%.
(4) by the solution after above-mentioned desalination, under the conditions of vacuum 0.92MPa, 55 DEG C of temperature, it is concentrated in vacuo to solution and reaches
To saturation.
(5) to the absolute ethyl alcohol that 50% volume is added in the solution after above-mentioned concentration, 25 DEG C are cooled to, crystallize 10h, passed through
It is filtrated to get crystal material.
(6) be added to material obtained above carries out alcohol and washes in ethanol solution, and the volume of ethanol is solid material
1 times, mixing speed 150rpm/min is filtrated to get white solid material, repeats alcohol and washes 3 times.
(7) white solid material obtained above is dried into 2h under the conditions of 80 DEG C, obtains pure white crystalline powder, as
The 2-Acetamido-2-deoxy-D-glucose product for preparing.
The yield of product is 82.37%, and purity is 99.8%.
Embodiment 4
(1) 20L zymotic fluids are taken 2h is heated under the conditions of 90 DEG C, the impurity such as thalline are then removed by ceramic membrane filter, and
2-Acetamido-2-deoxy-D-glucose content obtains 23.8L clear filtrates, N- acetyl in filtrate less than 0.2% in being washed to thalline residue
Aminoglucose sugared content is 88g/L.
(2) to 209g activated carbons are added in above-mentioned filtrate, 60 DEG C are heated to, are held under the conditions of speed of agitator 400rpm/min
Continuous stirring 60min, completes to decolourize.
(3) solution after above-mentioned decolouring obtains clear filtrate by plate-frame filtering, and the filtrate for obtaining passes through electrodialysis plant
Desalination, diluting compartment is 4 with enriched chamber's volume ratio:1, in 20V, flow control is in 20L/h, desalination to solution electricity for operating voltage control
Conductance reaches 85 μ s/cm, and the clearance of albumen and amino acid reaches 98.5%.
(4) by the solution after above-mentioned desalination, under the conditions of vacuum 0.95MPa, temperature 50 C, it is concentrated in vacuo to solution and reaches
To saturation.
(5) to the absolute ethyl alcohol that 30% volume is added in the solution after above-mentioned concentration, 25 DEG C are cooled to, crystallize 12h, passed through
It is filtrated to get crystal material.
(6) be added to material obtained above carries out alcohol and washes in ethanol solution, and the volume of ethanol is solid material
1.5 times, mixing speed 100rpm/min is filtrated to get white solid material, repeats alcohol and washes 3 times.
(7) white solid material obtained above is dried into 5h under the conditions of 50 DEG C, obtains pure white crystalline powder, as
The 2-Acetamido-2-deoxy-D-glucose product for preparing.
The yield of product is 85.39%, and purity is 101.2%.
The method of the purifying 2-Acetamido-2-deoxy-D-glucose that the present embodiment is provided, employs ceramic membrane filter removal of impurities, activated carbon
Decolourize, electrodialysis removing salt ion and electrically charged small molecular protein and amino acid, condensing crystallizing, washing and drying, it is to avoid
The use of toxic chemical, whole operation is simply efficient, and yield is up to more than 75%, and electrodialysis plant energy consumption is low, substantially without
Pollution, environmental protection has been truly realized cleanly production, the 2-Acetamido-2-deoxy-D-glucose good product quality of gained.
Those listed above is a series of to be described in detail only for feasibility implementation method of the invention specifically
Bright, they simultaneously are not used to limit the scope of the invention, all equivalent implementations made without departing from skill spirit of the present invention
Or change should be included within the scope of the present invention.
It is obvious to a person skilled in the art that the invention is not restricted to the details of above-mentioned one exemplary embodiment, Er Qie
In the case of without departing substantially from spirit or essential attributes of the invention, the present invention can be in other specific forms realized.Therefore, no matter
From the point of view of which point, embodiment all should be regarded as exemplary, and be nonrestrictive, the scope of the present invention is by appended power
Profit requires to be limited rather than described above, it is intended that all in the implication and scope of the equivalency of claim by falling
Change is included in the present invention.
Claims (4)
1. it is a kind of purify 2-Acetamido-2-deoxy-D-glucose method, it is characterised in that comprise the following steps：
(1) add activated carbon carries out desolventing technology to feed liquid；Wherein, the feed liquid includes 2-Acetamido-2-deoxy-D-glucose；
(2) filtration treatment is carried out to the feed liquid after decolouring, the filtrate for obtaining by electroosmose process desalination removal of impurities, remove salt ion with
And the organic matter with electric charge, including albumen and amino acid；
(3) 45-60 DEG C of solution after desalination is concentrated in vacuo to solution saturation；
(4) to the ethanol that 10%-50% volumes are added in the solution after concentration, 20-25 DEG C is cooled to, crystallizes 8-12h, passed through
Filter or centrifugation obtain crystal material；
(5) the crystal material that will be obtained is added in ethanol solution to be carried out after alcohol washes, and filtering or centrifugation obtain white solid
Material；
(6) the white solid material that will be obtained dries 3-5h under the conditions of 50-80 DEG C, obtains pure white crystalline powder, as pure
Change 2-Acetamido-2-deoxy-D-glucose.
2. it is according to claim 1 it is a kind of purify 2-Acetamido-2-deoxy-D-glucose method, it is characterised in that in step (2),
The electroosmose process desalination includes：Using dense form homogeneous ion-exchange membrane, diluting compartment is controlled to 3-5 with enriched chamber's volume ratio:
1, in below 300 μ s/cm, operating voltage is controlled in 20-40V, and flow control is in 18- for the final electrical conductivity control of solution after desalination
25L/h。
3. it is according to claim 1 it is a kind of purify 2-Acetamido-2-deoxy-D-glucose method, it is characterised in that in step (1),
The condition of the desolventing technology is：30-60min is stirred under the conditions of 40-60 DEG C.
4. it is according to claim 1 it is a kind of purify 2-Acetamido-2-deoxy-D-glucose method, it is characterised in that in step (1),
The 2-Acetamido-2-deoxy-D-glucose is with the mass ratio of activated carbon：1:0.03-0.1.
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108383883A (en) * | 2018-04-09 | 2018-08-10 | 大自然生物集团有限公司 | The preparation method of high purity N-acetyl-D Glucosamines |
| CN110590869A (en) * | 2019-10-09 | 2019-12-20 | 山东润德生物科技有限公司 | Preparation method of N-acetylglucosamine |
| CN110845552A (en) * | 2019-11-22 | 2020-02-28 | 山东润德生物科技有限公司 | Preparation method of acylated derivative of glucosamine |
| CN111004295A (en) * | 2019-12-09 | 2020-04-14 | 山东润德生物科技有限公司 | Preparation method for efficiently synthesizing N-acetylglucosamine |
| CN111018926A (en) * | 2019-12-17 | 2020-04-17 | 大自然生物集团有限公司 | Method for extracting high-purity glucosamine hydrochloride from glucosamine fermentation liquor |
| 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 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1907993A (en) * | 2006-08-22 | 2007-02-07 | 王松叶 | Process for preparing refined N-acetyl-D-aminoglucose |
| CN101195662A (en) * | 2007-12-20 | 2008-06-11 | 山东大学 | 6-(2-glucosyl amido)-beta- cyclodextrin derivant and method for producing the same |
| CN105039193A (en) * | 2015-01-27 | 2015-11-11 | 安徽正方生物科技有限公司 | Strain and method for producing glucosamine through microorganism fermentation |
-
2017
- 2017-01-19 CN CN201710038401.XA patent/CN106831895B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1907993A (en) * | 2006-08-22 | 2007-02-07 | 王松叶 | Process for preparing refined N-acetyl-D-aminoglucose |
| CN101195662A (en) * | 2007-12-20 | 2008-06-11 | 山东大学 | 6-(2-glucosyl amido)-beta- cyclodextrin derivant and method for producing the same |
| CN105039193A (en) * | 2015-01-27 | 2015-11-11 | 安徽正方生物科技有限公司 | Strain and method for producing glucosamine through microorganism fermentation |
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|---|---|---|---|---|
| CN108383883A (en) * | 2018-04-09 | 2018-08-10 | 大自然生物集团有限公司 | The preparation method of high purity N-acetyl-D Glucosamines |
| CN110590869A (en) * | 2019-10-09 | 2019-12-20 | 山东润德生物科技有限公司 | Preparation method of N-acetylglucosamine |
| CN110845552A (en) * | 2019-11-22 | 2020-02-28 | 山东润德生物科技有限公司 | Preparation method of acylated derivative of glucosamine |
| CN111004295A (en) * | 2019-12-09 | 2020-04-14 | 山东润德生物科技有限公司 | Preparation method for efficiently synthesizing N-acetylglucosamine |
| CN111018926A (en) * | 2019-12-17 | 2020-04-17 | 大自然生物集团有限公司 | Method for extracting high-purity glucosamine hydrochloride from glucosamine fermentation liquor |
| CN111018926B (en) * | 2019-12-17 | 2023-10-10 | 大自然生物集团有限公司 | Method for extracting high-purity glucosamine hydrochloride from glucosamine fermentation broth |
| 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 |
| US11555049B2 (en) | 2020-06-11 | 2023-01-17 | Jiangsu Harvers Biotech Co., Ltd. | Method for separation and purification of n-acetylglucosamine |
| CN112375111A (en) * | 2020-12-08 | 2021-02-19 | 山东润德生物科技有限公司 | Production process and application of glucosamine |
| CN113845553A (en) * | 2021-10-09 | 2021-12-28 | 山东润德生物科技有限公司 | Preparation method of N-acetylglucosamine with low water activity and N-acetylglucosamine |
| CN113826866A (en) * | 2021-10-14 | 2021-12-24 | 山东润德生物科技有限公司 | Method for preparing seasoning by using N-acetylglucosamine mother liquor |
| CN113893255A (en) * | 2021-10-29 | 2022-01-07 | 山东润德生物科技有限公司 | Method for preparing smearing preparation by using N-acetylglucosamine mother liquor |
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