CN103450289A - Preparation method of D-glucosamine hydrochloride - Google Patents
Preparation method of D-glucosamine hydrochloride Download PDFInfo
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- CN103450289A CN103450289A CN2013103758609A CN201310375860A CN103450289A CN 103450289 A CN103450289 A CN 103450289A CN 2013103758609 A CN2013103758609 A CN 2013103758609A CN 201310375860 A CN201310375860 A CN 201310375860A CN 103450289 A CN103450289 A CN 103450289A
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Abstract
The invention discloses a preparation method of D-glucosamine hydrochloride. Citric acid waste residues obtained after production of citric acid through a fermentation method are taken as raw materials, a mixed acid consisting of hydrochloric acid and acetic acid is taken as a hydrolysis reagent, and the D-glucosamine hydrochloride is finally obtained by the following steps: hydrolysis of the mixed acid, filtration, decolorization, suction filtration, crystallization, drying and the like. According to the preparation method, as the mixed acid consisting of the hydrochloric acid and the acetic acid is adopted as the hydrolysis reagent for hydrolysis reaction during the preparation process, the using amount of the hydrochloric acid during the hydrolysis by using the hydrochloric acid alone is further effectively reduced, the corrosion degree of production equipment is further reduced, and the final yield of the D-glucosamine hydrochloride achieves 5.0-5.2%. Meanwhile, the preparation method has the characteristics of rich raw material sources, no limitation on production resources and low production cost.
Description
Technical field
Technical field of the present invention is healthcare products and medical material, and particularly a kind of citric acid waste residues that utilizes prepares the method for D-Glucosamine Hydrochloride for raw material.
Background technology
Citric acid is a kind of widely used organic acid, can be used as acidic flavoring agent and thickening material, can also use as clean-out system, is widely used in food, beverage, medicine, chemical industry, washing composition etc. relevant industries.At present, China is the first in the world citric acid export State, and current most enterprise is with in fermentative Production citric acid process, and a large amount of citric acid waste residues are not reasonably utilized, and directly efflux.
D-Glucosamine Hydrochloride, molecular formula C
6h
13nO
5hCl, white crystal, odorlessness, slightly pleasantly sweet, soluble in water, be slightly soluble in methyl alcohol, be insoluble to the organic solvents such as ethanol.Glucosamine hydrochloride is the basic composition unit of many important polysaccharide in biomass cells, it is the important as precursors of synthetic bifidus factor, there is in vivo important physiological function, be mainly used in clinical enhancing human immune system function, anticancer or fibrocellular excessive increase, have certain medical functions for cancer and malignant tumour.D-Glucosamine Hydrochloride is the health care medicine intermediate risen into recent domestic simultaneously, it is also the important source material of senior cosmetic healthcare products, the effective constituent of the medicine of the diseases such as treatment rheumatic arthritis, rheumatic heart disease, ulcer, enteritis, or the additive of up-to-date third generation heath-function food.
Industrial production glucosamine hydrochloride and series derivates raw material used thereof are mainly the chitins extracted from the crustacean shell at present, this raw material is confined to coastland, also be subject to the impact in season larger simultaneously, the present invention adopts citric acid waste residues as starting material, through techniques such as acid hydrolysis, filtration, decolouring, suction filtration, crystallization, dryings, obtains glucosamine hydrochloride.
The present invention in the past, has had some records about citric acid waste residues is open for the preparation of the patent of invention of glucosamine hydrochloride, as patents such as CN200810088877.5, CN200810238484.8 and CN201010246930.7.Although the CN201010246930.7 patent had broken through understanding mistaken ideas before the first two patent, that is: hydrolysis temperature can not surpass 90 ℃, otherwise easily causes the citric acid waste carbonization, thereby causes yield reducation; But in this patent, 30%～35% hydrochloric acid is used in acid hydrolysis fully, therefore there is following technical problem: the one, hydrochloric acid easily volatilizees, in the process of heating hydrolysis, reaction is violent, produce a large amount of acid mists, easily cause the corrosion of conversion unit, easily to environment, and aftertreatment is also more difficult.In CN200810088877.5, in water content, lower than 18% citric acid waste residues productive rate, also only have 3～6%.
Summary of the invention
The objective of the invention is to provide in order to solve above-mentioned technical problem a kind of preparation method of D-Glucosamine Hydrochloride, the citric acid waste residues that this preparation method take after the fermentative Production citric acid is raw material, the mixing acid that hydrochloric acid and acetic acid forms of take is hydrolysing agent, through hydrolysis, filtration, decolouring, suction filtration, crystallization, the steps such as oven dry finally obtain D-Glucosamine Hydrochloride successively.The D-Glucosamine Hydrochloride productive rate of this preparation method's gained is high, simultaneously by adding acetic acid, reduces the use of the hydrochloric acid in acidolysis, reduces the corrosion to production unit, reduces production costs simultaneously.
Technical scheme of the present invention
A kind of preparation method of D-Glucosamine Hydrochloride, the citric acid waste residues of take after the fermentative Production citric acid is raw material, the mixing acid that hydrochloric acid and acetic acid were formed of take is hydrolysing agent, successively through hydrolysis, filtration, decolouring, suction filtration, crystallization, the steps such as oven dry finally obtain D-Glucosamine Hydrochloride, and its preparation process specifically comprises the following steps:
(1), hydrolysis:
By citric acid waste residues, with after mixing acid mixes, the control mixing speed is 300-800r/min, and temperature is 80～100 ℃ and is reacted 3～5h;
Above-mentioned citric acid waste residues used and the amount of mixing acid, press mass volume ratio and calculate, be i.e. citric acid waste residues: mixing acid is 1g:4～10mL;
Described mixing acid, the hydrochloric acid that is 30～38% by mass percent and anhydrous acetic acid, calculate by volume, and the hydrochloric acid that mass percent is 30～38%: the ratio that anhydrous acetic acid is 1:1～2 mixes;
Described citric acid waste residues is that the fermentation plant that moisture content is 20-30% produces citric acid gained citric acid waste residues;
(2), suction filtration:
Treat that step (1) reacts complete, the reaction solution of gained is chilled to room temperature, suction filtration then, the filter cake of gained is 6.0～7.0 by deionized water wash to the pH value of elutant, merging filtrate and elutant, obtain amalgamation liquid;
The amalgamation liquid of above-mentioned gained being controlled on Rotary Evaporators to vacuum tightness is that 0.08～0.10MPa carries out underpressure distillation, be concentrated into reduction in bulk half;
(3), decolouring:
Concentrated solution and the gac of step (2) gained are calculated in mass ratio, it is concentrated solution: the ratio that gac is 1:0.2～0.5, add gac in the concentrated solution of step (2) gained, the control mixing speed is 300-800r/min, and temperature is 80～100 ℃ of 2～5h that decoloured;
(4), suction filtration:
Be chilled to room temperature after step (3) decolouring, suction filtration then, the filter cake of gained is neutral by deionized water wash to elutant, merging filtrate and elutant, obtain amalgamation liquid;
(5), crystallization:
Amalgamation liquid by step (4) gained, control pressure is 0.08～0.10MPa, temperature is 50～80 ℃ and concentrated, treat the volume simmer down to original 10%～20%, stop heating, be incorporated as the amalgamation liquid volume 0.1-1 dehydrated alcohol doubly of step (4) gained, be cooled to gradually room temperature, then 0 ℃ of lower crystallization, after refrigerating 4～8h, filter, and rinse crystal with dehydrated alcohol;
Then repeatedly recrystallization is carried out in the repetition of the filtrate after crystallization above-mentioned steps (3), (4), until can not have again crystal out;
(6), dry:
It is that 0.08～0.10MPa, temperature are 60～75 ℃ and carry out drying 2～6h that whole crystal of the final gained of step (5) are controlled to vacuum tightnesss, obtains D-Glucosamine Hydrochloride.
Beneficial effect of the present invention
The preparation method of a kind of D-Glucosamine Hydrochloride of the present invention, because the hydrolysis reaction in preparation process adopts hydrochloric acid and acetic acid mixing acid system, thereby produce the problem of a large amount of acid mists while effectively having solved the simple heating hydrolysis produced during with hydrochloric acid, reduced the usage quantity of hydrochloric acid, further reduced the extent of corrosion to production unit, final D-Glucosamine Hydrochloride productive rate reaches 5.0～5.2%.
Further, the preparation method of a kind of D-Glucosamine Hydrochloride of the present invention, owing to take citric acid waste residues that fermentation plant produces the citric acid gained, obtain as raw material produced, be about to resource and carry out recycle, because raw material resources are abundant, the resources of production are unrestricted simultaneously, and production cost is low, this has also further saved the expense of administering environment, has good society and economic benefit.
Embodiment
Below by specific embodiment, the present invention is further set forth, but do not limit the present invention.
embodiment 1
A kind of preparation method of D-Glucosamine Hydrochloride, the citric acid waste residues of take after the fermentative Production citric acid is raw material, the mixing acid that hydrochloric acid and acetic acid forms of take is hydrolysing agent, successively through hydrolysis, filtration, decolouring, suction filtration, crystallization, the steps such as oven dry finally obtain D-Glucosamine Hydrochloride, and its preparation process specifically comprises the following steps:
(1), hydrolysis:
The citric acid waste residues that is 20% by the 100g moisture content joins 1000mL with in the whipping appts there-necked flask, and after adding the mixing acid of 800mL amount, the control mixing speed is 300r/min, and temperature is 80 ℃ and is reacted 3h;
The citric acid waste residues that above-mentioned moisture content used is 20% and the amount of mixing acid, press mass volume ratio and calculate, and the citric acid waste residues that moisture content is 20%: mixing acid is 1g:4mL;
Described mixing acid calculates by volume, the hydrochloric acid that mass percent is 30%: anhydrous acetic acid is 1:1, and the hydrochloric acid that is 30% by mass percent and anhydrous acetic acid, mix;
The citric acid waste residues that described moisture content is 20% is that fermentation plant produces the citric acid gained;
(2), suction filtration:
Treat that (1) react complete, be chilled to room temperature, then suction filtration, make solid-liquid thoroughly separate, the filter cake of gained is 7.0 by deionized water wash to the pH value of elutant, and merging filtrate and elutant, obtain amalgamation liquid, then the amalgamation liquid of gained being controlled to vacuum tightness is that 0.08～0.10MPa carries out underpressure distillation, be concentrated into reduction in bulk half;
(3), decolouring:
The concentrated solution of step (2) gained is transferred to 500mL with in the whipping appts there-necked flask, concentrated solution and the gac of step (2) gained are calculated in mass ratio, it is concentrated solution: the ratio that gac is 1:0.2, add gac in the concentrated solution of step (2) gained, the control mixing speed is 800r/min, and temperature is 100 ℃ of 2h that decoloured;
(4), suction filtration:
Treat that (4) decolour completely, be chilled to room temperature, then suction filtration, thoroughly separate solid-liquid, and the filter cake of gained is neutral by deionized water wash to elutant, and merging filtrate and elutant, obtain amalgamation liquid;
(5), crystallization:
The amalgamation liquid of step (4) gained is transferred in the 500mL pear shape bottle, control pressure is 0.10MPa, and temperature is 65 ℃ and concentrated, treat the volume simmer down to original 12%, mass crystallization appears, stop heating, be incorporated as the dehydrated alcohol of 0.1 times of the amalgamation liquid volume of step (4) gained, progressively be cooled to room temperature, then 0 ℃ of lower crystallization, refrigeration 4h, filter, and rinse crystal with dehydrated alcohol;
Then repeatedly recrystallization is carried out in filtrate repetition above-mentioned steps (3), (4) after above-mentioned crystallization, until can not have again crystal out;
(6), dry:
It is that 0.10MPa, temperature are 70 ℃ and carry out dry 2h that whole crystal of the final gained of step (5) are controlled to vacuum tightnesss, obtains the 5.1gD-glucosamine hydrochloride, and productive rate is 5.1%.
embodiment 2
A kind of preparation method of D-Glucosamine Hydrochloride, the citric acid waste residues of take after the fermentative Production citric acid is raw material, the mixing acid that hydrochloric acid and acetic acid forms of take is hydrolysing agent, successively through hydrolysis, filtration, decolouring, suction filtration, crystallization, the steps such as oven dry finally obtain D-Glucosamine Hydrochloride, and its preparation process specifically comprises the following steps:
(1), hydrolysis:
The citric acid waste residues that is 30% by the 100g moisture content joins 1000mL with in the whipping appts there-necked flask, and after adding the mixing acid of 400mL amount, the control mixing speed is 500r/min, and temperature is 100 ℃ and is reacted 4h;
The citric acid waste residues that above-mentioned moisture content used is 30% and the amount of mixing acid, press mass volume ratio and calculate, and the citric acid waste residues that moisture content is 30%: mixing acid is 1g:6mL;
Described mixing acid calculates by volume, the hydrochloric acid that mass percent is 30%: anhydrous acetic acid is 1:2, and the hydrochloric acid that is 30% by mass percent and anhydrous acetic acid, mix;
The citric acid waste residues that described moisture content is 30% is that fermentation plant produces the citric acid gained;
(2), suction filtration:
Treat that (1) react complete, be chilled to room temperature, then suction filtration, solid-liquid is thoroughly separated, the filter cake of gained is 6.0 by deionized water wash to the pH value of elutant, and merging filtrate and elutant, obtain amalgamation liquid, then the amalgamation liquid of gained being controlled to vacuum tightness is that 0.08～0.10MPa carries out underpressure distillation, be concentrated into reduction in bulk half;
(3), decolouring:
The concentrated solution of step (2) gained is transferred to 500mL with in the whipping appts there-necked flask, concentrated solution and the gac of step (2) gained are calculated in mass ratio, it is concentrated solution: the ratio that gac is 1:0.5, add gac in the concentrated solution of step (2) gained, the control mixing speed is 300r/min, and temperature is 90 ℃ of 2h that decoloured;
(4), suction filtration:
Treat that (3) decolour completely, be chilled to room temperature, then suction filtration, make solid-liquid thoroughly separate, and the filter cake of gained is neutral by deionized water wash to elutant, and merging filtrate and elutant, obtain amalgamation liquid;
(5), crystallization:
Above-mentioned amalgamation liquid is transferred in the 500mL pear shape bottle, control pressure is 0.09MPa, and temperature is 50 ℃ and concentrated, treat the volume simmer down to original 20%, mass crystallization appears, stop heating, be incorporated as the dehydrated alcohol of 1.0 times of the amalgamation liquid volumes of step (4) gained, progressively be cooled to room temperature, then 0 ℃ of lower crystallization, refrigeration 8h, filter, and rinse crystal with dehydrated alcohol;
Then repeatedly recrystallization is carried out in filtrate repetition above-mentioned steps (3), (4) after crystallization, until can not have again crystal out;
(6), dry:
It is that 0.08MPa, temperature are 65 ℃ and carry out dry 4h that whole crystal of the final gained of step (5) are controlled to vacuum tightnesss, obtains the 5.20gD-glucosamine hydrochloride, and productive rate is 5.2%.
embodiment 3
A kind of preparation method of D-Glucosamine Hydrochloride, the citric acid waste residues of take after the fermentative Production citric acid is raw material, the mixing acid that hydrochloric acid and acetic acid forms of take is hydrolysing agent, successively through hydrolysis, filtration, decolouring, suction filtration, crystallization, the steps such as oven dry finally obtain D-Glucosamine Hydrochloride, and its preparation process specifically comprises the following steps:
(1), hydrolysis:
The citric acid waste residues that is 24% by the moisture content of 200g joins 1000mL with in the whipping appts there-necked flask, and after adding 1000mL mixing acid, the control mixing speed is 800r/min, and temperature is 85 ℃ and is reacted 5h;
The citric acid waste residues of 100～200g that above-mentioned moisture content used is 24% and the amount of mixing acid, press mass volume ratio and calculate, and the citric acid waste residues of 100～200g that moisture content is 24%: mixing acid is 1g:10mL;
Described mixing acid calculates by volume, the hydrochloric acid that mass percent is 38%: anhydrous acetic acid is 1:2, and the hydrochloric acid that is 38% by mass percent and anhydrous acetic acid, mix;
The citric acid waste residues that described moisture content is 24% is that fermentation plant produces the citric acid gained;
(2), suction filtration:
Treat that step (1) reacts complete, be chilled to room temperature, then suction filtration, make solid-liquid thoroughly separate, the filter cake of gained is 7.0 by deionized water wash to the pH value of elutant, and merging filtrate and elutant, obtain amalgamation liquid, then the amalgamation liquid of gained being controlled to vacuum tightness is that 0.08～0.10MPa carries out underpressure distillation, be concentrated into reduction in bulk half;
(3), decolouring:
Step (2) concentrated solution is transferred to 500mL with in the whipping appts there-necked flask, concentrated solution and the gac of step (2) gained are calculated in mass ratio, it is concentrated solution: the ratio that gac is 1:0.5, add gac in the concentrated solution of step (2) gained, the control mixing speed is 600r/min, and temperature is 100 ℃ of 3h that decoloured;
(4), suction filtration:
Treat that step (3) decolours completely, be chilled to room temperature, then suction filtration, make solid-liquid thoroughly separate, and the filter cake of gained is neutral by deionized water wash to elutant, and merging filtrate and elutant, obtain amalgamation liquid;
(5), crystallization:
The amalgamation liquid of step (4) gained is transferred in the 500mL pear shape bottle, control pressure is 0.08MPa, and temperature is 80 ℃ and concentrated, treat the volume simmer down to original 20%, mass crystallization appears, stop heating, be incorporated as the dehydrated alcohol of 0.6 times of the amalgamation liquid volume of step (4) gained, progressively be cooled to room temperature, then 0 ℃ of crystallization, refrigeration 6h, filter, and rinse crystal with dehydrated alcohol;
Then repeatedly recrystallization is carried out in filtrate repetition above-mentioned steps (3), (4) after crystallization, until can not have again crystal out;
(6), dry:
It is that 0.10MPa, temperature are 70 ℃ and carry out dry 6h that whole crystal of the final gained of step (5) are controlled to vacuum tightnesss, obtains the 5.00gD-glucosamine hydrochloride, and productive rate is 5.0%.
Result by the above embodiments 1～3 gained shows: the mixing acid that adds hydrochloric acid-acetic acid to form can reduce the usage quantity of hydrochloric acid effectively, improve the acid mist phenomenon in producing, make preparation process be simplified, the productive rate of D-Glucosamine Hydrochloride can reach 5-5.2% simultaneously.
Above said content is the basic explanation under conceiving for the present invention only, and, according to any equivalent transformation that technical scheme of the present invention is done, all should belong to protection scope of the present invention.
Claims (3)
1. the preparation method of a D-Glucosamine Hydrochloride, the citric acid waste residues of take after the fermentative Production citric acid is raw material, it is characterized in that take that the mixing acid that hydrochloric acid and acetic acid were formed is hydrolysing agent, citric acid waste residues after the fermentative Production citric acid, successively through hydrolysis, filtration, activated carbon decolorizing, suction filtration, crystallization, oven dry, is finally obtained to D-Glucosamine Hydrochloride.
2. the preparation method of a kind of D-Glucosamine Hydrochloride as claimed in claim 1, it is characterized in that the mixing acid that described hydrochloric acid and acetic acid form, the hydrochloric acid that is 30～38% by mass percent and anhydrous acetic acid, calculate by volume, the hydrochloric acid that mass percent is 30～38%: the ratio that anhydrous acetic acid is 1:1～2 mixes;
Described citric acid waste residues is that the fermentation plant that moisture content is 20-30% produces citric acid gained citric acid waste residues.
3. the preparation method of a kind of D-Glucosamine Hydrochloride as claimed in claim 1 or 2 is characterized in that specifically comprising the following steps:
(1), by citric acid waste residues with after mixing acid mixes, the control mixing speed is 300-800r/min, temperature is 80～100 ℃ and is reacted 3～5h;
The amount of the mixing acid that above-mentioned citric acid waste residues used and hydrochloric acid and anhydrous acetic acid form, press mass volume ratio and calculate, be i.e. citric acid waste residues: the mixing acid that hydrochloric acid and anhydrous acetic acid form is 1g:4～10mL;
(2), treat that step (1) reacts complete, the reaction solution of gained is chilled to room temperature, suction filtration then, and be the gained filter cake 6～7 with deionized water wash to elutant pH value, merging filtrate and elutant, obtain amalgamation liquid;
The amalgamation liquid of above-mentioned gained being controlled on Rotary Evaporators to vacuum tightness is that 0.08～0.10MPa carries out underpressure distillation, be concentrated into reduction in bulk half;
(3), concentrated solution and the gac of step (2) gained are calculated in mass ratio, i.e. concentrated solution: the ratio that gac is 1:0.2～0.5, the control mixing speed is 300-800r/min, temperature is 80～100 ℃ of 2～5h that decoloured;
(4), be chilled to room temperature after step (3) decolouring, suction filtration then, the gained filter cake is neutral by deionized water wash to elutant, merging filtrate and elutant, obtain amalgamation liquid;
(5), by the amalgamation liquid of step (4) gained, control vacuum tightness is 0.08～0.10MPa, temperature is 50～80 ℃ and concentrated, treat the volume simmer down to original 10%～20%, stop heating, be incorporated as the amalgamation liquid volume 0.1-1.0 dehydrated alcohol doubly of step (4) gained, be cooled to gradually room temperature, then 0 ℃ of lower crystallization, after refrigerating 4～8h, filter, and rinse crystal with dehydrated alcohol;
Then the filtrate after above-mentioned crystallization is repeated to above-mentioned step
(3), (4)carry out repeatedly recrystallization, until can not have again crystal out;
(6), whole crystal of the final gained of step (5) are controlled to vacuum tightnesss is that 0.08～0.10MPa, temperature are 60～75 ℃ and carry out vacuum-drying, obtains D-Glucosamine Hydrochloride.
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| CN110590867A (en) * | 2019-09-12 | 2019-12-20 | 河南巨龙生物工程股份有限公司 | Synthesis method of D-glucosamine hydrochloride |
| CN112851724A (en) * | 2021-02-20 | 2021-05-28 | 江苏澳新生物工程有限公司 | Preparation method of vegetarian D-glucosamine hydrochloride |
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Application publication date: 20131218 |