CN112375111A - Production process and application of glucosamine - Google Patents
Production process and application of glucosamine Download PDFInfo
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- CN112375111A CN112375111A CN202011421144.6A CN202011421144A CN112375111A CN 112375111 A CN112375111 A CN 112375111A CN 202011421144 A CN202011421144 A CN 202011421144A CN 112375111 A CN112375111 A CN 112375111A
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- 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- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen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
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- 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
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Abstract
The invention relates to the technical field of glucosamine, in particular to a production process and application of glucosamine, which comprises the following steps: (1) hydrolyzing chitin or chitosan under acidic hydrogen peroxide, adding sodium hydroxide to remove redundant acid, and filtering the hydrolysate to obtain glucosamine hydrochloride solution; (2) mixing the glucosamine hydrochloride solution with an adsorption-type decolorizing agent, and then carrying out solid-liquid separation; (3) allowing the glucosamine hydrochloride solution treated in the step (2) to pass through a cation exchange membrane and then an anion exchange membrane to obtain a glucosamine solution; (4) and (3) concentrating and crystallizing the glucosamine solution under the vacuum condition to obtain the glucosamine. The invention utilizes hydrogen peroxide to carry out synergistic hydrolysis on chitin or chitosan under the acidic condition, thereby being more efficient and clean. The glucosamine hydrochloride solution can be effectively desalted by adopting a cation exchange membrane and an anion exchange membrane.
Description
Technical Field
The invention relates to the technical field of glucosamine, in particular to a production process and application of glucosamine.
Background
The following in the background art merely refers to information that is understood by the inventor to be relevant to the present invention and is intended to augment understanding of the present invention through a description of some basic technical knowledge related to the present invention, which information does not necessarily have to constitute knowledge that is well known by those of ordinary skill in the art.
Glucosamine (formula C)6H13NO5) Is natural glucosamine, and has effects of repairing articular cartilage, promoting secretion of joint fluid, promoting generation of joint synovial fluid, effectively reducing friction of joint surface, relieving joint pain and swelling, and recovering joint space. Currently, glucosamine is obtained by hydrolyzing chitin and then performing refining procedures such as sodium hydroxide deacidification, decolorization, crystallization and the like. However, the glucosamine hydrochloride obtained by the method contains a large amount of sodium chloride, and the preparation of glucosamine monomer without sodium chloride is an effective way to overcome the problems because the arthritis patients suffering from hypertension or cardiovascular diseases are easily affected by chloride ions.
Disclosure of Invention
The main object of the present invention is to prepare a glucosamine product that contains as little sodium chloride as possible or that is kept at a low level. Therefore, the invention provides a production process and application of glucosamine, and the method can effectively reduce the content of sodium chloride in the glucosamine and reduce the influence on patients with arthritis of hypertension or cardiovascular diseases. In order to realize the purpose, the invention discloses the following technical scheme:
on one hand, the invention discloses a production process of glucosamine, which comprises the following steps:
(1) hydrolyzing chitin or chitosan under acidic hydrogen peroxide, adding sodium hydroxide to remove redundant acid, and filtering the hydrolysate to obtain glucosamine hydrochloride solution;
(2) mixing the glucosamine hydrochloride solution obtained in the step (1) with an adsorption-type decolorizing agent, and then carrying out solid-liquid separation;
(3) allowing the glucosamine hydrochloride solution treated in the step (2) to pass through a cation exchange membrane and then an anion exchange membrane to remove sodium ions, chloride ions and the like in the solution to obtain a glucosamine solution;
(4) and (4) concentrating and crystallizing the glucosamine solution obtained in the step (3) under a vacuum condition to obtain the glucosamine solution.
Preferably, in the step (1), the acidic hydrogen peroxide is a mixed solution of an acid solution and hydrogen peroxide, the mass concentration of the acid in the mixed solution is 2-3.5%, the mass concentration of the hydrogen peroxide is 3-8.5%, and the hydrolysis time is 2-4 h. Preferably, the acid solution is hydrochloric acid. The chitin or chitosan is subjected to synergistic hydrolysis by using hydrogen peroxide under an acidic condition, so that the chitin or chitosan is more efficient and cleaner.
Preferably, in the step (1), the ratio of the acidic hydrogen peroxide to the chitin or chitosan is 5-12 mL: 1-3 g. Adding excessive acidic hydrogen peroxide ensures that the chitin or chitosan can be fully hydrolyzed.
Preferably, in the step (1), the addition amount of the sodium hydroxide is based on adjusting the pH value of the hydrolysate to be neutral, the pH value of the hydrolysate is monitored in real time in the addition process, and the addition of the sodium hydroxide is stopped after a preset requirement is met.
Preferably, in step (1), the hydrolysis process is carried out under heat and pressure. Optionally, the heating temperature is 40-60 ℃, and the pressurizing pressure is not less than 0.2 MPa. The hydrolysis is carried out under the conditions of heating and pressurizing, so that the hydrolysis process is promoted.
Preferably, in the step (2), the adsorption-type decolorant includes any one of activated carbon, adsorption resin, and the like. The decoloring agent decolors the glucosamine hydrochloride solution, and simultaneously removes partial chloride ions and other journal ions by utilizing the adsorption effect of the decoloring agent, so that the purity of the glucosamine hydrochloride solution is improved.
Preferably, in the step (2), the solid-liquid separation method includes any one of filtration, centrifugation, and the like.
Preferably, in step (3), the glucosamine solution obtained is repeatedly passed through a cation exchange membrane and then through an anion exchange membrane, so as to more thoroughly remove sodium chloride from the glucosamine solution.
Preferably, in the step (4), the temperature of the concentration crystallization is 50 to 65 ℃, and the time is adjusted according to the need, and the invention is not particularly limited.
On the other hand, the invention discloses the application of the production process of the glucosamine in the preparation of the glucosamine, the preparation of arthritis treatment drugs and the like.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention takes acidic hydrogen peroxide as a hydrolytic agent to hydrolyze chitin or chitosan, which obviously reduces the use of a large amount of concentrated hydrochloric acid in the traditional method taking concentrated hydrochloric acid as the hydrolytic agent; and secondly, the chemical bond of the chitin or the chitosan is easier to break under the acidic condition, so that the hydrogen peroxide can be more fully contacted with the products after the initial hydrolysis, and the hydrolysis reaction is quicker and more efficient.
(2) The invention adopts the cation exchange membrane and the anion exchange membrane to effectively desalt the glucosamine hydrochloride solution, compared with some traditional methods, the method has better and more thorough desalting effect, does not introduce additional impurity ions, and obtains the glucosamine with higher purity and better quality.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. The invention will now be further illustrated by specific examples.
Example 1
A production process of glucosamine comprises the following steps:
(1) mixing chitosan and acidic hydrogen peroxide (the mass concentration of hydrochloric acid is 2%, and the mass concentration of hydrogen peroxide is 5%) according to the weight ratio of 1 g: mixing the chitosan with 5mL of water according to a proportion, hydrolyzing chitosan by using hydrogen peroxide under an acidic condition, wherein the hydrolysis process is carried out under a heating and pressurizing condition, the heating temperature is 40 ℃, the pressurizing pressure is 0.25MPa, adding sodium hydroxide to remove redundant acid after hydrolyzing for 4h, monitoring the pH value of the hydrolysate in real time during the adding process, stopping adding the sodium hydroxide after the hydrolysate is neutral, and filtering the hydrolysate to separate out liquid, namely glucosamine hydrochloride solution.
(2) And (2) mixing the glucosamine hydrochloride solution obtained in the step (1) with activated carbon, decoloring for 1.2h, filtering, and separating out the activated carbon to obtain liquid, namely the decolored glucosamine hydrochloride solution for later use.
(3) And (3) enabling the decolored glucosamine hydrochloride solution to pass through a cation exchange membrane, then pass through an anion exchange membrane, and repeating the steps for three times to fully remove sodium ions and chloride ions in the solution, so as to realize the desalination of the glucosamine hydrochloride solution and obtain the glucosamine solution.
(4) And (4) concentrating and crystallizing the glucosamine solution obtained in the step (3) at 50 ℃ for 1h under a vacuum condition to obtain glucosamine powder.
Example 2
A production process of glucosamine comprises the following steps:
(1) mixing chitosan and acidic hydrogen peroxide (the mass concentration of hydrochloric acid is 3%, and the mass concentration of hydrogen peroxide is 6.5%) according to the weight ratio of 2 g: mixing 8mL of the mixture in a proportion, hydrolyzing chitosan by using hydrogen peroxide under an acidic condition, and hydrolyzing under a heating and pressurizing condition, wherein the heating temperature is 50 ℃, the pressurizing pressure is 0.2MPa, adding sodium hydroxide to remove redundant acid after hydrolyzing for 3.8h, monitoring the pH value of the hydrolysate in real time during the adding process, stopping adding the sodium hydroxide after the hydrolysate is neutral, and filtering the hydrolysate to separate out liquid, namely glucosamine hydrochloride solution.
(2) And (2) mixing the glucosamine hydrochloride solution obtained in the step (1) with activated carbon, decoloring for 1.5h, filtering, and separating out the activated carbon to obtain liquid, namely the decolored glucosamine hydrochloride solution for later use.
(3) And (3) enabling the decolored glucosamine hydrochloride solution to pass through a cation exchange membrane, then pass through an anion exchange membrane, and repeating the steps for three times to fully remove sodium ions and chloride ions in the solution, so as to realize the desalination of the glucosamine hydrochloride solution and obtain the glucosamine solution.
(4) And (4) concentrating and crystallizing the glucosamine solution obtained in the step (3) at 60 ℃ for 1h under a vacuum condition to obtain glucosamine powder.
Example 3
A production process of glucosamine comprises the following steps:
(1) mixing chitosan and acidic hydrogen peroxide (the mass concentration of hydrochloric acid is 3.5%, and the mass concentration of hydrogen peroxide is 8.5%) according to the weight ratio of 3 g: 12mL, hydrolyzing chitosan by using hydrogen peroxide under an acidic condition, wherein the hydrolysis process is carried out under the conditions of heating and pressurizing, the heating temperature is 55 ℃, the pressurizing pressure is 0.3MPa, adding sodium hydroxide to remove redundant acid after hydrolyzing for 2h, monitoring the pH value of the hydrolysate in real time during the adding process, stopping adding the sodium hydroxide after the hydrolysate is neutral, and filtering the hydrolysate to separate out liquid, namely the glucosamine hydrochloride solution.
(2) And (2) mixing the glucosamine hydrochloride solution obtained in the step (1) with adsorption resin, decoloring for 1.5h, filtering, and separating out the adsorption resin to obtain a liquid, namely the decolored glucosamine hydrochloride solution for later use.
(3) And (3) enabling the decolored glucosamine hydrochloride solution to pass through a cation exchange membrane, then pass through an anion exchange membrane, and repeating the steps for three times to fully remove sodium ions and chloride ions in the solution, so as to realize the desalination of the glucosamine hydrochloride solution and obtain the glucosamine solution.
(4) And (4) concentrating and crystallizing the glucosamine solution obtained in the step (3) at 55 ℃ for 1.5h under vacuum condition to obtain glucosamine powder.
Example 4
A production process of glucosamine comprises the following steps:
(1) mixing chitosan and acidic hydrogen peroxide (the mass concentration of hydrochloric acid is 2.5%, and the mass concentration of hydrogen peroxide is 3%) according to the weight ratio of 3 g: mixing 10mL of the mixture according to a proportion, hydrolyzing chitosan by using hydrogen peroxide under an acidic condition, wherein the hydrolysis process is carried out under a heating and pressurizing condition, the heating temperature is 60 ℃, the pressurizing pressure is 0.3MPa, gradually adding sodium hydroxide to remove redundant acid after hydrolyzing for 3.5h, monitoring the pH value of the hydrolysate in real time during the adding process, stopping adding the sodium hydroxide after the hydrolysate is neutral, and filtering the hydrolysate to separate out liquid, namely glucosamine hydrochloride solution.
(2) And (2) mixing the glucosamine hydrochloride solution obtained in the step (1) with activated carbon, decoloring for 1.5h, filtering, and separating out the activated carbon to obtain liquid, namely the decolored glucosamine hydrochloride solution for later use.
(3) And (3) enabling the decolored glucosamine hydrochloride solution to pass through a cation exchange membrane, then pass through an anion exchange membrane, and repeating the steps for three times to fully remove sodium ions and chloride ions in the solution, so as to realize the desalination of the glucosamine hydrochloride solution and obtain the glucosamine solution.
(4) And (4) concentrating and crystallizing the glucosamine solution obtained in the step (3) at 65 ℃ for 1h under a vacuum condition to obtain glucosamine powder.
Example 5
A production process of glucosamine comprises the following steps:
(1) mixing chitosan and acidic hydrogen peroxide (the mass concentration of hydrochloric acid is 3.0%, and the mass concentration of hydrogen peroxide is 7%) according to the weight ratio of 1 g: 8mL of the chitosan is mixed according to a proportion, hydrogen peroxide is used for hydrolyzing chitosan under an acidic condition, the hydrolysis process is carried out under a heating and pressurizing condition, wherein the heating temperature is 45 ℃, the pressurizing pressure is 0.32MPa, sodium hydroxide is gradually added after 2.5h of hydrolysis to remove redundant acid, the pH value of the hydrolysate is monitored in real time in the adding process, the addition of the sodium hydroxide is stopped after the hydrolysate is neutral, and then the hydrolysate is filtered to separate out liquid, namely glucosamine hydrochloride solution.
(2) And (2) mixing the glucosamine hydrochloride solution obtained in the step (1) with adsorption resin, decoloring for 1h, filtering, and separating out the adsorption resin to obtain a liquid, namely the decolored glucosamine hydrochloride solution for later use.
(3) And (3) enabling the decolored glucosamine hydrochloride solution to pass through a cation exchange membrane, then pass through an anion exchange membrane, and repeating the steps for three times to fully remove sodium ions and chloride ions in the solution, so as to realize the desalination of the glucosamine hydrochloride solution and obtain the glucosamine solution.
(4) And (4) concentrating and crystallizing the glucosamine solution obtained in the step (3) at 55 ℃ for 1.5h under vacuum condition to obtain glucosamine powder.
Test example 1
A production process of glucosamine comprises the following steps:
(1) mixing chitosan and hydrochloric acid (mass concentration is 2%) according to the weight ratio of 1 g: mixing the chitosan with 5mL of water according to a proportion, hydrolyzing chitosan by using hydrogen peroxide under an acidic condition, and hydrolyzing under a heating and pressurizing condition, wherein the heating temperature is 40 ℃, the pressurizing pressure is 0.25MPa, adding sodium hydroxide to remove redundant acid after hydrolyzing for 4h, monitoring the pH value of the hydrolysate in real time during the adding process, stopping adding the sodium hydroxide after the hydrolysate is neutral, and filtering the hydrolysate to separate out liquid, namely glucosamine hydrochloride solution;
(2) and (2) mixing the glucosamine hydrochloride solution obtained in the step (1) with activated carbon, decoloring for 1.2h, filtering, and separating out the activated carbon to obtain liquid, namely the decolored glucosamine hydrochloride solution for later use.
(3) Enabling the decolored glucosamine hydrochloride solution to pass through a cation exchange membrane, then pass through an anion exchange membrane, and repeating the steps for three times to fully remove sodium ions and chloride ions in the solution, so as to realize the desalination of the glucosamine hydrochloride solution and obtain the glucosamine solution;
(4) and (4) concentrating and crystallizing the glucosamine solution obtained in the step (3) at 50 ℃ for 1h under a vacuum condition to obtain glucosamine powder.
Test example 2
A production process of glucosamine comprises the following steps:
(1) mixing chitosan and hydrogen peroxide (the mass concentration of hydrogen peroxide is 5%) according to the weight ratio of 1 g: mixing the chitosan with 5mL of water according to a proportion, hydrolyzing chitosan by using hydrogen peroxide under an acidic condition, and hydrolyzing under a heating and pressurizing condition, wherein the heating temperature is 40 ℃, the pressurizing pressure is 0.25MPa, adding sodium hydroxide to remove redundant acid after hydrolyzing for 4h, monitoring the pH value of the hydrolysate in real time during the adding process, stopping adding the sodium hydroxide after the hydrolysate is neutral, and filtering the hydrolysate to separate out liquid, namely glucosamine hydrochloride solution;
(2) and (2) mixing the glucosamine hydrochloride solution obtained in the step (1) with activated carbon, decoloring for 1.2h, filtering, and separating out the activated carbon to obtain liquid, namely the decolored glucosamine hydrochloride solution for later use.
(3) And (3) enabling the decolored glucosamine hydrochloride solution to pass through a cation exchange membrane, then pass through an anion exchange membrane, and repeating the steps for three times to fully remove sodium ions and chloride ions in the solution, so as to realize the desalination of the glucosamine hydrochloride solution and obtain the glucosamine solution.
(4) And (4) concentrating and crystallizing the glucosamine solution obtained in the step (3) at 50 ℃ for 1h under a vacuum condition to obtain glucosamine powder.
Test example 3
A production process of glucosamine comprises the following steps:
(1) mixing chitosan and acidic hydrogen peroxide (the mass concentration of hydrochloric acid is 2%, and the mass concentration of hydrogen peroxide is 5%) according to the weight ratio of 1 g: mixing the chitosan with 5mL of water according to a proportion, hydrolyzing chitosan by using hydrogen peroxide under an acidic condition, and hydrolyzing under a heating and pressurizing condition, wherein the heating temperature is 40 ℃, the pressurizing pressure is 0.25MPa, adding sodium hydroxide to remove redundant acid after hydrolyzing for 4h, monitoring the pH value of the hydrolysate in real time during the adding process, stopping adding the sodium hydroxide after the hydrolysate is neutral, and filtering the hydrolysate to separate out liquid, namely glucosamine hydrochloride solution;
(2) and (2) mixing the glucosamine hydrochloride solution obtained in the step (1) with activated carbon, decoloring for 1.2h, filtering, and separating out the activated carbon to obtain liquid, namely the decolored glucosamine hydrochloride solution for later use.
(4) And (4) concentrating and crystallizing the glucosamine hydrochloride solution obtained in the step (4) at 50 ℃ for 1h under a vacuum condition to obtain glucosamine powder.
As shown in table 1, it can be seen that the purity of glucosamine powder prepared in the above examples and test examples can be improved by effectively removing sodium chloride from glucosamine using the method of the example. In addition, as can be seen from the glucosamine yield in test example 1 and test example 2, when the raw material is hydrolyzed using acidic hydrogen peroxide, the degree of hydrolysis can be significantly increased, and the utilization rate of the raw material can be improved.
TABLE 1
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The production process of glucosamine is characterized by comprising the following steps:
(1) hydrolyzing chitin or chitosan under acidic hydrogen peroxide, adding sodium hydroxide to remove redundant acid, and filtering the hydrolysate to obtain glucosamine hydrochloride solution;
(2) mixing the glucosamine hydrochloride solution obtained in the step (1) with an adsorption-type decolorizing agent, and then carrying out solid-liquid separation;
(3) allowing the glucosamine hydrochloride solution treated in the step (2) to pass through a cation exchange membrane and then an anion exchange membrane to remove sodium ions and chloride ions in the solution to obtain a glucosamine solution;
(4) and (4) concentrating and crystallizing the glucosamine solution obtained in the step (3) under a vacuum condition to obtain the glucosamine solution.
2. The glucosamine production process according to claim 1, wherein in the step (1), the acidic hydrogen peroxide is a mixed solution of an acid solution and hydrogen peroxide; preferably, the mass concentration of the acid in the mixed solution is 2-3.5%, the mass concentration of the hydrogen peroxide is 2-15%, and the hydrolysis time is 2-4 h.
3. The process for producing glucosamine according to claim 2, wherein the acid solution is any one of hydrochloric acid, formic acid, and acetic acid; preferably, the ratio of the acidic hydrogen peroxide to the chitin or chitosan is 5-12 mL: 1-3 g.
4. The process for producing glucosamine according to claim 1, wherein the sodium hydroxide is added in step (1) to adjust the pH of the hydrolysate to neutral.
5. The process for producing glucosamine according to claim 1, wherein the hydrolysis is performed under heat and pressure in step (1); preferably, the heating temperature is 40-60 ℃, and the pressurizing pressure is not less than 0.2 MPa.
6. The process for producing glucosamine according to claim 1, wherein in the step (2), the adsorptive decoloring agent comprises any one of activated carbon and an adsorbent resin.
7. The process for producing glucosamine according to claim 1, wherein the step (3) comprises repeating the step of passing the glucosamine solution through a cation exchange membrane and then through an anion exchange membrane.
8. The process for producing glucosamine according to any one of claims 1 to 7, wherein in the step (2), the solid-liquid separation method comprises any one of filtration and centrifugation.
9. The process for producing glucosamine according to any one of claims 1 to 7, wherein the temperature of the concentration and crystallization in the step (4) is 50 to 65 ℃, and the time is adjusted as needed, and the present invention is not particularly limited.
10. Use of the process for the manufacture of glucosamine according to any one of claims 1 to 9 in the manufacture of a medicament for the treatment of arthritis.
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| CN114191405A (en) * | 2021-11-06 | 2022-03-18 | 山东润德生物科技有限公司 | Preparation method and application of gel type glucosamine preparation |
| CN114230618A (en) * | 2021-12-17 | 2022-03-25 | 扬州日兴生物科技股份有限公司 | Method for preparing glucosamine by using chitin |
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| JP2007191413A (en) * | 2006-01-18 | 2007-08-02 | Protein Chemical Kk | Pure glucosamine and method for producing the same |
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| CN106831895A (en) * | 2017-01-19 | 2017-06-13 | 山东润德生物科技有限公司 | A kind of method of purifying N acetylglucosamines |
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| CN101775045A (en) * | 2009-12-07 | 2010-07-14 | 汪昔奇 | Method for preparing glucosamine hydrochloride |
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Cited By (2)
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| CN114191405A (en) * | 2021-11-06 | 2022-03-18 | 山东润德生物科技有限公司 | Preparation method and application of gel type glucosamine preparation |
| CN114230618A (en) * | 2021-12-17 | 2022-03-25 | 扬州日兴生物科技股份有限公司 | Method for preparing glucosamine by using chitin |
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