CN100422198C - Production process of N-acetyl D-amino glucose - Google Patents
Production process of N-acetyl D-amino glucose Download PDFInfo
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- CN100422198C CN100422198C CNB200610040473XA CN200610040473A CN100422198C CN 100422198 C CN100422198 C CN 100422198C CN B200610040473X A CNB200610040473X A CN B200610040473XA CN 200610040473 A CN200610040473 A CN 200610040473A CN 100422198 C CN100422198 C CN 100422198C
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Abstract
The present invention relates to a production method of N-acetyl D-amino glucose, particularly to a synthetic method of a chemical product. The present invention uses chitin as a starting raw material for preparing D-amino glucose hydrochloride by hydrolysis, namely, a beta-1.4 glycosidic bond is thoroughly hydrolyzed and fractured into monosaccharide, and then the D-amino glucose hydrochloride carries out acidylating reaction with acetic anhydride and triethylamine and then is treated through a series of physical processes to be prepared into a finished product. The present invention has the advantages of simple technology, easy control, convenient production, high product yield which can achieve 85 %, and high application value, the product content can reach 98 to 102 %, and the product has stable product and can completely meet the requirements of actual use.
Description
Technical field
The present invention relates to a kind of synthetic method of Chemicals.
Background technology
The N-acetyl D-amino glucose, be white needle-like crystals, odorlessness, soluble in water, can promote the synthetic of human body mucopolysaccharide, can strengthen immune function of human body, can also synthesize each water-soluble cancer drug that does, sacroiliitis there is the curative effect of anti-inflammatory analgesic,, has vast market prospect in field widespread uses such as food, medicine, chemical industry.Because existing disclosed production method complex process, yield are low, cause production cost high, have limited subsequent production and application.
Summary of the invention
The object of the invention is to invent the production method of the N-acetyl D-amino glucose that a kind of technology is simple, yield is high.
The present invention includes following steps:
1) chitin and excessive hydrochloric acid are hydrolyzed reaction makes the D-glucosamine hydrochloride;
2) with D-glucosamine hydrochloride and aceticanhydride, triethylamine acylation reaction, get thick N-acetyl D-amino glucose through centrifuging and taking;
3) adding sodium bicarbonate in thick N-acetyl D-amino glucose makes with extra care;
4) adopt washing with alcohol, again drying, sieve, make finished product N-acetyl D-amino glucose.
The present invention is a starting raw material with the chitin, by hydrolysis reaction, makes the D-glucosamine hydrochloride, just the thorough hydrolytic cleavage of β-1.4 glycosidic link is become monose, makes finished product with aceticanhydride, triethylamine acylation reaction and the processing of a series of physical process again.Its technology is simple, is easy to control, convenient production, and product yield height can reach 85%, more with using value be, product content can be up to 98～102%, constant product quality can satisfy the requirement of actual use fully.
The principal element that influences hydrolysis reaction has the time and the control of the temperature in the hydrolytic process of concentration of hydrochloric acid and consumption hydrolysis.
In the step 1) of the present invention, the weight ratio of chitin and hydrochloric acid is 1: 5～7.
In the step 1), adopt 35% hydrochloric acid, hydrolysis time is 1.5h ± 0.1h.
In the step 1), adopt 30% hydrochloric acid, hydrolysis time is 2.5h ± 0.1h.
In addition, in the step 1), in hydrolytic process, slowly heat up, under 55～60 ℃ of temperature condition, make chitin transform dissolving, stir, be warming up to little boiling again, back hydrolysis.Suitable temperature can be avoided influencing product appearance quality and purity because of the too fast coking phenomenon that causes that heats up.
In the acylation reaction process, mainly be temperature of reaction control and selection of catalysts.
Step 2) in, be catalyst for reaction with hydrochloric acid, and the weight ratio of catalyzer hydrochloric acid and D-glucosamine hydrochloride is 1: 0.01～0.02, effect is imitated.
Step 2) in, the acylation reaction temperature is 15～20 ℃.Can make anhydrous formation in the resultant of reaction, and aceticanhydride acidylate speed is fast, just can finishes reaction under the normal temps.
In the step 3), through twice refining, purpose is in order to remove the accessory substance vinyl acetic monomer in the product, can to improve the purity of product.
In addition, when refining, vacuum tightness is very big to the quality product influence, if vacuum tightness is too low, temperature is corresponding when refining will improve, and too high temperature will make the feed liquid jaundice, so at 0.09MPa ± 0.005MPa, temperature is controlled at 50 ℃ ± 3 ℃ with vacuum degree control in the present invention.
In step 4), bake out temperature is chosen for 90 ℃～110 ℃.Purpose is to guarantee to wash to give full play to alcoholic acid.
Embodiment
Example one:
1, get the raw materials ready:
Divide another name (amount) get chitin 700kg, 35% hydrochloric acid 4000kg, aceticanhydride 200kg, triethylamine 280kg, _ grease-removing agent (as sodium bicarbonate) 2kg.
2, hydrolysis reaction:
Chitin and 3500kg mixed in hydrochloric acid are added in the reactor, slowly heat up, make chitin transform dissolving under 55～60 ℃ of temperature condition, constantly stir, be warming up to little boiling again, back hydrolysis 1.5h ± 0.1h makes the D-glucosamine hydrochloride.
3, acylation reaction:
With 10kg hydrochloric acid is catalyzer, and D-glucosamine hydrochloride and aceticanhydride, triethylamine are carried out acylation reaction, and the acylation reaction temperature is controlled at 15～20 ℃, through centrifugal, obtains thick N-acetyl D-amino glucose.
4, refining:
Vacuum tightness is that 0.09MPa ± 0.005Mpa, temperature are under 50 ℃ ± 3 ℃ conditions, adds grease-removing agent and make with extra care in thick N-acetyl D-amino glucose; Centrifugal; Re-refine.
5, adopt the washing with alcohol purified product, be oven dry under 100 ℃ ± 10 ℃ conditions, sieve, make finished product N-acetyl D-amino glucose in temperature.
Example two:
1, get the raw materials ready:
Divide another name (amount) get chitin 700kg, 30% hydrochloric acid 4500kg, aceticanhydride 200kg, triethylamine 280kg, _ grease-removing agent (as sodium bicarbonate) 2kg.
2, hydrolysis reaction:
Chitin and 4200kg mixed in hydrochloric acid are added in the reactor, slowly heat up, make chitin transform dissolving under 55～60 ℃ of temperature condition, constantly stir, be warming up to little boiling again, back hydrolysis 2.5h ± 0.1h makes the D-glucosamine hydrochloride.
3, acylation reaction:
With 10kg hydrochloric acid is catalyzer, and D-glucosamine hydrochloride and aceticanhydride, triethylamine are carried out acylation reaction, and the acylation reaction temperature is controlled at 15～20 ℃, through centrifugal, obtains thick N-acetyl D-amino glucose.
4, refining:
Vacuum tightness is that 0.09MPa ± 0.005Mpa, temperature are under 50 ℃ ± 3 ℃ conditions, adds grease-removing agent and make with extra care in thick N-acetyl D-amino glucose; Centrifugal; Re-refine.
5, adopt the washing with alcohol purified product, be oven dry under 100 ℃ ± 10 ℃ conditions, sieve, make finished product N-acetyl D-amino glucose in temperature.
The performance index contrast table that every performance index of producing by above two kinds of methods of finished product N-acetyl D-amino glucose and U.S. Pacific Ocean biological products company limited produce is as follows:
| Index name | Unit | Product index with the inventive method production | The product index that U.S. Pacific Ocean biological products company limited produces |
| Content | ％ | 99～102 | 97～100 |
| Fusing point | ℃ | 196～205 | 195～204 |
| Specific rotation [a] 20 | 39～42 | 39～43 | |
| Muriate | ％ | ＜0.5 | ＜1 |
| PH value | 5.5～7.5 | 5.5～7.5 | |
| Moisture content | ％ | 0.5 | 0.5 |
| Combustionresidue | ％ | 0.1 | 0.1 |
| Heavy metal | ppm | ≤10 | ≤10 |
| Molysite | ppm | ≤10 | ≤10 |
| Arsenic salt | ppm | ≤10 | ≤10 |
| Outward appearance | White needle-like crystals | White needle-like crystals |
Correlation data from table as can be known, product quality indicator of the present invention reaches and surpasses the index request of U.S. Pacific Ocean biological products company limited product standard defined, can satisfy the requirement of market to quality product fully.
Claims (10)
1. the production method of N-acetyl D-amino glucose is characterized in that may further comprise the steps:
1) chitin and excessive hydrochloric acid are hydrolyzed reaction makes the D-glucosamine hydrochloride;
2) with D-glucosamine hydrochloride and aceticanhydride, triethylamine acylation reaction, get thick N-acetyl D-amino glucose through centrifuging and taking;
3) adding sodium bicarbonate in thick N-acetyl D-amino glucose makes with extra care;
4) adopt washing with alcohol, again drying, sieve, make finished product N-acetyl D-amino glucose.
2. according to the production method of the described N-acetyl D-amino glucose of claim 1, it is characterized in that in the step 1) that the weight ratio of chitin and hydrochloric acid is 1: 5～7.
3. according to the production method of the described N-acetyl D-amino glucose of claim 2, it is characterized in that in the step 1), adopt 35% hydrochloric acid, hydrolysis time is 1.5h ± 0.1h.
4. according to the production method of the described N-acetyl D-amino glucose of claim 2, it is characterized in that in the step 1), adopt 30% hydrochloric acid, hydrolysis time is 2.5h ± 0.1h.
5. according to claim 1 or 2 or the production method of 3 or 4 described N-acetyl D-amino glucoses, it is characterized in that in the step 1), in hydrolytic process, slowly heat up, under 55～60 ℃ of temperature condition, make chitin transform dissolving, stir, be warming up to little boiling again, back hydrolysis.
6. according to the production method of the described N-acetyl D-amino glucose of claim 1, it is characterized in that step 2) in, be catalyst for reaction with hydrochloric acid, the weight ratio of catalyzer hydrochloric acid and D-glucosamine hydrochloride is 1: 0.01～0.02.
7. according to the production method of claim 1 or 6 described N-acetyl D-amino glucoses, it is characterized in that step 2) in, the acylation reaction temperature is 15～20 ℃.
8. according to the production method of the described N-acetyl D-amino glucose of claim 1, it is characterized in that in the step 3), refining through twice.
9. according to the production method of claim 1 or 8 described N-acetyl D-amino glucoses, it is characterized in that in the step 3) that the vacuum tightness when refining is 0.09MPa ± 0.005MPa, temperature is 50 ℃ ± 3 ℃.
10. according to the production method of the described N-acetyl D-amino glucose of claim 1, it is characterized in that in the step 4) that bake out temperature is 90 ℃～110 ℃.
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| CNB200610040473XA CN100422198C (en) | 2006-05-17 | 2006-05-17 | Production process of N-acetyl D-amino glucose |
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| CNB200610040473XA CN100422198C (en) | 2006-05-17 | 2006-05-17 | Production process of N-acetyl D-amino glucose |
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| CN100422198C true CN100422198C (en) | 2008-10-01 |
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101830938B (en) * | 2010-05-19 | 2013-05-01 | 王松叶 | Preparation method of N-acetyl-D-glucosamine |
| CN102492001A (en) * | 2011-12-15 | 2012-06-13 | 石狮市华宝海洋生物化工有限公司 | Method for preparing N-acetyl-D-(+)-glucosamine |
| CN103509064A (en) * | 2012-06-18 | 2014-01-15 | 扬州明增生物科技有限公司 | N-acetyl-D-glucosamine production method |
| CN106008615B (en) * | 2016-06-01 | 2018-07-13 | 江苏澳新生物工程有限公司 | The method that chitin prepares 2-acetylamino-2-deoxy-D-glucose |
| CN110669082B (en) * | 2019-10-23 | 2020-11-03 | 山东润德生物科技有限公司 | Purification and separation method of N-acetyl-D-glucosamine |
| CN110684057A (en) * | 2019-11-22 | 2020-01-14 | 山东润德生物科技有限公司 | Production method of N-acetyl-D-glucosamine |
| CN111393489A (en) * | 2020-05-08 | 2020-07-10 | 马鞍山市天泰生物科技有限公司 | Purification and separation method of N-acetyl-D-glucosamine |
| CN115448963A (en) * | 2022-10-21 | 2022-12-09 | 扬州日兴生物科技股份有限公司 | Preparation method of N-acetyl-D-glucosamine |
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- 2006-05-17 CN CNB200610040473XA patent/CN100422198C/en active Active
Non-Patent Citations (4)
| Title |
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| N－乙酰氨基葡萄糖合成方法的改进. 乔岩等.化学试剂，第24卷第3期. 2002 |
| N－乙酰氨基葡萄糖合成方法的改进. 乔岩等.化学试剂，第24卷第3期. 2002 * |
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Address after: 225601 No. 58, Wuan Road, Yangzhou, Jiangsu, Gaoyou Patentee after: YANGZHOU RIXING BIO-TECH Co., LTD. Address before: 225601 No. 58, Wuan Road, Yangzhou, Jiangsu, Gaoyou Patentee before: Yangzhou Rixing Biological Chemical Products Co., Ltd. |