CN110590869A - Preparation method of N-acetylglucosamine - Google Patents
Preparation method of N-acetylglucosamine Download PDFInfo
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Abstract
The invention belongs to the field of pharmaceutical chemicals, and discloses a preparation method of N-acetylglucosamine. The preparation method of the N-acetylglucosamine comprises the following steps: dissolving chitin, glycine lactate hydrochloride and hexafluoroisopropanol to obtain a crude mother liquor, and filtering by using a microporous membrane filter to obtain a refined mother liquor; mixing the refined mother liquor with 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid to prepare degradation liquid; adding activated carbon into the degradation liquid for decolorization, and filtering; concentrating the filtrate, cooling, adding an organic solvent for crystallization, filtering to obtain a crude product of N-acetylglucosamine, soaking in absolute ethanol, stirring, filtering, and drying to obtain the N-acetylglucosamine. The N-acetylglucosamine prepared by the method has high yield, the purity of the obtained N-acetylglucosamine can reach more than 99.9 percent, the preparation method has simple process and lower cost, the used solvent can be recycled, and the method is environment-friendly, economic and suitable for large-scale popularization and application.
Description
Technical Field
The invention relates to the field of pharmaceutical chemicals, and particularly relates to a preparation method of N-acetylglucosamine.
Background
Aminosugars are commonly used as monosaccharide residues in complex oligosaccharides and polysaccharides, glucosamine being an amino derivative of the monosaccharide glucose, and N-acetylglucosamine being an acetylated derivative of glucosamine. As a novel biochemical medicine, N-acetylglucosamine is a composition unit of various polysaccharides in a living body, particularly has the highest exoskeleton content in crustaceans, is a medicament for clinically treating rheumatic and rheumatoid arthritis, can also be used as a food antioxidant, an infant food additive and a sweetener for diabetics, can also be used for clinically enhancing the function of a human immune system, inhibiting the overgrowth of cancer cells or fiber cells and playing a role in inhibiting and treating cancers and malignant tumors.
The existing preparation method of N-acetylglucosamine mainly comprises the steps of preparing N-acetylglucosamine by a microbial fermentation method, preparing N-acetylglucosamine by a chemical method and preparing N-acetylglucosamine by enzymolysis. The microbial fermentation method for preparing the N-acetylglucosamine needs to be subjected to microbial strain culture, then fermentation, separation and other technological processes, the whole technological process is complex, the operation is complex, the yield is very low, and the industrial production is not facilitated, the chemical method for producing the N-acetylglucosamine needs a large amount of toxic and harmful chemical reagents in the preparation process, not only chemical residues exist in the product of the N-acetylglucosamine, but also chemical pollution is not facilitated for environmental protection, accidents such as combustion, explosion and the like are easy to occur in the whole process, the N-acetylglucosamine is prepared by enzymolysis, the industrial cost needs to be increased no matter what kind of enzyme is needed, the yield is also very low, and the industrial production is not facilitated, and the three methods for preparing the N-acetylglucosamine have the problems of low yield and low product purity. In view of the above-mentioned drawbacks, it is necessary to design a method for preparing N-acetylglucosamine.
Disclosure of Invention
The invention aims to overcome the defects of the background technology and provides the preparation method of the N-acetylglucosamine, the method has simple process and lower cost, and the N-acetylglucosamine prepared by the method has higher yield and purity and good economic benefit and is suitable for large-scale popularization and application.
In order to achieve the purpose of the invention, the preparation method of the N-acetylglucosamine comprises the following steps:
(1) dissolving chitin, glycine lactate hydrochloride and hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor;
(2) mixing the refined mother liquor prepared in the step (1) with 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid to prepare degradation liquid;
(3) adding 0.5 to 1.0 mass percent of active carbon of chitin into the degradation liquid prepared in the step (2) for decolorization, and filtering;
(4) concentrating the filtrate obtained in the step (3), cooling, adding an organic solvent into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine;
(5) and (4) soaking the crude product prepared in the step (4) in absolute ethyl alcohol, stirring, filtering and drying to obtain the N-acetylglucosamine.
Preferably, the volume ratio of the glycine lactate hydrochloride to the hexafluoroisopropanol in the step (1) is 1-2: 1; more preferably, the mass-to-volume ratio of the chitin to the glycine lactate hydrochloride in the step (1) is 1: 1 to 2.
Further, the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid in the step (2) is 1: 1 to 2.
Further, the temperature of the mixed degradation reaction of the refined mother liquor and the 1-propylsulfonic acid group-3-methylimidazole hydrogen sulfate ionic liquid in the step (2) is 72-85 ℃.
Further, mixing the refined mother liquor in the step (2) with 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid, and then carrying out heat preservation reaction for 4-5 hours.
Further, the filtration in the step (3) is performed by a microporous filter or an ultramicropore filter.
Further, the filtrate concentration in the step (4) is to heat the filtrate to 75-95 ℃ under a vacuum condition, and concentrate the solution to a supersaturated state.
Further, the volume ratio of the concentrated solution to the organic solvent in the step (4) is 1: 2 to 3.
Further, the temperature reduction in the step (4) is to be carried out to 19-27 ℃.
Further, the organic solvent in step (4) is an alcohol or ketone solvent, such as ethanol, absolute ethanol, propanol or acetone.
Further, the mass ratio of the crude product to the absolute ethyl alcohol in the step (5) is 1: 2 to 3.
Devitrification, which refers to the precipitation of another phase when a substance is in a non-equilibrium state, is a crystalline form. In order to purify a substance by crystallization, conditions suitable for a reaction system, such as temperature, solvent and the like, need to be selected, and the invention discovers that according to the preparation method, refined N-acetylglucosamine with high yield, good crystal form and high purity can be obtained by concentrating an N-acetylglucosamine solution to a supersaturated state, cooling the solution to 19-27 ℃, adding an alcohol or ketone solvent, preferably an alcohol solvent, and crystallizing the solution, wherein the purity or the yield of the obtained N-acetylglucosamine is not as high as 19-27 ℃ when the temperature is reduced to below 19 or above 27 ℃.
By the method, the yield of the N-acetylglucosamine prepared by the preparation method is high, the purity of the obtained N-acetylglucosamine can reach more than 99.9%, the preparation method is simple in process and low in cost, the used solvent can be recycled, and the preparation method is environment-friendly, economical and suitable for large-scale popularization and application.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention. It is to be understood that the following description is only illustrative of the present invention and is not to be construed as limiting the present invention.
The terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or as a range of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when a range of "1 to 5" is disclosed, the described range should be interpreted to include the ranges "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.
Example 1
Dissolving 1kg chitin, 1.5L glycine lactate hydrochloride and 0.75L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 72 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 22 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, wherein the content of the high-purity N-acetylglucosamine is determined by an HPLC method, the yield is 85.9%, and the purity is 99.95%.
Example 2
Dissolving 1kg chitin, 1L glycine lactate hydrochloride and 1L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 80 ℃, preserving the temperature and reacting for 5 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 75 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 19 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, wherein the content of the high-purity N-acetylglucosamine is measured by an HPLC method, the yield is 83.5%, and the purity is 99.92%.
Example 3
Dissolving 1kg chitin, 2L glycine lactate hydrochloride and 1L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 85 ℃, preserving the temperature and reacting for 5 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 95 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 27 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, wherein the content of the high-purity N-acetylglucosamine is determined by an HPLC method, the yield is 85.6%, and the purity is 99.94%.
Example 4
Dissolving 1kg of chitin and 2.25L of hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 72 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 22 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, wherein the content of the high-purity N-acetylglucosamine is determined by an HPLC method, the yield is 85.9%, and the purity is 99.95%.
Example 5
Dissolving 1kg of chitin and 2.25L of lactic acid glycine hydrochloride in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 72 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 22 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, wherein the content of the high-purity N-acetylglucosamine is determined by an HPLC method, the yield is 85.9%, and the purity is 99.95%.
Example 6
Dissolving 1kg chitin, 1.5L lysine hydrochloride and 0.75L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 72 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 22 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, and measuring the content of the high-purity N-acetylglucosamine by an HPLC method, wherein the yield is 76.1% and the purity is 99.83%.
Example 7
Dissolving 1kg chitin, 1.5L glycine lactate hydrochloride and 0.75L hexafluoroacetone in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 72 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 22 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, and measuring the content of the high-purity N-acetylglucosamine by an HPLC method, wherein the yield is 75.0% and the purity is 99.76%.
Example 8
Dissolving 1kg chitin, 1.5L glycine lactate hydrochloride and 0.75L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-H-3-methylimidazole hydrogen sulfate ionic liquid at 72 ℃, preserving heat and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-H-3-methylimidazole hydrogen sulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 22 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, wherein the content of the high-purity N-acetylglucosamine is determined by an HPLC method, the yield is 73.4%, and the purity is 99.93%.
Example 9
Dissolving 1kg chitin, 1.5L glycine lactate hydrochloride and 0.75L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 70 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 22 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, wherein the content of the high-purity N-acetylglucosamine is determined by an HPLC method, the yield is 80.3%, and the purity is 99.92%.
Example 10
Dissolving 1kg chitin, 1.5L glycine lactate hydrochloride and 0.75L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 65 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 22 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, and measuring the content of the high-purity N-acetylglucosamine by an HPLC method, wherein the yield is 74.2% and the purity is 99.93%.
Example 11
Dissolving 1kg chitin, 1.5L glycine lactate hydrochloride and 0.75L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 90 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 22 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, and measuring the content of the high-purity N-acetylglucosamine by an HPLC method, wherein the yield is 71.4% and the purity is 97.32%.
Example 12
Dissolving 1kg chitin, 1.5L glycine lactate hydrochloride and 0.75L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 72 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 15 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, wherein the content of the high-purity N-acetylglucosamine is determined by an HPLC method, the yield is 75.5%, and the purity is 99.83%.
Example 13
Dissolving 1kg chitin, 1.5L glycine lactate hydrochloride and 0.75L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 72 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 10 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, and measuring the content of the high-purity N-acetylglucosamine by an HPLC method, wherein the yield is 72.7 percent and the purity is 99.80 percent.
Example 14
Dissolving 1kg chitin, 1.5L glycine lactate hydrochloride and 0.75L hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor; mixing the prepared refined mother liquor and 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid at 72 ℃, preserving the temperature and reacting for 4 hours to prepare degradation liquid, wherein the volume ratio of the refined mother liquor to the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid is 1: 1.5; adding 0.5-1.0 mass percent of activated carbon of chitin into the prepared degradation liquid for decolorization, filtering through a microporous filter or an ultramicropore filter, heating the obtained filtrate to 80 ℃ under a vacuum condition, concentrating to a supersaturated state, cooling to 30 ℃, adding absolute ethyl alcohol into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine; soaking the obtained crude product in absolute ethyl alcohol with the mass 2-3 times that of the crude product, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine, and measuring the content of the high-purity N-acetylglucosamine by an HPLC method, wherein the yield is 76.6% and the purity is 99.90%.
It will be appreciated by those skilled in the art that the foregoing is merely exemplary of the development process of the invention and is not intended to limit the invention, which in the spirit and scope of the invention comprises all modifications, equivalents and improvements falling within the spirit and scope of the invention.
Claims (10)
1. A preparation method of N-acetylglucosamine is characterized by comprising the following steps:
(1) dissolving chitin, glycine lactate hydrochloride and hexafluoroisopropanol in an ultrasonic stirring tank to obtain a crude mother liquor, and continuously pumping into a microporous membrane filter by using a diaphragm pump for filtering to obtain a refined mother liquor;
(2) mixing the refined mother liquor prepared in the step (1) with 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid to prepare degradation liquid;
(3) adding 0.5 to 1.0 mass percent of active carbon of chitin into the degradation liquid prepared in the step (2) for decolorization, and filtering;
(4) concentrating the filtrate obtained in the step (3), cooling, adding an organic solvent into the concentrated solution for crystallization, and performing centrifugal filtration to obtain a crude product of the N-acetylglucosamine;
(5) and (4) soaking the crude product prepared in the step (4) in absolute ethyl alcohol, stirring, filtering and drying to obtain the high-purity N-acetylglucosamine.
2. The method for producing N-acetylglucosamine according to claim 1, wherein the volume ratio of lactic acid glycine hydrochloride to hexafluoroisopropanol in the step (1) is 1 to 2: 1; preferably, the mass-to-volume ratio of the chitin to the glycine lactate hydrochloride in the step (1) is 1: 1 to 2.
3. The method for preparing N-acetylglucosamine according to claim 1, wherein the volume ratio of the refined mother liquor to the ionic liquid of 1-propylsulindyl-3-methylimidazole hydrogen sulfate in the step (2) is 1: 1-2; preferably, the temperature of the mixed degradation reaction of the refined mother liquor and the 1-propylsulfonic acid group-3-methylimidazole hydrogen sulfate ionic liquid in the step (2) is 72-85 ℃.
4. The method for preparing N-acetylglucosamine according to claim 1, wherein the refined mother liquor obtained in step (2) is mixed with 1-propylsulfo-3-methylimidazolium hydrogen sulfate ionic liquid and then subjected to a reaction under a heat preservation condition for 4-5 hours.
5. The process according to claim 1, wherein the filtration in the step (3) is carried out by a microporous filter or an ultramicropore filter.
6. The method for producing N-acetylglucosamine according to claim 1, wherein the concentration of the filtrate in the step (4) is carried out by heating the filtrate to 75 to 95 ℃ under vacuum to concentrate the solution to a supersaturated state.
7. The method for preparing N-acetylglucosamine according to claim 1, wherein the volume ratio of the concentrated solution to the organic solvent in step (4) is 1: 2 to 3.
8. The method for preparing N-acetylglucosamine according to claim 1, wherein the temperature reduction in the step (4) is to be 19-27 ℃.
9. The method for preparing N-acetylglucosamine according to claim 1, wherein the organic solvent in step (4) is an alcohol or ketone solvent, such as ethanol, absolute ethanol, propanol or acetone.
10. The method for preparing N-acetylglucosamine according to claim 1, wherein the mass ratio of the crude product to the absolute ethyl alcohol in the step (5) is 1: 2 to 3.
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