CN112522339B - Method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine by using chitin - Google Patents
Method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine by using chitin Download PDFInfo
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- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
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- C—CHEMISTRY; METALLURGY
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention relates to preparation of chemicals, in particular to a method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine by utilizing chitin, which is a nitrogen-containing platform compound with high added value, can be used for various nitrogen-containing fine chemical synthesis, and has great application value. The preparation method comprises the steps of degrading chitin into N-acetyl-D-glucosamine serving as a monomer by using chitinase, taking the chitinase as a starting substrate, taking N, N-dimethylacetamide as a reaction solvent, and performing cyclodehydration under the action of catalysts such as ammonium thiocyanate and structural analogues thereof and a small amount of metal salt serving as auxiliary catalysts to form 3A5AF. The method has the advantages of simple reaction steps, low catalyst cost, convenient operation, high product yield and better industrialized prospect.
Description
Technical Field
The invention belongs to the field of biomass conversion, and particularly relates to a method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine by using chitin.
Background
The nitrogenous compound is an important chemical product, has important application value in the chemical industry field, the medical field and the material field, is generally synthesized from nonrenewable fossil resources such as coal, petroleum and the like, and needs to be additionally added with amino donors, so that the energy consumption is high, the conversion rate is low and the economic benefit is poor.
Chitin(C 8 H 13 O 5 N) n The polymer which is also called chitin and is combined by NAG through beta-1, 4 glycosidic bond is extremely widely distributed in nature, mainly exists in exoskeletons such as shrimps, crabs, insects and the like, has the content which is inferior to cellulose, and is the second largest renewable resource in the world. The chitin structure contains nitrogen element, and is an excellent substrate for synthesizing nitrogen-containing chemicals. Therefore, the direct conversion of chitin into high added value nitrogen-containing compounds not only brings great economic benefits to the modern society, but also has important significance for waste treatment and environmental protection.
The 3-acetamido-5-acetylfuran (3A 5 AF) is a nitrogen-containing platform compound with high added value, which can be obtained from chitin, and has great application prospect and research value in the field of synthesis of nitrogen-containing fine chemicals. For example, 3A5AF is an important component of several bioactive macromolecular compounds, including the anticancer agents Proximin A, alkaloids hyrtioseragamine A and B, and pyrroosine, among others. In addition, can also be used for synthesizing furandiamine chemicals.
The synthesis of 3A5AF using chitin and its monomeric NAG as substrates has been reported. For example, yan et al can produce 3A5AF using chitin as a substrate in a yield of 7.5%. However, when chitin was used as a substrate, the yields of 3A5AF were low, at maximum 18%. The degradation product NAG of chitin is taken as a substrate, so that the yield can be effectively improved. Francih et al reported pyrolysis of NAG at high temperatures to give the nitrogen-containing compound 3A5AF. Drover et al report that at 180℃at boric acid [ B (OH) 3 ]NAG in the ionic liquid was converted to 3A5AF in 60% yield. Omari et al at 220℃in B (OH) 3 And NaCl, NAG was converted to 3A5AF by microwave irradiation in 58% yield. However, ionic liquids are often used as catalysts in the reported studies, which are expensive and the substrates result in high production costs.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a method for preparing 3-acetamido-5-acetylfuran (3A 5 AF) by degrading N-acetyl-D-glucosamine (NAG) by utilizing chitin, which utilizes a green biological enzyme method to degrade renewable biomass chitin into N-acetyl-D-glucosamine by utilizing chitinase, and further utilizes a chemical catalysis method to synthesize NAG into 3A5AF with high added value under the condition that N, N-dimethylacetamide is taken as a solvent, ammonium thiocyanate and structural analogues thereof are taken as a catalyst and metal salt is taken as a cocatalyst.
In order to solve the technical problems, the invention adopts the following technical scheme:
a method for preparing 3-acetamido-5-acetyl furan by degrading N-acetyl-D-glucosamine by using chitin, comprising the following steps:
step 1, adding chitinase, phosphate buffer solution and metal ions into chitin, carrying out enzymolysis at a temperature of 30-50 ℃ and a pH value of 6-8 for 24-120 h, separating supernatant after enzymolysis, and carrying out ion exchange resin adsorption, vacuum concentration and freeze drying to obtain NAG crystals;
and 2, dissolving NAG, a catalyst and a metal salt cocatalyst in a pressure-resistant pipe, adding 5mL of solvent for dissolution, heating for reaction for 5-240 min, filtering, taking filtrate, adding equal volume of water into the filtrate for mixing, extracting with ethyl acetate for three times, combining extract liquid after extraction, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, and filtering and drying to obtain transparent needle-like 3A5AF crystals with purity higher than 99.5%.
As an improvement, the chitinase is one or two of chitinase, chitinase and N-acetaminosaccharase.
As an improvement, the chitin is used in an amount of 0.025g-1g, the NAG is used in an amount of 0.025g-1g, the mass of the catalyst is 0.1-5 times that of the substrate NAG, and the mass of the cocatalyst is 0.1-5 times that of the substrate NAG.
As an improvement, the catalyst is one or a mixture of any two of ammonium thiocyanate, thiourea, potassium thiocyanate, thiobenzamide, thioacetamide or thiosemicarbazide.
As an improvement, the solvent in the step 2 is one or a mixture of any two of N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide or ethanol, and the using amount of the solvent is 1-100 mL.
As an improvement, the promoter is one or a mixture of two of boric acid, sodium chloride, potassium chloride, lithium chloride, ammonium chloride, zinc chloride, aluminum chloride hexahydrate, cobalt chloride hexahydrate, magnesium chloride hexahydrate, calcium chloride dihydrate, barium chloride dihydrate, ferric chloride hexahydrate, manganese chloride, hydrogen chloride and 1-butyl-3-methylimidazole chloride.
As an improvement, the reaction temperature in the step 2 is 120-200 ℃.
The beneficial effects are that:
compared with the prior art, the method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine by using chitin, which is disclosed by the invention, prepares 3A5AF by using renewable biomass resource chitin monomer NAG as a raw material, so that the research on effective utilization of biomass is widened; the method uses the cheap and easily available ammonium thiocyanate as the catalyst, greatly reduces the production cost of the 3A5AF and is beneficial to the industrialized production of the 3A5AF.
Drawings
FIG. 1 is a liquid phase test result of the 3A5AF standard;
FIG. 2 shows the liquid phase detection results after NAG was reacted under a catalyst for 45min.
Detailed Description
The following examples are presented to aid in a further understanding of the invention.
Example 1
Chitin was converted using chitinase in a 200mL reaction system (chitin powder 40 g/L, chitinase 1.3U/mL, N-acetaminophenosidase 1.35U/mL, caCl) 2 15 mM, phosphate buffer pH 8), at 37℃and 200rpm, the reaction was stirred for 36 h, and after the completion of the reaction, the supernatant was separated, adsorbed by an ion exchange resin, concentrated in vacuo, and lyophilized to give NAG crystals.
Then, 100mg NAG and 50mg ammonium thiocyanate (catalyst) were put in a 50mL pressure-resistant tube, 5mL N, N-dimethylacetamide (solvent) was added thereto, and the mixture was heated and stirred under pressure at 180℃for 45 minutes in a magnetic stirring heater. After the reaction is cooled to room temperature, adding pure water with equal volume for mixing, extracting for multiple times by using ethyl acetate, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, filtering and drying to obtain high-purity (99.5%) transparent needle-like 3A5AF crystals. The concentration of 3A5AF in the reaction liquid was found to be 4.43g/L, and the molar conversion was found to be 29.31%.
Example 2
Chitin is converted by chitinase, wherein the reaction system (40. 40 g/L chitin powder, 1.3U/mL chitinase, 1.35U/mL N-acetaminophenosidase, caCl) 2 15 mM, pH 8 phosphate buffer) 200mL was stirred at 37℃and 200rpm for reaction 36 h, and after the completion of the reaction, the supernatant was separated, adsorbed by an ion exchange resin, concentrated in vacuo, and lyophilized to give NAG crystals.
Then, 100mg NAG and 50mg ammonium thiocyanate were put into a 50mL pressure-resistant tube, 5mL dimethyl sulfoxide (solvent) was added thereto, and the mixture was heated and stirred under pressure at 180℃in a magnetic stirring heater for 45 minutes. After the reaction is cooled to room temperature, adding pure water with equal volume for mixing, extracting for multiple times by using ethyl acetate, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, filtering and drying to obtain high-purity (99.5%) transparent needle-like 3A5AF crystals. The concentration of 3A5AF in the reaction liquid was 0.15g/L, and the molar conversion was 0.99%.
Example 3
Chitin is converted by chitinase, wherein the reaction system (40. 40 g/L chitin powder, 1.3U/mL chitinase, 1.35U/mL N-acetaminophenosidase, caCl) 2 15 mM, pH 8 phosphate buffer) 200mL at 37℃and 200rpm, 36 h, separating the supernatant after the reaction, adsorbing with ion exchange resin, vacuum concentrating, and freeze drying to obtain NAG crystals.
Then, 100mg NAG and 50mg ammonium thiocyanate were put into a 50mL pressure-resistant tube, 5mL N-methylpyrrolidone (solvent) was added thereto, and the mixture was heated and stirred under pressure in a magnetic stirring heater at 180℃for 45 minutes. After the reaction is cooled to room temperature, adding pure water with equal volume for mixing, extracting for multiple times by using ethyl acetate, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, filtering and drying to obtain high-purity (99.5%) transparent needle-like 3A5AF crystals. The concentration of 3A5AF in the reaction liquid was 1.00g/L, and the molar conversion was 6.60%.
Example 4
Chitin is converted by chitinase, wherein the reaction system (40. 40 g/L chitin powder, 1.3U/mL chitinase, 1.35U/mL N-acetaminophenosidase, caCl) 2 15 mM, pH 8 phosphate buffer) 200mL at 37℃and 200rpm, 36 h, separating the supernatant after the reaction, adsorbing with ion exchange resin, vacuum concentrating, and freeze drying to obtain NAG crystals.
Then, 100mg NAG, 50mg ammonium thiocyanate and 0.0132g sodium chloride were put into a 50mL pressure-resistant tube, 5mL of N, N-dimethylacetamide was added thereto, and the mixture was heated and stirred for 45 minutes at 180℃in a magnetic stirring heater under pressure. After the reaction is cooled to room temperature, adding pure water with equal volume for mixing, extracting for multiple times by using ethyl acetate, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, filtering and drying to obtain high-purity (99.5%) transparent needle-like 3A5AF crystals. The concentration of 3A5AF in the reaction liquid was 5.66g/L, and the molar conversion rate was 37.43%.
Example 5
Chitin is converted by chitinase, wherein the reaction system (40. 40 g/L chitin powder, 1.3U/mL chitinase, 1.35U/mL N-acetaminophenosidase, caCl) 2 15 mM, pH 8 phosphate buffer) 200mL at 37℃and 200rpm, 36 h, separating the supernatant after the reaction, adsorbing with ion exchange resin, vacuum concentrating, and freeze drying to obtain NAG crystals.
Then, 100mg NAG, 50mg ammonium thiocyanate and 0.067g calcium chloride dihydrate were taken, 5mL N, N-dimethylacetamide was added to a 50mL pressure-resistant tube, and heated and stirred in a magnetic stirring heater at 180℃for 45min under pressure. After the reaction is cooled to room temperature, adding pure water with equal volume for mixing, extracting for multiple times by using ethyl acetate, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, filtering and drying to obtain high-purity (99.5%) transparent needle-like 3A5AF crystals. The concentration of 3A5AF in the reaction liquid was 6.53g/L, molar conversion rate, 43.24%.
Example 6
Chitin is converted by chitinase, wherein the reaction system (40. 40 g/L chitin powder, 1.3U/mL chitinase, 1.35U/mL N-acetaminophenosidase, caCl) 2 15 mM, pH 8 phosphate buffer) 200mL at 37℃and 200rpm, 36 h, separating the supernatant after the reaction, adsorbing with ion exchange resin, vacuum concentrating, and freeze drying to obtain NAG crystals.
Then, 100mg NAG, 50mg ammonium thiocyanate and 0.034 potassium chloride were taken, 5mL N, N-dimethylacetamide was added to a 50mL pressure-resistant tube, and the mixture was heated and stirred at 180℃for 45 minutes under pressure in a magnetic stirring heater. After the reaction is cooled to room temperature, adding pure water with equal volume for mixing, extracting for multiple times by using ethyl acetate, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, filtering and drying to obtain high-purity (99.5%) transparent needle-like 3A5AF crystals. The concentration of 3A5AF in the reaction liquid was 5.38g/L, and the molar conversion rate was 35.58%.
Example 7
Chitin is converted by chitinase, wherein the reaction system (40. 40 g/L chitin powder, 1.3U/mL chitinase, 1.35U/mL N-acetaminophenosidase, caCl) 2 15 mM, pH 8 phosphate buffer) 200mL at 37℃and 200rpm, 36 h, separating the supernatant after the reaction, adsorbing with ion exchange resin, vacuum concentrating, and freeze drying to obtain NAG crystals.
Then, 100mg NAG, 50mg ammonium thiocyanate and 0.067g calcium chloride dihydrate were put into a 50mL pressure-resistant tube, 5mL N, N-dimethylacetamide was added, and the mixture was heated and stirred for 5 minutes at 180℃in a magnetic stirring heater under pressure. After the reaction is cooled to room temperature, adding pure water with equal volume for mixing, extracting for multiple times by using ethyl acetate, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, filtering and drying to obtain high-purity (99.5%) transparent needle-like 3A5AF crystals. The concentration of 3A5AF in the reaction liquid was 7.28g/L, and the molar conversion was 48.14%.
Example 8
Chitin is converted by chitinase, wherein the reaction system (40. 40 g/L chitin powder, 1.3U/mL chitinase, 1.35U/mL N-acetaminophenosidase, caCl) 2 15 mM, pH 8 phosphate buffer) 200mL at 37℃and 200rpm, 36 h, separating the supernatant after the reaction, adsorbing with ion exchange resin, vacuum concentrating, and freeze drying to obtain NAG crystals.
Then, 100mg NAG, 50mg ammonium thiocyanate and 0.067g calcium chloride dihydrate were put into a 50mL pressure-resistant tube, 5mL N, N-dimethylacetamide was added, and the mixture was heated and stirred for 30 minutes at 180℃in a magnetic stirring heater under pressure. After the reaction is cooled to room temperature, adding pure water with equal volume for mixing, extracting for multiple times by using ethyl acetate, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, filtering and drying to obtain high-purity (99.5%) transparent needle-like 3A5AF crystals. The concentration of 3A5AF in the reaction liquid was 7.45g/L, and the molar conversion rate was 49.30%.
Example 9
Chitin is converted by chitinase, wherein the reaction system (40. 40 g/L chitin powder, 1.3U/mL chitinase, 1.35U/mL N-acetaminophenosidase, caCl) 2 15 mM, pH 8 phosphate buffer) 200mL at 37℃and 200rpm, 36 h, separating the supernatant after the reaction, adsorbing with ion exchange resin, vacuum concentrating, and freeze drying to obtain NAG crystals.
Then, 100mg NAG, 50mg ammonium thiocyanate and 0.067g calcium chloride dihydrate were put into a 50mL pressure-resistant tube, 5mL N, N-dimethylacetamide was added, and the mixture was heated and stirred for 120min at 180℃in a magnetic stirring heater under pressure. After the reaction is cooled to room temperature, adding pure water with equal volume for mixing, extracting for multiple times by using ethyl acetate, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, filtering and drying to obtain high-purity (99.5%) transparent needle-like 3A5AF crystals. The concentration of 3A5AF in the reaction liquid was found to be 6.76g/L, and the molar conversion was found to be 44.71%.
Example 10
Chitin is converted by chitinase, wherein the reaction system (40. 40 g/L chitin powder, 1.3U/mL chitinase, 1.35U/mL N-acetaminophenosidase, caCl) 2 15 mM, pH 8 phosphate buffer) 200mL at 37℃and 200rpm, 36 h, separating the supernatant after the reaction, adsorbing with ion exchange resin, vacuum concentrating, and freeze drying to obtain NAG crystals.
150mg of NAG, 50mg of ammonium thiocyanate and 0.075g of calcium chloride dihydrate are taken, 10mL of N, N-dimethylacetamide is added into a 50mL pressure-resistant tube, and the mixture is heated and stirred for 25min at 180 ℃ in a magnetic stirring heater under pressure. After the reaction is cooled to room temperature, adding pure water with equal volume for mixing, extracting for multiple times by using ethyl acetate, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolution, dropwise adding into pre-cooled deionized water for crystallization, filtering and drying to obtain high-purity (99.5%) transparent needle-like 3A5AF crystals. The concentration of 3A5AF in the reaction liquid was 8.56g/L, and the molar conversion rate was 56.66%.
Example 11
The liquid phase was conducted in the same manner as in example 1 except that the NAG reaction temperature was changed to 160℃and the concentration of 3A5AF in the reaction liquid was 1.20g/L, whereby the molar conversion was 7.92%.
Example 12
The liquid phase was conducted in the same manner as in example 1 except that the NAG reaction temperature was changed to 170. DegreeCin 3.12g/L, and the molar conversion was 20.67%.
Example 13
The liquid phase was conducted in the same manner as in example 1 except that the NAG reaction temperature was changed to 190℃and the concentration of 3A5AF in the reaction liquid was 4.20g/L, whereby the molar conversion was 27.81%.
Example 14
The concentration of 3A5AF in the reaction liquid was found to be 4.18g/L as measured in the liquid phase in the same manner as in example 1 except that the NAG reaction catalyst was changed to thiourea, and the molar conversion was 27.69%.
Comparative example 1
In the patent CN111072602A, amino acid ionic liquid is used as a catalyst to catalyze N-acetamido glucose into 3-acetamido-5-acetylfuran, and the catalyst has the advantages that the raw materials of the catalyst are cheap and easy to obtain, the highest conversion rate can reach 52.61%, the reaction temperature is as high as 200 ℃, and only 3A5AF crude products are finally obtained. The catalyst ammonium thiocyanate is used as a catalyst, the optimal yield can be up to 56.66% at 180 ℃, the cost of the catalyst ammonium thiocyanate is lower than that of the amino acid ionic liquid, the process of preparing the ionic liquid is avoided, and the reaction process is simplified. Meanwhile, the patent provides a crystallization method for obtaining the high-purity 3A5AF crystal, which is favorable for obtaining the high-purity 3A5AF product.
The invention directly starts from chitin, and firstly, the chitin is degraded into NAG by using a green biological enzyme method, and on the basis, ammonium thiocyanate and structural analogues thereof with low price are used as catalysts, so that the chitin can be finally and efficiently converted into platform chemical 3A5AF which can be used for chemical production.
While the foregoing is directed to embodiments of the present invention, other and further details of the invention may be had by the present invention, it should be understood that the foregoing description is merely illustrative of the present invention and that no limitations are intended to the scope of the invention, except insofar as modifications, equivalents, improvements or modifications are within the spirit and principles of the invention.
Claims (3)
1. A method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine by using chitin, which is characterized by comprising the following steps:
step 1, adding chitinase, phosphate buffer solution and metal ions into chitin, performing enzymolysis at 30-50deg.C and pH of 6-8 for 24-120 h, separating supernatant after enzymolysis, adsorbing with ion exchange resin, vacuum concentrating, and freeze drying to obtain NAG crystal, whereinThe metal ion is CaCl 2 15 mM；
Step 2, 150mg of NAG, 50mg of ammonium thiocyanate serving as a catalyst and 0.075g of calcium chloride dihydrate serving as a metal salt cocatalyst are taken and placed in a pressure-resistant tube, 10mL of N, N-dimethylacetamide serving as a solvent is added for dissolution, heating reaction is carried out at 180 ℃ for 25min, filtering is carried out after the reaction is finished, filtrate is taken, equal volume of water is added into the filtrate for mixing, ethyl acetate is used for extraction, extraction is carried out three times, extraction liquid is combined, the concentration is carried out under reduced pressure to obtain a solid crude product containing 3A5AF, 1mL of methanol is added for redissolution, the mixture is dropwise added into pre-cooled deionized water for crystallization, and the transparent needle-like 3A5AF crystals with the purity higher than 99.5% are obtained after filtration and drying.
2. The method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine by using chitin according to claim 1, wherein the chitinase is one or two of chitinase, chitinase exoenzyme and N-acetaminosaccharase.
3. The method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine by using chitin according to claim 1, wherein the chitin is used in an amount of 0.025g-1g.
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