CN107759541A - A kind of production method of 5 hydroxymethylfurfurals of the cellulose solution based on enzymolysis - Google Patents
A kind of production method of 5 hydroxymethylfurfurals of the cellulose solution based on enzymolysis Download PDFInfo
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- CN107759541A CN107759541A CN201711114525.8A CN201711114525A CN107759541A CN 107759541 A CN107759541 A CN 107759541A CN 201711114525 A CN201711114525 A CN 201711114525A CN 107759541 A CN107759541 A CN 107759541A
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- cellulose solution
- cellulose
- enzymolysis
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- hydroxymethyl furfural
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
Abstract
The present invention provides a kind of production method of 5 hydroxymethylfurfurals of the cellulose solution based on enzymolysis, comprises the following steps：After cellulose after crushing is soaked in alkali lye into fully infiltration, Ultrasonic Pulverization, it is 1 to add mass ratio:1 1.5 acid cellulose enzyme and glucose oxidase mixing ferment treatment, filters off the cellulose solution except residue, digested；Partial digestion is sodium gluconate in the cellulose solution of the enzymolysis, then by the cellulose solution of enzymolysis is raw material, to load SO4 2‑/In2O3The attapulgite of solid acid is catalyst, the irradiation reaction under microwave, obtains 5 hydroxymethylfurfurals.Acid cellulose enzyme is carried out to cellulose solution in advance for the production method of 5 hydroxymethylfurfurals of the invention and glucose oxidase mixed enzyme digests, with reference to microwave heating response, obtain 5 hydroxymethylfurfurals transitory efficient, good yield is can obtain in the short time of 5 hydroxymethylfurfurals, there is good application prospect.
Description
Technical field
The invention belongs to medicinal chemistry art, and in particular to a kind of 5 hydroxymethyl furfural of the cellulose solution based on enzymolysis
Production method.
Background technology
5 hydroxymethyl furfural is also known as 5-hydroxymethyl-furfural, HMF 5 hydroxymethyl 2 furaldehyde, 5-Hydroxymethylfurfural, 5-
Hydroxymethylfurans formaldehyde, it is acicular crystal, dark yellow liquid or powder, Flos Chrysanthemi taste, there is hygroscopicity, easily liquefaction, needs lucifuge
It is sealed.5 hydroxymethyl furfural is generated by hexose or the dehydration of the polysaccharide carbohydrate containing hexose structure, containing active in molecule
Group furan nucleus and aldehyde radical, can by being hydrogenated with, being esterified, polymerizeing, halogenation, hydrolysis, oxidative dehydrogenation and other chemical reactive synthesis
Multiple compounds and novel high polymer material, it is important medicine intermediate.
The raw material of 5 hydroxymethyl furfural can be the hexoses such as fructose, glucose, can also be the carbon water such as oligosaccharide, polysaccharide
Compound, also there are some with carbohydrate and abandoned biomass such as tapioca starch, bamboo shoot shell, discarded orange peel and Fructus Corni etc..
The method that cellulose base sulfonic acid catalyst catalysis fructose disclosed in Chinese patent CN 103694203B prepares 5 hydroxymethyl furfural,
Cellulose is added into isopropanol water in the mixed solvent, the acetone soln of alkali lye and Isosorbide-5-Nitrae-butane sultone is added dropwise, finally pours into first
Alcohol, filtering vacuum are dried, and obtain the cellulose sulfonic acid catalyst that Isosorbide-5-Nitrae-butane sultone is sulfonic acid source, then using isopropanol to be molten
Agent, fructose are raw material, remove solvent after hydro-thermal reaction, obtain 5 hydroxymethyl furfural and fructose.This method is using biomass as catalysis
Agent carrier, area load have the acid and alkaline group of catalytic action, make the active high, Stability Analysis of Structures of catalyst and cost cheap
Advantage.The method of the biomass production hydroxymethylfurfural of a kind of containing cellulose disclosed in Chinese patent CN 101948452B, by sulphur
Acid, phosphoric acid, hydrochloric acid, benzene sulfonic acid, benzoic acid, acetic acid, maleic acid, acid macroreticular resin, acidic molecular sieve, sulfuric acid load titanium dioxide
Silicon solid acid, sulfuric acid Supported alumina solid acid or chlorination are mixed to form reaction solution every as catalyst with zinc oxide and water,
Again using the biomass of dry containing cellulose as raw material, after heating response, extraction obtains 5 hydroxymethyl furfural, wherein containing cellulose
Biomass material be straw, rice straw, cornstalk, bagasse, corncob, wood chip, rice husk, wheat bran or cotton seed hulls.By above-mentioned
Prior art understands that cellulose biomass can be used in 5- methylol chaffs as raw material or as the carrier of catalyst
In the preparation of aldehyde.Cellulose is renewable biomass resources most abundant on the earth, is form plant skeleton and cell main
Composition, but cellulose is depolymerized to small molecule that monose difficulty is very big, this is also from cellulose or lignocellulose-like biomass
It is directly translated into the technological difficulties of 5 hydroxymethyl furfural.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of 5 hydroxymethyl furfural of the cellulose solution based on enzymolysis
Production method, by cellulose solution after alkali lye pulverization process, then through cellulase and glucose oxidase mixed enzyme enzymolysis make
Cellulase hydrolysis is sodium gluconate, then using the cellulase solution of enzymolysis as raw material, to load SO4 2-/In2O3Solid acid it is recessed
Convex rod soil is catalyst, the irradiation reaction under microwave, obtains 5 hydroxymethyl furfural.5 hydroxymethyl furfural method prepared by the present invention
Efficiency high, yield is high in the short time, has good application prospect.
In order to solve the above technical problems, the technical scheme is that：
A kind of production method of the 5 hydroxymethyl furfural of the cellulose solution based on enzymolysis, comprises the following steps：
(1) after the cellulose after crushing being soaked in alkali lye into fully infiltration, Ultrasonic Pulverization, it is 1 to add mass ratio:1-
1.5 acid cellulose enzyme and glucose oxidase mixing ferment treatment, filters off the cellulose solution except residue, digested；
(2) it is raw material by the cellulose solution of enzymolysis, to load SO4 2-/In2O3The attapulgite of solid acid is catalyst,
The irradiation reaction under microwave, obtains 5 hydroxymethyl furfural.
As the preferred of above-mentioned technical proposal, in the step (1), the raw material of cellulose is cotton fiber or wooden fibre
Dimension.
As the preferred of above-mentioned technical proposal, in the step (1), the size of the cellulose after crushing is less than 5mm.
As the preferred of above-mentioned technical proposal, in the step (1), the power of Ultrasonic Pulverization is 300-500W, and the time is
10-30min。
As the preferred of above-mentioned technical proposal, in the step (1), the enzyme activity of mixed enzyme is 15000-20000U/g.
As the preferred of above-mentioned technical proposal, in the step (1), the temperature of enzymolysis is 40-50 DEG C, time 30-
60min。
As the preferred of above-mentioned technical proposal, in the step (1), sodium gluconate contains in the cellulose solution of enzymolysis
Amount is not less than 20wt%.
As the preferred of above-mentioned technical proposal, in the step (2), the temperature of irradiation reaction is 160-200 DEG C under microwave,
Time is 10-30min.
As the preferred of above-mentioned technical proposal, in the step (2), the dosage of catalyst accounts for the gross mass of overall reaction system
2-5wt%.
As the preferred of above-mentioned technical proposal, in the step (2), the yield of 5 hydroxymethyl furfural is not less than 70%.
Compared with prior art, the invention has the advantages that：
The production method of the 5 hydroxymethyl furfural of cellulose solution based on enzymolysis prepared by the present invention, in order to solve fiber
Element is difficult to be depolymerized to small molecule monose, and first cellulose is digested through cellulase and glucose oxidase mixed enzyme, makes cellulose
Partial digestion is sodium gluconate, reduces the difficulty of catalyst, improves reaction efficiency, then the cellulase solution with enzymolysis
For raw material, to load SO4 2-/In2O3The attapulgite of solid acid is catalyst, the irradiation reaction under microwave, obtains 5- methylols
Furfural.
Catalyst is diphasic system in 5 hydroxymethyl furfural method prepared by the present invention, and attapulgite has larger ratio table
Face is tied and heat endurance, also with certain short message, the SO of load4 2-/In2O3The catalysis that solid acid further improves catalyst is lived
Property, solving the problems, such as the cellulase solution of enzymolysis, to be converted into fructose difficulty low, promotes sodium gluconate isomery and fructose to be dehydrated,
And not etching apparatus, it is green safe, therefore the efficiency high of the preparation method of the present invention, and yield is high in the short time, has fine
Application prospect.
Embodiment
The present invention is described in detail below in conjunction with specific embodiment, herein illustrative examples and explanation of the invention
For explaining the present invention, but it is not as a limitation of the invention.
Embodiment 1：
(1) it is 1 according to the solid-to-liquid ratio of cellulose and alkali lye:50, by cotton fiber or wood fibre of the size less than 5mm
After cellulose is soaked in alkali lye fully infiltration, the Ultrasonic Pulverization 10min under 300W power, it is 1 to add mass ratio:1 acid is fine
Plain enzyme and glucose oxidase (enzyme activity 15000U/g) mixed enzyme is tieed up, 30min is handled at 40 DEG C, filters off except residue,
The cellulose solution digested, wherein the content of sodium gluconate is 25wt% in the cellulose solution digested.
(2) it is raw material by the cellulose solution of enzymolysis, to load SO4 2-/In2O3The attapulgite of solid acid is catalyst,
The dosage of catalyst accounts for the 2wt% of the gross mass of overall reaction system, and irradiation reaction 10min under microwave, obtains 5- hydroxyls at 160 DEG C
Methyl furfural.
Embodiment 2：
(1) it is 1 according to the solid-to-liquid ratio of cellulose and alkali lye:80, by cotton fiber or wood fibre of the size less than 5mm
After cellulose is soaked in alkali lye fully infiltration, the Ultrasonic Pulverization 30min under 500W power, it is 1 to add mass ratio:1.5 acid
Cellulase and glucose oxidase (enzyme activity 20000U/g) mixed enzyme, handle 60min at 50 DEG C, filter off except residual
Slag, the cellulose solution digested, wherein the content of sodium gluconate is 40wt% in the cellulose solution digested.
(2) it is raw material by the cellulose solution of enzymolysis, to load SO4 2-/In2O3The attapulgite of solid acid is catalyst,
The dosage of catalyst accounts for the 5wt% of the gross mass of overall reaction system, and irradiation reaction 30min under microwave, obtains 5- hydroxyls at 200 DEG C
Methyl furfural.
Embodiment 3：
(1) it is 1 according to the solid-to-liquid ratio of cellulose and alkali lye:60, by cotton fiber or wood fibre of the size less than 5mm
After cellulose is soaked in alkali lye fully infiltration, the Ultrasonic Pulverization 15min under 450W power, it is 1 to add mass ratio:1.2 acid
Cellulase and glucose oxidase (enzyme activity 18000U/g) mixed enzyme, handle 45min at 45 DEG C, filter off except residual
Slag, the cellulose solution digested, wherein the content of sodium gluconate is 30wt% in the cellulose solution digested.
(2) it is raw material by the cellulose solution of enzymolysis, to load SO4 2-/In2O3The attapulgite of solid acid is catalyst,
The dosage of catalyst accounts for the 3.5wt% of the gross mass of overall reaction system, and irradiation reaction 25min under microwave, obtains 5- at 190 DEG C
Hydroxymethylfurfural.
Embodiment 4：
(1) it is 1 according to the solid-to-liquid ratio of cellulose and alkali lye:75, by cotton fiber or wood fibre of the size less than 5mm
After cellulose is soaked in alkali lye fully infiltration, the Ultrasonic Pulverization 25min under 450W power, it is 1 to add mass ratio:1.4 acid
Cellulase and glucose oxidase (enzyme activity 19000U/g) mixed enzyme, handle 50min at 42 DEG C, filter off except residual
Slag, the cellulose solution digested, wherein the content of sodium gluconate is 32wt% in the cellulose solution digested.
(2) it is raw material by the cellulose solution of enzymolysis, to load SO4 2-/In2O3The attapulgite of solid acid is catalyst,
The dosage of catalyst accounts for the 4.5wt% of the gross mass of overall reaction system, and irradiation reaction 10min under microwave, obtains 5- at 175 DEG C
Hydroxymethylfurfural.
Embodiment 5：
(1) it is 1 according to the solid-to-liquid ratio of cellulose and alkali lye:50, by cotton fiber or wood fibre of the size less than 5mm
After cellulose is soaked in alkali lye fully infiltration, the Ultrasonic Pulverization 10min under 500W power, it is 1 to add mass ratio:1.5 acid
Cellulase and glucose oxidase (enzyme activity 15000U/g) mixed enzyme, handle 30min at 50 DEG C, filter off except residual
Slag, the cellulose solution digested, wherein the content of sodium gluconate is 35wt% in the cellulose solution digested.
(2) it is raw material by the cellulose solution of enzymolysis, to load SO4 2-/In2O3The attapulgite of solid acid is catalyst,
The dosage of catalyst accounts for the 2wt% of the gross mass of overall reaction system, and irradiation reaction 10min under microwave, obtains 5- hydroxyls at 200 DEG C
Methyl furfural.
Embodiment 6：
(1) it is 1 according to the solid-to-liquid ratio of cellulose and alkali lye:80, by cotton fiber or wood fibre of the size less than 5mm
After cellulose is soaked in alkali lye fully infiltration, the Ultrasonic Pulverization 10-30min under 300W power, it is 1 to add mass ratio:1.5
Acid cellulose enzyme and glucose oxidase (enzyme activity 15000U/g) mixed enzyme, handle 30min at 50 DEG C, filter off except residual
Slag, the cellulose solution digested, wherein the content of sodium gluconate is 30wt% in the cellulose solution digested.
(2) it is raw material by the cellulose solution of enzymolysis, to load SO4 2-/In2O3The attapulgite of solid acid is catalyst,
The dosage of catalyst accounts for the 5wt% of the gross mass of overall reaction system, and irradiation reaction 30min under microwave, obtains 5- hydroxyls at 160 DEG C
Methyl furfural.
After testing, embodiment 1-6 prepares the production after the reaction same time of the 5 hydroxymethyl furfural prepared with prior art
The result of rate is as follows：
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | Comparative example | |
| Yield (%) | 78 | 86 | 82 | 79 | 84 | 82 | 16.5 |
As seen from the above table, the preparation method short time internal efficiency of 5 hydroxymethyl furfural prepared by the present invention is more preferable, has very
Good application prospect.
The above-described embodiments merely illustrate the principles and effects of the present invention, not for the limitation present invention.It is any ripe
Know the personage of this technology all can carry out modifications and changes under the spirit and scope without prejudice to the present invention to above-described embodiment.Cause
This, those of ordinary skill in the art is complete without departing from disclosed spirit and institute under technological thought such as
Into all equivalent modifications or change, should by the present invention claim be covered.
Claims (10)
1. a kind of production method of the 5 hydroxymethyl furfural of the cellulose solution based on enzymolysis, it is characterised in that including following step
Suddenly：
(1) after the cellulose after crushing being soaked in alkali lye into fully infiltration, Ultrasonic Pulverization, it is 1 to add mass ratio:1-1.5
Acid cellulose enzyme and glucose oxidase mixing ferment treatment, filter off the cellulose solution except residue, digested；
(2) it is raw material by the cellulose solution of enzymolysis, to load SO4 2-/In2O3The attapulgite of solid acid is catalyst, micro-
Irradiation reaction under ripple, obtains 5 hydroxymethyl furfural.
2. a kind of production method of the 5 hydroxymethyl furfural of cellulose solution based on enzymolysis according to claim 1, its
It is characterised by：In the step (1), the raw material of cellulose is cotton fiber or wood fibre.
3. a kind of production method of the 5 hydroxymethyl furfural of cellulose solution based on enzymolysis according to claim 1, its
It is characterised by：In the step (1), the size of the cellulose after crushing is less than 5mm.
4. a kind of production method of the 5 hydroxymethyl furfural of cellulose solution based on enzymolysis according to claim 1, its
It is characterised by：In the step (1), the power of Ultrasonic Pulverization is 300-500W, time 10-30min.
5. a kind of production method of the 5 hydroxymethyl furfural of cellulose solution based on enzymolysis according to claim 1, its
It is characterised by：In the step (1), the enzyme activity of mixed enzyme is 15000-20000U/g.
6. a kind of production method of the 5 hydroxymethyl furfural of cellulose solution based on enzymolysis according to claim 1, its
It is characterised by：In the step (1), the temperature of enzymolysis is 40-50 DEG C, time 30-60min.
7. a kind of production method of the 5 hydroxymethyl furfural of cellulose solution based on enzymolysis according to claim 1, its
It is characterised by：In the step (1), the content of sodium gluconate is not less than 20wt% in the cellulose solution of enzymolysis.
8. a kind of production method of the 5 hydroxymethyl furfural of cellulose solution based on enzymolysis according to claim 1, its
It is characterised by：In the step (2), the temperature of irradiation reaction is 160-200 DEG C under microwave, time 10-30min.
9. a kind of production method of the 5 hydroxymethyl furfural of cellulose solution based on enzymolysis according to claim 1, its
It is characterised by：In the step (2), the dosage of catalyst accounts for the 2-5wt% of the gross mass of overall reaction system.
10. a kind of production method of the 5 hydroxymethyl furfural of cellulose solution based on enzymolysis according to claim 1, its
It is characterised by：In the step (2), the yield of 5 hydroxymethyl furfural is not less than 70%.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106544370A (en) * | 2016-10-21 | 2017-03-29 | 广东启智生物科技有限公司 | It is a kind of reduce lignocellulose alkaline process pretreatment fluid in by-product depression effect method and cellulosic ethanol is prepared based on the method |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106544370A (en) * | 2016-10-21 | 2017-03-29 | 广东启智生物科技有限公司 | It is a kind of reduce lignocellulose alkaline process pretreatment fluid in by-product depression effect method and cellulosic ethanol is prepared based on the method |
Non-Patent Citations (2)
| Title |
|---|
| 王堃: "木质生物质预处理、组分分离及酶解糖化研究", 《北京林业大学博士学位论文》 * |
| 高建民等: "一株嗜热嗜酸纤维素酶高产霉菌分离鉴定及其酶学性质研究", 《微生物学通报》 * |
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Application publication date: 20180306 |