CN108084121A - It is a kind of by the carbohydrate-modifying method for furfural of cellulose family - Google Patents
It is a kind of by the carbohydrate-modifying method for furfural of cellulose family Download PDFInfo
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- CN108084121A CN108084121A CN201711204086.XA CN201711204086A CN108084121A CN 108084121 A CN108084121 A CN 108084121A CN 201711204086 A CN201711204086 A CN 201711204086A CN 108084121 A CN108084121 A CN 108084121A
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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
- C07D307/48—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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- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a kind of by the carbohydrate-modifying method for furfural of cellulose family, include the following steps：In the nitrogen of 0~4MPa or hydrogen gas atmosphere, by cellulose family carbohydrate and acid catalyst according to 1:50~50:1 mass ratio is mixed to get mixture, then the annular water-soluble reaction medium of 10~100 times of quality of mixture is added, and the water content of annular water-soluble reaction medium is no more than 10wt%, 0.15~5.0h is reacted at 100~200 DEG C after mixing, then reaction product is filtered, extracted, be evaporated under reduced pressure, obtain furfural.The present invention has many advantages, such as that simple for process, mild condition, furfural yield are higher, and dependence when avoiding existing industrially prepared furfural to hemicellulose, breach cellulose family it is carbohydrate-modifying when being furfural using H beta-molecular sieves and lactone compound as the limitation of reaction system, expand and can be applied to the scope that biomass resource is converted into furfurol reaction system.
Description
Technical field
The invention belongs to technical field of biomass chemical engineering, it is more particularly related to a kind of by cellulose family carbon aquation
Close the method that object is converted into furfural.
Background technology
Furfural is a kind of platform chemical combination that preparation can be converted by biomass as derivative important in furfuran compound
Object.By aoxidize, be condensed etc. reactions can by its directly as Material synthesis go out to be applied to medicine, pesticide, resin, daily use chemicals, casting,
The biomass-based platform chemicals of the industries such as weaving and oil.Meanwhile furfural still prepares biogasoline, biodiesel and biology
The important source material of Aviation Fuel.
The raw material of furfurol industry production depends on the hemicellulose in biomass components.Sugar in hemicellulose structure
Glycosidic bond is protonated and is broken rapidly under acid catalyst effect, and the carbonium ion that end is formed ultimately forms five with water interaction
Carbon monose.Then, the hydroxyl proton on pentose sloughs two molecular waters and cyclization obtains furfural.It although can be by life using the method
Hemicellulose in material composition is converted into furfural, but during furfural production, generates with substantial amounts of furfuraldehyde waste slag, often give birth to
1 ton of furfural of production about discharges 10 tons or more residues.Cellulose in reaction process is hexose there is no effective depolymerization and to be converted into
Furfural.
Cellulose family is carbohydrate-modifying for during furfural, depolymerization first is hexose monomer, then to six carbon
Making choice property of carbon-carbon single bond fracture in sugar, sloughs and pentose is formed after a carbon atom, after further cyclodehydration
Form furfural.Initially, the aqueous solution of glucose can obtain yield after reacting 0.2~1.5s under 400 DEG C, 80MPa pressure conditions
For 0.3~12.2% furfural.Although without addition catalyst, the severe reaction conditions, to equipment in the reaction process
It is required that it is high, and furaldehyde yield is relatively low, it is difficult to achieve the purpose that application.
Glucose is in the reaction medium of gamma-valerolactone-water (water content 10wt%) under the conditions of 175 DEG C, through H beta molecules
The furfural that yield is respectively 37% is can obtain after sieve effect 40min.Although the cellulose family carbon hydrate used in research process
Object can be converted into furfural, but the catalyst reacted is confined to H beta-molecular sieves, and reaction medium is confined to lactone compound.And lactone
Class compound is expensive, and hydrolysis easily occurs for structural instability.
The content of the invention
It is an object of the invention to：Exploitation is suitable for the carbohydrate-modifying reaction system for furfural of cellulose family, leads to
The concerted catalysis of reaction medium and acid catalyst is crossed, cellulose family carbohydrate is efficiently converted into furfural, is broken through existing
Reaction system expands to the limitation of reaction medium (lactone compound) and catalyst (H beta-molecular sieves) and can be applied to cellulose family carbon
Hydrate is converted into the reaction system scope of furfural.
In order to realize foregoing invention purpose, the present invention provides a kind of that cellulose family is carbohydrate-modifying for furfural
Method includes the following steps：
In the nitrogen of 0~4MPa or hydrogen gas atmosphere, by cellulose family carbohydrate and acid catalyst according to 1:
50~50:1 mass ratio is mixed to get mixture, and the annular water-soluble reaction for then adding 10~100 times of quality of mixture is situated between
Matter, and the water content of annular water-soluble reaction medium is no more than 10wt%, reacts 0.15 at 100~200 DEG C after mixing
Then reaction product is filtered, extracted, is evaporated under reduced pressure, obtains furfural by~5.0h.
The principle of the present invention is：The sugar charcoal chain generated after cellulose family carbohydrate depolymerization, through annular water-soluble reaction
The synergistic effect of medium and acid catalyst, selectivity form pentose, further cyclodehydration shape after being broken a carbon-carbon single bond
Into furfural, realize that cellulose family carbohydrate is efficiently converted into furfural.
It is described as the present invention by a kind of optimal technical scheme of the carbohydrate-modifying method for furfural of cellulose family
Cellulose family carbohydrate is glucose, fructose, sucrose or cellulose.
It is described as the present invention by a kind of optimal technical scheme of the carbohydrate-modifying method for furfural of cellulose family
Acid catalyst is H beta-molecular sieves or sulfuric acid.
It is described as the present invention by a kind of optimal technical scheme of the carbohydrate-modifying method for furfural of cellulose family
Annular water-soluble reaction medium is gamma-butyrolacton, tetrahydrofuran, sulfolane or 1,4- dioxane.
The target product of the above-mentioned reaction system of the present invention is furfural, and by-product is mainly 5 hydroxymethyl furfural.Wherein, 5- hydroxyls
Methyl furfural is tested (Detection wavelength with furfural using 2489 UV detector of high performance liquid chromatography：284nm).
Compared with the prior art, the present invention has the carbohydrate-modifying method for furfural of cellulose family following beneficial
Effect：
(1) in the water-soluble organic system of chain, (such as dimethyl is sub- for cellulose family carbohydrate for the method for the present invention
Sulfone, N ' dinethylformamides, rudimentary Organic Alcohol, aldehyde, acid etc.) in the problem of being difficult to convert into furfural, first in acid catalyst
Under the action of cellulose family carbohydrate depolymerization is converted into hexose, then in annular water-soluble organic media to hexose
More pentose is generated under the stabilization of the enol form transition state substance generated in the reaction of inverse aldehyde alcohol, and final dewatering is given birth to
Into furfural.The reaction system has many advantages, such as cheap, stable structure；
(2) present invention has many advantages, such as that simple for process, mild condition, furfural yield are higher, and avoids existing industry system
Dependence during standby furfural to hemicellulose, breach cellulose family it is carbohydrate-modifying for furfural when with H beta-molecular sieves and lactone
Compound is the limitation of reaction system, expands and can be applied to the scope that biomass resource is converted into furfurol reaction system.
Description of the drawings
With reference to the accompanying drawings and detailed description, technical solution of the present invention and advantageous effect are described in detail.
Fig. 1 is the reaction principle figure of the invention by the carbohydrate-modifying method for being furfural of cellulose family.
Fig. 2 is the HPLC collection of illustrative plates of furfural in 6 products therefrom of the embodiment of the present invention.
Fig. 3 is the HPLC collection of illustrative plates of furfural in 11 products therefrom of the embodiment of the present invention.
Specific embodiment
In order to become apparent from the purpose of the present invention, technical solution and advantageous effects, with reference to embodiments, to this
Invention is further elaborated.It should be appreciated that the embodiment described in this specification is just for the sake of this hair of explanation
It is bright, be not intended to limit the present invention, parameter, ratio of embodiment etc. can adaptation to local conditions make a choice and substance had no to result
It influences.
Embodiment 1
0.5g glucose is taken, according to 5:1 ratio addition H beta-molecular sieves, then add in 20 times of tetrahydrofurans and are mixed to get instead
Stoste is answered to be added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, at 180 DEG C
React 2.0h；After reaction terminates to be cooled to room temperature, liquid and catalyst are collected, takes reaction system mixing liquid efficient liquid phase
Chromatography (HPLC) measures, and the yield of furfural is 25.59%.
Embodiment 2
0.5g glucose is taken, according to 5:1 ratio addition H beta-molecular sieves, then add in 20 times of gamma-butyrolactons and are mixed to get
Reaction stoste is added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, at 180 DEG C
Lower reaction 2.0h；After reaction terminates to be cooled to room temperature, liquid and catalyst are collected, takes reaction system mixture liquid with efficiently
Liquid chromatogram (HPLC) measures, and the yield of furfural is 34.56%.
Embodiment 3
0.5g glucose is taken, according to 5:1 ratio addition H beta-molecular sieves, then add in 20 times of sulfolane and are mixed to get reaction
Stoste is added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, it is anti-at 180 DEG C
Answer 2.0h；It treats to be cooled to room temperature after reaction, collects liquid and catalyst, take reaction system mixing liquid high-efficient liquid phase color
It composes (HPLC) to measure, the yield of furfural is 20.80%.
Embodiment 4
0.5g glucose is taken, according to 5:1 ratio addition H beta-molecular sieves, then add in 20 times of Isosorbide-5-Nitrae-dioxane and mix
It is added to reaction stoste in reaction kettle；After air in nitrogen displacement kettle, pressure in kettle is risen into 2.0MPa, at 180 DEG C
React 2.0h；After reaction terminates to be cooled to room temperature, liquid and catalyst are collected, takes reaction system mixing liquid efficient liquid phase
Chromatography (HPLC) measures, and the yield of furfural is 31.62%.
Embodiment 5
0.5g glucose is taken, according to 5:1 ratio addition H beta-molecular sieves, then add in the mixing of 15 times of tetrahydrofurans and water
Object (water content 5wt%) is mixed to get reaction stoste and is added in reaction kettle；With air in nitrogen displacement kettle three times after, by kettle
Middle pressure rises to 2.0MPa, reacts 2.0h at 180 DEG C；After reaction terminates to be cooled to room temperature, liquid and catalyst are collected, is taken
Reaction system mixes liquid high performance liquid chromatography (HPLC) measure, and the yield of furfural is 23.44%.
Embodiment 6
0.2g glucose is taken, according to 5:1 ratio addition H beta-molecular sieves, then add in 35 times of tetrahydrofurans and are mixed to get instead
Stoste is answered to be added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, at 180 DEG C
React 2.0h；After reaction terminates to be cooled to room temperature, liquid and catalyst are collected, reaction system is taken to mix liquid high-efficient liquid phase color
It composes (HPLC) to measure, the yield of furfural is 35.19%.
Embodiment 7
0.5g glucose is taken, according to 20:1 ratio addition sulfuric acid, then adds in 75 times of sulfolane and is mixed to get reaction original
Liquid is added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, is reacted at 180 DEG C
1.0h；After reaction terminates to be cooled to room temperature, liquid is collected, reaction system mixing liquid high performance liquid chromatography (HPLC) is taken to survey
Fixed, the yield of furfural is 32.56%.
Embodiment 8
0.5g glucose is taken, according to 20:1 ratio addition sulfuric acid, then adds in 75 times of gamma-butyrolactons and is mixed to get reaction
Stoste is added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, it is anti-at 180 DEG C
Answer 1.0h；After reaction terminates to be cooled to room temperature, liquid is collected, takes reaction system mixing liquid high performance liquid chromatography (HPLC)
It measures, the yield of furfural is 24.88%.
Embodiment 9
0.5g fructose is taken, according to 20:1 ratio addition sulfuric acid, then adds in 75 times of sulfolane and is mixed to get reaction stoste
It is added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, is reacted at 180 DEG C
1.0h；After reaction terminates to be cooled to room temperature, liquid is collected, reaction system mixing liquid high performance liquid chromatography (HPLC) is taken to survey
Fixed, the yield of furfural is 32.37%.
Embodiment 10
0.5g sucrose is taken, according to 20:1 ratio addition sulfuric acid, then adds in 75 times of sulfolane and is mixed to get reaction stoste
It is added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, is reacted at 180 DEG C
1.0h；After reaction terminates to be cooled to room temperature, liquid is collected, reaction system mixing liquid high performance liquid chromatography (HPLC) is taken to survey
Fixed, the yield of furfural is 46.45%.
Embodiment 11
0.5g celluloses are taken, according to 20:1 ratio addition sulfuric acid, then adds in 75 times of sulfolane and is mixed to get reaction original
Liquid is added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, is reacted at 180 DEG C
1.0h.After reaction terminates to be cooled to room temperature, liquid is collected, reaction system mixing liquid high performance liquid chromatography (HPLC) is taken to survey
Fixed, the yield of furfural is 43.46%.
Embodiment 12
0.5g glucose is taken, according to 5:1 ratio addition H beta-molecular sieves, then add in 20 times of dimethyl sulfoxides and are mixed to get instead
Stoste is answered to be added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, at 180 DEG C
React 2.0h；After reaction terminates to be cooled to room temperature, liquid and catalyst are collected, takes reaction system mixture liquid with efficient liquid
Phase chromatography (HPLC) measures, and the yield of furfural is 2.23%.
Embodiment 13
0.5g glucose is taken, according to 20:1 ratio addition sulfuric acid, then adds in 70 times of dimethyl sulfoxides and is mixed to get reaction
Stoste is added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa, it is anti-at 180 DEG C
Answer 1.0h.After reaction terminates to be cooled to room temperature, liquid is collected, takes reaction system mixing liquid high performance liquid chromatography (HPLC)
It measures, the yield of furfural is 6.29%.
Embodiment 14
0.5g glucose is taken, according to 20:1 ratio addition sulfuric acid, then adds in 70 times of n,N-Dimethylformamide mixing
Reaction stoste is obtained to be added in reaction kettle；With air in nitrogen displacement kettle three times after, pressure in kettle is risen into 2.0MPa,
1.0h is reacted at 180 DEG C.After reaction terminates to be cooled to room temperature, liquid is collected, takes reaction system mixing liquid efficient liquid phase
Chromatography (HPLC) measures, and the yield of furfural is 2.74%.
According to the disclosure and teachings of the above specification, those skilled in the art in the invention can also be to above-mentioned embodiment party
Formula carries out appropriate change and modification.Therefore, the invention is not limited in specific embodiment disclosed and described above, to this
Some modifications and changes of invention should also be as falling into the scope of the claims of the present invention.In addition, although this specification
In used some specific terms, but these terms are merely for convenience of description, do not limit the present invention in any way.
Claims (4)
- It is 1. a kind of by the carbohydrate-modifying method for furfural of cellulose family, which is characterized in that it includes the following steps：In the nitrogen of 0~4MPa or hydrogen gas atmosphere, by cellulose family carbohydrate and acid catalyst according to 1:50~ 50:1 mass ratio is mixed to get mixture, then adds the annular water-soluble reaction medium of 10~100 times of quality of mixture, and The water content of annular water-soluble reaction medium be no more than 10wt%, after mixing at 100~200 DEG C reaction 0.15~ Then reaction product is filtered, extracted, is evaporated under reduced pressure, obtains furfural by 5.0h.
- 2. the carbohydrate-modifying method for furfural of cellulose family according to claim 1, which is characterized in that the fibre The plain class carbohydrate of dimension is glucose, fructose, sucrose or cellulose.
- 3. the carbohydrate-modifying method for furfural of cellulose family according to claim 1, which is characterized in that the acid Catalyst is H beta-molecular sieves or sulfuric acid.
- 4. the carbohydrate-modifying method for furfural of cellulose family according to claim 1, which is characterized in that the ring Shape water-soluble reaction medium is gamma-butyrolacton, tetrahydrofuran, sulfolane or 1,4- dioxane.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113649063A (en) * | 2021-08-19 | 2021-11-16 | 中科合成油技术有限公司 | Method for preparing furfural by catalyzing decarbonization of hexose |
| CN114790183A (en) * | 2022-04-14 | 2022-07-26 | 安徽农业大学 | Method for synthesizing 5-hydroxymethylfurfural by catalyzing conversion of glucose |
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| CN105111170A (en) * | 2015-09-14 | 2015-12-02 | 中国科学技术大学 | Preparation method for furan compound |
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2017
- 2017-11-27 CN CN201711204086.XA patent/CN108084121A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105111170A (en) * | 2015-09-14 | 2015-12-02 | 中国科学技术大学 | Preparation method for furan compound |
Non-Patent Citations (6)
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| CUI JINGLEI等: ""Conversion of carbohydrates to furfural via selective cleavage of the carbon-carbon bond: the cooperative effects of zeolite and solvent"", 《GREEN CHEMISTRY》 * |
| ELIF I. GURBUZ等: ""Conversion of Hemicellulose into Furfural Using Solid Acid Catalysts in γ-Valerolactone"", 《ANGEW. CHEM. INT. ED.》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113649063A (en) * | 2021-08-19 | 2021-11-16 | 中科合成油技术有限公司 | Method for preparing furfural by catalyzing decarbonization of hexose |
| CN114790183A (en) * | 2022-04-14 | 2022-07-26 | 安徽农业大学 | Method for synthesizing 5-hydroxymethylfurfural by catalyzing conversion of glucose |
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Application publication date: 20180529 |