CN106810517A - It is a kind of that the method that 5 hydroxymethyl furfural continuously synthesizes is realized by continuous extraction - Google Patents
It is a kind of that the method that 5 hydroxymethyl furfural continuously synthesizes is realized by continuous extraction Download PDFInfo
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- 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
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Abstract
The method that 5 hydroxymethyl furfural continuously synthesizes is realized by continuous extraction the invention discloses a kind of, the method is in a reaction system for generating 5 hydroxymethyl furfural, by continuously entering extractant, by the 5 hydroxymethyl furfural continuous extraction generated in reaction system and take reaction system out of, realize the continuous output of 5 hydroxymethyl furfural.The production technology that glucose designed by the present invention prepares 5 hydroxymethyl furfural can realize the large-scale production of the 5 hydroxymethyl furfural under the conditions of green process for cleanly preparing, be with a wide range of applications.
Description
Technical field
The present invention relates to chemical reaction technical field, more particularly to one kind realizes 5- hydroxyl first by continuous extraction
The method that base furfural continuously synthesizes.
Background technology
With the exhaustion of the fossil resources such as Global Oil, natural gas, seek substitutable resources as the task of top priority
Volume.Biomass resource (plant, animal, microorganism) is produced using photosynthesis, is that one kind can be again
Production-goods source, therefore have with the fine chemical product that biomass prepare necessary for human instead of traditional fossil resource
There is important Research Significance.5 hydroxymethyl furfural has furan nucleus, aldehyde radical and hydroxyl, is a kind of chemical property
Active chemical intermediate, can be with prospect by the reaction various derivatives of generation such as oxidation, hydrogenation
Fine chemical material.Since being reported by carbohydrate degradation acquisition 5 hydroxymethyl furfural, from life
It is the focus of numerous researchs that material based raw material prepares 5 hydroxymethyl furfural and becomes.
It is relevant at present in the research for preparing 5 hydroxymethyl furfural, with natural Fengdu is high can be by fibre in non-edible plant
The glucose that dimension element hydrolysis is obtained is considered to have the raw material for preparing 5 hydroxymethyl furfural of economy.And with
Glucose is difficult compared with by raw material of fructose for raw material prepares 5 hydroxymethyl furfural, it is difficult to realize high efficiency Gao Xuan
Selecting property is converted into 5 hydroxymethyl furfural.Zhang Zongchao [Zhao H, Holladay JE, Brown H, Zhang ZC.
Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethyl furfural.
Science.2007Jun15；316(5831):1597-600] [EMIM] Cl-CrCl is used first2Catalyst system and catalyzing, will
Glucose is converted into 5 hydroxymethyl furfural, can be obtained under conditions of 10-20wt% in concentration of glucose
The 5 hydroxymethyl furfural yield of 50-70%.Open ancestor's over-extraction CuCl2-CrCl2Bimetallic catalyst system, with fiber
Element is reaction raw materials, has obtained the 5 hydroxymethyl furfural of yield more than 50%, is directly to prepare 5- from biomass
Hydroxymethylfurfural is provided greatly may.
In ion liquid system, with the rising of concentration of glucose, glucose is converted into 5 hydroxymethyl furfural
Selectivity reduction.When glucose quality fraction accounts for ionic liquid quality 20wt%, the choosing of 5 hydroxymethyl furfural
More than 65%, and when concentration of glucose reaches 80wt%, the yield of 5 hydroxymethyl furfural drops to selecting property
30% or so.And it is to realize that glucose conversion prepares 5 hydroxymethyl furfural industry to realize that the high concentration of glucose is converted
The important step of level production.Meanwhile, ionic liquid character stabilization, boiling point are high, high from ion liquid system
The 5 hydroxymethyl furfural of isolating of effect is also challenged for one.A kind of Zhang Zongchao [synthesis 5- hydroxyl first of Zhang Zongchao, Zhou Jinxia
The method of base furfural:China, 201410047832.9 [P] .2014.02.11] added using in ionic reaction system
Alcohol ethers material, realizes the efficient reaction for preparing 5 hydroxymethyl furfural of glucose conversion under high concentration system
Journey, it is organic molten that the 5 hydroxymethyl furfural part that can react generation in phase using the method enters into alcohol ethers
In agent.
In the reaction system as solvent with water, 5 hydroxymethyl furfural less stable, the work of Dumesic
[Leshkov Y Rt Chheda J N, Dumesic J A.Phase modifiers promote efficient
Production of hydroxymethylfurfural from fructose [J] .Science, 2006,312 (5782)：
1933-1937.] in, using in the diphasic system that water phase and organic phase are constituted, methyl iso-butyl ketone (MIBK) extracts for reaction
Agent is taken, more than 70% 5 hydroxymethyl furfural yield can be obtained.
Above-mentioned ionic liquid and water as reaction dissolvent reaction system, all using the reaction of batch tank
Device, realizes the efficient preparation of 5 hydroxymethyl furfural by building biphasic reaction system and efficiently separates.So
And, using the technique for preparing 5 hydroxymethyl furfural of batch (-type), it is impossible to ensure single-autoclave yield rate higher, reaction
A large amount of extractants take substantial amounts of reaction compartment in device, while after reaction scale expansion, mutual exclusive two
Alternate mass transfer can also be affected.Therefore two kinds of above-mentioned production technologies are not particularly suited for the production of scale.
The technique of the continuous 5 hydroxymethyl furfural of the continuous extraction of invention, by building continuous reaction system
And the continuous extraction process for reacting phase is continued through using extractant, may be implemented in measured response space
Reaction is with extractant ratio adjustable, it is to avoid the limitation of single-autoclave yield rate in batch production process, and alternate
The restriction of mass transfer, therefore the reaction process of invention, are to realize producing 5- methylol chaffs with lignocellulosic
One kind of aldehyde large-scale production has potential method.
The content of the invention
The side that 5 hydroxymethyl furfural continuously synthesizes is realized by continuous extraction it is an object of the invention to provide a kind of
Method, efficiently synthesizing for 5 hydroxymethyl furfural is realized by the reaction process of continuous extraction.
It is a kind of that the method that 5 hydroxymethyl furfural continuously synthesizes is realized by continuous extraction, generate 5- hydroxyl first at one
In the reaction system of base furfural, by continuously entering extractant, by the 5- methylols generated in reaction system
Furfural continuous extraction simultaneously takes reaction system out of, realizes the continuous output of 5 hydroxymethyl furfural.
The method by reaction mass during the course of the reaction accomplished continuously or intermittently property add, reaction dissolvent and catalyst
Repeatedly use and offline update realize the company that reaction raw materials are converted into 5 hydroxymethyl furfural course of reaction
It is continuous.Meanwhile, extractant continues through reaction phase, and 5 hydroxymethyl furfural constantly extracted into reaction phase, and
After extractant is separated with 5 hydroxymethyl furfural, again flow into reactor and extracted, realize extractant process
Continuously.Coupled by successive reaction and continuous extraction, realize the continuous production of 5 hydroxymethyl furfural.
The reaction mutually includes reaction dissolvent, catalyst, reaction raw materials.
The reaction raw materials be lignocellulosic or its derivative polysaccharide or monose, including lignocellulosic derive
Cellulose, oligomeric cellulose, glucose, glucose oligosaccharide, AHG, starch, fructose in
It is at least one.
The reaction dissolvent may include：At least a kind in ionic liquid, the salting liquid of water, organic solvent.
Described ionic liquid is glyoxaline ion liquid or choline-like ionic liquid；
The structural formula of the glyoxaline ion liquid is：
Wherein, X is Cl, Br, OAc, CH3SO3、NTf2、BF4、PF6At least one of；N=1-12；
The choline-like ionic liquid structural formula：
Wherein, X is Cl, Br, OAc, CH3SO3、NTf2、BF4、PF6At least one of；R1, R2,
R3It is C1-C12Alkyl.
The organic solvent：
It is dimethyl sulfoxide (DMSO), N, N-dimethylformamide, acetonitrile, butyl acetate.
The salting liquid of the water is：
Sodium chloride, magnesium chloride, potassium chloride, calcium chloride etc. can improve 5 hydroxymethyl furfural and divide in diphasic system
The inorganic salt solution of distribution coefficient.
The extractant of methods described is at least one in alcohol, ether, alkane, ketone.
The alcohol includes C1~C5Straight chain or straight-chain alkyl alcohol；
The ether includes glycol monoethyl ether, glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol two
Methyl ether, methyl-isobutyl ether, tetrahydrofuran；Ketone includes methyl iso-butyl ketone (MIBK), acetylacetone,2,4-pentanedione；
The alkane includes C6~C18Linear paraffin or cycloalkane.
The catalyst is at least one in slaine, solid acid catalyst, liquid acid catalyst.
The slaine is：CrCl2·xH2O, CrCl3·xH2O, CuCl, CuCl2·xH2O, AlCl3,
LaCl3·xH2O, FeCl3·xH2O, ZnCl2·xH2O, LiCl, SnCl4,；
The solid acid catalyst is：Acid MFI, AFI, Beta zeolite molecular sieve, acid phenolic resin；
The liquid acid：Sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, benzene sulfonic acid.
Methods described, reaction temperature is 90-200 DEG C, and reaction pressure is 0.1--6MPa.
Advantages of the present invention：
A kind of method that the continuous synthesis of 5 hydroxymethyl furfural is realized by continuous extraction mentioned by the present invention, energy
Enough realize the ON-LINE SEPARATION in the Efficient Conversion and course of reaction of 5 hydroxymethyl furfural.The present invention is by building
Extractant continues through reaction phase, and flows continually out the extractant circulatory system of reactor, realizes limited
Reaction compartment in extractant and reaction phase arbitrary proportion modulation.5 hydroxymethyl furfural is extracted in course of reaction
Take agent and continuously take reactor, and ON-LINE SEPARATION during the course of the reaction out of, at the same extractant with 5- methylol chaffs
Aldehyde is recycled in systems after separating.By continuous extraction, and the adjustable extraction process of extractant flow velocity,
The usage cycles of reaction dissolvent and catalyst can effectively be extended, while the timely extraction point from reaction phase
Separating out 5 hydroxymethyl furfural can effectively improve the yield of 5 hydroxymethyl furfural in course of reaction.
Brief description of the drawings
Fig. 1 is suitable for the continuous production 5 hydroxymethyl furfural artwork designed by the present invention；
In figure：1 reactor, 2 reaction phases, 3 extractant preheaters, 4 extractants and product separator.
Specific embodiment
Below in conjunction with the accompanying drawings 1 and implementation method the present invention is described in further detail：
A kind of method for continuously synthesizing that 5 hydroxymethyl furfural is realized by continuous extraction, can lead to described in the present embodiment
Following flow is crossed to realize：
1) reaction raw materials, reaction dissolvent and catalyst are configured to homogeneous reaction phase solution, the company of being added to
In continuous reactor, reaction raw materials are with reaction dissolvent mass ratio 1:Between 1~100, catalyst and reactant thing
Mass ratio is 1:Between 5~20,
2) extractant is preheated, after being preheating to 90-200 DEG C, with the flow of 10-30ml/min from reactor bottom
Portion is continuously entered into reactor；
3) in flow reactor, reaction phase solution is heated to via the extractant and reactor side wall of preheating
90-200 DEG C is reacted, and the reactant in reaction phase solution is converted into 5 hydroxymethyl furfural；
4) continuously across reaction phase solution, 5 hydroxymethyl furfural is dissolved in extractant extractant, constantly quilt
Take reaction phase out of, the extractant with 5 hydroxymethyl furfural of outflow reactor is separated into product with extractant
Device；
5) extractant for 5 hydroxymethyl furfural separate is preheated to reaction temperature again, flows into and enter in reactor
The extraction of row reactant；
6) product efficient liquid phase chromatographic analysis, internal standard compound is done with glycerine.
The cumulative amount of described extractant is with the volume ratio of reaction dissolvent 1~20:1.
The computational methods of reaction conversion ratio, the selectivity of HMF and yield are as follows：
HMF selectivity (%)=yield/conversion ratio × 100
Embodiment 1
Using the above method, by 15g glucose, 30g ionic liquids (BMIMCl), 0.74g, 6.0g water
The reaction phase of composition, at 90 DEG C, under pressure 0.2Mpa, reacts 1 hour, and glycol dimethyl ether is preheated to
90 DEG C, during the course of the reaction glycol dimethyl ether reaction phase is flowed in series through with the speed of 10ml/min, by 5- hydroxyls
Methyl furfural continuous extraction goes out reaction system, and flowing into piece-rate system via extractant calmness system is separated.
Obtain inversion rate of glucose 26.4%, 5 hydroxymethyl furfural selectivity 70.5%.
Embodiment 2
Using the above method, will be by 15g glucose, 30g ionic liquids (chlorination monobutyl tri-methylimidazolium
(BMIMCl))、1.1g CrCl3‐6H2The reaction phase that O, 6g water are constituted, in 130 deg. C Pressure 2.0MP
Under, react 15 minutes, during the course of the reaction, glycol dimethyl ether is continuously preheated to 130 DEG C with 20ml/min
Speed continuous conveying enter flow reactor, flow in series through reaction and mutually extracted, and heavy via extractant
Quiet system flows into piece-rate system and is separated.It is 97.6% to obtain the conversion ratio of glucose, 5 hydroxymethyl furfural choosing
Selecting property is 50.29%.Using identical proportioning, identical reaction temperature and under the reaction time is stirred in small magnetic
In the intermittent kettle reactor mixed, under the reaction condition of the extractant of addition 3 times of phase system of reaction, glucose
Conversion ratio is only 66%, the selectivity 41% of 5 hydroxymethyl furfural.
Embodiment 3
Using the above method, will be by 33gBMIMCl, 1.2g CrCl3‐6H2O, 6g water, 15g glucose are constituted
Reaction phase, at 182 DEG C, under conditions of pressure 2.8Mpa, react 10 minutes, second two during the course of the reaction
Diethylene glycol dimethyl ether is preheated to 200 DEG C, and reaction phase is flowed in series through with the speed of 30ml/min, by 5 hydroxymethyl furfural
Reaction phase is extracted, and piece-rate system is flowed into via extractant calmness system and separated.Glucose is obtained to turn
Rate is 96.9%, selectivity 57.8%.
Embodiment 4
Using the above method, will carry out conversion reaction mother liquor 60g (it is interior including BMIMCl, glucose,
CrCl3‐6H2O, water, glycol dimethyl ether, undetectable byproduct of reaction) as reaction dissolvent and urge
Agent, adds the DEXTROSE ANHYDROUS of 15g, reacts 15 minutes at a temperature of lower 130 DEG C of 2MP pressure, instead
Glycol dimethyl ether is preheated to after 130 DEG C and flows in series through reaction phase with the speed of 20ml/min during answering, and obtains
It is 88% to inversion rate of glucose, selectivity is 72%.
The continuous of the successive reaction continuous extraction agent designed by using the present invention is can be seen that as embodiment data
The preparation technology of 5 hydroxymethyl furfural, the 5 hydroxymethyl furfural that can obtain change than the technique of batch (-type) is selected
Property, meanwhile, using the technique designed by the present invention, the reaction mother liquor for obtaining can be utilized repeatedly, remain to keep
Reactivity.
Claims (8)
1. it is a kind of that the method that 5 hydroxymethyl furfural continuously synthesizes is realized by continuous extraction, it is characterised in that
In one reaction system of generation 5 hydroxymethyl furfural, by continuously entering extractant, by institute in reaction system
The 5 hydroxymethyl furfural continuous extraction of generation simultaneously takes reaction system out of, realizes the continuous output of 5 hydroxymethyl furfural.
2. according to described in claim 1 it is a kind of by continuous extraction realize 5 hydroxymethyl furfural continuously synthesis
Method, it is characterised in that by reaction raw materials during the course of the reaction accomplished continuously or intermittently property add, reaction dissolvent
Repeatedly use and update offline and realize the continuous flow procedure of 5 hydroxymethyl furfural with catalyst；Together
When, extractant continues through reaction phase, and 5 hydroxymethyl furfural constantly is extracted into reaction phase, and in extractant
After being separated with 5 hydroxymethyl furfural, again flow into reactor and extracted, realize the continuous of extractant process；
Coupled by successive reaction and continuous extraction, realize the continuous production of 5 hydroxymethyl furfural.
3. according to described in claim 2 it is a kind of by continuous extraction realize 5 hydroxymethyl furfural continuously synthesis
Method, it is characterised in that：The reaction mutually includes reaction dissolvent, catalyst and reaction raw materials.
4. according to described in claim 2 it is a kind of by continuous extraction realize 5 hydroxymethyl furfural continuously synthesis
Method, it is characterised in that described reaction raw materials are lignocellulosic or its derivative polysaccharide or monose, bag
Include cellulose derived from lignocellulosic, oligomeric cellulose, glucose, glucose oligosaccharide, AHG,
At least one in starch, fructose.
5. according to described in claim 2 it is a kind of by continuous extraction realize 5 hydroxymethyl furfural continuously synthesis
Method, it is characterised in that described reaction dissolvent may include：Ionic liquid, the salting liquid of water or organic molten
At least a kind in agent.
Described ionic liquid is glyoxaline ion liquid or choline-like ionic liquid；
The structural formula of the glyoxaline ion liquid is：
Wherein, X is Cl, Br, OAc, CH3SO3、NTf2、BF4、PF6At least one of；N=1-12；
The structural formula of the choline-like ionic liquid is：
Wherein, X is Cl, Br, OAc, CH3SO3、NTf2、BF4、PF6At least one of；R1, R2,
R3It is C1-C12Alkyl；
The organic solvent is：Dimethyl sulfoxide (DMSO), N, N-dimethylformamide, acetonitrile, butyl acetate；
The salting liquid of the water is：Sodium chloride, magnesium chloride, potassium chloride, calcium chloride etc. can improve 5- methylols
The inorganic salt solution of furfural distribution coefficient in diphasic system.
6. according to described in claim 1 it is a kind of by continuous extraction realize 5 hydroxymethyl furfural continuously synthesis
Method, it is characterised in that：Extractant is at least one in alcohol, ether, alkane or ketone.
The alcohol includes C1~C5Straight chain or straight-chain alkyl alcohol；
The ether includes glycol monoethyl ether, glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol two
Methyl ether, methyl-isobutyl ether, tetrahydrofuran；Ketone includes methyl iso-butyl ketone (MIBK), acetylacetone,2,4-pentanedione；
The alkane includes C6~C18Linear paraffin or cycloalkane.
7. the side that 5 hydroxymethyl furfural continuously synthesizes is realized by continuous extraction according to a kind of described in claim 2
Method, it is characterised in that：Reaction used catalyst is in slaine, solid acid catalyst or liquid acid catalyst
At least one.
The slaine is：CrCl2·xH2O, CrCl3·xH2O, CuCl, CuCl2·xH2O, AlCl3,
LaCl3·xH2O, FeCl3·xH2O, ZnCl2·xH2O, LiCl or SnCl4,；
The solid acid catalyst is：Acid MFI, AFI, Beta zeolite molecular sieve or acid phenolic resin；
The liquid acid is：Sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid or benzene sulfonic acid.
8. want a kind of described in 2 according to right and the side that 5 hydroxymethyl furfural continuously synthesizes is realized by continuous extraction
Method, it is characterised in that：Reaction temperature is 90-200 DEG C, and reaction pressure is 0.1--6MPa.
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Cited By (8)
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|---|---|---|---|---|
| CN107556271A (en) * | 2017-09-22 | 2018-01-09 | 厦门大学 | A kind of method that 5 hydroxymethylfurfurals are prepared with glucose |
| CN108727310A (en) * | 2018-06-29 | 2018-11-02 | 江苏大学 | A method of extracting 5 hydroxymethyl furfural using ionic liquid double-aqueous phase system |
| CN109180617A (en) * | 2018-09-17 | 2019-01-11 | 中国科学院广州能源研究所 | A kind of two-phase biomass pretreatment coproduction chemical processes based on Furnan products extractant |
| CN109364523A (en) * | 2018-11-16 | 2019-02-22 | 江苏大学 | A method of utilizing ionic liquid double-aqueous phase system extraction and separation 5 hydroxymethyl furfural and fructose |
| CN109810080A (en) * | 2017-11-20 | 2019-05-28 | 中国科学院大连化学物理研究所 | The method that 5 hydroxymethyl furfural efficiently synthesizes is realized by addition nitrogenous compound |
| CN112279758A (en) * | 2020-10-28 | 2021-01-29 | 中国科学院山西煤炭化学研究所 | Method for preparing and separating levulinic acid from glucose |
| CN112679454A (en) * | 2019-10-18 | 2021-04-20 | 中国石油化工股份有限公司 | Continuous preparation and purification method and device of 5-hydroxymethylfurfural |
| CN114874161A (en) * | 2022-04-22 | 2022-08-09 | 浙江恒逸石化研究院有限公司 | Method for continuously synthesizing and purifying 5-hydroxymethylfurfural by means of hollow fiber membrane tube |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107556271A (en) * | 2017-09-22 | 2018-01-09 | 厦门大学 | A kind of method that 5 hydroxymethylfurfurals are prepared with glucose |
| CN107556271B (en) * | 2017-09-22 | 2020-06-26 | 厦门大学 | Method for preparing 5-hydroxymethylfurfural from glucose |
| CN109810080A (en) * | 2017-11-20 | 2019-05-28 | 中国科学院大连化学物理研究所 | The method that 5 hydroxymethyl furfural efficiently synthesizes is realized by addition nitrogenous compound |
| CN108727310A (en) * | 2018-06-29 | 2018-11-02 | 江苏大学 | A method of extracting 5 hydroxymethyl furfural using ionic liquid double-aqueous phase system |
| CN109180617B (en) * | 2018-09-17 | 2020-12-04 | 中国科学院广州能源研究所 | Two-phase biomass pretreatment co-production chemical method based on furfural compound extractant |
| CN109180617A (en) * | 2018-09-17 | 2019-01-11 | 中国科学院广州能源研究所 | A kind of two-phase biomass pretreatment coproduction chemical processes based on Furnan products extractant |
| CN109364523A (en) * | 2018-11-16 | 2019-02-22 | 江苏大学 | A method of utilizing ionic liquid double-aqueous phase system extraction and separation 5 hydroxymethyl furfural and fructose |
| CN109364523B (en) * | 2018-11-16 | 2021-01-15 | 江苏大学 | Method for extracting and separating 5-hydroxymethylfurfural and fructose by using ionic liquid aqueous two-phase system |
| CN112679454A (en) * | 2019-10-18 | 2021-04-20 | 中国石油化工股份有限公司 | Continuous preparation and purification method and device of 5-hydroxymethylfurfural |
| CN112279758A (en) * | 2020-10-28 | 2021-01-29 | 中国科学院山西煤炭化学研究所 | Method for preparing and separating levulinic acid from glucose |
| CN112279758B (en) * | 2020-10-28 | 2022-02-25 | 中国科学院山西煤炭化学研究所 | Method for preparing and separating levulinic acid from glucose |
| CN114874161A (en) * | 2022-04-22 | 2022-08-09 | 浙江恒逸石化研究院有限公司 | Method for continuously synthesizing and purifying 5-hydroxymethylfurfural by means of hollow fiber membrane tube |
| CN114874161B (en) * | 2022-04-22 | 2024-02-02 | 浙江恒逸石化研究院有限公司 | Method for continuously synthesizing and purifying 5-hydroxymethylfurfural by means of hollow fiber membrane tube |
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