CN109942518A - A method of one pot of slave biomass resource of no metal participation prepares 5 methyl furfural - Google Patents
A method of one pot of slave biomass resource of no metal participation prepares 5 methyl furfural Download PDFInfo
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Abstract
The present invention relates to catalysis technical fields, more particularly to a kind of one pot of method for preparing 5 methyl furfural of slave biomass resource that no metal participates in, as follows: biomass or derivatives thereof, iodide, solvent, acid being successively added to high-temperature high-pressure reaction kettle, and it is passed through certain hydrogen, reaction is after a certain period of time, after collect organic phase fractionation 5 methyl furfural can be obtained, yield is up to 51.9%.This method is of less demanding to production equipment by under the conditions of low-temp low-pressure, meets the principle of safety in production；No metal participates in selective hydrogenolysis biomass or derivatives thereof conversion 5 methyl furfural, raw material it is renewable it is at low cost, cyclicity is good, simple process, mild condition and product are easily separated, and avoids intermediate steps bring loss of material, realize maximally utilizing for resource.
Description
Technical field
The invention belongs to catalysis technical fields, are related to a kind of one pot of preparation 5- methyl of slave biomass resource that no metal participates in
The method of furfural.
Background technique
Biomass is unique sustainable origin of organic carbon on the current earth, is the reason for producing fuel, chemicals and material
Think oil substitutes.But the structure of most of organism-based raw material complexity and chemically restrict its large-scale application.Biomass is fine
Dimension element and starch be all by glucose group at macromolecular polysaccharide it is widely distributed in nature, account for the 50% of plant kingdom's carbon content
More than.It is abundant in nature content of starch, it is present in the staple foods such as potato, wheat, corn, rice and cassava, is human diet
In the most common organism-based raw material.Glucose and fructose are the most common hexoses of nature, downstream derivative 5- methylol chaff
Aldehyde is considered as most potential biology base plateform molecules compound.5 methyl furfural (5-MF) is 5 hydroxymethyl furfural (HMF)
Deoxidation hydrogenation products, and a kind of important fine chemicals is widely used in the industries such as medicine, pesticide, cosmetics, still
A kind of important composition of general flavorant, or even it is also considered to be a kind of important anticancer drug.In addition, it is also used as
The important intermediate of recyclable fuel.
The synthetic method of industrial 5 methyl furfural at present: Japan Patent JPS5791982A report a kind of phosgene first with
2- methylfuran is reacted with the mixture of n,N-Dimethylformamide, and gained reaction product water solution is then obtained 5 methyl furfural
Method.Industrially large-scale application produces 5 methyl furfural to this method.But there is many drawbacks for the method: 1. raw materials come
It is non-renewable derived from petrochemical industry.2. expensive starting materials.3. phosgene is harmful to the human body.
It is reported in the literature to prepare the method for 5 methyl furfural mainly include the following types: 1.Mascal etc. is utilized from biomass
Microcrystalline cellulose is converted into 5- chloromethyl furfural under the conditions of lithium chloride and concentrated hydrochloric acid, then again through palladium chloride in atmosphere of hydrogen
Catalytic hydrogenolysis obtains 5 methyl furfural (Angew.Chem.2008,120,8042-8044).2.Yang etc. is used under an atmosphere of hydrogen
RhCl3With HI be catalyzed glucose and it is fructose converting for its yield of 5 methyl furfural up to 68% (ChemSusChem2011,4,
349-352).3. Chinese patent CN102766119A discloses a kind of fructose based biomass progress heat under acid catalyst catalysis
Solution obtains the bio oil containing 20% molar yield 5 methyl furfural.
It include: the dehydration product that 5 hydroxymethyl furfural is hexose from biomass derivatives synthetic method, in recent years constantly
Someone studies the method for preparing 5 methyl furfural from 5 hydroxymethyl furfural.Huang in 2014 etc. is using HMF as raw material W2C/AC is to urge
Agent obtains the 5-MF of 87.1% yield in 200 DEG C of reaction 3h in hydrogen and THF system.Li et al. in 2017 is with heterogeneous iron
Catalyst be catalyzed in hydrogen and THF single_phase system HMF obtain 22.1% yield 5-MF (ChemSusChem2017,10,
1436–1447).The same year Chinese patent CN107353268A reports one kind with Pd-PVP/ZrO2For catalyst, it is with formic acid
Hydrogen source catalysis 5 hydroxymethyl furfural in tetrahydrofuran (THF) is converted into the method for 5 methyl furfural and obtains 86% mole production
Rate.But all there is the problems such as expensive catalyst, complex process, condition is harsh, and cyclicity is poor in approach described above.For this purpose, we
It is badly in need of that a kind of catalyst is cheap, and reaction condition is mild, the method for quickly preparing 5 methyl furfural of simple process.
Summary of the invention
The purpose of the present invention is preparing expensive catalyst present in the technology of 5 methyl furfural for solution is existing, technique is multiple
The disadvantages of miscellaneous, the present invention provide a kind of method that the slave biomass that no metal participates in prepares 5 methyl furfural.
The present invention is achieved by the following technical solutions, and steps are as follows:
Biomass or derivatives thereof, iodide, solvent, acid are successively added to high-temperature high-pressure reaction kettle, and are passed through certain
Hydrogen.Reaction after a certain period of time, after collect organic phase fractionation 5 methyl furfural can be obtained.Reaction equation is as follows:
Further, the biomass or its Yan Sheng Wu ︰ iodide molar ratio are 0.01~100；Biomass or its derivative
Wu ︰ solvent quality ratio is 0.001-100；Rong Ji ︰ acid volume ratio is 10~1000；Reaction temperature is 50~300 DEG C, preferably
120~200 DEG C；Hydrogen Vapor Pressure is 10~1000psi, preferably 100~500psi；Reaction time be 0.1~for 24 hours, preferably 1
~12h.
Further, the biomass and its derivative include: lignocellulose-like biomass, cellulose, starch, chrysanthemum
Or mixtures thereof powder, sucrose, maltose, glucose, fructose and 5 hydroxymethyl furfural (HMF),.
Further, the acid is hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydroiodic acid, hydrobromic acid, perchloric acid, acetic acid, 3- fluorine
It benzene sulfonic acid, formic acid and is supported on active carbon, zirconium dioxide, titanium dioxide, silica, aluminum oxide or molecular sieve carrier
Solid acid catalyst, or mixtures thereof.
Further, the iodide include: sodium iodide, potassium iodide, lithium iodide, hydrogen iodide, iodate rhodium, palladium iodide, iodine
Or mixtures thereof change ruthenium and platinum diiodide,.
Further, the solvent include water, benzene, toluene, chlorobenzene, furans, tetrahydrofuran, 2- methyltetrahydrofuran,
Or mixtures thereof 2,5- dimethyl-tetrahydrofuran, hexone, six alkane of 1,4- epoxy, hexamethylene and n-hexane,.
Compared with prior art, the beneficial effects of the present invention are:
(1) one pot of 5 methyl furfural processed of biomass or derivatives thereof, streamline operation avoid intermediate steps bring object
Material loss, realizes maximally utilizing for resource.(2) present invention need to only carry out under low temperature, lower pressure, to production equipment requirement
It is not high, meet the principle of safety in production.(3) using common biomass as raw material, non-metal catalyst can be recycled the present invention,
Product is easily separated to be convenient for industrial application.
Specific embodiment
Below in conjunction with the embodiment of the present invention, technical scheme in the embodiment of the invention is clearly and completely described,
Obviously, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Based in the present invention
Embodiment, every other embodiment obtained by those of ordinary skill in the art without making creative efforts, all
Belong to the scope of protection of the invention.
Embodiment 1
Sequentially added in 50mL high-temperature high-pressure reaction kettle 100mg starch, 2mmol sodium iodide, 2ml water,
0.18mmolHCl (37wt%), 5ml2- methyltetrahydrofuran seal reaction kettle, are filled with hydrogen (300psi), stir and quick
160 DEG C are heated to, 2h is kept.Reaction kettle ice-water bath is cooled to room temperature, organic phase is collected and detects 2- methyl furan in its product
The yield muttered is 4.9%, and the yield of furfural is 1.9%, and the yield of 5 methyl furfural is 37.7%, gross production rate 44.5%.
The detection of 5 methyl furfural yield and calculation basis following methods carry out:
Quantitative analysis using gas chromatograph Agilent 7820A series (fid detector, AgilentHP-5 chromatographic column:
30m*32um*0.25um).Qualitative analysis uses gaseous mass analyzer ThermoscientificTRACE1310 (HP-5 capillary chromatography
30m*320 μm * 0.25 μm of column).
5 methyl furfural calculation of yield formula；
5 methyl furfural yield=(mole of glucose in 5 methyl furfural mole/biomass in organic phase) ×
100%
Embodiment 2
Sequentially added in 50mL high-temperature high-pressure reaction kettle 100mg starch, 4mmol sodium iodide, 2ml water,
0.18mmolH2SO4, 3ml furans, stir and quickly heat up to 160 DEG C, keep 2h.Reaction kettle ice-water bath is cooled to room temperature, is received
Collection organic phase and the yield for detecting 2- methylfuran in its product are 4.8%, and the yield of furfural is 2.1%, 5 methyl furfural
Yield is 34.3%, gross production rate 41.2%.
Embodiment 3
Sequentially added in 50mL high-temperature high-pressure reaction kettle 100mg starch, 2mmol sodium iodide, 2ml water,
0.18mmolCF3SO3H, 3ml2- methyltetrahydrofuran seals reaction kettle, is filled with hydrogen (300psi), stirs and quickly heat up to
160 DEG C, keep 2h.Reaction kettle ice-water bath is cooled to room temperature, collects organic phase through gas chromatographic detection, 2- methyl in product
The yield of furans is 1.9%, and the yield of furfural is 1.6%, and the yield of 5 methyl furfural is 29.0%, gross production rate 31.5%.
Embodiment 4
Sequentially added in 50mL high-temperature high-pressure reaction kettle 100mg glucose, 2mmol sodium iodide, 2ml water,
0.18mmolHI (57wt%), 3ml hexamethylene seal reaction kettle, are filled with hydrogen (200psi), stir and quickly heat up to 160
DEG C, keep 2h.Reaction kettle ice-water bath is cooled to room temperature, organic phase is collected and detects the yield of 2- methylfuran in its product and be
2.4%, the yield of 5 methyl furfural is 32.5%, gross production rate 34.9%.
Embodiment 5
Sequentially added in 50mL high-temperature high-pressure reaction kettle 100mg fructose, 2mmol sodium iodide, 2ml water,
0.18mmolHCl (37wt%), 3ml hexone seal reaction kettle, are filled with hydrogen (200psi) and stir and quickly add
Heat keeps 2h to 160 DEG C.Reaction kettle ice-water bath is cooled to room temperature, organic phase is collected and is detected, 2- methyl furan in product
The yield muttered is 3.1%, and the yield of 5 methyl furfural is 31.2%, gross production rate 34.3%.
Embodiment 6
Sequentially added in 50mL high-temperature high-pressure reaction kettle 0.5mmolHMF, 0.18mlHCl (37wt%), 2mmolNaI,
3ml2- methyltetrahydrofuran seals reaction kettle, is filled with hydrogen (300psi), stirs and quickly heats up to 160 DEG C, holding 2h.
Reaction kettle ice-water bath is cooled to room temperature, collecting organic phase and detecting the yield of 5 methyl furfural in its product is 51.9%, 2,
The yield of 5- diformyl furans is 35.6%, gross production rate 87.5%.
Embodiment 7
Sequentially added in 50mL high-temperature high-pressure reaction kettle 100mg starch, 2mmol sodium iodide, 2ml water,
0.18mmolHCl (37wt%), 3ml normal octane seal reaction kettle, are filled with hydrogen (100psi), stir and quickly heat up to 180
DEG C, keep 1h.Reaction kettle ice-water bath is cooled to room temperature, organic phase is collected and is detected, the yield of 2- methylfuran in product
It is 4.2%, the yield of furfural is 1.6%, and the yield of 5 methyl furfural is 10.1%, gross production rate 15.9%.
Embodiment 8
Sequentially added in 50mL high-temperature high-pressure reaction kettle 100mg starch, 2mmol potassium iodide, 2ml water,
0.18mmolHCl (37wt%), 3ml toluene seal reaction kettle, are filled with hydrogen (500psi), stir and quickly heat up to 160
DEG C, keep 2h.Reaction kettle ice-water bath is cooled to room temperature, organic phase is collected and is detected, the yield of 2- methylfuran in product
It is 2.5%, the yield of furfural is 2.3%, and the yield of 5 methyl furfural is 36.5%, gross production rate 41.3%.
Embodiment 9
Sequentially added in 50mL high-temperature high-pressure reaction kettle 100mg inulin, 4mmol lithium iodide, 2ml water,
0.18mmolHCl (37wt%), 3ml toluene seal reaction kettle, are filled with hydrogen (500psi), stir and quickly heat up to 160
DEG C, keep 2h.Reaction kettle ice-water bath is cooled to room temperature, organic phase is collected and is detected, the yield of 2- methylfuran in product
It is 1.7%, the yield of furfural is 1.3%, and the yield of 5 methyl furfural is 38.5%, gross production rate 41.5%.
Embodiment 10
1.0mmol maltose, 2mmol hydrogen iodide, 1ml water, 3ml 2 are sequentially added in 50mL high-temperature high-pressure reaction kettle,
5- dimethyl-tetrahydrofuran seals reaction kettle, is filled with hydrogen (500psi), stirs and quickly heats up to 150 DEG C, holding 2h.It will
Reaction kettle ice-water bath is cooled to room temperature, and is collected organic phase and is detected, and the yield of 2- methylfuran is 3.7%, 5- first in product
The yield of base furfural is 42.5%, gross production rate 46.2%.
Claims (9)
1. a kind of one pot of method for preparing 5 methyl furfural of slave biomass resource that no metal participates in, it is characterized in that by following step
It is rapid: biomass or derivatives thereof, iodide, solvent, acid are successively added to high-temperature high-pressure reaction kettle, and are passed through certain hydrogen,
Reaction after a certain period of time, after collect organic phase fractionation 5 methyl furfural can be obtained.
2. the side that a kind of participate in one pot of slave biomass resource of no metal according to claim 1 prepares 5 methyl furfural
Method, characterized in that described biomass or derivatives thereof: iodide molar ratio is 0.01~100；Biomass or derivatives thereof: molten
Agent mass ratio is 0.001-100；Solvent: sour volume ratio is 10~1000；Reaction temperature is 50~300 DEG C, Hydrogen Vapor Pressure 10
~1000psi, the reaction time be 0.1~for 24 hours.
3. one pot of slave biomass resource of a kind of no metal participation according to claim 1 or 2 prepares 5 methyl furfural
Method, the biomass and its derivative include: lignocellulose-like biomass, cellulose, starch, inulin, sucrose, malt
Or mixtures thereof sugar, glucose, fructose and 5 hydroxymethyl furfural (HMF),.
4. one pot of slave biomass resource of a kind of no metal participation according to claim 1 or 2 prepares 5 methyl furfural
Method, it is characterized in that the reaction temperature is 120~200 DEG C.
5. one pot of slave biomass resource of a kind of no metal participation according to claim 1 or 2 prepares 5 methyl furfural
Method, it is characterized in that the pressure limit of the hydrogen is 100~500psi.
6. one pot of slave biomass resource of a kind of no metal participation according to claim 1 or 2 prepares 5 methyl furfural
Method, it is characterized in that the time of the reaction is 1~12h.
7. one pot of slave biomass resource of a kind of no metal participation according to claim 1 or 2 prepares 5 methyl furfural
Method, it is characterized in that the acid is hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydroiodic acid, hydrobromic acid, perchloric acid, acetic acid, 3- fluorobenzene sulphur
Acid and is supported on consolidating on active carbon, zirconium dioxide, titanium dioxide, silica, aluminum oxide or molecular sieve carrier at formic acid
One of body acid catalyst is a variety of.
8. one pot of slave biomass resource of a kind of no metal participation according to claim 1 or 2 prepares 5 methyl furfural
Method, it is characterized in that the iodide are sodium iodide, potassium iodide, lithium iodide, hydrogen iodide, iodate rhodium, palladium iodide, iodate ruthenium and iodine
Change one of platinum or a variety of.
9. one pot of slave biomass resource of a kind of no metal participation according to claim 1 or 2 prepares 5 methyl furfural
Method, it is characterized in that the solvent is water, benzene, toluene, chlorobenzene, furans, tetrahydrofuran, 2- methyltetrahydrofuran, 2,5- bis-
One of methyltetrahydrofuran, hexone, six alkane of Isosorbide-5-Nitrae-epoxy, hexamethylene, n-hexane are a variety of.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112939754A (en) * | 2021-02-03 | 2021-06-11 | 南昌大学 | Method for catalyzing alcohol disproportionation by iodine |
| CN115745923A (en) * | 2021-09-02 | 2023-03-07 | 中国科学院大连化学物理研究所 | Method for preparing 5-methylfurfural |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112939754A (en) * | 2021-02-03 | 2021-06-11 | 南昌大学 | Method for catalyzing alcohol disproportionation by iodine |
| CN112939754B (en) * | 2021-02-03 | 2023-05-02 | 南昌大学 | Method for disproportionating alcohol by iodine catalysis |
| CN115745923A (en) * | 2021-09-02 | 2023-03-07 | 中国科学院大连化学物理研究所 | Method for preparing 5-methylfurfural |
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