CN107011296B - The method for preparing 2,5- furans dicarbaldehyde using saccharide compound degradation - Google Patents
The method for preparing 2,5- furans dicarbaldehyde using saccharide compound degradation Download PDFInfo
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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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Abstract
The invention discloses the methods using saccharide compound degradation preparation 2,5-furandaldehyde, and saccharide compound, metal salt, peroxide agent and solvent are specifically added to reaction under high pressure and held in kettle, stirring forms homogeneous solution；It is passed through the mixed gas of carbon dioxide and oxygen immediately, 60~240min is reacted under the conditions of 120~180 DEG C, 1~5MPa, it can efficient catalytic saccharide compound dehydration preparation 2,5-furandaldehyde.The present invention has the advantages that selectivity is high, reaction speed is fast, simple process and at low cost；Furthermore it also avoids and corrodes equipment, the defect of acid solution exhaust emission environment using strong acid catalyst, the industrialization promotion for preparing 2,5-furandaldehyde for saccharide compound provides reliable technical support.
Description
[technical field]
The invention belongs to Industrial Catalysis and organic chemicals field, in particular to utilize saccharide compound degradation preparation 2,5-
The method of furans dicarbaldehyde.
[background technique]
Current platform compound is mainly obtained from petroleum resources, with a large amount of consumption of the non-renewable resources such as petroleum,
It will constantly be improved with the cost that petroleum is leading chemical engineering industry.Biomass is a kind of sustainability resource, enormous amount, valence
Lattice are cheap, biodegradable.It excavates renewable biomass resources and prepares Novel platform compound, be to solve current resource and energy
The important method of source crisis.Between 2005 to 2008 years, international top magazine Science and Nature follow-up story several
Biomass-based carbohydrate liquid fuel was prepared starts sex work, and people is caused to pay close attention to, and the focus point of these work is
5 hydroxymethyl furfural (HMF) is generated in catalyst action selectively dewatering by saccharide compound, then further refining is other
High level chemicals.HMF can be obtained by biomass materials catalytic dehydrations such as cheap, reproducible hexose, oligosaccharide, high glycans
It arrives, is a kind of important chemical intermediate, is considered as one kind in the world between biology base carbohydrate chemistry and petroleum-based chemical
Crucial bridge compound.Aldehyde radical and methylol are had on HMF molecule furan nucleus, can generate a series of furans with catalysis oxidation
Aromatic compound can be oxidized into 5- methylol -2- furancarboxylic acid (5- according to the position of oxidation and degree of oxidation
Hydroxymethylfuroic acid, HMFCA), 2,5-furandaldehyde (2,5-diformylfuran, DFF), 5- formyl
Base -2- furancarboxylic acid (5-formylfuroic acid, FFCA), 2,5-furandicarboxylic acid (2,5-furandicarboxylic
Acid, FDCA) etc. the platform chemicals based on furan nucleus.The structural formula of HMF oxidized derivatives is as follows:
In the oxidized derivatives of HMF, the market prospects of 2,5-furandaldehyde are the most wide, because of its typification with aldehyde
Property is learned, polymer monomer and drug and pesticide intermediate is can be used as, can be used for synthesizing fungicide, drug and functionality
Macromolecule etc. is used as a kind of row machine object list, can be used as the original of preparation about object intermediate, fungicide and nematicide, as heterocycle
Ligand is the ingredient of foundry sand binder as the crosslinking agent of polyethylene glycol in battery separators, in electrodeposit metal, is divided
The monomer analysed chemistry, the presoma of organic metal, electron-optical instrument, organic fluorescent powder and illuminator, synthesize multifunctional material
Etc. be widely used.2,5-furandaldehyde serves many purposes, and widely answers although 2,5-furandaldehyde has
With, but its commercial price is very expensive.So being that raw material preparation 2,5-furandaldehyde is ground very much from biomass saccharide compound
Study carefully value.
Currently, 2,5-furandaldehyde can be by being selectively oxidized preparation to HMF, detailed process needs first will more hold
Oxidizable aldehyde radical protects, then aoxidizes to hydroxyl.Original research personnel mainly directly adopt traditional oxidant
(KMnO4, NaClO etc.) aoxidized, but the oxidation reaction is selectively low.The d electronics of the noble metals such as Pd, Au, Pt, Ru, Rh
Track is all unfilled, the easy adsorption reaction object in surface, and moderate strength, is conducive to be formed intermediate " reactive compound ", with higher
Catalytic activity and reaction selectivity are widely used in the oxidation preparation 2,5-furandaldehyde of HMF.Nie Junfang etc. is in " catalysis
Journal ", 34 (2013): 871-875, deliver " Ru/C catalysis 5 hydroxymethyl furfural selective oxidation efficiently synthesize 2,5- furans two
Formaldehyde ", disclose realizes the oxidation of HMF high efficiency selected on activated carbon supported metal ruthenium catalyst, using toluene as reaction dissolvent,
In 383K and 2.0Mpa O2Reaction condition under, 2,5-furandaldehyde yield is up to 95.8%.Have with activated carbon supported
The Pt of similar partial size, Rh, other noble metal catalysts such as Pd, Au are compared, and Ru/C has more excellent activity and 2,5- furans
Dicarbaldehyde selectivity.It replaces toluene as solvent using water, while adding a small amount of hydrotalcite solid base, easily will can mainly produce
Object is tuned as FFCA or FFDA from 2,5-furandaldehyde, shows Ru/C catalyst in control 5 hydroxymethyl furfural selective oxidation
Excellent properties in terms of reaction product.
Since in the preparation process of HMF, effective solution is not yet received in separation and purification technique difficulty, cause it in phase
The research and industrial application for closing derivative are limited to a certain extent.Therefore directly by saccharide compound such as fructose, grape
The biomass such as sugar and sucrose become the effective way for solving the problems, such as this by " one kettle way " synthesis HMF oxidized derivatives, but
Raw material HMF separation is difficult thus expensive, so that the production cost is very high for 2,5-furandaldehyde.We use carbon hydrate
Object makees raw material, and one kettle way in-situ oxidation HMF obtains 2,5-furandaldehyde under temperate condition, avoids separation HMF, reduces cost,
Economically there is great advantage, and more meets the target of Green Chemistry.
[summary of the invention]
In order to overcome the problems of prior art, the present invention provides one kind with reproducible saccharide compound resource
For the method that raw material prepares 2,5-furandaldehyde, this method using high-pressure carbon dioxide and oxygen mixed gas, be aided with it is suitable
Measuring peroxide agent and metal salt is catalyst, and one kettle way in-situ oxidation HMF obtains 2,5-furandaldehyde in a mild condition,
Economically there is great advantage.
To solve the above problems, the technical scheme adopted by the invention is that: utilize saccharide compound degradation preparation 2,5- furan
The method for dicarbaldehyde of muttering, comprising the following steps: (1): according to parts by weight, by 3~30 parts of saccharide compounds, 0.5~16 part of mistake
Oxidant, 0.1~0.25 part of metal salt and 100 parts of solvents, are poured into autoclave, rapidly with 300r/min's after sealing
Revolving speed stirs evenly, and forms limpid solution；
(2): continuing to keep the mixing speed of 300r/min, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
Kettle makes 1~5MPa of pressure in kettle, then heats autoclave, makes temperature to 120~180 DEG C, after reacting 60~240min
Stop reaction, cooled to room temperature is the mixed liquor of primary product to get 2,5-furandaldehyde.
In the present invention, as further explanation, saccharide compound described in step (1) be fructose, sucrose, glucose sugar,
Any one in starch and cellulose.
In the present invention, as further explanation, metal salt described in step (1) be copper acetate, copper oxide, copper sulphate,
Any one in copper chloride, copper nitrate, copper carbonate, Kocide SD and cupric oxalate.
In the present invention, as further explanation, peroxide agent described in step (1) is the peroxide that mass fraction is 30%
Change aqueous solution of hydrogen, mass fraction is 5% potassium permanganate solution and mass fraction is any in 10% ammonium persulfate aqueous solution
It is a kind of.
In the present invention, as further explanation, solvent described in step (1) is 1,3-Dimethyl-2-imidazolidinone water
Solution.
In the present invention, as further explanation, in the mixed gas of carbon dioxide and oxygen described in step (2) two
The volume ratio of carbonoxide and oxygen is 3~4:1.
The invention has the following advantages:
1. the present invention is using the mixed gas of carbon dioxide and oxygen as major catalyst, under high-temperature and high-pressure conditions, two
The mixed gas of carbonoxide and oxygen has excellent acidity and oxidisability, saccharide compound efficient catalytic can be prepared 2,5-
Furans dicarbaldehyde avoids the defect needed during the reaction using liquid strong acid, and effectively improve consersion unit uses the longevity
Life.
2. the present invention, as cocatalyst, can increase oxidation efficiency and effectively improve using using mantoquita and potassium permanganate
The selectivity for generating 2,5-furandaldehyde is conducive to the yield for improving 2,5-furandaldehyde.
3. the present invention prepares 2,5-furandaldehyde using " one kettle way ", relatively traditional to aoxidize preparation 2,5- furan by HMF
Dicarbaldehyde of muttering approach, the present invention can remove many and diverse separating step of HMF from simultaneously, reduce cost, and more meet Green Chemistry
Target.
4. the present invention is using 1,3- dimethyl-imidazolinone aqueous solution as reaction dissolvent, 1,3- dimethyl -2- imidazoline
Ketone is higher boiling, intensive polar solvent, and can effectively increase catalysis reaction is rate.
[specific embodiment]
Embodiment 1:
Utilize the method for saccharide compound degradation preparation 2,5-furandaldehyde, comprising the following steps:
(1): being 5% potassium permanganate solution, 0.2 portion of vinegar by 4.5 parts of fructose, 0.5 part of mass fraction according to parts by weight
The 1,3-Dimethyl-2-imidazolidinone aqueous solution that sour copper and 100 parts of mass fractions are 80%, is poured into autoclave, fast
It is stirred evenly after speed sealing with the revolving speed of 300r/min, forms limpid solution；
(2): continuing to keep the mixing speed of 300r/min, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
Kettle, wherein the volume ratio of the carbon dioxide and oxygen in the mixed gas of carbon dioxide and oxygen is 4:1, makes pressure in kettle
5MPa then heats autoclave, makes temperature to 160 DEG C, stops reacting after reacting 100min, cooled to room temperature, i.e.,
Obtain the mixed liquor that 2,5-furandaldehyde is primary product.
Analyzed with high performance liquid chromatography product, obtain following result: fructose converting rate is 97.27%, 2,5-
Furans dicarbaldehyde yield is 40.25%.
Embodiment 2:
Utilize the method for saccharide compound degradation preparation 2,5-furandaldehyde, comprising the following steps:
(1): according to parts by weight, by 7.5 portions of sucrose, 10 parts be mass fraction be 30% aqueous hydrogen peroxide solution, 0.1
The 1,3-Dimethyl-2-imidazolidinone aqueous solution that part copper oxide and 100 parts of mass fractions are 80%, pours into autoclave
In, it is stirred evenly after sealing with the revolving speed of 300r/min rapidly, forms limpid solution；
(2): continuing to keep the mixing speed of 300r/min, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
Kettle, wherein the volume ratio of the carbon dioxide and oxygen in the mixed gas of carbon dioxide and oxygen is 3.5:1, makes pressure in kettle
3MPa then heats autoclave, makes temperature to 180 DEG C, stops reacting after reacting 120min, cooled to room temperature, i.e.,
Obtain the mixed liquor that 2,5-furandaldehyde is primary product.
Product is analyzed with high performance liquid chromatography, obtains following result: Sucrose conversion 93.27%, 2,5-
Furans dicarbaldehyde yield is 23.22%.
Embodiment 3:
Utilize the method for saccharide compound degradation preparation 2,5-furandaldehyde, comprising the following steps:
(1): being 10% ammonium persulfate aqueous solution, 0.25 part by 15 portions of glucose sugar, 4 parts of mass fractions according to parts by weight
The 1,3-Dimethyl-2-imidazolidinone aqueous solution that cupric oxalate and 100 parts of mass fractions are 80%, is poured into autoclave,
It is stirred evenly after sealing with the revolving speed of 300r/min rapidly, forms limpid solution；
(2): continuing to keep the mixing speed of 300r/min, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
Kettle, wherein the volume ratio of the carbon dioxide and oxygen in the mixed gas of carbon dioxide and oxygen is 3:1, makes pressure in kettle
2.5MPa then heats autoclave, makes temperature to 150 DEG C, stops reacting after reacting 60min, cooled to room temperature, i.e.,
Obtain the mixed liquor that 2,5-furandaldehyde is primary product.
Product is analyzed with high performance liquid chromatography, obtains following result: inversion rate of glucose 87.72%, 2,
5- furans dicarbaldehyde yield is 15.25%.
Embodiment 4:
Utilize the method for saccharide compound degradation preparation 2,5-furandaldehyde, comprising the following steps:
(1): according to parts by weight, by 22.5 parts of starch, the aqueous hydrogen peroxide solution that 16 parts of mass fractions are 30%, 0.15
The 1,3-Dimethyl-2-imidazolidinone aqueous solution that part Kocide SD and 100 parts of mass fractions are 80%, pours into autoclave
In, it is stirred evenly after sealing with the revolving speed of 300r/min rapidly, forms limpid solution；
(2): continuing to keep the mixing speed of 300r/min, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
Kettle, wherein the volume ratio of the carbon dioxide and oxygen in the mixed gas of carbon dioxide and oxygen is 4:1, makes pressure in kettle
2MPa then heats autoclave, makes temperature to 120 DEG C, stops reacting after reacting 240min, cooled to room temperature, i.e.,
Obtain the mixed liquor that 2,5-furandaldehyde is primary product.
Product is analyzed with high performance liquid chromatography, obtains following result: Starch Conversion rate 79.24%, 2,5-
Furans dicarbaldehyde yield is 10.50%.
Embodiment 5:
Utilize the method for saccharide compound degradation preparation 2,5-furandaldehyde, comprising the following steps:
(1): being 5% potassium permanganate solution, 0.25 part by 30 parts of celluloses, 1.5 parts of mass fractions according to parts by weight
The 1,3-Dimethyl-2-imidazolidinone aqueous solution that copper sulphate and 100 parts of mass fractions are 80%, is poured into autoclave,
It is stirred evenly after sealing with the revolving speed of 300r/min rapidly, forms limpid solution；
(2): continuing to keep the mixing speed of 300r/min, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
Kettle, wherein the volume ratio of the carbon dioxide and oxygen in the mixed gas of carbon dioxide and oxygen is 4:1, makes pressure in kettle
5MPa then heats autoclave, makes temperature to 180 DEG C, stops reacting after reacting 180min, cooled to room temperature, i.e.,
Obtain the mixed liquor that 2,5-furandaldehyde is primary product.
Product is analyzed with high performance liquid chromatography, obtain following result: cellulose conversion ratio is 77.48%, 2,
5- furans dicarbaldehyde yield is 11.85%.
Embodiment 6:
Utilize the method for saccharide compound degradation preparation 2,5-furandaldehyde, comprising the following steps:
(1): being 5% potassium permanganate solution, 0.2 part of nitre by 6 parts of fructose, 0.75 part of mass fraction according to parts by weight
The 1,3-Dimethyl-2-imidazolidinone aqueous solution that sour copper and 100 parts of mass fractions are 80%, is poured into autoclave, fast
It is stirred evenly after speed sealing with the revolving speed of 300r/min, forms limpid solution；
(2): continuing to keep the mixing speed of 300r/min, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
Kettle, wherein the volume ratio of the carbon dioxide and oxygen in the mixed gas of carbon dioxide and oxygen is 3:1, makes pressure in kettle
3.5MPa then heats autoclave, makes temperature to 140 DEG C, stops reacting after reacting 160min, cooled to room temperature,
It is the mixed liquor of primary product up to 2,5-furandaldehyde.
Analyzed with high performance liquid chromatography product, obtain following result: fructose converting rate is 94.23%, 2,5-
Furans dicarbaldehyde yield is 32.47%.
Embodiment 7:
Utilize the method for saccharide compound degradation preparation 2,5-furandaldehyde, comprising the following steps:
(1): being 10% ammonium persulfate aqueous solution, 0.15 part by 3 portions of glucose sugar, 2.5 parts of mass fractions according to parts by weight
The 1,3-Dimethyl-2-imidazolidinone aqueous solution that copper chloride and 100 parts of mass fractions are 80%, is poured into autoclave,
It is stirred evenly after sealing with the revolving speed of 300r/min rapidly, forms limpid solution；
(2): continuing to keep the mixing speed of 300r/min, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
Kettle, wherein the volume ratio of the carbon dioxide and oxygen in the mixed gas of carbon dioxide and oxygen is 3:1, makes pressure in kettle
1MPa then heats autoclave, makes temperature to 160 DEG C, stops reacting after reacting 220min, cooled to room temperature, i.e.,
Obtain the mixed liquor that 2,5-furandaldehyde is primary product.
Product is analyzed with high performance liquid chromatography, obtains following result: inversion rate of glucose 84.28%, 2,
5- furans dicarbaldehyde yield is 20.64%.
Embodiment 8:
Utilize the method for saccharide compound degradation preparation 2,5-furandaldehyde, comprising the following steps:
(1): being 5% potassium permanganate solution, 0.2 part of carbonic acid by 4.5 portions of sucrose, 1 part of mass fraction according to parts by weight
The 1,3-Dimethyl-2-imidazolidinone aqueous solution that copper and 100 parts of mass fractions are 80%, is poured into autoclave, rapidly
It is stirred evenly after sealing with the revolving speed of 300r/min, forms limpid solution；
(2): continuing to keep the mixing speed of 300r/min, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
Kettle, wherein the volume ratio of the carbon dioxide and oxygen in the mixed gas of carbon dioxide and oxygen is 4:1, makes pressure in kettle
4.5MPa then heats autoclave, makes temperature to 120~180 DEG C, stops reaction after reacting 60~240min, naturally cold
It but is the mixed liquor of primary product to get 2,5-furandaldehyde to room temperature.
Product is analyzed with high performance liquid chromatography, obtains following result: Sucrose conversion 89.25%, 2,5-
Furans dicarbaldehyde yield is 27.54%.
Above description is the detailed description for the present invention preferably possible embodiments, but embodiment is not limited to this hair
Bright patent claim, it is all the present invention suggested by technical spirit under completed same changes or modifications change, should all belong to
In the covered the scope of the patents of the present invention.
Claims (3)
1. utilizing the method for saccharide compound degradation preparation 2,5-furandaldehyde, it is characterised in that: the following steps are included:
(1): according to parts by weight, the aquae hydrogenii dioxidi for being 30% by 3~30 parts of saccharide compounds, 0.5~16 part of mass fraction
Solution, 0.1~0.25 part of metal salt and 100 parts of 1,3-Dimethyl-2-imidazolidinone aqueous solutions, are poured into autoclave,
It is stirred evenly after sealing with the revolving speed of 300r/min rapidly, forms limpid solution；
The metal salt is any one in copper acetate, copper sulphate, copper chloride, copper nitrate, copper carbonate and cupric oxalate；
(2): continue to keep the mixing speed of 300r/min, the mixed gas of carbon dioxide and oxygen is passed through autoclave,
Make 1~5MPa of pressure in kettle, then heat autoclave, make temperature to 120~180 DEG C, stops after reacting 60~240min
It only reacts, cooled to room temperature is the mixed liquor of primary product to get 2,5-furandaldehyde.
2. the method according to claim 1 using saccharide compound degradation preparation 2,5-furandaldehyde, feature exist
In: saccharide compound described in step (1) is any one in fructose, sucrose, glucose, starch and cellulose.
3. the method according to claim 1 using saccharide compound degradation preparation 2,5-furandaldehyde, feature exist
In: the volume ratio of the carbon dioxide and oxygen in the mixed gas of carbon dioxide and oxygen described in step (2) is 3~4:1.
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