CN107011296A - The method for 2,5 furans dicarbaldehydes of preparation of being degraded using saccharide compound - Google Patents
The method for 2,5 furans dicarbaldehydes of preparation of being degraded using saccharide compound Download PDFInfo
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- CN107011296A CN107011296A CN201710284969.XA CN201710284969A CN107011296A CN 107011296 A CN107011296 A CN 107011296A CN 201710284969 A CN201710284969 A CN 201710284969A CN 107011296 A CN107011296 A CN 107011296A
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- saccharide compound
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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
Abstract
The method for preparing 2,5 furans dicarbaldehydes the invention discloses being degraded using saccharide compound, is specifically that saccharide compound, metal salt, peroxide agent and solvent are added into reaction under high pressure to hold in kettle, stirring forms homogeneous solution；The mixed gas of carbon dioxide and oxygen is passed through immediately, and 60~240min is reacted under the conditions of 120~180 DEG C, 1~5MPa, can efficient catalytic saccharide compound dehydration 2,5 furans dicarbaldehydes of preparation.The present invention has the advantages that selectivity is high, reaction speed is fast, technique is simple and cost is low；In addition it also avoid using strong acid catalyst etching apparatus, the defect of acid solution exhaust emission environment, be that saccharide compound prepares the Industry Promotion of 2,5 furans dicarbaldehydes there is provided reliable technical support.
Description
【Technical field】
The invention belongs to Industrial Catalysis and organic chemicals field, more particularly to 2,5- are prepared using saccharide compound degraded
The method of furans dicarbaldehyde.
【Background technology】
Current platform compound is mainly obtained from petroleum resources, with a large amount of consumption of the non-renewable resources such as oil,
To constantly it be improved using the cost of oil as leading chemical engineering industry.Biomass is a kind of sustainability resource, enormous amount, valency
Lattice are cheap, biodegradable.Excavate renewable biomass resources and prepare Novel platform compound, be to solve current resource and energy
The important method of source crisis.Between 2005 to 2008 years, several of international top magazine Science and Nature follow-up stories
What biomass-based carbohydrate prepared liquid fuel starts sex work, causes people to pay close attention to, the focus point of these work is
By saccharide compound in catalyst action selectively dewatering generation 5 hydroxymethyl furfural (HMF), then further refining is other
High level chemicals.HMF can be obtained by biomass material catalytic dehydrations such as cheap, reproducible hexose, oligosaccharide, high glycans
Arrive, be a kind of important chemical intermediate, be considered as one kind in the world between bio-based carbohydrate chemistry and petroleum-based chemical
Crucial bridge compound.Aldehyde radical and methylol are carried on HMF molecule furan nucleus, a series of furans can be generated with catalysis oxidation
Aromatic compound, according to the position of oxidation and degree of oxidation, can be oxidized into 5- methylol -2- furancarboxylic acids (5-
Hydroxymethylfuroic acid, HMFCA), DFF (2,5-diformylfuran, DFF), 5- formyls
Base -2- furancarboxylic acids (5-formylfuroic acid, FFCA), FDCA (2,5-furandicarboxylic
Acid, FDCA) etc. the platform chemicals based on furan nucleus.The structural formula of HMF oxidized derivatives is as follows：
In HMF oxidized derivatives, the market prospects of DFF are the most wide, because it has the typification of aldehyde
Property is learned, synthesizing fungicide, medicine and feature can be can be used for as polymer monomer and medicine and pesticide intermediate
Macromolecule etc. can be used as heterocycle as a kind of row machine thing list as the original for preparing about thing intermediate, bactericide and nematicide
Part, is the composition of foundry sand binding agent as the crosslinking agent of polyethylene glycol in battery separators, in electrodeposit metal, is divided
Analyse chemistry, the presoma of organic metal, electron-optical apparatus, organic fluorescent powder and illuminator, synthesize the monomer of multifunctional material
In terms of be widely used.DFF serves many purposes, although DFF, which has, widely should
With, but its commercial price is very expensive.So, prepare DFF for raw material from biomass saccharide compound and grind very much
Study carefully value.
At present, DFF can be by being selectively oxidized preparation to HMF, and detailed process needs first will more hold
Oxidizable aldehyde radical is protected, then hydroxyl is aoxidized.Original research personnel, which are mainly, directly uses 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 thing in surface, and moderate strength, in the middle of being formed " reactive compound ", with higher
Catalytic activity and reaction selectivity, the oxidation for being widely used in HMF prepare DFF.Nie Junfang etc. exists《Catalysis
Journal》, 34 (2013)：871-875, deliver《Ru/C catalysis 5 hydroxymethyl furfural selective oxidations efficiently synthesize 2,5- furans two
Formaldehyde》, disclose realizes the oxidation of HMF high efficiency selecteds on activated carbon supported metal ruthenium catalyst, using toluene as reaction dissolvent,
In 383K and 2.0Mpa O2Reaction condition under, DFF high income is up to 95.8%.Have with activated carbon supported
Other noble metal catalysts such as the Pt of similar particle diameter, Rh, Pd, Au are compared, and Ru/C has more excellent active and 2,5- furans
Dicarbaldehyde selectivity.Replace toluene as solvent using water, while adding a small amount of hydrotalcite solid base, easily will can mainly produce
Thing is tuned as FFCA or FFDA from DFF, shows Ru/C catalyst in control 5 hydroxymethyl furfural selective oxidation
Excellent properties in terms of reaction product.
Because in HMF preparation process, it is separated and purification technique difficulty is not yet effectively solved, and causes 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, synthesizing HMF oxidized derivatives by " one kettle way " becomes the effective way of the solution problem, but
Raw material HMF separation is difficult thus expensive so that the production cost of DFF is very high.We use carbon hydrate
Thing makees one kettle way in-situ oxidation HMF under raw material, temperate condition and obtains DFF, it is to avoid separation HMF, reduces cost,
Economically there is great advantage, and more meet the target of Green Chemistry.
【The content of the invention】
In order to overcome the problems of prior art, the invention provides one kind with reproducible saccharide compound resource
The method that DFF is prepared for raw material, this method using high-pressure carbon dioxide and oxygen mixed gas, be aided with it is suitable
It is catalyst to measure peroxide agent and metal salt, and one kettle way in-situ oxidation HMF obtains DFF in a mild condition,
Economically there is great advantage.
To solve the above problems, the technical solution adopted in the present invention is：2,5- furans are prepared using saccharide compound degraded
The method for dicarbaldehyde of muttering, comprises the following steps：(1)：Count 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, with 300r/min's after rapid sealing
Rotating speed stirs, and forms limpid solution；
(2)：Continue holding 300r/min mixing speed, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
Kettle, it is 1~5MPa to make pressure in kettle, is subsequently heated autoclave, makes temperature to 120~180 DEG C, after 60~240min of reaction
Stop reaction, naturally cool to room temperature, produce the mixed liquor that DFF is primary product.
In the present invention, as further illustrating, the saccharide compound described in step (1) is fructose, sucrose, glucose are sugared,
Any one in starch and cellulose.
In the present invention, as further illustrating, the metal salt described in step (1) be copper acetate, cupric oxide, copper sulphate,
Any one in copper chloride, copper nitrate, copper carbonate, Kocide SD and cupric oxalate.
In the present invention, as further illustrating, the peroxide agent described in step (1) is the peroxide that mass fraction is 30%
Change that aqueous solution of hydrogen, mass fraction are 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 illustrating, the solvent described in step (1) is DMI water
Solution.
In the present invention, as further illustrating, two in the mixed gas of the carbon dioxide and oxygen described in step (2)
The volume ratio of carbonoxide and oxygen is 3~4：1.
The invention has the advantages that：
1. the present invention is used as major catalyst, under high-temperature and high-pressure conditions, two using the mixed gas of carbon dioxide and oxygen
The mixed gas of carbonoxide and oxygen has excellent acidity and oxidisability, can be prepared by saccharide compound efficient catalytic into 2,5-
Furans dicarbaldehyde, it is to avoid need to use the defect of liquid strong acid during the course of the reaction, effectively improve the use longevity of consersion unit
Life.
2. the present invention, as cocatalyst, can increase oxidation efficiency and effectively improve using using mantoquita and potassium permanganate
The selectivity of DFF is generated, is conducive to improving the yield of DFF.
3. the present invention prepares DFF using " one kettle way ", relatively conventional to prepare 2,5- furans by HMF oxidations
Dicarbaldehyde of muttering approach, the present invention can remove the numerous and diverse separating steps of HMF from simultaneously, reduce cost, and more meet Green Chemistry
Target.
4. the present invention uses 1, the 3- dimethyl-imidazolinones aqueous solution as reaction dissolvent, 1,3- dimethyl -2- imidazolines
Ketone is higher boiling, intensive polar solvent, and it is speed that can be effectively increased catalytic reaction.
【Embodiment】
Embodiment 1：
The method that DFF is prepared using saccharide compound degraded, is comprised the following steps：
(1)：Count by weight, be 5% potassium permanganate solution, 0.2 portion of vinegar by 4.5 parts of fructose, 0.5 part of mass fraction
The DMI aqueous solution that sour copper and 100 parts of mass fractions are 80%, is poured into autoclave, fast
Stirred after speed sealing with 300r/min rotating speed, form limpid solution；
(2)：Continue holding 300r/min mixing speed, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
The volume ratio of carbon dioxide and oxygen in the mixed gas of kettle, wherein carbon dioxide and oxygen is 4：1, make the pressure in kettle be
5MPa, is subsequently heated autoclave, makes temperature to 160 DEG C, stops reaction after reaction 100min, naturally cools to room temperature, i.e.,
Obtain the mixed liquor that DFF is primary product.
Product is analyzed with high performance liquid chromatography, following result is obtained：Fructose converting rate is 97.27%, 2,5-
Furans dicarbaldehyde yield is 40.25%.
Embodiment 2：
The method that DFF is prepared using saccharide compound degraded, is comprised the following steps：
(1)：Count by weight, by 7.5 portions of sucrose, 10 parts be mass fraction be 30% aqueous hydrogen peroxide solution, 0.1
The DMI aqueous solution that part cupric oxide and 100 parts of mass fractions are 80%, pours into autoclave
In, stirred after rapid sealing with 300r/min rotating speed, form limpid solution；
(2)：Continue holding 300r/min mixing speed, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
The volume ratio of carbon dioxide and oxygen in the mixed gas of kettle, wherein carbon dioxide and oxygen is 3.5：1, make the pressure in kettle be
3MPa, is subsequently heated autoclave, makes temperature to 180 DEG C, stops reaction after reaction 120min, naturally cools to room temperature, i.e.,
Obtain the mixed liquor that DFF is primary product.
Product is analyzed with high performance liquid chromatography, following result is obtained：Sucrose conversion is 93.27%, 2,5-
Furans dicarbaldehyde yield is 23.22%.
Embodiment 3：
The method that DFF is prepared using saccharide compound degraded, is comprised the following steps：
(1)：Count by weight, by 15 portions of glucose sugar, 4 parts of mass fractions be 10% ammonium persulfate aqueous solution, 0.25 part
The DMI aqueous solution that cupric oxalate and 100 parts of mass fractions are 80%, is poured into autoclave,
Stirred after rapid sealing with 300r/min rotating speed, form limpid solution；
(2)：Continue holding 300r/min mixing speed, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
The volume ratio of carbon dioxide and oxygen in the mixed gas of kettle, wherein carbon dioxide and oxygen is 3：1, make the pressure in kettle be
2.5MPa, is subsequently heated autoclave, makes temperature to 150 DEG C, stops reaction after reaction 60min, naturally cools to room temperature, i.e.,
Obtain the mixed liquor that DFF is primary product.
Product is analyzed with high performance liquid chromatography, following result is obtained：Inversion rate of glucose is 87.72%, 2,
5- furans dicarbaldehydes yield is 15.25%.
Embodiment 4：
The method that DFF is prepared using saccharide compound degraded, is comprised the following steps：
(1)：Count by weight, the aqueous hydrogen peroxide solution for being 30% by 22.5 parts of starch, 16 parts of mass fractions, 0.15
The DMI aqueous solution that part Kocide SD and 100 parts of mass fractions are 80%, pours into autoclave
In, stirred after rapid sealing with 300r/min rotating speed, form limpid solution；
(2)：Continue holding 300r/min mixing speed, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
The volume ratio of carbon dioxide and oxygen in the mixed gas of kettle, wherein carbon dioxide and oxygen is 4：1, make the pressure in kettle be
2MPa, is subsequently heated autoclave, makes temperature to 120 DEG C, stops reaction after reaction 240min, naturally cools to room temperature, i.e.,
Obtain the mixed liquor that DFF is primary product.
Product is analyzed with high performance liquid chromatography, following result is obtained：Starch Conversion rate is 79.24%, 2,5-
Furans dicarbaldehyde yield is 10.50%.
Embodiment 5：
The method that DFF is prepared using saccharide compound degraded, is comprised the following steps：
(1)：Count by weight, by 30 parts of celluloses, 1.5 parts of mass fractions be 5% potassium permanganate solution, 0.25 part
The DMI aqueous solution that copper sulphate and 100 parts of mass fractions are 80%, is poured into autoclave,
Stirred after rapid sealing with 300r/min rotating speed, form limpid solution；
(2)：Continue holding 300r/min mixing speed, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
The volume ratio of carbon dioxide and oxygen in the mixed gas of kettle, wherein carbon dioxide and oxygen is 4：1, make the pressure in kettle be
5MPa, is subsequently heated autoclave, makes temperature to 180 DEG C, stops reaction after reaction 180min, naturally cools to room temperature, i.e.,
Obtain the mixed liquor that DFF is primary product.
Product is analyzed with high performance liquid chromatography, following result is obtained：Cellulose conversion ratio is 77.48%, 2,
5- furans dicarbaldehydes yield is 11.85%.
Embodiment 6：
The method that DFF is prepared using saccharide compound degraded, is comprised the following steps：
(1)：Count by weight, be 5% potassium permanganate solution, 0.2 part of nitre by 6 parts of fructose, 0.75 part of mass fraction
The DMI aqueous solution that sour copper and 100 parts of mass fractions are 80%, is poured into autoclave, fast
Stirred after speed sealing with 300r/min rotating speed, form limpid solution；
(2)：Continue holding 300r/min mixing speed, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
The volume ratio of carbon dioxide and oxygen in the mixed gas of kettle, wherein carbon dioxide and oxygen is 3：1, make the pressure in kettle be
3.5MPa, is subsequently heated autoclave, makes temperature to 140 DEG C, stops reaction after reaction 160min, naturally cools to room temperature,
Produce the mixed liquor that DFF is primary product.
Product is analyzed with high performance liquid chromatography, following result is obtained：Fructose converting rate is 94.23%, 2,5-
Furans dicarbaldehyde yield is 32.47%.
Embodiment 7：
The method that DFF is prepared using saccharide compound degraded, is comprised the following steps：
(1)：Count by weight, by 3 portions of glucose sugar, 2.5 parts of mass fractions be 10% ammonium persulfate aqueous solution, 0.15 part
The DMI aqueous solution that copper chloride and 100 parts of mass fractions are 80%, is poured into autoclave,
Stirred after rapid sealing with 300r/min rotating speed, form limpid solution；
(2)：Continue holding 300r/min mixing speed, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
The volume ratio of carbon dioxide and oxygen in the mixed gas of kettle, wherein carbon dioxide and oxygen is 3：1, make the pressure in kettle be
1MPa, is subsequently heated autoclave, makes temperature to 160 DEG C, stops reaction after reaction 220min, naturally cools to room temperature, i.e.,
Obtain the mixed liquor that DFF is primary product.
Product is analyzed with high performance liquid chromatography, following result is obtained：Inversion rate of glucose is 84.28%, 2,
5- furans dicarbaldehydes yield is 20.64%.
Embodiment 8：
The method that DFF is prepared using saccharide compound degraded, is comprised the following steps：
(1)：Count by weight, be 5% potassium permanganate solution, 0.2 part of carbonic acid by 4.5 portions of sucrose, 1 part of mass fraction
The DMI aqueous solution that copper and 100 parts of mass fractions are 80%, is poured into autoclave, rapidly
Stirred after sealing with 300r/min rotating speed, form limpid solution；
(2)：Continue holding 300r/min mixing speed, the mixed gas of carbon dioxide and oxygen is passed through reaction under high pressure
The volume ratio of carbon dioxide and oxygen in the mixed gas of kettle, wherein carbon dioxide and oxygen is 4：1, make the pressure in kettle be
4.5MPa, is subsequently heated autoclave, makes temperature to 120~180 DEG C, stops reaction after 60~240min of reaction, naturally cold
But to room temperature, the mixed liquor that DFF is primary product is produced.
Product is analyzed with high performance liquid chromatography, following result is obtained：Sucrose conversion is 89.25%, 2,5-
Furans dicarbaldehyde yield is 27.54%.
Described above is the detailed description for the present invention preferably possible embodiments, but embodiment is not limited to this hair
The equal change or modification change completed under bright patent claim, the technical spirit suggested by all present invention, all should belong to
Cover the scope of the claims in the present invention.
Claims (6)
1. the method for DFF is prepared using saccharide compound degraded, it is characterised in that：Comprise the following steps：
(1)：Count by weight, by 3~30 parts of saccharide compounds, 0.5~16 part of peroxide agent, 0.1~0.25 part of metal salt
And 100 parts of solvents, pour into autoclave, stirred, formed limpid with 300r/min rotating speed after rapid sealing
Solution；
(2)：Continue holding 300r/min mixing speed, the mixed gas of carbon dioxide and oxygen be passed through autoclave,
It is 1~5MPa to make pressure in kettle, is subsequently heated autoclave, makes temperature to 120~180 DEG C, is stopped after 60~240min of reaction
Only react, naturally cool to room temperature, produce the mixed liquor that DFF is primary product.
2. the method that utilization saccharide compound degraded according to claim 1 prepares DFF, its feature exists
In：Saccharide compound described in step (1) is any one in fructose, sucrose, glucose sugar, starch and cellulose.
3. the method that utilization saccharide compound degraded according to claim 1 prepares DFF, its feature exists
In：Metal salt described in step (1) is copper acetate, cupric oxide, copper sulphate, copper chloride, copper nitrate, copper carbonate, Kocide SD with
And any one in cupric oxalate.
4. the method that utilization saccharide compound degraded according to claim 1 prepares DFF, its feature exists
In：Peroxide agent described in step (1) be mass fraction be 30% aqueous hydrogen peroxide solution, mass fraction be 5% permanganic acid
Aqueous solutions of potassium and mass fraction are any one in 10% ammonium persulfate aqueous solution.
5. the method that utilization saccharide compound degraded according to claim 1 prepares DFF, its feature exists
In：Solvent described in step (1) is the DMI aqueous solution.
6. the method that utilization saccharide compound degraded according to claim 1 prepares DFF, its feature exists
In：The volume ratio of 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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| CN110256381A (en) * | 2019-07-25 | 2019-09-20 | 广西科学院 | One-step method cleans the method for preparing 2,5- furandicarboxylic acid |
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