CN109400557A - A method of furancarboxylic acid and 5-HMFA are prepared using biomass - Google Patents
A method of furancarboxylic acid and 5-HMFA are prepared using biomass Download PDFInfo
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- CN109400557A CN109400557A CN201811386417.0A CN201811386417A CN109400557A CN 109400557 A CN109400557 A CN 109400557A CN 201811386417 A CN201811386417 A CN 201811386417A CN 109400557 A CN109400557 A CN 109400557A
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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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- 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
- C07D307/56—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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Abstract
The invention discloses propose a kind of method for preparing furancarboxylic acid and 5-HMFA using biomass.This method comprises the following steps: (1) using oxygenous gas as oxidant, pass through the collective effect of the first homogeneous acid catalyst and load type metal catalyst, under hydrothermal reaction condition, the degradation solution containing gluconic acid and xylonic is converted biomass into；(2) degradation solution containing gluconic acid and xylonic is placed in inert atmosphere, sequentially adds organic solvent and the second homogeneous acid catalyst obtains mixed liquor and reacted to get furancarboxylic acid and 5-HMFA.Very small amount of solid residue is generated in the entire reaction process of method proposed by the present invention, avoids the problems such as generating low target product brought by a large amount of solid residues, equipment wall surface carbon distribution and line clogging in traditional biomass degradation process.
Description
Technical field:
The present invention relates to biomass technical field of chemistry, and in particular to a kind of to prepare furancarboxylic acid and 5- methylol using biomass
The method of furancarboxylic acid.
Background technique:
Multi-functional platform chemicals are prepared with biomass resource be widely present in nature, reproducible, to the mankind
The sustainable development of society is of great significance.Cellulose and hemicellulose be in the main component and the earth of biomass most
For the carbohydrate being widely present.So cellulose and hemicellulose are efficiently catalytically conveted to platform chemicals, go forward side by side
And liquid fuel, high molecular material and various downstream chemical product are converted into, have to the higher value application of biomass resource important
Meaning.
Furancarboxylic acid and 5-HMFA are the derivative platform chemicals of two kinds of multifunctional biomass bases, and wherein furancarboxylic acid can then be used
In synthesis furans, tetrahydrofuran, furfuryl alcohol, methylfuran, furoamide and furoate etc., and 5-HMFA can be used for preparing
Furfuryl alcohol, 2,5- furandicarboxylic acid, 2,5- furyl dimethyl carbinol etc..Normally, furancarboxylic acid and 5- methylol are prepared using biomass resource
The method of furancarboxylic acid includes the following steps: in (1) thermal and hydric environment, work of the cellulose and hemicellulose in biomass in acid catalyst
Glucose and xylose is hydrolyzed under, and further dehydration generates 5 hydroxymethyl furfural and furfural；(2) 5 hydroxymethyl furfural and chaff
Aldehyde is oxidized into 5-HMFA and furancarboxylic acid under the action of oxidant and catalyst.In the technology path, step (1) is logical
Often need to carry out in organic solvent because in aqueous solution conversion of biomass when, the selectivity of furfural and 5 hydroxymethyl furfural
It is lower, and a large amount of solid residue attachment and reactor surface or pipe surface are generated in reaction process, lead to line clogging
Or a large amount of carbon distributions of reactor wall surface.But step (2) usually requires to carry out in aqueous solution, because if in organic solvent
Furfural and 5 hydroxymethyl furfural are aoxidized, then organic solvent can also be synchronized and be aoxidized.If by furfural prepared by step (1) and
5 hydroxymethyl furfural is separated from organic solvent to be aoxidized in aqueous solution again, then that there are separation processes is cumbersome again, point
The problems such as high from energy consumption.Currently, being dropped using agricultural wastes such as corncob, corn stalk, rice husk, peanut shell, bagasse, wheat straw etc.
Solution production furfural and the technology of furancarboxylic acid have industrialized, and prepare 5 hydroxymethyl furfural and 5-HMFA using biomass
Technology still not yet realizes industrialization.
Summary of the invention:
The object of the present invention is to provide a kind of method for preparing furancarboxylic acid and 5-HMFA using biomass, the present invention is mentioned
Method furancarboxylic acid and 5-HMFA high income out without separating product between each step in entire reaction process, and generate
Solid residue it is few, so as to avoid target product brought by a large amount of solid residues is generated in traditional biomass degradation process
The problems such as low, equipment wall surface carbon distribution and line clogging.
The present invention is achieved by the following technical programs:
The purpose of the present invention is to propose to a kind of method for preparing furancarboxylic acid and 5-HMFA using biomass, including it is as follows
Step:
(1) using oxygenous gas as oxidant, pass through the first homogeneous acid catalyst and load type metal catalyst
Collective effect converts biomass into the degradation solution containing gluconic acid and xylonic under hydrothermal reaction condition；
(2) degradation solution containing gluconic acid and xylonic that step (1) obtains is placed in inert atmosphere, is sequentially added
Organic solvent and the second homogeneous acid catalyst obtain mixed liquor, and mixed liquor is warming up to 160 DEG C of -220 DEG C of reaction 1-720min,
Up to furancarboxylic acid and 5-HMFA.
Step (1) in oxygenous atmosphere, under the conditions of hydrothermal oxidization catalyzed conversion biomass be generated as gluconic acid and
Xylonic；Step (2) is catalyzed gluconic acid in the two-phase system being made of water and organic solvent and xylonic is converted into 5- hydroxyl
Methyl furancarboxylic acid and furancarboxylic acid.In this method, few solid is all only generated in the catalytic conversion process of step (1) and step (2)
Residue and target product selectivity are high, thus method provided by the invention can greatly improve product yield and
Solid residue is avoided to generate brought a series of problems.
Preferably, the above method specifically comprises the following steps:
(1) using oxygenous gas as oxidant, pass through the first homogeneous acid catalyst and load type metal catalyst
Collective effect is 160 DEG C -220 DEG C in reaction temperature, under conditions of the reaction time is 1-300min, converts biomass into and contain
There is the degradation solution of gluconic acid and xylonic, wherein the quality of first homogeneous acid catalyst is biomass material quality
0.0%-20%, the load type metal catalyst be biomass material quality 0.1%-10%；
(2) degradation solution containing gluconic acid and xylonic that step (1) obtains is placed in inert atmosphere, is sequentially added
Organic solvent and the second homogeneous acid catalyst obtain mixed liquor, and mixed liquor is warming up to 160 DEG C of -220 DEG C of reaction 1-300min,
Up to furancarboxylic acid and 5-HMFA.
Preferably, biomass described in step (1) is the biomass of containing cellulose component.
Preferably, the first homogeneous acid catalyst described in step (1) is inorganic acid or shows acid inorganic salts in water,
The inorganic salts be selected from sodium bisulfate, potassium acid sulfate, lithium hydrogen sulfate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, lithium dihydrogen phosphate,
Calcium dihydrogen phosphate, aluminium chloride, aluminum sulfate, zinc chloride, zinc sulfate, iron chloride, ferric sulfate, chromium chloride, tin tetrachloride and four chlorinations
One or more of germanium, the load type metal catalyst are selected from Cu/SiO2、Cu/C、Co/SiO2、Co/C、Ag/C、Ag/
SiO2、Au/C、Au/SiO2、Pt/C、Pt/SiO2、Pd/C、Pd/SiO2, Ru/C and Ru/SiO2One or more of, wherein metal
Load capacity is 1%-40%.
Preferably, oxygen content is 0.02%-100% in gas oxygenous described in step (1), and oxygen partial pressure is
0.05-1MPa, preferably air.
Preferably, organic solvent described in step (2) is with the volume ratio containing gluconic acid and the degradation solution of xylonic
0.5-10:1, the quality of second homogeneous acid catalyst are the 0.2%-20% of biomass material quality.Organic solvent
It is preferably 1-3:1 with the volume ratio containing gluconic acid and the degradation solution of xylonic.
Preferably, the second homogeneous acid catalyst described in step (2) is inorganic acid or shows acid inorganic salts in water,
The inorganic salts be selected from sodium bisulfate, potassium acid sulfate, lithium hydrogen sulfate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, lithium dihydrogen phosphate,
Calcium dihydrogen phosphate, aluminium chloride, aluminum sulfate, zinc chloride, zinc sulfate, iron chloride, ferric sulfate, chromium chloride, tin tetrachloride and four chlorinations
One of germanium and more than one.
Preferably, organic solvent described in step (2) be selected from methyl formate, Ethyl formate, ethyl acetate, methyl acetate,
Normal propyl alcohol, isopropanol, n-butanol, isobutanol, tetrahydrofuran, methyltetrahydrofuran, cyclopentanone, cyclopentanol, cyclohexanone and hexamethylene
One of alcohol and more than one.
Preferably, the inert gas of inert atmosphere described in step (2) is in nitrogen, argon gas, helium or deoxidation flue gas
It is a kind of and more than one.
The beneficial effects of the present invention are:
(1) above-mentioned preparation method step is simple, operation is simple, raw material is easy to get, reaction condition is mild, at low cost；
(2) by the above method, the biomass resource containing cellulose being widely present in nature can be converted to
Furancarboxylic acid and 5-HMFA with high added value, and the yield that object generates is higher；
(3) very small amount of solid residue is generated in entire reaction process, avoided raw in traditional biomass degradation process
The problems such as, equipment wall surface carbon distribution low at target product brought by a large amount of solid residues and line clogging.
Detailed description of the invention:
Fig. 1 is the preparation route figure for the method that furancarboxylic acid and 5-HMFA are produced in the degradation of two step of biomass.
Specific embodiment:
It is to further explanation of the invention, rather than limiting the invention below.Embodiment 1~15 prepare furancarboxylic acid and
The preparation route of 5-HMFA is as shown in Figure 1.
Embodiment 1:
(1) one step hydrothermal oxidization of corn stover is gluconic acid and xylonic
2.0g corn stover, 0.1g Au/C catalyst and 25mL deionized water are added in the stirred autoclave of 50mL,
200 DEG C, hydrothermal oxidization 2h is carried out to corn stalk raw material in 0.3MPa air, obtain the degradation containing gluconic acid and xylonic
Liquid, wherein gluconic acid yield reaches 54%, and xylonic yield reaches 61%.
(2) degradation solution two phase process prepares 5-HMFA and furancarboxylic acid
Step (1) degradation solution obtained is transferred in 100mL stirred autoclave, and add 0.2g sodium bisulfate,
0.4g zinc sulfate and 25mL tetrahydrofuran then carry out hydrothermal degradation 4h to mixed liquor at 160 DEG C, obtain 34%5- methylol
Furancarboxylic acid and 40% furancarboxylic acid (relative to the cellulose and hemicellulose in corn stover).
Embodiment 2~15:
The reaction step of embodiment 2~15 is same as Example 1, and reaction condition and reaction result are as shown in Table 1 and Table 2,
Table 1 is the reaction condition and saccharic acid yield of 1~15 step of embodiment (1), i.e. different kind organism matter raw material is anti-in 50mL high-pressure stirring
Answer saccharic acid yield in the degradation solution rich in saccharic acid that catalytic degradation obtains in kettle；Table 2, which is that step (1) is obtained, contains glucose
The degradation solution of acid and/or xylonic is catalytically conveted to the reaction item of furancarboxylic acid and 5-HMFA in 100mL stirred autoclave
The yield of part and furancarboxylic acid and 5-HMFA.The yield of gluconic acid and xylonic is relative in biomass material in table 1
Cellulose and hemicellulose quality for；The yield of furancarboxylic acid and 5-HMFA is relative in biomass material in table 2
Cellulose and hemicellulose quality for.
Table 1
Table 2
It is obtained by Tables 1 and 2, method provided by the invention, which can convert the biomass resource containing cellulose to, to be had
The furancarboxylic acid and 5-HMFA of high added value, and the yield that object generates is higher.The technical step is simple, operation is simple,
Raw material is easy to get, reaction condition is mild, at low cost.In addition, catalyst used in reaction process is cheap and easy to get, and the solid generated
The problems such as mass of residue is less, can be avoided equipment slagging blocking.
Claims (9)
1. a kind of method for preparing furancarboxylic acid and 5-HMFA using biomass, which comprises the steps of:
(1) using oxygenous gas as oxidant, pass through the common of the first homogeneous acid catalyst and load type metal catalyst
Effect, under hydrothermal reaction condition, converts biomass into the degradation solution containing gluconic acid and xylonic；
(2) degradation solution containing gluconic acid and xylonic that step (1) obtains is placed in inert atmosphere, is sequentially added organic
Solvent and the second homogeneous acid catalyst obtain mixed liquor, by mixed liquor be warming up to 160 DEG C of -220 DEG C of reaction 1-720min to get
Furancarboxylic acid and 5-HMFA.
2. the method according to claim 1 for preparing furancarboxylic acid and 5-HMFA using biomass, which is characterized in that packet
Include following steps:
(1) using oxygenous gas as oxidant, pass through the common of the first homogeneous acid catalyst and load type metal catalyst
Effect is 160 DEG C -220 DEG C in reaction temperature, under conditions of the reaction time is 1-300min, converts biomass into containing Portugal
The degradation solution of grape saccharic acid and xylonic, the quality of first homogeneous acid catalyst are the 0.0%- of biomass material quality
40%, the load type metal catalyst is the 0.1%-10% of biomass material quality；
(2) degradation solution containing gluconic acid and xylonic that step (1) obtains is placed in inert atmosphere, is sequentially added organic
Solvent and the second homogeneous acid catalyst obtain mixed liquor, by mixed liquor be warming up to 160 DEG C of -220 DEG C of reaction 1-300min to get
Furancarboxylic acid and 5-HMFA.
3. the method according to claim 1 or 2 for preparing furancarboxylic acid and 5-HMFA using biomass, feature exist
In biomass described in step (1) is the biomass containing cellulosic component.
4. the method according to claim 1 or 2 for preparing furancarboxylic acid and 5-HMFA using biomass, feature exist
In the volume ratio of, the organic solvent and the degradation solution containing gluconic acid and xylonic be 0.5-10:1, described second
The quality of homogeneous acid catalyst is the 0.2%-20% of biomass material quality.
5. the method according to claim 1 or 2 for preparing furancarboxylic acid and 5-HMFA using biomass, feature exist
In the first homogeneous acid catalyst described in step (1) is inorganic acid or shows acid inorganic salts, the inorganic salts in water
Selected from sodium bisulfate, potassium acid sulfate, lithium hydrogen sulfate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, lithium dihydrogen phosphate, calcium dihydrogen phosphate, chlorine
Change one of aluminium, aluminum sulfate, zinc chloride, zinc sulfate, iron chloride, ferric sulfate, chromium chloride, tin tetrachloride and germanium tetrachloride with
On, the load type metal catalyst is selected from Cu/SiO2、Cu/C、Co/SiO2、Co/C、Ag/C、Ag/SiO2、Au/C、Au/
SiO2、Pt/C、Pt/SiO2、Pd/C、Pd/SiO2, Ru/C and Ru/SiO2One or more of, wherein content of metal is 1%-
40%.
6. the method according to claim 1 or 2 for preparing furancarboxylic acid and 5-HMFA using biomass, feature exist
In oxygen content is 0.02%-100%, oxygen partial pressure 0.05-1MPa in oxygenous gas described in step (1).
7. the method according to claim 1 or 2 for preparing furancarboxylic acid and 5-HMFA using biomass, feature exist
In the second homogeneous acid catalyst described in step (2) is inorganic acid or shows acid inorganic salts, the inorganic salts in water
Selected from sodium bisulfate, potassium acid sulfate, lithium hydrogen sulfate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, lithium dihydrogen phosphate, calcium dihydrogen phosphate, chlorine
Change one of aluminium, aluminum sulfate, zinc chloride, zinc sulfate, iron chloride, ferric sulfate, chromium chloride, tin tetrachloride and germanium tetrachloride and one
Kind or more.
8. the method according to claim 1 or 2 for preparing furancarboxylic acid and 5-HMFA using biomass, feature exist
In organic solvent described in step (2) is selected from methyl formate, Ethyl formate, ethyl acetate, methyl acetate, normal propyl alcohol, isopropyl
One of alcohol, n-butanol, isobutanol, tetrahydrofuran, methyltetrahydrofuran, cyclopentanone, cyclopentanol, cyclohexanone and cyclohexanol and
More than one.
9. the method according to claim 1 or 2 for preparing furancarboxylic acid and 5-HMFA using biomass, feature exist
In the inert gas of inert atmosphere described in step (2) is one of nitrogen, argon gas, helium or deoxidation flue gas.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811386417.0A CN109400557B (en) | 2018-11-20 | 2018-11-20 | Method for preparing furoic acid and 5-hydroxymethyl furoic acid by using biomass |
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| CN201811386417.0A CN109400557B (en) | 2018-11-20 | 2018-11-20 | Method for preparing furoic acid and 5-hydroxymethyl furoic acid by using biomass |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109811020A (en) * | 2019-03-20 | 2019-05-28 | 南京工业大学 | The method for catalyzing and synthesizing 5-HMFA using the unusual coccus in Urumchi |
| CN113292521A (en) * | 2021-05-21 | 2021-08-24 | 贵州理工学院 | Method for preparing 5-hydroxymethylfurfural from cellulose biomass |
Citations (2)
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| CN103805647A (en) * | 2014-01-26 | 2014-05-21 | 东华大学 | Method for preparing furoic acid and 5-hydroxymethyl furoic acid by using bacterially-oxidized furfural derivative |
| CN104817524A (en) * | 2015-04-07 | 2015-08-05 | 中南民族大学 | Method for preparing 5-hydroxymethyl furoic acid through catalytic conversion on fructose |
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2018
- 2018-11-20 CN CN201811386417.0A patent/CN109400557B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103805647A (en) * | 2014-01-26 | 2014-05-21 | 东华大学 | Method for preparing furoic acid and 5-hydroxymethyl furoic acid by using bacterially-oxidized furfural derivative |
| CN104817524A (en) * | 2015-04-07 | 2015-08-05 | 中南民族大学 | Method for preparing 5-hydroxymethyl furoic acid through catalytic conversion on fructose |
Non-Patent Citations (2)
| Title |
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| BAOWEN ZHOU，等: "Highly selective photocatalytic oxidation of biomass-derived chemicals to carboxyl compounds over Au/TiO2", 《GREEN CHEMISTRY》 * |
| GUANGSHUN YI，等: "The Direct Conversion of Sugars into 2,5-Furandicarboxylic Acid in a Triphasic System", 《CHEMSUSCHEM.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109811020A (en) * | 2019-03-20 | 2019-05-28 | 南京工业大学 | The method for catalyzing and synthesizing 5-HMFA using the unusual coccus in Urumchi |
| CN109811020B (en) * | 2019-03-20 | 2022-03-29 | 南京工业大学 | Method for catalytically synthesizing 5-hydroxymethyl furoic acid by using deinococcus bruguiensis |
| CN113292521A (en) * | 2021-05-21 | 2021-08-24 | 贵州理工学院 | Method for preparing 5-hydroxymethylfurfural from cellulose biomass |
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| CN109400557B (en) | 2020-08-11 |
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