CN109651311A - A kind of preparation method of 2,5- furandicarboxylic acid - Google Patents
A kind of preparation method of 2,5- furandicarboxylic acid Download PDFInfo
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- CN109651311A CN109651311A CN201811438895.1A CN201811438895A CN109651311A CN 109651311 A CN109651311 A CN 109651311A CN 201811438895 A CN201811438895 A CN 201811438895A CN 109651311 A CN109651311 A CN 109651311A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of germanium, tin or lead
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/32—Manganese, technetium or rhenium
- B01J23/34—Manganese
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
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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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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses one kind 2, the preparation method of 5- furandicarboxylic acid, include the following steps: 5 hydroxymethyl furfural, oxidation catalyst, alkaline matter, solvent mixes, and under the conditions of having existing for oxygen source, catalyzed conversion obtains 2, 5- furandicarboxylic acid, wherein, oxidation catalyst is X-Y layered mixed oxide, X is one of a Group IA element and group iia element in the periodic table of elements, Y is iii group element in the periodic table of elements, Group IV element, Group VB element, group VIB element, V Group IIB element, group VIII element, one of group ib element and group iib element.Present invention selectivity is high, and by-product is few, and reaction condition is mild, and low energy consumption, and oxidation catalyst is cheap, the purity and high income of the 2,5-furandicarboxylic acid for avoiding and greatly reducing production cost of the invention using noble metal catalyst, and be prepared.
Description
Technical field
The present invention relates to chemical substance preparation technical field more particularly to a kind of preparation methods of 2,5-furandicarboxylic acid.
Background technique
With the rapid growth of the world economy, the increasingly depleted environmental pollution with caused by of fossil fuel, especially petroleum
To human society bring it is a series of society and environmental problem, biomass be a kind of widely available carbon source, be fossil resource most
Attractive alternative materials can be used for producing fuel and bulk chemical.Inedible lignocellulose biomass can be with
It is efficiently converted into C5 and C6 monosaccharide by acid-catalyzed hydrolysis, C5 and C6 monosaccharide can be further processed to generate by acid-catalyzed dehydration
Furan compound, such as furfural and 5 hydroxymethyl furfural.
2,5-furandicarboxylic acid (abbreviation FDCA) is stablized as novel paradigmatic structure monomer, performance itself.It can be used to
Polyester, polyamide and polyurethane etc. are prepared, the poly- furandicarboxylic acid glycol ester (abbreviation PEF) that FDCA is prepared is considered as
Replace the important polyester material of polyethylene terephthalate (abbreviation PET), there are the advantages such as biodegradable, environmental protection.
FDCA includes furans dicarbaldehyde, 2,5- dihydroxymethyl furan by the derivative of the formation such as oxidation reaction, reduction reaction, aminating reaction
It mutters and 2,5- dihydroxymethyl tetrahydrofuran etc. is also good polymer monomer.Adipic acid and succinic acid that FDCA open loop obtains etc.
It is also the industrial widely used raw material of industry.
Currently, the preparation method of FDCA is mainly the oxidation conversion of 5 hydroxymethyl furfural (abbreviation 5-HMF), but prepared
Journey still has the problems such as reaction condition is not mild, and catalyst is expensive, catalyst preparation process is complicated uncontrollable.
Summary of the invention
Technical problems based on background technology, the invention proposes a kind of preparation method of 2,5-furandicarboxylic acid,
Present invention selectivity is high, and by-product is few, and reaction condition is mild, and low energy consumption, and oxidation catalyst is cheap, avoids and your gold used
The high income for the 2,5-furandicarboxylic acid that metal catalyst greatly reduces production cost of the invention, and is prepared.
A kind of preparation method of 2,5-furandicarboxylic acid proposed by the present invention, include the following steps: by 5 hydroxymethyl furfural,
Oxidation catalyst, alkaline matter, solvent mix, and have oxygen source it is existing under the conditions of, catalyzed conversion obtains 2,5-furandicarboxylic acid,
Wherein, oxidation catalyst is X-Y layered mixed oxide, and X is in a Group IA element and group iia element in the periodic table of elements
One kind, Y are iii group element in the periodic table of elements, Group IV element, Group VB element, group VIB element, V Group IIB member
One of element, group VIII element, group ib element and group iib element.
Preferably, oxidation catalyst is Na-Mn layered mixed oxide, K-Sn layered mixed oxide, Ca-Au stratiform are answered
Close oxide, Cs-Fe layered mixed oxide, Na-Cu layered mixed oxide, Na-Sn layered mixed oxide, Na-Fe layers
At least one of shape composite oxides.
Above-mentioned Na-Mn layered mixed oxide the preparation method comprises the following steps: to be equipped with MnCl2Disposably add in the flask of aqueous solution
Enter H2O2Aqueous solution stirs to get A liquid；It is added at one time NaOH aqueous solution into A liquid, and is rinsed with water flask inner wall, with
90min is stirred at room temperature in the speed of 800rpm, and filtering, filter cake is rinsed with water 3 times, then rinses 1 time with ethyl alcohol, during the rinsing process,
Filter cake cannot be made to be completely dried, need to keep wet, in order to avoid inactivation, finally dry 18h obtains Na-Mn stratiform in 105 DEG C of baking ovens
Composite oxides.
Above-mentioned X-Y layered mixed oxide is prepared referring to the preparation method of Na-Mn layered mixed oxide, X's
Raw material selects its soluble-salt, and the raw material of Y selects its hydroxide or salt.
Preferably, alkaline matter is sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, carbonic acid
Lithium, sodium bicarbonate, saleratus, potassium tert-butoxide, sodium tert-butoxide, sodium methoxide, potassium methoxide, sodium ethoxide, at least one in potassium ethoxide
Kind.
Preferably, solvent is alcohol, water, acetonitrile, Isosorbide-5-Nitrae-dioxane, dimethyl sulfoxide, N-Methyl pyrrolidone, dichloromethane
At least one of alkane, ethyl acetate and tetrahydrofuran.
Preferably, alcohol is the straight chain alcohol or branched-chain alcoho that carbon atom number is 1-6.
Preferably, oxygen source is at least one of hydrogen peroxide, oxygen, air, ozone, peroxide, hypohalite.
Preferably, the temperature of catalyzed conversion is 40-200 DEG C.
Preferably, the temperature of catalyzed conversion is 100-150 DEG C.
Preferably, the time of catalyzed conversion is 0.5-24h.
Preferably, the time of catalyzed conversion is 10-15h.
Preferably, when oxygen source is gas, the pressure of catalyzed conversion is 0.1-5MPa.
Preferably, when oxygen source is gas, the pressure of catalyzed conversion is 0.1-2MPa.
Preferably, the molar ratio of 5 hydroxymethyl furfural and oxidation catalyst is 0.1-10:1.
Preferably, the molar ratio of 5 hydroxymethyl furfural and oxidation catalyst is 1-5:1.
Preferably, the molar ratio of 5 hydroxymethyl furfural and alkaline matter is 0.01-50:1.
Preferably, the molar ratio of 5 hydroxymethyl furfural and alkaline matter is 0.1-6:1.
Above-mentioned water is deionized water.
The present invention selects 5 hydroxymethyl furfural to prepare 2,5-furandicarboxylic acid, by selecting suitable oxidation catalyst, alkali
Property substance, oxygen source, increase the selectivity of reaction, reduce by-product, improve the yield of 2,5-furandicarboxylic acid, and reaction condition temperature
With low energy consumption, and the preparation method of oxidation catalyst is simple, controllable and cheap, avoids using noble metal catalyst, greatly
Production cost of the invention is reduced greatly, is suitble to industrialized production.
Specific embodiment
In the following, technical solution of the present invention is described in detail by specific embodiment.
Embodiment 1
Prepare Na-Mn layered mixed oxide:
By the MnCl of 0.9mmol2·4H2O is dissolved in 9ml water, is set in a round bottom flask, and 0.279ml mass is added at one time
Score is the H of 30wt%2O2Aqueous solution, stirring 5min obtain A liquid；The NaOH of 38.4mmol is dissolved in 2ml water and obtains NaOH water
Solution；It is added at one time NaOH aqueous solution into A liquid, and rinses round-bottomed flask inner wall with 10ml water, with the speed room of 800rpm
Temperature stirring 90min, filtering, filter cake are rinsed with water 3 times, water 100ml are used every time, then rinsed 1 time with 50ml ethyl alcohol, in flushing process
In, filter cake cannot be made to be completely dried, need to keep wet, in order to avoid inactivation, finally dry 18h obtains Na-Mn layers in 105 DEG C of baking ovens
Shape composite oxides.
Embodiment 2
Prepare K-Sn layered mixed oxide:
By the SnCl of 0.9mmol2·5H2O is dissolved in 9ml water, is set in a round bottom flask, and 0.279ml mass is added at one time
Score is the H of 30wt%2O2Aqueous solution, stirring 5min obtain A liquid；The KaOH of 38.4mmol is dissolved in 2ml water and obtains KaOH water
Solution；It is added at one time KaOH aqueous solution into A liquid, and rinses round-bottomed flask inner wall with 10ml water, with the speed room of 800rpm
Temperature stirring 90min, filtering, filter cake are rinsed with water 3 times, water 100ml are used every time, then rinsed 1 time with 50ml ethyl alcohol, in flushing process
In, filter cake cannot be made to be completely dried, need to keep wet, in order to avoid inactivation, finally dry 18h obtains Na-Mn layers in 105 DEG C of baking ovens
Shape composite oxides.
Embodiment 3
Prepare Na-Fe layered mixed oxide:
By the Fe (NO of 0.9mmol3)3·9H2O is dissolved in 9ml water, is set in a round bottom flask, is added at one time 0.279ml
Mass fraction is the H of 30wt%2O2Aqueous solution, stirring 5min obtain A liquid；The NaOH of 38.4mmol is dissolved in 2ml water and is obtained
NaOH aqueous solution；It is added at one time NaOH aqueous solution into A liquid, and rinses round-bottomed flask inner wall with 10ml water, with 800rpm's
90min is stirred at room temperature in speed, and filtering, filter cake is rinsed with water 3 times, uses water 100ml every time, then rinsed 1 time with 50ml ethyl alcohol, is rushing
During washing, filter cake cannot be made to be completely dried, need to keep wet, in order to avoid inactivation, finally dry 18h is obtained in 105 DEG C of baking ovens
Na-Mn layered mixed oxide.
Na-Cu layered mixed oxide, Ca-Sn layered mixed oxide, Ba-Co layered mixed oxide, K-Mn stratiform
Composite oxides are prepared as described in Example 1.
Embodiment 4
5 hydroxymethyl furfural is dissolved in methanol, Na-Mn layered mixed oxide, K is added2CO3, in atmospheric oxygen atmosphere
In, 80 DEG C of heating stirring 12h obtain reaction mixture, wherein 5 hydroxymethyl furfural and K2CO3Molar ratio be 2.78:1,5- hydroxyl
The molar ratio of methyl furfural and Na-Mn layered mixed oxide is 10:1, the molal volume of 5 hydroxymethyl furfural and methanol
(mmol/ml) than being 1:5；
Using the yield of 2,5-furandicarboxylic acid in HPLC method detection reaction mixture, testing conditions are as follows: mobile phase is
Methanol: 0.5% (v/v) trifluoroacetic acid aqueous solution=20:80 (v/v)；Column temperature=30 DEG C；Flow velocity=0.6ml/min；C18 chromatography
Column；Yield through HPLC method standard curve quantitative determination 2,5- furandicarboxylic acid is 95%.
Embodiment 5
5 hydroxymethyl furfural and K2CO3Molar ratio be 3.47:1, other are the same as embodiment 4, the yield of 2,5-furandicarboxylic acid
It is 86.7%.
Embodiment 6
Methanol is changed to acetonitrile, other are 83.7% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 7
Methanol is changed to ethyl alcohol, other are 90.1% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 8
5 hydroxymethyl furfural and K2CO3Molar ratio be 1.74:1, other are the same as embodiment 4, the yield of 2,5-furandicarboxylic acid
It is 85.1%.
Embodiment 9
Heating stirring 18h, other are 92.9% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 10
By K2CO3It is changed to NaOH, other are 97.4% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 11
By K2CO3It is changed to NaHCO3, other are 88.9% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 12
Methanol is changed to water, other are 96.8% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 13
Heating stirring 6h, other are 77.7% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 14
For 24 hours, other are 95.7% with embodiment 4, the yield of 2,5-furandicarboxylic acid to heating stirring.
Embodiment 15
80 DEG C of heating are changed to 60 DEG C of heating, other are 75.5% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 16
80 DEG C of heating are changed to 100 DEG C of heating, other are 86.3% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 17
80 DEG C of heating are changed to 120 DEG C of heating, other are 89.9% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 18
80 DEG C of heating are changed to 60 DEG C of heating, other are 75.5% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 19
Oxygen pressure is 1MPa, other are 93.1% with embodiment 4, the yield of 2,5-furandicarboxylic acid.
Embodiment 20
Na-Mn layered mixed oxide is changed to Ca-Sn layered mixed oxide, other obtain 2,5- furan with embodiment 4
Mutter dioctyl phthalate yield be 98.7%.
Embodiment 21
Na-Mn layered mixed oxide is changed to Na-Fe layered mixed oxide, other obtain 2,5- furan with embodiment 4
Mutter dioctyl phthalate yield be 91.9%.
Embodiment 22
Na-Mn layered mixed oxide is changed to Ba-Co layered mixed oxide, other obtain 2,5- furan with embodiment 4
Mutter dioctyl phthalate yield be 95.8%.
Embodiment 23
Na-Mn layered mixed oxide is changed to K-Mn layered mixed oxide, other obtain 2,5- furan with embodiment 4
Mutter dioctyl phthalate yield be 65.0%.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Anyone skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.
Claims (10)
1. a kind of preparation method of 2,5-furandicarboxylic acid, which comprises the steps of: by 5 hydroxymethyl furfural, oxygen
Change catalyst, alkaline matter, solvent to mix, and have oxygen source it is existing under the conditions of, catalyzed conversion obtains 2,5-furandicarboxylic acid,
In, oxidation catalyst is X-Y layered mixed oxide, and X is one in a Group IA element and group iia element in the periodic table of elements
Kind, Y be the periodic table of elements in iii group element, Group IV element, Group VB element, group VIB element, V Group IIB element,
One of group VIII element, group ib element and group iib element.
2. the preparation method of 2,5-furandicarboxylic acid according to claim 1, which is characterized in that oxidation catalyst Na-Mn
Layered mixed oxide, K-Sn layered mixed oxide, Ca-Au layered mixed oxide, Cs-Fe layered mixed oxide, Na-
At least one of Cu layered mixed oxide, Na-Sn layered mixed oxide, Na-Fe layered mixed oxide.
3. the preparation method of 2,5-furandicarboxylic acid according to claim 1 or claim 2, which is characterized in that alkaline matter is hydrogen-oxygen
Change sodium, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium bicarbonate, saleratus, the tert-butyl alcohol
At least one of potassium, sodium tert-butoxide, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide.
4. the preparation method of any one of -3 2,5-furandicarboxylic acid according to claim 1, which is characterized in that solvent be alcohol,
In water, acetonitrile, Isosorbide-5-Nitrae-dioxane, dimethyl sulfoxide, N-Methyl pyrrolidone, methylene chloride, ethyl acetate and tetrahydrofuran
At least one；Preferably, alcohol is the straight chain alcohol or branched-chain alcoho that carbon atom number is 1-6.
5. the preparation method of any one of -4 2,5-furandicarboxylic acid according to claim 1, which is characterized in that oxygen source is dioxygen
At least one of water, oxygen, air, ozone, peroxide, hypohalite.
6. the preparation method of any one of -5 2,5-furandicarboxylic acid according to claim 1, which is characterized in that catalyzed conversion
Temperature is 40-200 DEG C；Preferably, the temperature of catalyzed conversion is 100-150 DEG C.
7. the preparation method of any one of -6 2,5-furandicarboxylic acid according to claim 1, which is characterized in that catalyzed conversion
Time is 0.5-24h；Preferably, the time of catalyzed conversion is 10-15h.
8. the preparation method of any one of -7 2,5-furandicarboxylic acid according to claim 1, which is characterized in that when oxygen source is gas
When body, the pressure of catalyzed conversion is 0.1-5MPa；Preferably, when oxygen source is gas, the pressure of catalyzed conversion is 0.1-2MPa.
9. the preparation method of any one of -8 2,5-furandicarboxylic acid according to claim 1, which is characterized in that 5- methylol chaff
The molar ratio of aldehyde and oxidation catalyst is 0.1-10:1；Preferably, the molar ratio of 5 hydroxymethyl furfural and oxidation catalyst is 1-
5:1.
10. the preparation method of any one of -9 2,5-furandicarboxylic acid according to claim 1, which is characterized in that 5- methylol
The molar ratio of furfural and alkaline matter is 0.01-50:1；Preferably, the molar ratio of 5 hydroxymethyl furfural and alkaline matter is 0.1-
6:1.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110862364A (en) * | 2019-11-14 | 2020-03-06 | 中国科学技术大学 | Process for preparing furanylaldehydes |
| CN112138679A (en) * | 2020-09-10 | 2020-12-29 | 厦门大学 | Bimetallic oxide catalyst and preparation and use methods thereof |
| CN112898252A (en) * | 2021-01-18 | 2021-06-04 | 中国科学院宁波材料技术与工程研究所 | Preparation method of 2, 5-furandicarboxylic acid |
| CN113121477A (en) * | 2021-06-02 | 2021-07-16 | 宁波国生科技有限公司 | Preparation method of 2, 5-tetrahydrofuran dicarboxylic acid |
-
2018
- 2018-11-29 CN CN201811438895.1A patent/CN109651311A/en not_active Withdrawn
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110862364A (en) * | 2019-11-14 | 2020-03-06 | 中国科学技术大学 | Process for preparing furanylaldehydes |
| CN110862364B (en) * | 2019-11-14 | 2022-12-30 | 中国科学技术大学 | Process for preparing furanylaldehydes |
| CN112138679A (en) * | 2020-09-10 | 2020-12-29 | 厦门大学 | Bimetallic oxide catalyst and preparation and use methods thereof |
| CN112138679B (en) * | 2020-09-10 | 2021-10-26 | 厦门大学 | Bimetallic oxide catalyst and preparation and use methods thereof |
| US11702395B2 (en) | 2020-09-10 | 2023-07-18 | Xiamen University | Bimetal oxide catalyst and methods |
| CN112898252A (en) * | 2021-01-18 | 2021-06-04 | 中国科学院宁波材料技术与工程研究所 | Preparation method of 2, 5-furandicarboxylic acid |
| CN113121477A (en) * | 2021-06-02 | 2021-07-16 | 宁波国生科技有限公司 | Preparation method of 2, 5-tetrahydrofuran dicarboxylic acid |
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