CN114773299A - Preparation method of 2, 5-disubstituted furan compound - Google Patents
Preparation method of 2, 5-disubstituted furan compound Download PDFInfo
- Publication number
- CN114773299A CN114773299A CN202210482233.4A CN202210482233A CN114773299A CN 114773299 A CN114773299 A CN 114773299A CN 202210482233 A CN202210482233 A CN 202210482233A CN 114773299 A CN114773299 A CN 114773299A
- Authority
- CN
- China
- Prior art keywords
- furan compound
- furan
- group
- substituted
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The application provides a preparation method of a 2, 5-disubstituted furan compound, and particularly the method takes the 2-substituted furan compound as a raw material, prepares the bifunctional 2, 5-disubstituted furan compound through simple chemical reaction, and realizes the bifunctional of the monofunctional furan compound. The method has the advantages of abundant raw material sources, low price and easy obtainment, simple and efficient preparation method, short flow and few byproducts, and the 2, 5-disubstituted furan compound prepared by the method has high purity and can meet the requirements of serving as the raw material of polymers such as high-performance polyester, epoxy resin, polyamide and polyurethane and serving as the raw material of chemical raw materials and medical intermediate raw materials.
Description
Technical Field
The application relates to a preparation method of a 2, 5-disubstituted furan compound, belonging to the technical field of preparation of high-performance polymer monomers such as polyester, epoxy resin, polyamide and polyurethane and chemical and medical intermediates.
Background
The 2-substituted furan compounds, namely 2-formaldehyde furan, 2-formylfuran, 2-carbomethoxyfuran, 2-hydroxymethylfuran, furan, 2-methylfuran, 2-methoxyfuran and the like, are obtained by catalytic dehydration and conversion of biomass resources such as straws, rice hulls and the like, and the raw materials are cheap and easy to obtain and can be regenerated. The furan compounds contain rigid furan rings, and the prepared polymer has high temperature resistance and good strength modulus. However, since these furan compounds have only one functional group at the 2-position, their application has been limited to the application of furan resins for a long time, and the additional value is low and the application range is difficult to be popularized.
At present, a bifunctional furancarboxylic acid compound is mainly obtained by oxidizing 5-Hydroxymethylfurfural (HMF) serving as a raw material, but has the defects of difficult preparation and high cost of the HMF serving as the raw material and difficult realization of large-scale industrial application. Even if the preparation process of the HMF is improved and the yield is improved, the starting materials for preparing the HMF are fructose and glucose which are main food raw materials, and if the HMF is used for large-scale industrial production, the balance of a food supply chain is necessarily broken. And the cellulose is hydrolyzed to obtain 2-formaldehyde furan, 2-formylfuran, 2-hydroxymethyl furan, 2-methylformate furan, 2-methylfuran and the like, which are cheap and easily-obtained industrial bio-based chemicals, if bifunctional furancarboxylic acid compounds can be prepared from the bio-based chemicals, the sustainable development of bio-based chemical products and bio-based high polymer materials can be well promoted, and a key technical basis is laid for the high-added-value utilization of agricultural residues.
In view of the foregoing, there is a lack in the art of a highly efficient, cost-effective method for preparing difunctional furan compounds from bio-based chemicals.
Disclosure of Invention
The object of the present invention is to provide a process for the preparation of bifunctional furan compounds from bio-based chemicals with high efficiency and at low cost.
In a first aspect of the present invention, there is provided a process for producing a 2, 5-disubstituted furan compound, comprising the steps of:
the furan compound with R group substitution at the 2 position is used for contact reaction with halogenated hydrocarbon, fatty alcohol and a catalyst to obtain a disubstituted furan compound with R group substitution at the 2 position and fatty alcohol methyl ester group at the 5 position;
wherein R is selected from the group consisting of: a substituted or unsubstituted C2-C4 ester group (R' -OOC-); the substituent means that one or more hydrogen atoms on the group are substituted with a substituent selected from the group consisting of: hydroxyl, C1-C3 alkyl.
In another preferred embodiment, the contact reaction is carried out without additional solvent.
In another preferred embodiment, the R group and the fatty alcohol methyl ester group are different groups.
In another preferred embodiment, the catalyst is a compound of a metal selected from the group consisting of: fe. Co, Ni, Cu, Zn, Mg, Cr, Zr, Al, V, or combinations thereof.
In another preferred embodiment, the catalyst is a compound of a metal selected from the group consisting of: fe. Co, Ni, or a combination thereof.
In another preferred embodiment, the catalyst is selected from the group consisting of: ferric chloride, ferric iodide, ferric acetylacetonate, ferric bromide, diethyl iron, cobalt chloride, cobalt iodide, cobalt acetylacetonate, cobalt bromide, diethyl cobalt, or combinations thereof.
In another preferred embodiment, in the reaction, the molar ratio of the catalyst to the 2-substituted furan compound is 0.001-0.2: 1.
in another preferred embodiment, in the reaction, the feeding molar ratio of the fatty alcohol to the 2-substituted furan compound is 4-20: 1, and preferably 8-15: 1.
In another preferred embodiment, the feeding molar ratio of the halogenated hydrocarbon to the 2-substituted furan compound is 1-20:1, preferably 2-10: 1.
In another preferred embodiment, the feeding molar ratio of the catalyst to the 2-substituted furan compound is 0.005-0.1: 1.
In another preferred embodiment, the 2-substituted furan compound is selected from the group consisting of: 2-formylfuran, 2-hydroxymethylfuran, furan, 2-methylfuran, 2-methoxyfuran, 2-carbomethoxyfuran, 2-carboximethylfuran, 2-propanylpuran, or a combination thereof.
In another preferred embodiment, the 2-substituted furan compound is selected from the group consisting of: 2-formylfuran, 2-hydroxymethylfuran, furan, 2-formylmethylfuran, or a combination thereof.
In another preferred embodiment, the 2, 5-disubstituted furan compound is selected from the group consisting of: 2-methyl formate-5-methyl furoate, 2-formaldehyde-5-methyl furoate, 2-hydroxymethyl-5-methyl furoate, 2-methyl-5-methyl furoate, 2-methoxy-5-methyl furoate, 2-carbethoxy-5-methyl furoate, 2-propisocarboxylate-5-methyl furoate, 2-formaldehyde-5-ethyl furoate, 2-hydroxymethyl-5-ethyl furoate, 2-methyl-5-ethyl furoate, 2-methoxy-5-ethyl furoate, 2-carbethoxy-5-ethyl furoate, 2-propisocarboxylate-5-ethyl furoate, 2-formaldehyde-5-propyl furoate, ethyl furoate, propyl furoate, ethyl furoate, ethyl furoate, ethyl and ethyl furoate, ethyl furoate, ethyl and ethyl furoate, ethyl and ethyl, 2-hydroxymethyl-5-furoate propyl ester, 2-methyl-5-furoate propyl ester, 2-methoxy-5-furoate propyl ester, 2-propyl formate based 5-furoate propyl ester, or a combination thereof.
In another preferred embodiment, the halogenated hydrocarbon is selected from the group consisting of: 1-methyl chloride, methylene chloride, chloroform, carbon tetrachloride, dichloroethane, tetrachloroethane, 1-methyl bromide, methylene bromide, bromoform, carbon tetrabromide, ethylene bromide, ethylene tetrabromide, or combinations thereof.
In another preferred embodiment, the halogenated hydrocarbon is selected from the group consisting of: tetrachloroethane, chloroform, carbon tetrachloride, dichloromethane, or combinations thereof.
In another preferred embodiment, the fatty alcohol is selected from the group consisting of: methanol, ethanol, propanol, or combinations thereof.
In another preferred embodiment, the reaction temperature of the contact reaction is 60-250 ℃.
In another preferred example, the reaction kettle for the contact reaction is an acid-resistant reaction kettle.
In a second aspect of the present invention, there is provided a process for preparing a polymer having furan structural units, the process comprising the steps of:
preparing difunctional furan monomers by a process as described in the first aspect of the present invention; and
polymerizing said difunctional furan monomer to obtain said polymer.
It is to be understood that within the scope of the present invention, the above-described features of the present invention and those specifically described below (e.g., in the examples) may be combined with each other to form new or preferred embodiments. Not to be repeated herein, depending on the space.
Detailed Description
The present inventors have conducted extensive and intensive studies for a long time, and have unexpectedly found that a 2, 5-disubstituted furan compound can be obtained in a very high yield by reacting furfural as a raw material with a halogenated hydrocarbon, a catalyst and an aliphatic alcohol in this order, and can be used in the preparation of a polymer containing a furan structural unit. Based on the above findings, the inventors have completed the present invention.
Preparation of 2, 5-disubstituted furan compounds
The invention provides a preparation method of a 2, 5-disubstituted furan compound, which is characterized by comprising the following steps:
the furan compound with R group substitution at the 2 position is used for contact reaction with halogenated hydrocarbon, fatty alcohol and a catalyst to obtain a disubstituted furan compound with R group substitution at the 2 position and fatty alcohol methyl ester group at the 5 position;
wherein R is selected from the group consisting of: a substituted or unsubstituted C2-C4 ester group (R' -OOC-); the substituent means that one or more hydrogen atoms on the group are substituted with a substituent selected from the group consisting of: hydroxyl, C1-C3 alkyl.
In another preferred embodiment, the contact reaction is carried out without additional solvent.
The catalyst of the catalyst is not particularly limited, and is preferably a compound of a metal selected from the group consisting of: fe. Co, Ni, Cu, Zn, Mg, Cr, Zr, Al, V, or combinations thereof.
In another preferred embodiment, the catalyst is a compound of a metal selected from the group consisting of: fe. Co, Ni, or a combination thereof.
In another preferred embodiment, the catalyst is selected from the group consisting of: ferric chloride, ferric iodide, ferric acetylacetonate, ferric bromide, diethyl iron, cobalt chloride, cobalt iodide, cobalt acetylacetonate, cobalt bromide, diethyl cobalt, or combinations thereof.
In the reaction, the amount of the catalyst to be used is not particularly limited, and the molar ratio of the catalyst to the 2-substituted furan compound is preferably 0.001 to 0.2: 1.
In the invention, the ratio of the dosage of the fatty alcohol to the feeding of the 2-substituted furan compound is controlled, so that the 2, 5-disubstituted furan compound is obtained. In the reaction, the feeding molar ratio of the fatty alcohol to the 2-substituted furan compound is preferably 4-20: 1, and more preferably 8-15: 1. The feeding molar ratio can be adjusted within the above range according to the actual needs in the production process, such as 5:1, 6:1, 7:1, 9:1, 12:1, 13:1, and the like.
In the present invention, the feeding ratio of the halogenated hydrocarbon and the 2-substituted furan compound is not particularly limited, and in a preferred embodiment, the feeding molar ratio of the halogenated hydrocarbon to the 2-substituted furan compound is 1-20:1, preferably 2-10: 1.
In another preferred embodiment, the feeding molar ratio of the catalyst to the 2-substituted furan compound is 0.005-0.1: 1.
In another preferred embodiment, the 2-substituted furan compound is selected from the group consisting of: 2-formylfuran, 2-hydroxymethylfuran, furan, 2-methylfuran, 2-methoxyfuran, 2-carbomethoxyfuran, 2-carboximethylfuran, 2-propanylpuran, or a combination thereof.
In another preferred embodiment, the 2-substituted furan compound is selected from the group consisting of: 2-formylfuran, 2-hydroxymethylfuran, furan, 2-formylmethylfuran, or a combination thereof.
In the present invention, the 2, 5-disubstituted furan compound is preferably a compound having an ester group substituent at the 5-position, and is preferably selected from the group consisting of: 2-methyl formate-5-furoate methyl ester, 2-formaldehyde-5-furoate methyl ester, 2-hydroxymethyl-5-furoate methyl ester, 2-methyl-5-furoate methyl ester, 2-methoxy-5-furoate methyl ester, 2-ethyl formate-5-furoate methyl ester, 2-propyl formate-5-furoate methyl ester, 2-formaldehyde-5-furoate ethyl ester, 2-hydroxymethyl-5-furoate ethyl ester, 2-methyl-5-furoate ethyl ester, 2-methoxy-5-furoate ethyl ester, 2-ethyl formate-5-furoate ethyl ester, 2-propyl formate-5-furoate ethyl ester, 2-formaldehyde-5-furoate propyl ester, 2-hydroxymethyl-5-furoate propyl ester, 2-methyl-5-furoate propyl ester, 2-methoxy-5-furoate propyl ester, 2-propyl formate based 5-furoate propyl ester, or a combination thereof.
In the above reaction, the halogenated hydrocarbon is not particularly limited, and preferably the halogenated hydrocarbon is selected from the group consisting of: 1-methyl chloride, methylene chloride, chloroform, carbon tetrachloride, dichloroethane, tetrachloroethane, 1-methyl bromide, methylene bromide, bromoform, carbon tetrabromide, ethylene bromide, ethylene tetrabromide, or combinations thereof.
In another preferred embodiment, the chlorinated hydrocarbon is selected from the group consisting of: tetrachloroethane, chloroform, carbon tetrachloride, dichloromethane, or combinations thereof.
The aliphatic alcohol is not particularly limited, and may be a linear or branched C1-C10 alcohol. Preferably, the fatty alcohol is selected from the group consisting of: methanol, ethanol, propanol, or a combination thereof.
The contact reaction may be carried out under any suitable reaction conditions, which may be specifically considered depending on the reaction system, the reaction apparatus and the like. For example, in a preferred embodiment, the reaction temperature is 60 to 250 ℃.
In another preferred example, the reaction kettle for the contact reaction is an acid-resistant reaction kettle.
The beneficial effects that this application can produce include at least:
(1) the process described herein opens a new route to 2, 5-disubstituted furan compounds. The 2-substituted furan compound is used as a raw material, the cheap iron, cobalt and nickel metal compounds are used as catalysts, and the high-purity 2, 5-disubstituted furan compound is prepared with high yield, so that the technical route for synthesizing the high-performance engineering material from the raw material furan compound is opened.
(2) The 2-substituted furan compound as the raw material can be sourced from a bio-based material, so that the sustainable development of bio-based chemical products and bio-based high polymer materials can be promoted well, and a key technical basis is laid for the high-added-value utilization of agricultural residues.
(3) The method is simple and efficient, short in flow, few in byproducts, 80% -99% in total yield of the product and suitable for large-scale industrial production.
(4) The 2, 5-disubstituted furan compound prepared by the method has high purity, and can meet the requirements of serving as a raw material of polymers such as high-performance polyester, epoxy resin, polyamide, polyurethane and the like and serving as a raw material of chemical raw materials and medical intermediates.
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Experimental procedures without specific conditions noted in the following examples, generally according to conventional conditions, or according to conditions recommended by the manufacturer. Unless otherwise indicated, percentages and parts are by weight. The reagents, the density and concentration parameters of which are not indicated in the examples, are all commercially pure reagents.
Example 1
Dissolving 24g (0.214mol) of 2-formylfuran in 180ml of methanol (4.365mol) and 64g of tetrachloroethane in a 1000ml reaction kettle, adding 3mmol of copper chloride, carrying out reflux reaction at 120 ℃ for 16h, cooling, separating out a solid, and recrystallizing with ethyl acetate to obtain the 2-methyl formate-5-methyl furoate with the yield of 84%. Warp beam1H-NMR (400MHz, DMSO) assay gave, on the furan ring, CH, 2H, delta (7.39); CH (CH)36H, delta (3.81), molecular weight 184.1 by LC-MS and purity 98.5% by HPLC.
Example 2
24g (0.214mol) of 2-formylfuran is dissolved in 150ml of methanol (3.638mol) and 60g of tetrachloroethane in a 100ml reaction kettle, 20mmol of ferric chloride is added, reflux reaction is carried out for 5h at 150 ℃, temperature is reduced, solid is separated out, ethyl acetate is recrystallized, and 2-methyl formate-5-methyl furoate is obtained, wherein the yield is 97%. Warp beam1H-NMR (400MHz, DMSO) assay gave, on the furan ring, CH, 2H, delta (7.43); CH (CH)36H, delta (3.83), molecular weight 184.1 by LC-MS and purity 99.1% by HPLC.
Example 3
In a 1000ml reaction vessel, 24g (0.214mol) of 2-formylfuran was dissolved in 300ml of methanol (7.275mol) and 126g of tetrachloroethane, and the solution was charged60mmol of cobalt chloride, refluxing and reacting for 2h at 150 ℃, cooling, separating out solid, and recrystallizing by ethyl acetate to obtain 2-methyl formate-5-methyl furoate with the yield of 99%. Warp beam1H-NMR (400MHz, DMSO) assay gave, on the furan ring, CH, 2H, delta (7.43); CH (CH)36H, delta (3.83), molecular weight 184.1 by liquid mass spectrometer (LC-MS) and purity 99.0% by HPLC.
Example 4
Dissolving 36g of 2-methyl formate furan in 30ml of ethanol (0.514mol) and 240g of tetrachloroethane in a 1000ml reaction kettle, adding 65mmol of nickel bromide, carrying out reflux reaction at 200 ℃ for 1.5h, cooling, separating out a solid, and recrystallizing ethyl acetate to obtain 2-methyl formate-5-ethyl furoate with the yield of 84%. Warp beam1H-NMR (400MHz, DMSO) assay gave, on the furan ring, CH, 2H, delta (7.37, 7.54); CH (CH)3，3H，δ(3.83)，CH2CH35H, delta (1.30,4.21), molecular weight 198.2 by liquid mass spectrometer (LC-MS) and purity 98.0% by HPLC.
Example 5
Dissolving 80.0g of 2-ethyl formate furan in 320ml of ethanol (5.480mol) and 220g of chloroform in a 1000ml reaction kettle, adding 10mmol of diethyl zinc, carrying out reflux reaction at 180 ℃ for 4h, cooling, separating out a light yellow solid, and recrystallizing ethyl acetate to obtain 2-ethyl formate-5-ethyl furoate with the yield of 87%. Warp beam1H-NMR (400MHz, DMSO) assay gave, on the furan ring, CH, 2H, delta (7.42); CH (CH)3，6H，δ(1.38)，CH24H, delta (4.26), molecular weight 212.2 by liquid mass spectrometer (LC-MS) and purity 98.5% by HPLC.
Example 6
Dissolving 45g of 2-propyl formate furan in 180ml of ethanol (3.083mol) and 360g of tetrachloroethane in a 1000ml reaction kettle, adding 120mmol of magnesium acetylacetonate, carrying out reflux reaction at 240 ℃ for 8h, cooling, precipitating a light yellow solid, and recrystallizing ethyl acetate to obtain 2-propyl formate-5-ethyl formate furan with the yield of 91%. Warp beam1H-NMR (400MHz, DMSO) assay gave, on the furan ring, CH, 2H, delta (7.33, 7.48); CH (CH)3，6H，δ(0.98,1.34)，CH26H, delta (1.81,4.25, 4.30, liquid)The molecular weight was 226.3 by mass spectrometer (LC-MS) and the purity was 99.0% by HPLC.
Example 7
Dissolving 30g of 2-methyl formate-based furan in 144ml of butanol (1.574mol) and 65g of carbon tetrachloride in a 1000ml reaction kettle, adding 40mmol of chromium iodide, carrying out reflux reaction at 150 ℃ for 14h, cooling, separating out a light yellow solid, and recrystallizing ethyl acetate to obtain 2-methyl formate-5-butyl furoate with the yield of 86%. 1H-NMR (400MHz, DMSO) test gave, on the furan ring, CH, 2H, delta (7.29, 7.30); CH (CH)3，3H，δ(0.98，3.83)，CH26H, delta (1.33,1.75, 4.25), molecular weight 226.3 by LC-MS and purity 98.8% by HPLC.
All documents mentioned in this application are incorporated by reference in this application as if each were individually incorporated by reference. Furthermore, it should be understood that various changes and modifications of the present invention can be made by those skilled in the art after reading the above teachings of the present invention, and these equivalents also fall within the scope of the present invention as defined by the appended claims.
Claims (8)
1. A preparation method of a 2, 5-disubstituted furan compound is characterized by comprising the following steps:
the furan compound with R group substitution at the 2 position is used for contact reaction with halogenated hydrocarbon, fatty alcohol and a catalyst to obtain a disubstituted furan compound with R group substitution at the 2 position and fatty alcohol methyl ester group at the 5 position;
wherein R is selected from the group consisting of: a substituted or unsubstituted C2-C4 ester group (R' -OOC-); the substituent means that one or more hydrogen atoms on the group are substituted with a substituent selected from the group consisting of: hydroxy, C1-C3 alkyl;
the furan compound with R group substitution at the 2-position is 2-formylfuran; the aliphatic alcohol is methanol, and the halogenated hydrocarbon is tetrachloroethane;
and the catalyst is cobalt chloride.
2. The process of claim 1, wherein in the reaction, the molar ratio of the catalyst to the 2-substituted furan compound is from 0.001 to 0.2: 1.
3. the method according to claim 1, wherein the molar ratio of the fatty alcohol to the 2-substituted furan compound fed in the reaction is 4-20: 1.
4. The method according to claim 1, wherein the feeding molar ratio of the fatty alcohol to the 2-substituted furan compound in the reaction is 8-15: 1.
5. The process of claim 1, wherein the molar ratio of halogenated hydrocarbon to 2-substituted furan compound is from 1 to 20: 1.
6. The process of claim 1, wherein the molar ratio of halogenated hydrocarbon to 2-substituted furan compound is from 2 to 10: 1.
7. The method of claim 1, wherein the method comprises: dissolving 24g of 2-formylfuran in 300ml of methanol and 126g of tetrachloroethane in a 1000ml reaction kettle, adding 60mmol of cobalt chloride, carrying out reflux reaction at 150 ℃ for 2h, cooling, separating out a solid, and recrystallizing ethyl acetate to obtain 2-carbomethoxy-5-furoic acid methyl ester.
8. A process for preparing a polymer having furan structural units, comprising the steps of:
preparing difunctional furan monomers by the process as claimed in any one of claims 1 to 7; and
polymerizing said difunctional furan monomer to obtain said polymer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210482233.4A CN114773299A (en) | 2017-01-12 | 2017-01-12 | Preparation method of 2, 5-disubstituted furan compound |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210482233.4A CN114773299A (en) | 2017-01-12 | 2017-01-12 | Preparation method of 2, 5-disubstituted furan compound |
| CN201710021908.4A CN108299351A (en) | 2017-01-12 | 2017-01-12 | A kind of preparation method of the disubstituted furan compounds of 2,5- |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710021908.4A Division CN108299351A (en) | 2017-01-12 | 2017-01-12 | A kind of preparation method of the disubstituted furan compounds of 2,5- |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114773299A true CN114773299A (en) | 2022-07-22 |
Family
ID=62871676
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710021908.4A Pending CN108299351A (en) | 2017-01-12 | 2017-01-12 | A kind of preparation method of the disubstituted furan compounds of 2,5- |
| CN202210482233.4A Pending CN114773299A (en) | 2017-01-12 | 2017-01-12 | Preparation method of 2, 5-disubstituted furan compound |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710021908.4A Pending CN108299351A (en) | 2017-01-12 | 2017-01-12 | A kind of preparation method of the disubstituted furan compounds of 2,5- |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN108299351A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112368091A (en) * | 2018-08-16 | 2021-02-12 | 花王株式会社 | Binder composition for mold making |
| CN109776463A (en) * | 2019-03-11 | 2019-05-21 | 重庆化工职业学院 | The preparation method of 2,5- furandicarboxylic acid dialkyl ester |
| CN109824635A (en) * | 2019-03-11 | 2019-05-31 | 重庆化工职业学院 | The method for synthesizing 2,5- furandicarboxylic acid dialkyl ester |
| CN112920145B (en) * | 2021-01-29 | 2023-06-20 | 新乡学院 | Method for synthesizing 2, 5-furandicarboxylic acid by visible light catalysis |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2359968C2 (en) * | 2007-01-17 | 2009-06-27 | Институт нефтехимии и катализа РАН | Production method for methyl ethers of 2-thiophen carbonic acid and its derivatives |
| RU2404173C2 (en) * | 2008-10-07 | 2010-11-20 | Институт нефтехимии и катализа РАН | Method for synthesis of methyl ether of 5-acetylfuran-2-carboxylic acid |
-
2017
- 2017-01-12 CN CN201710021908.4A patent/CN108299351A/en active Pending
- 2017-01-12 CN CN202210482233.4A patent/CN114773299A/en active Pending
Non-Patent Citations (4)
| Title |
|---|
| R. I. KHUSNUTDINOV ET AL.: ""New Procedure for Synthesis Alkyl Esters of 5-Acetyl-2-Furan-Carboxylic Acid Alkyl Ester"", RUSSIAN JOURNAL OF APPLIED CHEMISTRY, vol. 82, no. 2, pages 340 - 342 * |
| R. I. KHUSNUTDINOV ET AL.: ""Synthesis of 2-Thiophenecarboxylic and 2, 5-Thiophenedicar-boxylic Acid Esters via the Reaction of Thiophenes with the CCl4–ROH Reagent in the Presence of Vanadium, Iron, and Molybdenum Catalysts"", PETROLEUM CHEMISTRY, vol. 48, no. 6, pages 471 - 478 * |
| R. I. KHUSNUTDINOV ET AL.: ""Synthesis of methyl furan-2-carboxylate and dimethyl furan-2, 5-dicarboxylate by copper-catalyzed reactions of furans with CCl4 and MeOH"", RUSSIAN CHEMICAL BULLETIN, vol. 62, no. 1, pages 93 - 97, XP035321011, DOI: 10.1007/s11172-013-0012-6 * |
| 李伟杰;: "氯化亚铁催化合成呋喃-2, 5-二甲酸及其二甲酯", 化学试剂, vol. 35, no. 08, pages 767 - 768 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108299351A (en) | 2018-07-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102666521B (en) | Method for the preparation of 2,5-furandicarboxylic acid and for the preparation of the dialkyl ester of 2,5-furandicarboxylic acid | |
| CN114773299A (en) | Preparation method of 2, 5-disubstituted furan compound | |
| Subbiah et al. | Direct transformation of 5-hydroxymethylfurfural to the building blocks 2, 5-dihydroxymethylfurfural (DHMF) and 5-hydroxymethyl furanoic acid (HMFA) via Cannizzaro reaction | |
| CN102648191B (en) | Prepare the method for FDCA and ester thereof | |
| Pingen et al. | Diamines for Polymer Materials via Direct Amination of Lipid‐and Lignocellulose‐based Alcohols with NH3 | |
| EP2220021A1 (en) | Terephthalic acid composition and process for the production thereof | |
| JP2018528171A (en) | Process for preparing furan-2,5-dicarboxylic acid | |
| WO2017076947A1 (en) | Process for preparing furan-2,5-dicarboxylic acid | |
| US9162960B2 (en) | Process for the preparation of a benzene derivative | |
| CN110698440B (en) | Method for preparing 2, 5-furandimethanol from solvent-free 5-hydroxymethylfurfural | |
| CN108299353A (en) | A kind of preparation method of 5- formic acid ester group furan compound | |
| US20170210750A1 (en) | Polyesters From Assymetrical Monomers Based Upon Bisanhydrohexitols | |
| CN114773300A (en) | Method for preparing 2, 5-furandicarboxylic acid from furfural | |
| KR20130112462A (en) | A method for lactide synthesis from lactic acid salt | |
| CN108299352B (en) | Preparation method of furan dicarboxylate compound | |
| US20210032215A1 (en) | CONVERSION OF 1,2,5,6-HEXANETETROL (HTO) TO TETRAHYDROFURAN dicarboxylic acid (THFDCA) | |
| CN114773298A (en) | Preparation method of 2, 5-disubstituted furan compound | |
| CN110483458B (en) | Lactone aromatic derivative containing liquid crystal elements, preparation method thereof, side-chain liquid crystal polymer, preparation method thereof and application thereof | |
| KR20130099623A (en) | A method for lactide synthesis from lactic acid | |
| CN112625014B (en) | Method for preparing 2, 5-furan diformyl chloride from 5-chloromethyl furfural | |
| CN108299350A (en) | A kind of preparation method of furan dicarboxylic acid compound | |
| TWI712584B (en) | New adipate-type compounds and a process of preparing it | |
| CN110452139B (en) | Preparation method of 2-methyl-3-bromo-6-methylsulfonyl benzonitrile | |
| CN114181149B (en) | Synthesis method of 3, 4-dimethylpyrazole | |
| TWI542583B (en) | Oxidation process |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |