CN114751881A - Preparation method of furan dicarboxylic acid compound - Google Patents

Preparation method of furan dicarboxylic acid compound Download PDF

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Publication number
CN114751881A
CN114751881A CN202210395945.2A CN202210395945A CN114751881A CN 114751881 A CN114751881 A CN 114751881A CN 202210395945 A CN202210395945 A CN 202210395945A CN 114751881 A CN114751881 A CN 114751881A
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acid
reaction
dicarboxylic acid
furan dicarboxylic
furan
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王静刚
刘小青
朱锦
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Ningbo Institute of Material Technology and Engineering of CAS
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Ningbo Institute of Material Technology and Engineering of CAS
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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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The application provides a preparation method of a furan dicarboxylic acid compound, which takes furoic acid or an esterified product thereof as a raw material, prepares the furan dicarboxylic acid compound through simple chemical reaction, and realizes bifunctionalization of the furan compound with single functionality. 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 furan dicarboxylic acid compound prepared by the method has high purity and can meet the requirements of being used as the raw material of polymers such as high-performance polyester, epoxy resin, polyamide, polyurethane and the like and being used as the raw material of chemical raw materials and medical intermediate products.

Description

Preparation method of furan dicarboxylic acid compound
Technical Field
The application belongs to the technical field of preparation of high-performance polyester, epoxy resin, polyamide, polyurethane and other polymer monomers and chemical and medical intermediates, and particularly relates to a preparation method of furandicarboxylic acid.
Background
The furan dicarboxylic acid (furan dicarboxylic acid) compound contains a rigid furan ring and a para-dicarboxylic acid group structure, so that the furan dicarboxylic acid (furan dicarboxylic acid) compound can be directly used for preparing high-performance polymers such as polyester, epoxy resin, polyamide, polyurethane and the like. The polymer prepared by adopting the furan diacid has excellent mechanical properties in the aspects of strength, modulus, creep resistance and the like, and simultaneously has higher glass transition temperature and thermal deformation temperature. Furthermore, the furan dicarboxylic acid compound itself can be used as a chemical raw material and a pharmaceutical intermediate.
At present, the furandicarboxylic acid is mainly obtained by oxidizing 5-Hydroxymethylfurfural (HMF) serving as a raw material, but the HMF serving as the raw material has the defects of difficult preparation, high cost 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.
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 method for preparing a furandicarboxylic acid compound, comprising the steps of:
(1) carrying out contact reaction on furoic acid or an esterified product thereof, halogenated hydrocarbon, fatty alcohol and a catalyst to obtain a first reaction mixture;
(2) cooling the first reaction mixture, and then carrying out reduced pressure distillation to obtain a second reaction mixture;
(3) and mixing the second reaction mixture with an alkaline aqueous solution for reaction, adjusting the pH of the reaction mixture to be less than 3 after the reaction is finished, and separating the separated solid to obtain the furan dicarboxylic acid compound.
In another preferred embodiment, the alkaline aqueous solution is an aqueous solution of a substance selected from the group consisting of: oxides of alkali metals or alkaline earth metals, hydroxides of alkali metals or alkaline earth metals, carbonates of alkali metals or alkaline earth metals, ammonia water; preferably, the basic aqueous solution is an aqueous solution of a substance selected from the group consisting of: sodium hydroxide, potassium hydroxide, lithium hydroxide, rubidium hydroxide, cesium hydroxide, barium hydroxide, calcium hydroxide, magnesium hydroxide, sodium carbonate, potassium carbonate, ammonia, or combinations thereof.
In another preferred embodiment, the pH adjustment is performed using an acidic substance selected from the group consisting of: inorganic acidic substances, and/or organic acidic substances; preferably, the acidic substance is selected from the group consisting of: hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, methanesulfonic acid, boron trifluoride etherate, phenylmethanesulfonic acid, or a combination thereof.
In another preferred embodiment, in the reaction, the feeding molar ratio of the fatty alcohol to the furoic acid or the esterified product thereof is 1-30:1, preferably 5-20:1, and more preferably 6-15: 1.
In another preferred embodiment, when furoic acid is used as a reactant, the feeding molar ratio of the fatty alcohol to the furoic acid in the reaction is 1-30:1, preferably 5-20:1, and more preferably 6-15: 1.
In another preferred embodiment, when the furoate ester is used as the reactant, the feeding molar ratio of the fatty alcohol to the furoic acid in the reaction is 1-15:1, preferably 2-10:1, and more preferably 3-8: 1.
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, Cr, or a combination thereof.
In another preferred embodiment, the catalyst is selected from the group consisting of: iron chloride, iron bromide, iron iodide, diethyl iron, iron acetylacetonate, cobalt chloride, cobalt bromide, cobalt iodide, diethyl cobalt, cobalt acetylacetonate, nickel chloride, nickel bromide, nickel iodide, diethyl nickel, nickel acetylacetonate, or combinations thereof.
In another preferred example, in the step (1), the molar ratio of the catalyst to the furoic acid or the esterified product thereof is 0.001-0.2: 1.
In another preferred embodiment, the feeding molar ratio of the halogenated hydrocarbon to the furoic acid or the esterified product thereof is 1-20: 1, preferably 2-10: 1.
In another preferred embodiment, the feeding molar ratio of the catalyst to the furoic acid or the esterified product thereof is 0.005-0.1: 1.
In another preferred embodiment, the furoic acid or its esterified product is selected from the group consisting of: furoic acid, methyl furoate, ethyl furoate, propyl furoate, butyl furoate, pentyl furoate, hexyl furoate, heptyl furoate, octyl furoate, nonyl furoate, decyl furoate, or combinations thereof.
In another preferred embodiment, the furoic acid or its esterified product is selected from the group consisting of: furoic acid, methyl furoate, ethyl furoate, propyl furoate, butyl furoate, pentyl furoate, hexyl furoate, or combinations thereof.
In another preferred embodiment, the furoic acid or its ester is selected from the following group: furoic acid, methyl furoate, ethyl furoate, propyl furoate, or combinations 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, tetrabromoethane, or combinations 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, or combinations thereof.
In another preferred embodiment, the fatty alcohol is selected from the group consisting of: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, n-pentanol, isopentanol, n-hexanol, n-heptanol, n-octanol, or a combination thereof.
In another preferred embodiment, the fatty alcohol is a C1-C10 straight chain or branched chain alcohol.
In another preferred embodiment, the fatty alcohol is selected from the group consisting of: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, n-pentanol, isopentanol, n-hexanol; more preferably selected from the group consisting of: methanol, ethanol, propanol, isopropanol, or combinations thereof.
In another preferred embodiment, the reaction temperature of the contact reaction is 60-250 ℃; preferably 120-200 ℃.
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, comprising the steps of:
preparing a furandicarboxylic acid compound by the method according to the first aspect of the present invention; and
the polymerization reaction is carried out by using the furan dicarboxylic acid compound as a monomer, thereby obtaining the polymer.
In another preferred embodiment, the polymerization is a homopolymerization or a copolymerization.
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 reiterated herein, but to the extent of space.
Detailed Description
The present inventors have conducted extensive and intensive studies for a long time and have unexpectedly found that a furan dicarboxylic acid compound can be obtained in a very high yield by using furfural as a raw material, and reacting with a halogenated hydrocarbon, a catalyst and an aliphatic alcohol in this order, and further used in the preparation of a furan-containing structural unit polymer. Based on the above findings, the inventors have completed the present invention.
Preparation of furandicarboxylic acid compounds
The invention provides a preparation method of a furan dicarboxylic acid compound, which takes furoic acid or an esterified product thereof as a raw material to prepare furan dicarboxylic acid with high yield one step. The method comprises the following steps:
(1) carrying out contact reaction on furoic acid or an esterified product thereof, halogenated hydrocarbon, fatty alcohol and a catalyst to obtain a first reaction mixture;
(2) cooling the first reaction mixture, and then carrying out reduced pressure distillation to obtain a second reaction mixture;
(3) and mixing the second reaction mixture with an alkaline aqueous solution for reaction, adjusting the pH of the reaction mixture to be less than 3 after the reaction is finished, and separating out solid to obtain the furan dicarboxylic acid compound.
In another preferred embodiment, the alkaline aqueous solution is an aqueous solution of a substance selected from the group consisting of: oxides of alkali metals or alkaline earth metals, hydroxides of alkali metals or alkaline earth metals, carbonates of alkali metals or alkaline earth metals, ammonia water; preferably, the basic aqueous solution is an aqueous solution of a substance selected from the group consisting of: sodium hydroxide, potassium hydroxide, lithium hydroxide, rubidium hydroxide, cesium hydroxide, barium hydroxide, calcium hydroxide, magnesium hydroxide, sodium carbonate, potassium carbonate, ammonia, or combinations thereof.
In another preferred embodiment, the pH adjustment is performed using an acidic substance selected from the group consisting of: inorganic acidic substances, and/or organic acidic substances; preferably, the acidic substance is selected from the group consisting of: hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, methanesulfonic acid, boron trifluoride etherate, phenylmethanesulfonic acid, or combinations thereof.
In a preferred embodiment of the present invention, the feeding molar ratio of the fatty alcohol to the furoic acid or the esterified product thereof is 1-30:1, preferably 5-20:1, and more preferably 6-15: 1. The specific molar ratio of the raw materials to be charged may be determined depending on the raw materials to be used, and for example, when the raw materials are furoate esters, the charged amount of alcohol may be appropriately reduced.
The process of the invention is carried out with addition of a catalyst, 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; more preferably, the catalyst is a compound of a metal selected from the group consisting of: fe. Co, Ni, Cr, or a combination thereof; for example, ferric chloride, ferric bromide, ferric iodide, diethyl iron, ferric acetylacetonate, cobalt chloride, cobalt bromide, cobalt iodide, diethyl cobalt, cobalt acetylacetonate, nickel chloride, nickel bromide, nickel iodide, diethyl nickel, nickel acetylacetonate, or combinations thereof.
The amount of the catalyst to be used is not particularly limited, and may be determined in accordance with the actual conditions of the reaction system and the reaction apparatus. Preferably, in the step (1), the molar ratio of the catalyst to the furoic acid or the ester thereof is 0.001-0.2: 1.
In the present invention, the feeding ratio of the halogenated hydrocarbon and the furoic acid or the ester thereof is not particularly limited, and in a preferred embodiment, the feeding molar ratio of the halogenated hydrocarbon and the furoic acid or the ester thereof is 1 to 20:1, preferably 2 to 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.
The preparation method of the invention can adopt any furoate ester, and the furoate ester is preferably selected from the following groups: methyl furoate, ethyl furoate, propyl furoate, butyl furoate, pentyl furoate, hexyl furoate, heptyl furoate, octyl furoate, nonyl furoate, decyl furoate, or combinations thereof; more preferably selected from the group consisting of: methyl furoate, ethyl furoate, propyl furoate, butyl furoate, pentyl furoate, hexyl furoate, or combinations thereof.
The kind of the substituted furan compound is not particularly limited, and in the present invention, it is preferable that the substituted furan compound is selected from the group consisting of: 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, tetrabromoethane, or combinations 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, or combinations thereof.
The aliphatic alcohol is not particularly limited, and may be a linear alcohol of C1 to C10. Preferably, the fatty alcohol is selected from the group consisting of: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, n-pentanol, isopentanol, n-hexanol, n-heptanol, n-octanol, 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 of the contact reaction is 60 to 250 ℃; preferably 120-200 ℃.
In another preferred example, the reaction kettle for the contact reaction is an acid-resistant reaction kettle.
The method has the advantages that the furan dicarboxylic acid is directly prepared in one step, the yield reaches 99 percent, most importantly, the obtained product is mainly 2, 5-furan dicarboxylic acid, the purity of the 2, 5-furan dicarboxylic acid in the product can reach 98 percent, and the problems of low yield and poor selectivity of the prepared 2, 5-furan dicarboxylic acid caused by the disproportionation reaction of the 2, 5-furan dicarboxylic acid prepared by the prior furoic acid in carbonate at high temperature and difficult separation of 2, 4-furan dicarboxylic acid isomer contained in the product are completely avoided. The furan dicarboxylic acid prepared by the method can meet the requirements of being used as a raw material of polymers such as high-performance polyester, epoxy resin, polyamide and polyurethane and being used as a raw material of chemical raw materials and medical intermediate products.
The beneficial effects that this application can produce include at least:
(1) the process described herein opens a new route to the preparation of compounds of furan dicarboxylic acid. The furan dicarboxylic acid compound with high purity is prepared with the furfuryl acid or the esterified product thereof as the raw material and the cheap iron, cobalt and nickel metal compounds as the catalyst at high yield, thereby breaking through the technical route from the raw material of the monofunctional furfuryl acid to the bifunctional furan dicarboxylic acid compound and then to the high-performance engineering material.
(2) Because the raw material furoic acid or the esterified product thereof can be sourced from a bio-base, the application can drive the development of the bio-based high polymer material industry, reduce the excessive dependence of the high polymer material on petroleum resources at present, promote the sustainable development of the whole high polymer material industry and reduce the pollution of the petrochemical resources to the environment. (3) The method is simple and efficient, short in flow, few in byproducts, 70% -99% in total yield of the product and suitable for large-scale industrial production.
(4) The furan dicarboxylic acid compound prepared by the method has high purity, and can meet the requirements of being used as a raw material of polymers such as high-performance polyester, epoxy resin, polyamide and polyurethane and being used 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. The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out under conventional conditions or conditions recommended by the manufacturers. 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 11.5g (0.103mol) of furoic acid in 15ml of isopropanol (0.196mol) and 30g of carbon tetrachloride in a 250ml reaction kettle, adding 1mmol of cobalt chloride, carrying out reflux reaction at 60 ℃ for 2h, cooling, carrying out reduced pressure distillation to remove the isopropanol and the carbon tetrachloride, adding an aqueous solution of NaOH, carrying out reflux for 0.5h, cooling to room temperature, adjusting the pH value with hydrochloric acid<1, the solid precipitates to give furandicarboxylic acid in 78% yield. Warp beam1H-NMR (400MHz, DMSO) assay gave, on the furan ring, CH, 2H, delta (7.28); carboxyl OH, 2H, delta (13.60), the molecular weight is 156.1 measured by a liquid phase mass spectrometer (LC-MS), and the purity is more than 99.4%.
Example 2
Dissolving 14.0g (0.111mol) of methyl furoate in 8ml of ethanol (0.137mol) and 60g of tetrachloroethane in a 250ml reaction kettle, adding 5mmol of nickel iodide, carrying out reflux reaction at 80 ℃ for 1h, cooling, removing ethanol and tetrachloroethane by reduced pressure distillation, adding KOH aqueous solution, refluxing for 1.0h, cooling to room temperature, adjusting the pH value by using phosphoric acid <1, the solid is precipitated to give furandicarboxylic acid in 89% yield. Warp beam1H-NMR (400MHz, DMSO) assay gave, on the furan ring, CH, 2H, delta (7.28); carboxyl OH, 2H, delta (13.60), the molecular weight is 156.1 measured by a liquid phase mass spectrometer (LC-MS), and the purity is more than 99.1%.
Example 3
Dissolving 11.5g (0.103mol) of furoic acid in 38ml of methanol (0.921mol) and 20g of tetrabromoethane in a 250ml reaction kettle, adding 5mmol of zinc iodide, carrying out reflux reaction at 70 ℃ for 10h, cooling, removing methanol and tetrabromoethane by reduced pressure distillation, adding KOH aqueous solution, refluxing for 1.0h, cooling to room temperature, adjusting pH value by using nitric acid<1, the solid is precipitated to obtain furandicarboxylic acid with a yield of 99%. Warp beam1H-NMR (400MHz, DMSO) assay gave, on the furan ring, CH, 2H, delta (7.28); carboxy OH, 2H, delta (13.60)) And the molecular weight is 156.1 and the purity is more than 99.9 percent as measured by a liquid phase mass spectrometer (LC-MS).
All documents referred to herein are incorporated by reference into 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 method for preparing furan dicarboxylic acid compound, characterized by comprising the following steps:
(1) the method comprises the following steps of (1) carrying out contact reaction on furoic acid, tetrabromoethane andor carbon tetrachloride, methanol and a catalyst to obtain a first reaction mixture; wherein, the catalyst is zinc iodide; in the reaction, the charging molar ratio of the fatty alcohol to the furoic acid is 6-15: 1;
(2) cooling the first reaction mixture, and then carrying out reduced pressure distillation to obtain a second reaction mixture;
(3) and mixing the second reaction mixture with an alkaline aqueous solution for reaction, adjusting the pH of the reaction mixture to be less than 3 after the reaction is finished, and separating out solid to obtain the furan dicarboxylic acid compound.
2. The method according to claim 1, wherein in the step (1), the molar ratio of the catalyst to the furoic acid or the esterified product thereof is 0.001-0.2: 1.
3. The method according to claim 1, wherein the molar ratio of the halogenated hydrocarbon to the furoic acid or the ester thereof is 1-20: 1.
4. The method according to claim 1, wherein the molar ratio of the halocarbon to the furoic acid or the ester thereof is 2-10: 1.
5. The method of claim 1, wherein the aqueous alkaline solution is an aqueous solution selected from the group consisting of: oxides of alkali metals or alkaline earth metals, hydroxides of alkali metals or alkaline earth metals, carbonates of alkali metals or alkaline earth metals, and ammonia water.
6. The method of claim 1, wherein the adjusting the pH is performed using an acidic substance selected from the group consisting of: hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, methanesulfonic acid, boron trifluoride etherate, phenylmethanesulfonic acid, or a combination thereof.
7. The method of claim 1, wherein said method comprises the steps of: dissolving 11.5g of furoic acid in 38ml of methanol and 20g of tetrabromoethane in a 250ml reaction kettle, adding 5mmol of zinc iodide, carrying out reflux reaction at 70 ℃ for 10h, cooling, carrying out reduced pressure distillation to remove the methanol and the tetrabromoethane, adding KOH aqueous solution, refluxing for 1.0h, cooling to room temperature, adjusting the pH value to be less than 1 by using nitric acid, and separating out a solid to obtain the furandicarboxylic acid.
8. A process for preparing a polymer having furan structural units, comprising the steps of:
preparing a furandicarboxylic acid compound by the method according to any one of claims 1 to 7; and
the polymerization reaction is carried out by using the furan dicarboxylic acid compound as a monomer, thereby obtaining the polymer.
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