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Preparation method of furandicarboxylic acid compound

A furandicarboxylic acid and compound technology, applied in the field of furandicarboxylic acid preparation, can solve problems such as shortage

Pending Publication Date: 2022-07-15
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, there is still a lack of a high-efficiency, low-cost method for preparing bifunctional furan compounds through bio-based chemicals

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0037] Preparation of furandicarboxylic acid compounds

[0038] The invention provides a preparation method of furandicarboxylic acid compound. The method uses furoic acid or its ester compound as raw material, and can prepare furandicarboxylic acid in one step with high yield. The method includes the following steps:

[0039] (1) carry out contact reaction with furoic acid or its ester compound with halogenated hydrocarbon, aliphatic alcohol and catalyst to obtain the first reaction mixture;

[0040] (2) the described first reaction mixture is cooled, then underpressure distillation is carried out to obtain the second reaction mixture;

[0041] (3) The second reaction mixture is mixed with the alkaline aqueous solution for reaction, after the reaction is completed, the pH of the reaction mixture is adjusted to <3, and the precipitated solid is separated to obtain a furandicarboxylic acid compound.

[0042] In another preferred embodiment, the alkaline aqueous solution is an...

Embodiment 1

[0062] In a 250ml reaction kettle, 11.5g (0.103mol) of furoic acid was dissolved in 15ml of isopropanol (0.196mol) and 30g of carbon tetrachloride, 1mmol of cobalt chloride was added, and the reaction was conducted at 60°C for 2 hours under reflux. Isopropanol and carbon tetrachloride were distilled off, NaOH aqueous solution was added, refluxed for 0.5 h, cooled to room temperature, and the pH value was adjusted to 1 H-NMR (400MHz, DMSO) test results, furan ring CH, 2H, δ (7.28); carboxyl OH, 2H, δ (13.60), the molecular weight measured by liquid mass spectrometry (LC-MS) is 156.1, the purity greater than 99.4%.

Embodiment 2

[0064] In a 250ml reaction kettle, 14.0g (0.111mol) of methyl furoate was dissolved in 8ml of ethanol (0.137mol) and 60g of tetrachloroethane, 5mmol of nickel iodide was added, the reaction was carried out at 80°C for 1h under reflux, the temperature was lowered, and the pressure was reduced. Ethanol and tetrachloroethane were distilled off, KOH aqueous solution was added, refluxed for 1.0 h, lowered to room temperature, and the pH value was adjusted to 1 H-NMR (400MHz, DMSO) test results, furan ring CH, 2H, δ (7.28); carboxyl OH, 2H, δ (13.60), the molecular weight measured by liquid mass spectrometry (LC-MS) is 156.1, the purity greater than 99.1%.

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Abstract

According to the preparation method of the furandicarboxylic acid compound provided by the invention, furoic acid or an ester thereof is taken as a raw material, and the furandicarboxylic acid compound is prepared through a simple chemical reaction, so that a monofunctional furan compound realizes bifunctionalization. According to the method, the raw materials are rich in source, low in price and easy to obtain, the preparation method is simple, efficient, short in process and few in by-product, and the furandicarboxylic acid compound prepared through the method is high in purity and can meet the requirements of serving as a raw material of polymers such as high-performance polyester, epoxy resin, polyamide and polyurethane and serving as a chemical raw material and a medical intermediate raw material.

Description

technical field [0001] The application belongs to the technical field of the preparation of polymer monomers such as high-performance polyester, epoxy resin, polyamide, and polyurethane, as well as chemical and pharmaceutical intermediates. Specifically, the application relates to a preparation method of furandicarboxylic acid. Background technique [0002] Furandicarboxylic acid (furandicarboxylic acid) compounds can be directly used in the preparation of high-performance polymers such as polyesters, epoxy resins, polyamides, and polyurethanes because of their rigid furan ring and para-position dicarboxylic acid group structure. The polymers prepared with furandioic acid have excellent mechanical properties in terms of strength, modulus, creep resistance, etc., as well as higher glass transition temperature and heat distortion temperature. In addition, furan dicarboxylate itself can also be used as chemical raw materials and pharmaceutical intermediates. [0003] At presen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68
CPCC07D307/68
Inventor 王静刚刘小青朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI