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Method for preparing diphenolic acid in ionic liquid

An ionic liquid and bisphenolic acid technology, which is applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of difficult recovery of catalysts, easy corrosion of equipment, and high production costs, and achieves low price and operation. Convenience and productivity-enhancing effects

Inactive Publication Date: 2015-01-14
BEIJING FORESTRY UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In 1955, Johnson used levulinic acid and phenol to directly carry out condensation reaction under the catalysis of inorganic acid, the reaction time was 60-72h, and the DPA yield was generally 50%-85% (Johnson S C. Improvements inor relating to diphenolic acid[ P].GB:768,206,1955-02-13; Johnson S C.Improvements in or relating to diphenolic acid[P].GB:790,373,1955-02-05.), however, in this method, inorganic acid The amount used is 4-6 times that of the reaction substrate levulinic acid. The amount used is large, and there are problems such as easy corrosion of equipment and difficult recovery of catalysts. After the reaction is completed, follow-up treatments such as neutralization, washing, and separation are required, and the process flow is long. The production cost is high, and there are environmental pollution problems such as the discharge of waste water and waste residues

Method used

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  • Method for preparing diphenolic acid in ionic liquid
  • Method for preparing diphenolic acid in ionic liquid
  • Method for preparing diphenolic acid in ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] 1. Nucleophilic addition reaction

[0061] Add 208.3g (1.0mol) bisulfate 1-ethyl-3-methylimidazole ([Emim]HSO 4 ) and 94.1g (1.0mol) phenol, stirred and mixed; then in the reactor, 29.0g (0.25mol) levulinic acid and 1.9g (0.015mol) procatalyst sodium sulfite were added successively, stirred and mixed to obtain a mixture; Slowly heat the reactor, the reactor is heated to 40 ° C, and the mixture is subjected to a nucleophilic addition reaction under stirring to obtain a reaction mixture; wherein, the molar ratio between levulinic acid, phenol and the ionic liquid in the mixture is 1: 4: 4, the mol ratio of levulinic acid and cocatalyst is 1: 0.06, the temperature of control reaction is 40 ℃, and the reaction time is 20 hours;

[0062] 2. Separate the reaction mixture

[0063] Add 1.0L of cooled deionized water (4°C) to the above reaction mixture, stir and mix thoroughly for 5 minutes, then stand and separate layers to obtain an upper organic phase and a lower aqueous ph...

Embodiment 2

[0072] In addition to the nucleophilic addition reaction step, 368.4g (1.0mol) trifluoromethanesulfonate 1-methyl-3-butanesulfonate imidazole ionic liquid ([BSmim] CF 3 SO 3 ) and 94.1g (1.0mol) phenol, stirred and mixed; then in the reactor, 29.0g (0.25mol) levulinic acid and 1.9g (0.015mol) procatalyst sodium sulfite were added successively, stirred and mixed to obtain a mixture; Slowly heat the reactor, the reactor is heated to 60 ° C, and the mixture is subjected to a nucleophilic addition reaction under stirring to obtain a reaction mixture; wherein, the molar ratio between levulinic acid, phenol and the ionic liquid in the mixture is 1: 4: 4, the mol ratio of levulinic acid and cocatalyst is 1: 0.06, and the control reaction temperature is 60 ℃, and the reaction time is 20 hours, all the other are identical with embodiment 1, and the productive rate of bisphenolic acid is 92.5%;

[0073] bisphenolic acid 1 The HNMR nuclear magnetic characterization data is: 1 HNMR (DM...

Embodiment 3

[0075] In addition to the nucleophilic addition reaction step, add 316.3g (1.0mol) bisulfate radical 1-methyl-3-butanesulfonic acid imidazolium ionic liquid ([BSmim]HSO) successively in the reactor 4 ) and 141.2g (1.5mol) phenol, stir and mix; then add 29.0g (0.25mol) levulinic acid and 0.8g (0.005mol) co-catalyst sodium thiosulfate successively to the reactor, stir and mix to prepare Obtain the mixture; slowly heat the reactor, the reactor is heated to 50°C, and the mixture is subjected to a nucleophilic addition reaction under stirring to obtain a reaction mixture; wherein, the molar ratio between levulinic acid, phenol and the ionic liquid in the mixture It is 1: 6: 4, and the mol ratio of levulinic acid and procatalyst is 1: 0.02, and the control reaction temperature is 50 ℃, and the reaction times is 15 hours, and all the other are identical with embodiment 1, and the productive rate of bisphenolic acid is 83.2%;

[0076] bisphenolic acid 1 The HNMR nuclear magnetic chara...

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Abstract

The invention discloses a method for preparing diphenolic acid in ionic liquid, which comprises the following steps in sequence: (1) uniformly mixing levulinic acid, carbolic acid and the ionic liquid to obtain mixture, wherein the structure of the ionic liquid at least contains one acidity group; and (2) conducting nucleophilic addition on the mixture to obtain diphenolic acid mixed liquor. Positive ions of the ionic liquid is selected from alkyl imidazole positive ions, sulfoacid substitution alkyl imidazole positive ions, allyl imidazole positive ions, alkyl pyridine positive ions and one of sulfoacid substitution alkyl pyridine positive ions, sulfoacid substitution alkyl urotropin positive ions and sulfoacid substitution alkyl triethylene diamine positive ions. The method adopts the ionic liquid to serve as a catalytic agent and reaction solvent and is not only simple and convenient in operation, soft in conduction, environment-friendly, low in equipment corrosivity, stable in performance and capable of repeatedly using, and the ionic liquid is easy to recover.

Description

technical field [0001] The invention relates to a method for preparing bisphenolic acid, in particular to a method for preparing bisphenolic acid in ionic liquid. Background technique [0002] Bisphenol A (Bisphenol A, BPA), scientific name 2,2-bis(4-hydroxyphenyl)propane, referred to as diphenolic propane, is produced by condensation of phenol and acetone in acidic medium, and is the most widely used in the world It can be used to produce plasticizers, flame retardants, antioxidants, heat stabilizers, rubber antioxidants, pesticides, coatings and other fine chemical products. [0003] Although bisphenol A is widely used in life, its safety has gradually become the focus of public attention. Studies have shown that bisphenol A is a low-toxic chemical, which has the effect of simulating estrogen and certain embryotoxicity and teratogenicity, and can significantly increase the occurrence of ovarian cancer, prostate cancer, leukemia and other cancers in animals. Bisphenol A i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/52C07C51/367
Inventor 王波周帅许凤孙润仓
Owner BEIJING FORESTRY UNIVERSITY
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