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Method for preparing diphenolic acid in ionic liquid

An ionic liquid, bisphenolic acid technology, 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, long process flow, etc. Convenient operation and the effect of accelerating mass transfer rate

Inactive Publication Date: 2012-07-18
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) hydrogen sulfate 1-ethyl-3-methylimidazole ([Emim]HSO 4 ) And 94.1g (1.0mol) phenol, stir and mix; then add 29.0g (0.25mol) levulinic acid and 1.9g (0.015mol) promoter sodium sulfite into the reaction kettle, stir and mix to obtain a mixture; Slowly heat the reaction kettle to raise the temperature of the reaction kettle to 40°C, and make the mixture undergo a nucleophilic addition reaction under stirring to obtain a reaction mixture; wherein the molar ratio of levulinic acid, phenol and ionic liquid in the mixture is 1: 4:4, the molar ratio of levulinic acid to the co-catalyst is 1:0.06, the reaction temperature is controlled to 40°C, 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 to obtain the upper organic phase and the lower aqueous phase;...

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, stir and mix; then add 29.0g (0.25mol) levulinic acid and 1.9g (0.015mol) promoter sodium sulfite into the reaction kettle, stir and mix to obtain a mixture; Slowly heat the reaction kettle to raise the temperature of the reaction kettle to 60°C, and make the mixture undergo a nucleophilic addition reaction under stirring to obtain a reaction mixture; wherein the molar ratio of levulinic acid, phenol and ionic liquid in the mixture is 1: 4:4, the molar ratio of levulinic acid to the co-catalyst is 1:0.06, the reaction temperature is controlled to 60°C, and the reaction time is 20 hours. The rest are the same as in Example 1, and the yield of bisphenolic acid is 92.5%;

[0073] Bisphenolic 1 HNMR nuclear magnetic characterization data are: 1 HNMR (DMSO, 400MHz, TMS) δ 1.45 (s, 3H, CH...

Embodiment 3

[0075] In addition to the nucleophilic addition reaction step, 316.3g (1.0mol) hydrogen sulfate 1-methyl-3-butanesulfonyl imidazole ionic liquid ([BSmim]HSO 4 ) And 141.2g (1.5mol) phenol, stir and mix; then add 29.0g (0.25mol) levulinic acid and 0.8g (0.005mol) promoter sodium thiosulfate into the reaction kettle, stir and mix well to prepare Obtain a mixture; slowly heat the reactor to raise the temperature of the reactor to 50°C, and make the mixture undergo a nucleophilic addition reaction under stirring to obtain a reaction mixture; wherein, the molar ratio of levulinic acid, phenol and ionic liquid in the mixture It is 1:6:4, the molar ratio of levulinic acid to co-catalyst is 1:0.02, the reaction temperature is controlled to 50°C, and the reaction time is 15 hours. The rest are the same as in Example 1. The yield of bisphenolic acid is 83.2%;

[0076] Bisphenolic 1 HNMR nuclear magnetic characterization data are: 1 HNMR (DMSO, 400MHz, TMS) δ 1.45 (s, 3H, CH 3 ), 1.89~1.93(...

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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 an ionic liquid. Background technique [0002] Bisphenol A (BPA), scientific name 2,2-bis(4-hydroxyphenyl)propane, referred to as diphenol propane, is made by the condensation of phenol and acetone in acidic medium. It is the most widely used in the world One of the industrial compounds, 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-toxicity chemical, which has the effect of mimicking estrogen and has certain embryotoxicity and teratogenicity. It can significantly increase the occurrence of animal ovarian cancer, prostate cancer, leukemia and other cancers. Bi...

Claims

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Application Information

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IPC IPC(8): C07C59/52C07C51/367
Inventor 王波周帅许凤孙润仓
Owner BEIJING FORESTRY UNIVERSITY
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