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Application of acidic ionic liquid in catalyzing and synthesizing diphenolic acid and/or diphenolic acid ester

A technology of acidic ionic liquid and ionic liquid, applied in the field of application of acidic ionic liquid in catalytic synthesis of bisphenolic acid and/or bisphenolic acid ester

Inactive Publication Date: 2014-06-25
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some acidic ionic liquids catalyzed esterification reactions and condensation reactions reported in the literature have the characteristics of high conversion rate, short reaction time, and mild reaction conditions, but there is no research on the use of acidic ionic liquids to catalyze the synthesis of bisphenolic acid or bisphenolate esters to report

Method used

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  • Application of acidic ionic liquid in catalyzing and synthesizing diphenolic acid and/or diphenolic acid ester
  • Application of acidic ionic liquid in catalyzing and synthesizing diphenolic acid and/or diphenolic acid ester
  • Application of acidic ionic liquid in catalyzing and synthesizing diphenolic acid and/or diphenolic acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] (1) Add 0.15mol biimidazole to a 250mL single-necked flask and then add 100mL acetonitrile to dissolve; dissolve 0.30mol 1,3-propane sultone in 20mL toluene and slowly add it dropwise to the flask under ice-bath stirring conditions. After the dropwise addition, the temperature was raised to 50°C to react for 2 hours. After the reaction, the product was filtered and precipitated, and the precipitate was washed three times with 50 mL of ether to obtain diimidazole propanesulfonic acid inner salt (DIM-SO 3 );

[0079] (2) Take 0.1mol diimidazole propanesulfonic acid inner salt (DIM-SO 3 ) in 100mL deionized water, add 0.2mol trifluoromethanesulfonic acid, heat up to 90°C and stir and heat for 5h. After the reaction is over, put the reaction product in a vacuum drying oven and dry at 100°C for 10h , the obtained final product is detected by nuclear magnetic resonance, and the data are as follows: 1 H NMR (400MHz,D 2 O): δ=1.85(s,2H),2.26(m,2H),2.84(t,2H),4.20(s,2H),4.31(...

Embodiment 2

[0082] (1) Add 0.15mol N,N,N′N′-tetramethyl-1,3-propanediamine to a 250mL single-necked flask, then add 100mL acetonitrile to dissolve, and dissolve 0.30mol 1,3-propanesulfonic acid Dissolve the ester in 20mL of toluene and slowly add it dropwise to the flask under the condition of stirring in an ice bath. After the dropwise addition, raise the temperature to 50°C and react for 2 hours. , to get N,N,N',N'-tetramethyl-1,3-propanediamine (DTA-SO 3 );

[0083] (2) Take 0.1mol N,N,N',N'-tetramethyl-1,3-propanediamine (DTA-SO 3 ) was dissolved in 100mL deionized water, added 0.2mol mercaptopropanesulfonic acid and heated to 90°C, stirred and heated for 5h. The final product of the reaction was detected by nuclear magnetic resonance, and the detection data were as follows: 1 H NMR (400MHz,D 2 O): δ=2.15(m,2H), 2.25(m,1H), 2.91(t,2H), 3.08(s,6H), 3.35(t,2H), 3.46(t,2H).

[0084] From the above data, the obtained product was deduced to be N1,N1,N2,N2-tetramethyl-N1,N2-bis(3-sulfo...

Embodiment 3

[0086] (1) Add 0.15mol 4,4′-bipyridine to a 250mL single-necked flask, then add 100mL acetonitrile to dissolve, dissolve 0.30mol 1,3-propane sultone in 20mL toluene, and slowly add it dropwise to the ice In the flask under the condition of bath stirring, after the dropwise addition, the temperature was raised to 50°C for 2 hours of reaction. After the reaction, the reaction product was filtered and precipitated, and the obtained precipitate was washed three times with 50 mL of ether to obtain the inner salt 4,4'-bipyridine propane Sulfonic acid inner salt (DPY-SO 3 );

[0087] (2) Take 0.1mol 4,4'-bipyridylpropanesulfonic acid inner salt (DPY-SO 3 ) was dissolved in 100mL deionized water, added 0.2mol mercaptopropanesulfonic acid and heated to 90°C, stirred and heated for 5h. The final product of the reaction was detected by nuclear magnetic resonance, and the detection data were as follows: 1 H NMR (400MHz,D 2 O): δ=2.45(m,1H), 2.95(t,1H), 4.81(t,1H), 8.48(d,1H), 9.08(d,1...

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Abstract

The invention discloses a method utilizing acidic ionic liquid in catalyzing and synthesizing diphenolic acid and / or diphenolic acid ester. The method comprises heating and stirring 1-100 parts of the acidic ionic liquid, 1-200 parts of levulinic acid and 1-500 parts of phenol for 5-60 hours' reaction under the protection of nitrogen to obtain the diphenolic acid; and continuously adding alcohols into the reacted mixture, stirring and heating the mixture to obtain the corresponding diphenolic acid ester. The acidic ionic liquid utilized in the method is sulfonic acid ion liquid including tertiary amine base monokaryon sulfonic acid ion liquid, imidazolyl monokaryon sulfonic acid ion liquid, pyridyl monokaryon sulfonic acid ion liquid, ditertiary amine base dikaryon sulfonic acid ion liquid, diimidazolyl dikaryon sulfonic acid ion liquid or dipyridyl monokaryon sulfonic acid ion liquid. The method successfully enables the acidic ionic liquid to serve as a catalytic agent to prepare the diphenolic acid and / or the diphenolic acid ester and is simple in preparation process and high in yield. According to the method, the separation of the catalytic agent and the reaction substrate is achieved through a solvent extraction method, and the catalytic agent can be repeatedly used and has no significant inactivation.

Description

technical field [0001] The invention belongs to the application field of acidic ionic liquids. Specifically, the invention relates to the application of an acidic ionic liquid in the catalytic synthesis of bisphenolic acid and / or bisphenolate ester. Background technique [0002] Diphenolic acid (diphenolic acid, DPA, 4,4-bis(hydroxyphenyl)valeric acid) is obtained from the condensation reaction of levulinic acid and phenol, and bisphenolic acid ester can be esterified by diphenolic acid and alcohol under the catalysis of acid catalyst The chemical reaction is obtained. Bisphenolic acid and bisphenolic acid ester are usually used as intermediates to prepare coatings, lubricating oil additives, cosmetics, surfactants, plasticizers, textile auxiliaries, and can also replace bisphenol A for the preparation of epoxy resins, polyesters, etc. Carbonic acid esters (Ma Xiaojian, Wang Yongli, Chang Chun; research progress on the synthesis and application of bisphenolic acid; "Henan C...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/48C07C51/353C07C69/732C07C67/08B01J31/02
Inventor 郭庆祥刘海峰邓理曾繁馨刘军魏续瑞
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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