Solid acid catalyst, preparation thereof and application thereof in esterification reaction

A technology of solid acid catalyst and alkyl sultone, applied in catalyst activation/preparation, carboxylate preparation, organic compound preparation and other directions, to achieve the effect of convenient operation, simple synthesis process and clean process

Inactive Publication Date: 2009-11-11
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In summary, the current research on the synthesis of heteropolyacids with ionic liquid structure is still in its infancy, and mos

Method used

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  • Solid acid catalyst, preparation thereof and application thereof in esterification reaction
  • Solid acid catalyst, preparation thereof and application thereof in esterification reaction
  • Solid acid catalyst, preparation thereof and application thereof in esterification reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] [Example 1] Synthesis of Arylated Phosphotungsto Heteropoly Salt A:

[0027] (1) In a 100 mL three-necked flask equipped with a magnetic stirring bar, a constant-pressure dropping funnel and a spherical condenser, add 5.25 g of triphenylphosphine and 20 mL of toluene, stir to dissolve, and heat up to 40℃, digital temperature controller controls the temperature. 2.69g of 1,3-propane sultone and 15mL of toluene were prepared into a solution and added dropwise to the above solution through a constant pressure dropping funnel. After the dropwise addition was completed for 2 hours, the solution was stirred at 40 °C for 24 hours, and then heated to 140 °C and stirred 36h. Suction filtration, repeatedly washed with toluene, and dried at 100 °C for 12 h to obtain 6.73 g of 3-sulfonic acid propyltriphenylphosphine inner salt (C 6 H 5 ) 3 P(CH 2 ) 3 SO 3 H, 87.5% yield.

[0028] (2) In a 250 mL single-necked flask equipped with a magnetic stirring bar and a constant-press...

Embodiment 2

[0030] [Example 2] Synthesis of butylsulfonic acid functionalized arylphosphotungstic heteropoly acid salt B:

[0031] (1) In a 100 mL three-necked flask equipped with a magnetic stirrer, a constant-pressure dropping funnel and a spherical condenser, add 2.62 g of triphenylphosphine and 10 mL of toluene, stir to dissolve, and heat up to 40℃, digital temperature controller controls the temperature. 1.36g of 1,4-butanesultone and 15mL of toluene were prepared into a solution and added dropwise to the above solution through a constant pressure dropping funnel. The dropwise addition was completed for 2 hours, and then heated to 140°C and stirred for 48 hours. Suction filtration, washed repeatedly with toluene, and dried at 100 °C for 12 h to obtain 3.54 g of 4-sulfonic acid butyltriphenylphosphine inner salt (C 6 H 5 ) 3 P(CH 2 ) 4 SO 3 H, 88.9% yield.

[0032] (2) In a 250 mL single-necked flask equipped with a magnetic stirring bar and a constant-pressure dropping funnel,...

Embodiment 3

[0033] [Example 3] Synthesis of alkylated phosphotungstic heteropoly acid salt C:

[0034] (1) In a 100 mL three-necked flask equipped with a magnetic stirring bar, a constant-pressure dropping funnel and a spherical condenser, add 1.22 g of 1,3-propane sultone and 10 mL of benzene. While stirring, a solution of 0.76 g of trimethylphosphine and 10 mL of benzene was added dropwise to the above solution through a constant pressure dropping funnel. Suction filtration, repeatedly washed with benzene, and dried at 100 °C for 12 h to obtain 1.56 g of 3-sulfonic acid propyltrimethylphosphine inner salt (CH 3 ) 3 P(CH 2 ) 3 SO 3 H, 78.8% yield.

[0035] (2) In a 250 mL single-necked flask equipped with a magnetic stirring bar and a constant-pressure dropping funnel, add 0.4 g of 3-sulfonic acid propyltrimethylphosphine inner salt and 50 mL of water, and stir to dissolve. A solution prepared from 2.1 g of 12-phosphotungstic acid and 50 mL of water was added dropwise to the above ...

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Abstract

The invention relates to a solid acid catalyst, preparation thereof and application thereof in esterification reaction. The solid acid catalyst is prepared from heteropoly acid and organic phosphine. The preparation method comprises two steps: firstly, the organic phosphine and alkyl sultone are reacted in organic solvent to generate internal phosphonium salt containing alkyl sulfonic acid lateral chains; and then the internal phosphonium salt and the heteropoly acid are mixed into a solution respectively, two solutions are mixed under stirring in chemometry mixture ratio to generate organic heteropolyacid, solvent is removed by evaporation under reduced pressure, and the organic heteropolyacid is washed and dried. The catalyst has the characteristics of high activity and selectivity, and reusability for multiple times, and is suitable for various esterification reactions taking carboxylic acid and alcohol as raw materials.

Description

technical field [0001] The present invention relates to a kind of solid acid catalyst and its preparation and application, specifically to a kind of composition structure of a kind of heteropolyacid type organic quaternary phosphonium salt catalyst, preparation method and this catalyst in carboxylic acid and alcohol esterification reaction application. Background technique [0002] It is well known that in the esterification of carboxylic acids with alcohols, the traditional acidic catalyst is H 2 SO 4 , H 3 PO 4 , HF and AlCl 3 and other inorganic acids. Although these traditional liquid acid or Lewis acid catalysts have high activity, they all have strong corrosiveness and toxicity, which will cause a series of problems such as equipment corrosion, product post-processing difficulties and environmental pollution. Therefore, these inorganic acid catalysts should be gradually used. replaced by solid acid catalysts. [0003] Heteropoly compounds (including heteropolyac...

Claims

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Application Information

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IPC IPC(8): B01J31/12B01J37/00C07C67/08C07C69/14C07C69/704C07C69/40C07C69/18C07C69/16
Inventor 王军张卫红冷炎
Owner NANJING UNIV OF TECH
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