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Preparation of Phenol- or Thiophenyl-Sulfonic Acid Functionalized Solid Acids

a technology of thiophenyl sulfonic acid and solid acids, which is applied in the field of preparation of solid acids, can solve the problems of acid resin deterioration, acid resin is usually deteriorated after reaction, and the pore size of acid aluminosilicate zeolite is too small to accommodate large medical molecules

Active Publication Date: 2015-06-25
NAT TAIWAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The resulting aryl sulfonic acid-functionalized solids demonstrate improved acid capacity, thermal stability, and recyclability, outperforming commercial catalysts like Amberlyst-15 in catalyzing esterification reactions and maintaining catalytic activity across multiple cycles.

Problems solved by technology

However, the pore size of the acid aluminosilicate zeolite is too small to accommodate large medical molecules, and the reaction temperature needed by the acid aluminosilicate zeolite is usually 200-300° C. to present enough acidity.
As for the acid resin, the acid resin will be swelled by solvents to affect the effective acid amount, and the thermal stability of the acid resin is kind of poor.
Therefore, the acid resin is usually deteriorated after reaction and difficult to be regenerated.

Method used

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  • Preparation of Phenol- or Thiophenyl-Sulfonic Acid Functionalized Solid Acids
  • Preparation of Phenol- or Thiophenyl-Sulfonic Acid Functionalized Solid Acids
  • Preparation of Phenol- or Thiophenyl-Sulfonic Acid Functionalized Solid Acids

Examples

Experimental program
Comparison scheme
Effect test

example 1

3-(2-Hydroxy-5-Methylphenyl)-Propyltrimethoxysilane

[0046]

[0047]As shown in Scheme 2, a new 3-arylpropyl trimethoxysilane compound, 3-(2-hydroxy-5-methylphenyl)-propyltrimethoxysilane (abbreviated PholTMS) was synthesized. 60 g of p-cresol and 100 g of 3-chloropropyltrimethoxysilane were mixed under reflux for 24 hours. The product was confirmed by NMR spectrum, and the yield was more than 99%. 1H NMR of PholTMS (400 MHz, CD3OD): δ 0.65 (t, 2H), 1.56 (p, 2H), 2.34 (s, 3H), 2.63 (t, 2H), 3.58 (s, 9H), 6.5-7 (m, 3H).

example 2

3-Thienyl-Propyltrimethoxysilane

[0048]

[0049]As shown in Scheme 3, a new 3-arylpropyl trimethoxysilane compound, 3-thienyl-propyltrimethoxysilane (abbreviated ThioTMS) was synthesized. 60 g of thiophene, 100 g of 3-chloropropyltrimethoxysilane and 0.1 g of anhydrous AlCl3 were mixed under reflux for 24 hours. The product was confirmed by NMR spectrum, and the yield was more than 99%. 1H NMR of ThioTMS (400 MHz, CD3OD): δ 0.65 (t, 2H), 1.56 (p, 2H), 2.66 (t, 2H), 3.58 (s, 9H), 6.5-7 (m, 2H), 7.35 (d, 1H).

Preparation of Aryl Sulfonic Acid-Functionalized Solid by Grafting Method

example 3

Phenolsulfonic Acid-Functionalized Silica Gel

[0050]In this embodiment, PholTMS was grafted onto silica gel to form phenol-functionalized silica gel, which is denoted by Phol-SiO2. Then, phenol-functionalized silica gel was sulfonated by concentrated H2SO4 to form phenolsulfonic acid-functionalized silica gel, which is denoted by PholSO3H—SiO2.

[0051]Accordingly, a phenol-functionalized silica gel was prepared first. In this step, 2.0 mL of PholTMS synthesized above was reacted with 4 g of silica gel (Sigma Aldrich) in 10 mL of toluene under reflux for 24 hours. Then, the obtained solid product Phol-SiO2 was filtered and dried at 100° C.

[0052]Next, a phenolsulfonic acid-functionalized silica gel was prepared. In this step, 4 g of Phol-SiO2 powder in 40 mL of concentrated H2SO4 was heated at 80° C. for 24 hours. After cooling and diluting the mixture with 150 mL of water, the solid product PholSO3H—SiO2 was collected by filtration and dried at 100° C.

[0053]Some physicochemical properti...

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Abstract

Some aryl sulfonic acid-functionalized solids were prepared by a new method. The catalytic activities of esterification by the prepared aryl sulfonic acid-functionalized solids were also tested.

Description

BACKGROUND[0001]1. Technical Field[0002]The disclosure relates to preparation of solid acids.[0003]2. Description of Related Art[0004]Solid acids are widely used in industry. There are two important types of solid acids, one is acid aluminosilicate zeolite, and the other one is acid resin (such as amberlyst-15 having a polystyrene backbone). However, the pore size of the acid aluminosilicate zeolite is too small to accommodate large medical molecules, and the reaction temperature needed by the acid aluminosilicate zeolite is usually 200-300° C. to present enough acidity. As for the acid resin, the acid resin will be swelled by solvents to affect the effective acid amount, and the thermal stability of the acid resin is kind of poor. Therefore, the acid resin is usually deteriorated after reaction and difficult to be regenerated.SUMMARY[0005]In one aspect, the present disclosure provides a method of preparing an aryl sulfonic acid-functionalized solid to be a solid acid. The method co...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07F7/18
CPCC07F7/1892
Inventor CHENG, SOOFINCHEN, CHIA-HAN
Owner NAT TAIWAN UNIV