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Catalytic esterification method for sulfonic group functionalization morpholine hyamine ion liquid

A quaternary ammonium salt ion, functionalized technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., to achieve high yield, good thermal stability, conversion full effect

Inactive Publication Date: 2008-05-07
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention uses morpholine quaternary ammonium salt ionic liquid functionalized with strong Brnsted acidic sulfonic acid group as catalyst, solvent and dehydrating agent, and is applied to alkyd esterification reaction, and there is no report in the literature

Method used

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  • Catalytic esterification method for sulfonic group functionalization morpholine hyamine ion liquid
  • Catalytic esterification method for sulfonic group functionalization morpholine hyamine ion liquid
  • Catalytic esterification method for sulfonic group functionalization morpholine hyamine ion liquid

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Embodiment 1: Take by weighing 0.05mol of acetic acid, 0.05mol of methanol, 0.01mol of ionic liquid N-(3-sulfonic acid group) propylmorpholine bisulfate; add ionic liquid, methyl alcohol, acetic acid successively with stirrer, In a round bottom flask with a thermometer and a reflux condenser, stir magnetically, and heat and reflux at 40°C for 3 hours; let stand for stratification, and take the upper esterification product, with a yield of 50.69% and a selectivity of 100%; Repeated use after vacuum dehydration.

Embodiment 2

[0028] Embodiment 2: Take by weighing 0.05mol of acetic acid, 0.065mol of ethanol, and 0.01mol of ionic liquid N-(3-sulfonic acid group) propyl morpholine bisulfate; ionic liquid, ethanol, acetic acid are added successively with agitator, In a round bottom flask with a thermometer and a reflux condenser, stir magnetically, and heat and reflux at 80°C for 3 hours; let stand to separate layers, and take the upper esterification product, the yield is 93.4%, and the selectivity is 100%; Repeated use after vacuum dehydration.

Embodiment 3

[0029] Embodiment 3: Take by weighing 0.05mol of acetic acid, 0.065mol of propanol, 0.01mol of ionic liquid N-(3-sulfonic acid group) propyl morpholine bisulfate; add ionic liquid, propanol, acetic acid successively with stirring In a round-bottomed flask with a device, a thermometer, and a reflux condenser, magnetically stir, and heat and reflux at 80° C. for 3 hours; let stand to separate layers, and pipette the upper esterification product. The yield is 83.7%, and the selectivity is 100%. The liquid is vacuum dehydrated and reused.

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Abstract

The invention discloses a method for catalyzing and esterifying sulfoacid basal functional ion liquid in the formula (1), wherein, n equals to 2, 3 and 4; R is H or C1 to C4 saturated or unsaturated alkyl of straight chain or branched chain; negative ion B- is chlorine, bromine, iodine, sulfate radical, hydrogen sulfate radical, nitric acid radical, dihydrogen phosphate radical, tetrafluoride boric acid radical, hexaflurate phosphoric acid radical, acetic acid radical, methyl sulfoacid radical, paratoluenesulfonic acid radical, fluoroform sulfoacid radical and trifluoroacetic acid radical. The adding dosage of the ion liquid is 0.5 to 100 percent of the total mol of the alcohol and acid, reacting for 0.5 to 12 hours under the normal pressure and the temperature of 20 to 140 DEG C, the esterifying reaction is catalyzed to produce the ester. Compared with the traditional acidic catalyst, the ion liquid simplifies the separation of the product of the esterifying reaction and provides higher selectivity. The invention is distinctly characterized in that the phase separation between the produced ester and the catalyst is automatically finished, and the ion liquid is reusable after simple or non treatment.

Description

technical field [0001] The invention relates to an organic chemical reaction method, in particular to a method for catalyzing the esterification of sulfonic acid functionalized morpholine quaternary ammonium salt ionic liquid. Background technique [0002] Organic carboxylate is an important chemical product, widely used as raw material for organic synthesis, spices, plasticizers and solvents. Traditional esterification technology usually uses strong corrosive protonic acids such as concentrated sulfuric acid as catalysts, but there are problems such as equipment corrosion, many side reactions, complicated product separation, and waste acid pollution. Solid-phase catalysts are superior to traditional inorganic acids in terms of product separation and recycling, but the preparation process of these catalysts is complex, or the catalyst life is short, or the esterification selectivity and ester yield are not ideal, and industrial applications still have certain limitations. ....

Claims

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Application Information

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IPC IPC(8): C07C67/08B01J31/02C07D295/08
CPCY02P20/54
Inventor 黄宝华黎子进汪艳飞史娜徐效陵方岩雄张焜杜志云
Owner GUANGDONG UNIV OF TECH
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