Method for preparing carboxylic ester

A technology of carboxylic acid ester and carboxylic acid, applied in the field of preparation of carboxylic acid ester, can solve the problems of oxidation of final product, deep color of ester product, low temperature of use of cationic resin, etc., so as to avoid the increase of energy consumption cost and improve esterification. Selectivity, the effect of reducing production costs

Inactive Publication Date: 2010-09-22
BEIJING SHIDA HUADING TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After the esterification reaction is completed, the protonic acid remaining in the reaction system will easily cause the final product to be partially oxidized during the separation process of the reaction product, and side reactions will occur. The obtained ester product has a dark color and the yield will also be affected.
In addition, protonic acid will corrode equipment, and the discharge of a large amount of waste acid will pollute the environment
Solid catalysts such as solid acids and ion exchange resins have been successfully explored as a new generation of esterification catalysts to replace protonic acids, but there are also shortcomings. For example, solid superacids are used as catalysts, with many by-products and easy loss of active centers. The reaction process is relatively complicated; the allowable use temperature of cationic resin is low, and the scope of application is also limited to a certain extent
Whether solid acid or ion exchange resin is used to catalyze the formation reaction of ester, the problem of mass transfer resistance in the process of heterogeneous catalytic reaction must be solved, and the corresponding process and reactor design are also relatively complicated.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of sec-butyl acetate in embodiment 1.1-(3-sulfonic acid group)-propyl group-2-pyrrolidone bisulfate ionic liquid

[0038] 1) Take equimolar 2-pyrrolidone and 1,3-propane sultone, use anhydrous ether as solvent, stir at room temperature for 20 hours, filter, wash with methanol, and vacuum dry to obtain a white solid powder ionic liquid Precursor: Add an equimolar amount of concentrated sulfuric acid dropwise to the ionic liquid precursor, stir at 80°C for 8 hours, then wash with ethyl acetate, and dry at 80°C under vacuum for 1 to 3 hours to obtain a yellow-brown viscous Ionic liquid [C 3 SO 3 Hnhp]HSO 4 .

[0039]2) Take 100 mmol of 1-(3-sulfonic acid)-propyl-2-pyrrolidone bisulfate ionic liquid prepared in step 1), add 50 mmol of acetic acid at room temperature, and place in an autoclave. Then add acetic acid in the still according to the flow rate of 150mmol / h, add 1-butene in the still according to the flow rate of 450mmol / h simultaneously, at 105 ℃, th...

Embodiment 2

[0040] Synthesis of diisopropyl adipate in embodiment 2.1-(4-sulfonic acid group)-butyl-2-pyrrolidone bisulfate ionic liquid

[0041] 1) Take equimolar 2-pyrrolidone and 1,4-butane sultone, use anhydrous ether as solvent, stir at room temperature for 20 hours, filter, wash with methanol, and vacuum dry to obtain white solid powder ion Liquid precursor; add an equimolar amount of concentrated phosphoric acid to the ionic liquid precursor dropwise, stir at 80°C for 8 hours, then wash with ethyl acetate, and dry under vacuum at 80°C for 1 to 3 hours to obtain a yellow-brown viscous thick ionic liquid [C 4 SO 3 Hnhp]H 2 PO 4 .

[0042] 2) Take 100 mmol of 1-(4-sulfonic acid)-butyl-2-pyrrolidone bisulfate ionic liquid prepared in step 1), add 50 mmol of adipic acid at room temperature, and place in an autoclave. Then replenish adipic acid in the still according to the flow rate of 150mmol / h, add propylene in the still according to the flow rate of 700mmol / h simultaneously, at ...

Embodiment 3

[0043] Embodiment 3: Synthesis of diisopropyl glutarate in 1-methylimidazolium bisulfate ionic liquid

[0044] 1) in the there-necked flask that stirrer is housed, add 75ml 1-methylimidazoles, under ice-bath condition, slowly drip the concentrated sulfuric acid of equimolar amount with dropping funnel, after dropping, form a large amount of white solids, in Stir at room temperature for 22 hours, as the reaction proceeds under stirring, the solid gradually disappears, and then washed with ethyl acetate, and finally vacuum-dried at 0.01MPa and 80°C for 8 hours, the final product is a light yellow transparent viscous liquid, namely It is the final synthesized 1-methylimidazolium bisulfate ionic liquid.

[0045] 2) Take 100 mmol of 1-methylimidazolium bisulfate ionic liquid prepared in step 1), add 50 mmol of glutaric acid at room temperature, and place in an autoclave. Then supplement glutaric acid in the still according to the flow rate of 150mmol / h, add propylene in the still ...

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PUM

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Abstract

The invention provides a method for preparing carboxylic ester. After liquid-phase ionic liquid at room temperature is taken as a catalyst and an extracting agent at the same time to catalyze the reaction of olefin and carboxylic acid to generate carboxylic ester, the generated carboxylic ester is separated from carboxylic acid which does not react. During the whole reaction, the molar ratio of carboxylic acid to ionic liquid to olefin in a reaction system is always kept at 0.2-5:1:0.1-10; absolute pressure is controlled between 0.05 and 5.0 MPa; reaction temperature is controlled between 10 and 110 DEG C; and the space velocity of the carboxylic acid added during the reaction is controlled between 0.1 and 500. The method has the advantages of further rasing the conversion rate of carboxylic acid, reducing production cost and reducing pollution caused for environment.

Description

technical field [0001] The invention relates to a method for preparing a green and efficient carboxylate. Background technique [0002] Carboxylate is a very important organic chemical product, which can be widely used in many chemical production processes as spices, food additives, plasticizers, defoamers and good organic solvents. The preparation of carboxylic acid esters mostly adopts the method of acid alcohol esterification, which has high cost of raw materials and generates a certain amount of water. Since the acid alcohol esterification reaction itself is a reversible equilibrium reaction, in order to achieve a relatively high conversion rate of the raw material carboxylic acid and alcohol, it is necessary to consume a large amount of energy to remove the water generated during the reaction from the reaction system. In addition, traditional esterification methods mostly use strong acids (such as concentrated sulfuric acid, etc.) as catalysts to achieve. After the en...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/42C07C69/44C07C69/14C07C67/04B01J31/02
Inventor 赵辉丁雯婧张新功杨朝合楚文斌韩占辉
Owner BEIJING SHIDA HUADING TECH
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