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Method for preparing fatty acid alkyl ester by using long-chain alkyl sulfonic acid functional polyoxometalate as catalyst

A long-chain alkyl sulfonic acid, fatty acid alkyl ester technology, applied in the direction of physical/chemical process catalyst, carboxylate preparation, organic compound/hydride/coordination complex catalyst, etc. The problem of large amount of ionic liquid is used to achieve the effect of easy post-processing, short reaction time and high yield

Inactive Publication Date: 2013-03-27
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A bissulfonic acid functionalized ionic liquid (N,N,N',N'-tetramethyl-N,N'-dipropanesulfonic acid ethylenediamine bisulfate) reported in the literature was used to catalyze the reaction of free fatty acids with methanol , Ethanol esterification process showed good temperature-controlled liquid-liquid separation performance (ACS Catal.2011,1,42-47), and achieved a high FAME yield, but the ionic liquid in the reaction process The dosage is relatively large (ionic liquid is 50% of the molar ratio of free fatty acid); Professor Wang Jun reported a series of sulfonic acid functionalized heteropolyacid salts with ionic liquid structure (CN101574667A, Angew.Chem.2009, 121, 174-177), At the same time, it showed an unusual reaction induction-self-separation effect in a series of esterification reactions. This study prepared a new class of organic-inorganic composite catalytic materials based on heteropolyacids, which are both homogeneous and heterogeneous catalysts. The advantages of these materials have injected new vitality into the current hot research "organic-inorganic hybrid catalytic materials", but there are no reports on the use of this type of catalyst for the esterification of free fatty acids and low molecular weight alcohols to prepare FAME.

Method used

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  • Method for preparing fatty acid alkyl ester by using long-chain alkyl sulfonic acid functional polyoxometalate as catalyst
  • Method for preparing fatty acid alkyl ester by using long-chain alkyl sulfonic acid functional polyoxometalate as catalyst
  • Method for preparing fatty acid alkyl ester by using long-chain alkyl sulfonic acid functional polyoxometalate as catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The first step preparation of long-chain alkylsulfonic acid functionalized heteropolyacid salt

[0029] Add sodium hydride (0.06mol) and tetrahydrofuran (100mL) to a 250mL three-necked flask successively under nitrogen atmosphere, then slowly add imidazole (0.05mol) tetrahydrofuran solution (40mL) dropwise at 40°C, continue to The reaction was stirred for 4 hours; then the reaction temperature was raised to 60° C., and hexadecane bromide (0.05 mol) was slowly dropped to continue the constant temperature reaction for 12 hours. After the reaction, the solvent was removed under reduced pressure to obtain cetyl imidazole. Add cetyl imidazole (0.035mol) and acetone (60mL) into a 250mL three-necked flask, slowly add 1,3-propane sultone (0.035mol) dropwise at 40°C, and react at a constant temperature for 8 hours after the addition is complete. Zwitterionic compounds were obtained by filtration. Take the zwitterionic compound (0.030mol) into a three-necked flask, slowly add H...

Embodiment 2-7

[0033] Except following difference, all the other are identical with embodiment 1, and reaction time is according to table 1.

[0034] Table 1

[0035] Example

Embodiment 8-11

[0037] Except the following differences, all the other are the same as Example 1, and the molar ratio of ethanol and fatty acid is according to the consumption of Table 2 respectively.

[0038] Table 2

[0039] Example

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Abstract

The invention discloses a method for preparing fatty acid alkyl ester (FAME) by using long-chain alkyl sulfonic acid functional polyoxometalate as a catalyst. The method is characterized by comprising the following steps of: using long-chain alkyl sulfonic acid functional polyoxometalate as a catalyst in an esterification of fatty acid, methyl alcohol and ethanol, distilling after ending reaction to remove low molecular weight alcohol, cooling and automatically separating the catalyst from a reaction mixture to obtain efficient fatty acid ester instantly. The catalyst can be repeatedly used. The method provided by the invention has the advantages of high product yield, less catalyst dosage, high activity, short reaction time and no environmental pollution, thereby being an efficient and environment-friendly preparation method of fatty acid ester.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a method for preparing fatty acid alkyl esters by using long-chain alkylsulfonic acid functionalized heteropolyacid salts as catalysts. Background technique [0002] The rapid development of the world economy has made people more and more dependent on fossil resources, and its high-intensity development and utilization have led to the depletion of its reserves and the soaring price [Progress In Chemistry, 2006, 18 (2-3): 131-141 ], and the exploitation and use of a large number of fossil resources has brought serious environmental pollution, so it is imperative to develop clean and renewable energy to supplement and replace it. As a renewable and degradable new clean energy, biodiesel has attracted widespread attention [Bioresource Technology, 1999, 70:1-15.], and is expected to become an important substitute for fossil fuels. [0003] The main components of biodiesel are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/003B01J31/18B01J31/16
Inventor 刘秀梅刘静高艳安
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI