Method for preparing glycerin ether from glycerol

A technology of glycerol ether and glycerol diether is applied in the field of preparation of glycerol ether, and can solve the problems of low yield, inconvenient transportation and storage, etc.

Inactive Publication Date: 2010-01-13
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

[0005] In recent years, glycerol and isobutylene are reacted under the catalysis of conventional acids such as alkylbenzenesulfonic acid, naphthalenesulfonic acid, heteropolyacid, molecular sieve, ion exchange resin, sulfuric acid and methanesulfonic acid to prepare di-tert-butyl glyceryl ether or tri-tert-butyl Glyceryl ether has many patents and literature reports (C.H.Zhou, J.N.Beltramini, Y.X.Fan, G.Q.Lu, Chem.Soc.Rev., 2008,37,527; A.Behr, J.Eilting, K.Irawadi, J. Leschinski, F.Lindner, Green Chem., 2008, 10, 13 and related citations), however, isobutene is a gas at normal temperature and pressure, and transportation and storage are very inconvenient
Patent US2007238905 (WO2007113776) reports the method for preparing glycerol ether from glycerol and alcohol under the catalysis of conventional acids such as alkylbenzenesulfonic acid, naphthalenesulfonic acid, heteropolyacid, molecular sieve, ion exchange resin, sulfuric acid and methanesulfonic acid, however, its The product is mainly monoglycerides, with very low yields (7-14%) of diglycerides and triglycerides

Method used

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  • Method for preparing glycerin ether from glycerol
  • Method for preparing glycerin ether from glycerol
  • Method for preparing glycerin ether from glycerol

Examples

Experimental program
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Effect test

Embodiment 1

[0023] In the 500ml stainless steel autoclave, add NaCl (mass fraction is 8%) and H 2 O (mass fraction is 10%) crude glycerin 22.4g (containing glycerin 0.2mol, 18.4g), 0.6mol (76.9g) ethyl cyclohexyl ether, 18.4mg p-toluenesulfonic acid and 100ml dimethyl sulfoxide, 0.1 MPa N 2 The reaction was carried out at 140°C for 8h under the atmosphere. After the reaction, the lower layer of the mixed solution was dimethyl sulfoxide and unreacted glycerin, which was recovered and reused. The upper layer was evaporated to distill ethyl cyclohexyl ether and washed with water (20ml×3) to obtain 14.0 g of dicyclohexyl glycerin ether, with a yield of 27.3 %. HRMS (EI): C 15 h 28 o 3 (M + ): 256.2022, calculated value: 256.2038.

Embodiment 2

[0025] Add 0.2mol (18.4g) glycerol, 2mol (174.6g) methyl tert-butyl ether and 1.84g Amberlyst 35 into a 500ml stainless steel autoclave, and react at 50°C for 48h. After the reaction, the mixture was filtered, and the lower layer of the filtrate was unreacted glycerin, which was recovered and reused. The upper layer was evaporated to remove methyl tert-butyl ether and washed with water (20ml×3) to obtain 14.5 g of di-tert-butyl glycerol ether, with a yield of 35.5%. . HRMS (EI): C 11 h 24 o 3 (M + ): 204.1730, calculated value: 204.1725.

Embodiment 3

[0027] Add 0.4mol (36.8g) glycerol, 2mol (174.6g) methyl tert-butyl ether and 368mg NR50, 0.1MPaN 2The reaction was carried out at 100°C for 16h under the atmosphere. After the reaction, the mixture was filtered, and the lower layer of the filtrate was unreacted glycerin, which was recovered and reused. The upper layer was evaporated to remove methyl tert-butyl ether and washed with water (20ml×3) to obtain 13.4g of di-tert-butyl glycerol ether, with a yield of 16.4%. . HRMS (EI): C 11 h 24 o 3 (M + ): 204.1730, calculated value: 204.1725.

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Abstract

The invention relates to a method for preparing glycerin ether from glycerol. The glycerol reacts with ether, alcohol or olefinic hydrocarbon in the existence of a catalyst to obtain di-tert-butyl glycerin ether, tri-tert-butyl glycerin ether and other glycerin ethers which can be used as diesel fuel additives, antibacterial agents, flavoring agents, humectants, emulsifying agents and surfactants at a high yield.

Description

technical field [0001] The invention relates to the preparation of glycerol ether, in particular to a method for preparing glycerol ether from glycerin. Background technique [0002] As the world's fossil energy reserves are decreasing day by day, the international fossil energy prices have continued to rise, and energy supply has become one of the focuses of global attention. my country is a country with a serious shortage of fossil energy resources. The fossil energy resources are very limited and need to be imported in large quantities. With the decrease of fossil energy resources, the problem of energy supply in our country will become more and more prominent. If this problem is not solved properly, it will seriously affect the development of national economy and national security. On the other hand, the use of fossil energy will have a great negative impact on the earth's ecological environment. Therefore, the development of green and renewable energy resources has att...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/01C07C41/14C07C41/06C07C43/10
CPCY02P20/54
Inventor 李德财黄义争于维强徐杰
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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