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Thermo-sensitive paper sensitizer ethylene glycol diphenyl ether preparation method

A technology of ethylene glycol diphenyl ether and sensitizer, which is applied in the directions of ether preparation, ester reaction preparation of ether, organic chemistry, etc., can solve the problems of high production cost and low yield, etc., to reduce production cost and increase production. Cost, large implementation value, and socioeconomic effects

Active Publication Date: 2019-07-23
QUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the yield in the known method is not high, and the excess of reaction raw material 1,2-dibromoethane or 1,2-dichloroethane leads to high production cost

Method used

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  • Thermo-sensitive paper sensitizer ethylene glycol diphenyl ether preparation method
  • Thermo-sensitive paper sensitizer ethylene glycol diphenyl ether preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 15.7 g of bromobenzene (100 mmol) and 47 ml of DMF into the three-necked flask, and stir. Add 12.7 grams of sodium carbonate (120 mmol, 1.2 equivalents), 1.9 grams of cuprous iodide (10 mmol, 0.1 equivalents), 1.87 grams of 2,2'-bipyridine (12 mmol, 0.1 equivalents) and 7.4 grams of ethylene glycol (120 mmol, 1.2 eq), and the reaction mixture was stirred overnight at 100 °C. After recovering DMF under reduced pressure, 100 ml of water and 100 ml of toluene were added, the aqueous phase was extracted three times with 300 ml of toluene, and the organic layers were combined. Washing with water and 5% sodium carbonate successively. The organic phase was dried with anhydrous sodium sulfate, filtered, decolorized by activated carbon, and the organic solvent was evaporated to obtain 22 grams of crude product. The crude product was recrystallized from isopropanol and dried in vacuum to obtain 19.5 grams of product. The yield was 91%, and the purity was greater than 99%.

Embodiment 2

[0022] The basic operation is the same as in Example 1, except that the metal catalyst is 1.43 g of cuprous bromide (10 mmol, 0.1 equivalent). After the crude product was recrystallized, 17.8 g of the product was obtained with a yield of 83% and a purity of more than 99%.

Embodiment 3

[0024] The basic operation is the same as in Example 1, except that the metal catalyst is 2.2 grams of copper bromide (10 mmol, 0.1 equivalent). After the crude product was recrystallized, 15.6 g of the product was obtained with a yield of 73% and a purity of more than 99%.

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Abstract

The invention relates to a thermo-sensitive paper sensitizer ethylene glycol diphenyl ether preparation method. According to the preparation method, halogeno benzene and ethylene glycol are utilized as raw materials, any one or several of 2,2'-dipyridyl and derivatives of the 2,2'-dipyridyl is utilized as ligand, and under the existence of alkali and a solvent, Cu(I) or Cu(II) is utilized as a catalyst to prepare and obtain ethylene glycol diphenyl ether. Compared with the prior art, ethylene glycol and bromobenzene are utilized reaction raw materials, so that ethylene glycol diphenyl ether production cost is greatly reduced; in addition, the ligand 2,2'-dipyridyl can be recycled, so that production cost cannot be increased; thus, larger implement value and social economic benefit are achieved.

Description

technical field [0001] The invention relates to a preparation method of thermal paper sensitizer ethylene glycol diphenyl ether. Background technique [0002] As a new thermal paper sensitizer, ethylene glycol diphenyl ether is in great demand in the market. The current commonly used production method is to select 1,2-dibromoethane (Fine Chemical Industry, 2010, 27(5), 512-515; Journal of East China University of Science and Technology, 2012, 38(5), 529-536,566) or 1,2-Dichloroethane (CN1544406, CN103073398, CN102276432, CN104710287, JP2005145857) is prepared by reacting with corresponding phenol. However, the yield in the known method is not high, and the excessive amount of 1,2-dibromoethane or 1,2-dichloroethane as the reaction raw material leads to high production cost. Therefore, it is of great economic value to develop a safe and low-cost method for preparing ethylene glycol diphenyl ether. Contents of the invention [0003] The purpose of the invention is to seek...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/16C07C43/205
CPCC07C41/16C07C43/2055
Inventor 葛承胜吕延文任浩明周海谢艳
Owner QUZHOU UNIV
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