Preparation method of N-alkyl conjugated ion type quaternary ammonium salt

A technology of conjugated ions and quaternary ammonium salts, which is applied in the field of preparation of quaternary ammonium salt phase transfer catalysts, can solve the problems of large amount of reaction solvent used, reaction yield greatly affected by ambient humidity, and lengthy catalyst synthesis process steps. Achieve the effect of reducing production cost, shortening reaction time, and increasing reaction rate

Inactive Publication Date: 2014-02-05
SHANGHAI HUAYI GRP CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Regarding the preparation method of N-alkyl conjugated ionic quaternary ammonium salt in the prior art, the catalyst synthesis process steps are tedious, the reaction solvent, especially the halogen

Method used

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  • Preparation method of N-alkyl conjugated ion type quaternary ammonium salt
  • Preparation method of N-alkyl conjugated ion type quaternary ammonium salt
  • Preparation method of N-alkyl conjugated ion type quaternary ammonium salt

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Carbonylation reaction: In a flask equipped with a stirrer, a reflux condenser, and a constant pressure dropping funnel, add 225g of an aqueous solution of dimethylamine (40%), and dropwise add 118.7g of bis(trichlorohydrin) under vigorous stirring at 10°C. Toluene solution of methyl)carbonate, and adding 220g of acid-binding agent triethylamine, after the dropwise addition, rise to room temperature and stir for 4h, separate the organic phase, extract the water phase with toluene, combine the organic phases, and distill under reduced pressure to obtain tetramethyl Base urea 95g, yield 80%, purity 98%.

[0035] Chlorination reaction: In a flask equipped with a stirrer, a reflux condenser, and a constant pressure dropping funnel, add 30 g of the above-mentioned tetramethylurea, 30 g of toluene, and add 30 g of bis(trichloromethyl)carbonate dropwise at 5°C. The toluene solution was added dropwise for 4h, raised to room temperature and stirred for 2h. Filter and wash the f...

Embodiment 2

[0038] In a flask equipped with a stirrer, a reflux condenser, and a constant pressure dropping funnel, add 146g of diethylamine, slowly add dropwise a toluene solution containing 120g of bis(trichloromethyl)carbonate under vigorous stirring at 5°C, and Add 185 g of acid-binding agent pyridine. After the dropwise addition, raise to room temperature and stir for 4 h, and distill under reduced pressure to obtain tetraethylurea. Yield 91%, purity 98%.

[0039] In a flask equipped with a stirrer, a reflux condenser, and a constant pressure dropping funnel, add 43 g of the above-mentioned tetraethylurea, 40 g of toluene, and dropwise add a toluene solution containing 30 g of bis(trichloromethyl)carbonate at 5° C. Add dropwise for 4h, rise to room temperature and stir for 2h. After filtering, the filter cake was washed with toluene to obtain 41 g of chlorinated salt.

[0040] Dissolve the chlorinated salt in 60g of dichloromethane, add 50g of tetramethylguanidine dropwise at 10°C,...

Embodiment 3

[0042] In a flask equipped with a stirrer, a reflux condenser, and a constant pressure dropping funnel, add 130 g of dibutylamine, and slowly add a toluene solution containing 60 g of bis(trichloromethyl)carbonate dropwise under vigorous stirring at 5°C, and Add 125 g of acid-binding agent triethylamine, after the dropwise addition, raise to room temperature and stir for 4 h, then distill under reduced pressure to obtain tetrabutylurea. Yield 90%, purity 98%.

[0043] In a flask equipped with a stirrer, a reflux condenser, and a constant pressure dropping funnel, add 73 g of the above-mentioned tetrabutylurea, 40 g of toluene, and add dropwise a toluene solution containing 30 g of bis(trichloromethyl)carbonate at 5° C. Add dropwise for 4h, rise to room temperature and stir for 2h. After filtering, the filter cake was washed with toluene to obtain 70 g of chlorinated salt.

[0044] Dissolve the chlorinated salt in 60g of dichloromethane, add 50g of tetramethylguanidine dropwi...

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Abstract

The invention discloses a preparation method of N-alkyl conjugated ion type quaternary ammonium salt. Dialkylamine, bis(trichloromethyl)carbonate and tetramethyl guanidine are used as raw materials which are subjected to carbonylation, chlorination, condensation and neutralization reactions to synthesize an alkyl quaternary ammonium salt phase transfer catalyst, namely the N-alkyl conjugated ion type quaternary ammonium salt. In the process, since the bis(trichloromethyl)carbonate replaces highly-toxic phosgene, the safety and environmental protection hidden danger in catalyst synthesis are greatly reduced from the source, and the problem that phosgene is hard to accurately quantify in a reaction process is effectively solved; the reaction product alkyl quaternary ammonium salt is directly crystallized in toluene and separated out, has the purity of as high as 99%, and can be applied to a halogen exchange reaction. The reaction conditions of the process are mild, the process is safe and environment-friendly, the yield is high, the cost is low, and the activity of a finished product of the catalyst is good.

Description

technical field [0001] The present invention relates to a preparation method of a quaternary ammonium salt phase transfer catalyst, in particular to a preparation method of an N-alkyl conjugated ionic quaternary ammonium salt, which can be used in the preparation of aromatic fluorine-containing compounds by the halogen exchange method, and is especially suitable for It is used in the synthesis of some aromatic fluorine-containing compounds that require high temperature reactions. Background technique [0002] N-alkyl conjugated ionic quaternary ammonium salt is a new phase transfer catalyst newly developed in recent years, which can be applied to the preparation of aromatic fluorine-containing compounds by halogen exchange method. Compared with other commonly used phase transfer catalysts such as quaternary ammonium salts, quaternary phosphonium salts, crown ethers and polyether phase transfer catalysts, which have low activity and easy decomposition at high temperature, N-a...

Claims

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Application Information

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IPC IPC(8): C07C279/12C07C277/08C07C253/30C07C255/50C07C255/51C07C205/12C07C201/12C07C47/55C07C45/63B01J31/02
Inventor 杨伟领兰红丽宋芬施险峰赖春波廖本仁揭元萍
Owner SHANGHAI HUAYI GRP CO
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