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Preparation method of 1-chloromethylnaphthalene

A technology for chloromethyl naphthalene and chloromethyl naphthalene crude products, applied in the directions of halogenated hydrocarbon preparation, chemical instruments and methods, sustainable manufacturing/processing, etc. Cumbersome, high energy consumption, to achieve the effect of improving yield and purity, reducing side reactions, and low energy consumption

Active Publication Date: 2022-02-01
河北海力香料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems of cumbersome operation, high energy consumption and low yield and purity of the prepared 1-chloromethylnaphthalene product in the existing method for preparing 1-chloromethylnaphthalene, the invention provides a 1-chloromethylnaphthalene The preparation method of methylnaphthalene mainly uses naphthalene and polyoxymethylene as raw materials, introduces specific Lewis acid and phase transfer catalyst in the reaction process, and uses high concentration hydrochloric acid as chlorine source and cocatalyst, effectively reduces the reaction time, Improved product yield and purity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The present embodiment provides a kind of preparation method of 1-chloromethylnaphthalene, comprises the steps:

[0042] Step a, naphthalene 128g (1mol), paraformaldehyde 60g (2mol), FeCl 3 3.25g (0.02mol), CuCl 2 2.69g (0.02mol), 3.42g (0.015mol) of benzyltriethylammonium chloride, and 214.7g (2.5mol) of hydrochloric acid solution with a mass concentration of 42.5% were mixed evenly, heated to 40°C for 3 hours, and kept for 3 hours. Place liquid separation, and wash the oil phase twice with 10wt% potassium carbonate solution and water respectively to obtain the crude product of 1-chloromethylnaphthalene;

[0043] Step b, add the crude 1-chloromethylnaphthalene into 192g of absolute ethanol, heat up to 26°C to dissolve, then cool down to -5°C at a rate of 0.5°C / 10min for crystallization for 2h, filter, and wash with absolute ethanol , the filter cake was put into a vacuum drying oven, and dried at 25mmHg and 35°C for 5h to obtain 171.5g of 1-chloromethylnaphthalene p...

Embodiment 2

[0045] The present embodiment provides a kind of preparation method of 1-chloromethylnaphthalene, comprises the steps:

[0046] Step a, naphthalene 128g (1mol), paraformaldehyde 60g (2mol), FeCl 3 3.25g (0.02mol), CuCl 21.35g (0.01mol), 2.28g (0.01mol) of benzyltriethylammonium chloride and 257.6g (3mol) of hydrochloric acid solution with a mass concentration of 42.5% were mixed evenly, heated to 45°C and kept for 3 hours, then cooled and left to stand Liquid separation, the oil phase was washed twice with 10wt% potassium carbonate solution and water respectively to obtain the crude product of 1-chloromethylnaphthalene;

[0047] Step b, add the crude 1-chloromethylnaphthalene into 160g of absolute ethanol, heat up to 27°C to dissolve, then cool down to -3°C at a rate of 0.6°C / 10min and keep it crystallized for 2h, filter, and wash with absolute ethanol , the filter cake was put into a vacuum drying oven, and dried at 25mmHg and 30°C for 6h to obtain 168.8g of 1-chloromethyln...

Embodiment 3

[0049] The present embodiment provides a kind of preparation method of 1-chloromethylnaphthalene, comprises the steps:

[0050] Step a, naphthalene 128g (1mol), paraformaldehyde 45g (1.5mol), FeCl 3 2.44g (0.015mol), CuCl 2 2.03g (0.015mol), 1.82g (0.008mol) of benzyltriethylammonium chloride, and 214.7g (2.5mol) of hydrochloric acid solution with a mass concentration of 42.5% were mixed uniformly, heated to 45°C for 4 hours, and then cooled and statically Place liquid separation, and wash the oil phase twice with 10wt% potassium carbonate solution and water respectively to obtain the crude product of 1-chloromethylnaphthalene;

[0051] Step b, add the crude 1-chloromethylnaphthalene into 128g of absolute ethanol, heat up to 28°C to dissolve, then cool down to -5°C at a rate of 0.8°C / 10min for crystallization for 2h, filter, and wash with absolute ethanol , the filter cake was put into a vacuum drying oven, and dried at 30 mmHg and 35° C. for 5 hours to obtain 168.5 g of 1-c...

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Abstract

The invention relates to the technical field of organic synthesis, and particularly discloses a preparation method of 1-chloromethylnaphthalene. The preparation method comprises the following steps: uniformly mixing naphthalene, paraformaldehyde, lewis acid, a phase transfer catalyst and a hydrochloric acid solution with the mass concentration of 42-43%, carrying out heat preservation reaction, standing for liquid separation, and washing an oil phase to obtain a 1-chloromethylnaphthalene crude product; adding the 1-chloromethylnaphthalene crude product into an alcohol solvent, heating for dissolving, cooling for crystallization, filtering, washing and drying to obtain a 1-chloromethylnaphthalene product, wherein the lewis acid is a mixture of ferric chloride and copper chloride; the phase transfer catalyst is one or two of benzyl trimethyl ammonium chloride or benzyl triethyl ammonium chloride. According to the method, the yield and the purity of the 1-chloromethylnaphthalene product are effectively improved through a simple process, the reaction time for preparing the 1-chloromethylnaphthalene is effectively shortened, rectification is not needed, only the alcohol solvent is needed for crystallization and purification, the energy consumption is low, the operation safety is high, and the market prospect is wide.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 1-chloromethylnaphthalene. Background technique [0002] 1-Chloromethylnaphthalene, also known as α-chloromethylnaphthalene, English name 1-chloromethylnaphthalene, melting point 32°C, boiling point 164°C~165°C (2.67kPa), refractive index 1.6370, density 1.180g / cm 3 , flash point >110°C, soluble in ether and benzene, and is a lacrimal irritant. 1-Chloromethylnaphthalene is an important intermediate in organic synthesis, which can be used to synthesize α-naphthaldehyde, 1-naphthaldehyde, 1-naphthylacetic acid, 1-naphthoyl chloride, 1-naphthaleneacetonitrile, 1-naphthaleneacetamide, 1-Naphthylmethylamine and other products. [0003] At present, 1-chloromethylnaphthalene is mainly prepared by chloromethylation of naphthalene, and the prepared product has complex components, usually containing naphthalene, 2-chloromethylnaphthalene and 1,4-dichl...

Claims

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Application Information

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IPC IPC(8): C07C17/32C07C17/392C07C22/04
CPCC07C17/32C07C17/392C07C22/04Y02P20/584
Inventor 朱玉梅张云堂于玉秀李文革张健闫琴
Owner 河北海力香料股份有限公司
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