Method for preparing 4-methyl-4-trichloromethyl-2, 5-cyclohexadiene-1-ketone

A technology of trichloromethyl and cyclohexadiene, applied in the field of chemical intermediate preparation, can solve problems such as unfavorable industrial production, environmental protection and safety, harsh production conditions, etc., and achieves convenient industrial production, no irritating odor, and reduced reaction cost effect

Active Publication Date: 2015-06-24
TIANCHANG TIANJIA CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] For the reaction conditions of Method 1, carbon tetrachloride is used as both the reaction raw material and the reaction solvent. The amount of carbon tetrachloride is large and the reaction yield is low, which not only increases the reaction cost, but also is not environmentally safe. The product post-treatment process uses water vapor Distillation, the time to process the reaction is quite long, and the 20g-scale reaction requires five or six hours of steam distillation, and is accompanied by a strong pungent smell, so it is not conducive to industrial production
[0009] For the synthesis process of Method 2, although this route improves the product yield, it uses carbon disulfide with malodorous and low flash point as the reaction solvent, the process operation is dangerous, and the treatment process also uses steam distillation to obtain the product, so it is not conducive to Industrial production
[0010] In addition, a large amount of tar-like products will inevitably be produced i...

Method used

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  • Method for preparing 4-methyl-4-trichloromethyl-2, 5-cyclohexadiene-1-ketone
  • Method for preparing 4-methyl-4-trichloromethyl-2, 5-cyclohexadiene-1-ketone
  • Method for preparing 4-methyl-4-trichloromethyl-2, 5-cyclohexadiene-1-ketone

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Effect test

Embodiment 1

[0042] In this embodiment, a preparation method of 4-methyl-4-trichloromethyl-2,5-cyclohexadien-1-one comprises the following steps:

[0043] S1. Weigh 28g of aluminum trichloride and add it to 116g of dichloromethane, stir in the reaction bottle and cool down to 5°C; weigh 15g of p-cresol and dissolve it in 50g of dichloromethane, and place it in a constant pressure dropping funnel. Then slowly add it to the dichloromethane reaction system of aluminum trichloride. During the dropwise addition, the reaction temperature is 15°C. hour, the point plate reaction is complete;

[0044] Among them, p-cresol and carbon tetrachloride are used as raw materials to prepare 4-methyl-4-trichloromethyl-2,5-cyclohexadiene-1- Ketones, the reaction equation is as follows:

[0045]

[0046] S2. Cool the mixed solution prepared in S1 to room temperature, then slowly add it into 150 g of ice water, and stir for 15 minutes;

[0047] S3, liquid separation, wherein the liquid separation temperatu...

Embodiment 2

[0051] In this embodiment, a preparation method of 4-methyl-4-trichloromethyl-2,5-cyclohexadien-1-one comprises the following steps:

[0052] S1. Weigh 70g of aluminum trichloride and add it to 120g of dichloromethane, stir in the reaction bottle and cool down to 10°C; weigh 37g of p-cresol and dissolve it in 160g of dichloromethane, and place it in a constant pressure dropping funnel. Then slowly add it to the dichloromethane reaction system of aluminum trichloride. During the dropwise addition, the reaction temperature is 5°C. Less than 2 hours, the plate reaction is complete;

[0053] Among them, p-cresol and carbon tetrachloride are used as raw materials to prepare 4-methyl-4-trichloromethyl-2,5-cyclohexadiene-1- Ketones, the reaction equation is as follows:

[0054]

[0055] S2. Cool the mixed solution prepared in S1 to room temperature, then slowly add it to 320 g of ice water, and stir for 45 minutes;

[0056] S3, liquid separation, wherein the liquid separation t...

Embodiment 3

[0060] In this embodiment, a preparation method of 4-methyl-4-trichloromethyl-2,5-cyclohexadien-1-one comprises the following steps:

[0061] S1. Weigh 32g of aluminum trichloride and add it to 134g of dichloromethane, stir in the reaction bottle and cool down to 7°C; weigh 20g of p-cresol and dissolve it in 66g of dichloromethane, and place it in a constant pressure dropping funnel. Then slowly join in the dichloromethane reaction system of aluminum trichloride, when dropwise, reaction temperature is 12 ℃, after dropwise is finished, continue to add carbon tetrachloride 28g, raise temperature to 38 ℃, continue to stir for 3 hour, the point plate reaction is complete;

[0062] Among them, p-cresol and carbon tetrachloride are used as raw materials to prepare 4-methyl-4-trichloromethyl-2,5-cyclohexadiene-1- Ketones, the reaction equation is as follows:

[0063]

[0064] S2. Cool the mixed solution prepared in S1 to room temperature, then slowly add it to 200 g of ice water...

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Abstract

The invention discloses a method for preparing 4-methyl-4-trichloromethyl-2, 5-cyclohexadiene-1-ketone. The method comprises the following steps that p-cresol and carbon tetrachloride serve as a raw material, aluminum chloride serves as a catalyst, and hydrochloric ether serves as a solvent to have a reaction at the temperature of 33 DEG C to 45 DEG C; water is added into mixed liquor prepared in the S1 to carry out quenching reaction, and the quenching reaction time ranges from 15 min to 45 min; liquor separating is carried out, the liquor separating temperature ranges from 5 DEG C to 20 DEG C, the solvent is removed, and residue is obtained; alcoholic solutions and activated carbon are added into the obtained residue and stirred, the temperature ranges from 50 DEG C to 78 DEG C, the stirring time ranges from 0.5h to 1h, heat filtering is carried out, cooling is carried out until a solid body is not separated out, filtering and drying are carried out, and the 4-methyl-4-trichloromethyl-2, 5-cyclohexadiene-1-ketone is obtained. The preparation method is safe in technological operation, a purification technology is simple, the production period is short, industrialization production is facilitated, raw material cost is low, and the yield is stable.

Description

technical field [0001] The invention relates to the field of preparation of chemical intermediates, in particular to a preparation method of 4-methyl-4-trichloromethyl-2,5-cyclohexadien-1-one. Background technique [0002] 4-Methyl-4-trichloromethyl-2,5-cyclohexadien-1-one is an additive used in the electronics industry and has an important application prospect as a photoacid generator in electronic chemistry. [0003] The preparation method of 4-methyl-4-trichloromethyl-2,5-cyclohexadien-1-one is mainly prepared by Zincke-Suhl reaction at present, method one: Zincke and Suhl reported in 1906 that p-cresol and Aluminum trichloride is prepared by reacting in a carbon tetrachloride system. After the reaction is completed, the product is obtained by steam distillation, and the reaction yield is between 37-42%. [0004] The reaction formula of Method 1 is as follows: [0005] [0006] Subsequently, Melvin S.Newman and A.G.Pinkusd improved this method in 1954, the solvent wa...

Claims

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Application Information

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IPC IPC(8): C07C49/687C07C45/67
CPCC07C45/45C07C45/68C07C2601/16C07C49/687
Inventor 张春涛孙郁纪奉元
Owner TIANCHANG TIANJIA CHEM TECH
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