CN105330532B - To the preparation method of methyl benzoyl chloride - Google Patents
To the preparation method of methyl benzoyl chloride Download PDFInfo
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- CN105330532B CN105330532B CN201510932580.2A CN201510932580A CN105330532B CN 105330532 B CN105330532 B CN 105330532B CN 201510932580 A CN201510932580 A CN 201510932580A CN 105330532 B CN105330532 B CN 105330532B
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- methyl benzoyl
- benzoyl chloride
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/64—Separation; Purification; Stabilisation; Use of additives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to technical field of organic synthesis, and in particular to a kind of preparation method to methyl benzoyl chloride.The preparation method is as follows：In organic solvent, p-methylbenzoic acid and thionyl chloride react under the effect of the catalyst, after reaction, through normal pressure, are evaporated under reduced pressure to methyl benzoyl chloride.Present invention process is simple, and reaction speed is fast, and low energy consumption, and tail gas is disposable, and solvent for use and thionyl chloride are recyclable, and the product purity distilled is high, and yield is also high, it is easy to accomplish industrialized production.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of preparation method to methyl benzoyl chloride.
Background technology
It is a kind of important chemical raw material to methyl benzoyl chloride, for fields such as medicine, pesticide, photosensitive material, dyestuffs.
With the rapid development of modern polymer chemistry and materials chemistry, it is increasingly becoming one of research field most popular in the world,
Using also more and more extensive.
In the prior art, it uses p-methylbenzoic acid for raw material, reacts and be made to first with phosphorus oxychloride (or phosphorus pentachloride)
Base chlorobenzoyl chloride, yield 85%.It is more but there are impurity, and the problem of difficult separation, product purity is also relatively low.
Invention content
In view of the deficiencies of the prior art, the object of the present invention is to provide a kind of suitable for industrialized production to toluyl
The preparation method of chlorine, simple for process, reaction speed is fast, and low energy consumption, and product purity is high, high income.
Preparation method of the present invention to methyl benzoyl chloride, in organic solvent, p-methylbenzoic acid and chlorination
Sulfoxide reacts under the effect of the catalyst, after reaction, through normal pressure, is evaporated under reduced pressure to methyl benzoyl chloride.
Wherein：
The organic solvent is dichloromethane, dichloroethanes, carbon tetrachloride, tetrahydrofuran, chlorobenzene, toluene or dimethylbenzene
One or more of.
The molar ratio of the p-methylbenzoic acid and thionyl chloride is 1：1.1~1.5.
The catalyst is the phase transfer catalysts such as tetrabutyl ammonium halide, benzyl triethyl ammonium ammonium halide or triphenylphosphine oxide
One or more of.
The reaction temperature is 60~115 DEG C, and the reaction time is 10~15 hours.
The vacuum distillation temperature is 115~120 DEG C, and pressure is -0.095MPa.
In conclusion beneficial effects of the present invention are as follows：
(1) the raw material thionyl chloride that uses of the present invention is liquid under room temperature, released in reaction process gaseous state HCl and
SO2, it is easy to separate from system in time, makes reaction be easy to carry out, reaction is thorough, is a kind of ideal chlorinating agent.
(2) organic solvent and excessive thionyl chloride are isolated in preparation method elder generation air-distillation, then are evaporated under reduced pressure to
To high purity product, the chromatographic content of products obtained therefrom is 99% or more, and yield is 95% or more.
(3) organic solvent and excessive thionyl chloride described in can be cost-effective with recovery.
(4) present invention process is simple, and reaction speed is fast, and low energy consumption, and tail gas is disposable, more environmentally friendly, is easy to industrialized production.
Specific implementation mode
With reference to embodiment, the present invention will be further described.
All raw materials used in embodiment are purchased in market unless otherwise specified.
Embodiment 1
50g p-methylbenzoic acids, 100g carbon tetrachloride and catalyst tetrabutylammonium chloride 0.15g are added in reaction bulb,
It stirs evenly, it is made fully to dissolve, be slow added into 48.1g thionyl chlorides, 115 DEG C of insulated and stirreds 10 hours.After reaction,
First air-distillation removes solvent and excessive thionyl chloride, then is evaporated under reduced pressure to obtain product 54.5g, chromatographic content 99.2%,
Calculated yield is 96.0%.
The vacuum distillation temperature is 115 DEG C, and pressure is -0.095MPa.
Embodiment 2
60g p-methylbenzoic acids, 50g dichloroethanes, 70g dichloromethane and catalyst triphenyl oxygen are added in reaction bulb
Phosphine 0.05g, benzyl triethyl ammonium bromide 0.1g, tetrabutylammonium chloride 0.03g, stir evenly, it are made fully to dissolve, then slowly add
Enter 62.9g thionyl chlorides, 100 DEG C of insulated and stirreds 12 hours.After reaction, first air-distillation removes solvent and excessive chlorination
Sulfoxide, then be evaporated under reduced pressure to obtain product 65.1g, chromatographic content 99.1%, calculated yield 95.6%.
The vacuum distillation temperature is 119 DEG C, and pressure is -0.095MPa.
Embodiment 3
80g p-methylbenzoic acids, 60g toluene, 40g dimethylbenzene, 60g chlorobenzenes and the catalyst tetrabutyl are added in reaction bulb
Ammonium bromide 0.1g, benzyl triethyl ammonium bromide 0.14g, stir evenly, it are made fully to dissolve, and are slow added into 90.9g protochlorides
Sulfone, 80 DEG C of insulated and stirreds 14 hours.After reaction, first air-distillation removes solvent and excessive thionyl chloride, then depressurizes steaming
It evaporates to obtain product 86.5g, chromatographic content 99.2%, calculated yield 95.2%.
The vacuum distillation temperature is 120 DEG C, and pressure is -0.095MPa.
Embodiment 4
100g p-methylbenzoic acids, 200g tetrahydrofurans and catalyst benzyltriethylammoinium chloride are added in reaction bulb
0.15g, triphenylphosphine oxide 0.15g, stir evenly, it are made fully to dissolve, and are slow added into 131.1g thionyl chlorides, 60 DEG C of heat preservations
Stirring 15 hours.After reaction, first air-distillation removes solvent and excessive thionyl chloride, then is evaporated under reduced pressure to obtain product
108.8g, chromatographic content 99.3%, calculated yield 95.8%.
The vacuum distillation temperature is 117 DEG C, and pressure is -0.095MPa.
Claims (1)
1. a kind of preparation method to methyl benzoyl chloride, it is characterised in that：Be added in reaction bulb 100g p-methylbenzoic acids,
200g tetrahydrofurans and catalyst benzyltriethylammoinium chloride 0.15g, triphenylphosphine oxide 0.15g, stir evenly, and keep it fully molten
Solution, is slow added into 131.1g thionyl chlorides, 60 DEG C of insulated and stirreds 15 hours；After reaction, first air-distillation removes solvent
With excessive thionyl chloride, then it is evaporated under reduced pressure to obtain product 108.8g, chromatographic content 99.3%, calculated yield 95.8%；Institute
The vacuum distillation temperature stated is 117 DEG C, and pressure is -0.095MPa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510932580.2A CN105330532B (en) | 2015-12-14 | 2015-12-14 | To the preparation method of methyl benzoyl chloride |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510932580.2A CN105330532B (en) | 2015-12-14 | 2015-12-14 | To the preparation method of methyl benzoyl chloride |
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| Publication Number | Publication Date |
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| CN105330532A CN105330532A (en) | 2016-02-17 |
| CN105330532B true CN105330532B (en) | 2018-07-20 |
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| CN201510932580.2A Active CN105330532B (en) | 2015-12-14 | 2015-12-14 | To the preparation method of methyl benzoyl chloride |
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| CN106045870B (en) * | 2016-07-07 | 2018-07-03 | 上海应用技术学院 | A kind of method for preparing amide |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101717333B (en) * | 2009-10-30 | 2012-08-22 | 周成云 | Preparation method of (-)-di(p-toluoyl)tartaric acid |
| CN102093291B (en) * | 2010-12-10 | 2012-10-24 | 上海应用技术学院 | Preparation method of N-[4-(triethyl aminomethyl) benzoyl] caprolactam bromide |
| CN103641706B (en) * | 2013-12-04 | 2015-08-05 | 山东凯盛新材料有限公司 | The preparation method of pyromellitic trimethylsilyl chloride |
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Address after: 255190 Yang Zhen, Zichuan District, Zibo City, Shandong Province Applicant after: Shandong Kaisheng New Materials Co.,Ltd. Address before: 255190 Yang Zhen, Zichuan District, Zibo City, Shandong Province Applicant before: SHANDONG KAISHENG NEW MATERIALS CO., LTD. |
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| CB03 | Change of inventor or designer information |
Inventor after: Zhang Congcong Inventor after: Zhang Le Inventor after: Zhang Taiming Inventor after: Bi Yixia Inventor after: Zhang Shanmin Inventor after: Xie Shengbin Inventor after: Xue Juqiang Inventor after: Zhang Liang Inventor before: Yang Deyao Inventor before: Zhang Taiming Inventor before: Bi Yixia Inventor before: Zhang Shanmin Inventor before: Xie Shengbin Inventor before: Xue Juqiang Inventor before: Song Liwei |
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