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A kind of synthetic method of o-, m-, p-methyl trifluoromethylbenzoate

A technology of methyl trifluoromethyl benzoate and methyl benzoic acid, which is applied in the field of organic synthesis, can solve the problems of high price, high toxicity, and high equipment requirements, and achieve less side reaction products, mild reaction mechanism, and high reaction yield high effect

Active Publication Date: 2020-05-01
ZIBO FEIYUAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are few studies on the synthesis of trifluoromethylbenzoic acid, the yield of the synthesis process is low, the price of the catalyst is high and the toxicity is high: U.S. Patent US 46 42399 introduces the use of m-toluoyl chloride as the starting material, but it has no effect on the synthesis process. To describe in detail, its product yield is low, and its chlorination reaction is mainly based on catalytic chlorination reaction
Chinese patent CN102351704A describes that m-toluyl chloride is used as the starting material, the photochlorination reaction is promoted by a solvent, and the fluorination reaction uses antimony trichloride, antimony pentachloride or a perfluorinated catalyst, the catalyst is highly toxic, and expensive
The reaction time of this method is long, and the reaction operation is difficult
The current process of methyl trifluoromethyl benzoate in the production enterprises has the disadvantages of high requirements for equipment, large pollution of three wastes, and low yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 Methyl o-trifluoromethylbenzoate

[0023] (1) Add 330 g of o-toluic acid into the reaction vessel, then add 360 g of thionyl chloride and 5 g of DMF, stir and heat for about 2 hours, and when no obvious gas is produced in the reaction vessel, raise the temperature to 90±5 °C Insulate for 2 h to complete the reaction, and then distill excess thionyl chloride under normal pressure at 100 °C. The o-toluyl chloride yield is 98.9%;

[0024] (2) Add 400 g of o-toluyl chloride into the photochlorination reactor, add 4 g of phosphorus pentachloride at low temperature and heat it, start to pass dry chlorine gas at 140 °C, and keep chlorine at 165±5 °C , the average rate is 0.6 g / min, and the tail gas is absorbed with 30% sodium hydroxide, and the reaction is completed to obtain o-trichloromethylbenzoyl chloride, and the yield is 86.7%;

[0025] (3) Inject 578.9 g of o-trichloromethylbenzoyl chloride liquid into the autoclave, inhale 1210 g of dry hydrogen fluoride, s...

Embodiment 2

[0028] Example 2 methyl m-trifluoromethylbenzoate

[0029] (1) Add 330 g of m-toluic acid into the reaction vessel, then add 360 g of thionyl chloride and 5 g of DMF, stir and heat for about 2 hours, and when there is no obvious gas generation in the reaction kettle, raise the temperature to 90±5 °C Insulate for 2 h to complete the reaction, and then distill excess thionyl chloride under normal pressure at 120 °C. m-toluoyl chloride yield is 98.9%;

[0030] (2) Add 400 g of m-toluoyl chloride into the photochlorination reactor, add 2 g of phosphorus pentachloride at low temperature and heat it, and start to pass dry chlorine gas at 140 °C, and keep chlorine at 165±5 °C , the average rate is 0.6 g / min, and the tail gas is absorbed with 20% sodium hydroxide, and the reaction is completed to obtain m-trichloromethylbenzoyl chloride, and the yield is 98.2%;

[0031] (3) Inject 655.5 g m-trichloromethylbenzoyl chloride solution into the autoclave, inhale 1854.2 g dry hydrogen flu...

Embodiment 3

[0034] Example 3 Methyl p-trifluoromethylbenzoate

[0035] (1) Take 330 g of p-toluic acid and add it to the reaction vessel, then add 360 g of thionyl chloride and 5 g of DMF, stir and heat for about 2 hours, and when there is no obvious gas generation in the reaction kettle, raise the temperature to 90±5 °C Insulate for 2 h to complete the reaction, and then distill excess thionyl chloride at 90 °C under normal pressure. m-toluoyl chloride yield is 99.0%;

[0036] (2) Add 400 g of p-toluoyl chloride into the photochlorination reactor, add 2 g of phosphorus pentachloride at low temperature and heat it, and start to pass dry chlorine gas at 140 °C, and keep warm at 155±5 °C to pass chlorine , the average rate is 0.6 g / min, and the tail gas is absorbed with 30% sodium hydroxide, and the reaction is completed to obtain p-trichloromethylbenzoyl chloride, and the yield is 97.6%;

[0037] (3) Inject 1,000 g of p-trichloromethylbenzoyl chloride liquid into the autoclave, inhale 2,...

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PUM

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Abstract

The invention provides a synthesis method of o-trifluoromethyl methyl benzoate, m-trifluoromethyl methyl benzoate and p-trifluoromethyl methyl benzoate. The synthesis method comprises the following steps: taking methyl benzoic acid as a raw material, carrying out acylating chlorination to obtain methylbenzoyl chloride, carrying out side-chain chlorination to obtain trichloromethyl benzoyl chloride, carrying out fluorination substitution to obtain trifluoromethyl benzoyl fluoride, and carrying out esterification to obtain a final product which is trifluoromethyl methyl benzoate. The synthesis method can be used for producing the o-trifluoromethyl methyl benzoate, the m-trifluoromethyl methyl benzoate and the p-trifluoromethyl methyl benzoate, is easily available in raw material, mild in reaction mechanism, high in reaction yield, few in reaction by-products, low in yield of three wastes and easy in treatment of three wastes, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a method for preparing ester compounds of trifluoromethylbenzenes, in particular to a method for preparing methyl o-, m-, and p-trifluoromethylbenzoate. Background technique [0002] Since the 1990s, the research on fluorine-containing fine chemicals in my country has been extremely active. At present, more than a hundred kinds of fluorine-containing organic intermediates and fine chemicals have been developed, especially the rapid development of fluorine-containing fine chemicals. Due to the special properties of fluorine atoms, organic fluorine compounds have high chemical stability, physiological activity, fat solubility and hydrophobicity, and have been widely used in the fields of medicine, pesticides and auxiliaries. At present, 30-40% of pesticides are fluorine-containing pesticides, and about 20% of pharmaceuticals are fluorine-containing drugs. [0003] O-, m-, p-trifluor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/14C07C69/76C07C51/58C07C63/70C07C51/62C07C51/60C07C63/04
CPCC07C51/58C07C51/60C07C51/62C07C67/14C07C69/76C07C63/70C07C63/04
Inventor 夏凯邢茂源刘翠晔
Owner ZIBO FEIYUAN CHEM CO LTD
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