Method for oxidation preparation of substituted benzoic acid from substituted toluene in non-acid solvent

A non-acidic, benzoic acid technology, applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as environmental pollution, corrosion of equipment, industrial production difficulties, etc., to reduce environmental pollution and reduce equipment. Erosion, post-processing simple effects

Inactive Publication Date: 2004-09-01
EAST CHINA NORMAL UNIVERSITY
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Problems solved by technology

The oxidation method of the background technology is usually carried out by substituting toluene in a lower fatty acid, such as acetic acid and other acidic solvents. The acidity seriously corrodes the equipment, and a large amount of discharge causes environmental pollution and brings difficulties to industrial production.
In 1997, Yoshino et al. reported the catalytic oxidation method of alkylbenzene in acetonitrile on "Journal of Organic Chemistry", but the method was not ideal for the oxidation of alkylbenzene substituted by electron-withdrawing groups such as halogen
In 1998, Zhang Xiangfu reported the method of oxidizing toluene in 2-heptanone, nitrobenzene, butyl acetate, 2,5-hexanedione and dimethylformamide, but the highest yield was only 1.9%

Method used

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  • Method for oxidation preparation of substituted benzoic acid from substituted toluene in non-acid solvent
  • Method for oxidation preparation of substituted benzoic acid from substituted toluene in non-acid solvent

Examples

Experimental program
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Effect test

Embodiment 1

[0015] The substituted toluene is p-fluorotoluene, where the X group is, X=F.

[0016] 110g p-fluorotoluene was placed in a three-necked flask with a reflux condenser, and 37.5g Co(C 18 h 35 o 2 ) 2 , 4.9 g NH 4 Br, 7.7g AIBN and 25g dichlorobenzene, feed oxygen, stir, heat, control the temperature at 150 ° C, oxidize for 8 hours, let the reaction solution stand, cool to room temperature, the crude product is precipitated in solid form, filter, the crude product Recrystallized with water and ethanol to obtain 44.8 g of refined product p-fluorobenzoic acid with a yield of 32%.

Embodiment 2

[0018] The substituted toluene is p-chlorotoluene, where the X group is, X=Cl.

[0019] 126.5g p-chlorotoluene was placed in a three-necked flask with a reflux condenser, and 37.5g Co(C 18 h 35 o 2 ) 2 , 4.9 g NH 4 Br, 7.7g AIBN and 25g dichlorobenzene, feed oxygen, stir, heat, control the temperature at 150 ° C, oxidize for 8 hours, let the reaction solution stand, cool to room temperature, the crude product is precipitated in solid form, filter, the crude product is water Recrystallized with ethanol to obtain 103.3 g of refined product p-chlorobenzoic acid with a yield of 66%.

Embodiment 3

[0021] The substituted toluene is p-bromotoluene, where the X group is, X=Br.

[0022] 171g p-bromotoluene was placed in a three-necked flask with a reflux condenser, and 37.5g Co(C 18 h 35 o 2 ) 2 , 4.9 g NH 4 Br, 7.7g AIBN and 25g dichlorobenzene, feed oxygen, stir, heat, control the temperature at 150 ° C, oxidize for 9 hours, let the reaction solution stand, cool to room temperature, the crude product is precipitated in solid form, filter, the crude product Recrystallize with water and ethanol to obtain 185 g of refined product p-bromobenzoic acid with a yield of 92%.

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Abstract

A process for preparing substituted benzene carbonic acid through oxidization of substituted toluene molecule oxygen in non-acid solvent which relates to the field of organic chemical reaction process, wherein substituted toluene is used as raw material and dissolved in the miscible liquid of non-acid solvent, initiating agent and catalyst under constant pressure, the other steps includes, letting in oxygen, agitating, heating, stewing, cooling down to room temperature, evolution of rough product in the form of solid, filtering, recrystallization, obtaining the refined product, i.e. substituted benzoic acid, wherein the yield is 31%-96%.

Description

technical field [0001] The invention relates to a method for preparing substituted benzoic acid by oxygen oxidation of substituted toluene molecules in a non-acidic solvent, belonging to the technical field of organic chemical reaction methods. Background technique [0002] Various substituted benzoic acids are important intermediates in organic synthesis. The oxidation method of the background art is usually carried out by substituting toluene in a lower fatty acid, such as acetic acid and other acidic solvents. The acidity severely corrodes equipment, and a large amount of discharge causes environmental pollution and brings difficulties to industrial production. In 1997, Yoshino et al. reported the catalytic oxidation of alkylbenzenes in acetonitrile in the "Journal of Organic Chemistry", but the method was not ideal for the oxidation of alkylbenzenes substituted by electron-withdrawing groups such as halogens. In 1998, Zhang Xiangfu reported the method of...

Claims

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Application Information

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IPC IPC(8): C07C51/265C07C63/06
Inventor杨帆汤杰孙靖温孟嬴
OwnerEAST CHINA NORMAL UNIVERSITY