Method for synthesizing biphenyl 4,4'-dicarboxylic acid from p-chlorotoluene

A technology of biphenyl dicarboxylic acid and p-chlorotoluene, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylate and other directions, can solve the problems of large environmental pollution, numerous steps, complicated operations, etc., so as to reduce environmental pollution. , The effect of simple and convenient operation and high reaction yield

Inactive Publication Date: 2013-04-03
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
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Problems solved by technology

However, the reaction conditions of this method are harsh, and generally require high temperature and high pressure, and the presence of bromide ions will cause serious corrosion.
4,4′-Dimethylbiphenyl itself is difficult to prepare, the market price is relatively high, and domestic research on it is less
However, the above method has low yield and high cost; or has many steps, complicated operation, and high requirements on reaction conditions; or has disadvantages such as large environmental pollution, and it is still difficult to realize industrialized production.

Method used

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  • Method for synthesizing biphenyl 4,4'-dicarboxylic acid from p-chlorotoluene
  • Method for synthesizing biphenyl 4,4'-dicarboxylic acid from p-chlorotoluene

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Embodiment 1

[0027] 1) Inert gas (N 2 ) under protection, 0.3g is now filing magnesium powder, 5mL p-chlorotoluene is added in the dry there-necked flask, 81mL NiCl is added 2 , 164mg PPh 3 , add a reflux condensing device, heat to 180 ° C, react for 2.5 h, and cool to room temperature. 2 mL of methanol was added for quenching, 20 mL of ethyl acetate was added for extraction, celite was filtered, washed twice with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and the unreacted p-chlorotoluene was recovered to obtain 1.4 mg of pale yellow solid , the yield is 63%. The crude product has a purity of more than 90%, and is recrystallized with methanol to obtain a white slightly yellow crystalline solid with a HPLC purity of more than 98%. Melting point: 119-121℃

[0028] 2) put 2mmol of the 4,4'-dimethylbiphenyl obtained in step 1) into a dry single-neck bottle, add 0.4mmol of NHPI, 5mg of Co(OAC) 2 , 5mg Mn(OAC) 2 , add 6 mL of acetic acid as a solvent, and...

Embodiment 2

[0030] With embodiment 1, wherein the difference is that the amount of p-chlorotoluene added in step 1) is 4.4mL, and the ligand PPh 3 328mg, the reaction reflux time was 4h, and finally 1.54mg of 4,4'-dimethylbiphenyl was obtained, and the yield was 68.5%.

Embodiment 3

[0032] With embodiment 1, wherein the difference is that the amount of p-chlorotoluene added in step 1) is 5.7mL, and the ligand PPh 3 328mg, the reaction reflux time was 3h, and finally 1.78mg of 4,4'-dimethylbiphenyl was obtained, and the yield was 79%.

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Abstract

The present invention provides a method for preparing biphenyl 4,4'-dicarboxylic acid, and belongs to the technical field of organic synthesis. The method comprises: adopting p-chlorotoluene as a raw material, adding a metal magnesium, a catalyst and a ligand, and synthesizing 4,4'-dimethylbiphenyl through a one-pot method; and introducing oxygen to the 4,4'-dimethylbiphenyl to carry out oxidation, adding a certain amount of the catalyst, adopting acetic acid as a solvent, heating, evaporating the solvent after completing the reaction, and carrying out water washing and drying to obtain the biphenyl 4,4'-dicarboxylic acid. According to the present invention, the p-chlorotoluene is adopted as the starting material, the solvent-free one-pot method is adopted to synthesize the 4,4'-dimethylbiphenyl so as to provide advantages of low cost, high yield, simple operation and easy purification; free radical oxidation of oxygen molecules is adopted in oxidation of aromatic hydrocarbon alkyl into aromatic carboxylic acid, such that reaction conditions are relatively mild, and corrosion on the equipment is reduced; and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 4,4'-biphenyldicarboxylic acid from p-chlorotoluene, and belongs to the technical field of organic synthesis. Background technique [0002] 4,4'-biphenyl dicarboxylic acid (biphenyl 4,4'-dicarboxylic acid) is an important organic synthesis intermediate, which can be used in pharmaceuticals and polymer materials, especially in liquid crystal products that have developed rapidly in recent years. application. [0003] For its synthesis, it is mainly prepared by oxidation reaction with 4,4'-dialkylbiphenyl as raw material. Since the emergence of the MC method (US 2245528) for the liquid-phase catalytic oxidation of alkyl aromatics to produce aromatic carboxylic acids, this method has been widely used in industrial production. The method mainly uses alkyl aromatic hydrocarbon as raw material, uses cobalt-manganese-bromine ternary system as catalyst, C1-C6 aliphatic carboxylic acid (usually acetic acid) as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C63/333C07C51/265
Inventor 周智明孙稳稳黄海丰王凯刘应强
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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