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Synthesis method for 3,3',4,4'-biphenyltetracarboxylic acid

A biphenyltetracarboxylic acid and synthesis method technology, applied in the field of synthesis of 3,3',4,4'-biphenyltetracarboxylic acid, can solve the problems of unfriendly environment, increased production cost, complicated operation, etc., and achieve environmental friendliness , less waste, and simple operation

Active Publication Date: 2020-02-21
CHANGZHOU SUNLIGHT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The above methods, whether it is dehalogenation coupling or oxidative coupling, require the use of a relatively expensive catalytic system, resulting in increased production costs, and the operation is more complicated and environmentally unfriendly

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0035] The synthetic route of 3,3',4,4'-biphenyltetracarboxylic acid of this embodiment is as follows:

[0036] .

[0037] The specific method is as follows:

[0038] ①Add 91g of 4,4'-dimethylbiphenyl (0.5mol) into 1L of dichloromethane, cool in an ice-water bath, add 320g of aluminum trichloride (2.4mol) in batches, and control the temperature at 10-20°C 0.5 L of dichloromethane solution containing 110 g of succinic anhydride (1.1 mol) was added dropwise, and the solution was reacted at room temperature overnight, and the reaction of the raw materials was monitored by TLC.

[0039] After the reaction, cool in an ice-water bath, add dilute hydrochloric acid dropwise to the reaction liquid to quench the reaction, stir for 1 h, let stand to separate layers, separate the organic phase, and concentrate the organic phase to obtain a yellow oil.

[0040] ② Add 1L of pyridine and 4L of water to the yellow oil obtained in step ①, heat to 85-95°C, add 790g of potassium permanganate...

Embodiment 2）

[0043] The synthetic route of 3,3',4,4'-biphenyltetracarboxylic acid of this embodiment is as follows:

[0044] .

[0045] The specific method is as follows:

[0046] ①Add 91g of 4,4'-dimethylbiphenyl (0.5mol) into 1L of dichloromethane, cool in an ice-water bath, add 320g of aluminum trichloride (2.4mol) in batches, and control the temperature at 10-20°C 0.5 L of dichloromethane solution containing 125 g of glutaric anhydride (1.1 mol) was added dropwise, and the solution was reacted at room temperature overnight, and the reaction of raw materials was monitored by TLC.

[0047] After the reaction, cool in an ice-water bath, add dilute hydrochloric acid dropwise to the reaction liquid to quench the reaction, stir for 1 h, let stand to separate layers, separate the organic phase, and concentrate the organic phase to obtain a yellow oil.

[0048] ②Add 1L of pyridine and 4L of water to the yellow oil obtained in step ①, heat to 85-95°C, add 948g of potassium permanganate (6mo...

Embodiment 3）

[0051] The synthetic route of 3,3',4,4'-biphenyltetracarboxylic acid of this embodiment is as follows:

[0052] .

[0053] The specific method is as follows:

[0054]①Add 91g of 4,4'-dimethylbiphenyl (0.5mol) into 1L of dichloromethane, cool in an ice-water bath, add 320g of aluminum trichloride (2.4mol) in batches, and control the temperature at 10-20°C 0.5 L of dichloromethane solution containing 118 g of maleic anhydride (1.2 mol) was added dropwise, and the solution was reacted at room temperature overnight, and the reaction of raw materials was monitored by TLC.

[0055] After the reaction, cool in an ice-water bath, add dilute hydrochloric acid dropwise to the reaction liquid to quench the reaction, stir for 1 h, let stand to separate layers, separate the organic phase, and concentrate the organic phase to obtain a yellow oil.

[0056] ② Add 1L of pyridine and 4L of water to the yellow oil obtained in step ①, heat to 85-95°C, add 790g of potassium permanganate (5mol)...

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PUM

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Abstract

The invention discloses a synthesis method for 3,3',4,4'-biphenyltetracarboxylic acid. The synthesis method comprises the following steps: with 4,4'-dimethyl biphenyl as a starting raw material, subjecting the 4,4'-dimethyl biphenyl and cyclic anhydride as shown in a formula I which is described in the specification to a Friedel-Crafts acylation reaction so as to obtain an intermediate II, and carrying out an oxidation reaction so as to obtain the 3,3',4,4'-biphenyltetracarboxylic acid, wherein the cyclic anhydride as shown in the formula I is selected from the group consisting of succinic anhydride, glutaric anhydride, adipic anhydride and maleic anhydride. The method provided by the invention does not need an expensive catalytic system, so the production cost of synthesizing the 3,3',4,4'-biphenyltetracarboxylic acid is greatly reduced; the method provided by the invention is simple to operate, mild in reaction conditions, less in three wastes, easy in wastewater treatment and friendly to the environment; and the raw material, namely the 4,4'-dimethyl biphenyl adopted in the method provided by the invention is a byproduct of a medical intermediate, namely sartan biphenyl, and theproduction amount of the byproduct accounts for about 10% of the production amount of the sartan biphenyl, so the waste can be turned into treasure after the byproduct is applied to synthesis of the3,3',4,4'-biphenyltetracarboxylic acid.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3,3',4,4'-biphenyltetracarboxylic acid. Background technique [0002] 3,3',4,4'-biphenyltetracarboxylic acid is dehydrated and converted into 3,3',4,4'-biphenyldianhydride, which can be polymerized with various diamines to obtain excellent heat resistance and water resistance Polyimide insulation material with good solution, mechanical and flexibility properties. The polyimide synthesized by biphenyl dianhydride and p-phenylenediamine has good temperature resistance, and its thermal decomposition temperature can reach above 600°C. It is one of the varieties with high thermal stability among polymers so far. , can basically maintain the original physical properties in a short period of time. The material can be used for a long time below 333°C, and it will not be brittle at -269°C. The biphenyl dianhydride polyimide has high mechanica...

Claims

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Application Information

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IPC IPC(8): C07C51/245C07C51/265C07C63/331C07C51/083C07C59/84
CPCC07C51/245C07C51/265C07C51/083C07C59/84C07C63/331
Inventor 胡国宜胡锦平刘伟军
Owner CHANGZHOU SUNLIGHT PHARMA
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