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Preparation method of 4, 4 ', 5, 5'-tetramethyl [1, 1 '-biphenyl]-2, 2'-diamine

A technology of dimethylaniline and tetramethyl, applied in the field of compound synthesis, can solve problems such as high cost of catalyst, and achieve the effects of long service life, high yield and small loss of catalyst

Pending Publication Date: 2022-06-07
绍兴贝斯美化工股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The literature on pages 4812-4823 of Volume 83, No. 8, pp. 4812-4823 of Journal of Organic Chemistry discloses that under room temperature conditions, to catalyze Pd(OAc) 2 and K 2 S 2 o 8 As an oxidizing agent, in MsOH / CF 3 In COOH(TFA), the secondary 2,2'-diphenylamine was successfully prepared through the oxidative coupling of the aryl ortho-sp2 C-H bond of aniline, which provides a new method for the synthesis of biphenyl, but the catalyst cost is relatively expensive

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  • Preparation method of 4, 4 ', 5, 5'-tetramethyl [1, 1 '-biphenyl]-2, 2'-diamine

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Experimental program
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Embodiment 1

[0049] (1) Amino protection: with 750ml of dichloroethane as solvent, 150g of raw materials 3,4-dimethylaniline (purity 99%), 189g of triethylamine, 189g of acetic anhydride were added, the oil bath was heated to reflux, refluxed for 5h, The solvent was distilled off, the residue was extracted with chloroform, washed with saturated sodium bicarbonate and saturated brine solution, and the oil layer was taken and concentrated to obtain 197.0 g of N-(3,4-dimethylphenyl)acetamide (purity 98.5%), The yield was 97%.

[0050] (2) Nitration substitution: Using 1000 ml of acetic acid as a solvent, 196.5 g of N-(3,4-dimethylphenyl)acetamide (purity 98.5%) was put into acetic acid. The mixed solution was cooled to 0-5°C, 82.9 g of nitric acid and 108.3 g of sulfuric acid (purity 98%) were added dropwise, and the reaction was incubated for 0.5 h after the dropwise addition, and then the temperature was continued to rise to room temperature for 1 h, and the reaction solution was poured int...

Embodiment 2

[0059] (1) Amino protection: with 1500ml dichloroethane as solvent, add 300g raw material 3,4-dimethylaniline (purity 99%), 378g triethylamine, 378g acetic anhydride, the oil bath is heated to reflux, refluxed for 5h, The solvent was distilled off, the residue was extracted with chloroform, washed with saturated sodium bicarbonate and saturated brine solution, and the oil layer was taken and concentrated to obtain 378.0 g of N-(3,4-dimethylphenyl)acetamide (purity 98.5%), The yield was 97%.

[0060] (2) Nitration substitution: Using 1000 ml of acetic acid as a solvent, 393 g of N-(3,4-dimethylphenyl)acetamide (purity 98.5%) was put into acetic acid. The mixed solution was cooled to 0-5°C, 165.8g of nitric acid and 216.6g of sulfuric acid (purity 98%) were added dropwise, after the dropwise addition was completed, the reaction was incubated for 0.5h, and then the temperature was continued to rise to room temperature for 1h, and the reaction solution was poured into water, Stir...

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Abstract

The invention discloses a preparation method of 4, 4 ', 5, 5'-tetramethyl [1, 1 '-biphenyl]-2, 2'-diamine, which comprises the following steps: carrying out amino protection, nitration substitution, deprotection, diazotization iodination, catalytic coupling, iron powder catalytic reduction, extraction and concentration on a raw material 3, 4-dimethylaniline to obtain the 4, 4 ', 5, 5'-tetramethyl [1, 1 '-biphenyl]-2, 2'-diamine. According to the present invention, with the method, the high 4, 4 ', 5, 5'-tetramethyl [1, 1 '-biphenyl]-2, 2'-diamine yield can be obtained, and the price of the used catalyst is low.

Description

technical field [0001] The invention belongs to a method for synthesizing a compound, in particular to a method for preparing 4,4',5,5'-tetramethyl[1,1'-biphenyl]-2,2'-diamine. Background technique [0002] 4,4′,5,5′-Tetramethyl[1,1′-biphenyl]-2,2′-diamine is light yellow powder, which is an excellent cross-linking agent for synthesis of dibenzofuran tetracarboxylic dianhydride key intermediates. Dianhydrides are excellent crosslinking agents, especially for crosslinking polyols, ultimately forming polyester crosslinks in polymer systems. Because it is highly aromatic, its cross-linked polymer has good thermal properties. Therefore, in many cases, especially when it is desired to have a sufficiently high thermal stability of the cross-linking element, such cross-linking agents are often used to increase the integrity of the polymer system. [0003] In the existing literature, research on 4,4′,5,5′-tetramethyl[1,1′-biphenyl]-2,2′-diamine is very limited. [0004] Puskas, ...

Claims

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Application Information

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IPC IPC(8): C07C209/36C07C211/54C07C201/12C07C205/06C07C205/12C07C209/62C07C211/52C07C231/12C07C233/15C07C231/02C07C233/07
CPCC07C209/36C07C201/12C07C209/62C07C231/12C07C231/02C07C211/54C07C205/06C07C205/12C07C211/52C07C233/15C07C233/07Y02P20/55
Inventor 钟锡君田园陈湘朋杨巧芳耿敬坤
Owner 绍兴贝斯美化工股份有限公司