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Production method of 2,2'-dimethyl[1,1'-biphenyl]-4,4'-diamine

A technology of dimethyldiphenylhydrazine and diamino, which is applied in the field of preparation of 4,4'-diamino-2,2'-dimethyl-1,1'-biphenyl, which can solve the problems and effects Ideal and other issues

Active Publication Date: 2019-12-20
CHANGZHOU SUNLIGHT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This new catalyst improves how we react with certain chemicals like nitrobenzol or napthoic acid without losing any effectiveness over time due to their ability to combine two different types of molecules together effectively.

Problems solved by technology

This patented technical problem addressed in this patents relates to improving the efficiency or quality of producing certain chemical substances called polysilicon dioxanes due to their unique properties like excellent thermal stability, solubility, flexibility, lightweight, durability, transmittance, opaqueness, etc.. These new types of molecules have potential applications in various industries where they can be applied alone or mixed together depending upon desired characteristics.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0028] The preparation method of 4,4'-diamino-2,2'-dimethyl-1,1'-biphenyl in this example is as follows:

[0029] ①Add 68.6g m-nitrotoluene (0.5mol) and 500mL toluene to the autoclave, then add 20mL sodium hydroxide aqueous solution (20wt%), 2g Pt / C catalyst (5wt%), 0.2g 1, 4-dihydroxyanthraquinone and 0.4 g of sodium dioctyl sulfosuccinate.

[0030] First replace the air in the kettle with nitrogen three times, fill it with hydrogen to a pressure of 0.9±0.1MPa after dyeing, first raise the temperature to 65±1°C for 5 hours, and then raise the temperature to 75±1°C for 3 hours.

[0031] After the reaction, the temperature was lowered to 50-55°C, filtered, the catalyst was recovered and used mechanically, and the filtrate was separated into layers.

[0032] ②Cool the organic layer obtained in step ① to 0-5°C, add 128g of 55wt% dilute sulfuric acid dropwise, and keep the reaction at 4-8°C for 12h after dropping.

[0033] After the reaction is over, separate the organic layer, ...

Embodiment 2～ Embodiment 6）

[0035] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0036] Table 1

[0037] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Anthraquinone cocatalyst 1,4-Dihydroxyanthraquinone 2,6-Dihydroxyanthraquinone 2-Hydroxyanthraquinone 1,4-Dihydroxyanthraquinone 1,4-Dihydroxyanthraquinone 1,4-Dihydroxyanthraquinone Aromatic hydrocarbon organic solvent toluene toluene toluene Xylene toluene toluene dilute sulfuric acid 128g, 55wt% 128g, 55wt% 128g, 55wt% 128g, 55wt% 110g, 65wt% 150g, 45wt% product weight 41.7g 40.0g 39.0g 40.9g 41.2g 41.4g yield 78.5% 75.3% 73.5% 77.0% 77.6g 78.0% purity 99.7% 98.9% 99.1% 99.6% 99.5% 99.6%

Embodiment 7）

[0039] The preparation method of 4,4'-diamino-2,2'-dimethyl-1,1'-biphenyl in this example is as follows:

[0040] ①Add 205.8g m-nitrotoluene (1.5mol) and 1.5L xylene into the autoclave, then add 60mL sodium hydroxide aqueous solution (20wt%), 6g Pt / C catalyst (5wt%), 0.6 g of 1,4-dihydroxyanthraquinone and 1.2 g of sodium dioctylsulfosuccinate.

[0041] First replace the air in the kettle with nitrogen three times, then fill it with hydrogen to a pressure of 0.9±0.1MPa, first raise the temperature to 65±1°C for 5 hours, and then raise the temperature to 75±1°C for 3 hours.

[0042] After the reaction, the temperature was lowered to 50-55°C, filtered, the catalyst was recovered and used mechanically, and the filtrate was separated into layers.

[0043] ②Cool the organic layer obtained in step ① to 0-5°C, add 360g of 60wt% dilute sulfuric acid dropwise, and keep the reaction at 4-8°C for 12h after dropping.

[0044] After the reaction is over, separate the organic layer, add 3...

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PUM

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Abstract

The invention discloses a production method of 2,2'-dimethyl[1,1'-biphenyl]-4,4'-diamine. According to the production method of the 2,2'-dimethyl[1,1'-biphenyl]-4,4'-diamine, with 3-nitrotoluene as aninitial raw material, reduction is conducted at first to obtain 3,3'-dimethylhydrazo-benzene, and then rearrangement is conducted to obtain the 2,2'-dimethyl[1,1'-biphenyl]-4,4'-diamine; reduction isconducted with Pd/C as a main catalyst and an anthraquinone compound plus sodium di(2-ethyl-hexyl)sulfosuccinate as cocatalysts; and the anthraquinone compound is one or two of 1,4-dihydroxyanthraquinone, 2-hydroxyanthraquinone and 2,6-dihydroxyanthraquinone. According to the production method of the 2,2'-dimethyl[1,1'-biphenyl]-4,4'-diamine, through a large number of experiments, it is found that by combining the sodium di(2-ethyl-hexyl)sulfosuccinate and the anthraquinone compound as the cocatalysts, the reaction selectivity of production of the 3,3'-dimethylhydrazo-benzene through reduction of the 3-nitrotoluene can be greatly improved, and the reaction yield which is 70% or above can be obtained finally, so that conditions are created for mass application of the 2,2'-dimethyl[1,1'-biphenyl]-4,4'-diamine on the aspect of production of special materials.

Description

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Claims

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Application Information

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Owner CHANGZHOU SUNLIGHT PHARMA
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