Preparation method of 4,4'-diamino-2,2'-dimethyl-1,1'-biphenyl

A technology of dimethyldiphenylhydrazine and diamino, which is applied in the field of preparation of 4,4'-diamino-2,2'-dimethyl-1,1'-biphenyl, can solve unsatisfactory effects, Can't wait for the problem

Active Publication Date: 2022-03-22
CHANGZHOU SUNLIGHT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the applicant has found through a lot of experiments that the effect of applying the catalytic hydrogenation system to m-nitrotoluene is not ideal, far inferior to that of o-nitrotoluene and m-nitrobenzotrifluoride

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] 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）

[0038] The preparation method of 4,4'-diamino-2,2'-dimethyl-1,1'-biphenyl in this example is as follows:

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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 preparation method of 4,4'-diamino-2,2'-dimethyl-1,1'-biphenyl, which uses m-nitrotoluene as a starting material, and first reduces to obtain 3 ,3'-dimethyldiphenylhydrazine, and then rearranged to obtain 4,4'-diamino-2,2'-dimethyl-1,1'-biphenyl; the reduction is based on Pd / C as the main catalyst, Anthraquinone compound + sodium dioctyl succinic acid sulfonate as a cocatalyst; the anthraquinone compound is one of 1,4-dihydroxyanthraquinone, 2-hydroxyanthraquinone, 2,6-dihydroxyanthraquinone or two kinds. After a large number of experiments, the present invention finds that the combination of sodium dioctyl succinic acid sulfonate and anthraquinone compound as a cocatalyst can greatly improve the reaction selectivity of m-nitrotoluene reduction to prepare 3,3'-dimethyldiphenylhydrazine, and finally The ability to obtain a reaction yield of more than 70% creates conditions for its extensive application in the preparation of special materials.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a preparation method of 4,4'-diamino-2,2'-dimethyl-1,1'-biphenyl. Background technique [0002] Polyimide is one of the organic polymer materials with the best comprehensive performance, and has been widely used in aviation, aerospace, microelectronics, nano, liquid crystal, separation membrane, laser and other fields. In the 1960s, all countries listed the research, development and utilization of polyimide as one of the most promising engineering plastics in the 21st century. [0003] 4,4'-diamino-2,2'-dimethyl-1,1'-biphenyl is an important high-performance material monomer, which is mainly used in the fields of microelectronics and optoelectronics to prepare extremely low dielectric constant , Very low surface free energy, high mechanical strength, high wear resistance, colorless and transparent polyimide material. [0004] At present, the existing methods ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C241/02C07C243/22C07C209/54C07C211/50B01J31/02B01J23/44
CPCC07C241/02C07C209/54B01J31/0225B01J31/0229B01J31/0205B01J23/44B01J2231/641C07C243/22C07C211/50
Inventor 胡国宜胡锦平吴建华张培锋
Owner CHANGZHOU SUNLIGHT PHARMA
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