2,2'-Bis(trifluoromethyl)benzidine

Adding to the reactor 380g2, 2 '-bis-trifluoromethyl -4, the 4 [...] -dinitro biphenyl and 1600 ml methanol, after stirring to dissolve by adding 504g anhydrous ammonium formate and 13.1 g zinc powder (molar ratio of:2, 2 the [...] -bis-trifluoromethyl -4, 4 the [...] -dinitro biphenyl: anhydrous ammonium formiate : zinc powder: methanol =1:8: 0.2 : 40), the temperature rise under stirring 50 °C, to be the raw material after the reaction is complete, hot filtering, the filter cake is washed with methanol washing, solvent recovery filtrate under reduced pressure, the temperature after the crystal separation of filtering, drying to obtain 2, 2 the [...] -bis-trifluoromethyl -4, the 4-diaminobiphenyl [...] 310g, kind of white solid, yield 96.83percent.4.19 g of the light yellow liquid obtained by the reduction was dissolved in 14.0 g of toluene, and the solution was dropped into 15.0 g of 50percent sulfuric acid aqueous solution. The rearrangement reaction was conducted for 5 hours after the dropping. After the reaction has finished, reaction mixture was neutralized and extracted with toluene to obtain 41.4 g of toluene layer. As a result of analysis of the toluene layer, the concentration of 2, 2'-bis (trifluoromethyl)-4, 4'-diaminobiphenyl was 3.11percent, and the yield thereof was 31.8percent based on 3, 3'-bis(trifluoromethyl) hydrazobenzene in the light yellow liquid obtained by the reduction. The toluene solution separated above was concentrated for crystallization. A crystallized product was recrystallized to obtain a white crystal. The result of analysis of the crystal showed that it was 2, 2'-bis(trifluoromethyl)-4, 4'-diaminobiphenyl having purity of 99.9percent and melting point of 183° C. 2, 2'-bis(trifluoromethyl)-4, 4'-diaminobiphenyl was recovered by yield of 95.1percent from rearrangement reaction liquid; 5.00 g of the light brown liquid obtained by the above reduction was dissolved in 16.7 g of toluene and solution was dropped into 15.36 g of 50percent sulfuric acid aqueous solution. After the dropping the rearrangement reaction was conducted for 5 hours. After the reaction has finished, reaction mixture was stayed for separating liquid layers and then 17.7 g of aqueous layer of under part was separated. The result of analysis of the aqueous layer showed that the concentration of 2, 2'-bis(trifluoromethyl)-4, 4'-diaminobiphenyl was 8.35percent and its yield was 31.8percent based on 3, 3'-bis (trifluoromethyl)-4, 4'-hydrazobenzene in the light brown liquid obtained by the reduction.After the separated aqueous layer was neutralized, the aqueous layer was extracted by toluene. Extract was concentrated for crystallizing and then obtained solid body was recrystallized to obtain a white crystal. The result of analysis of the crystal showed that the crystal was 2, 2'-bis (trifluoromethyl)-4, 4'-diaminobiphenyl having purity 99.9percent and melting point of 183° C. The product was recovered by the yield of 95.2percent.8.71 g of the light brown liquid obtained by the reduction in was dissolved in 29.0 g of toluene. The solution was dropped into 22.1 g of concentrated hydrochloric acid while the temperature was kept at 25° C. After the dropping, the rearrangement reaction was conducted for 3 hours at 25° C. After the reaction has finished, reaction mixture was neutralized and extracted with toluene to obtain 86.1 g of toluene layer. The result of analysis of the toluene layer showed that the concentration of 2, 2'-bis(trifluoromethyl)-4, 4'-diaminobiphenyl was 2.48percent, and its yield was 25.4percent based on 3, 3'-bis(trifluoromethyl) hydrazobenzene the light brown liquid obtained by the reduction.The toluene layer was concentrated for crystallizing and obtained solid body was recrystallized to obtain a white crystal. The result of analysis of the crystal showed that it was 2, 2'-bis(trifluoromethyl)-4, 4'-diaminobiphenyl having purity of 99.9percent and melting point of 183° C. The product was recovered from the rearrangement reaction liquid by the yield of 95.0percent.4.50 g of the light brown liquid obtained by the reduction same as in was dissolved in 26.0 g of ethanol to obtain a solution. 13.6 g of 50percent sulfuric acid aqueous solution was dropped into the solution. After the dropping, the rearrangement reaction was conducted for 12 hours. 43.6 g of reaction liquid was recovered and analyzed. The result of analysis showed that the concentration of 2, 2'-bis(trifluoromethyl)-4, 4'-diaminobiphenyl was 0.95percent and its yield was 9.5percent based on 3, 3'-bis(trifluoromethyl) hydrazobenzene in the light brown liquid obtained by the reduction.4.50 g of the light brown liquid obtained by the reduction same as in was dissolved in 37.5 g of ethanol to obtain a solution. 5.53 g of concentrated hydrochloric acid was dropped into the solution at 0° C. After the dropping, rearrangement reaction was conducted for 24 hours. 50.7 g of reaction liquid was recovered and analyzed. The result of analysis showed that the concentration of 2, 2'-bis(trifluoromethyl)-4, 4'-diaminobiphenyl was 0.21percent and its yield was 2.4percent based on 3, 3'-bis(trifluoromethyl) hydrazobenzene in the light brown liquid obtained by the reduction.

2,2-bis(trifluoromethyl)-4,4-diaminobiphenyl be used for producing a high strength flexible transparent polyimide material.

Molecular Weight:320.23
XLogP3:4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:1
Exact Mass:320.07481730
Monoisotopic Mass:320.07481730
Topological Polar Surface Area:52
Heavy Atom Count:22
Complexity:345
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes