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Synthesis of N,N-di(4-methyl phenyl)-4-(2, 2-diphenylethyllene)aniline

A technology of diphenylethylene and methylphenyl, which is applied in the field of N, can solve the problems of being unsuitable for large-scale production, long reaction steps, and low product yield, and achieve products that are easy to purify, have fewer reaction steps, and have high purity Effect

Active Publication Date: 2009-05-13
BEIJING ODYSSEY CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method has long reaction steps, low product yield and high cost, and is not suitable for large-scale production

Method used

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  • Synthesis of N,N-di(4-methyl phenyl)-4-(2, 2-diphenylethyllene)aniline
  • Synthesis of N,N-di(4-methyl phenyl)-4-(2, 2-diphenylethyllene)aniline

Examples

Experimental program
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Effect test

Embodiment 1

[0038] 1. Synthesis of diethyl diphenylmethylphosphonate:

[0039]Heat hydrobromic acid with a mass percent concentration of 48% to 95°C, add diphenylmethanol, react at 95°C for 2 hours, cool down to 60°C, add toluene, stand still, separate the organic phases, and wash the organic phases. Dry to obtain a toluene solution of diphenylbromomethane; add triethyl acetate to the toluene solution of diphenylbromethane, heat to 156°C for 2 hours, and distill under reduced pressure to obtain crude diethyl diphenylmethylphosphonate , recrystallized with petroleum ether 6 times the weight of the crude product; the molar ratio of hydrobromic acid, diphenylmethanol and triethyl phosphite added was 5.5:1:2. The added sherwood oil weight is 4 times of crude product weight. The high-performance liquid chromatography analysis content was 98.5%, and the yield was 72%.

[0040] 2. Synthesis of N, N-bis(4-methylphenyl)aniline:

[0041] With xylene as solvent, N,N-bis(4-methylphenyl)aniline is ...

Embodiment 2

[0050] 1. Synthesis of diethyl diphenylmethylphosphonate:

[0051] Heat hydrobromic acid with a mass percentage concentration of 48% to 90°C, add diphenylmethanol, react at 90°C for 2 hours, cool down to 40°C, add toluene, stand still, separate layers to take the organic phase, wash the organic phase, and dry , to obtain a toluene solution of diphenylbromomethane; add triethyl phosphite to the toluene solution of diphenylbromethane, heat to 120 ° C for 2 hours, and distill under reduced pressure to obtain diethyl diphenylmethylphosphonate crude product, Recrystallize with petroleum ether 6 times the weight of the crude product; the molar ratio of hydrobromic acid, diphenylmethanol and triethyl phosphite added is 6:1.2:2.5; the yield is 74%.

[0052] 2. Synthesis of N, N-bis(4-methylphenyl)aniline:

[0053] With xylene as solvent, N,N-bis(4-methylphenyl)aniline is produced by reacting aniline and p-iodotoluene under the catalysis of o-phenanthroline, ketone bromide and potassi...

Embodiment 3

[0061] 1. Synthesis of diethyl diphenylmethylphosphonate:

[0062] Heat hydrobromic acid with a mass percentage concentration of 48% to 93°C, add diphenylmethanol, react at 93°C for 1 hour, cool down to 50°C, add toluene, stand still, separate the layers to take the organic phase, wash the organic phase, and dry , to obtain a toluene solution of diphenylbromomethane; add triethyl phosphite to the toluene solution of diphenylbromethane, heat to 140 ° C for 1.5 hours, and distill under reduced pressure to obtain diethyl diphenylmethylphosphonate crude product, Recrystallize with petroleum ether 6 times the weight of the crude product; the molar ratio of hydrobromic acid, diphenylmethanol and triethyl phosphite added is 5.8:1:2; the yield is 73.5%.

[0063] 2. Synthesis of N, N-bis(4-methylphenyl)aniline:

[0064] With xylene as solvent, N,N-bis(4-methylphenyl)aniline is produced by reacting aniline and p-iodotoluene under the catalysis of o-phenanthroline, ketone bromide and po...

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Abstract

The invention relates to a method for synthesizing N, N-bis(4-methylphenyl)-4-(2, 2-diphenylvinyl). The method comprises the following steps: diphenylbromomethane and triethyl phosphite react to form diphenylmethyl phosphonic diethylester; N, N-(4-methylphenyl)aniline is synthesized by use of aniline and p-Iodotoluene in the presence of cuprous bromide and other catalysts; N, N-bis(4-methylphenyl)-4-aminobenzaldehyde is formed by use of phosphorus oxychloride and N, N-dimethylformamide formacyl; and the diphenylmethyl phosphonic diethylester reacts with the N, N-bis(4-methylphenyl)-4-aminobenzaldehyde to form the N, N-bis(4-methylphenyl)-4-(2, 2-diphenylvinyl). The method has the advantages that the method is simple in steps, easy to control reaction conditions, low in requirements on equipment, high in yield and applicable to industrial production.

Description

technical field [0001] The present invention relates to a kind of synthesis method of N,N-bis(4-methylphenyl)-4-(2,2-diphenylethenyl)aniline, in particular to a method for synthesizing N,N-bis (4-methylphenyl) aniline, and then generate N,N-bis(4-methylphenyl)-4-aminobenzaldehyde, and finally synthesize N,N-(4-methylphenyl)-4- (2,2-Diphenylvinyl)aniline method. Background technique [0002] Charge transport materials are the key materials for organic photoelectric drums (OPC), organic electroluminescent displays (OLED), organic solar cells (OPE) and other devices. Triphenylamine compounds are a class of charge-transporting materials with excellent properties, among which N,N-bis(4-methylphenyl)-4-(2,2-diphenylvinyl)aniline has high performance due to its large conjugation degree. Even better, the double-layer photoconductor prepared by compounding the charge transport material with the azo compound as the charge generation material has high charge retention ability, low da...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54C07C209/68
Inventor 吴细兵刘斌
Owner BEIJING ODYSSEY CHEM
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