Method for preparing 4,4'-diamino-4'-hydroxytriphenylmethane

A technology of hydroxytriphenylmethane and p-hydroxybenzaldehyde, which is applied in 4 fields, can solve the problems of low yield, decreased yield, and many operation steps, and achieve the effect of less equipment investment, low cost, and simple operation

Inactive Publication Date: 2008-03-05
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0025] The shortcoming of this preparation method is: (1) yield is on the low side; (2) use low boiling point flammable ether organic solvent in the preparation process, be unfavorable for safe production; (3) use hydrochloric acid, sodium hydroxide solution in the preparation process , in this regard, must strictly control the dosage, otherwise the yield of the target product will be greatly affected, resulting in a serious decline in the yield, which is unfavorable for the process control of production; (4) separation and purification with column chromatography cannot be used for industrialized batch production, Therefore, it is very difficult for this method to realize industrialized production; (5) the melting point of the product is low, and further purification is needed; (6) there are many operating steps, which virtually increases the production cost

Method used

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  • Method for preparing 4,4'-diamino-4'-hydroxytriphenylmethane

Examples

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Embodiment 1

[0044] Add 18.6 grams (0.1 moles) of newly distilled aniline into the reaction kettle, stir at room temperature, add 19.8 grams (0.2 moles) of 37% hydrochloric acid aqueous solution dropwise, react at room temperature for 0.1 hour, add 10 milliliters of toluene, stir, and heat up Reflux to separate the water until no more water comes out, cool naturally, and precipitate a white solid product, filter, and dry in vacuum to obtain 20.7 g of white aniline hydrochloride crystals with a melting point of 196.3°C to 198.0°C and a purity of 99.1%. The obtained crystal weight of aniline hydrochloride and the theoretical yield (25.9 g) calculated that the yield of aniline hydrochloride was 80%.

Embodiment 2

[0046] Add 18.6 grams (0.1 moles) of newly distilled aniline to the reactor, stir at room temperature, add dropwise 29.8 grams (0.3 moles) of 37% hydrochloric acid aqueous solution, and react at room temperature for 4 hours, add 400 milliliters of xylene, stir, and heat Heat up and reflux to separate water until no more water comes out, cool naturally, and a white solid product is precipitated, filtered, and vacuum-dried to obtain 23.3 g of white aniline hydrochloride crystals with a melting point of 197.5°C to 198.3°C and a purity of 99.8%. According to According to the actual obtained crystal weight of aniline hydrochloride and the theoretical yield (25.9 grams), the yield of aniline hydrochloride was calculated to be 90%.

Embodiment 3

[0048]Add 18.6 grams (0.1 mol) of newly distilled aniline to the reactor, stir at room temperature, add dropwise 24.6 grams (0.25 mol) of 37% aqueous hydrochloric acid solution, and react at room temperature for 1 hour, add 100 ml of dichlorobenzene, and stir , heat up and reflux to separate water until no more water comes out, cool naturally, and a white solid product is precipitated, filtered, and vacuum-dried to obtain 24.4 g of white aniline hydrochloride crystals with a melting point of 197.2°C to 198.1°C and a purity of 99.8% According to the crystal weight of aniline hydrochloride actually obtained and the theoretical yield (25.9 grams), the yield of aniline hydrochloride was calculated to be 94%.

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Abstract

The present invention relates to process of preparing 4, 4'-diamido-4''-hydroxy triphenyl methane. The process includes the following steps: 1. reaction of aniline and hydrochloric acid solution in the molar ratio of 1.0 to 1.0-1.5 at room temperature for 0.1-4 hr, adding water insoluble organic solvent, heating reflux to separate out water, cooling, filtering and drying to obtain aniline hydrochloride; and 2. reaction of p-hydroxybenzaldehyde and aniline in the molar ratio of 1.0 to 2.0-4.0 in nitrogen with aniline hydrochloride as catalyst at 80-120 for 1-8 hr, cooling, vacuumizing, eliminating excessive aniline, adding alcohol solvent, heating to dissolve, cooling to crystallize, filtering and drying to obtain purple needle-shaped 4, 4'-diamido-4''-hydroxy triphenyl methane crystal. The present invention has simple operation, low cost and high product purity, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of preparation of organic compounds, in particular to a preparation method of 4,4'-diamino-4"-hydroxytriphenylmethane. Background technique [0002] Polyimide is widely used in high-performance fields such as electronic microelectronics and aerospace due to its excellent heat resistance, solvent resistance, nuclear radiation resistance, flame retardancy, and good mechanical and electrical properties. Aromatic dibasic primary amines are one of the important raw materials for the synthesis of polyimides. [0003] U.S. Dupont Company uses 4,4'-diaminodiphenyl ether to prepare Kapton polyimide film and Vespel polyimide engineering plastics series products. [0004] US GE Company uses 1,3-diaminobenzene to prepare Ultem polyimide resin series products. [0005] Japan Ube Company uses 1,4-diaminobenzene to prepare Upilex-S polyimide film series products. [0006] Amoco Corporation of the United States uses 4,4'-diaminodi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/74C07C213/00
Inventor 虞鑫海徐永芬赵炯心
Owner DONGHUA UNIV
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