Method for preparing triarylmethane compounds and application thereof

A triaryl methane and aryl methane technology, which is applied in the preparation and application of triaryl methane compounds, can solve the problems of difficult processing, production process constraints, and high cost of raw materials, and achieve the effect of good atom economy and low cost

Pending Publication Date: 2019-11-01
维思普新材料(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A typical method is to react aromatic aldehydes with N-substituted anilines under acidic conditions, and then use oxidation methods to obtain triarylmethane dyes under catalytic conditions. Some heavy metals such as lead, chromium, and manganese are used as oxidants during the oxidation process. ; The preparation of raw material aromatic aldehyde used in this type of method often pollutes heavier, so the preparation process of whole product is restricted
Another type of method is to use arylamine compounds and Michler's ketones as raw materials, first react Michler's ketone with phosphorus oxychloride, then add arylamine, continue the reaction, and obtain the product; this method uses toxicity and danger. Phosphorus oxychloride raw material with relatively high toxicity, and phosphorus-containing pollutants are produced at the same time, which is difficult to deal with, and the raw material Michler's ketone used at the same time is relatively expensive
Generally speaking, the existing methods have relatively heavy pollution during the preparation process, or the cost of raw materials is relatively high, which is not suitable for the existing green and environmental protection manufacturing policies

Method used

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  • Method for preparing triarylmethane compounds and application thereof
  • Method for preparing triarylmethane compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In a 250mL reaction flask equipped with a thermometer, a reflux condenser, and magnetic stirring, 26.66g (0.11mol) of N,N'-dimethylaniline, 50.87g (0.1mol) of 4,4'-bis(N, N'-Dimethyl)-diphenylmethane (methane bass), absolute ethanol 100mL, Salprn cobalt complex 1.0g, chloranil 1.5g, 5mL concentrated hydrochloric acid, heated to 65°C under stirring, passed into Oxygen, the flow rate is 15mL / min, react for 5 hours, analyze by HPLC sampling, methane bass reaction conversion is complete, stop the reaction, distill off ethanol, add 50mL water, and 10mL concentrated hydrochloric acid, heat to 75°C, filter, and cool the filtrate to Crystallize at room temperature, filter to obtain crystals with metallic luster, weigh after drying, 78.1 g, yield 95.7%. The characterization results are as follows:

[0030] Found: C, 73.70; H, 7.41; N, 10.39, Calc.for C 25 h 30 N 3 Cl: C, 73.62; H, 7.36; N, 10.31%. 1 H NMR (300MHz; CDCl 3 ;ppm) δH: 3.28(18H,s,-CH 3 ), 6.86(6H,d,J=9Hz,Ar H)...

Embodiment 2

[0032] In a 250mL reaction flask equipped with a thermometer, a reflux condenser, and magnetic stirring, 26.66g (0.11mol) of N,N'-dimethylaniline, 50.87g (0.1mol) of 4,4'-bis(N, N'-Dimethyl)-diphenylmethane (methane bass), absolute ethanol 100mL, Salen iron complex 1.0g, chloranil 1.5g, 5mL concentrated hydrochloric acid, heated to 65°C under stirring, passed into Oxygen, the flow rate is 20mL / min, react for 4 hours, sample and analyze by HPLC, methane bass reaction conversion is complete, stop the reaction, distill off ethanol, add 50mL water, and 10mL concentrated hydrochloric acid, heat to 70°C, filter, and cool the filtrate to Crystallize at room temperature, filter to obtain crystals with metallic luster, weigh after drying, 75.48g, yield 92.5%. The characterization results are as follows:

[0033] EA Found: C,73.70; H,7.41; N,10.39.Calc.for C 25 h 30 N 3 Cl: C, 73.62; H, 7.36; N, 10.31%. 1 H NMR (300MHz; CDCl 3 ;ppm) δH: 3.28(18H,s,-CH 3 ), 6.86(6H,d,J=9Hz,Ar H),7...

Embodiment 3

[0035]In a 250mL reaction flask equipped with a thermometer, reflux condenser, and magnetic stirring, put 16.42g (0.11mol) of N,N'-ethylaniline, 31.05g (0.1mol) of 4,4'-bis(N,N '-diethyl)-diphenylmethane (ethane bass), chloroform 100mL, Salen cobalt complex 0.5g, chloranil 1.0g, 10mL acetic acid, heated to 65°C with stirring, and oxygen flow rate 18mL / min, reacted for 6 hours, analyzed by HPLC sampling, the ethane bass reaction conversion was complete, stopped the reaction, distilled chloroform and acetic acid, added 50mL water, and 10mL concentrated hydrochloric acid, heated to 80 ° C, filtered, and the filtrate was cooled to Crystallize at room temperature, filter to obtain crystals with metallic luster, weigh after drying, 44.93g, yield 91.3%. The characterization results are as follows:

[0036] EA Found: C,75.57; H,8.72; N,8.61.Calc.for C 31 h 42 N 3 Cl: C, 75.66; H, 8.60; N, 8.54%; m / z (EI): 456.6 (M + -Cl - +1).

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Abstract

The invention discloses a method for preparing a triarylmethane dye. 4,4'-N,N-disubstituted aminodiphenylmethane (bass) and aromatic amines or substituted aromatic amines, phenols or substituted phenols are dissolved in a solvent, metal complexes and tetrachlorobenzoquinone are used as catalysts and oxygen is used as oxidant, the mixture reacts for 5-8 hours at acid conditions and a certain temperature, so that the product triarylmethane dye is obtained in one step, and the commercialized product is obtained through further treatment, so as to meet the application requirement in different fields. The method is simple and safe, and has high yield and less three-wastes.

Description

technical field [0001] This application relates to the field of organic synthesis, in particular to the preparation and application of a triaryl methane compound. Background technique [0002] Triarylmethane dyes are characterized by very vivid and high color rendering properties, and are used as purple, blue or green color materials in various paints, water-based inks, oil-based inks, inkjet inks, color filter inks, It is also used for color development in the process of preparing printed circuit boards and semiconductors, and is also used for staining of cell DNA in the biological field. Malachite green, the most famous of the triaryl methane dyes, was invented as early as 1877 and has been used for more than one hundred years. A typical method is to react aromatic aldehydes with N-substituted anilines under acidic conditions, and then use oxidation methods to obtain triarylmethane dyes under catalytic conditions. Some heavy metals such as lead, chromium, and manganese ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B11/14
CPCC09B11/22C09B11/14
Inventor 陈潇袁晓冬刘海丰陈华
Owner 维思普新材料(苏州)有限公司
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