A kind of preparation method of permanent violet pigment

A permanent violet and pigment technology, applied in the direction of bisazine oxazine dyes, etc., can solve the problems of low selectivity of ring-closing reaction, a large amount of by-product hydrochloric acid, a large amount of waste residue, etc., to improve selectivity and total yield, and reduce by-products The generation, the effect of reducing environmental pollution

Inactive Publication Date: 2016-04-27
NANTONG HAIDI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using aromatic ring acid chloride as a ring-closing agent will produce a large amount of by-product hydrochloric acid during the reaction, which will seriously corrode equipment and pollute the environment
In addition, the use of active aromatic ring acid chlorides results in low selectivity of the ring-closing reaction and the formation of thioether by-products (US20020091257A1), which are difficult to remove, resulting in low ring-closing yields and a large amount of waste residue
Patent EP234870 discloses the use of inorganic acids (such as hydrochloric acid, sulfuric acid) as a ring-closing agent, 2,5-dichloro-3,6-bis(9-ethyl-3-carbazole amino)-1,4-benzoquinone in React in o-dichlorobenzene at 155-160°C to obtain crude permanent violet pigment, but the reaction conversion rate is low, and the use of inorganic acid still brings equipment corrosion problems
U.S. Patent US5932727A discloses that pyridine nitrogen oxide is used as a ring-closing agent, and the ring-closing yield can reach up to 97%, but the price of the ring-closing agent is high and recovery is difficult
In addition, the use of the highly toxic substance pyridine will seriously endanger the health of employees, so it is difficult to realize industrialization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Put 210g of 3-amino-N-ethylcarbazole and 2000ml of o-dichlorobenzene into a 5000ml reactor, stir to dissolve and heat up to 35°C, add 140.7g of tetrachlorobenzoquinone, then dropwise add 105g of triethylamine, and then Keep warm for 3 hours to obtain a solution containing 2,5-dichloro-3,6-bis(9-ethyl-3-carbazolylamino)-1,4-benzoquinone, add 1g of copper sulfate and 2g of anthraquinone, close the reactor, feed oxygen, control the pressure at 0.2MPa, raise the temperature to 165°C, keep the temperature at this temperature for 4 hours, after the reaction is over, cool to 100°C and discharge, filter, and use o-dichlorobenzene, Wash with methanol and water, and dry to obtain 279.5 g of crude permanent violet pigment, with a yield of 94.9% and a content of 98.5%.

Embodiment 2

[0024] Put 210g of 3-amino-N-ethylcarbazole and 2000ml of o-dichlorobenzene into a 5000ml reactor, stir to dissolve and heat up to 36°C, add 140.7g of tetrachlorobenzoquinone, then dropwise add 105g of triethylamine, and then Keep warm for 3 hours to obtain a solution containing 2,5-dichloro-3,6-bis(9-ethyl-3-carbazolylamino)-1,4-benzoquinone, heat up to 150°C under stirring, add 140g of benzenesulfonyl chloride, continue to heat up to 178 ° C, keep warm at this temperature for 4 hours, the reaction is completed, cool to 130 ° C, discharge, filter, wash with o-dichlorobenzene, methanol and water in sequence, and dry to obtain 249.2 g of permanent solid Crude purple pigment, the yield is 84.6%, and the content is 98.6%.

Embodiment 3

[0026] Put 210g of 3-amino-N-ethylcarbazole and 2000ml of o-dichlorobenzene into a 5000ml reactor, stir to dissolve and heat up to 37°C, add 140.7g of tetrachlorobenzoquinone, then dropwise add 105g of triethylamine, and then Keep it warm for 3 hours to obtain a solution containing 2,5-dichloro-3,6-bis(9-ethyl-3-carbazolylamino)-1,4-benzoquinone, add 3g of copper sulfate to the reactant, Close the reaction kettle, feed oxygen, control the pressure at 0.2MPa, raise the temperature to 165°C, maintain this temperature for 4 hours, and cool to 100°C to discharge the material, filter, and wash with o-dichlorobenzene, methanol and water in sequence , drying to obtain 263.6g crude permanent violet pigment, the yield was 89.5%, and the content was 97.8%.

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Abstract

The invention discloses a preparation method of a permanent violet pigment. The method comprises the following steps: dissolving 3-amino-N-ethyl carbazole in an organic solvent and carrying out a condensation reaction by adding chloranil in the presence of an acid-binding agent so as to obtain an organic solution containing 2,5-dichloro-3,6-di(9-ethyl-3-carbazole amino)-1,4-benzoquinone after the reaction; adding a metal salt catalyst into the organic solution obtained in the step a or simultaneously adding the metal salt catalyst and a quinone compound cocatalyst into the organic solution; feeding air or oxygen into a reaction kettle to reach a certain pressure; carrying out heat preservation at 120-180 DEG C for 2-10 hours; cooling to 80-120 DEG C after the reaction; washing a filter cake obtained after filtering with a small amount of organic solvent; then, respectively washing with methyl alcohol and water and drying, thereby obtaining a crude permanent violet pigment product. According to the method, a traditional poisonous and harmful closed-loop agent is not adopted, so that the cost of raw materials is saved; the generation of byproducts is reduced, so that the selectivity and total yield of the reaction are improved. Thus, less environmental pollution is generated.

Description

technical field [0001] The invention relates to a method for preparing a pigment, in particular to a method for preparing a permanent violet pigment. Background technique [0002] Permanent violet pigment is a high-grade machine pigment with dioxazine structure. As a high-grade purple organic pigment, it has outstanding coloring strength, brightness, excellent heat resistance, permeability resistance and good light fastness, and is widely used in coatings, plastics, inks, textile printing and other fields. Permanent violet pigment, see the following structure: [0003] The preparation of permanent violet pigment is based on carbazole as raw material, and the product of the above structure is obtained through the process steps of alkylation, nitration, reduction, condensation, and ring closure. At present, this method is almost used in industrial production at home and abroad (Xie Qiusheng. Yong Synthesis of Fast Violet RL and its intermediates, "Dyes and Dyeing", 2003, Vol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B19/02
Inventor 张耀叔黄豪杰侯启军顾耀倪海平
Owner NANTONG HAIDI CHEM
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