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Synthesis method of dye intermediate

The technology of a dye intermediate and a synthesis method is applied in the field of preparation of the dye intermediate, and can solve the problems of easy decomposition of methyl chloroacetate recovery, large proportion of methyl chloroacetate, difficulty in recovery and reuse, and the like, so as to eliminate the need for distillation and recovery. Process, production environment improvement, avoid the effect of storage perishable

Inactive Publication Date: 2012-08-15
HANGZHOU JIHUA JIANGDONG CHEMICAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] For the solution currently containing -CH 2 COOCH 3 In the preparation process of the substituted aniline dye intermediates, the required methyl chloroacetate ratio in the N-alkylation reaction of methyl chloroacetate is large, the recovery and reuse are difficult, and the storage is easy to deteriorate. The present invention proposes a dye intermediate The synthetic method of body, adopting the inventive method can greatly reduce the consumption of methyl chloroacetate, saves distillation recovery methyl chloroacetate operation, has avoided the problem that methyl chloroacetate reclaims easy decomposition

Method used

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  • Synthesis method of dye intermediate
  • Synthesis method of dye intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 162.8 g (1.50 mol) of methyl chloroacetate and 100.0 g of toluene into the flask, add 75.0 g (0.50 mol) of m-aminoacetanilide, 66.5 g of sodium carbonate, and 7.7 g of sodium bromide while stirring, and beat for 30 minutes. Slowly raise the temperature to 110~115°C, reflux and divide water, react for 6 hours to the end, and the main content is >96%. Cool to 40°C, add 450g of glacial acetic acid to obtain about 600g of esterification solution of dye intermediate with structural formula (I-1), and the yield is about 92.5% (calculated based on the coupling value). Collect the oil-water mixture separated by reflux, remove the water layer, and the oil layer will be used in the next batch.

[0032] (I-1)

[0033] Apply mechanically: add 135.6g (1.25mol) of methyl chloroacetate to the flask and separate the oil layer from the previous batch (less than 100g, add toluene to 100g), add m-aminoacetanilide 75.0g (0.50mol), sodium carbonate 66.5 g, sodium bromide 7.7g, beati...

Embodiment 2

[0037] Add 162.8g (1.50mol) of methyl chloroacetate and 100g of benzene into the flask, and add 90.0g (0.50mol) of 2-amino-4-acetamidoanisole, 105.4g of sodium bicarbonate and 3.3g of sodium bromide under stirring , beating for 30 minutes. Slowly raise the temperature to 110~115°C, reflux and divide water, react for 8 hours to the end, and the main content is >95%. Cool to 30°C, add 250g of glacial acetic acid to obtain about 420g of esterification solution of dye intermediate with structural formula (I-2), and the yield is about 90% (calculated based on the coupling value). Collect the oil-water mixture separated by reflux, remove the water layer, and the oil layer will be used in the next batch.

[0038] (I-2)

[0039]Apply mechanically: Add 135.6g (1.25mol) of methyl chloroacetate to the flask and separate the oil layer from the previous batch (less than 100g, add benzene to 100g), add 90.0g of 2-amino-4-acetamidoanisole ( 0.50mol), sodium bicarbonate 105.4g, sodium ...

Embodiment 3

[0042] Add 81.4 g (0.75 mol) of methyl chloroacetate and 120 g of n-propanol in the flask, and add 133.0 g (0.50 mol) of 3-(N-methoxyisopropionyl) amino-4-methoxyacetanilide, hydrogen Magnesium oxide 19.0g, sodium bromide 3.9g, beating for 30min. Slowly raise the temperature to 100~105°C, reflux and divide water, react for 8 hours to the end, and the main content is >94%. Cool to 40°C, add 270g of glacial acetic acid to obtain about 450g of esterification solution of dye intermediate with structural formula (I-3), and the yield is about 90% (calculated based on the coupling value). Collect the oil-water mixture separated by reflux, remove the water layer, and the oil layer will be used in the next batch.

[0043] (I-3)

[0044] Apply mechanically: Add 67.8g (0.625mol) of methyl chloroacetate to the flask and separate the oil layer from the previous batch (less than 120g, add n-propanol to 120g), add 3-(N-methoxyisopropionyl)amino under stirring - 133.0 g (0.50 mol) of 4-m...

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Abstract

The invention relates to the technical field of dye. In order to solve the problem that the methyl chloroacetate N-alkylation reaction in the existing preparation process of -CH2COOCH3-containing substituted aniline dye intermediate is large in required methyl chloroacetate proportion, hard to recycle, easy to deteriorate during storing and the like, the invention provides a synthesis method of dye intermediate, i.e. a synthesis method of dye intermediate shown in the general formula (I), comprising the following steps of: taking substituted aniline shown in the general formula (II) as a raw material, adding water aqua, methyl chloroacetate, catalyst sodium bromide and acid-binding agent, pulping and heating to reflow and divide water, and carrying out the N-alkylation reaction, so that the dye intermediate is prepared. After the method in the invention is adopted, the consumption of methyl chloroacetate can be greatly reduced, the methyl chloroacetate distillation recovery working procedure can be eliminated, and the problem that the recovered methyl chloroacetate is easy to decompose can be avoided.

Description

technical field [0001] The invention relates to the technical field of dyes, in particular to a preparation method of a dye intermediate. Background technique [0002] Contains -CH 2 COOCH 3 Substituted anilines are widely used as a class of important dye intermediates, and the commonly used preparation process is to use a large amount of methyl chloroacetate to carry out N-alkylation synthesis in the presence of an acid agent (such as soda ash). Methyl chloroacetate is not only used as a reaction solvent, but also as an alkylating agent and a water-carrying agent, and is used in a large amount. During double N-alkylation, the molar mass ratio of it to the raw material sometimes needs to reach more than 5:1. Methyl chloroacetate is relatively toxic and has a stimulating effect on all tissues of the human body. It is harmful to the body after inhalation, ingestion, and percutaneous absorption. Simultaneously, the use of a large amount of methyl chloroacetate will inevitabl...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/43
Inventor 孙岩峰简卫陈美芬冯国仁
Owner HANGZHOU JIHUA JIANGDONG CHEMICAL CO LTD
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