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Alkylation preparation method for aniline intermediate

An intermediate and alkylation technology, applied in the field of alkylation preparation of aniline intermediates, can solve the problems of uneven product crystallization, unstable quality, low yield of alkylated products, etc. Cost-effective, the effect of preventing oil-water stratification

Inactive Publication Date: 2010-04-21
浙江龙盛染料化工有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The yield of the alkylation product obtained by the above method is generally not high, the crystallization of the product is uneven, and the quality is unstable

Method used

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  • Alkylation preparation method for aniline intermediate
  • Alkylation preparation method for aniline intermediate
  • Alkylation preparation method for aniline intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Take 108g of 3-amino-4-methoxyacetanilide (mole number 0.6) and make a slurry in 324g water, add 33g heavy magnesium oxide (mole number 0.83) as an acid-binding agent, then add 1.08g benzyl triethyl chloride Ammonium and 1.8g dispersant MF are used as catalysts, cooled to 5°C, then add 96.8g (1.5 moles) of ethyl chloride cooled to 5°C, seal, start the mixer, and heat to 90-100°C, keep warm for 18h, react After the end, cool to 80°C, and feed nitrogen into the material to drive off unreacted ethyl chloride, then add 90g of water, stir, filter, wash with water, and dry to obtain 2-methoxy-5-acetamido-N, N-diethylaniline, the yield of the obtained product is 96.6%, the purity is 99.2% (liquid chromatography), and the crystallization is uniform. The reaction formula is as follows:

[0024]

Embodiment 2

[0026] Take 110g of 3-amino-4-methoxyacetanilide (0.61 moles) and make a slurry in 255g water, add 29g of heavy magnesium oxide (0.73 moles) as an acid-binding agent, and then add 0.886g of benzyltriethyl chloride Ammonium and 1.15g dispersant (mixture of 0.8gMF and 0.35gNNO) as catalyst, cooled to 5°C, then added 92g (mole number 1.43) of ethyl chloride cooled to 5°C, sealed, started the mixer, and heated to 90~ 100°C, keep warm for 18h, after the reaction, cool to 80°C, and pass nitrogen into the material to drive off unreacted ethyl chloride, add 100g of water, stir, filter, wash with water, and dry to obtain 2-methoxy -5 Acetylamino-N, N-diethylaniline, the yield of the product obtained is 96.8%, and the purity is 99.5%.

Embodiment 3

[0028] Take 93.8g of 3-acetamidoaniline and beat in 280g of water, add 27.5g of heavy magnesium oxide as an acid-binding agent, then add 1.6g of benzyltriethylammonium chloride and 1.3g of lignin as a catalyst, cool to 5°C, Then add 101g of ethyl chloride cooled to 5°C, seal it, start the mixer, and heat to 90-100°C, keep it warm for 16h, after the reaction, cool to 80°C, and pass nitrogen into the material to drive off unreacted chlorine Add ethane, add 100 g of water, stir, filter, wash with water, and dry to obtain 3-acetamido-N,N-diethylaniline. The yield of the product is 97.2%, and the purity is 99.7%. The reaction formula is as follows:

[0029]

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Abstract

The invention provides an alkylation preparation method for aniline intermediate, which comprises the following steps: beating the aniline intermediate expressed by formula (1) in aqueous solution, adding an acid-catching agent, a catalyst and an alkylation reagent into the solution, heating the mixture to between 60 and 105 DEG C by stirring, reacting the mixture for 5 to 18 hours through heat preservation, cooling and crystallizing the reaction solution after the reaction is finished, stirring and filtering the solution, taking a filter cake out, and washing and drying the filter cake to obtain an aniline alkylation product expressed by formula (2). The method has the main following advantages that: (1) quaternary ammonium salt and dispersant used as a mixed catalyst in the method have obvious effect of promoting the reaction, can prevent oil-water demixing, can balance the system after the reaction is finished, and are easy to crystallize; and (2) by adopting the acid-catching agent provided by the method, the pH value can be well controlled and stabilized, the hydrolysis of acyl and halogenated hydrocarbon can be effectively prevented, and the occurrence of side reaction and the consumption of the halogenated hydrocarbon can be reduced; and the cost can be reduced and the cost performance can be improved by using heavy magnesium oxide as the acid-catching agent in particular.

Description

(1) Technical field [0001] The invention relates to an alkylation preparation method of aniline intermediates, in particular to an alkylation preparation method of aniline intermediates widely used in dye synthesis. (2) Background technology [0002] Aniline intermediates are the most important raw materials in the synthesis of dyes, for example, 3-amino-4-methoxyacetanilide is an important intermediate for the production of blue-black series disperse dye coupling components, which can be used to produce disperse black EX-SF , Disperse Blue EX-SF, Disperse Dark Blue HGL, Disperse Blue 301, Disperse Blue 291, Disperse Blue 291:1, Disperse Blue 281, etc.; while 3-acetamidoaniline is mainly used to produce Disperse Violet 93, Disperse Blue 165, Disperse Blue Blue 183, Disperse Blue 257 and Disperse Blue 367, etc., related dyes are in great demand at home and abroad. [0003] Usually, such intermediates react with halogenated alkanes or halogenated alkanes to obtain substituted...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C233/43B01J31/02
Inventor 高怀庆钟玉霞徐建康王德义
Owner 浙江龙盛染料化工有限公司
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