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A kind of preparation method of 4-chloro-2,5-dimethoxyacetoacetanilide

A technology of dimethoxyacetoacetanilide and dimethoxyaniline, applied in the field of preparation of 4-chloro-2,5-dimethoxyacetoacetanilide, can solve incomplete reaction, complicated process and environmental pollution and other problems, to achieve the effect of promoting reaction conversion, increasing reaction yield, and reducing solvent consumption

Active Publication Date: 2017-04-05
XIANGSHUI HENRYDA TECH CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (1) The reaction is incomplete, the yield is only 90%, and a large amount of impurities are produced;
[0007] (2) The process is complicated and there are many steps;
[0008] (3) A large amount of waste water is produced in the process, which needs to be treated, which will increase the cost and cause environmental pollution

Method used

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  • A kind of preparation method of 4-chloro-2,5-dimethoxyacetoacetanilide
  • A kind of preparation method of 4-chloro-2,5-dimethoxyacetoacetanilide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 30g of 4-chloro-2,5-dimethoxyacetoacetanilide (0.15mol) into a 250ml four-port reaction vessel, add 120ml of 95% ethanol, start stirring, and start to drop 15g of diketene ( 0.18mol), added dropwise within 3 hours, heated up to 60°C, reacted for 3 hours, cooled to 0-2°C after the reaction was completed, filtered, and dried to obtain 39.9g of the product as a white crystal, with a yield of 91.3%. The product is shiny, with a melting point of ≥105°C and a purity of 99.5%. At the same time, the filtered mother liquor is collected and used for the next batch of reactions.

Embodiment 2

[0029] This example provides a preparation method of 4-chloro-2,5-dimethoxyacetoacetanilide, which is basically the same as that of Example 1. The difference is: the filtered mother liquor collected in Example 1 is used as the reaction bottom solution in the following 8 reactions to repeat the cycle, and an average of 42.40g of 4-chloro-2,5-dimethoxyacetoacetanilide can be obtained, and the yield It is 97.2%, a white crystal, shiny, melting point ≥ 105 ℃, purity ≥ 99.5%. Collect and filter the mother liquor. Each batch of product yield, weight and purity are shown in Table 1.

[0030] Table 1

[0031] Mother liquor cycle times Product weight / g Product yield / % purity / % 0 39.9 91.3 99.50 1 42.88 98.2 99.54 2 42.55 97.5 99.61 3 42.70 98.4 99.82 4 42.54 97.6 99.74 5 42.30 97.1 99.81 6 43.02 98.6 99.61 7 42.92 98.3 99.54 8 42.80 97.9 99.43 average 42.40 97.2 99.62

Embodiment 3

[0033] Add 30g of 4-chloro-2,5-dimethoxyacetoacetanilide into a 250ml four-port reaction vessel, add 120ml of 95% ethanol, start stirring, start to add 15g of diketene dropwise at 10°C, and drop it within 3 hours After the addition, heat up to 20°C and react for 6 hours. After the reaction, cool down to 0-2°C, filter and dry to obtain 39.5 g of white crystals with a yield of 90.5%. The product is shiny and has a melting point of ≥105°C , with a purity of 99.6%. At the same time, the filtered mother liquor was collected and used for the next batch of reactions. 8 batches were applied circularly, and the average yield was about 96.4%.

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Abstract

The invention relates to a preparation method of 4-chloro-2,5-dimethoxyacetyl acetanilide. The preparation method comprises the following implementation processes: adding an organic solvent and 4-chloro-2,5-dimethoxyaniline to a reaction vessel, dropwise adding diketone at 10-100 DEG C, completing adding diketone after about 0.5-5 hours and then carrying out heat insulation reaction for 0.5-4 hours, cooling the reactant to 0-10 DEG C after reaction is finished, carrying out emptying and filter pressing so as to obtain a crystal substance, namely 4-chloro-2,5-dimethoxyacetyl acetanilide, and circularly applying the filtrate mechanically. The method has the advantages that the obtained product has good quality and high yield; the method is low in cost, achieves zero discharge or micro-discharge of wastewater, meets the environment-friendly production requirement, is simple and convenient to operate and conveniently achieves industrialization.

Description

technical field [0001] The invention relates to a preparation method of fine chemical products, in particular to a preparation method of 4-chloro-2,5-dimethoxyacetoacetanilide. Background technique [0002] 4-Chloro-2,5-dimethoxyacetoacetanilide (naphthol AS-IRG), whose structure is shown in formula I, is a kind of important fine chemical intermediate, and is widely used in the dye industry, such as for Manufacture of organic pigment yellow 83#, etc., has a large market demand. [0003] [0004] In the traditional preparation method, water is used as a solvent, 4-chloro-2,5-dimethoxyaniline is dissolved in hydrochloric acid solution, and diketene is added dropwise at 40-50°C for reaction. Cool and crystallize and filter to obtain the crude product, then dissolve the crude product in water with liquid alkali, filter to remove impurities, then neutralize with glacial acetic acid to precipitate 4-chloro-2,5-dimethoxyacetoacetanilide, and dry to obtain the finished product. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/80C07C231/04
Inventor 张正富易元龙钱伟林
Owner XIANGSHUI HENRYDA TECH CHEM
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