Preparation method of N-methylene-2-methyl-6-ethylaniline

An ethylaniline and methylene technology, which is applied in the field of preparation of aniline compounds, can solve the problems of unstable methylidene, large environmental pollution, blocked pipelines, etc., and achieves improved synthesis yield and purity, excellent polymerization inhibition performance, The effect of stabilizing the reaction speed

Active Publication Date: 2009-10-28
NUTRICHEM LAB CO LTD
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AI Technical Summary

Problems solved by technology

[0006] At present, the domestic acetochlor synthesis method is mainly the chlorinated ether method, which has many problems: many "three wastes" are discharged, causing great environmental pollution, and the product contains carcinogenic chloromethyl ethyl ether, which affects product safety
[0007] However, certain problems also exist in the methylene production process of acetochlor: due to the instability of the generated methylene, it is easy to polymerize to form a gel, thereby blocking the pipeline, reducing the yield, and affecting the purity of the product; Production brings difficulties
[0009] In the prior art, solid substances or solid mixtures are selected as polymerization inhibitors, so there are still certain difficulties in continuous and uniform feeding in industrial production.

Method used

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  • Preparation method of N-methylene-2-methyl-6-ethylaniline

Examples

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Effect test

Embodiment 1

[0026] Example 1 0.01:1

[0027] Take 151g of 99% 2-methyl-6-ethylaniline, 0.98g of ethylenedithiol with 99% polymerization inhibitor, 54.3g of paraformaldehyde, and 0.68g of triethylamine, and add them to a 500mL four-necked reaction flask , stirred, heated to 100° C., reacted for 2 hours, dehydrated under reduced pressure, and then evaporated excess formaldehyde under reduced pressure to obtain 160.1 g of methylene, with a content of 98.0% and a yield of 96.39%.

Embodiment 2

[0028] Example 2 0.02:1

[0029] Take 151g of 99% 2-methyl-6-ethylaniline, 1.95g of ethylenedithiol with 99% polymerization inhibitor, 54.3g of paraformaldehyde, and 0.68g of triethylamine, and add them to a 500mL four-necked reaction flask , stirred, heated to 95° C., reacted for 2 hours, dehydrated under reduced pressure, and then evaporated excess formaldehyde under reduced pressure to obtain 161.7 g of methylene, with a content of 98.5% and a yield of 97.85%.

[0030] Take 136.7g of 98.5% chloroacetyl chloride and put it into a 500ml four-necked reaction flask. After nitrogen replacement, add 161.7g of 98.5% methylene chloride, and keep the reaction at 80-100°C for 2 hours.

[0031] Add 75g of absolute ethanol to another 500ml four-necked bottle, lower the temperature to 0-10°C, then transfer the above-mentioned reaction materials to the dropping funnel while hot, and complete the dropwise addition within 1 hour, 50-55 The reaction was incubated between ℃ for 2 hours. Af...

Embodiment 3

[0032] Example 3 0.04:1

[0033] Take 151g of 99% 2-methyl-6-ethylaniline, 3.9g of ethylenedithiol with 99% polymerization inhibitor, 54.3g of paraformaldehyde, and 0.68g of triethylamine, and add them to a 500mL four-necked reaction flask , stirred, heated to 85° C., reacted for 2 hours, dehydrated under reduced pressure, and then evaporated excess formaldehyde under reduced pressure to obtain 162 g of methylene, with a content of 98.4% and a yield of 97.93%.

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Abstract

The invention provides a preparation method of N-methylene-2-methyl-6-ethylaniline, which takes a liquid organosulfur compound as a polymerization inhibitor; and the N-methylene-2-methyl-6-ethylaniline is generated by the condensation reaction and then the dehydration reaction between 2-methyl-6-ethylaniline and paraformaldehyde. The polymerization inhibitor prevents the generation of the polymerization reaction of a target object and reduces the possibility of condensation reaction, thus stabilizing the reaction rate, simplifying the technological operation, and improving the purity and yield of the target object, namely, methene; the content of the methene is more than 98 percent, and the synthesis yield is more than 96 percent, thus guaranteeing the quality of the final product, namely, acetochlor. The method is suitable for large-scale industrialized production, and has more significant economic benefit.

Description

technical field [0001] The invention relates to a method for preparing aniline compounds, in particular to a method for preparing N-methylene-2-methyl-6-ethylaniline by using a novel polymerization inhibitor. Background technique [0002] Acetochlor, English common name Acetochlor, chemical name: 2'-methyl-6'-ethyl-N-(ethoxymethyl)-2-chloroacetanilide, was developed by Monsanto Company of the United States in 1971 The selective pre-emergent herbicide produced can control annual grass weeds and some broad-leaved weeds. Acetochlor is absorbed through the young shoots and roots of weeds, and inhibits the protein synthesis of weeds to kill the weeds. It is one of the ideal substitutes for lasso (namely alachlor). [0003] The chemical structural formula of acetochlor is as follows: [0004] [0005] Acetochlor [0006] At present, the domestic acetochlor synthesis method is mainly the chlorinated ether method, which has many problems: many "three wastes" are discharged, ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/04C07C249/02
Inventor 李俊卿李生学母灿先邢文龙彭涛高艳博李咏静张政陈晓晖张新国
Owner NUTRICHEM LAB CO LTD
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