Preparation method of 1, 2-di (o-amino phenoxyl) ethane

A technology of o-aminophenoxy and nitrophenoxy, which is applied in the field of compound preparation, can solve problems such as gaps, and achieve the effects of low cost, stable quality and high yield

Active Publication Date: 2013-04-10
淄博圣马化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to obtain 1,2-bis(o-aminophenoxy)ethane, 1,2-bis(o-nitrophenoxy)ethane must be reduced. Foreign literature reports that the hydrazine hydrate route is basically Pd / C Or metal catalytic reduction methods such as Ruan's nickel, domestic related articles have reported that the product adopts the iron-carbon reduction route, and "Chemical Reagents" 199517 (1) 49-50 reported the same route as ours, but the report said The yield that can be achieved is only 86%, which has a large gap compared with the yield of this patent

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In a 500ml four-necked bottle that has been installed stirring, reflux condenser, thermometer, dropping funnel, add the o-nitrochlorobenzene of 100g (0.635mol), 30g dodecyltrimethylammonium chloride phase-transfer catalyst, 19.7g (0.318mol) ethylene glycol, 13.5g (0.127mol) sodium carbonate, make o-nitrochlorobenzene and sodium carbonate mol ratio 1: 0.2, add, open condenser cooling water, open heating mantle heating system, wait After the organic matter in the system melted, the stirring was started, and the temperature of the system was slowly raised to 60°C. Within 1.0 hour, 76.2g of 35% (0.667mol) sodium hydroxide was uniformly added dropwise to the system, so that the ratio of o-nitrochlorobenzene and sodium hydroxide was 1: 1.05. After the dropwise addition, the temperature of the system was kept at 64-66°C . After continuing to react for 12 hours, remove the heating mantle, cool the system to 30-35° C. with a water bath, and filter with a Buchner funnel. The pr...

Embodiment 2

[0020] In a 500ml four-necked bottle that has been installed stirring, reflux condenser, thermometer, dropping funnel, add the o-nitrochlorobenzene of 100g (0.635mol), 30g dodecyltrimethylammonium chloride phase-transfer catalyst, 19.7g (0.318mol) ethylene glycol, 17.5g (0.127mol) sodium carbonate, make o-nitrochlorobenzene and sodium carbonate molar ratio 1: 0.2, add, open condenser cooling water, open heating mantle heating system, wait After the organic matter in the system is melted, start stirring, and slowly raise the temperature of the system to 60° C., and then within 1.0 hour, uniformly dropwise add 149.5 g of 25% (0.667 mol) sodium hydroxide solution to the system to make o-nitrochlorobenzene and hydrogen The ratio of sodium oxide is 1:1.05. After the dropwise addition, keep the system temperature at 64-66°C and continue the reaction for 12 hours, then remove the heating mantle, cool the system to 30-35°C with a water bath, and filter with a Buchner funnel. The produ...

Embodiment 3

[0023] In a 500ml four-necked bottle that has been installed stirring, reflux condenser, thermometer, dropping funnel, add the o-nitrochlorobenzene of 100g (0.635mol), 30g dodecyltrimethylammonium chloride phase-transfer catalyst, 19.7g (0.318mol) ethylene glycol, make o-nitrochlorobenzene and sodium carbonate molar ratio 1: 0, after adding, turn on the condenser cooling water, turn on the heating mantle heating system, after the organic matter of the system is melted, turn on the stirring, put The temperature of the system was slowly raised to 60° C., and then within 1.0 hour, 106.7 g of 35% (0.933 mol) sodium hydroxide was uniformly added dropwise to the system, so that the ratio of o-nitrochlorobenzene to sodium hydroxide was 1:1.469. After the dropwise addition, keep the system temperature at 60-63°C and continue the reaction for 12 hours, then remove the heating mantle, cool the system to 30-35°C with a water bath, filter with a Buchner funnel, and wash the product with 10...

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PUM

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Abstract

The invention provides a preparation method of 1, 2-di (o-amino phenoxyl) ethane, belonging to the technical field of a compound preparation method, in particular to a preparation method of a fine chemical industrial midbody. The preparation method is characterized by sequentially comprising the two steps of: condensing o-nitro chlorobenzene with glycol under the existence of sodium carbonate, sodium hydroxide and phase transfer catalyst to prepare 1, 2-(o-nitro phenoxyl) ethane; and reducing the 1, 2-(o-nitro phenoxyl) ethane in organic solvent with hydrazine hydrate to prepare the 1, 2-di (o-amino phenoxyl) ethane. The yield of the two steps is obviously higher than that of the other document reports, and the purity of the product is higher than 99%. The method not only has low cost, but also has stable yield quality, thereby being a synthesis method which can be completely realized in the industrial production. The catalyst has low price and high yield; and the organic solvent is carbinol or alcohol, and has low price. The method nearly has no three wastes.

Description

technical field [0001] The invention belongs to the technical field of compound preparation methods, and in particular relates to a preparation method of a fine chemical intermediate. Background technique [0002] 1,2-bis(o-aminophenoxy)-ethane is a valuable fine chemical intermediate, in addition to being used in the synthesis of C.I. organic pigment yellow 180, it is also used in many dyes, paints, medicines, oils It is an important intermediate for product additives and Schiff base macrocycles. In the late 1990s, with the continuous expansion of the application field of 1,2-bis(o-aminophenoxy)-ethane terminal fine chemical products, especially Pigment Yellow 180, many domestic scientific research institutions focused on the development and research of this product also became active. But so far, the research results in this area generally have defects such as high cost, poor application performance of the product, and harsh conditions of the synthesis process, making it...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/84C07C213/02
Inventor 谭立哲于先进张小华
Owner 淄博圣马化工有限公司
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