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Synthetic technology of hydroxyethylaniline ester (III)

A technology of hydroxyethylaniline and dihydroxyethylaniline, which is applied in the field of synthesis technology of hydroxyethylaniline ester compound, can solve problems such as damage to society and people's livelihood, inflammability and explosion, hidden danger of ethylene oxide, etc., and achieve safety High performance, simple process, and the effect of increasing process safety

Inactive Publication Date: 2016-04-13
SHANGHAI CHENGHOUFEI TRADE CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ethylene oxide is a toxic carcinogen. It is a colorless gas with an ether pungent odor at room temperature. It is flammable and explosive and has a wide range of explosive concentrations in the air. Therefore, ethylene oxide The use of
In recent years, explosions caused by the use of ethylene oxide to produce hydroxyethylaniline (II) in conventional tank reactors have occurred frequently at home and abroad, causing immeasurable damage to the people's livelihood

Method used

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  • Synthetic technology of hydroxyethylaniline ester (III)
  • Synthetic technology of hydroxyethylaniline ester (III)
  • Synthetic technology of hydroxyethylaniline ester (III)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (1) Synthesis of N,N-Dihydroxyethylaniline

[0043]Keep the temperature of the microreactor at 80-85°C, add 46.5g of aniline and 44g of ethylene oxide into the microreactor through syringe pumps-1 and -2 respectively, the flow rate of syringe pump-1 is 10mL / min, and the flow rate of syringe pump- The flow rate of 2 is 11mL / min. The reaction was completed to obtain 90.5 g (HPLC: 98.5%) of N,N-dihydroxyethylaniline. The NMR data of N,N-dihydroxyethylaniline are as follows: 1 HNMR (500MHz, CDCl 3 ): δ7.27(t, 2H), 6.94(d, 2H), 6.79(t, 1H), 4.20(t, 2H), 3.73(t, 2H), 3.65(br., 2H).

[0044] (2) Synthesis of N,N-diacetoxyethylaniline

[0045] Keep the microreactor temperature at 105-110°C, add 90.5g (HPLC: 98.5%) N,N-dihydroxyethylaniline and 105g acetic anhydride into the microreactor via syringe pumps -3 and -4, respectively, and the syringe pump The flow rates of -3 and -4 were both 10mL / min. After the reaction was complete, 135.2 g (HPLC: 99%) of crude N,N-diacetoxye...

Embodiment 2

[0047] (1) Synthesis of 2-methoxy-4-acetylamino-N,N-dihydroxyethylaniline

[0048] The temperature of the microreactor was kept at 90-100°C, and 720g of 2-methoxyl-5-acetamidoaniline aqueous solution (made of 180g 2-methoxyl-5-acetamidoaniline and 540g water Composition) and 89g of ethylene oxide were added to the microreactor, the syringe pump-1 was 36mL / min, and the syringe pump-2 was 5mL / min. The reaction was completed to obtain 266.6 g (HPLC: 98%) of 2-methoxy-4-acetamido-N,N-dihydroxyethylaniline. The NMR data of the 2-methoxy-4-acetylamino-N, N-dihydroxyethylaniline are as follows: 1 HNMR (500MHz, CDCl 3 ): δ7.27(br.,1H), 6.94(s,1H), 6.85(d,1H), 6.80(d,1H), 4.21(t,2H), 3.85(s,3H), 3.73(t ,2H), 3.65(br.,2H), 2.02(s,3H).

[0049] (2) Synthesis of 2-methoxy-4-acetylamino-N,N-diacetoxyethylaniline

[0050] Keep the temperature of the microreactor at 105-110°C, and inject 266.6g (HPLC: 98%) of 2-methoxy-4-acetamido-N,N-dihydroxyethylaniline through syringe pumps -3 and -...

Embodiment 3

[0052] (1) Synthesis of 3-methyl-4-(2,2-dicyanovinyl)-N-ethyl-N-hydroxyethylaniline

[0053] Keep the temperature of the microreactor at 90-100°C, and inject 1266g of 3-methyl-4-(2,2-dicyanovinyl)-N-ethylaniline aqueous solution [from 211g3 -Methyl-4-(2,2-dicyanovinyl)-N-ethylaniline and 1055g of water] and 48.4g of ethylene oxide were added to the microreactor, the syringe pump-1 was 50mL / min, and the injection Pump-2 was 1.9 mL / min. The reaction was completed to obtain 257.6 g (HPLC: 96.6%) of 3-methyl-4-(2,2-dicyanovinyl)-N-ethyl-N-hydroxyethylaniline. The 3-methyl-4-(2,2-dicyanovinyl)-N-ethyl-N-hydroxyethylaniline such as: 1 HNMR (500MHz, CDCl 3 ): δ8.06(s,1H), 7.10(d,1H), 6.63(s,1H), 6.52(d,1H), 4.24(t,2H), 3.75(t,2H), 3.66(br. ,1H), 3.41(q,2H), 2.50(s,3H), 1.16(t,3H).

[0054] (2) Synthesis of 3-methyl-4-(2,2-dicyanovinyl)-N-ethyl-N-benzoyloxyethylaniline

[0055] Keep the temperature of the microreactor at 105-110°C, and inject 257.6g (HPLC: 96.6%) of 2-methoxy-4-...

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Abstract

The invention discloses a synthetic technology of hydroxyethylaniline ester (III). The synthesis process is shown by a chemical equation shown in the description. The technology has the following advantages: 1, the advantage of few instant reaction substances of a micro-channel reactor is used, so the flammable and explosive disadvantages of a hydroxyethylation reaction in a routine kettle are solved, the process safety is increased, and current chemical engineering safety operation requirements are met; and 2, the advantage of high mixing efficiency of the micro-channel reactor is used, the reaction can be carried out under solvent-free conditions when a hydroxyethylation reaction raw material is liquid, and when the excess amount of ethylene oxide is very small, so a reaction solution obtained after the hydroxyethylation reaction ends can be esterified in the micro-channel reactor, serial operation of two-step reactions is realized, and manpower and three wastes are greatly reduced. The technology is a new technology with simplified processes, and accords with environmental protection and safety requirements.

Description

technical field [0001] The invention relates to a synthesis process of organic compounds, in particular to a synthesis process of hydroxyethylaniline ester compound (III). Background technique [0002] Hydroxyethylaniline ester compound (III, ) is 79 # Blue, 30 # Orange, 51 # Orange, 5 # It is an important synthetic intermediate of a series of disperse dyes such as red, and the development of an economically and technically feasible synthetic process of hydroxyethylaniline ester compound (III) with high industrial safety and less "three wastes" has great significance for the synthesis of dyes and their intermediates. pivotal role. [0003] At present, the industrial production process of hydroxyethylaniline ester compound (III) basically uses the corresponding aniline as the main starting material, which is synthesized by hydroxyethylation reaction with excess ethylene oxide in an appropriate solvent. Ethylene oxide is a toxic carcinogen. It is a colorless gas with a ...

Claims

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Application Information

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IPC IPC(8): C07B41/12C07C213/06C07C213/04C07C231/12C07C253/30C07C219/06C07C215/16C07C233/43C07C255/42
CPCC07B41/12C07C213/04C07C213/06C07C231/12C07C253/30C07C219/06C07C215/16C07C233/43C07C255/42
Inventor 邵玉田邱宇飞
Owner SHANGHAI CHENGHOUFEI TRADE CO LTD
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