Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthetic method for 2,6-diisopropyl-4-phenoxy aniline

A technology of diisopropylaniline and phenoxyaniline, which is applied in the field of synthesis of 2,6-diisopropyl-4-phenoxyaniline, can solve the problem of high toxicity of brominated raw materials, which is unfavorable for large-scale production and equipment Harsh requirements and other issues, to achieve the effect of shortening the process cycle, benefiting environmental protection, and avoiding the discharge of waste acid

Active Publication Date: 2014-04-16
XINFA PHARMA
View PDF6 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing method for synthesizing 2,6-diisopropyl-4-phenoxyaniline uses brominated raw materials to react at about 150°C. The disadvantage is that the brominated raw materials have high toxicity, which is not conducive to environmental protection, and the price Expensive, and the reaction cycle is long, the reaction temperature is 140-150°C, the equipment is demanding, the energy consumption is large, the waste water generated is large and difficult to treat, the production cost is high, and it is not conducive to large-scale production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method for 2,6-diisopropyl-4-phenoxy aniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 177.3g (1.0moL) of 2,6-diisopropylaniline, 600mL of toluene and 1.5g of sulfuric acid with a mass concentration of 98% in a 1000mL four-neck flask equipped with stirring, thermometer, reflux condensing device and dropping funnel, Raise the temperature to reflux temperature, slowly add 100.4g (1.1moL) of concentrated nitric acid with a mass concentration of 69wt%, control the reaction temperature at 110°C, keep it for 4h, and the reaction is over, then cool down to 70-80°C, add 373.3g (2moL) Potassium hydroxide with a concentration of 30wt%, 95g (1moL) phenol, and 0.9g catalyst tetrabutylammonium bromide were raised to reflux temperature to remove water in the reaction, and the reaction was completed at 110-112°C for 8 hours, and the organic phase was treated with 10wt% Wash with 150mL×3 sodium hydroxide, dry over anhydrous sodium sulfate, and then evaporate the solvent to obtain a brown solid. The crude product was recrystallized from ethanol to obtain 268.1g of pure...

Embodiment 2

[0029] Add 177.3g (1moL) of 2,6-diisopropylaniline, 600mL o-xylene and 1.5g (catalytic amount) to a 1000mL four-neck flask equipped with stirring, thermometer, reflux condensing device and dropping funnel. 98% sulfuric acid, heat up to 110-115°C, slowly add 109.6g (1.2moL) of concentrated nitric acid with a mass concentration of 68wt% dropwise, control the reaction temperature at 110-115°C, keep it warm for 4.5h, the reaction is over, and then cool down to 70- 80°C, add 373.3g (2moL) of potassium hydroxide with a mass concentration of 30wt%, 95g (1moL) of phenol, and 1.8g of catalyst tetrabutylammonium bromide, raise the temperature to reflux temperature, remove the water in the reaction, and react at 110°C for 8.5 At the end of h, the organic phase was washed with 10wt% sodium hydroxide 150mL×3, dried over anhydrous sodium sulfate, and then the solvent was distilled off to obtain a brown solid. The crude product was recrystallized from ethanol to obtain 268.8g of pure product ...

Embodiment 3

[0031] Add 177.3g (1moL) of 2,6-diisopropylaniline, 600mL toluene and 1.5g (catalytic amount) to a 1000mL four-necked flask equipped with a stirring, thermometer, reflux condensing device and a dropping funnel. The mass concentration is 98%. Sulfuric acid, heat up to reflux temperature, slowly add 105g (1.15moL) of concentrated nitric acid with a mass concentration of 69wt%, control the reaction temperature at 110-115°C, keep it warm for 4h, the reaction is over, then cool down to 70-80°C, add 266.7g (2moL) sodium hydroxide with a mass concentration of 30wt%, 95g (1moL) phenol, and 0.9g catalyst tetrabutylammonium iodide were heated to reflux temperature to remove water in the reaction, and the reaction was completed at 111°C for 8h, and the organic phase was treated with 10wt % sodium hydroxide 150mL×3, dried over anhydrous sodium sulfate, and evaporated the solvent to obtain a brown solid. The crude product was recrystallized from ethanol to obtain 269.0g of pure product, wit...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a synthetic method for 2,6-diisopropyl-4-phenoxy aniline. According to the method, 2,6-diisopropyl aniline is used as a raw material and is dissolved into a solvent; sulfuric acid is added and nitric acid is dropwise added to react to generate 2,6-diisopropyl-4-nitryl aniline; the 2,6-diisopropyl-4-nitryl aniline is not separated and is directly subjected to the next step of a condensation reaction to prepare the 2,6-diisopropyl-4-phenoxy aniline. According to the synthetic method, a quaternary ammonium salt is used as a catalyst and a reaction temperature is reduced to 110 DEG C from 140 DEG C; the requirements on reaction equipment are reduced and the period of a technological process is shortened. The synthetic method is simple to operate, environment-friendly and low in cost, is high in product selectivity, yield and purity, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a synthesis method of 2,6-diisopropyl-4-phenoxyaniline, which belongs to the technical field of pesticide biochemical industry. Background technique [0002] The acaricide diafenthiuron, the trade name is difenuron, and the chemical name is 1-tert-butyl-3(2,6-diisopropyl-4-phenoxyphenyl)thiourea. As one of the new pesticides, diafenthiuron is a high-efficiency insecticide and acaricide of the thiourea family. It has contact killing, stomach poisoning, systemic and fumigation effects, and has a certain ovicidal effect. Effective insecticide and acaricide for pests such as phytophagous mites (Tetranydae, Tarsalidae, whitefly, aphids and leafhoppers) on crops, fruit, ornamentals and vegetables. [0003] The intermediates for the synthesis of diafenthiuron include 2,6-diisopropyl-4-phenoxyaniline, 2,6-diisopropyl-4-phenoxyphenylthiourea, etc. For example, CN100447131A discloses a method for preparing diafenthiuron, using 4-phenox...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C213/00C07C217/90
Inventor 吕强三戚聿新鞠立柱李新发
Owner XINFA PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com