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

Preparation method of aniline derivative containing 2-hydroxyethylsulfonyl

A technology of hydroxyethylsulfone-based aniline and derivatives, which is applied in the field of fine chemical industry, can solve the problems of large discharge of waste water and waste residue, low product quality, and pollution of three wastes, etc., and achieves simple equipment, high product yield and convenient operation. Effect

Inactive Publication Date: 2007-09-19
DALIAN UNIV OF TECH
View PDF1 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The iron powder reduction process has the following disadvantages: high consumption, low product quality, especially large discharge of waste water and waste residue, resulting in serious pollution of three wastes

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
  • Preparation method of aniline derivative containing 2-hydroxyethylsulfonyl
  • Preparation method of aniline derivative containing 2-hydroxyethylsulfonyl
  • Preparation method of aniline derivative containing 2-hydroxyethylsulfonyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: 69.3g (0.3mol) 3-(2-hydroxyethyl sulfone group) nitrobenzene is joined in 700ml methyl alcohol, is warming up to 65 ℃, adds 1.4g 0.5% palladium carbon, drips 28ml hydrazine hydrate ( Content 80%). Reflux at this temperature for 6-8 hours, use thin layer chromatography in developing solvent: chloroform: acetone = 8: 2 (v / v) to detect the disappearance of raw materials, which is the end point of reduction. The palladium carbon was removed by filtration, the filtrate was evaporated to dryness under reduced pressure (the distilled methanol was recovered and used mechanically), the residue was diluted with water, filtered to obtain a filter cake, and dried to obtain 59 g of the product, with a yield of 98%.

Embodiment 2

[0058] Embodiment 2: 86g (0.2mol) 4-nitro-N-[2-sulfonic acid group-4-(2-hydroxyethyl sulfone group) phenyl) benzamide is added to 650mol water and 50ml dimethyl In formamide, heat up to 100°C, add 5g of ferric trichloride-carbon, dropwise add 20ml of hydrazine hydrate, and reflux at 98-100°C for 10-12 hours. After the reaction reached the end point, the catalyst was removed by filtration, and the solvent was evaporated to obtain 72 g of solid, which was the product, with a yield of 90%.

Embodiment 3

[0059] Embodiment 3: 87.5g 4-nitro-N-[3-(2-hydroxyethyl sulfone group) phenyl) benzamide is added in 700ml ethanol, is warmed up to 78 ℃, adds 45ml hydrazine hydrate (content 50 %) and 3.5g ferric oxyhydroxide, reflux at 78-80°C for 8-10 hours. After the reaction reached the end point, the catalyst was removed by filtration while it was hot. After the filtrate was cooled, light off-white crystals were precipitated. After drying, 72 g of dry product was obtained, with a yield of 90%. The collected filtrate can be applied directly.

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

A method for manufacturing a product containing 2-ethoxylsulfurylaniline derivant belongs to meticulous chemical which is characterized in that having the water, carbinol, ethanol, n-propyl alcohol, lsopropylalcohol, n-butanol, 2-Methyl-1-propanol, dioxane, tetrahydrofuran, dimethyl formamide or their mixture as solvent, adding the 2-ethoxylsulfurylnitrobenzene derivant into solvent, blending and heating to 40-100 DEG C, adding the catalyzer after the reduzate being wholly or partly dissolved, and dripping Hydrazine hydrate; reacting for 0.2-12 hours, filtering to removing the catalyzer while it is hot after finishing the thin-layer chromatography detecting reaction. The products are obtained by three means: (1) decompressing and distilling the filtrate, recovering the solvent, diluting the residual in the cold water or ice water and filtering; (2) directly distilling the solvent from the filtrate; (3) precipitating the product after cooling the filtrate, filtering, and the filtrate being directly applied. The invention has a simple equipment, a convenient operation, a high production yield, a good quality, a high purity and a fine environment friendship.

Description

technical field [0001] The invention belongs to the field of fine chemical industry, and relates to a method for preparing 2-hydroxyethylsulfonyl aniline derivatives by reducing nitrobenzene derivatives containing 2-hydroxyethylsulfone. Background technique [0002] Aniline derivatives containing 2-hydroxyethyl sulfone are important intermediates for the synthesis of reactive dyes, and most of them are prepared by reducing the corresponding nitro compounds with iron powder. The iron powder reduction process has the following disadvantages: high consumption, low product quality, especially large discharge of waste water and waste residue, resulting in serious pollution of three wastes. [0003] According to the patent report, m-2-hydroxyethylsulfone aniline can be prepared by low-pressure catalytic hydrogenation reduction of m-2-hydroxyethylsulfone nitrobenzene (CN0219594.3), which requires a hydrogen source and an autoclave. The patent (Application No. 2006102006559) introd...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/40C07C315/04
Inventor 吕荣文石奇勋高崑玉
Owner DALIAN UNIV OF TECH
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