Method for preparing 5-amino-2-chloro-N-(2,4-xylyl)-benzene sulfonic amide in water phase

A technology of xylyl and benzenesulfonamide, applied in the preparation of sulfonic acid amide, organic chemistry and other directions, to achieve the effects of clean production, mild reaction conditions and simple process

Inactive Publication Date: 2009-07-08
WENZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the preparation of 5-amino-2-chloro-N-(2,4-xylyl)-benzenesulfonamide by catalytic hydrogenation method. In the aqueous phase, 5-nitro-2-chloro-N- Catalytic hydrogenation of (2,4-xylyl)-benzenesulfonyl to prepare 5-amino-2-chloro-N-(2,4-xylyl)-benzenesulfonamide

Method used

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  • Method for preparing 5-amino-2-chloro-N-(2,4-xylyl)-benzene sulfonic amide in water phase
  • Method for preparing 5-amino-2-chloro-N-(2,4-xylyl)-benzene sulfonic amide in water phase
  • Method for preparing 5-amino-2-chloro-N-(2,4-xylyl)-benzene sulfonic amide in water phase

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Take 1.45g of palladium chloride and dissolve it in water, and use 5% dilute nitric acid to adjust the pH value of the solution to about 2~3, cool in an ice-salt bath to 0°C, and add 0.5mol / L of KBH dropwise under stirring 4 Until the solution is free of gas, adjust the pH value to 11 with 10mol / L NaOH solution to make a pre-prepared solution, and then spray the pre-prepared solution on 30g of γ-Al 2 o 3 on the carrier, let it stand for 2h, filter, wash the catalyst with deionized water until the pH value of the washing solution is 7, and then wash the catalyst 3 times with absolute ethanol to obtain Pa-B / Al 2 o 3 catalyst. Store the catalyst in absolute ethanol for later use. The total catalyst loading was 3%.

[0027] In a 50ml autoclave reactor, add 3g of 5-nitro-2-chloro-N-(2,4-xylyl)-benzenesulfonamide, dissolve in 30ml of water, 0.3g of Pa-B / al 2 o 3 Catalyst, close the autoclave reactor, put the reactor on an oil bath and fix it, replace the air in the re...

Embodiment 2

[0029] Dissolve 0.378g of palladium hydrochloride and 1.134g of ruthenium chloride in water, and use nitric acid to adjust the pH value of the solution to about 2 to 3, and then spray the prepared solution on 30g of γ-Al 2 o 3 On the carrier, let it stand for 3 hours, and turn it every 30 minutes. Dry it in an oven at 130°C for 10 hours, then put it into a muffle furnace, and roast it at a gradient temperature of 160-450°C. The roasting method is as follows: 160°C, 2h; 200°C, 2h; 300°C, 2h; 400°C, 2h; 450°C, 2h. After natural cooling, the catalyst is put into a closed container for use. The mass dosage of the active component is γ-Al based on the active component therein 2 o 3 3% of the mass of the carrier feed.

[0030] In a 50ml autoclave reactor, add 3g of 5-nitro-2-chloro-N-(2,4-xylyl)-benzenesulfonamide, dissolve in 30ml of water, 0.4g of Pa-Ru / al 2 o 3 Catalyst, airtight autoclave reactor, the reactor is placed on the oil bath and fixed, and the air in the react...

Embodiment 3

[0032] Dissolve 1.987g of nickel chloride in water, and use 5% dilute nitric acid to adjust the pH of the solution to about 2-3, and add 0.5mol / L of KBH dropwise under stirring 4 Until the solution has no gas generation, adjust the pH value to 12 with an aqueous alkali solution to make a pre-prepared solution, and then spray the pre-prepared solution on 30g of γ-Al 2 o 3 on the carrier, let it stand for 2 hours, cooled to 0°C in an ice-salt bath, filtered, washed the catalyst with deionized water until the pH value of the washing solution was 7, and then washed the filter cake with absolute ethanol 3 times to obtain Ni-B / Al 2 o 3 catalyst. Store the catalyst in absolute ethanol for later use. The catalyst loading was 3%.

[0033] In a 50ml autoclave reactor, 2.5g of 5-nitro-2-chloro-N-(2,4-xylyl)-benzenesulfonamide was added, dissolved in 30ml of water, 0.3g of Ni-B / Al 2 o 3 Catalyst, airtight autoclave reactor, the reactor is placed on the oil bath and fixed, the air ...

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Abstract

The invention discloses a method for preparing 5-amino-2-chlorine-N-(2,4-xylyl)-benzsulfamide of which the structure is as shown in a formula (II) in a water phase, which comprises: performing catalytic hydrogenation reaction on 5-nitryl-2-chlorine-N-(2,4-xylyl)-benzsulfamide of which the structure is as shown in a formula (I) in a water solvent in a closed reactor under the action of a supported catalyst under the condition of stirring, and preparing target products, wherein the temperature of the catalytic hydrogenation reaction is between 30 and 150 DEG C, and the pressure in the closed reactor is between 0.1 and 4.0 MPa; a supporter of the supported catalyst is gamma-Al2O3; and active ingredients of the gamma-Al2O3 are one or complexes of more than two of Pa, Ru, Pt, Ni, Fe, Co, Sn, Ge, Al, Zn, Ce and Au in any proportion, or complexes of non-metal B or P and metals in any proportion. The method is performed in the water phase, and has the advantages of high conversion rate, high selectivity, mild reaction conditions, simple technique, clean production and no pollution.

Description

1. Technical field [0001] The invention relates to a method for preparing 5-amino-2-chloro-N-(2,4-xylyl)-benzenesulfonamide in aqueous phase. 2. Background technology [0002] 5-Amino-2-chloro-N-(2,4-xylyl)-benzenesulfonamide is an important intermediate in organic synthesis and is widely used in the fields of fluorescent pigments, dyes, medicine and pesticides. At present, 5-nitro-2-chloro-N-(2,4-xylyl)-benzenesulfonamide is mainly used as raw material at home and abroad. In acidic medium, iron powder is used as reducing agent to carry out nitration on benzene ring. The reduction of the base, the reaction formula is as follows: [0003] [0004] This is a chemical reduction method, which has environmental pollution and safety hazards, and the production capacity is also limited. At present, people try to complete the reduction reaction by means of catalytic hydrogenation. [0005] Take a closer look at this reaction, which is a hydrogenation reaction of chloronitroben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/44C07C303/40
Inventor 赵亚娟司朗诵金雪华吴华悦任宝东晁国库
Owner WENZHOU UNIVERSITY
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