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EP0092909A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Process for producing aminophenyl-beta-hydroxyethylsulfone

Assignee: Sumitomo Chemical Co Ltd
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Filing: 1983-03-25
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Granted: —
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Expires: 2003-03-25
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Abstract

Abstract A process for producing aminophenyl-β-hydroxyethylsulfone of the formula (I), which comprises steps: (1) condensing nitrohalobenzene with mercaptoethanol in the presence of an alkali hydroxide and at least one reaction medium selected from N-alkyl-substituted amides and sulfoxides to produce mono-nitrophenyl-β-hydroxyethylsulfide of the formula (II): (2) oxidizing the mononitrophenyl-β-hydroxyethylsulfide (II) to produce mononitrophenyl-β-hydroxyethylsulfone of the formula (III): and (3) reducing the mononitrophenyl-β-hydroxyethylsulfone to produce the aminophenyl-β-hydroxyethylsulfone of the formula (I). This compound is useful as an intermediate for aminophenyl-β-sulfatoethylsulfone represented by the following formula: which is an important intermeidate for vinyl sulfone type reactive dyes largely used for dyeing cellulose fiber materials.

Inventors

  • 👤 Norio Kotera
  • 👤 Kazuhiro Tada
  • 👤 Shinzaburo Masaki
  • 👤 Kunihisa Goto
  • 👤 Tatsuo Kaneoya

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-07 16:38
CPC Classifications
C; C07; C07C; C07C323/00; C07C317/00

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 69 words
A process for producing aminophenyl-β-hydroxyethylsulfone of the formula (I), which comprises steps, (1) condensing a nitrohalobenzene with mercaptoethanol in the presence of an alkali hydroxide and at least one reaction medium selected from N-alkyl-substituted amides and sulfoxides to produce mononitrophenyl-β-hydroxyethylsulfide of the formula (II), (2) oxidizing the mononitrophenyl-β-hydroxyethylsulfide (II) to produce mononitrophenyl-β-hydroxyethylsulfone of the formula (III), and (3) reducing the mononitrophenyl-S-hydroxyethylsulfone to produce the aminophenyl-β-hydroxyethylsulfone of the formula (I).
Claim 2
Dependent Claim 69 words
A process for producing aminophenyl-β-hydroxyethylsulfone of the formula (I), which comprises steps, (1) condensing a nitrohalobenzene with mercaptoethanol in the presence of an alkali hydroxide and at least one reaction medium selected from N-alkyl-substituted amides and sulfoxides to produce mononitrophenyl-β-hydroxyethylsulfide of the formula (II), (2) oxidizing the mononitrophenyl-β-hydroxyethylsulfide (II) to produce mononitrophenyl-β-hydroxyethylsulfone of the formula (III), and (3) reducing the mononitrophenyl-S-hydroxyethylsulfone to produce the aminophenyl-β-hydroxyethylsulfone of the formula (I).
Claim 3
Dependent Claim 25 words
The process according to Claim 1, wherein mercaptoethanol is used in an amount of ranging from 1 through 3 moles per mole of the nitrohalobenzene.
Claim 4
Dependent Claim 16 words
The process according to Claim 1, wherein the alkali hydroxide is sodium hydroxide or potassium hydroxide.
Claim 5
Dependent Claim 27 words
The process according to Claim 1, wherein the alkali hydroxide is used in an amount of ranging from 1 through 1.2 mole per mole of the nitrohalobenzene.
Claim 6
Dependent Claim 20 words
The process according to Claim 1, wherein the reaction medium has a water content of 2 to 30% by weight.
Claim 7
Dependent Claim 19 words
The process according to Claim 1, wherein the condensing is carried out at a temperature of 30° to 55°C.
Claim 8
Dependent Claim 42 words
The process according to Claim 1, wherein the oxidizing is carried out using hydrogen peroxide in a reaction medium of water or an aqueous reaction medium comprising at least one nitrile in the presence of a basic compound or a metal catalyst.
Claim 9
Dependent Claim 32 words
The process according to Claim 7, wherein the oxidizing is carried out in a reaction medium of water at a temperature of 30° to 100°C at an initial.pH of 3 to 8.
Claim 10
Dependent Claim 37 words
The process according to Claim 7, wherein the oxidizing is carried out in a nitrile-containing aqueous reaction medium at a temperature of 30° to 65°C, while controlling the pH of the reaction system to 7.5 to 10.5.
Claim 11
Dependent Claim 25 words
The process according to Claim 7, wherein the oxidizing is carried out in the nitrile-containing aqueous reaction medium in the presence of a metal catalyst.
Claim 12
Dependent Claim 17 words
The process according to Claim 1, wherein the reducing is carried out by a catalytic reduction method.

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