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EP0402048A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Improved process for preparing benzenesulfonate salts

Assignee: EIDP Inc
•
Filing: 1990-05-31
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Granted: —
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Expires: 2010-05-31
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Abstract

Abstract An improved process for preparing benzene­sulfonate salts, such as 4-nonanoyloxybenzenesulfonic acid, sodium salt, from an appropriately substituted acid chloride or chloroformate and an hydroxybenzene­sulfonic acid in which the reaction is conducted in the presence of a phase transfer catalyst selected from quaternary ammonium and quaternary phosphonium salts.

Inventors

  • 👤 Donald Joseph Dumas
  • 👤 Vinayakam Subramanyam

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-03 23:11
CPC Classifications
C; C07; C07C; C07C303/00; C07C303/32

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 217 words
A process for preparing benzenesulfonate salts of the formula (I) RCO₂PhSO₃M      (I) where: R is C₁-C₂₀ linear alkyl; C₁-C₁₅ alkyl substituted by N(R₁)COR₂, CONR₁R₂, CO₂R₃, OR₃ or SO₂R₃; OR₃; CH=CHCO₂R₃; phenyl substituted by CO₂R₃; CH(OR₃)₂; CH(SO₂R₃)₂; C(R₄)(R₅)Cl; C(R₇)₂OC(O)R₆; or CH₂OR₈; R₁ is H or C₁-C₁₀ alkyl, aryl or alkaryl; R₂ is C₁-C₁₄ alkyl, aryl or alkaryl; R₃ is C₁-C₂₀ alkyl, alkenyl, alkynyl or alkaryl, optionally alkoxylated with one or more ethyleneoxy or propyleneoxy groups or mixtures thereof; R₄ is C₄-C₁₄ alkyl or alkenyl; R₅ is H, methyl or ethyl; R₆ is C₁-C₂₀ linear or branched alkyl, alkylethoxyalkylated, cycloalkyl, aryl or substituted aryl; R₇ are independently H, C₁-C₂₀ alkyl, aryl, C₁-C₂₀ alkylaryl and substituted aryl; R₈ is aryl optionally substituted by C₁-C₅ alkyl; and M is selected from an alkali metal or an alkaline earth metal by reacting an acid chloride or chloroformate of the formula (II) RCOCl      (II) with a phenol sulfonic acid of the formula (III) HOPhSO₃M      (III) in an inert aprotic solvent having a boiling point above 100°C, the improvement comprising reacting said acid chloride with said phenol sulfonic acid in the presence of from 0.1 to 10 mole percent of a phase transfer catalyst selected from quaternary ammonium and quaternary phosphonium salts based on the amount of phenol sulfonic acid present in the reaction.
Claim 2
Dependent Claim 217 words
A process for preparing benzenesulfonate salts of the formula (I) RCO₂PhSO₃M      (I) where: R is C₁-C₂₀ linear alkyl; C₁-C₁₅ alkyl substituted by N(R₁)COR₂, CONR₁R₂, CO₂R₃, OR₃ or SO₂R₃; OR₃; CH=CHCO₂R₃; phenyl substituted by CO₂R₃; CH(OR₃)₂; CH(SO₂R₃)₂; C(R₄)(R₅)Cl; C(R₇)₂OC(O)R₆; or CH₂OR₈; R₁ is H or C₁-C₁₀ alkyl, aryl or alkaryl; R₂ is C₁-C₁₄ alkyl, aryl or alkaryl; R₃ is C₁-C₂₀ alkyl, alkenyl, alkynyl or alkaryl, optionally alkoxylated with one or more ethyleneoxy or propyleneoxy groups or mixtures thereof; R₄ is C₄-C₁₄ alkyl or alkenyl; R₅ is H, methyl or ethyl; R₆ is C₁-C₂₀ linear or branched alkyl, alkylethoxyalkylated, cycloalkyl, aryl or substituted aryl; R₇ are independently H, C₁-C₂₀ alkyl, aryl, C₁-C₂₀ alkylaryl and substituted aryl; R₈ is aryl optionally substituted by C₁-C₅ alkyl; and M is selected from an alkali metal or an alkaline earth metal by reacting an acid chloride or chloroformate of the formula (II) RCOCl      (II) with a phenol sulfonic acid of the formula (III) HOPhSO₃M      (III) in an inert aprotic solvent having a boiling point above 100°C, the improvement comprising reacting said acid chloride with said phenol sulfonic acid in the presence of from 0.1 to 10 mole percent of a phase transfer catalyst selected from quaternary ammonium and quaternary phosphonium salts based on the amount of phenol sulfonic acid present in the reaction.
Claim 3
Dependent Claim 15 words
The process of Claim 1 in which the phase transfer catalyst is a tetraalkylammonium salt.
Claim 4
Dependent Claim 15 words
The process of Claim 1 in which the phase transfer catalyst is a tetraalkylphosphonium salt.
Claim 5
Dependent Claim 14 words
The process of Claim 2 in which the tetraalkylammonium salt is a chloride salt.
Claim 6
Dependent Claim 14 words
The process of Claim 3 in which the tetraalkylphosphonium salt is a chloride salt.
Claim 7
Dependent Claim 44 words
The process of Claim 1, Claim 3 or Claim 5 in which the acid chloride is nonanoyl chloride, the phenol sulfonic acid is 4-hydroxybenzenesulfonic acid, sodium salt, the phase transfer catalyst is tetra- n -butylphosphonium chloride, and the inert aprotic solvent is mixed xylenes.
Claim 8
Dependent Claim 47 words
The process of Claim 1, Claim 3 or Claim 5 in which the acid chloride is octanoyloxyacetyl chloride on nonanoyloxyacetyl chloride, the phenol sulfonic acid is 4-hydroxybenzenesulfonic acid, sodium salt, the phase transfer catalyst is tetra- n -butylphos­phonium chloride, and the inert aprotic solvent is mixed xylenes.
Claim 9
Dependent Claim 42 words
The process of Claim 1, Claim 2 or Claim 4 in which the acid chloride is nonanoyl chloride, the phenol sulfonic acid is 4-hydroxybenzenesulfonic acid, sodium salt, the phase transfer catalyst is tetramethylammonium chloride, and the inert aprotic solvent is mixed xylenes.
Claim 10
Dependent Claim 42 words
The process of Claim 1, Claim 2 or Claim 4 in which the acid chloride is nonanoyl chloride, the phenol sulfonic acid is 4-hydroxybenzenesulfonic acid, sodium salt, the phase transfer catalyst is ALIQUAT® 336, and the inert aprotic solvent is mixed xylenes.

References Cited (Backward Citations)

US4536314A Cited
EP0164796A2 Cited

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