EP0402048A1
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Improved process for preparing benzenesulfonate salts
Assignee: EIDP Inc
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Filing: 1990-05-31
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Granted: —
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Expires: 2010-05-31
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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