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US3948995A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for converting alkylaromatic hydroperoxides into phenolic products and carbonyl products

Assignee: Rhone Poulenc Textile SA
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Filing: 1974-07-24
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Granted: 1976-04-06
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Expires: 1994-07-24
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Abstract

Abstract A process for splitting primary or secondary alkylaromatic hydroperoxides into phenolic products and carbonyl products is disclosed which consists of reacting the hydroperoxide with a catalytic amount of an acid in the presence of an aprotic polar solvent which is a polymethylene-sulphone or an alkylene glycol carbonate which contains 2 to 4 carbon atoms (in the alkylene part).

Inventors

  • 👤 Michel Jouffret

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 16:12
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/08; C07C45/00; C07C45/51; C07C45/53

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 195 words
In a process for converting a primary or secondary alkylaromatic hydroperoxide of the general formula: ##SPC2## in which: R represents a hydrogen or halogen atom, an alkyl radical containing 1 to 4 carbon atoms, a said alkyl radical substituted by a halogen atom, a nitro or alkoxy radical containing 1 to 4 carbon atoms, a nitro group, or an alkoxy radical containing 1 to 4 carbon atoms; R' represents a hydrogen atom; an alkyl radical containing 1 to 4 carbon atoms; a cycloalkyl radical; an aryl radical; or an aralkyl radical or, when R is in the ortho-position, together with R forms a divalent alkylene radical; and n represents an integer from 1 to 3, into phenolic and/or carbonyl compounds, which comprises reacting the hydroperoxide with a catalytic amount of a acid catalyst in the presence of an inert organic solvent, the improvement wherein the solvent is an aprotic polar solvent selected from a polymethylene-sulphone containing 3 to 6 methylene groups, one or more of said methylene groups optionally being substituted by an alkyl radical with 1 to 4 carbon atoms, and alkylene glycol carbonate containing 2 to 4 carbon atoms in the alkylene part.
Claim 2
Dependent Claim 195 words
In a process for converting a primary or secondary alkylaromatic hydroperoxide of the general formula: ##SPC2## in which: R represents a hydrogen or halogen atom, an alkyl radical containing 1 to 4 carbon atoms, a said alkyl radical substituted by a halogen atom, a nitro or alkoxy radical containing 1 to 4 carbon atoms, a nitro group, or an alkoxy radical containing 1 to 4 carbon atoms; R' represents a hydrogen atom; an alkyl radical containing 1 to 4 carbon atoms; a cycloalkyl radical; an aryl radical; or an aralkyl radical or, when R is in the ortho-position, together with R forms a divalent alkylene radical; and n represents an integer from 1 to 3, into phenolic and/or carbonyl compounds, which comprises reacting the hydroperoxide with a catalytic amount of a acid catalyst in the presence of an inert organic solvent, the improvement wherein the solvent is an aprotic polar solvent selected from a polymethylene-sulphone containing 3 to 6 methylene groups, one or more of said methylene groups optionally being substituted by an alkyl radical with 1 to 4 carbon atoms, and alkylene glycol carbonate containing 2 to 4 carbon atoms in the alkylene part.
Claim 3
Dependent Claim 16 words
A process according to claim 1, in which R' represents a cyclohexyl, phenyl or benzyl radical.
Claim 4
Dependent Claim 19 words
Process according to claim 1, in which the hydroperoxide is benzyl hydroperoxide, p-xylyl hydroperoxide, 1-phenyl-ethyl hydroperoxide or 1,2-diphenyl-ethyl hydroperoxide.
Claim 5
Dependent Claim 18 words
Process according to claim 1, in which the solvent is sulpholane, ethylene glycol carbonate or propylene glycol carbonate.
Claim 6
Dependent Claim 18 words
Process according to claim 1 in which the acid catalyst is an inorganic protonic acid or organosulphonic acid.
Claim 7
Dependent Claim 26 words
Process according to claim 5, in which the protonic acid is selected from hydrochloric acid, nitric acid, sulphuric acid, methanesulphonic acid, benzenesulphonic acid and para-toluenesulphonic acid.
Claim 8
Dependent Claim 21 words
Process according to claim 6, in which the protonic acid is present as pure acid or as a concentrated aqueous solution.
Claim 9
Dependent Claim 27 words
Process according to claim 1, which is carried out in the liquid phase, at a temperature of from 20°C to the boiling point of the reaction mixture.
Claim 10
Dependent Claim 13 words
Process according to claim 8, which is carried out at 50° to 110°C.
Claim 11
Dependent Claim 32 words
Process according to claim 1, in which the acid catalyst is present in an amount from 0.1% to 10% by weight (expressed as pure acid), based on the weight of the hydroperoxide.
Claim 12
Dependent Claim 44 words
Process according to claim 1, which is carried out at 50° to 110°C in the presence of sulpholane, ethylene glycol or propylene glycol carbonate and a protonic acid selected from hydrochloric acid, nitric acid, sulphuric acid, methanesulphonic acid, benzenesulphonic acid and para-toluene sulphonic acid.

References Cited (Backward Citations)

US2853532A Cited
US3497561A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-04-06 1979-10-06 1980-04-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-04-06 1983-10-06 1984-04-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-04-06 1987-10-06 1988-04-06 $7700.00 Window Closed / Lapsed

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