US3978141A
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Process for splitting alkylaromatic hydroperoxides into phenolic compounds
Assignee: Rhone Poulenc SA
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Filing: 1974-08-28
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Granted: 1976-08-31
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Expires: 1994-08-28
Abstract
Abstract Process for splitting primary alkylaromatic hydroperoxides to yield phenolic products is described which consists of reacting the hydroperoxide with a catalytic amount of a compound with an acid reaction, in an organic solvent medium, the characteristic feature being that the splitting medium is a mixture consisting of: A. at least one solvent chosen from the group of aprotic polar solvents formed by polymethylene-sulphones, alkylene glycol carbonates which contain 2 to 4 carbon atoms (in the alkylene portion) and aliphatic or aromatic nitriles, and B. at least one hydroxylic solvent taken from the group formed by aliphatic alcohols containing 1 to 3 carbon atoms and alkylene glycols containing up to 4 carbon atoms.
Inventors
- 👤 Michel Jouffret
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 19:03
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/08
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
228 words
In a process for the deperoxidization of a primary alkylaromatic hydroperoxide of the general formula: ##SPC2## in which: R represents an alkyl radical containing 1 to 4 carbon atoms and n represents an integer from 1 to 3, with the proviso that when n is equal to 1 the radical R, or when n is greater than 1 at least one of the radicals R, is in the ortho or para-position relative to the hydroperoxymethylene group, to form phenolic compounds which comprises reacting the hydroperoxide with 0.1 to 40% by weight of a compound possessing an acid reaction selected from the group consisting of inorganic and organic protonic acids, Friedel-Crafts catalysts, silica, and diatomaceous earth acid catalysts at a temperature from 20°C to 110°C in the presence of an inert organic solvent, the improvement wherein said solvent comprises: a. 40 to 98% by weight of at least one aprotic polar solvent selected from the group consisting (1) polymethylene-sulphones, (2) alkylene glycol carbonates which contain 2 to 4 carbon atoms in the alkylene portion and (3) acetonitrile, propionitrile and benzonitrile and b. 60 to 2% by weight of at least one hydroxylic solvent selected from the group consisting of alkanols containing 1 to 3 carbon atoms and alkylene glycols containing 2 to 4 carbon atoms, whereby the selectivity of the deperoxidization is increased with respect to the phenolic compounds.
Claim 2
Dependent Claim
228 words
In a process for the deperoxidization of a primary alkylaromatic hydroperoxide of the general formula: ##SPC2## in which: R represents an alkyl radical containing 1 to 4 carbon atoms and n represents an integer from 1 to 3, with the proviso that when n is equal to 1 the radical R, or when n is greater than 1 at least one of the radicals R, is in the ortho or para-position relative to the hydroperoxymethylene group, to form phenolic compounds which comprises reacting the hydroperoxide with 0.1 to 40% by weight of a compound possessing an acid reaction selected from the group consisting of inorganic and organic protonic acids, Friedel-Crafts catalysts, silica, and diatomaceous earth acid catalysts at a temperature from 20°C to 110°C in the presence of an inert organic solvent, the improvement wherein said solvent comprises: a. 40 to 98% by weight of at least one aprotic polar solvent selected from the group consisting (1) polymethylene-sulphones, (2) alkylene glycol carbonates which contain 2 to 4 carbon atoms in the alkylene portion and (3) acetonitrile, propionitrile and benzonitrile and b. 60 to 2% by weight of at least one hydroxylic solvent selected from the group consisting of alkanols containing 1 to 3 carbon atoms and alkylene glycols containing 2 to 4 carbon atoms, whereby the selectivity of the deperoxidization is increased with respect to the phenolic compounds.
Claim 3
Dependent Claim
12 words
Process according to claim 1, in which R is a methyl radical.
Claim 4
Dependent Claim
15 words
Process according to claim 2, in which the hydroperoxide is o-xylyl hydroperoxide or p-xylyl hydroperoxide.
Claim 5
Dependent Claim
35 words
Process according to claim 1 in which the polymethylene-sulphone contains 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.
Claim 6
Dependent Claim
24 words
Process according to claim 1 in which the aprotic polar solvent is selected from sulpholane, ethylene glycol carbonate, propylene glycol carbonate, acetonitrile and propionitrile.
Claim 7
Dependent Claim
21 words
Process according to claim 1 in which the hydroxylic compound is selected from methyl alcohol, ethyl alcohol, ethylene glycol and propane-1,2-diol.
Claim 8
Dependent Claim
13 words
Process according to claim 1 which is carried out at 50° to 110°C.
Claim 9
Dependent Claim
27 words
Process according to claim 1 in which the solvent medium contains 60 to 96% of the aprotic polar solvent and 40 to 4% of the hydroxylic solvent.
Claim 10
Dependent Claim
28 words
Process according to claim 1 in which the hydroxylic solvent is present in an amount such that at least one OH group is present per mol of hydroperoxide.
Claim 11
Dependent Claim
102 words
In a process for the deperoxidization of xylyl hydroperoxide to form cresols, which comprises reacting the hydroperoxide with 0.1 to 40% by weight of a protonic acid selected from hydrochloric acid, nitric acid, sulphuric acid, methanesulphonic acid, benzenesulphonic acid or para-toluenesulphonic acid in the presence of an inert organic solvent, the improvement wherein the deperoxidization is carried out at 50° - 110°C in the presence of a mixture of a) 40 to 98 percent by weight of sulpholane or acetonitrile and b) 60 to 2 percent by weight of methanol, whereby the selectivity of the deperoxidization is increased with respect to cresol.
Claim 12
Dependent Claim
102 words
In a process for the deperoxidization of xylyl hydroperoxide to form cresols, which comprises reacting the hydroperoxide with 0.1 to 40% by weight of a protonic acid selected from hydrochloric acid, nitric acid, sulphuric acid, methanesulphonic acid, benzenesulphonic acid or para-toluenesulphonic acid in the presence of an inert organic solvent, the improvement wherein the deperoxidization is carried out at 50° - 110°C in the presence of a mixture of a) 40 to 98 percent by weight of sulpholane or acetonitrile and b) 60 to 2 percent by weight of methanol, whereby the selectivity of the deperoxidization is increased with respect to cresol.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-31 | 1980-03-01 | 1980-08-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-31 | 1984-03-01 | 1984-08-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-31 | 1988-03-01 | 1988-08-31 | $7700.00 | Window Closed / Lapsed |