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US4207264A Expired / Lapsed US ⏱️ 0.0 years remaining

Rearrangement of aralkyl hydroperoxides to form phenols and carbonyl compounds

Assignee: Goodyear Tire and Rubber Co
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Filing: 1973-03-27
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Granted: 1980-06-10
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Expires: 1993-03-27
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Abstract

Abstract A continuous process for cleaving aralkyl hydroperoxides in acid media to yield phenols and carbonyl compounds in a reactor arranged and operated to limit the total residence time to less than the time required to form discoloration products.

Inventors

  • 👤 John E. Anderson
  • 👤 Ernest G. Hildenbrand

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 15:29
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/08; C07C45/00; C07C45/51; C07C45/53

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 213 words
A continuous process for catalytically cleaving an aralkyl hydroperoxide of the general formula ##STR3## where Ar is an unsubstituted benzene nucleus, alkyl benzene nucleus or polynuclear aromatic, R and R' are alkyl, cycloalkyl or hydrogen, and n is a whole number from one to three inclusive, to form the corresponding phenolic and carbonyl compounds, comprising the steps of: (a) forming a reaction mixture by continuously combining said hydroperoxide in the presence of a substantially non-reactive material selected from the group consisting of an organic solvent and liquid carrier with an acid cleavage catalyst in an amount of at least about 0.10% of said reaction mixture, said catalyst being selected from the class consisting of mineral acids and Lewis acids, (b) flowing said reaction mixture through a reaction zone characterized by the lack of substantial backmixing at a temperature of about 50° C.-120° C. for a residence time sufficient to complete cleavage of said hydroperoxide to its corresponding phenolic compound, the hold back in said reaction zone being limited to a value less than 1/3, where e is the natural function 2.718 to control the formation of highly colored side products, and (c) continuously recovering from said reaction zone a reaction effluent containing said cleavage products and substantially devoid of highly colored side products.
Claim 2
Dependent Claim 213 words
A continuous process for catalytically cleaving an aralkyl hydroperoxide of the general formula ##STR3## where Ar is an unsubstituted benzene nucleus, alkyl benzene nucleus or polynuclear aromatic, R and R' are alkyl, cycloalkyl or hydrogen, and n is a whole number from one to three inclusive, to form the corresponding phenolic and carbonyl compounds, comprising the steps of: (a) forming a reaction mixture by continuously combining said hydroperoxide in the presence of a substantially non-reactive material selected from the group consisting of an organic solvent and liquid carrier with an acid cleavage catalyst in an amount of at least about 0.10% of said reaction mixture, said catalyst being selected from the class consisting of mineral acids and Lewis acids, (b) flowing said reaction mixture through a reaction zone characterized by the lack of substantial backmixing at a temperature of about 50° C.-120° C. for a residence time sufficient to complete cleavage of said hydroperoxide to its corresponding phenolic compound, the hold back in said reaction zone being limited to a value less than 1/3, where e is the natural function 2.718 to control the formation of highly colored side products, and (c) continuously recovering from said reaction zone a reaction effluent containing said cleavage products and substantially devoid of highly colored side products.
Claim 3
Dependent Claim 15 words
A process of claim 1 wherein said reaction is performed in an elongated tubular reactor.
Claim 4
Dependent Claim 36 words
The process of claim 2 wherein said reactor has a volume cpacity such that the flow rate of said hydroperoxide and catalyst there through has a reaction residence time of about 5 to about 12 minutes.
Claim 5
Dependent Claim 19 words
A process of claim 1 wherein the ratio of said solvent to said hydroperoxide is about 3:1 to 20:1.
Claim 6
Dependent Claim 24 words
The process of claim 1 wherein said rearrangement catalyst is present in an amount of about 0.10 to 5.0% of the said reaction mixture.
Claim 7
Dependent Claim 23 words
The process of claim 1 wherein said rearrangement catalyst is present in an amount of about 0.10 to 1.0% of said reaction mixture.
Claim 8
Dependent Claim 19 words
The process of claim 1 wherein the hold back valve of the reaction mixture is about 1/4 or less.
Claim 9
Dependent Claim 17 words
The process of claim 1 wherein said organic solvent comprises the carbonyl product of the cleavage reaction.

References Cited (Backward Citations)

US2842597A Cited
US3271457A Cited
FR522886A Cited
US3497561A Cited
GB1202687A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-06-10 1983-12-10 1984-06-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-06-10 1987-12-10 1988-06-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-06-10 1991-12-10 1992-06-10 $7700.00 Window Closed / Lapsed

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