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US3972951A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the formation of 2,6-diphenyl-phenol

Assignee: General Electric Co
•
Filing: 1971-03-08
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Granted: 1976-08-03
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Expires: 1991-03-08
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Abstract

Abstract A process for the formation of 2,6-diphenylphenol involving the autocondensation of cyclohexanone with itself to form a mixture of cyclic ketones containing a tricyclic ketone fraction and the dehydrogenation of the tricyclic ketone fraction to form 2,6-diphenylphenol. The process is characterized by reaction conditions permitting the formation of 2,6-diphenylphenol on a commercial scale that is free of impurities and suitable for many new applications requiring high purity as synthesis of drugs, plastics and the like.

Inventors

  • 👤 Robert S. Kapner
  • 👤 Donald L. Kippax
  • 👤 Kevin E. Murphy
  • 👤 Lalitkumar H. Udani

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 16:36
CPC Classifications
C; C07; C07C; C07C49/00; C07C49/587; C07C49/613; C07C37/00; C07C37/06; C07C37/07; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/72; C07C45/74; C07C49/647; C07C49/653

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 294 words
In a process for the preparation of 2,6-diphenylphenol, the steps comprising: a. passing a reaction mixture consisting of an aqueous alkaline catalyst and a cyclic ketone selected from the group consisting of cyclohexanone and mixtures thereof with bicyclic condensation products of cyclohexanone successively through at least two condensation reactors in a condensation reactor zone wherein the reaction temperature is from 150° to 200° C.; b. removing said condensation product from said reactor zone when it contains a maximum of 70% of tricyclic ketones by weight; c. collecting and condensing the vapors above the condensation reactors in the reactor zone and passing the same to a decantor wherein a water phase and a cyclohexanone phase is formed; d. separating said cyclohexanone phase from the water phase and recycling said cyclohexanone phase to the first condensation reactor in said reaction zone whereby it acts as a source of cyclohexanone and as a solvent for the reaction mixture; e. cooling said condensation product as it leaves said reaction zone; f. passing said condensation product to a neutralizer and neutralizing by adding an acid to form an aqueous phase and an organic phase; g. separating said organic phase from said aqueous phase; h. passing said organic phase through a first distillation column to remove water, a second distillation column to remove bicyclic autocondensation products of cyclohexanone which are recycled to the first condensation reactor, and a third distillation column to separate an isomeric mixture of tricyclic ketones from the remainder of the organic phase; i. passing said isomeric mixture of tricyclic ketones through a dehydrogenation catalyst in a fixed bed dehydrogenation reactor maintained at a temperature from 240° to 360° C. to produce a mixture of 2,6-diphenylphenol and partially dehydrogenated by-products; and j. recovering 2,6-diphenylphenol from said mixture.
Claim 2
Dependent Claim 294 words
In a process for the preparation of 2,6-diphenylphenol, the steps comprising: a. passing a reaction mixture consisting of an aqueous alkaline catalyst and a cyclic ketone selected from the group consisting of cyclohexanone and mixtures thereof with bicyclic condensation products of cyclohexanone successively through at least two condensation reactors in a condensation reactor zone wherein the reaction temperature is from 150° to 200° C.; b. removing said condensation product from said reactor zone when it contains a maximum of 70% of tricyclic ketones by weight; c. collecting and condensing the vapors above the condensation reactors in the reactor zone and passing the same to a decantor wherein a water phase and a cyclohexanone phase is formed; d. separating said cyclohexanone phase from the water phase and recycling said cyclohexanone phase to the first condensation reactor in said reaction zone whereby it acts as a source of cyclohexanone and as a solvent for the reaction mixture; e. cooling said condensation product as it leaves said reaction zone; f. passing said condensation product to a neutralizer and neutralizing by adding an acid to form an aqueous phase and an organic phase; g. separating said organic phase from said aqueous phase; h. passing said organic phase through a first distillation column to remove water, a second distillation column to remove bicyclic autocondensation products of cyclohexanone which are recycled to the first condensation reactor, and a third distillation column to separate an isomeric mixture of tricyclic ketones from the remainder of the organic phase; i. passing said isomeric mixture of tricyclic ketones through a dehydrogenation catalyst in a fixed bed dehydrogenation reactor maintained at a temperature from 240° to 360° C. to produce a mixture of 2,6-diphenylphenol and partially dehydrogenated by-products; and j. recovering 2,6-diphenylphenol from said mixture.
Claim 3
Dependent Claim 34 words
A process as defined in claim 1 wherein, in step (b), said condensation product is removed from said reaction zone when the content of tricyclic ketone therein is from 30 to 45% by weight.
Claim 4
Dependent Claim 38 words
A process as defined in claim 1 wherein the condensation temperature is from 170° to 190° C.; the dehydrogenation temperature is from 300° to 350° C.; and the dehydrogenation catalyst is platinum or palladium deposited on a substrate.
Claim 5
Dependent Claim 14 words
A process as defined in claim 1 wherein said alkaline catalyst is sodium hydroxide.
Claim 6
Dependent Claim 18 words
A process as defined in claim 1 wherein said dehydrogenation catalyst is platinum deposited on an alumina substrate.
Claim 7
Dependent Claim 19 words
A process as defined in claim 1 wherein two condensation reactors in series are used in the reactor zone.

References Cited (Backward Citations)

No citation records indexed.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-08-03 1980-02-02 1980-08-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-08-03 1984-02-02 1984-08-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-08-03 1988-02-02 1988-08-03 $7700.00 Window Closed / Lapsed

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