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US4584070A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing para-aminophenol

Assignee: PPG Industries Inc
•
Filing: 1985-03-29
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Granted: 1986-04-22
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Expires: 2005-03-29
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Abstract

Abstract Disclosed is a method of preparing para-aminophenol by the electrolytic reduction of nitrobenzene in an acidic, aqueous reaction medium including a trialkylamine-N-oxide surfactant, such as dimethyldodecylamine-N-oxide, by electrolytic reduction at a cathode comprised of an amalgamated metal, and by electrolytic reduction under essentially anerobic or oxygen-free conditions in the catholyte.

Inventors

  • 👤 Norman R. DeLue
  • 👤 Stanley R. Pickens

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 03:18
CPC Classifications
C; C25; C25B; C25B3/00; C25B3/20; C25B3/25; C25B3/01; C25B3/07; C25B3/09

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 41 words
In the method of preparing para-aminophenol by electrolytic reduction of nitrobenzene in an acidic, aqueous reaction medium, the improvement which comprises emulsifying the nitrobenzene reactant in the acidic, aqueous reaction medium with a trialkylamine-N-oxide surfactant and electrolyzing said emulsified reaction medium.
Claim 2
Dependent Claim 41 words
In the method of preparing para-aminophenol by electrolytic reduction of nitrobenzene in an acidic, aqueous reaction medium, the improvement which comprises emulsifying the nitrobenzene reactant in the acidic, aqueous reaction medium with a trialkylamine-N-oxide surfactant and electrolyzing said emulsified reaction medium.
Claim 3
Dependent Claim 11 words
The method of claim 1 wherein the surfactant is a dimethylalkylamine-N-oxide.
Claim 4
Dependent Claim 10 words
The method of claim 2 wherein the surfactant is dimethyldodecylamine-N-oxide.
Claim 5
Dependent Claim 15 words
The method of claim 1 wherein the electrolytic reduction is conducted under essentially oxygen-free conditions.
Claim 6
Dependent Claim 15 words
The method of claim 3 wherein the electrolytic reduction is conducted under essentially oxygen-free conditions.
Claim 7
Dependent Claim 73 words
In the method of preparing para-aminophenol by electrolytic reduction of nitrobenzene in an acidic, aqueous reaction medium, the improvement which comprises emulsifying the nitrobenzene reactant in the acidic, aqueous reaction medium with a trialkylamine-N-oxide surfactant and electrolyzing said emulsified reaction medium in an electrolytic cell having an anolyte compartment with an anode therein, a catholyte compartment with a cathode therein and a cation exchange membrane separating the anolyte compartment and the catholyte compartment.
Claim 8
Dependent Claim 73 words
In the method of preparing para-aminophenol by electrolytic reduction of nitrobenzene in an acidic, aqueous reaction medium, the improvement which comprises emulsifying the nitrobenzene reactant in the acidic, aqueous reaction medium with a trialkylamine-N-oxide surfactant and electrolyzing said emulsified reaction medium in an electrolytic cell having an anolyte compartment with an anode therein, a catholyte compartment with a cathode therein and a cation exchange membrane separating the anolyte compartment and the catholyte compartment.
Claim 9
Dependent Claim 14 words
The method of claim 6 wherein the cathode is comprised of an amalgamated metal.
Claim 10
Dependent Claim 11 words
The method of claim 7 wherein the surfactant is a dimethylalkylamine-N-oxide.
Claim 11
Dependent Claim 10 words
The method of claim 8 wherein the surfactant is dimethyldodecylamine-N-oxide.
Claim 12
Dependent Claim 19 words
The method of claim 6 wherein the catholyte compartment is maintained under essentially oxygen-free conditions during the electrolytic reduction.
Claim 13
Dependent Claim 19 words
The method of claim 9 wherein the catholyte compartment is maintained under essentially oxygen-free conditions during the electrolytic reduction.
Claim 14
Dependent Claim 29 words
The method of claim 8 wherein the cathode comprises an amalgamated metal selected from the group consisting of amalgamated copper, amalgamated nickel, amalgamated zinc, and an amalgamated nickel-copper alloy.
Claim 15
Dependent Claim 29 words
The method of claim 11 wherein the cathode comprises an amalgamated metal selected from the group consisting of amalgamated copper, amalgamated nickel, amalgamated zinc, and an amalgamated nickel-copper alloy.
Claim 16
Dependent Claim 11 words
The method of claim 9 wherein the cathode is amalgamated copper.
Claim 17
Dependent Claim 19 words
The method of claim 14 wherein the catholyte compartment is maintained under essentially oxygen-free conditions during the electrolytic reduction.
Claim 18
Dependent Claim 39 words
The method of claim 15 wherein the electrolytic cell further includes a third compartment between said anolyte compartment and said catholyte compartment, said third compartment separated from each of said anolyte and catholyte compartments by a cation exchange membrane.
Claim 19
Dependent Claim 143 words
In the method of preparing para-aminophenol by electrolytic reduction of nitrobenzene in an acidic, aqueous reaction medium, the improvement which comprises emulsifying the acidic, aqueous reaction medium by addition of about 0.12 percent by weight dimethyldodecylamine-N-oxide as a surfactant, said reaction medium including from about 5 to 20 percent by weight of the nitrobenzene reactant on the basis of total weight of reaction medium, and the balance water and about 2 M sulfuric acid within said medium, and electrolyzing said emulsified reaction medium at a temperature of about 80° to 100° C. and a current density of about 15 to 25 A/dm 2 in an electrolytic cell having an anolyte compartment with an anode and anolyte therein, a catholyte compartment with an amalgamated copper cathode and the reaction medium therein and a cation exchange membrane separating the anolyte compartment and the catholyte compartment.
Claim 20
Dependent Claim 143 words
In the method of preparing para-aminophenol by electrolytic reduction of nitrobenzene in an acidic, aqueous reaction medium, the improvement which comprises emulsifying the acidic, aqueous reaction medium by addition of about 0.12 percent by weight dimethyldodecylamine-N-oxide as a surfactant, said reaction medium including from about 5 to 20 percent by weight of the nitrobenzene reactant on the basis of total weight of reaction medium, and the balance water and about 2 M sulfuric acid within said medium, and electrolyzing said emulsified reaction medium at a temperature of about 80° to 100° C. and a current density of about 15 to 25 A/dm 2 in an electrolytic cell having an anolyte compartment with an anode and anolyte therein, a catholyte compartment with an amalgamated copper cathode and the reaction medium therein and a cation exchange membrane separating the anolyte compartment and the catholyte compartment.
Claim 21
Dependent Claim 39 words
The method of claim 17 wherein the electrolytic cell further includes a third compartment between said anolyte compartment and said catholyte compartment, said third compartment separated from each of said anolyte and catholyte compartments by a cation exchange membrane.
Claim 22
Dependent Claim 19 words
The method of claim 17 wherein the catholyte compartment is maintained under essentially oxygen-free conditions during the electrolytic reduction.
Claim 23
Dependent Claim 19 words
The method of claim 18 wherein the catholyte compartment is maintained under essentially oxygen-free conditions during the electrolytic reduction.

References Cited (Backward Citations)

US3338806A Cited
US3475299A Cited
US3645864A Cited
US4396474A Cited
US4264529A Cited
US4307249A Cited
US4415753A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-04-21 1989-10-21 1990-04-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-04-21 1993-10-21 1994-04-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-04-21 1997-10-21 1998-04-22 $7700.00 Window Closed / Lapsed

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