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US4051187A Expired / Lapsed US ⏱️ 0.0 years remaining

Method of producing aminophenol using a rhodium/carbon catalyst with synergistic quantities of rhodium, trichloride or rhodium tribromide

Assignee: Oxamine Inc
•
Filing: 1976-04-26
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Granted: 1977-09-27
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Expires: 1996-04-26
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Abstract

Abstract A semicontinuous or continuous process for producing para-aminophenols by the hydrogenation of corresponding nitrobenzenes wherein a catalyst containing about 5% platinum-group metal wherein about 10 to 80% of said platinum-group metal is in the form of RhCl 3 and from 20 to 90% of said platinum-group metal is in the form of elemental Rh, Pd, Pt, or Ru and where the balance of said catalyst comprises carbon to convert substantially all of the nitrobenzene to a para-aminophenol in an aqueous phase containing the latter.

Inventors

  • 👤 Eugene Medcalf

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 11:39
CPC Classifications
C; C07; C07C; C07C215/00; C07C215/74; C07C215/76

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 223 words
A method of preparing aminophenol comprising the steps of: a. hydrogenating a nitrobenzene substantially to completion by feeding hydrogen to a reaction mixture containing the nitrobenzene in the presence of aqueous sulfuric acid and a hydrogenation catalyst which comprises platinum group metal wherein from 10 to 80% of said platinum group metal is in the form of a rhodium salt selected from the group which consists of RhCl 3 and RhBr 3 and from 20 to 90% of said platinum group metal is in the form of elemental Rh, Pt, Pd or Ru and wherein the balance of said catalyst comprises carbon to produce a para-aminophenol in an aqueous phase containing the latter at a temperature of from 80 to 110° C and at 1 to 3 atmospheres; b. terminating hydrogen feed to said reaction mixture: c. thereafter charging the reaction mixture with a quantity of fresh nitrobenzene as required to repeat step (a); d. thereafter premitting said aqueous phase to separate from the nitrobenzene phase; e. next removing said aqueous phase from said reactor while retaining said nitrobenzene phase and said catalyst therein; f. thereafter adding fresh sulfuric acid to the reactor; g. repeating steps (a) through (f) in succession to transform nitrobenzene semicontinuously into said para-aminophenol; and h. recovering the para-aminophenol thus formed from the aqueous phases removed from said reactor.
Claim 2
Independent Claim 223 words
A method of preparing aminophenol comprising the steps of: a. hydrogenating a nitrobenzene substantially to completion by feeding hydrogen to a reaction mixture containing the nitrobenzene in the presence of aqueous sulfuric acid and a hydrogenation catalyst which comprises platinum group metal wherein from 10 to 80% of said platinum group metal is in the form of a rhodium salt selected from the group which consists of RhCl 3 and RhBr 3 and from 20 to 90% of said platinum group metal is in the form of elemental Rh, Pt, Pd or Ru and wherein the balance of said catalyst comprises carbon to produce a para-aminophenol in an aqueous phase containing the latter at a temperature of from 80 to 110° C and at 1 to 3 atmospheres; b. terminating hydrogen feed to said reaction mixture: c. thereafter charging the reaction mixture with a quantity of fresh nitrobenzene as required to repeat step (a); d. thereafter premitting said aqueous phase to separate from the nitrobenzene phase; e. next removing said aqueous phase from said reactor while retaining said nitrobenzene phase and said catalyst therein; f. thereafter adding fresh sulfuric acid to the reactor; g. repeating steps (a) through (f) in succession to transform nitrobenzene semicontinuously into said para-aminophenol; and h. recovering the para-aminophenol thus formed from the aqueous phases removed from said reactor.
Claim 3
Dependent Claim 37 words
The method defined in claim 1 wherein the 5% platinum group metal in the catalyst is comprised of about 39% Rh in the form of RhCl 3 and about 61% Rh in the form of elemental Rh.
Claim 4
Dependent Claim 34 words
The method defined in claim 1 wherein the rate of absorption of hydrogen is from 1.8 to 2.2 moles of H 2 /mole of nitrobenzene over a period of from 4 to 12 hours.
Claim 5
Dependent Claim 33 words
The method defined in claim 1 wherein during step (b) the fresh nitrobenzene introduced into the reaction mixture is equal to from 10 to 30% of the nitrobenzene required for the next reaction.

References Cited (Backward Citations)

US2823235A Cited
GB1009024A Cited
GB1028078A Cited
US3383416A Cited
US3694508A Cited
US3678108A Cited
US3754014A Cited
US3876703A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-09-26 1981-03-28 1981-09-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-09-26 1985-03-28 1985-09-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-09-26 1989-03-28 1989-09-27 $7700.00 Window Closed / Lapsed

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