US3897319A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Recovery and recycle process for anodic oxidation of benzene to quinone
Assignee: Carus LLC
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Filing: 1973-08-06
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Granted: 1975-07-29
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Expires: 1993-08-06
Abstract
Abstract In a combination recovery and recycle process for the anodic oxidation of benzene to quinone in electrolysis cells, recycle benzene of low quinone content is provided by contacting the cell-converted benzene with a water solution of hydroquinone, the quinone extracting into the water solution and forming precipitated quinhydrone, which is recovered therefrom. The spent hydroquinone water solution is separated from the residual benzene, which is recycled to the electrolysis system. This combination process favors efficient conversion of benzene to quinone by keeping the quinone content of the benzene supplied to the electrolysis cells at a low value, and the recycling of soluble impurities in the benzene improves the purity of the quinhydrone. The product is readily convertible into quinone or hydroquinone, or it may be stored until such conversion is desired.
Inventors
- 👤 Fred J Anderson
- 👤 Jack L Kessler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 16:54
CPC Classifications
C; C25; C25B; C25B3/00; C25B3/20; C25B3/23; C25B3/01; C25B3/07
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
165 words
A SEPARATION AND RECYCLE PROCESS FOR USE WITH ELECTROLYSIS APPARATUS CONVERTING BENZENE TO QUINONE IN ANODE COMPARTMENT THEREOF, SAID APPARATUS CONTINUOUSLY PRODUCING A DILUTE SOLUTION OF QUIONE IN BENZENE CONTAINING SUBSTANTIALLY IN EXCESS OF 1 GRAM QUINONE PER LITER, COMPRISING INTERMIXING AND CONTACTING PORTIONS OF SAID PRODUCT SOLUTION WITH A WATER SOLUTION OF HYDROQUINONE CONTAINING AT LEAST 15 GRAMS PER LITER OF HYDROQUINONE, SAID CONTACTING BEING CARRIED OUT WITH SAID SOLUTIONS AT TEMPERATURES OF FROM 10 TO 25*C., SAID CONTACTING REMOVING DISSOLVED QUINONE FROM SAID PRODUCT SOLUTION BY REACTION WITH SAID HYDROQUINONE TO FORM QUINHYDRONE PERCIPITATE, SAID CONTACTING BEING CONTINUED WITH FORMATION OF SAID QUINHYDRONE UNTIL THE RESULTING BENZENE CONTAINS LESS THAN ONE GRAM PER LITER OF DISSOLVED QUINONE, SEPARATING SAID RESULTING BENZENE FROM THE REMAINING HYDROQUINONE WATER SOLUTION AND SAID QUINHYDRONE PERCIPITATE, AND RECYCLING SAID SEPARATED BENZENE TO SAID ELECTROLYSIS APPARATUS, WHEREBY RECYCLED BENZENE IS SUPPLIED TO SAID APPARATUS OF SUFFICIENTLY LOW QUINONE CONTENT TOMAINTAIN A MORE EFFICIENT ANODIC OXIDATION OF BENZENE TO QUINONE.
Claim 2
Dependent Claim
165 words
A SEPARATION AND RECYCLE PROCESS FOR USE WITH ELECTROLYSIS APPARATUS CONVERTING BENZENE TO QUINONE IN ANODE COMPARTMENT THEREOF, SAID APPARATUS CONTINUOUSLY PRODUCING A DILUTE SOLUTION OF QUIONE IN BENZENE CONTAINING SUBSTANTIALLY IN EXCESS OF 1 GRAM QUINONE PER LITER, COMPRISING INTERMIXING AND CONTACTING PORTIONS OF SAID PRODUCT SOLUTION WITH A WATER SOLUTION OF HYDROQUINONE CONTAINING AT LEAST 15 GRAMS PER LITER OF HYDROQUINONE, SAID CONTACTING BEING CARRIED OUT WITH SAID SOLUTIONS AT TEMPERATURES OF FROM 10 TO 25*C., SAID CONTACTING REMOVING DISSOLVED QUINONE FROM SAID PRODUCT SOLUTION BY REACTION WITH SAID HYDROQUINONE TO FORM QUINHYDRONE PERCIPITATE, SAID CONTACTING BEING CONTINUED WITH FORMATION OF SAID QUINHYDRONE UNTIL THE RESULTING BENZENE CONTAINS LESS THAN ONE GRAM PER LITER OF DISSOLVED QUINONE, SEPARATING SAID RESULTING BENZENE FROM THE REMAINING HYDROQUINONE WATER SOLUTION AND SAID QUINHYDRONE PERCIPITATE, AND RECYCLING SAID SEPARATED BENZENE TO SAID ELECTROLYSIS APPARATUS, WHEREBY RECYCLED BENZENE IS SUPPLIED TO SAID APPARATUS OF SUFFICIENTLY LOW QUINONE CONTENT TOMAINTAIN A MORE EFFICIENT ANODIC OXIDATION OF BENZENE TO QUINONE.
Claim 3
Dependent Claim
23 words
The process of claim 1 in which the concentration of dissolved quinone in said product solution is not over 5 grams per liter.
Claim 4
Dependent Claim
25 words
The process of claim 1 in which said water solution of hydroquinone when first contacted with said product solution is substantially saturated with said hydroquinone.
Claim 5
Dependent Claim
36 words
The process of claim 3 in which said contacting is carried out at a temperature from 2* to 5*C. below the ambient atmospheric temperature to avoid precipitation of hydroquinone from said substantially saturated water solution thereof.
Claim 6
Dependent Claim
170 words
A separation and recycle process for use with electrolysis apparatus converting benzene to quinone in anode compartments thereof, said apparatus continuously producing a dilute solution of quinone in benzene containing dissolved quinone within the range from 1 to 5 grams per liter, comprising intermixing and contacting portions of said product solution with a water solution of hydroquinone containing at least 15 grams per liter of hydroquinone, said contacting being carried out with said solutions at temperatures of substantially 15 to 20*C., said contacting removing dissolved quinone from said product solution by reaction with said hydroquinone to form quinhydrone precipitate, said contacting being continued with formation of said quinhydrone until the resulting benzene contains from 0.3 to 0.9 grams per liter of dissolved quinone, separating said resulting benzene from the remaining hydroquinone water solution and said quinhydrone precipitate, and recycling said separated benzene to said electrolysis apparatus, whereby recycLed benzene is supplied to said apparatus of sufficiently low quinone content to maintain a more efficient anodic oxidation of benzene to quinone.
Claim 7
Dependent Claim
170 words
A separation and recycle process for use with electrolysis apparatus converting benzene to quinone in anode compartments thereof, said apparatus continuously producing a dilute solution of quinone in benzene containing dissolved quinone within the range from 1 to 5 grams per liter, comprising intermixing and contacting portions of said product solution with a water solution of hydroquinone containing at least 15 grams per liter of hydroquinone, said contacting being carried out with said solutions at temperatures of substantially 15 to 20*C., said contacting removing dissolved quinone from said product solution by reaction with said hydroquinone to form quinhydrone precipitate, said contacting being continued with formation of said quinhydrone until the resulting benzene contains from 0.3 to 0.9 grams per liter of dissolved quinone, separating said resulting benzene from the remaining hydroquinone water solution and said quinhydrone precipitate, and recycling said separated benzene to said electrolysis apparatus, whereby recycLed benzene is supplied to said apparatus of sufficiently low quinone content to maintain a more efficient anodic oxidation of benzene to quinone.
Claim 8
Dependent Claim
56 words
The process of claim 5 in which said product solution contains from 3 to 5 grams per liter of dissolved quinone, said contacting is carried out at a temperature of about 17* to 19*C., and said water solution of hydroquinone when initially contacted with said portions of said product solution is substantially saturated with said hydroquinone.
Claim 9
Dependent Claim
36 words
The process of claim 6 in which said contacting is carried out at a temperature from 2* to 5*C. below the ambient atmospheric temperature to avoid precipitation of hydroquinone from said substantially saturated water solution thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-07-28 | 1979-01-27 | 1979-07-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-07-28 | 1983-01-27 | 1983-07-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-07-28 | 1987-01-27 | 1987-07-29 | $7700.00 | Window Closed / Lapsed |