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US5155278A
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Process for the oxidation of alcohols to aldehydes
Assignee: Shell USA Inc
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Filing: 1991-09-30
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Granted: 1992-10-13
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Expires: 2011-09-30
Abstract
Abstract A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R 1 , R 2 , R 3 and R 4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R 5 and R 6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid and a non-basic polar solvent, in the presence of an oxidant, for about eight hours or less at a temperature in the range of from about -10° C. to about 25° C., and thereafter separating out the aldehyde.
Inventors
- 👤 Herbert E. Fried
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 16:53
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/27; C07C45/29
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
143 words
A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol having a carbon number in the range of from about 1 to about 45 with a solubilized stable free radical nitroxide having the formula: ##STR5## wherein each of R 1 , R 2 , R 3 and R 4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R 5 and R 6 is alky, hydrogen, aryl or a substituted heteroatom, nitric acid and an non-basic polar solvent selected from the group consisting of acetonitrile, sulfolane, tertiary butyl alcohol, tertiaryl amyl alcohol, and mixtures thereof, in the presence of an oxygen-containing gas, for about eight hours or less at a temperature in the range of from about -10° C. to about 25° C., and thereafter separating out the aldehyde.
Claim 2
Dependent Claim
143 words
A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol having a carbon number in the range of from about 1 to about 45 with a solubilized stable free radical nitroxide having the formula: ##STR5## wherein each of R 1 , R 2 , R 3 and R 4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R 5 and R 6 is alky, hydrogen, aryl or a substituted heteroatom, nitric acid and an non-basic polar solvent selected from the group consisting of acetonitrile, sulfolane, tertiary butyl alcohol, tertiaryl amyl alcohol, and mixtures thereof, in the presence of an oxygen-containing gas, for about eight hours or less at a temperature in the range of from about -10° C. to about 25° C., and thereafter separating out the aldehyde.
Claim 3
Dependent Claim
29 words
The process of claim 1 wherein the solubilized stable free radical nitroxide is selected from the group consisting of 2,2,6,6-tetramethyl-piperidine-1-oxyl, 4-hydroxy-2,2,6,6- tetramethyl-piperidine-1-oxyl, 4-oxo-2,2,6,6-tetramethyl-piperidine-1-oxyl, 2,2,6,6- tetramethyl-piperidine-1-oxyl-4-sulfate, 4-alkoxy-2,26,6-tetramethyl-piperidine-1-oxyl and mixtures thereof.
Claim 4
Dependent Claim
26 words
The process of claim 2 wherein the solubilized stable free radical nitroxide is selected from the group consisting of 2,2,6,6- tetramethyl-piperidine-1-oxyl, 2,2,6,6-tetramethyl-piperidine-1-oxyl-4-sulfate, 4-alkoxy-2,2,6,6-tetramethyl-piperidine-1-oxyl and mixtures thereof.
Claim 5
Dependent Claim
10 words
The process of claim 1 wherein said solvent is acetonitrile.
Claim 6
Dependent Claim
25 words
The process of claim 1 wherein said is nitric acid has a concentration in the range of from about 50 percent to about 100 percent.
Claim 7
Dependent Claim
16 words
The process of claim 5 wherein said nitric acid has a concentration of about 70 percent.
Claim 8
Dependent Claim
28 words
The process of claim 1 wherein said the amount of nitric acid utilized is in the range of from about 5 mole percent to about 100 mole percent.
Claim 9
Dependent Claim
29 words
The process of claim 1 wherein said alkanol is contacted with said solubilized stable free radical nitroxide, followed by the addition thereto of said nitric acid and said oxidant.
Claim 10
Dependent Claim
37 words
The process of claim 8 wherein the amount of solubilized stable free radical nitroxide is in the range of from about 1 mole percent to about 50 mole percent, basis the number of moles of said alkanol.
Claim 11
Dependent Claim
36 words
The process of claim 8 wherein the amount of solubilized stable free radical nitroxide is in the range of from 5 mole percent to about 20 mole percent, basis the number of moles of said alkanol.
Claim 12
Dependent Claim
28 words
The process of claim 8 wherein said the amount of nitric acid utilized is in the range of from about 5 mole percent to about 100 mole percent.
Claim 13
Dependent Claim
18 words
The process of claim 1 wherein said oxygen-containing gas is selected from pure oxygen and oxygen in air.
Claim 14
Dependent Claim
12 words
The process of claim 12 wherein said oxygen-containing gas is pure oxygen.
Claim 15
Dependent Claim
30 words
The process of claim 1 wherein said process is carried out at a temperature in the range of from about 10° C. to about 20° C. and at atmospheric pressure.
References Cited (Backward Citations)
US4620033A
Cited
JPH0596516A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1995-10-13 | 1996-04-13 | 1996-10-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-10-13 | 2000-04-13 | 2000-10-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-10-13 | 2004-04-13 | 2004-10-13 | $7700.00 | Window Closed / Lapsed |