US5155280A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the oxidation of alcohols to aldehydes
Assignee: Shell USA Inc
•
Filing: 1991-09-30
•
Granted: 1992-10-13
•
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: <IMAGE> wherein each of R1, R2, R3 and R4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R5 and R6 is alkyl, hydrogen, aryl or a substituted heteroatom, an alkali metal nitrosodisulfonate, a non-basic polar solvent and an oxidant, for about eight hours or less at a temperature in the range of from about 10 DEG C. to about 20 DEG C. and thereafter separating out the aldehyde.
Inventors
- 👤 Herbert E. Fried
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 17:24
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/27; C07C45/29
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
149 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 alkyl, hydrogen, aryl or a substituted heteroatom, an alkali metal nitrosodisulfonate selected from the group consisting of potassium nitrosodisulfonate, sodium nitrosodisulfate and mixtures thereof, a non-basic polar solvent selected from the group consisting of acetonitrile, dimethylsulfolane, nitroethane and mixtures thereof, and an oxygen-containing gas, for about eight hours or less at a temperature in the range of from about 10° C. to about 20° C. and thereafter separating out the aldehyde.
Claim 2
Dependent Claim
149 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 alkyl, hydrogen, aryl or a substituted heteroatom, an alkali metal nitrosodisulfonate selected from the group consisting of potassium nitrosodisulfonate, sodium nitrosodisulfate and mixtures thereof, a non-basic polar solvent selected from the group consisting of acetonitrile, dimethylsulfolane, nitroethane and mixtures thereof, and an oxygen-containing gas, for about eight hours or less at a temperature in the range of from about 10° C. to about 20° C. and thereafter separating out the aldehyde.
Claim 3
Dependent Claim
27 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-2,2,6,6-tetramethyl-piperidine-1-oxyl and mixtures thereof.
Claim 4
Dependent Claim
25 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
12 words
The process of claim 1 wherein said non-basic polar solvent is acetonitrile.
Claim 6
Dependent Claim
13 words
The process of claim 1 wherein said alkali metal nitrosodisulfonate is potassium nitrosodisulfonate.
Claim 7
Dependent Claim
30 words
The process of claim 1 wherein said alkanol is contacted with said solubilized stable free radical nitroxide and said alkali metal nitrosodisulfonate, followed by the addition thereto of said oxidant.
Claim 8
Dependent Claim
35 words
The process of claim 6 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 weight of the alkanol.
Claim 9
Dependent Claim
35 words
The process of claim 7 wherein the amount of said alkalimetal nitrosodisulfonate is in the range of from about 1 mole percent to about 35 mole percent, basis the number of moles of said alkanol.
Claim 10
Dependent Claim
26 words
The process of claim 1 wherein said alkanol is contacted with said alkali metal nitrosodisulfonate, followed by the addition thereto of said stable free radical nitroxide.
Claim 11
Dependent Claim
37 words
The process of claim 9 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 12
Dependent Claim
35 words
The process of claim 10 wherein the amount of said alkalimetal nitrosodisulfonate is in the range of from about 1 mole percent to about 35 mole percent, basis the number of moles of said alkanol.
Claim 13
Dependent Claim
20 words
The process of claim 1 wherein said oxygen-containing gas is selected from the group consisting of pure oxygen and 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 0° C. to about 20° C. and at atmospheric pressure.
Claim 16
Dependent Claim
30 words
The process of claim 14 wherein said process is carried out at a temperature in the range of from about 10° C. to about 15° 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 |
|---|---|---|---|---|---|
| 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 |