US3681465A
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US
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Process of producing aldehydes using a catalyst including a group viii metal and phosphorus
Assignee: Ruhrchemie AG
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Filing: 1968-11-01
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Granted: 1972-08-01
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Expires: 1988-11-01
Abstract
Abstract In the production of aldehydes by reaction of carbon monoxide, hydrogen, and olefinically unsaturated compounds, utilizing a catalyst based on a Group VIII metal, e.g. cobalt, which catalyst includes as an additive, a phosphorus compound, the performance of the catalyst is improved, particularly in that high yields are obtained without the increase of reaction time commonly occasioned by use of a phosphorus compound, by using a phosphorus compound of the formula, for example: WHEREIN R1, R2, R3, R4, R5 and R6 are the same or different nonsubstituted or substituted aliphatic, cycloaliphatic, heterocyclic or aromatic radicals, A1 and A2 represent similar or different bridge atoms selected from the group comprising oxygen, sulfur, nitrogen and phosphorus and n is an integer having a value of 0 or 1 and even 2 if the bridge atom is sulfur, nitrogen or phosphorus.
Inventors
- 👤 Jurgen Falbe
- 👤 Hans Tummes
- 👤 Jurgen Weber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 17:42
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07C; C07C45/00; C07C45/49; C07C45/50; C07F9/535; C07F9/5352
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
29 words
Process according to claim 1, wherein R7 is in the para position and is hydrogen, chloro, alkyl, or dialkylamino and the malonic acid diester is a di-lower alkyl ester.
Claim 2
Dependent Claim
9 words
Process according to claim 2, wherein n is 0.
Claim 3
Dependent Claim
61 words
In a process of producing aldehydes by reaction of olefin with carbon monoxide and hydrogen at elevated temperature and elevated pressure in presence of a Group VIII metal selected from the group consisting of cobalt, rhodium and ruthenium as catalyst for the reaction, the improvement which comprises employing said catalyst in combination with derivatives of the compound 1,2-diphosphacyclopenten-(5)-one-(4) of the formula:
Claim 4
Dependent Claim
13 words
Process according to claim 4, in which said compound is of the formulas:
Claim 5
Dependent Claim
13 words
Process according to claim 4, in which said compound is of the formula:
Claim 6
Dependent Claim
11 words
Process according to claim 1, wherein said compound is 1-ethoxy-1,2-diphenyl-(1,2-diphosphacyclopenten-(5)-one-(4))-tricarboxylic acid-(3,3,5)-triethylester.
Claim 7
Dependent Claim
12 words
Process according to claim 1, wherein said compound is 1-ethoxy-1,2-di-(4''-chloro-phenyl)-(1,2-diphosphacyclopenten-(5)-one-(4)) -tricarboxylic acid-(3,3,5)-triethylester.
Claim 8
Dependent Claim
12 words
Process according to claim 1, wherein said compound is 1-ethoxy-1,2-di-(4''-methyl-phenyl)-(1,2-diphosphacyclopenten-(5)-one-(4)) -tricarboxylic acid-(3,3,5)-triethylester.
Claim 9
Dependent Claim
12 words
Process according to claim 1, wherein said compound is 1-ethoxy-1,2-di-(4''-dimethylamino-phenyl)-(1,2-diphosphacyclopenten-(5)-one -(4))-tricarboxylic acid-(3,3,5)-triethylester.
Claim 10
Dependent Claim
12 words
Process according to claim 1, wherein said compound is 1-ethoxy-1,2-di-(4''-fluoro-phenyl)-(1,2-diphosphacyclopenten-(5)-one-(4)) -tricarboxylic acid-(3,3,5)-triethylester.
Claim 11
Dependent Claim
12 words
Process according to claim 1, wherein said compound is 1-ethoxy-1,2-di-(2''-tert.-butyl-phenoxy)-(1,2-diphosphacyclopenten-(5)-one -()-one-(4))-tricarboxylic acid-(3,3,5)triethylester.
Claim 12
Dependent Claim
12 words
Process according to claim 1, wherein said compound is 1-ethoxy-1,2-di-(2'',5''-dimethyl-phenyl)-(1,2-diphosphacyclopenten-(5)-one -(4))-tricarboxylic acid-(3,3,5)-triethylester.
Claim 13
Dependent Claim
12 words
Process according to claim 1, wherein said compound is 1-ethoxy-1,2-di-(N-methyl-anilino)-(1,2-diphosphacyclopenten-(5)-one-(4)) -tricarboxylic acid-(3,3,5)-triethylester.
Claim 14
Dependent Claim
11 words
Process according to claim 1, wherein said compound is 1-methoxy-1,2-diphenyl-(1,2-diphosphacyclopenten-(5)-one-(4))-tricarboxylic acid-(3,3,5)-trimethylester.
Claim 15
Dependent Claim
12 words
Process according to claim 1, wherein said compound is 1-tert.-butoxy-1,2-diphenyl-(1,2-diphosphacyclopenten-(5)-one-(4)) -tricarboxylic acid-(3,3,5)tri-tert.-butylester.
Claim 16
Dependent Claim
11 words
Process according to claim 1, wherein said compound is 1-tert.-butoxy-1,2-di-(4''dimethylamino-phenyl)-(1,2-diphosphacyclopenten-(5)-one-(4))-tricarboxylic acid-(3,3,5)-tri-tert.-butylester.
Claim 17
Dependent Claim
11 words
Process according to claim 1, wherein said compound is 1-ethoxy-1,2-di-n-butyl-(1,2-diphosphacyclopenten-(5)-one-(4))-tricarboxylic acid-(3,3,5)-triethylester.
Claim 18
Dependent Claim
10 words
Process according to claim 1, wherein said catalyst includes alkalihydroxide.
Claim 19
Dependent Claim
14 words
Process according to claim 1, wherein said catalyst includes at least one tertiary amine.
Claim 20
Dependent Claim
10 words
Process according to claim 20, said tertiary amine being triethylamine.
Claim 21
Dependent Claim
12 words
Process according to claim 1, wherein cobalt is the Group VIII metal.
Claim 22
Dependent Claim
12 words
Process according to claim 1, wherein rhodium is the Group VIII metal.
Claim 23
Dependent Claim
12 words
Process according to claim 1, wherein ruthenium is the Group VIII metal.
Claim 24
Dependent Claim
21 words
Process according to claim 1, wherein an atomic ratio of Group VIII metal to phosphorus of 1:0.5 to 1:10 is maintained.
Claim 25
Dependent Claim
51 words
Process according to claim 4, wherein: a. the temperature is about 70* to 250* C, b. the pressure is about 50 to 400 atm., c. the atomic ratio of said Group VIII metal to phosphorus is 1: 0.5 to 1:10, d. said Group VIII metal is cobalt, rhodium, or ruthenium or.
References Cited (Backward Citations)
US3351666A
Cited
US3496204A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1975-08-01 | 1976-01-31 | 1976-08-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-08-01 | 1980-01-31 | 1980-08-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-08-01 | 1984-01-31 | 1984-08-01 | $7700.00 | Window Closed / Lapsed |