US4200591A
Expired / Lapsed
US
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Catalytic hydroformylation
Assignee: Johnson Matthey PLC
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Filing: 1978-06-19
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Granted: 1980-04-29
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Expires: 1998-06-19
Abstract
Abstract This invention relates to catalytic hydroformylation of internal olefins. In particular the invention relates to a process for the production of a straight chain aldehyde from an olefin comprising reacting said olefin in a liquid reaction medium with hydrogen and carbon monoxide in the presence of a complex of Rh(I) in solution in the said medium as catalyst and a heterogeneous co-catalyst comprising a catalytic metal deposited upon a solid particulate support.
Inventors
- 👤 Rosemary R. Hignett
- 👤 Peter J. Davidson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 19:45
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/49; C07C45/50
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
163 words
A process for the production of a straight chain aldehyde from an internal olefin selected from the group consisting of 2-pentene, 2-hexene, 3-hexene and 2-butene which comprises reacting said olefin at a temperature of 115° to 140° C. in a liquid reaction medium and at an elevated pressure less than 200 psi with hydrogen and carbon monoxide in the presence of an hydride carbonyl complex of Rh(I) including a triaryl phosphine or triaryl phosphite stabilizing donor ligand, said complex being in solution in the said medium as catalyst and a heterogeneous co-catalyst comprising a catalytic metal deposited upon a solid particulate support, said catalytic metal being a metal selected from the group consisting of Ru, Rh, Pd, Ir, Pt and alloys thereof in which at least 10% by weight of one or more of the said metals is present, the molar ratio in the reaction medium of catalytic metal deposited upon the catalyst support to catalyst being within the range 20:1 to 1:20.
Claim 2
Dependent Claim
163 words
A process for the production of a straight chain aldehyde from an internal olefin selected from the group consisting of 2-pentene, 2-hexene, 3-hexene and 2-butene which comprises reacting said olefin at a temperature of 115° to 140° C. in a liquid reaction medium and at an elevated pressure less than 200 psi with hydrogen and carbon monoxide in the presence of an hydride carbonyl complex of Rh(I) including a triaryl phosphine or triaryl phosphite stabilizing donor ligand, said complex being in solution in the said medium as catalyst and a heterogeneous co-catalyst comprising a catalytic metal deposited upon a solid particulate support, said catalytic metal being a metal selected from the group consisting of Ru, Rh, Pd, Ir, Pt and alloys thereof in which at least 10% by weight of one or more of the said metals is present, the molar ratio in the reaction medium of catalytic metal deposited upon the catalyst support to catalyst being within the range 20:1 to 1:20.
Claim 3
Dependent Claim
22 words
A process according to claim 1 in which an approximately equimolar ratio of catalytic metal in the co-catalyst and catalyst is used.
Claim 4
Dependent Claim
14 words
A process according to claim 1 in which the triaryl phosphite is triphenyl phosphite.
Claim 5
Dependent Claim
13 words
A process according to claim 1 wherein the triaryl phosphine is triphenyl phosphine.
Claim 6
Dependent Claim
18 words
A process according to claim 1 in which the hydrido carbonyl complex of rhodium is RhH(CO)(PPh.sub.3).sub.3 or RhH(CO)(PPh.sub.3).sub.2.
Claim 7
Dependent Claim
18 words
A process according to claim 1 in which the hydrido carbonyl complex of rhodium is RhH(CO)((P(OPh).sub.3)).sub.3 or RhH(CO)((P(OPh).sub.3)).sub.2.
Claim 8
Dependent Claim
16 words
A process according to claim 1 in which the hydrido carbonyl complex of rhodium is RhH(CO.sub.2)(PPh.sub.3).sub.2.
Claim 9
Dependent Claim
21 words
A process according to claim 1 in which the hydrido carbonyl complex of rhodium RhH(CO) 2 ((P(OPh) 3 )) 2 .
Claim 10
Dependent Claim
15 words
A process according to claim 1 wherein the hydrido carbonyl complex is generated in situ.
Claim 11
Dependent Claim
43 words
A process according to claim 9 wherein the hydrido carbonyl complex is generated from RhX(CO)(PR.sub.3).sub.3 or RhX.sub.3 (PR.sub.3).sub.3 or RhX(CO)(PR.sub.3).sub.2 where X is a halogen or pseudo-halogen and R is an alkyl, aryl, aralkyl, alkaryl, or substituted alkyl, aryl, aralkyl or alkaryl group.
Claim 12
Dependent Claim
12 words
A process according to claim 10 including an acceptor for hydrogen halide.
Claim 13
Dependent Claim
13 words
A process according to claim 11 wherein the acceptor is an organic base.
Claim 14
Dependent Claim
12 words
A process according to claim 12 wherein the organic base is triethylamine.
Claim 15
Dependent Claim
15 words
A process according to claim 13 wherein the acceptor is the phosphorus-containing stabilizing donor ligand.
Claim 16
Dependent Claim
41 words
A process according to claim 9 in which the source of rhodium is a trivalent rhodium salt, a rhodium carbonyl, a rhodium (II) carboxylate, a rhodium (I) carbonyl carboxylate, a rhodium oxide, a rhodium (III) β-diketonate, or a rhodium carbonyl β-diketonate.
Claim 17
Dependent Claim
13 words
A process according to claim 15 wherein the rhodium carboxylate is the acetate.
Claim 18
Dependent Claim
11 words
A process according to claim 15 wherein the β-diketonate is acetylacetonate.
Claim 19
Dependent Claim
22 words
A process according to any preceding claim wherein the molecular ratio of H 2 :CO is within the range 1:15 to 5:1.
Claim 20
Dependent Claim
21 words
A process according to claim 18 wherein the molecular ratio of H 2 :CO is within the range 5:1 to 1:6.
Claim 21
Dependent Claim
14 words
A process according to claim 1 wherein the temperature range is 120° C.-130° C.
Claim 22
Dependent Claim
18 words
A process according to claim 1 wherein the ligand/catalyst ratio lies within the range of 1:1 to 500:1.
Claim 23
Dependent Claim
12 words
A process according to claim 2 wherein the ligand/catalyst ratio is 200:1.
References Cited (Backward Citations)
US3378590A
Cited
GB1338225A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-04-29 | 1983-10-29 | 1984-04-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-29 | 1987-10-29 | 1988-04-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-29 | 1991-10-29 | 1992-04-29 | $7700.00 | Window Closed / Lapsed |