US4200592A
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 reactions, for example the 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 the said olefin in a liquid reaction medium with hydrogen and carbon monoxide at a total pressure of less than 500 psig in the presence of a complex of Rh(I) in solution in the said medium and a homogeneous co-catalyst dissolved in said reaction medium comprising a co-ordination complex of a transition metal other than rhodium selected from Group 6 or Group 8 of the Periodic Table. The transition metal is, preferably, selected from the group consisting of Cr, Mo, W, Fe, Co, Pd, Pt and Ru.
Inventors
- 👤 Rosemary R. Hignett
- 👤 Peter J. Davidson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 19:46
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/49; C07C45/50
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
169 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 the said olefin at a temperature between 80° and 140° C. in a liquid reaction medium with hydrogen and carbon monoxide at a total pressure of at least 1 atmosphere and less than 500 psig in the presence of an hydrido carbonyl complex of Rh(I) including a triaryl phosphite or triaryl phosphine stabilizing donor ligand, said complex being in solution in the said medium and a homogeneous co-catalyst also dissolved in said reaction medium comprising a co-ordination compound selected from the group consisting of Pd(acac) 2 , (PhCN) 2 PdCl 2 , Mo(CO) 6 , Fe 2 (CO) 9 , Co 2 (CO) 8 , Cr(CO) 6 , Ru 3 (CO) 12 , W(CO) 6 , Pt(PPh 3 ) 4 and Pd(PPh 3 ) 4 , the molar ratio of co-catalyst complex present to Rh(I) complex present being greater than 1:1.
Claim 2
Dependent Claim
169 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 the said olefin at a temperature between 80° and 140° C. in a liquid reaction medium with hydrogen and carbon monoxide at a total pressure of at least 1 atmosphere and less than 500 psig in the presence of an hydrido carbonyl complex of Rh(I) including a triaryl phosphite or triaryl phosphine stabilizing donor ligand, said complex being in solution in the said medium and a homogeneous co-catalyst also dissolved in said reaction medium comprising a co-ordination compound selected from the group consisting of Pd(acac) 2 , (PhCN) 2 PdCl 2 , Mo(CO) 6 , Fe 2 (CO) 9 , Co 2 (CO) 8 , Cr(CO) 6 , Ru 3 (CO) 12 , W(CO) 6 , Pt(PPh 3 ) 4 and Pd(PPh 3 ) 4 , the molar ratio of co-catalyst complex present to Rh(I) complex present being greater than 1:1.
Claim 3
Dependent Claim
18 words
A process according to claim 1 in which the molar ratio is within the range 2:1 to 100:1.
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
20 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
17 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
22 words
A process according to claim 1 in which the hydrido carbonyl complex of rhodium is 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 stabilising donor ligand.
Claim 16
Dependent Claim
42 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
21 words
A process according to claim 1 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
18 words
A process according to claim 18 which is carried out at a total pressure less than 200 psi.
Claim 22
Dependent Claim
19 words
A process according to claim 20 which is carried out at a temperature within the range 115° C.-140° C.
Claim 23
Dependent Claim
14 words
A process according to claim 21 wherein the temperature range is 120° C.-130° C.
Claim 24
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 25
Dependent Claim
12 words
A process according to claim 23 wherein the ligand/catalyst ratio is 200:1.
References Cited (Backward Citations)
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 |