US4720474A
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Olefin oxidation catalyst system
Assignee: CATALYTICA ASSOCIATES A CALIFORNIA LP
•
Filing: 1985-09-24
•
Granted: 1988-01-19
•
Expires: 2005-09-24
Abstract
Abstract The addition of redox-active metal components and ligands, alternatively or simultaneously, results in increased conversion and selectivity in the palladium-catalyzed oxidation of olefins to carbonyl products in the presence of polyoxoanions. In preferred modes, heteropolyoxoanions and isopolyoxoanions containing tungsten, molybdenum and vanadium, individually or in combination, are described. The use of copper as the redox-active metal component shows reduced allylic reactivity. The elimination of chloride from the catalyst system provides substantial engineering advantages over the prior art, particularly, the reduction of corrosion and chloro-organic by-product formation. The use of redox-active metal components and/or ligands makes the palladium-polyoxoanion catalyst system industrially practicable.
Inventors
- 👤 Janis Vasilevskis
- 👤 Jacques C. De Deken
- 👤 Robert J. Saxton
- 👤 Paul R. Wentrcek
- 👤 Jere D. Fellmann
- 👤 Lyubov S. Kipnis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 11:46
CPC Classifications
B; B01; B01J; B01J23/00; B01J23/70; B01J23/76; B01J23/84; C; C07; C07C; C07C45/00; C07C45/27; C07C45/32; C07C45/33; C07C45/34; C07C45/35; B01J31/00; B01J31/16; B01J31/18; B01J31/1805; B01J31/26; B01J31/28; B01J2531/00; B01J2531/80; B01J2531/82; B01J2531/824
Claims Analysis
Total Claims: 70
Claim 1
Independent Claim
129 words
A catalyst system useful for olefin oxidation to a carbonyl product which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x M.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M, M' and M" are members independently selected from the group consisting of W, Mo, V, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed isopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and a+b+c≧2; (b) at least one palladium component; and (c) at least one nitrile ligand.
Claim 2
Dependent Claim
129 words
A catalyst system useful for olefin oxidation to a carbonyl product which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x M.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M, M' and M" are members independently selected from the group consisting of W, Mo, V, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed isopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and a+b+c≧2; (b) at least one palladium component; and (c) at least one nitrile ligand.
Claim 3
Dependent Claim
11 words
The catalyst system of claim 1 wherein the ligand is acetonitrile.
Claim 4
Dependent Claim
158 words
An unsupported, aqueous catalyst system useful for olefin oxidation to a carbonyl product which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x M.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M, M' and M" are members independently selected from the group consisting of W, Mo, V, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed isopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and a+b+c≧2; (b) at least one palladium component; and (c) at least one redox active metal component wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides and esters of nitrous acid.
Claim 5
Dependent Claim
158 words
An unsupported, aqueous catalyst system useful for olefin oxidation to a carbonyl product which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x M.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M, M' and M" are members independently selected from the group consisting of W, Mo, V, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed isopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and a+b+c≧2; (b) at least one palladium component; and (c) at least one redox active metal component wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides and esters of nitrous acid.
Claim 6
Dependent Claim
34 words
The catalyst system of claim 3 wherein said redox active metal component is a member selected from the group consisting of CuSO 4 , Cu(CH 3 COO) 2 and Cu(NO 3 ) 2 .
Claim 7
Dependent Claim
32 words
The catalyst system of claim 3 wherein said redox active metal component is a member selected from the group consisting of Fe(CH 3 COO) 2 , FeSO 4 and MnSO 4 .
Claim 8
Dependent Claim
148 words
An unsupported aqueous catalyst system useful for olefin oxidation to a carbonyl product which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x M.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M, M' and M" are members independently selected from the group consisting of W, Mo, V, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed isopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and a+b+c≧2; (b) at least one palladium component; and (c) at least one redox active metal component, wherein said redox active metal component is provided separate and distinct from said polyoxoanion component.
Claim 9
Dependent Claim
148 words
An unsupported aqueous catalyst system useful for olefin oxidation to a carbonyl product which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x M.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M, M' and M" are members independently selected from the group consisting of W, Mo, V, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed isopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and a+b+c≧2; (b) at least one palladium component; and (c) at least one redox active metal component, wherein said redox active metal component is provided separate and distinct from said polyoxoanion component.
Claim 10
Dependent Claim
32 words
The catalyst system of claim 6 wherein said redox active metal component is a member selected from the group consisting of CuSO 4 , Cu(CH 3 COO) 2 and Cu(NO 3 )2.
Claim 11
Dependent Claim
30 words
The catalyst system of claim 6 wherein said redox active metal component is selected from the group consisting of Fe(CH 3 COO) 2 , FeSO 4 and MnSO 4 .
Claim 12
Dependent Claim
20 words
The catalyst system of claim 6 wherein said redox active metal is selected from the group consisting of copper salts.
Claim 13
Dependent Claim
20 words
The catalyst system of claim 6 wherein said redox active metal is selected from the group consisting of iron salts.
Claim 14
Dependent Claim
20 words
The catalyst system of claim 6 wherein said redox active metal is selected from the group consisting of manganese salts.
Claim 15
Dependent Claim
137 words
A catalyst system useful for olefin oxidation to a carbonyl product which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x M.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M, M' and M" are members independently selected from the group consisting of W, Mo, V, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed iosopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and a+b+c≧2; (b) at least one palladium component; (c) at least one redox active metal component; and, (d) at least one nitrile ligand.
Claim 16
Dependent Claim
137 words
A catalyst system useful for olefin oxidation to a carbonyl product which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x M.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M, M' and M" are members independently selected from the group consisting of W, Mo, V, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed iosopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and a+b+c≧2; (b) at least one palladium component; (c) at least one redox active metal component; and, (d) at least one nitrile ligand.
Claim 17
Dependent Claim
34 words
The catalyst system of claim 12 wherein said redox active metal component is a member selected from the group consisting of CuSO 4 , Cu(CH 3 COO) 2 and Cu(NO 3 ) 2 .
Claim 18
Dependent Claim
32 words
The catalyst system of claim 12 wherein said redox active metal component is a member selected from the group consisting of Fe(CH 3 COO) 2 , FeSO 4 and MnSO 4 .
Claim 19
Dependent Claim
11 words
The catalyst system of claim 12 wherein the ligand is acetonitrile.
Claim 20
Dependent Claim
20 words
The catalyst system of claim 12 wherein said redox active metal is selected from the group consisting of copper salts.
Claim 21
Dependent Claim
20 words
The catalyst system of claim 12 wherein said redox active metal is selected from the group consisting of iron salts.
Claim 22
Dependent Claim
20 words
The catalyst system of claim 12 wherein said redox active metal is selected from the group consisting of manganese salts.
Claim 23
Dependent Claim
54 words
An unsupported, aqueous catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one molybdenum-free polyoxoanion component; and, (b) at least one palladium component wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides and esters of nitrous acid.
Claim 24
Dependent Claim
54 words
An unsupported, aqueous catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one molybdenum-free polyoxoanion component; and, (b) at least one palladium component wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides and esters of nitrous acid.
Claim 25
Dependent Claim
62 words
An unsupported, aqueous catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one molybdenum-free polyoxoanion component; (b) at least one palladium component; and, (c) at least one redox active metal component wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides, and esters of nitrous acid.
Claim 26
Dependent Claim
62 words
An unsupported, aqueous catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one molybdenum-free polyoxoanion component; (b) at least one palladium component; and, (c) at least one redox active metal component wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides, and esters of nitrous acid.
Claim 27
Dependent Claim
20 words
The catalyst system of claim 20 wherein said redox active metal is selected from the group consisting of copper salts.
Claim 28
Dependent Claim
20 words
The catalyst system of claim 20 wherein said redox active metal is selected from the group consisting of iron salts.
Claim 29
Dependent Claim
20 words
The catalyst system of claim 20 wherein said redox active metal is selected from the group consisting of manganese salts.
Claim 30
Dependent Claim
33 words
A catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one molybdenum-free polyoxoanion component; (b) at least one palladium component; and, (c) at least one nitrile ligand.
Claim 31
Dependent Claim
33 words
A catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one molybdenum-free polyoxoanion component; (b) at least one palladium component; and, (c) at least one nitrile ligand.
Claim 32
Dependent Claim
40 words
A catalyst system useful in olefin oxidation to carbonyl compounds which comprises: (a) at least one molybdenum-free polyoxoanion component; (b) at least one palladium component; (c) at least one redox active metal component; and, (d) at least one nitrile ligand.
Claim 33
Dependent Claim
40 words
A catalyst system useful in olefin oxidation to carbonyl compounds which comprises: (a) at least one molybdenum-free polyoxoanion component; (b) at least one palladium component; (c) at least one redox active metal component; and, (d) at least one nitrile ligand.
Claim 34
Dependent Claim
20 words
The catalyst system of claim 25 wherein said redox active metal is selected from the group consisting of copper salts.
Claim 35
Dependent Claim
20 words
The catalyst system of claim 25 wherein said redox active metal is selected from the group consisting of iron salts.
Claim 36
Dependent Claim
20 words
The catalyst system of claim 25 wherein said redox active metal is selected from the group consisting of manganese salts.
Claim 37
Dependent Claim
58 words
An unsupported, aqueous catalyst system useful in olefin oxidation which comprises: (a) at least one vanadium-free polyoxoanion component; (b) at least one palladium component; and (c) at least one redox active metal component wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides and esters of nitrous acid.
Claim 38
Dependent Claim
58 words
An unsupported, aqueous catalyst system useful in olefin oxidation which comprises: (a) at least one vanadium-free polyoxoanion component; (b) at least one palladium component; and (c) at least one redox active metal component wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides and esters of nitrous acid.
Claim 39
Dependent Claim
20 words
The catalyst system of claim 29 wherein said redox active metal is selected from the group consisting of copper salts.
Claim 40
Dependent Claim
20 words
The catalyst system of claim 29 wherein said redox active metal is selected from the group consisting of iron salts.
Claim 41
Dependent Claim
20 words
The catalyst system of claim 29 wherein said redox active metal is selected from the group consisting of manganese salts.
Claim 42
Dependent Claim
29 words
A catalyst system useful in olefin oxidation which comprises: (a) at least one vanadium-free polyoxoanion component; (b) at least one palladium component; and (c) at least one nitrile ligand.
Claim 43
Dependent Claim
29 words
A catalyst system useful in olefin oxidation which comprises: (a) at least one vanadium-free polyoxoanion component; (b) at least one palladium component; and (c) at least one nitrile ligand.
Claim 44
Dependent Claim
37 words
A catalyst system useful in olefin oxidation which comprises: (a) at least one vanadium-free polyoxoanion component; (b) at least one palladium component; (c) at least one redox active metal component; and, (d) at least one nitrile ligand.
Claim 45
Dependent Claim
37 words
A catalyst system useful in olefin oxidation which comprises: (a) at least one vanadium-free polyoxoanion component; (b) at least one palladium component; (c) at least one redox active metal component; and, (d) at least one nitrile ligand.
Claim 46
Dependent Claim
20 words
The catalyst system of claim 34 wherein said redox active metal is selected from the group consisting of copper salts.
Claim 47
Dependent Claim
20 words
The catalyst system of claim 34 wherein said redox active metal is selected from the group consisting of iron salts.
Claim 48
Dependent Claim
20 words
The catalyst system of claim 34 wherein said redox active metal is selected from the group consisting of manganese salts.
Claim 49
Dependent Claim
51 words
An unsupported, aqueous catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one molybdenum-free polyoxoanion component; (b) at least one palladium component; and, (c) at least one redox active metal component, wherein said redox active metal is provided separate and distinct from said polyoxoanion component.
Claim 50
Dependent Claim
51 words
An unsupported, aqueous catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one molybdenum-free polyoxoanion component; (b) at least one palladium component; and, (c) at least one redox active metal component, wherein said redox active metal is provided separate and distinct from said polyoxoanion component.
Claim 51
Dependent Claim
48 words
An unsupported, aqueous catalyst system useful in olefin oxidation which comprises: (a) at least one vanadium-free polyoxoanion component; (b) at least one palladium component; and (c) at least one redox active metal component, wherein said redox active metal component is provided separate and distinct from said polyoxoanion component.
Claim 52
Dependent Claim
48 words
An unsupported, aqueous catalyst system useful in olefin oxidation which comprises: (a) at least one vanadium-free polyoxoanion component; (b) at least one palladium component; and (c) at least one redox active metal component, wherein said redox active metal component is provided separate and distinct from said polyoxoanion component.
Claim 53
Dependent Claim
20 words
The catalyst system of claim 39 wherein said redox active metal is selected from the group consisting of copper salts.
Claim 54
Dependent Claim
20 words
The catalyst system of claim 39 wherein said redox active metal is selected from the group consisting of iron salts.
Claim 55
Dependent Claim
20 words
The catalyst system of claim 39 wherein said redox active metal is selected from the group consisting of manganese salts.
Claim 56
Dependent Claim
164 words
An unsupported, aqueous catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x V.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M' and M" are members independently selected from the group consisting of W, Mo, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed isopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and, a+b+c≧2; (b) at least one palladium component; and, (c) at least one redox active metal component provided separate and distinct from said polyoxoanion component, wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides and esters of nitrous acid.
Claim 57
Dependent Claim
164 words
An unsupported, aqueous catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x V.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M' and M" are members independently selected from the group consisting of W, Mo, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed isopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and, a+b+c≧2; (b) at least one palladium component; and, (c) at least one redox active metal component provided separate and distinct from said polyoxoanion component, wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides and esters of nitrous acid.
Claim 58
Dependent Claim
20 words
The catalyst system of claim 43 wherein said redox active metal is selected from the group consisting of manganese salts.
Claim 59
Dependent Claim
20 words
The catalyst system of claim 43 wherein said redox active metal is selected from the group consisting of copper salts.
Claim 60
Dependent Claim
20 words
The catalyst system of claim 43 wherein said redox active metal is selected from their group consisting of iron salts.
Claim 61
Dependent Claim
34 words
The catalyst system of claim 43 wherein said redox active metal component is a member selected from the group consisting of CuSO 4 , Cu(CH 3 COO) 2 and Cu(NO 3 ) 2 .
Claim 62
Dependent Claim
29 words
The catalyst system of claim 43 wherein said redox active metal is selected from the group consisting of Fe(CH 3 COO) 2 , FeSO 4 and MnSO 4 .
Claim 63
Dependent Claim
170 words
An unsupported, aqueous catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x V.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M' and M" are members independently selected from the group consisting of W, Mo, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed isopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and, a+b+c≧2; (b) at least one palladium component; (c) at least one redox active metal component provided separate and distinct from said polyoxoanion component; and, (d) at least one nitrile ligand, wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides and esters of nitrous acid.
Claim 64
Dependent Claim
170 words
An unsupported, aqueous catalyst system useful in olefin oxidation to a carbonyl compound which comprises: (a) at least one polyoxoanion component which is a member selected from the group consisting of compounds which have the general formula: [X.sub.x V.sub.a M'.sub.b M".sub.c O.sub.z ].sup.-m wherein X is a member selected from the group consisting of B, Si, Ge, P, As, Se, Te, I, Co, Mn and Cu; M' and M" are members independently selected from the group consisting of W, Mo, Nb, Ta and Re; x is zero for isopolyoxoanions and mixed isopolyoxoanions; x is an integer greater than zero for heteropolyoxoanions; a, z and m are integers greater than zero; b, c are integers; and, a+b+c≧2; (b) at least one palladium component; (c) at least one redox active metal component provided separate and distinct from said polyoxoanion component; and, (d) at least one nitrile ligand, wherein said catalyst system is substantially free of nitrogen compounds selected from the group consisting of nitric acid, nitrogen oxides and esters of nitrous acid.
Claim 65
Dependent Claim
20 words
The catalyst system of claim 49 wherein said redox active metal is selected from the group consisting of copper salts.
Claim 66
Dependent Claim
20 words
The catalyst system of claim 49 wherein said redox active metal is selected from the group consisting of iron salts.
Claim 67
Dependent Claim
20 words
The catalyst system of claim 49 wherein said redox active metal is selected from the group consisting of manganese salts.
Claim 68
Dependent Claim
31 words
The catalyst system of claim 49 wherein said redox active metal is selected from the group consisting of CuSO 4 , Cu(CH 3 COO) 2 and Cu(NO 3 ) 2 .
Claim 69
Dependent Claim
29 words
The catalyst system of claim 49 wherein said redox active metal is selected from the group consisting of Fe(CH 3 COO) 2 , FeSO 4 and MnSO 4 .
Claim 70
Dependent Claim
12 words
The catalyst system of claim 49 wherein said nitrile ligand is acetonitrile.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-01-18 | 1991-07-20 | 1992-01-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-01-18 | 1995-07-20 | 1996-01-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-01-18 | 1999-07-20 | 2000-01-19 | $7700.00 | Window Closed / Lapsed |