US3933861A
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US
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Production of tetrahydrofurans
Assignee: Chevron USA Inc
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Filing: 1974-01-07
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Granted: 1976-01-20
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Expires: 1994-01-07
Abstract
Abstract Tetrahydrofurans are produced by the codimerization of an alkene oxide with an alkene in the presence of catalytic amounts of a Group VIII noble transition metal compound and an iodide promoter.
Inventors
- 👤 Victor P. Kurkov
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 20:49
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/04; C07D307/06; C07D307/08; B; B01; B01J; B01J31/00; B01J31/16; B01J31/20; B01J31/24; B01J31/2404; B01J31/2409; B01J2531/00; B01J2531/80; B01J2531/82; B01J2531/821; B01J2531/822; B01J2531/824
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
202 words
A process for producing tetrahydrofurans which comprises codimerizing in the gaseous or liquid phase an alkene oxide of 2 to 6 carbon atoms of the formula ##EQU3## with an alkene of 2 to 6 carbon atoms of the formula R 5 R 6 C=CR 7 R 8 wherein R 1 , R 2 , R 3 , R.sub. 4, R 5 , R 6 , R 7 , and R 8 represent hydrogen or an alkyl group of 1 to 4 carbon atoms, in the presence of catalytic amounts of a Group VIII noble transition metal compound of the formula M(L) n (X) m , wherein M represents Ru, Rh, Pd, Os, Ir or Pt; n is 0 to 5 inclusive; m is 0 to 3 inclusive; n + m is 3 to 6 inclusive; L represents non-ionic organic ligands complexed to M selected from the group consisting of water, carbon monoxide, olefin and hydrocarbyl phosphine, arsine, stibine, and bismuthine; and X represents inorganic ions bonded to M selected from the group consisting of halide, hydride and nitrite, and an iodide promoter selected from the group consisting of iodine, hydrogen iodide, alkyl iodide and iodohydrin, at a temperature from 100°C to 250°C.
Claim 2
Dependent Claim
202 words
A process for producing tetrahydrofurans which comprises codimerizing in the gaseous or liquid phase an alkene oxide of 2 to 6 carbon atoms of the formula ##EQU3## with an alkene of 2 to 6 carbon atoms of the formula R 5 R 6 C=CR 7 R 8 wherein R 1 , R 2 , R 3 , R.sub. 4, R 5 , R 6 , R 7 , and R 8 represent hydrogen or an alkyl group of 1 to 4 carbon atoms, in the presence of catalytic amounts of a Group VIII noble transition metal compound of the formula M(L) n (X) m , wherein M represents Ru, Rh, Pd, Os, Ir or Pt; n is 0 to 5 inclusive; m is 0 to 3 inclusive; n + m is 3 to 6 inclusive; L represents non-ionic organic ligands complexed to M selected from the group consisting of water, carbon monoxide, olefin and hydrocarbyl phosphine, arsine, stibine, and bismuthine; and X represents inorganic ions bonded to M selected from the group consisting of halide, hydride and nitrite, and an iodide promoter selected from the group consisting of iodine, hydrogen iodide, alkyl iodide and iodohydrin, at a temperature from 100°C to 250°C.
Claim 3
Dependent Claim
11 words
The process of claim 1 wherein M represents Ru or Pd.
Claim 4
Dependent Claim
33 words
The process of claim 2 wherein the alkene oxide is an n-alkene oxide and the alkene is a terminal n-alkene, and the molar ratio of alkene to alkene oxide is 10:1 to 1:1.
Claim 5
Dependent Claim
9 words
The process of claim 3 wherein m is 0.
Claim 6
Dependent Claim
13 words
The process of claim 3 wherein M represents Ru and L represents CO.
Claim 7
Dependent Claim
32 words
The process of claim 3 wherein the alkene oxide is ethylene oxide, the alkene is ethylene, and the ethylene is provided at an initial partial pressure of 100 psia to 1,000 psia.
Claim 8
Dependent Claim
31 words
The process of claim 3 wherein the alkene oxide is propylene oxide, the alkene is ethylene and the ethylene is provided at a partial pressure of 100 psia to 1,000 psia.
Claim 9
Dependent Claim
128 words
A process for producing tetrahydrofurans which comprises codimerizing in the gaseous or liquid phase an alkene oxide of 2 to 6 carbon atoms of the formula ##EQU4## with an alkene of 2 to 6 carbon atoms of the formula R 5 R 6 C=CR 7 R 8 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , represent hydrogen or an alkyl group of 1 to 4 carbon atoms, in the presence of catalytic amounts of a zero-valent ruthenium or palladium trihydrocarbylphosphine of 3 to 20 carbon atoms and an iodide promoter selected from the group consisting of iodine, hydrogen iodide, alkyl iodide, and iodohydrin, at a temperature from 100°C to 250°C.
Claim 10
Dependent Claim
128 words
A process for producing tetrahydrofurans which comprises codimerizing in the gaseous or liquid phase an alkene oxide of 2 to 6 carbon atoms of the formula ##EQU4## with an alkene of 2 to 6 carbon atoms of the formula R 5 R 6 C=CR 7 R 8 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , represent hydrogen or an alkyl group of 1 to 4 carbon atoms, in the presence of catalytic amounts of a zero-valent ruthenium or palladium trihydrocarbylphosphine of 3 to 20 carbon atoms and an iodide promoter selected from the group consisting of iodine, hydrogen iodide, alkyl iodide, and iodohydrin, at a temperature from 100°C to 250°C.
Claim 11
Dependent Claim
120 words
A process for producing tetrahydrofurans which comprises codimerizing in the gaseous or liquid phase an alkene oxide of 2 to 6 carbon atoms of the formula ##EQU5## with an alkene of 2 to 6 carbon atoms of the formula R 5 R 6 C=CR 7 R 8 wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , and R 8 represent hydrogen or an alkyl group of 1 to 4 carbon atoms, in the presence of catalytic amounts of a ruthenium or palladium carbonyl trimethylphosphine or triphenylphosphine and an iodide promoter selected from the group consisting of iodine, hydrogen iodide, alkyl iodide and iodohydrin, at a temperature from 100° to 250°C.
Claim 12
Dependent Claim
120 words
A process for producing tetrahydrofurans which comprises codimerizing in the gaseous or liquid phase an alkene oxide of 2 to 6 carbon atoms of the formula ##EQU5## with an alkene of 2 to 6 carbon atoms of the formula R 5 R 6 C=CR 7 R 8 wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , and R 8 represent hydrogen or an alkyl group of 1 to 4 carbon atoms, in the presence of catalytic amounts of a ruthenium or palladium carbonyl trimethylphosphine or triphenylphosphine and an iodide promoter selected from the group consisting of iodine, hydrogen iodide, alkyl iodide and iodohydrin, at a temperature from 100° to 250°C.
Claim 13
Dependent Claim
30 words
The process of claim 9 wherein the alkene oxide is ethylene oxide, the alkene is ethylene and the iodide promoter is iodine, hydrogen iodide, an alkyl iodide or an iodohydrin.
Claim 14
Dependent Claim
53 words
The process of claim 9 wherein the alkene oxide is ethylene oxide, the alkene is ethylene, and the ethylene is provided at an initial partial pressure of 100 psia to 1,000 psia, the iodide promoter is hydrogen iodide and the catalyst is Ru(CO) 3 [P(C 6 H 5 ) 3 ] 2 .
References Cited (Backward Citations)
US3317567A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-19 | 1979-07-21 | 1980-01-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-19 | 1983-07-21 | 1984-01-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-19 | 1987-07-21 | 1988-01-20 | $7700.00 | Window Closed / Lapsed |