US3965192A
Expired / Lapsed
US
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Hydrocarbonylation process
Assignee: Union Oil Company of California
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Filing: 1969-08-06
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Granted: 1976-06-22
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Expires: 1989-08-06
Abstract
Abstract The homogeneous catalysis of the hydrocarbonylation of mono-olefins and non-conjugated polyolefins using a catalyst comprising a complex between an organic ligand and a Group VIII noble metal hydride carbonyl. The reaction is performed at mild conditions including temperatures from 50°-200°C. and pressures from 1 to 10,000 atmospheres to produce a predominantly aldehyde product having a high normal to iso distribution. The aldehyde products so produced are useful as intermediates for hydrogenation to aliphatic alcohols, for aldol condensation to produce plasticizers, for oxidation to produce aliphatic acids, etc.
Inventors
- 👤 Frank B. Booth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 07:33
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/16; B01J31/24; B01J31/2404; B01J31/20; C; C07; C07C; C07C45/00; C07C45/49; C07C45/50; C07F; C07F15/00; C07F15/0006; C07F15/0073; C07F15/008; B01J2231/00; B01J2231/30; B01J2231/32; B01J2231/321; B01J2531/00; B01J2531/80; B01J2531/84; B01J2531/845
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
183 words
The hydrocarbonylation of a monocyclic, mono-olefin having from 4 to about 18 carbons and the structure: R.sub.1 R.sub.2 C=CR.sub.3 R.sub.4 wherein R 1 , R 2 , R 3 and R 4 are selected from hydrogen and alkyl and wherein one of said R 1 and R 2 and one of said R 3 and R 4 together form a single alkylene group having from 2 to about 8 carbons that comprises: contacting in a reaction zone said mono-olefin, hydrogen and carbon monoxide in the presence of a liquid reaction medium containing a catalyst consisting of RhH(CO)L 3 , wherein L is an organic ligand having the formula: P(R').sub.3 wherein; R' is a member of the class consisting of alkyl from 1 to 8 carbons, aryl from 6 to 8 carbons; and at least one of said R' groups is aryl; and maintaining reaction conditions comprising the temperature of the reaction zone from about 50° to 200°C. and sufficient pressure from 5 to 300 atmospheres to maintain the reaction medium in liquid phase, said conditions being sufficient to effect hydrocarbonylation of said olefin.
Claim 2
Dependent Claim
183 words
The hydrocarbonylation of a monocyclic, mono-olefin having from 4 to about 18 carbons and the structure: R.sub.1 R.sub.2 C=CR.sub.3 R.sub.4 wherein R 1 , R 2 , R 3 and R 4 are selected from hydrogen and alkyl and wherein one of said R 1 and R 2 and one of said R 3 and R 4 together form a single alkylene group having from 2 to about 8 carbons that comprises: contacting in a reaction zone said mono-olefin, hydrogen and carbon monoxide in the presence of a liquid reaction medium containing a catalyst consisting of RhH(CO)L 3 , wherein L is an organic ligand having the formula: P(R').sub.3 wherein; R' is a member of the class consisting of alkyl from 1 to 8 carbons, aryl from 6 to 8 carbons; and at least one of said R' groups is aryl; and maintaining reaction conditions comprising the temperature of the reaction zone from about 50° to 200°C. and sufficient pressure from 5 to 300 atmospheres to maintain the reaction medium in liquid phase, said conditions being sufficient to effect hydrocarbonylation of said olefin.
Claim 3
Dependent Claim
11 words
The hydrocarbonylation of claim 1 wherein said R' groups are phenyl.
Claim 4
Dependent Claim
14 words
The hydrocarbonylation of claim 2 wherein said temperature is maintained from 70° to 160°C.
Claim 5
Dependent Claim
25 words
The hydrocarbonylation of claim 2 wherein said ligand is present in an amount from 2 to 100 times the stoichiometric equivalent thereof in said catalyst.
Claim 6
Dependent Claim
13 words
The hydrocarbonylation of claim 1 wherein all of said R' groups are aryl.
Claim 7
Dependent Claim
201 words
The hydrocarbonylation of a mono-cyclic, mono-olefin having from 4 to about 18 carbons and the structure: R 1 R 2 C=CR 3 R 4 wherein R 1 , R 2 , R 3 and R 4 are selected from hydrogen and alkyl and wherein one of said R 1 and R 2 and one of said R 3 and R 4 together form a single alkylene group having from 2 to about 8 carbons that comprises: initiating the contacting of said mono-olefin, carbon monoxide and hydrogen in the presence of a catalytic amount of the following complex: Rh(CO)H[P(R').sub.3 ].sub.3 and a molal excess of said P(R') 3 from 2 to about 100 times the stoichiometric amount in said complex; wherein: R' is the same or different alkyl from 1 to 8 carbons or aryl from 6 to 8 carbons; and at least one of said R' groups is aryl; and continuing to contact said olefin, carbon monoxide and hydrogen with said reaction medium while maintaining the temperature of the reaction zone from about 50° to 200°C. and under sufficient pressure, from 10 to 100 atmospheres, to maintain the reaction medium in liquid phase and form a carbonyl product from said olefin.
Claim 8
Dependent Claim
201 words
The hydrocarbonylation of a mono-cyclic, mono-olefin having from 4 to about 18 carbons and the structure: R 1 R 2 C=CR 3 R 4 wherein R 1 , R 2 , R 3 and R 4 are selected from hydrogen and alkyl and wherein one of said R 1 and R 2 and one of said R 3 and R 4 together form a single alkylene group having from 2 to about 8 carbons that comprises: initiating the contacting of said mono-olefin, carbon monoxide and hydrogen in the presence of a catalytic amount of the following complex: Rh(CO)H[P(R').sub.3 ].sub.3 and a molal excess of said P(R') 3 from 2 to about 100 times the stoichiometric amount in said complex; wherein: R' is the same or different alkyl from 1 to 8 carbons or aryl from 6 to 8 carbons; and at least one of said R' groups is aryl; and continuing to contact said olefin, carbon monoxide and hydrogen with said reaction medium while maintaining the temperature of the reaction zone from about 50° to 200°C. and under sufficient pressure, from 10 to 100 atmospheres, to maintain the reaction medium in liquid phase and form a carbonyl product from said olefin.
Claim 9
Dependent Claim
12 words
The hydrocarbonylation of claim 6 wherein all said R' groups are aryl.
Claim 10
Dependent Claim
11 words
The hydrocarbonylation of claim 7 wherein said R' groups are phenyl.
Claim 11
Dependent Claim
28 words
The hydrocarbonylation of claim 8 wherein said P(R') 3 is present in an amount from 5 to 20 times the stoichiometric equivalent thereof in combination with said complex.
Claim 12
Dependent Claim
14 words
The hydrocarbonylation of claim 6 wherein said temperature is maintained from 70° to 160°C.
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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) | 1979-06-22 | 1979-12-22 | 1980-06-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-22 | 1983-12-22 | 1984-06-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-22 | 1987-12-22 | 1988-06-22 | $7700.00 | Window Closed / Lapsed |