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US4262142A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydroformylation of ethylene with higher olefins

Assignee: Union Carbide Corp
•
Filing: 1979-12-28
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Granted: 1981-04-14
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Expires: 1999-12-28
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Abstract

Abstract In a rhodium-catalyzed hydroformylation process employing olefin reactants having from 3 to 20 carbon atoms to produce products rich in normal aldehydes, the efficiency of the catalyst in producing such products is substantially uneffected and propionaldehyde is also produced by employing ethylene as a coreactant along with the olefin.

Inventors

  • 👤 Paul D. Sherman, Jr.
  • 👤 Stephen C. Winans
  • 👤 Dennis G. Morrell

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 20:21
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/49; C07C45/50; C07C47/00; C07C47/02

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 256 words
In a process for the production of oxygenated products comprising aldehydes having a high normal/iso aldehyde ratio which process comprises (1) forming a reaction mixture containing (a) an alpha olefinic hydrocarbon having from 3 to 20 carbon atoms; (b) carbon monoxide; (c) hydrogen; (d) a catalytic quantity of a complex catalyst consisting essentially of rhodium in complex combination with (i) carbon monoxide and (ii) a triorgano phosphorus ligand of the group consisting of trialkylphosphites, tricycloalkylphosphites, triarylphosphites, and triarylphosphines; each organic moiety thereof having up to 18 carbon atoms; and said triorgano phosphorus ligand possessing a Δ HNP value of at least about 425; and (e) at least 2 moles of free ligand as defined above per mole of rhodium; (2) maintaining the reaction mixture at a temperature in the range of from about 50° C. to 145° C.; at a total pressure of carbon monoxide and hydrogen of less than 450 psia, and a partial pressure attributable to carbon monoxide no greater than about 75 percent of said total pressure; thereby (3) reacting said olefinic hydrocarbon with said carbon monoxide and hydrogen with the formation of said oxygenated products comprising aldehydes having a high normal/iso aldehyde ratio, the improvement which consists in including in said reaction mixture ethylene and additional carbon monoxide and hydrogen in amounts at least sufficient to react with said ethylene and reacting said ethylene with said carbon monoxide and hydrogen with the formation of propionaldehyde in addition to and concurrently with said oxygenated products comprising aldehydes having a high normal/iso aldehyde ratio.
Claim 2
Dependent Claim 256 words
In a process for the production of oxygenated products comprising aldehydes having a high normal/iso aldehyde ratio which process comprises (1) forming a reaction mixture containing (a) an alpha olefinic hydrocarbon having from 3 to 20 carbon atoms; (b) carbon monoxide; (c) hydrogen; (d) a catalytic quantity of a complex catalyst consisting essentially of rhodium in complex combination with (i) carbon monoxide and (ii) a triorgano phosphorus ligand of the group consisting of trialkylphosphites, tricycloalkylphosphites, triarylphosphites, and triarylphosphines; each organic moiety thereof having up to 18 carbon atoms; and said triorgano phosphorus ligand possessing a Δ HNP value of at least about 425; and (e) at least 2 moles of free ligand as defined above per mole of rhodium; (2) maintaining the reaction mixture at a temperature in the range of from about 50° C. to 145° C.; at a total pressure of carbon monoxide and hydrogen of less than 450 psia, and a partial pressure attributable to carbon monoxide no greater than about 75 percent of said total pressure; thereby (3) reacting said olefinic hydrocarbon with said carbon monoxide and hydrogen with the formation of said oxygenated products comprising aldehydes having a high normal/iso aldehyde ratio, the improvement which consists in including in said reaction mixture ethylene and additional carbon monoxide and hydrogen in amounts at least sufficient to react with said ethylene and reacting said ethylene with said carbon monoxide and hydrogen with the formation of propionaldehyde in addition to and concurrently with said oxygenated products comprising aldehydes having a high normal/iso aldehyde ratio.
Claim 3
Dependent Claim 28 words
A process as claimed in claim 1 wherein the ratio of ethylene to the olefinic hydrocarbon containing from 3 to 20 carbon atoms is from 0.1:1 to 10:1.
Claim 4
Dependent Claim 20 words
A process as claimed in claim 1 wherein the olefinic hydrocarbon containing from 3 to 20 carbon atoms is propylene.
Claim 5
Dependent Claim 20 words
A process as claimed in claim 1 wherein the olefinic hydrocarbon containing from 3 to 20 carbon atoms is butylene.
Claim 6
Dependent Claim 29 words
A process as claimed in claim 1 wherein the reaction of the ethylene and the propylene is conducted in high boiling liquid aldehyde condensation products formed during the reaction.

References Cited (Backward Citations)

GB1086100A Cited
GB1120277A Cited
US3527809A Cited
US3917661A Cited
BE821637A Cited
US4148830A Cited
US4143075A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-04-13 1984-10-13 1985-04-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-04-13 1988-10-13 1989-04-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-04-13 1992-10-13 1993-04-14 $7700.00 Window Closed / Lapsed

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