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US4230641A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydroformylation of olefins

Assignee: Air Products and Chemicals Inc
•
Filing: 1977-11-21
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Granted: 1980-10-28
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Expires: 1997-11-21
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Abstract

Abstract This invention relates to an improvement in a process for the hydroformylation of olefins, e.g. propylene to form saturated aldehydes. The improvement comprises reacting the olefin with carbon monoxide in the presence of a catalyst comprising a complex of a chelating phosphine ligand and a rhodium compound.

Inventors

  • 👤 Charles M. Bartish

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 23:45
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/49; C07C45/50

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 212 words
In a hydroformylation process, wherein a C 2-20 monounsaturated alpha-olefin, carbon monoxide, and hydrogen are reacted in the presence of a catalyst comprising a complex of a phosphine ligand and rhodium to produce normal straight chain and iso saturated aldehyde isomers, at a pressure from 100-1,000 psi, the improvement for producing a high normal/iso isomer ratio and without forming sparingly soluble catalyst complexes, which comprises effecting said reaction in the presence of a catalyst comprising a complex of a rhodium compound and chelating phosphine ligand, the chelating phosphine ligand being represented by the formula: R 1 R 2 P A P R 3 R 4 wherein: R 1 and R 3 are alkenyl groups having from 2 to 6 carbon atoms, alkyl groups having from 1 to 6 carbon atoms, hydrogen atoms, phenyl groups, and substituted derivatives thereof; R 2 and R 4 are phenyl groups and substituted phenyl groups; A is an alkenyl group having from 2 to 4 carbon atoms; and (CH 2 ) n wherein n is from 2 to 10 and substituted derivatives thereof; and the molar ratio of said ligand to rhodium is from about 0.6-1.2:1 provided that where A is (CH 2 ) n and n is from 5-10, then the molar ratio is from 1-5:1.
Claim 2
Dependent Claim 212 words
In a hydroformylation process, wherein a C 2-20 monounsaturated alpha-olefin, carbon monoxide, and hydrogen are reacted in the presence of a catalyst comprising a complex of a phosphine ligand and rhodium to produce normal straight chain and iso saturated aldehyde isomers, at a pressure from 100-1,000 psi, the improvement for producing a high normal/iso isomer ratio and without forming sparingly soluble catalyst complexes, which comprises effecting said reaction in the presence of a catalyst comprising a complex of a rhodium compound and chelating phosphine ligand, the chelating phosphine ligand being represented by the formula: R 1 R 2 P A P R 3 R 4 wherein: R 1 and R 3 are alkenyl groups having from 2 to 6 carbon atoms, alkyl groups having from 1 to 6 carbon atoms, hydrogen atoms, phenyl groups, and substituted derivatives thereof; R 2 and R 4 are phenyl groups and substituted phenyl groups; A is an alkenyl group having from 2 to 4 carbon atoms; and (CH 2 ) n wherein n is from 2 to 10 and substituted derivatives thereof; and the molar ratio of said ligand to rhodium is from about 0.6-1.2:1 provided that where A is (CH 2 ) n and n is from 5-10, then the molar ratio is from 1-5:1.
Claim 3
Dependent Claim 13 words
The process of claim 1 wherein A is (CH 2 ) n .
Claim 4
Dependent Claim 14 words
The process of claim 1 wherein said olefin has from about 3-8 carbon atoms.
Claim 5
Dependent Claim 14 words
The process of claim 1 wherein R 1 and R 3 are phenyl groups.
Claim 6
Dependent Claim 14 words
The process of claim 4 wherein R 2 and R 4 are phenyl groups.
Claim 7
Dependent Claim 26 words
The process of claim 5 wherein the molar concentration of rhodium employed is from about 1×10 -6 to 1×10 -2 as metal per mole of olefin.
Claim 8
Dependent Claim 24 words
The process of claim 6 wherein the molar concentration of ligand to rhodium is from about 0.9 to 1.1:1 and n is from 2-4.
Claim 9
Dependent Claim 31 words
The process of claim 5 wherein R 1 , R 2 , R 3 and R 4 are substituted with substituent groups selected from the group consisting of methyl and fluoro.
Claim 10
Dependent Claim 29 words
The process of claim 5 wherein said ligand is selected from the group consisting of bis(diphenylphosphino) alkanes having from 2-10 carbon atoms, 1,2-bis(bispentafluorophenylphosphino) ethane, 1,2-bis(di-O-tolylphosphino) ethane, and 1,2-bis[(bisdimethylphenylphosphino)] ethane.

References Cited (Backward Citations)

US3168553A Cited
US3555098A Cited
US3647842A Cited
US4139565A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-10-28 1984-04-28 1984-10-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-10-28 1988-04-28 1988-10-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-10-28 1992-04-28 1992-10-28 $7700.00 Window Closed / Lapsed

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