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US4871879A Expired / Lapsed US ⏱️ 0.0 years remaining

Rhodium recovery from hydroformylation reaction product

Assignee: Oxea Corp
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Filing: 1987-10-27
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Granted: 1989-10-03
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Expires: 2007-10-27
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Abstract

Abstract In the hydroformylation of alkenes to aldehydes, rhodium is recovered from the stripped overhead of the hydroformylation reactor by condensing the overhead, removing the bulk of the aldehyde product from the condensed overhead, stripping the residue which remains with nitrogen gas to remove minor amounts of highly volatile aldehyde product remaining in the residue and redistilling the residue to remove components from the condensed overhead which are lower boiling than the catalyst components. The catalyst components including rhodium and phosphine ligand are returned to the hydroformylation reactor.

Inventors

  • 👤 Keith A. Laird

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 18:50
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/49; C07C45/50; Y; Y10; Y10S; Y10S203/00; Y10S203/06

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 237 words
In a process for catalytically hydroformylating propylene by the following steps: (a) reacting said propylene with carbon monoxide and hydrogen in the presence of a liquid reaction medium containing as the hydroformylation catalyst a complex of rhodium with a triorganophosphine to produce a liquid reaction mixture comprising triorganophosphine, butyraldehyde, and reaction by-products; (b) stripping said liquid reaction mixture by gas stripping, distillation, or evaporation during the course of said hydroformylation reaction to remove a vapor stream comprising said butyraldehyde and said hydroformylation catalyst overhead from said reaction mixture; (c) condensing said vapor stream and recovering a crude product condensate comprising said butyraldehyde; (d) distilling said condensate to form a distillate comprising the bulk of said butyraldehyde from said condensate and a residue comprising a crude reaction heavy ends mixture containing a minor amount of said butyraldehyde; and (e) distilling said crude reaction heavy ends mixture into (1) an overhead stream comprising those components of the crude reaction heavy ends mixture which are more volatile than said triorganophosphine and (2) a residue stream comprising those components of the crude reaction heavy ends mixture which are equal to or lower than said triorganophosphine in volatility and including any rhodium moiety initially contained in said vapor stream, the improvement which comprises: prior to step (e), stripping said residue containing said crude reaction heavy ends mixture obtained from step (d) with nitrogen gas to remove therefrom said minor amount of butyraldehyde.
Claim 2
Dependent Claim 237 words
In a process for catalytically hydroformylating propylene by the following steps: (a) reacting said propylene with carbon monoxide and hydrogen in the presence of a liquid reaction medium containing as the hydroformylation catalyst a complex of rhodium with a triorganophosphine to produce a liquid reaction mixture comprising triorganophosphine, butyraldehyde, and reaction by-products; (b) stripping said liquid reaction mixture by gas stripping, distillation, or evaporation during the course of said hydroformylation reaction to remove a vapor stream comprising said butyraldehyde and said hydroformylation catalyst overhead from said reaction mixture; (c) condensing said vapor stream and recovering a crude product condensate comprising said butyraldehyde; (d) distilling said condensate to form a distillate comprising the bulk of said butyraldehyde from said condensate and a residue comprising a crude reaction heavy ends mixture containing a minor amount of said butyraldehyde; and (e) distilling said crude reaction heavy ends mixture into (1) an overhead stream comprising those components of the crude reaction heavy ends mixture which are more volatile than said triorganophosphine and (2) a residue stream comprising those components of the crude reaction heavy ends mixture which are equal to or lower than said triorganophosphine in volatility and including any rhodium moiety initially contained in said vapor stream, the improvement which comprises: prior to step (e), stripping said residue containing said crude reaction heavy ends mixture obtained from step (d) with nitrogen gas to remove therefrom said minor amount of butyraldehyde.
Claim 3
Dependent Claim 16 words
The improvement of claim 1 wherein said liquid reaction medium comprises a high-boiling inert liquid solvent.
Claim 4
Dependent Claim 24 words
The improvement of claim 1 wherein the pressure during stripping said crude reaction heavy ends mixture ranges from about 1 to about 5 atmospheres.
Claim 5
Dependent Claim 16 words
The improvement of claim 3 wherein said pressure ranges from about 1 to about 2 atmospheres.
Claim 6
Dependent Claim 27 words
The improvement of claim 1 wherein said crude reaction heavy ends mixture is distilled at a temperature of between about 150° to 260° C. in step (c).
Claim 7
Dependent Claim 45 words
The improvement of claim 1 wherein said crude reaction heavy ends mixture is distilled in step (e) in a single pass operation wherein substantially all components of said crude reaction heavy ends mixture boiling lower than said triorganophosphine are removed overhead in a single step.
Claim 8
Dependent Claim 29 words
The improvement of claim 1 wherein said propylene is reacted with carbon monoxide and hydrogen at a temperature of about 80° C. to about 150° C. in step (a).
Claim 9
Dependent Claim 10 words
The improvement of claim 1 wherein said triorganophosphine is triphenylphosphine.
Claim 10
Dependent Claim 33 words
The method of claim 1 wherein said stripping of the residue containing said crude reaction heavy ends mixture is conducted in a packed column with countercurrent flow of said residue and nitrogen gas.
Claim 11
Dependent Claim 26 words
The method of claim 9 wherein said nitrogen gas is fed to said stripper at a rate of from about 15 to 200 pounds per hour.

References Cited (Backward Citations)

US1833717A Cited
US4199410A Cited
US4289589A Cited
US4479012A Cited
US4593127A Cited
US4613701A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-10-02 1993-04-03 1993-10-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-10-02 1997-04-03 1997-10-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-10-02 2001-04-03 2001-10-03 $7700.00 Window Closed / Lapsed

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