Tributylphosphine → HCID 86738217, compound

HRID 1106137Notes

Reaction equation

C(P(CCCC)CCCC)CCC.[CH2:14]([CH:17]([CH2:20][CH2:21][CH3:22])[CH:18]=[O:19])[CH2:15][CH3:16].[CH2:23]([CH:25]([CH2:28][CH2:29][CH2:30][CH3:31])[CH:26]=[O:27])[CH3:24]>>[CH2:14]([CH:17]([CH2:20][CH2:21][CH3:22])[CH:18]=[O:19])[CH2:15][CH3:16].[CH2:23]([CH:25]([CH2:28][CH2:29][CH2:30][CH3:31])[CH:26]=[O:27])[CH3:24]

Participants

Reactant 3

HCID 13831Tributylphosphine

HCID 312412-Ethylhexanal

HCID 875602-Propylvaleraldehyde

Product 1

HCID 86738217HCID 86738217, compound

Conditions

Temperature: 130 °C

Procedure

Into an autoclave are charged 294.6 g (=420 ml, 3 moles) of heptene-3, 50 ppm of Rh (based on heptene-3) in the form of RhCl3, and 2.8 g of tributyl phosphine (molar ratio of Rh:phosphine=1:100). A pressure of 150 bars is adjusted by introducing CO and H2 (molar ratio, 1:1). Thereafter, the temperature is increased to 130° C. and the pressure to 290 bars. After 3 hours, the olefin is reacted quantitatively. As is shown by the analysis by gas chromatography, the reaction product contains 2-propyl pentanal and 2-ethyl hexanal in a ratio of about 75:25. The yield (2-propyl pentanal+2-ethyl hexanal) is 346 g. The hydroformylation product is directly oxidized after flash distillation.

Workup

additionby introducing CO and H2 (molar ratio, 1:1)

Sources & evidence

ORD record: ord-407009479ac842afb28349e0c39310f6
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04311854

Reaction notes

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