Propionic Acid → Nonanoic Acid

HRID 361951Notes

Reaction equation

[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6]CC.[C:9]([OH:13])(=[O:12])[CH2:10][CH3:11]>O>[C:9]([OH:13])(=[O:12])[CH2:10][CH2:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 100 °C

Procedure

An autoclave was charged with 0.1 g of Rh(acac)(CO)2, 20 g of pyridineand 10 g of 1-octene in a mixture of 60 g of propionic acid and 10 g of water as solvent. A pressure of 30 bar was set using CO and the mixture was heated to 100° C. A reaction pressure of 100 bar was then set by injecting CO and was maintained by injection of further amounts (every 15 minutes). After 1 hour, the autoclave was depressurized and the reaction mixture produced was analyzed titrimetrically and by gas chromatography. Nonanoic acid (n/iso 2.6:1) was formed in an STY of 46 g/l/h (Sel.>95%). Nonanal (n/iso) could be detected in traces by gas chromatography. Hydrogenation products such as octane or nonanol were not found.

Workup

customA reaction pressure of 100 bar
temperaturewas maintained by injection of further amounts (every 15 minutes)
customthe reaction mixture produced

Sources & evidence

ORD record: ord-1224594824fc4ff88ca9b2a1aacbe218
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866716

Reaction notes

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