Nonane → 2-Propylheptanoic acid

HRID 1401752

Reaction equation

HRID 1401752 reaction equation
[CH2:1]([CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[O:6])[CH2:2][CH3:3].CCCCCCCCC.CC(=[O:30])CCCCCCC>[Mn].[Cu]>[CH2:1]([CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:5]([OH:30])=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8141NonaneHCID 131872-NonanoneHCID 30186342-Propylheptanal3×

Product 1

HCID 357282-Propylheptanoic acid

Reagents, catalysts & solvents 1

HCID 11446311Copper, compd. with manganese (1:1)Catalyst

Procedure

As shown in Table 3, the conversion of the 2-propylheptanal oxidation was considerably improved in the presence of a homogeneous copper-manganese catalyst compared to the uncatalysed reaction. The residue contents of 2-propyl-heptanal of about 10.42% by mass determined after 4 hours in the presence of catalyst are lower than the corresponding residue contents of 24.71% by mass of 2-propylheptanal in the uncatalysed oxidation. However, the selectivity of the catalysed oxidation was significantly worse compared to the oxidation without catalyst. As can be seen from Table 3, column 3, the selectivity in the homogeneously catalysed oxidation was reduced by the formation of by-products such as nonane and nonanone. As a result, the yield of isomeric decanecarboxylic acids is comparable to the yield in the uncatalysed oxidation despite higher conversions of about 55% by mass of 2-propylheptanoic acid.

Workup

  1. customcompared to the uncatalysed reaction

Sources & evidence

ORD record
ord-3aa51f19da4d452a89d2cb4303953da6
Source dataset
uspto-grants-2014_12
Patent number
US08907129B2

Linked notes

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