Acetic Acid → 3-Hexanone

HRID 359604Notes

Reaction equation

HRID 359604 reaction equation
[C:1](O)(=O)[CH3:2].[C:5]([OH:10])(=O)[CH2:6][CH2:7][CH3:8].[CH2:11]([C:13]([CH3:15])=O)[CH3:12]>[O-2].[O-2].[Mn+4]>[CH2:12]([C:5]([CH2:6][CH2:7][CH3:8])=[O:10])[CH2:11][CH2:13][CH3:15].[CH2:6]([C:5]([CH2:1][CH3:2])=[O:10])[CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 264Butyric AcidHCID 6569Methyl Ethyl Ketone

Product 2

HCID 115093-HexanoneYield 60%HCID 11516Octan-4-oneYield 24%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

Kirk-Othmer i.b.i.d. discloses that unsymmetrical dialkyl ketones are prepared by passing vapors of two different fatty acids over an alkaline earth oxide at elevated temperatures. It is stated that the product necessarily contains the three possible ketones and in the example given a mixture of acetic acid and butyric acid are reacted in the vapor phase at 300° C. on a manganese dioxide catalyst to produce 16% methyl ethyl ketone, 24% propyl butyl ketone and 60% ethyl propyl ketone.

Workup

  1. customare prepared

Sources & evidence

ORD record
ord-6b7a825e77f247169c607f37de29cc58
Source dataset
uspto-grants-1991_03
Patent number
US05001273

Reaction notes

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