Benzoic Acid → 1-Phenyl-1-propanone

HRID 426902

Reaction equation

C(O)(=O)CC.C(O)(=O)C1C=CC=CC=1.O.[C:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])[CH:17](C)[CH3:18]>>[C:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])[CH2:17][CH3:18]

Participants

Reactant 4

HCID 243Benzoic Acid2×

HCID 962Water

HCID 1032Propionic Acid

HCID 69144Isobutyrophenone

Product 1

HCID 71481-Phenyl-1-propanoneYield 2,360.1%

Procedure

In Example 1, using the reactor described above, together with ancillary equipment, a mixture containing 2 moles of propionic acid per mole of benzoic acid was fed to the reactor together with 4 moles of water per mole of benzoic acid at a rate of 249 ml/hr. for 4.5 hours. The reaction temperature was maintained between 445° C. and 450° C. Analysis of the condensed organic layer by gas chromatography indicated that 4.68 pounds of isobutyrophenone were produced per 100 pounds of propiophenone. These data are delineated in Table I. The instrument used was a Bendix Model 2300 dual column programmed temperature gas chromatograph having a thermal conductivity detector. The bridge current was 200 ma. with a 0-1 mv. recorder. The column consisted of two, 10 feet by 1/8 inch stainless steel tubing packed with silicone on an inert support. The column temperature was 190° C. The carrier gas was helium at 30 cc/minute.

Workup

temperatureThe reaction temperature was maintained between 445° C. and 450° C

Sources & evidence

ORD record: ord-063298aeb3d64e87a52b5597fe35919b
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04172097

Linked notes

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