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Benzoic Acid → 1-Phenyl-1-propanone

HRID 426902
Notes
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Reaction equation

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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 243Benzoic Acid2×HCID 962WaterHCID 1032Propionic AcidHCID 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

  1. 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

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes