Acetophenone → Propylene Glycol

HRID 1904172Notes

Reaction equation

HRID 1904172 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:10]([OH:14])[CH:11]([OH:13])[CH3:12].C(C1C=CC=CC=1)(=O)C>>[CH2:10]([OH:14])[CH:11]([OH:13])[CH3:12].[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7410Acetophenone2×HCID 70391103HCID 70391103, compound

Product 2

HCID 1030Propylene GlycolHCID 7410Acetophenone

Procedure

Forty grams of m-DIPB-p-DIPB mixture and 40 grams of acetophenone were charged to an Othmer type vapor liquid equilibrium still and refluxed for six hours. The azeotrope boiled at 191° C. (640 mm) and contained about 60% acetophenone. Both the vapor and liquid portions from the vapor-liquid equilibrium still were then extracted with propylene glycol at room temperature. Two liquid phases were obtained. The hydrocarbon phase was analysed by gas chromatography which gave a vapor composition of 69.5% m-DIPB, 30.5% p-DIPB and a liquid composition of 61.1% m-DIPB, 38.9% p-DIPB. This is a relative volatility of m-DIPB to p-DIPB of 1.45. The propylene glycol-acetophenone liquid phase was rectified and gave propylene glycol at 181° C. as overhead and acetophenone boiling at 194° C. as bottoms. Both were ready for recycle.

Workup

  1. temperaturerefluxed for six hours
  2. extractionBoth the vapor and liquid portions from the vapor-liquid equilibrium still were then extracted with propylene glycol at room temperature
  3. customTwo liquid phases were obtained
  4. customgave a vapor composition of 69.5% m-DIPB, 30.5% p-DIPB

Sources & evidence

ORD record
ord-6db5bb257b13497680be64e806701410
Source dataset
uspto-grants-1989_06
Patent number
US04836896

Reaction notes

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