Acetone → HCID 23616661, compound

HRID 968081Notes

Reaction equation

HRID 968081 reaction equation
CC(C[O-:5])C.[K+].[C:7]1([CH3:14])[C:8](C)=[CH:9]C=C[CH:12]=1.[CH3:15][C:16]([CH3:18])=[O:17].C#C>O>[CH3:12][CH:7]([CH2:8][CH3:9])[C:14]#[C:15][C:16]([CH3:18])([OH:5])[OH:17]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6326AcetyleneHCID 86759880HCID 86759880, compound

Product 1

HCID 23616661HCID 23616661, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

529 g of a potassium isobutoxide/xylene suspension (4.5 mol/kg), 127 g of acetone and 29 g of acetylene gas were metered continuously and synchronously over a period of one hour into a reaction mixing pump having a nominal capacity of 20 ml. The reaction mixture which was mixed very well in the reaction pump was conveyed via a pump circuit in which a heat exchanger was located. The reaction temperature in the pump was 35° C., that upstream of the heat exchanger was 32° C. and that downstream of the heat exchanger was 28° C. The volume flow in the pumped circuit was in the range from 80 to 100 l/h. From the pump circuit, an after-reaction section led to a hydrolysis vessel where the reaction mixture was hydrolyzed by means of 500 g/h of water. After the organic phase had been separated off and neutralized by means of 22.8 g of phosphoric acid, dimethylhexynediol was obtained at a conversion of 98% and in a yield of 90%. Methylbutynol in a yield of 2.3% was identified as by-product.

Workup

  1. additionmixing pump
  2. additionThe reaction mixture which was mixed very well in the reaction pump
  3. customwas 35° C.
  4. customwas 32° C.
  5. customwas 28° C
  6. customFrom the pump circuit, an after-reaction section led to a hydrolysis vessel
  7. customAfter the organic phase had been separated off

Sources & evidence

ORD record
ord-73102215e8fd42b180f09ae5c396cfce
Source dataset
uspto-grants-2005_10
Patent number
US06956141B1

Reaction notes

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