Reuterin → 1,3-Propanediol

HRID 2394987Notes

Reaction equation

HRID 2394987 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]=[O:5].[H][H]>[Ni]>[CH2:4]([OH:5])[CH2:3][CH2:2][OH:1].[OH:5][CH2:4][CH2:3][CH:2]=[O:1]

Participants

5

Reactant 2

HCID 75049Reuterin4×HCID 178418361HCID 178418361, compound

Product 2

HCID 104421,3-PropanediolHCID 75049Reuterin

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

There is produced a solution containing 8.1 percent by weight of 3-hydroxypropanal and 1.3 percent by weight of dimerized 3-hydroxypropanal both obtained as the result of the above hydration reaction. A known raney nickel catalyst is added to the resulting solution to hydrogenate 3-hydroxypropanal and dimerized 3-hydroxypropanal. Reaction conditions are: a hydrogen pressure of 100 kg/cm2, a reaction temperature of 60° C., and reaction time of six hours. When the reaction ends, the resulting solution is analyzed and it is acknowledged that there is produced 1,3-propanediol in an amount equal to a total of 3-hydroxypropanal and dimerized 3-hydroxypropanal. In other words, 1,3-propanediol is quantitatively produced. This indicates that dimerized 3-hydroxypropanal is converted into 1,3-propanediol by a known hydrogenation process.

Workup

  1. customThere is produced a solution
  2. customboth obtained as the
  3. customresult of the above hydration reaction
  4. customReaction conditions

Sources & evidence

ORD record
ord-8926163e2626468d85b4e219bf4f940d
Source dataset
uspto-grants-1998_09
Patent number
US05811591

Reaction notes

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