Formic Acid → 1,2-Dodecanediol

HRID 132090

Reaction equation

HRID 132090 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]C.[CH:13]([OH:15])=O.OO.CO.S(=O)(=O)(O)[OH:21]>>[CH2:13]([OH:15])[CH:11]([OH:21])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

6

Reactant 5

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 887MethanolHCID 1118Sulfuric AcidHCID 81831-Dodecene

Product 1

HCID 928661,2-Dodecanediol

Conditions

Temperature
100 °C

Procedure

168.3 g (1.0 mol) of 1-dodecene and 73.6 g (1.6 mol) of formic acid were mixed. This mixture was heated to 100° C. and then 115.7 g (1.7 mol) of 50% strength hydrogen peroxide solution were added dropwise over a period of 2 hours. The mixture was then stirred at 100° C. for 45 min. 64.1 g (2 mol) of methanol and 0.1 g of concentrated sulfuric acid were added, and the mixture was heated under reflux for 30 min and then the methyl formate, methanol and water were removed by distillation under atmospheric pressure. A >99% pure main fraction was isolated after the subsequent workup by distillation. The freshly distilled target product had an unpleasant, pungent odor.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. customthe methyl formate, methanol and water were removed by distillation under atmospheric pressure
  4. customA >99% pure main fraction was isolated after the subsequent workup
  5. distillationby distillation

Sources & evidence

ORD record
ord-9dc05daf695845eabce1908a2ae43efe
Source dataset
uspto-grants-2008_06
Patent number
US07385092B2

Linked notes

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