Formaldehyde → 2-Ethyl 2-(hydroxymethyl)hexanal

HRID 1885756Notes

Reaction equation

HRID 1885756 reaction equation
[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH:4]=[O:5])[CH3:2].[CH2:10]=[O:11]>C(N(CC)CC)C>[CH2:1]([C:3]([CH2:10][OH:11])([CH2:6][CH2:7][CH2:8][CH3:9])[CH:4]=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 312412-Ethylhexanal

Product 1

HCID 125384672-Ethyl 2-(hydroxymethyl)hexanal

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A one liter Parr autoclave was charged with 2-ethylhexanal (334 g, 406 mL, 2.6 mole), 44% aqueous formaldehyde (136.4 g, 122 mL, 2.0 mole) and varying amounts of triethylamine to determine the effect of increasing triethylamine concentration on reaction rate. After purging with nitrogen, the autoclave was sealed and heated at 100° C. for one hour. The autoclave was cooled and the contents were analyzed for formaldehyde (HCHO) by calorimetric analysis and for 2-ethyl2-(hydroxymethyl)hexanal (EHMH) by gas chromatography analysis. The yield of EHMH was calculated based on the 2-ethylhexanal consumed which was determined after correcting the gas chromatograph area for methanol and excess 2-ethylhexanal. Table I sets forth the amount of triethylamine (TEA, g/mL), the concentration by weight of triethylamine based on the total weight of the materials charged (TEA, %), the mole percent of formaldehyde converted (HCHO Conv.) and the percent yield of EHMH obtained.

Workup

  1. concentrationthe effect of increasing triethylamine concentration
  2. customon reaction rate
  3. customAfter purging with nitrogen
  4. customthe autoclave was sealed
  5. temperatureThe autoclave was cooled
  6. customconsumed which
  7. concentrationthe concentration by weight of triethylamine
  8. additioncharged (TEA, %)

Sources & evidence

ORD record
ord-74f401a3cb56486fbafbcfcfc7cd982f
Source dataset
uspto-grants-1992_09
Patent number
US05146004

Reaction notes

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