Butanal → Trimethylolpropane

HRID 2217078Notes

Reaction equation

HRID 2217078 reaction equation
C(=O)CCC.C=O.[CH2:8]([C:10]([CH2:15][OH:16])([CH2:13][CH3:14])[CH:11]=[O:12])[OH:9]>C(O)=O>[CH2:8]([C:10]([CH2:15][OH:16])([CH2:11][OH:12])[CH2:13][CH3:14])[OH:9]

Participants

5

Reactant 3

HCID 261ButanalHCID 712Formaldehyde2×HCID 110516932,2-dimethylolbutanal

Product 1

HCID 6510Trimethylolpropane

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In the Cannizzaro process, butyraldehyde is reacted with formaldehyde in the presence of a stoichiometric amount of base. This initially forms 2,2-dimethylolbutanal which then reacts with a further molecule of formaldehyde in a cross-Cannizzaro reaction to form formic acid and trimethylolpropane. The disadvantage of this method is that one molar equivalent of formate is formed as coproduct. This has to be worked up and increases the consumption of formaldehyde.

Sources & evidence

ORD record
ord-6aa0d5f8ece7413e94ed676c01255609
Source dataset
uspto-grants-2006_09
Patent number
US07112707B2

Reaction notes

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