Acetaldehyde → Formate

Participants

Reaction Steps

Pentaerythritol[2,2-bis(hydroxymethyl)-1,3-propane diol, Penta, PE] is a white, crystalline powder with a sweet taste and is neither hygroscopic nor inflammable, density 1.399, melting point 262° C. and boiling point 276° C. (40 hPa). Pentaerythritol is highly soluble in boiling water, is poorly soluble in alcohol, and insoluble in benzene, tetrachloromethane, ether, petroleum ether. Pentaerythritol is manufactured industrially by reacting formaldehyde with acetaldehyde in an aqueous solution of Ca(OH)2 or NaOH at 15-45° C. The reaction takes place initially as an aldol reaction, whereby the formaldehyde reacts as the carbonyl component and the acetaldehyde as the methylene component. Due to the high carbonyl activity of the formaldehyde, the reaction of acetaldehyde with itself hardly occurs. Finally, the tris(hydroxymethyl)acetaldehyde undergoes a crossed Cannizzaro reaction with formaldehyde to afford pentaerythritol and formate.

Provenance & Evidence