PENTAERYTHRITOL DERIVATIVES: I.MECHANISM OF FORMATION OF DIPENTAERYTHRITOL
- 1 March 1963
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 41 (3) , 770-776
- https://doi.org/10.1139/v63-109
Abstract
Dipentaerythritol, (CH2OH)3CCH2OCH2C(CH2OH)3, is a product of the base-catalyzed Tollens condensation of acetaldehyde with formaldehyde. The mechanism for formation of dipentaerythritol has not been hitherto established.Three types of experimental evidence support the conclusion that monopentaerythritol, C(CH2OH)4, is an intermediate in the sequence of reactions leading to dipentaerythritol: (1) the isolation of radioactive dipentaerythritol from a Tollens condensation in which mono-pentaerythritol-C14 was present, (2) comparison of the radioactivity levels of mono- and di-pentaerythritol prepared by reaction of formaldehyde-C14 with inactive monopentaery-thritol and inactive acetaldehyde, and (3) the observed dependence of the yield of dipentaerythritol on the concentration of monopentaerythritol present in the condensation reaction mixture.Keywords
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