Pentaerythritol is an organic compound with the chemical formula C(CH2OH)4. The molecular structure can be described as a neopentane with one hydrogen atom in each methyl group replaced by a hydroxyl (–OH) group. It is therefore a polyol, specifically a tetrol.
Pentaerythritol is a white solid. It is a building block for the synthesis and production of , , , home appliance, cosmetics, and many other commercial products.
The word pentaerythritol is a blend of penta- in reference to its five carbon atoms and erythritol, which also possesses 4 alcohol groups.
Synthesis
Pentaerythritol was first reported in 1891 by German chemist
Bernhard Tollens and his student P. Wigand.
It may be prepared via a base-catalyzed multiple-addition reaction between
acetaldehyde and 3 equivalents of
formaldehyde to give
pentaerythrose (CAS: 3818-32-4), followed by a Cannizzaro reaction with a fourth equivalent of
formaldehyde to give the final product plus
formate ion.
Uses
Pentaerythritol is a versatile building block for the preparation of many compounds,
particularly polyfunctionalized derivatives. applications include
alkyd ,
, polyvinyl chloride stabilizers,
tall oil ,
(e.g. Anox 20). Such derivatives are found in
,
,
cosmetics, and many other products. Relevant to resins, pentaerythritol is a precursor to other
polyol, such as dipentaerythritol:
of pentaerythitol are biodegradable,
Ester derivatives
Pentaerythritol is a precursor to esters of the type C(CH
2OX)
4. Such derivatives are pentaerythritol tetranitrate (PETN), a
vasodilator and
explosive, the trinitrate derivative
pentrinitrol (Petrin), the tetraacetate
normosterol (PAG), and the
Cross-link pentaerythritol tetraacrylate and pentaerythritol tetrakis(3-mercaptopropionate).
A linear polymer which can be described as a (spiro compound) orthocarbonate ester of pentaerythritol, whose formula could be written as , was synthesized in 2002.[David T. Vodak, Matthew Braun, Lykourgos Iordanidis, Jacques Plévert, Michael Stevens, Larry Beck, John C. H. Spence, Michael O'Keeffe, Omar M. Yaghi (2002): "One-Step Synthesis and Structure of an Oligo(spiro-orthocarbonate)". Journal of the American Chemical Society, volume 124, issue 18, pages 4942–4943. ]
Fire retardants
Pentaerythritol is used as a fire retardant, such as in plastics and
intumescent paints and coatings. It releases water upon heating and leaves a deposit of thermally insulating char.
See also
