Pentaerythritol

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.

:[[File:Pentaerythritol Synthesis.svg|575px]]

Uses

Pentaerythritol is a versatile building block for the preparation of many compounds, particularly polyfunctionalized derivatives. applications include alkyd resins, varnishes, polyvinyl chloride stabilizers, tall oil esters, antioxidants (e.g. Anox 20). Such derivatives are found in plastics, paints, cosmetics, and many other products. Relevant to resins, pentaerythritol is a precursor to other polyol, such as dipentaerythritol: :

Esters of pentaerythitol are biodegradable, and they are used as transformer oils. Due to a very high flash point they also find some use in lubricating gas turbines.

Ester derivatives

Pentaerythritol is a precursor to esters of the type . Such derivatives are pentaerythritol tetranitrate (PETN), a vasodilator and explosive, the trinitrate derivative pentrinitrol (Petrin), the tetraacetate normosterol (PAG), and the polymer cross-linking agents pentaerythritol tetraacrylate and pentaerythritol tetrakis(3-mercaptopropionate).

A linear polymer which can be described as a (spiro) orthocarbonate ester of pentaerythritol, whose formula could be written as , was synthesized in 2002.

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.

References

References

1. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
2. (2010). "Handbook of aqueous solubility data". CRC Press.
3. (September 2019). "Production of Pentaerythritol Monoricinoleate (PEMR) by immobilized Candida antarctica lipase B". Biotechnology Reports.
4. {{PGCH. 0485
5. (1891). "Ueber den Penta-Erythrit, einen aus Formaldehyd und Acetaldehyd synthetisch hergestellten vierwerthigen Alkohol (On pentaerythritol, a quaternary alcohol synthetically produced from formaldehyde and acetaldehyde)". Justus Liebig's Annalen der Chemie.
6. Schurink, H. B. J.. (1925). "Pentaerythritol".
7. (1 August 1948). "The Chemical Reactions of Pentaerythritol and its Derivatives.". Chemical Reviews.
8. (2008). "Alcohols, Polyhydric".
9. (2016). "The Complete Book on Adhesives, Glues & Resins Technology (with Process & Formulations) 2nd Revised Edition".
10. (2005). "Synthetic Resins Technology Handbook".
11. (22 December 2005). "Synthetics, Mineral Oils, and Bio-Based Lubricants: Chemistry and Technology".
12. (28 December 2000). "Modern Tribology Handbook, Two Volume Set".
13. S. F. Marrian. (1948). "The Chemical Reactions of Pentaerythritol and its Derivatives". [[Chemical Reviews]].
14. (2010). "Thiol–Ene Click Chemistry". [[Angewandte Chemie International Edition]].
15. 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. {{doi. 10.1021/ja017683i
16. (2006). "Paints and Coatings".