Pentaerythritol

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Pentaerythritol
Pentaerythritol.svg
Pentaerythritol-3D-balls.png
Names
Preferred IUPAC name
2,2-Bis(hydroxymethyl)propane-1,3-diol[1]
Other names
2,2-Bis(hydroxymethyl)1,3-propanediol
Pentaerythritol[1]
Hercules P 6
Monopentaerythritol
Tetramethylolmethane
THME
PETP
Pentaerythrite
Pentek
Hercules Aqualon improved technical PE-200
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.003.732
UNII
Properties
C5H12O4
Molar mass 136.15
Appearance white solid
Density 1.396g/cm3
Melting point 260.5 °C (500.9 °F; 533.6 K)
Boiling point 276 °C (529 °F; 549 K) at 30 mmHg
5.6 g/100 mL at 15 °C
Solubility Soluble in methanol, ethanol, glycerol, ethylene glycol, formamide; insoluble in acetone, benzene, paraffin, ether, CCl4
Vapor pressure 0.00000008 mmHg (20°C)[2]
Hazards
Flash point 200.1 °C (392.2 °F; 473.2 K)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp)[2]
REL (Recommended)
TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)[2]
IDLH (Immediate danger)
N.D.[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Pentaerythritol is an organic compound, a white, crystalline solid with the formula C5H12O4. It is a polyol with the neopentane backbone and one hydroxyl group in each of the four terminal carbons. It is a building block for the synthesis and production of explosives, plastics, appliances, and many other important chemicals.

History[edit]

Pentaerythritol was first synthesized in 1891 by German chemist Bernhard Tollens and his student P. Wigand.[3]

Uses[edit]

Pentaerythritol is a versatile building block for the preparation of many polyfunctionalized compounds, such as the explosive and vasodilator pentaerythritol tetranitrate (PETN) and the polymer cross-linking agent pentaerythritol tetraacrylate.[4] Derivatives of pentaerythritol are components of alkyd resins, varnishes, polyvinyl chloride stabilizers, tall oil esters, and olefin antioxidants. Can be found in transformer oil, plastics, and many other applications.

Medicine[edit]

Pentaerythritol is used to synthesize vasodilator pentaerythritol tetranitrate (PETN).

Explosive[edit]

Pentaerythritol is used to synthesize explosive pentaerythritol tetranitrate (PETN).

Dielectric[edit]

Halogen-free pentaerythritol esters are also environmentally friendly alternative to conventional electrical transformer fluids, being both readily biodegradable and non-hazardous in water. They advantageously replace polychlorobiphenyl (PCB), and even silicone-based or fluorinated hydrocarbons, as dielectric fluid in transformers. Their low volatility and high flash point give them an excellent resistance to ignition in case of major electrical failure and transformer rupture.

Fire retardant[edit]

Pentaerythritol is used as a fire retardant, such as in plastics.[5]

References[edit]

  1. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 691. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. 
  2. ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0485". National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ B. Tollens and P.Wigand (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), Annalen der Chemie, 265 : 316-340.
  4. ^ S. F. Marrian (1948). "The Chemical Reactions of Pentaerythritol and its Derivatives". Chemical Reviews. 43 (1): 149–202. doi:10.1021/cr60134a004. PMID 18876970. 
  5. ^ B. Pani; S. Sirohi; D. Singh (2013). "Studies on the Effects of Various Flame Retardants on Polypropylene". American Journal of Polymer Science.