Pentaerythritol

Pentaerythritol
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
CAS Number	115-77-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:134760;
ChEMBL	ChEMBL3186112;
ChemSpider	7984 ;
DrugBank	DB13526;
ECHA InfoCard	100.003.732
EC Number	204-104-9;
KEGG	D08331;
PubChem CID	8285;
RTECS number	RZ2490000;
UNII	SU420W1S6N ;
CompTox Dashboard (EPA)	DTXSID2026943 ;
	InChI InChI=1S/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2 Key: WXZMFSXDPGVJKK-UHFFFAOYSA-N ; InChI=1/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2 Key: WXZMFSXDPGVJKK-UHFFFAOYAH;
	SMILES OCC(CO)(CO)CO;
Properties
Chemical formula	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
Solubility in water	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)
	NIOSH (US health exposure limits):
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).
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	Infobox references

Pentaerythritol is an organic compound with the formula C(CH₂OH)₄. Classified as a polyol, it is a white solid. Pentaerythritol is a building block for the synthesis and production of explosives, plastics, paints, appliances, cosmetics, and many other commercial products.

The word pentaerythritol is a blend of penta- in reference to its 5 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.[3] It may be prepared via a base-catalyzed multiple-addition reaction between acetaldehyde and 3 equivalents of formaldehyde, followed by a Cannizzaro reaction with a fourth equivalent of formaldehyde to give the final product.[4]

Uses

Pentaerythritol is a versatile building block for the preparation of many polyfunctionalized compounds. Derivatives of pentaerythritol are components of alkyd resins, varnishes, polyvinyl chloride stabilizers, tall oil esters, antioxidants (e.g. Anox 20). It can be found in transformer oil, plastics, paints, cosmetics, and many other applications.[5][6]

Polyester derivatives

Pentaerythritol is a precursor to esters of the type C(CH₂OX)₄. One such derivative is pentaerythritol tetranitrate (PETN), a vasodilator and explosive. The trinitrate derivative is called pentrinitrol (Petrin). The tetraacetate is called normosterol (PAG). The polymer cross-linking agent pentaerythritol tetraacrylate.[7]

Fire retardants

Pentaerythritol is used as a fire retardant, such as in plastics. It produces a thick carbon barrier upon heating, protecting the surface substrate.

Pentaerythritol is one of the most common main active components in intumescent paints and coatings. It acts as a carbon donor and together with an acid donor, most commonly ammonium polyphosphate (APP), and a blowing agent, most commonly melamine.

References

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.
NIOSH Pocket Guide to Chemical Hazards. "#0485". National Institute for Occupational Safety and Health (NIOSH).
Tollens, B.; Wigand, P. (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 (in German). 265 (3): 316–340. doi:10.1002/jlac.18912650303.
Schurink, H. B. J. (1925). "Pentaerythritol". Organic Syntheses. 4: 53. doi:10.15227/orgsyn.004.0053.; Collective Volume, 1, p. 425
NPCS Board of Consultants & Engineers (2016). The Complete Book on Adhesives, Glues & Resins Technology (with Process & Formulations) 2nd Revised Edition.
NIIR Board of Engineers & Consultants (2005). Synthetic Resins Technology Handbook.
S. F. Marrian (1948). "The Chemical Reactions of Pentaerythritol and its Derivatives". Chemical Reviews. 43 (1): 149–202. doi:10.1021/cr60134a004. PMID 18876970.

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[iupac2013-1] 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.

[PGCH-2] NIOSH Pocket Guide to Chemical Hazards. "#0485". National Institute for Occupational Safety and Health (NIOSH).

[3] Tollens, B.; Wigand, P. (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 (in German). 265 (3): 316–340. doi:10.1002/jlac.18912650303.

[Schurink1941-4] Schurink, H. B. J. (1925). "Pentaerythritol". Organic Syntheses. 4: 53. doi:10.15227/orgsyn.004.0053.; Collective Volume, 1, p. 425

[5] NPCS Board of Consultants & Engineers (2016). The Complete Book on Adhesives, Glues & Resins Technology (with Process & Formulations) 2nd Revised Edition.

[6] NIIR Board of Engineers & Consultants (2005). Synthetic Resins Technology Handbook.

[7] S. F. Marrian (1948). "The Chemical Reactions of Pentaerythritol and its Derivatives". Chemical Reviews. 43 (1): 149–202. doi:10.1021/cr60134a004. PMID 18876970.