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 g/mol
Appearance	white solid
Density	1.396 g/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	38.46 g/L (0°C); 47.62 g/L (10°C); 52.60 g/L (15°C); 56.60 g/L (20°C); 74.07 g/L (30°C); 115.0 g/L (40°C); 180.3 g/L (60°C); 285.7 g/L (80°C); 500.0 g/L (100°C)[2];
Solubility	TBuOH, 15g/L (60°C)[3]; DMSO, 20g/L (25°C); Slightly soluble in:methanol, ethanol, glycerol, ethylene glycol, formamide; insoluble in: acetone, toluene, heptane, diethyl ether, dichloromethane
Vapor pressure	0.00000008 mmHg (20°C)[4]
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)[4]
REL (Recommended)	TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)[4]
IDLH (Immediate danger)	N.D.[4]
Related compounds
Related compounds	Neopentane, Neopentyl alcohol, Neopentyl glycol, Trimethylolethane, Orthocarbonic acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.[5] 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.[6]

Uses

Pentaerythritol is a versatile building block for the preparation of many compounds,[7] 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.[8]

Esters of pentaerythitol are biodegradable,[9][10] and they are used as transformer oils.[11] Due to a very high flash point they also find some use in lubricating gas turbines.[12]

Polyester derivatives

Pentaerythritol is a precursor to esters of the type C(CH₂OX)₄. Such derivatives are pentaerythritol tetranitrate (PETN), a vasodilator and explosive, the trinitrate derivative pentrinitrol (Petrin), the tetraacetate normosterol (PAG), and the polymer cross-linking agent pentaerythritol tetraacrylate.[13]

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.[14]

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.
Yalkowsky, Samuel H. (2010). Handbook of aqueous solubility data (Second ed.). Boca Raton, FL: CRC Press. p. 185. ISBN 9781439802465.
Yadav, Manish G.; Vadgama, Rajeshkumar N.; Kavadia, Monali R.; Odaneth, Annamma Anil; Lali, Arvind M. (September 2019). "Production of Pentaerythritol Monoricinoleate (PEMR) by immobilized Candida antarctica lipase B". Biotechnology Reports. 23: e00353. doi:10.1016/j.btre.2019.e00353. PMC 6599945. PMID 31304100.
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, vol. 1, p. 425
Marrian, S. F. (1 August 1948). "The Chemical Reactions of Pentaerythritol and its Derivatives". Chemical Reviews. 43 (1): 149–202. doi:10.1021/cr60134a004. PMID 18876970.
Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2.
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.
Rudnick, Leslie R. (22 December 2005). Synthetics, Mineral Oils, and Bio-Based Lubricants: Chemistry and Technology. ISBN 9781420027181.
Bhushan, Bharat (28 December 2000). Modern Tribology Handbook, Two Volume Set. ISBN 9780849377877.
S. F. Marrian (1948). "The Chemical Reactions of Pentaerythritol and its Derivatives". Chemical Reviews. 43 (1): 149–202. doi:10.1021/cr60134a004. PMID 18876970.
Stoye, Dieter; et al. (2006). "Paints and Coatings". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a18_359.pub2.

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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.

[2] Yalkowsky, Samuel H. (2010). Handbook of aqueous solubility data (Second ed.). Boca Raton, FL: CRC Press. p. 185. ISBN 9781439802465.

[3] Yadav, Manish G.; Vadgama, Rajeshkumar N.; Kavadia, Monali R.; Odaneth, Annamma Anil; Lali, Arvind M. (September 2019). "Production of Pentaerythritol Monoricinoleate (PEMR) by immobilized Candida antarctica lipase B". Biotechnology Reports. 23: e00353. doi:10.1016/j.btre.2019.e00353. PMC 6599945. PMID 31304100.

[PGCH-4] NIOSH Pocket Guide to Chemical Hazards. "#0485". National Institute for Occupational Safety and Health (NIOSH).

[5] 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.

[Schurink1941-6] Schurink, H. B. J. (1925). "Pentaerythritol". Organic Syntheses. 4: 53. doi:10.15227/orgsyn.004.0053.; Collective Volume, vol. 1, p. 425

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

[8] Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2.

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

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

[11] Rudnick, Leslie R. (22 December 2005). Synthetics, Mineral Oils, and Bio-Based Lubricants: Chemistry and Technology. ISBN 9781420027181.

[12] Bhushan, Bharat (28 December 2000). Modern Tribology Handbook, Two Volume Set. ISBN 9780849377877.

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

[14] Stoye, Dieter; et al. (2006). "Paints and Coatings". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a18_359.pub2.