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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:134760
ChEMBL	ChEMBL3186112
ChemSpider	7984^Y
DrugBank	DB13526
ECHA InfoCard	100.003.732
EC Number	204-104-9
KEGG	D08331
PubChem CID	8285
RTECS number	RZ2490000
UNII	SU420W1S6N^Y
CompTox Dashboard (EPA)	DTXSID2026943
InChI InChI=1S/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2^N Key: WXZMFSXDPGVJKK-UHFFFAOYSA-N^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). N verify (what is ^YN ?) 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.

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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 agents pentaerythritol tetraacrylate and pentaerythritol tetrakis(3-mercaptopropionate).^[13]^[14]

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.^[15]

References

^ ^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.
^ 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.
^ ^a ^b ^c ^d 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)" (PDF). 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; Collected Volumes, 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. ISBN 978-3527306732.
^ 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.
^ Hoyle, Charles E.; Bowman, Christopher N. (2010). "Thiol–Ene Click Chemistry". Angewandte Chemie International Edition. 49 (9): 1542–1543. doi:10.1002/anie.200903924.
^ Stoye, Dieter; et al. (2006). "Paints and Coatings". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a18_359.pub2. ISBN 978-3527306732.

This page was last edited on 13 May 2024, at 16:26

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