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Pentaerythritol

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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.732 Edit this at Wikidata
EC Number
  • 204-104-9
KEGG
RTECS number
  • RZ2490000
UNII
  • 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
  • OCC(CO)(CO)CO
Properties
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
  • 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

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 checkY☒N ?)

Pentaerythritol is an organic compound with the formula C(CH2OH)4. The molecular structure can be described as a neopentane with one hydrogen atom in each methyl group replaced by a hydroxyl (–OH) group. It is therefore a polyol, specifically a tetrol.

Pentaerythritol is a white solid. It 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 five carbon atoms and erythritol, which also possesses 4 alcohol groups.

Synthesis

[edit]

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

[edit]

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]

Ester derivatives

[edit]

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]

A linear polymer which can be described as a (spiro) orthocarbonate ester of pentaerythritol, whose formula could be written as [(−CH2)2C(CH2−)2 (−O)2C(O−)2]n, was synthesized in 2002.[15]

Fire retardants

[edit]

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.[16]

See also

[edit]

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. ^ 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.
  4. ^ a b c d 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)" (PDF). Justus Liebig's Annalen der Chemie (in German). 265 (3): 316–340. doi:10.1002/jlac.18912650303.
  6. ^ Schurink, H. B. J. (1925). "Pentaerythritol". Organic Syntheses. 4: 53. doi:10.15227/orgsyn.004.0053; Collected Volumes, 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. ISBN 978-3527306732.
  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. ^ Hoyle, Charles E.; Bowman, Christopher N. (2010). "Thiol–Ene Click Chemistry". Angewandte Chemie International Edition. 49 (9): 1542–1543. doi:10.1002/anie.200903924.
  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. ^ 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 3527306730.
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