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 (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.732 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-104-9
KEGG
PubChem CID
RTECS number
  • RZ2490000
UNII
  • InChI=1S/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2 X mark.svgN
    Key: WXZMFSXDPGVJKK-UHFFFAOYSA-N X mark.svgN
  • 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
Appearancewhite 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;

Contents

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).
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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]

Pentaerythritol Synthesis.svg

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]

See also

Related Research Articles

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<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

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<span class="mw-page-title-main">Butyraldehyde</span> Chemical compound

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<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)COOH. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Epichlorohydrin</span> Chemical compound

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References

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  4. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0485". National Institute for Occupational Safety and Health (NIOSH).
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  6. Schurink, H. B. J. (1925). "Pentaerythritol". Organic Syntheses . 4: 53. doi:10.15227/orgsyn.004.0053.; Collective Volume, vol. 1, p. 425
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  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.
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  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. 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.