Pentaerythritol

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Pentaerythritol
IUPAC name 2,2-Bis(hydroxymethyl)1,3-propanediol
Other names Hercules P 6, monopentaerythritol, tetramethylolmethane, THME, PETP, pentaerythrite, Pentek, Hercules Aqualon improved technical PE-200
Identifiers
CAS number [115-77-5]
Properties
Molecular formula C(CH2OH)4
Molar mass 136.15
Appearance white solid
Melting point

260.5 °C
Boiling point

276 °C at 30 mmHg
Solubility in water 5.6 g/100 mL at 15°C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Pentaerythritol is the organic compound with the formula C(CH2OH)4. This white, crystalline polyol is a versatile building block for the preparation of many polyfunctionalized compounds such as the explosive PETN and pentaerythritol triacrylate[1]. Derivatives of pentaerythritol are components of alkyd resins, varnishes, PVC stabilizers, tall oil esters, and olefin antioxidants.

[edit] Preparation

It can be prepared by condensation of acetaldehyde and formaldehyde in a basic environment.[2] The process occurs by successive aldol reactions followed by a Cannizzaro reaction. Impurities include dipentaerythritol and tripentaerythritol.[3]

CH3CHO + 4 CH2O + 1/2 Ca(OH)2 → C(CH2OH)4 + 1/2 (HCOO)2Ca


[edit] References

  1. ^ S. F. Marrian (1948). "The Chemical Reactions of Pentaerythritol and its Derivatives". Chemical Reviews 43 (1): 149-202. 
  2. ^ H. B. J. Schurink (1941). "Pentaerythritol". Org. Synth.; Coll. Vol. 1: 425. 
  3. ^ M. S. Peters, J. A. Quinn (1955). "Pentaerythritol Production Yields". Industrial & Engineering Chemistry 47 (9): 1710-1713. doi:10.1021/ie50549a016.