Pentaerythritol 

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 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 triacrylate1. Derivatives of pentaerythritol are components of alkyd resins, varnishes, PVC stabilizers, tall oil esters, and olefin antioxidants.

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


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.