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 |
EC Number |
|
KEGG | |
PubChem CID
|
|
RTECS number |
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
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 |
| |
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). | |
![]() ![]() ![]() | |
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.
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.[6]
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). It can be found in transformer oil, plastics, paints, cosmetics, and many other applications.[8][9]
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 agent pentaerythritol tetraacrylate.[10]
Pentaerythritol is used as a fire retardant, such as in plastics.[citation needed] It produces a thick carbon barrier upon heating, protecting the surface substrate.
Pentaerythritol is one of the most common main active components in intumescent paints and coatings. It acts as a carbon donor and together with an acid donor, most commonly ammonium polyphosphate (APP), and a blowing agent, most commonly melamine.