Pentaerythritol
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Preferred IUPAC name
2,2-Bis(hydroxymethyl)propane-1,3-diol[1] | |
Other names
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| ECHA InfoCard | 100.003.732 |
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CompTox Dashboard (EPA) |
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| Properties | |
| C(CH2OH)4 | |
| Molar mass | 136.147 g·mol−1 |
| Appearance | white crystalline solid |
| Odor | Odorless |
| 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 |
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| 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] |
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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 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
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
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. Relevant to resins, pentaerythritol is a precursor to other polyol, such as dipentaerythritol:[8]
- 2 C(CH2OH)4 → O[CH2C(CH2OH)3]2 + H2O
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
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
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]