Pentaerythritol
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).
|
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]
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]
Polyester derivatives
Pentaerythritol is a precursor to esters of the type C(CH2OX)4. Such derivatives are
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
References
- ^ ISBN 978-0-85404-182-4.
- ISBN 9781439802465.
- PMID 31304100.
- ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0485". National Institute for Occupational Safety and Health (NIOSH).
- .
- ; Collected Volumes, vol. 1, p. 425.
- PMID 18876970.
- ISBN 978-3527306732.
- ^ NPCS Board of Consultants & Engineers (2016). The Complete Book on Adhesives, Glues & Resins Technology (with Process & Formulations) 2nd Revised Edition.
- ^ NIIR Board of Engineers & Consultants (2005). Synthetic Resins Technology Handbook.
- ISBN 9781420027181.
- ISBN 9780849377877.
- PMID 18876970.
- .
- ISBN 978-3527306732.