Pentaerythritol

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
CAS Number	115-77-5 Y
3D model (Jmol)	Interactive image
ChemSpider	7984 N
ECHA InfoCard	100.003.732
UNII	SU420W1S6N Y
InChI InChI=1S/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2 N Key: WXZMFSXDPGVJKK-UHFFFAOYSA-N N InChI=1/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2 Key: WXZMFSXDPGVJKK-UHFFFAOYAH
SMILES OCC(CO)(CO)CO
Properties
Chemical formula	C5H12O4
Molar mass	136.15
Appearance	white solid
Density	1.396g/cm3
Melting point	260.5 °C (500.9 °F; 533.6 K)
Boiling point	276 °C (529 °F; 549 K) at 30 mmHg
Solubility in water	5.6 g/100 mL at 15 °C
Solubility	Soluble in methanol, ethanol, glycerol, ethylene glycol, formamide; insoluble in acetone, benzene, paraffin, ether, CCl4
Vapor pressure	0.00000008 mmHg (20°C)[2]
Hazards
Flash point	200.1 °C (392.2 °F; 473.2 K)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp)[2]
REL (Recommended)	TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)[2]
IDLH (Immediate danger)	N.D.[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Pentaerythritol is an organic compound, a white, crystalline solid with the formula C₅H₁₂O₄. It is a polyol, and a sugar alcohol with the neopentane backbone and one hydroxyl group in each of the four terminal carbons. It is a building block for the synthesis and production of explosives, plastics, appliances, and many other important chemicals.

History

Pentaerythritol was first synthesized in 1891 by German chemist Bernhard Tollens and his student P. Wigand.^[3]

Uses

Pentaerythritol is a versatile building block for the preparation of many polyfunctionalized compounds, such as the explosive and vasodilator pentaerythritol tetranitrate (PETN) and the polymer cross-linking agent pentaerythritol tetraacrylate.^[4] Derivatives of pentaerythritol are components of alkyd resins, varnishes, polyvinyl chloride stabilizers, tall oil esters, and olefin antioxidants. Can be found in transformer oil, plastics, and many other applications.

Pentaerythritol is also used in the synthesis of Feneritrol.

Medicine

Pentaerythritol is used to synthesize vasodilator pentaerythritol tetranitrate (PETN).

Explosive

Pentaerythritol is used to synthesize explosive pentaerythritol tetranitrate (PETN).

Dielectric

Halogen-free pentaerythritol esters are also environmentally friendly alternative to conventional electrical transformer fluids, being both readily biodegradable and non-hazardous in water. They advantageously replace polychlorobiphenyl (PCB), and even silicone-based or fluorinated hydrocarbons, as dielectric fluid in transformers. Their low volatility and high flash point give them an excellent resistance to ignition in case of major electrical failure and transformer rupture.

Fire retardant

Pentaerythritol is used as a fire retardant, such as in plastics.^[5]

Synthesis

Pentaerythritol can be synthesized by reacting 1 mole Acetaldehyde with 4 moles of Formaldehyde.

The reaction proceeds by substitution of two Alpha hydrogens of acetaldehyde by the reduced form of formaldehyde, i.e. Hydroxymethyl group.

This results in the formation of 3-Hydroxy-2-(hydroxymethyl)propanal The next step proceeds with the Cannizzaro between the above formed product and final mole of formaldehyde.

This forms the final product, pentaerythritol.

References