Trimethylolethane

Trimethylolethane
IUPAC name 2-(hydroxymethyl)-2-methylpropane-1,3-diol
Other names TME; trimet; metriol; methriol; pentaglycerol; pentaglycerine; methyltrimethanolmethane; methyltrimethylolmethane; tris(hydroxymethyl)ethane, 1,1,1-tris(hydroxymethyl)ethane, 1,1,1-trimethanolethane; lidaprim [1], TME, trimet, metriol, ,[2]
Identifiers
CAS number	77-85-0 Y
Jmol-3D images	Image 1
SMILES CC(CO)(CO)CO
Properties
Molecular formula	C5H12O3
Molar mass	120.15 g/mol
Density	1.22 g/mL
Melting point	180 °C
Hazards
EU classification	Flammable (F)
NFPA 704	3
Flash point	150 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Trimethylolethane (TME) is the organic compound with the formula CH₃C(CH₂OH)₃. This colorless solid is a triol, that is it contains three hydroxy functional groups. More specifically, it features three primary alcohol groups in a compact neopentyl structure. Its esters are known for their resistance to heat, light, hydrolysis, and oxidation. More important than TME and closely related is trimethylolpropane (TMP).

Production

Trimethylolethane is produced via a two step process, starting with the condensation reaction of propionaldehyde with formaldehyde:

CH₃CH₂CHO + 2 CH₂O → CH₃C(CH₂OH)₂CHO

The second step entails a Cannizaro reaction:

CH₃C(CH₂OH)₂CHO + CH₂O + NaOH → CH₃C(CH₂OH)₃ + NaO₂CH

A few thousand tons are produced annually in this way.^[1]

Applications

TME is an intermediate in the production of alkyd and polyester resins, powder coating resins, synthetic lubricants based on polyol esters, stabilizers for plastics, plasticizers, and pigment coatings based on titanium dioxide. Trimethylolethane based resins have superior weatherability and resistance to alkali and heat. Trimethylolethane is used in some phase change materials. The typical composition is then 63 wt.% TME with 37 wt.% water. The mixture has melting point of 29.8 °C and heat of fusion 218 kJ/kg. Nitration of trimethylolethane gives trimethylolethane trinitrate, an explosive, monopropellant, and energetic plasticizer.

1. ^ Peter Werle, Marcus Morawietz, Stefan Lundmark, Kent Sörensen, Esko Karvinen, Juha Lehtonen “Alcohols, Polyhydric” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2008.

External links

• MSDS
• MSDS