Trimethylolethane

Trimethylolethane (TME) is the organic compound with the formula CH3C(CH2OH)3. This colorless solid is a triol, as 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).

Trimethylolethane
Names
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 , TME, trimet, metriol, ,
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.968
UNII
Properties
C5H12O3
Molar mass 120.15 g/mol
Density 1.22 g/mL
Melting point 180 °C (356 °F; 453 K)
Hazards
Flammable (F)
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth (blue): no hazard codeReactivity (yellow): no hazard codeSpecial hazards (white): no code
3
Flash point 150 °C (302 °F; 423 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 Cannizzaro 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.

References
  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.
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