Trimethylolethane Identifiers CAS number Jmol-3D images Image 1 Properties Molecular formula C5H12O3 Molar mass 120.15 g/mol Density 1.22 g/mL Melting point
Hazards EU classification Flammable (F) NFPA 704 Flash point 150 °C (what is: /?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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).
- 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.
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.
- ^ 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.
Wikimedia Foundation. 2010.
Look at other dictionaries:
trimethylolethane — noun An organic compound with the chemical formula CHC(CHOH), a triol whose esters are known for their resistance to heat, light, hydrolysis, and oxidation … Wiktionary
Trimethylolethane trinitrate — IUPAC name [2 methyl 3 nitrooxy 2 (nitrooxymethyl)propyl] nitrate … Wikipedia
Plasticizer — Plasticizers are additives that increase the plasticity or fluidity of the material to which they are added, these include plastics, cement, concrete, wallboard and clay bodies. Although the same compounds are often used for both plastics and… … Wikipedia
Propionaldehyde — Not to be confused with propanol. Propanal … Wikipedia