Trimethylolethane

Trimethylolethane
Identifiers
CAS number 77-85-0 YesY
Jmol-3D images Image 1
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
NFPA 704.svg
3
 
 
Flash point 150 °C
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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).

Contents

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


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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


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