Trimethylolpropane

Trimethylolpropane
Names
IUPAC name
2-(hydroxymethyl)-2-ethylpropane-1,3-diol
Other names
TMP, 2-ethyl-2-hydroxymethyl-1,3-propanediol
Identifiers
77-99-6 
Jmol-3D images Image
UNII 090GDF4HBD Yes
Properties
C6H14O3
Molar mass 134.17 g/mol
Density 1.084 g/mL
Melting point 58 °C (136 °F; 331 K)
Boiling point 289 °C (552 °F; 562 K)
Hazards
EU classification Flammable (F)
NFPA 704
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., gasoline) Health (blue): no hazard code Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
3
Flash point 172 °C (342 °F; 445 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Trimethylolpropane (TMP) is the organic compound with the formula CH3CH2C(CH2OH)3. This colorless solid is a triol. Containing three hydroxy functional groups, TMP is a widely used building block in the polymer industry.

Production

TMP is produced via a two step process, starting with the condensation of butanal with formaldehyde:

CH3CH2CH2CHO + 2 CH2O → CH3CH2C(CH2OH)2CHO

The second step entails a Cannizaro reaction:

CH3CH2C(CH2OH)2CHO + CH2O + NaOH → CH3CH2C(CH2OH)3 + NaO2CH

Approximately 200,000,000 kg are produced annually in this way.[1]

Applications

TMP is mainly consumed as a precursor to alkyd resins. Otherwise, acrylated and alkoxylated TMP's are used as multifunctional monomers to produce various coatings, Ethoxylated and propoxylated TMP, derived condensation of from TMP and the epoxides, are used for production of flexible polyurethanes. Allyl ether derivatives of TMP, with the formula CH3CH2C(CH2OCH2CH=CH2)3-x(CH2OH)x are precursors to high-gloss coatings and ion exchange resins. The oxetane "TMPO" is a photoinduceable polymerization initiator.[1]

References

  1. ↑ 1.0 1.1 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.