Trimethylolpropane

Trimethylolpropane
Names
	IUPAC name 2-(hydroxymethyl)-2-ethylpropane-1,3-diol
	Other names TMP, 2-ethyl-2-hydroxymethyl-1,3-propanediol
Identifiers
CAS Number	77-99-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	6264 ;
ECHA InfoCard	100.000.978
EC Number	201-074-9
MeSH	C018163
PubChem CID	6510;
UNII	090GDF4HBD ;
	InChI InChI=1S/C6H14O3/c1-2-6(3-7,4-8)5-9/h7-9H,2-5H2,1H3 Key: ZJCCRDAZUWHFQH-UHFFFAOYSA-N ;
	SMILES CCC(CO)(CO)CO;
Properties
Chemical formula	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EU classification (DSD) (outdated)	Flammable (F)
NFPA 704	3
Flash point	172 °C (342 °F; 445 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

Trimethylolpropane (TMP) is the organic compound with the formula CH₃CH₂C(CH₂OH)₃. This colourless 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 polymerisation initiator.^[1]

References

1 2 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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[Ullmann-1] 1 2 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.