Trimethylolpropane Explained

Trimethylolpropane (TMP) is the organic compound with the formula CH₃CH₂C(CH₂OH)₃. This colourless to white solid with a faint odor 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)₂CHOThe second step entails a Cannizaro reaction:

CH₃CH₂C(CH₂OH)₂CHO + CH₂O + NaOH → CH₃CH₂C(CH₂OH)₃ + NaO₂CHApproximately 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] It is may also be reacted with epichlorohydrin to produce the triglycidyl ether.^[2]

See also

• Pentaerythritol
• Neopentyl glycol
• Trimethylolethane

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.
2. US. 5162547. Process for the preparation of glycidyl ethers. 1992-11-10. Roth. Martin. Wolleb. Heinz. Truffer. Marc-Andre. Ciba-Geigy Corp..