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 industrially via a two step process, starting with the aldol condensation of butyraldehyde with formaldehyde:
The second step is a classical Cannizzaro reaction using sodium hydroxide: CH3CH2C(CH2OH)2CHO + CH2O + NaOH → CH3CH2C(CH2OH)3 + NaO2CH Approximately 200,000,000 kg are produced annually in this way.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.
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 strong photoinitiator. It is may also be reacted with epichlorohydrin to produce the triglycidyl ether.
See also Pentaerythritol Neopentyl glycol Trimethylolethane
References