Trimethylolpropane

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.

Trimethylolpropane

Names
Preferred IUPAC name 2-Ethyl-2-(hydroxymethyl)propane-1,3-diol
Other names TMP, 2-ethyl-2-hydroxymethyl-1,3-propanediol
Identifiers
CAS Number	77-99-6 Y
3D model (JSmol)	Interactive image
ChemSpider	6264 Y
ECHA InfoCard	100.000.978
EC Number	201-074-9
MeSH	C018163
PubChem CID	6510
UNII	090GDF4HBD Y
CompTox Dashboard (EPA)	DTXSID2026448
InChI InChI=1S/C6H14O3/c1-2-6(3-7,4-8)5-9/h7-9H,2-5H2,1H3 N Key: ZJCCRDAZUWHFQH-UHFFFAOYSA-N N
SMILES CCC(CO)(CO)CO
Properties
Chemical formula	C6H14O3
Molar mass	134.17 g/mol
Appearance	White solid
Odor	Faint odor
Density	1.084 g/mL
Melting point	58 °C (136 °F; 331 K)
Boiling point	289 °C (552 °F; 562 K)
Hazards
NFPA 704 (fire diamond)	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). N verify (what is YN ?) Infobox references

Production

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

CH₃CH₂CH₂CHO + 2 CH₂O → CH₃CH₂C(CH₂OH)₂CHO

The second step entails a Cannizzaro 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] It is may also be reacted with epichlorohydrin to produce the triglycidyl ether.^[2]

See also

• Pentaerythritol
• Neopentyl glycol
• Trimethylolethane