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Trimethylolpropane

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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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.978 Edit this at Wikidata
EC Number
  • 201-074-9
MeSH C018163
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H14O3/c1-2-6(3-7,4-8)5-9/h7-9H,2-5H2,1H3Key: ZJCCRDAZUWHFQH-UHFFFAOYSA-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)
NFPA 704 four-colored diamondHealth (blue): no hazard codeFlammability 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. gasolineInstability (yellow): no hazard codeSpecial hazards (white): no code
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 butyraldehyde 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.

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. It is may also be reacted with epichlorohydrin to produce the triglycidyl ether.

See also

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, Roth, Martin; Wolleb, Heinz & Truffer, Marc-Andre, "Process for the preparation of glycidyl ethers", published 1992-11-10, assigned to Ciba-Geigy Corp. 
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