Trimethylolpropane

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Trimethylolpropane
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Names
Preferred IUPAC name
2-Ethyl-2-(hydroxymethyl)propane-1,3-diol
Other names
TMP, 2-ethyl-2-hydroxymethyl-1,3-propanediol
Identifiers
3D model (JSmol)
ChemSpider
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EC Number
  • 201-074-9
MeSH C018163
PubChem CID
UNII
  • InChI=1S/C6H14O3/c1-2-6(3-7,4-8)5-9/h7-9H,2-5H2,1H3 X mark.svgN
    Key: ZJCCRDAZUWHFQH-UHFFFAOYSA-N X mark.svgN
  • CCC(CO)(CO)CO
Properties
C6H14O3
Molar mass 134.17 g/mol
AppearanceWhite 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).
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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.

Contents

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] It is may also be reacted with epichlorohydrin to produce the triglycidyl ether. [2]

See also

Related Research Articles

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In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group (−OH) bound to a saturated carbon atom. The term alcohol originally referred to the primary alcohol ethanol, which is used as a drug and is the main alcohol present in alcoholic drinks. An important class of alcohols, of which methanol and ethanol are the simplest members, includes all compounds for which the general formula is CnH2n+1OH. Simple monoalcohols that are the subject of this article include primary, secondary and tertiary alcohols.

Ether Class of organic compounds

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Acetophenone Chemical compound

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Dicarbonyl

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Methyltrichlorosilane Chemical compound

Methyltrichlorosilane, also known as trichloromethylsilane, is an organosilicon compound with the formula CH3SiCl3. It is a colorless liquid with a sharp odor similar to that of hydrochloric acid. As methyltrichlorosilane is a reactive compound, it is mainly used a precursor for forming various cross-linked siloxane polymers.

Trimethylolethane Chemical compound

Trimethylolethane (TME) is the organic compound with the formula CH3C(CH2OH)3. This colorless solid is a triol, as it contains three hydroxy functional groups. More specifically, it features three primary alcohol groups in a compact neopentyl structure. Its esters are known for their resistance to heat, light, hydrolysis, and oxidation. More important than TME and closely related is trimethylolpropane (TMP).

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Diphenolic acid Organic acid

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Propionaldehyde Chemical compound

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Ureas

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References

  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.
  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.