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Wikipedia

Trimethylolethane

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).

Trimethylolethane
Names
Preferred IUPAC name
2-(Hydroxymethyl)-2-methylpropane-1,3-diol
Other names
TME; trimet; metriol; methriol; pentaglycerol; pentaglycerine; methyltrimethanolmethane; methyltrimethylolmethane; tris(hydroxymethyl)ethane, 1,1,1-tris(hydroxymethyl)ethane, 1,1,1-trimethanolethane; lidaprim [1], TME, trimet, metriol, ,[2]
Identifiers
  • 77-85-0 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 6256
ECHA InfoCard 100.000.968
EC Number
  • 201-063-9
  • 6502
UNII
  • 5D10NYN23W Y
  • DTXSID2026444
  • InChI=1S/C5H12O3/c1-5(2-6,3-7)4-8/h6-8H,2-4H2,1H3
    Key: QXJQHYBHAIHNGG-UHFFFAOYSA-N
  • CC(CO)(CO)CO
Properties
C5H12O3
Molar mass 120.15 g/mol
Density 1.22 g/mL
Melting point 180 °C (356 °F; 453 K)
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
Health (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 150 °C (302 °F; 423 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Production edit

Trimethylolethane is produced via a two step process, starting with the condensation reaction of propionaldehyde with formaldehyde:

CH3CH2CHO + 2 CH2O → CH3C(CH2OH)2CHO

The second step entails a Cannizzaro reaction:

CH3C(CH2OH)2CHO + CH2O + NaOH → CH3C(CH2OH)3 + NaO2CH

A few thousand tons are produced annually in this way.[1]

Applications edit

TME is an intermediate in the production of alkyd and polyester resins, powder coating resins, synthetic lubricants based on polyol esters, stabilizers for plastics, plasticizers, and pigment coatings based on titanium dioxide. Trimethylolethane based resins have superior weatherability and resistance to alkali and heat. Trimethylolethane is used in some phase change materials. The typical composition is then 63 wt.% TME with 37 wt.% water. The mixture has melting point of 29.8 °C and heat of fusion 218 kJ/kg. Nitration of trimethylolethane gives trimethylolethane trinitrate, an explosive, monopropellant, and energetic plasticizer.

See also edit

References edit

  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.

External links edit

  • MSDS
  • TME

trimethylolethane, organic, compound, with, formula, ch3c, ch2oh, this, colorless, solid, triol, contains, three, hydroxy, functional, groups, more, specifically, features, three, primary, alcohol, groups, compact, neopentyl, structure, esters, known, their, r. 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 Trimethylolethane NamesPreferred IUPAC name 2 Hydroxymethyl 2 methylpropane 1 3 diolOther names TME trimet metriol methriol pentaglycerol pentaglycerine methyltrimethanolmethane methyltrimethylolmethane tris hydroxymethyl ethane 1 1 1 tris hydroxymethyl ethane 1 1 1 trimethanolethane lidaprim 1 TME trimet metriol 2 IdentifiersCAS Number 77 85 0 Y3D model JSmol Interactive imageChemSpider 6256ECHA InfoCard 100 000 968EC Number 201 063 9PubChem CID 6502UNII 5D10NYN23W YCompTox Dashboard EPA DTXSID2026444InChI InChI 1S C5H12O3 c1 5 2 6 3 7 4 8 h6 8H 2 4H2 1H3Key QXJQHYBHAIHNGG UHFFFAOYSA NSMILES CC CO CO COPropertiesChemical formula C5H12O3Molar mass 120 15 g molDensity 1 22 g mLMelting point 180 C 356 F 453 K HazardsGHS labelling PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P261 P264 P270 P271 P280 P301 P312 P302 P352 P304 P340 P305 P351 P338 P312 P330 P332 P313 P337 P313 P362 P403 P233 P405 P501NFPA 704 fire diamond 3Flash point 150 C 302 F 423 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production 2 Applications 3 See also 4 References 5 External linksProduction editTrimethylolethane is produced via a two step process starting with the condensation reaction of propionaldehyde with formaldehyde CH3CH2CHO 2 CH2O CH3C CH2OH 2CHOThe second step entails a Cannizzaro reaction CH3C CH2OH 2CHO CH2O NaOH CH3C CH2OH 3 NaO2CHA few thousand tons are produced annually in this way 1 Applications editTME is an intermediate in the production of alkyd and polyester resins powder coating resins synthetic lubricants based on polyol esters stabilizers for plastics plasticizers and pigment coatings based on titanium dioxide Trimethylolethane based resins have superior weatherability and resistance to alkali and heat Trimethylolethane is used in some phase change materials The typical composition is then 63 wt TME with 37 wt water The mixture has melting point of 29 8 C and heat of fusion 218 kJ kg Nitration of trimethylolethane gives trimethylolethane trinitrate an explosive monopropellant and energetic plasticizer See also editPentaerythritol Neopentyl glycol TrimethylolpropaneReferences edit Peter Werle Marcus Morawietz Stefan Lundmark Kent Sorensen Esko Karvinen Juha Lehtonen Alcohols Polyhydric in Ullmann s Encyclopedia of Industrial Chemistry Wiley VCH Weinheim 2008 External links editMSDS TME Retrieved from https en wikipedia org w index php title Trimethylolethane amp oldid 1182914321, wikipedia, wiki, book, books, library,

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