Triacetin

Triacetin[1]
Skeletal formula of triacetin
Ball-and-stick model of the triacetin molecule
Names
Systematic IUPAC name
Propane-1,2,3-triyl triacetate
Other names
  • Glycerol triacetate[2]
  • glycerin triacetate
  • 1,2,3-triacetylglycerol
  • 1,2,3-triacetoxypropane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.775 Edit this at Wikidata
EC Number
  • 203-051-9
E number E1518 (additional chemicals)
KEGG
RTECS number
  • AK3675000
UNII
  • InChI=1S/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3 checkY
    Key: URAYPUMNDPQOKB-UHFFFAOYSA-N checkY
  • InChI=1/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3
    Key: URAYPUMNDPQOKB-UHFFFAOYAH
  • CC(=O)OC(COC(=O)C)COC(C)=O
Properties
C9H14O6
Molar mass 218.205 g·mol−1
Appearance Oily liquid
Density 1.155 g/cm3[3]
Melting point −78 °C (−108 °F; 195 K)
at 760 mmHg[2]
Boiling point 259 °C (498 °F; 532 K)
at 760 mmHg[2]
6.1 g/100 mL[2]
Solubility Miscible in EtOH
Soluble in C6H6, (C2H5)2O, acetone[2]
Vapor pressure 0.051 Pa (11.09 °C)
0.267 Pa (25.12 °C)
2.08 Pa (45.05 °C)[4]
ln(P/Pa)=22.819-4493/T(K)-807000/T(K)²
1.4301 (20 °C)[2]
1.4294 (24.5 °C)[4]
Viscosity 23 cP (20 °C)[3]
Thermochemistry
389 J/mol·K[5]
458.3 J/mol·K[5]
−1330.8 kJ/mol[5]
4211.6 kJ/mol[5]
Hazards
NFPA 704 (fire diamond)
[3]
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 138 °C (280 °F; 411 K)[3]
430 °C (806 °F; 703 K)[3]
Explosive limits 7.73%[3]
Lethal dose or concentration (LD, LC):
1100 mg/kg (mice, oral)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Triacetin is the organic compound with the formula C3H5(OCOCH3)3. It is classified as a triglyceride, i.e., the triester of glycerol with acetic acid.[6] It is a colorless, viscous, and odorless liquid with a high boiling point and a low melting point. It has a mild, sweet taste in concentrations lower than 500 ppm, but may appear bitter at higher concentrations.[7] It is one of the glycerine acetate compounds.

  1. ^ Merck Index (11th ed.). p. 9405.
  2. ^ a b c d e f Lide DR, ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  3. ^ a b c d e f g "MSDS of Triacetin". fishersci.ca. Fisher Scientific. Retrieved 2014-06-20.
  4. ^ a b Woodman AL, Adicoff A (1963). "Vapor Pressure of Tiracetin, Triethylene Glycol Dinitrate, and Metriol Trinitrate". Journal of Chemical & Engineering Data. 8 (2): 241–242. doi:10.1021/je60017a033.
  5. ^ a b c d Triacetin in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD)
  6. ^ Kong P, Aroua MK, Daud WM, Lee HV, Cognet P, Pérès Y (2016). "Catalytic role of solid acid catalysts in glycerol acetylation for the production of bio-additives: a review". RSC Advances. 6 (73): 68885–68905. Bibcode:2016RSCAd...668885K. doi:10.1039/C6RA10686B. S2CID 102384754.
  7. ^ Arctander S (1969). Perfume and Flavor Chemicals (II K - Z). Elizabeth, N.J.: Published by the Author. p. 2971. ISBN 978-0-931710-37-7.