Triacetin

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Triacetin[1]
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance Oily liquid
Density 1.155 g/cm3[2]
Melting point Template:Chembox CalcTemperatures
Boiling point Template:Chembox CalcTemperatures
Solubility Miscible in EtOH
Soluble in C6H6, (C2H5)2O, acetone[3]
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
Template:Longitem 1.4301 (20 °C)[3]
1.4294 (24.5 °C)[4]
Viscosity 23 cP (20 °C)[2]
Template:Longitem 389 J/mol·K[5]
Template:Longitem 458.3 J/mol·K[5]
Template:Longitem −1330.8 kJ/mol[5]
Template:Longitem 4211.6 kJ/mol[5]
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Explosive limits 7.73%[2]

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Triacetin is the organic compound with the formula Template:Chem2. 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.

Uses

Triacetin is a common food additive, for instance as a solvent in flavorings, and for its humectant function, with E number E1518 and Australian approval code A1518. It is used as an excipient in pharmaceutical products, where it is used as a humectant, a plasticizer, and as a solvent.[8]

Potential uses

The plasticizing capabilities of triacetin have been utilized in the synthesis of a biodegradable phospholipid gel system for the dissemination of the cancer drug paclitaxel (PTX).[9] In the study, triacetin was combined with PTX, ethanol, a phospholipid and a medium chain triglyceride to form a gel-drug complex. This complex was then injected directly into the cancer cells of glioma-bearing mice. The gel slowly degraded and facilitated sustained release of PTX into the targeted glioma cells.

Triacetin can also be used as a fuel additive as an antiknock agent which can reduce engine knocking in gasoline, and to improve cold and viscosity properties of biodiesel.[10]

It has been considered as a possible source of food energy in artificial food regeneration systems on long space missions. It is believed to be safe to get over half of one's dietary energy from triacetin.[11]

Synthesis

Triacetin was first prepared in 1854 by the French chemist Marcellin Berthelot.[12] Triacetin was prepared in the 19th century from glycerol and acetic acid.[13]

Its synthesis from acetic anhydride and glycerol is simple and inexpensive.

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This synthesis has been conducted with catalytic sodium hydroxide and microwave irradiation to give a 99% yield of triacetin.[14] It has also been conducted with a cobalt(II) Salen complex catalyst supported by silicon dioxide and heated to 50 °C for 55 minutes to give a 99% yield of triacetin.[15]

Safety

The US Food and Drug Administration has approved it as generally recognized as safe[16] food additive and included it in the database according to the opinion from the Select Committee On GRAS Substances (SCOGS). Triacetin is included in the SCOGS database since 1975.[17]

Triacetin was not toxic to animals in studies of exposure through repeated inhalation over a relatively short period.[18]

References

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  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)
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  10. ↑ Script error: No such module "Citation/CS1".
  11. ↑ Script error: No such module "Citation/CS1".
  12. ↑ Script error: No such module "Citation/CS1". ; see "Triacétine", pp. 282–283.
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