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Triacetin E1518, or glyceryl triacetate ((C_9H_{14}O_6)), is a colorless, viscous, and nearly odorless liquid used primarily as a food additive (humectant, carrier, softener), plasticizer, and pharmaceutical solvent.
As an E-number additive, Triacetin E1518 is commonly found in chewing gum, baked goods, and flavorings to maintain moisture and texture.
Triacetin E1518 is the organic compound with the formula C3H5(OCOCH3)3.
CAS: 102-76-1
MF: C9H14O6
MW: 218.2
EINECS: 203-051-9
Synonyms
TRIACETIN;TRIACETIN (C2:0);Triacetyl glycerin;GLYCERIN TRIACETATE;1,3-Diacetyloxypropan-2-yl acetate;propane-1,2,3-triyl triethanoate;Glyceryl triacetate,1,2,3-Triacetoxypropane, 1,2,3-Triacetylglycerol, Glycerol triacetate, Triacetin;Triacetin, 99%, extra pure, Ph Eur, USP, BP
Triacetin E1518 is classified as a triglyceride, i.e., the triester of glycerol with acetic acid.
Triacetin E1518 is a colorless, viscous, and odorless liquid with a high boiling point and a low melting point.
Triacetin E1518 has a mild, sweet taste in concentrations lower than 500 ppm, but may appear bitter at higher concentrations.
Triacetin E1518 is one of the glycerine acetate compounds.
Triacetin E1518, also known as 1,2,3-propanetriol triacetate or glyceryl triacetate, is the triester of glycerin and acetic acid.
Triacetin E1518 can be prepared by heating glycerin with acetic anhydride alone or in the presence of finely divided potassium hydrogen sulfate.
Triacetin E1518 can also be prepared by the reaction of oxygen with a liquid-phase mixture of allyl acetate and acetic acid using a bromide salt as a catalyst.
Triacetin E1518 obtained by acetylation of the three hydroxy groups of glycerol.
Triacetin E1518 has fungistatic properties (based on release of acetic acid) and has been used in the topical treatment of minor dermatophyte infections.
Triacetin E1518 is a triester of glycerin and acetic acid that occurs naturally in papaya.
Triacetin E1518 is mainly used as a synthetic flavoring agent in ice-creams, nonalcoholic beverages and baked goods.
Triacetin E1518 is a colorless liquid with a slightly perceptible odor.
Triacetin E1518 Chemical Properties
Melting point: 3 °C(lit.)
Boiling point: 258-260 °C(lit.)
density: 1.16 g/mL at 25 °C(lit.)
vapor density: 7.52 (vs air)
vapor pressure: 0.00248 mm Hg @ 250C
refractive index: n25/D 1.429-1.431(lit.)
FEMA: 2007 | (TRI-)ACETIN
Fp: 300 °F
storage temp.: Sealed in dry,Room Temperature
solubility: Soluble in water, miscible with ethanol (96 per cent) and toluene.
form: Liquid
color: Clear colorless
PH: 5.0-6.0 (20°C, 50g/L in H2O)
Odor: Characteristic odour
explosive limit: 1.05%, 189°F
biological source: synthetic
Odor Type: fruity
Water Solubility: 64.0 g/L (20 ºC)
Merck: 14,9589
JECFA Number: 920
BRN: 1792353
Henry's Law Constant: 8.0×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Dielectric constant: 7.2（20℃）
Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
Major Application: flavors and fragrances
Cosmetics Ingredients Functions: PLASTICISER SOLVENT FILM FORMING FRAGRANCE ANTIMICROBIAL
InChI: 1S/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3
InChIKey: URAYPUMNDPQOKB-UHFFFAOYSA-N
LogP: 0.25
CAS DataBase Reference: 102-76-1(CAS DataBase Reference)
NIST Chemistry Reference: Triacetin E1518(102-76-1)
EPA Substance Registry System: Triacetin E1518 (102-76-1)
Colorless, odorless oily liquid.
Triacetin E1518 is miscible with ethanol, ether, benzene, chloroform and other organic solvents, soluble in acetone, insoluble in mineral oil.
Slightly soluble in water.
25 ° C in water solubility of 5.9g / 100ml.
Triacetin E1518 has a very faint, fruity odor.
Triacetin E1518 has a mild, sweet taste that is bitter above 0.05%.
Colorless liquid; slight fatty odor; bitter taste.
Slightly soluble in water; very soluble in alcohol, ether, and other organic solvents. Combustible.
Triacetin E1518 is a colorless, viscous liquid with a slightly fatty odor.
Uses
As a plasticizer and fragrance fixative, ink solvent, also used in medicine and dye synthesis.
As a chromatographic fixative, solvent, toughener and fragrance fixative.
Humectants; carrier solvents; plasticizers; Triacetin E1518 can absorb carbon dioxide from the natural gas.
In the production of cosmetics, pharmaceuticals and dyes, plasticizers for cigarette filter rods, and so on.
Applied in cosmetics, casting, medicine, dyes and other industries.
Triacetin E1518 is non-toxic, non-irritating.
As the substrate for the determination of lipase, perfume fixative, solvent, gas chromatographic fixative (maximum temperature of 85 ℃, solvent: methanol, chloroform), separation of gas and aldehyde analysis.
Triacetin E1518 is a colorless, oily liquid of slight fatty odor and bitter taste.
Triacetin E1518 is soluble with water and is miscible with alcohol and ether.
Triacetin E1518 functions in foods as a humectant and solvent.
As fixative in perfumery; solvent in manufacture of celluloid, photographic films.
Technical Triacetin E1518 (a mixture of mono-, di-, and small quantities of triacetin) as a solvent for basic dyes, particularly indulines, and tannin in dyeing.
Triacetin E1518, a component of cigarette filters, induced a contact dermatitis in a worker at a cigarette manufacturers.
Triacetin E1518 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.
Triacetin E1518 is used as an excipient in pharmaceutical products, where it is used as a humectant, a plasticizer, and as a solvent.
Potential uses
The plasticizing capabilities of Triacetin E1518 have been utilized in the synthesis of a biodegradable phospholipid gel system for the dissemination of the cancer drug paclitaxel (PTX).
In the study, Triacetin E1518 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 E1518 can also be used as a fuel additive as an antiknock agent for gasoline, and to improve low-temperature viscosity properties of biodiesel.
Triacetin E1518 has been considered as a possible source of food energy in artificial food regeneration systems on long space missions.
Triacetin E1518 is believed to be safe to get over half of one's dietary energy from triacetin.
Pharmaceutical Applications
Triacetin E1518 is mainly used as a hydrophilic plasticizer in both aqueous and solvent-based polymeric coating of capsules, tablets, beads, and granules; typical concentrations used are 10–35% w/w.
Triacetin E1518 is used in cosmetics, perfumery, and foods as a solvent and as a fixative in the formulation of perfumes and flavors.
Clinical Use
Triacetin E1518 is a colorless, oilyliquid with a slight odor and a bitter taste.
Triacetin E1518 issoluble in water and miscible with alcohol and most organicsolvents.
The activity of triacetin is a result of the acetic acid releasedby hydrolysis of the compound by esterases presentin the skin.
Acid release is a self-limiting process becausethe esterases are inhibited below pH 4.
Production
Triacetin E1518 can be derived from the esterification of glycerol and acetic acid.
After preheating glycerol to 50-60 ° C, add acetic acid, benzene and sulfuric acid.
Heat and stir for refluxing dehydration, and recycle the benzene.
Then add acetic anhydride for heating of 4h.
After cooling, the mixture was neutralized with 5% sodium carbonate to pH 7, and the crude layer was dried and the crude oil was dried with calcium chloride.
Distill under reduced pressure, collect the 128-131 ° C (0.93 kPa) fraction, namely glycerol triacetate.
Preparation
By direct reaction of glycerol with acetic acid in the presence of Twitchell’s reagent, or in benzene solution of glycerol and boiling acetic acid in the presence of a cationic resin (Zeo-Karb H) pretreated with dilute H2SO4.
Content analysis
Accurately weigh about 1g of the sample, put Triacetin E1518 into a suitable pressure bottle, add 25 mL of 1mol / L. potassium hydroxide solution and 15 mL of isopropyl alcohol, add stopper, wrap with cloth and put it in a canvas bag.
Put Triacetin E1518 into the water bath of 98 ℃ ± 2 ℃ for 1h, and the water level in the water bath should be slightly higher than the bottle level.
Take the bottle out from the bag, cool it to room temperature in the air, unfold the cloth and stopper to release the residual pressure in the bottle, and then remove the cloth.
Add 6 to 8 drops of phenolphthalein test solution (TS-167), apply 0.5mol / L sulfuric acid for titration of excess alkali until the pink could just disappeared.
At the same time, perform a blank test.
Each mL of 0.5mol / L sulfuric acid is equivalent to 36.37 mg of Triacetin E1518 (C9H14O6).
Manufacturing Process
200 grams of allyl acetate, 450 grams of glacial acetic acid and 3.71 grams of cobaltous bromide were charged to the reactor and the mixture was heated to 100°C.
Pure oxygen was then introduced into the reactor below the surface of the liquid reaction mixture at the rate of 0.5 standard cubic feet per hour.
Initially, all of the oxygen was consumed, but after a period of time oxygen introduced into the mixture passed through unchanged.
During the course of the reaction, a small quantity of gaseous hydrogen bromide (a total of 1.9 grams) was introduced into the reaction zone, along with the oxygen.
The reaction was allowed to continue for 6 hours following which the reaction mixture was distilled.
Essentially complete conversion of the allyl acetate took place.
A yield of 116 grams of glycerol triacetate was obtained, this being accomplished by distilling the Triacetin E1518 overhead from the reaction mixture, at an absolute pressure of approximately 13 mm of mercury.
Synthesis
Triacetin E1518 was first prepared in 1854 by the French chemist Marcellin Berthelot.
Triacetin E1518 was prepared in the 19th century from glycerol and acetic acid.
Triacetin E1518's synthesis from acetic anhydride and glycerol is simple and inexpensive:
3 (CH3CO)2O + C3H5(OH)3 → C3H5(OCOCH3)3 + 3 CH3CO2H
This synthesis has been conducted with catalytic sodium hydroxide and microwave irradiation to give a 99% yield of triacetin.
Synthesis has also been conducted with a cobalt(II) Salen complex catalyst supported by silicon dioxide and heated to 50 °C (122 °F) for 55 minutes to give a 99% yield of Triacetin E1518.
