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Triacetin

Triacetin, also known as glycerol triacetate or glyceryl triacetate, is an organic compound with the molecular formula C₉H₁₄O₆ and a molecular weight of 218.20 g/mol.^[1] It is the triester formed by the acetylation of the three hydroxy groups of glycerol with acetic acid, resulting in a colorless, oily liquid that is miscible with ethanol, ether, and chloroform but has limited solubility in water (approximately 58 g/L at 25 °C).^[1] With a melting point of -78 °C and a boiling point of 258–260 °C, triacetin exhibits fungistatic properties due to the slow release of acetic acid and is commonly synthesized by the acetylation of glycerol with acetic acid or acetic anhydride.^[1] Triacetin serves as a versatile additive across multiple industries, including as a plasticizer, solvent, and humectant in plastics, food, cosmetics, and pharmaceuticals; detailed applications are covered in subsequent sections.^[2]^[3] Triacetin has low acute toxicity and is generally recognized as safe (GRAS) for food use by the FDA, safe for cosmetics by the Cosmetic Ingredient Review, and metabolizes harmlessly into glycerol and acetic acid, though rare allergic reactions may occur; further safety details are in the dedicated section.^[1]^[2]^[3]

Chemical properties

Molecular structure

Triacetin has the chemical formula C₉H₁₄O₆.^[1] Its systematic IUPAC name is propane-1,2,3-triyl triacetate, reflecting the esterification of a propane chain.^[1] The molar mass of triacetin is 218.205 g/mol, calculated from its atomic composition.^[1] Triacetin is classified as a triglyceride, specifically the triester formed from one molecule of glycerol and three molecules of acetic acid.^[1] Structurally, it consists of a glycerol backbone—derived from propane-1,2,3-triol—with three acetate groups (CH₃COO-) attached to the primary and secondary hydroxyl positions via ester linkages, resulting in the formula shown below:

\ce{CH3COOCH2-CH(OCOCH3)-CH2OCOCH3}

This configuration imparts triacetin with its characteristic properties as a simple triacylglycerol analog.^[1]

Physical characteristics

Triacetin appears as a colorless, oily liquid at room temperature, characterized by a faint fatty odor.^[1] It exhibits a density of 1.16 g/cm³ at 25 °C, making it denser than water and suitable for various industrial handling processes.^[4] The compound has a melting point of 3 °C, though it often remains in a supercooled liquid state under ambient conditions due to its tendency to avoid crystallization without seeding.^[4] Its boiling point is 258 °C at standard pressure, indicating thermal stability at elevated temperatures.^[1] The flash point is 148 °C (closed cup), relevant for safe storage and transport.^[4] Triacetin demonstrates moderate solubility in water, approximately 5.8 g/100 mL at 25 °C, while being fully miscible with ethanol, ether, acetone, and other organic solvents, a behavior attributed to its ester structure.^[1] Its dynamic viscosity ranges from 21 to 24 mPa·s at 20 °C, contributing to its viscous nature and influencing flow properties in applications.^[4]

Property	Value	Conditions
Density	1.16 g/cm³	25 °C
Melting point	3 °C	-
Boiling point	258 °C	760 mmHg
Flash point	148 °C	Closed cup
Water solubility	5.8 g/100 mL	25 °C
Viscosity	21–24 mPa·s	20 °C

Synthesis

Historical synthesis

Triacetin, also known as glycerol triacetate, was first synthesized in 1854 by the French chemist Marcellin Berthelot as part of his doctoral research on the combinations of glycerol with acids. In his seminal work, Berthelot heated glycerol with excess acetic acid at elevated temperatures to produce the triester, demonstrating that natural fat components could be artificially replicated through esterification. This synthesis marked a foundational achievement in organic chemistry, illustrating the feasibility of constructing complex esters from simpler precursors and challenging prevailing views on the uniqueness of organic compounds. The method employed by Berthelot and other early chemists in the mid-19th century relied on direct esterification without the benefit of modern catalysts, typically involving prolonged refluxing of glycerol with acetic acid or, in some cases, acetic anhydride. Glycerol itself was sourced as a byproduct from the saponification of natural fats and oils during soap production. These reactions proceeded slowly due to the equilibrium-limited nature of esterification and the polyfunctional reactivity of glycerol, often yielding mixtures of mono-, di-, and triacetins alongside unreacted materials. Historical preparations suffered from significant limitations in both yield and purity. Without effective catalysts to shift the equilibrium or accelerate the reaction, conversions to triacetin were generally low, requiring extensive excess of acetic acid and long reaction times—often several hours to days—to achieve partial completion. Purification posed further challenges, as the products formed azeotropic mixtures that were separated primarily through fractional distillation under reduced pressure, resulting in impure triacetin contaminated by partial esters and acetic acid residues. These constraints reflected the nascent state of organic synthesis techniques at the time, where empirical heating and distillation were the primary tools for isolating target compounds.^[5]

Modern production methods

Modern production of triacetin primarily involves the esterification of glycerol with acetic acid or acetic anhydride, following the general reaction where one molecule of glycerol reacts with three molecules of acetic acid to form triacetin and three molecules of water, or with acetic anhydride to yield triacetin and acetic acid as a byproduct.^[6] This process occurs in sequential steps: initial formation of monoacetin, followed by diacetin, and finally triacetin, with the reaction equilibrium not favoring the final step due to thermodynamic limitations (ΔG = 55.58 kJ/mol for the tertiary acetylation), requiring strategies like water removal to drive completion.^[6] To enhance efficiency, acid catalysts such as sulfuric acid are commonly employed in laboratory and industrial settings, achieving conversions up to 99.4% in as little as 0.5 hours under optimized conditions.^[6] Heterogeneous catalysts like Amberlyst-36 or sulfonated resins further improve scalability by allowing easy separation and reuse, with yields exceeding 98% in continuous systems.^[6] Emerging green alternatives, including enzymatic catalysts like Novozym 435, offer up to 95% conversion over 12 hours, promoting sustainability without corrosive byproducts.^[6] Industrial processes utilize continuous esterification in fixed-bed reactors or reactive distillation columns, where glycerol—often sourced as a renewable byproduct from biodiesel production (which yields approximately 10 wt% crude glycerol from the feedstock)—is fed alongside acetic acid under controlled temperature and pressure to maximize throughput.^[6] Reactive distillation integrates reaction and separation, boosting glycerol conversion to 98.5% while minimizing energy use. An alternative industrial method involves the catalytic oxidation of allyl acetate with oxygen in the presence of acetic acid, typically using bromide or palladium catalysts.^[3] Purification typically involves vacuum distillation to isolate high-purity triacetin (>99%) from unreacted glycerol, mono- and diacetins, and acetic acid, often in a single or multi-stage setup to achieve pharmaceutical-grade quality.^[7] Additional steps, such as neutralization and washing, may precede distillation to remove catalyst residues. Global consumption exceeds 155 kilotons annually as of 2025, closely linked to the availability of biodiesel-derived glycerol, with market growth projected at a 4.1% CAGR to 190 kilotons by 2030 due to demand in plastics and pharmaceuticals.^[8]

Uses

Industrial applications

Triacetin serves as a key plasticizer in the production of cellulose acetate films, plastics, and coatings, where it enhances material flexibility and compatibility with cellulosic resins such as cellulose acetate and nitrocellulose.^[9]^[10] This role is particularly prominent in manufacturing processes requiring durable, pliable films and coatings, as triacetin's compatibility in all proportions with these resins prevents brittleness and improves mechanical properties.^[9] In cigarette filter production, triacetin acts as a plasticizer for cellulose acetate rods, contributing to structural integrity and filter efficiency.^[1]^[11] As a solvent and lubricant, triacetin is employed in the formulation of inks, dyes, and adhesives due to its high solvency power and low volatility, which facilitate effective dissolution and stabilization of components.^[12]^[1] In printing inks and dye processing, it improves performance by acting as a performance enhancer and solvent for basic dyes like indulines and tannin, ensuring uniform application and reduced viscosity.^[13]^[1] For adhesives, triacetin's lubricating properties aid in processing, enhancing flow and adhesion without compromising final product strength.^[10]^[14] In the fuel industry, triacetin functions as an oxygenated additive in biodiesel blends, improving combustion efficiency and reducing emissions such as CO, HC, and CO₂.^[15]^[16] When blended at concentrations up to 4-10% with waste cooking oil biodiesel or algae-based fuels, it acts as an antiknock agent, elevating cetane number and brake thermal efficiency while lowering exhaust pollutants compared to neat biodiesel or diesel.^[17]^[18]^[19] This application leverages triacetin's biodegradability and compatibility, making it a sustainable enhancer for biofuel performance.^[20] Triacetin is utilized in cosmetics as a biocide and fragrance carrier, providing antimicrobial protection through the controlled release of acetic acid and stabilizing scents in formulations.^[21]^[22] Its low volatility and solvency enable it to fix and extend fragrance longevity in perfumes, lotions, and other personal care products without altering sensory profiles.^[12]^[23] As a biocide, it inhibits fungal growth at concentrations ranging from 0.8% to 4.0%, ensuring product safety and shelf life in various cosmetic matrices.^[21]^[22] In the tobacco industry, triacetin acts as a humectant to maintain moisture in cigarettes and cigars, preventing dryness and improving draw characteristics.^[24]^[25] It also stabilizes tobacco blends by retaining humidity and enhancing flavor retention during processing and storage.^[26] For explosives, triacetin serves as a stabilizer and gelatinizing agent, preventing degradation in formulations like dynamite and solid rocket fuels while improving consistency and safety.^[27]^[28]^[29]

Food and pharmaceutical uses

Triacetin, designated as the food additive E1518 in the European Union, serves primarily as a solvent for flavorings and a humectant in various food products. It is commonly employed to dissolve and stabilize flavor compounds, ensuring even distribution and longevity of taste in items such as chewing gum and baked goods. In chewing gum formulations, triacetin acts as a plasticizer and humectant, maintaining flexibility and moisture retention to prevent brittleness during storage and use.^[3]^[30]^[12] As a carrier for essential oils and flavors, particularly in confectionery, triacetin facilitates the solubilization of both water- and oil-soluble components, enhancing flavor stability and delivery in products like candies and gummies. This role is critical for preserving volatile aroma compounds without altering the sensory profile. Regulatory approvals limit its use as a flavor carrier to a maximum of 3 g/kg (0.3%) in foodstuffs and 1 g/kg (0.1%) in beverages under EU guidelines, while the U.S. Food and Drug Administration affirms it as generally recognized as safe (GRAS) with no specific concentration limits beyond current good manufacturing practices.^[31]^[32]^[3] In pharmaceutical applications, triacetin functions as an excipient, particularly as a plasticizer in soft gelatin capsules to improve film flexibility and coating integrity. It is also utilized as a solvent in topical ointments for dermatological treatments, such as those targeting minor fungal infections like ringworm, where its fungistatic properties—derived from acetic acid release—aid in therapeutic efficacy. Triacetin has been safely incorporated into food and pharmaceutical products for over 75 years, with no significant adverse issues reported in these regulated sectors.^[33]^[1]^[34]^[2]

Potential and emerging applications

Triacetin has shown promise in the development of biodegradable gels for controlled drug delivery, particularly in oncology. As a plasticizer, it enhances the formulation of phospholipid-based gels that encapsulate hydrophobic drugs like paclitaxel, enabling sustained release for localized cancer treatment. For instance, in intratumoral injections for glioma models, triacetin-facilitated gels have demonstrated improved drug solubility and prolonged release profiles, potentially reducing systemic toxicity compared to conventional intravenous administration.^[35]^[36] In advanced biofuel applications, triacetin serves as an oxygenated additive to enhance combustion efficiency and reduce emissions in biodiesel blends. Derived from glycerol, it increases the oxygen content of fuels like waste cooking oil biodiesel, leading to lower CO and hydrocarbon emissions while improving cold flow properties and cetane number. Studies on diesel engines have reported up to 20% reductions in particulate matter when triacetin is blended at 5-10% concentrations, positioning it as a sustainable option for next-generation biofuels.^[18]^[16] Triacetin's potential as a compact energy source for long-duration space missions stems from its hydrolysis into glycerol and acetate, which can provide nutritional calories in artificial food systems. Building on its established status as a food additive, animal studies indicate that up to 50% of dietary energy could be derived from triacetin via parenteral infusion without adverse effects, offering a lightweight alternative to traditional rations for missions exceeding several years.^[37]^[38] As a sustainable solvent in green chemistry, triacetin excels in hydroformylation reactions, converting alkenes to aldehydes with high efficiency and minimal environmental impact. In rhodium-catalyzed processes, it outperforms traditional solvents like toluene by achieving higher turnover frequencies (e.g., 619 h⁻¹ for 1-octene) and reducing isomerization side products, especially for renewable feedstocks such as limonene and perillyl alcohol, where yields exceed 90%. Its biodegradability, low volatility, and recyclability after product separation contribute to lower process mass intensity and E-factors, aligning with principles of sustainable catalysis.^[39]

Safety and environmental considerations

Health and toxicity

Triacetin exhibits low acute oral toxicity, with an LD50 value of 1100 mg/kg body weight reported in female Swiss mice following oral administration. Symptoms of toxicity in animals include weakness, ataxia, severe dyspnea, muscular tremors, and occasional convulsions near death, though these effects occur at high exposure levels.^[1] Dermal and inhalation exposures to triacetin demonstrate minimal toxicity. The dermal LD50 in rabbits exceeds 5000 mg/kg body weight, indicating low absorption and systemic effects through the skin. Triacetin is non-irritating to rabbit skin and eyes in standard Draize tests, with no evidence of corneal injury or persistent ocular effects.^[40] For inhalation, short-term exposure studies in rats show no adverse effects, with an LC50 greater than 1.721 mg/L over 4 hours, attributed to its low vapor pressure.^[41] Upon absorption, triacetin is rapidly metabolized via hydrolysis by ubiquitous esterases into glycerol and acetic acid, both naturally occurring metabolites that are further processed through standard endogenous pathways without accumulation. This metabolic fate contributes to its low toxicity profile. Triacetin shows no evidence of genotoxicity in available assays, and it is not classified as carcinogenic.^[42] Similarly, reproductive and developmental toxicity studies in rats report no adverse effects at doses up to 1000 mg/kg body weight per day.^[41] Due to its low toxicity and favorable metabolic profile, triacetin is considered safe for cosmetic and topical applications at concentrations up to 4%, as determined by the Cosmetic Ingredient Review Expert Panel.^[40] It is also recognized as a generally regarded as safe (GRAS) excipient in pharmaceutical formulations.^[21]

Regulatory approvals

Triacetin is affirmed as generally recognized as safe (GRAS) by the United States Food and Drug Administration (FDA) for use in food under 21 CFR 184.1901, where it functions as a flavoring agent, adjuvant, humectant, masticatory substance, processing aid, solvent or vehicle, and surface-active agent, with usage levels limited to those not exceeding current good manufacturing practices (GMP).^[3] This GRAS status stems from its demonstrated low toxicity in relevant studies.^[40] In the European Union, triacetin is authorized as a food additive with the E number E1518, primarily as a carrier solvent for flavorings and other additives, subject to purity criteria specified by the European Food Safety Authority (EFSA), including limits on impurities such as heavy metals and arsenic.^[43]^[44] The Cosmetic Ingredient Review (CIR) Expert Panel has assessed triacetin and concluded it is safe for use in cosmetic formulations at concentrations of 0.8% to 4.0%, where it serves as a humectant, plasticizer, and solvent.^[40] On the international level, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) has evaluated triacetin as a flavoring agent, determining no safety concern at current estimated dietary intake levels and assigning an acceptable daily intake (ADI) of "not specified," which supports its use under GMP in food applications.^[45] For pharmaceutical excipients, triacetin is included in authoritative compendia such as the United States Pharmacopeia (USP), European Pharmacopoeia (Ph. Eur.), and British Pharmacopoeia (BP), permitting its use as a humectant, plasticizer, and solvent in oral medications in accordance with the respective pharmacopeial monographs and GMP.^[46]

Environmental impact

Triacetin exhibits favorable biodegradability in environmental compartments, primarily through hydrolysis to glycerol and acetic acid, both of which are naturally occurring and further biodegradable compounds. In aquatic environments, it is classified as readily biodegradable according to OECD guidelines, achieving 76-82% degradation within 28-29 days in screening tests using activated sludge inoculum. This process occurs via enzymatic hydrolysis facilitated by ubiquitous esterases, ensuring rapid breakdown without accumulation in water bodies.^[47]^[48]^[49] Regarding aquatic toxicity, triacetin demonstrates low hazard potential at environmentally relevant concentrations. Acute toxicity tests show LC50 values exceeding 100 mg/L for fish such as Oryzias latipes over 96 hours, EC50 values of 380 mg/L for invertebrates like Daphnia magna after 48 hours, and growth inhibition EC50 values greater than 100 mg/L for algae such as Selenastrum capricornutum over 72 hours. These thresholds indicate no significant adverse effects on aquatic organisms under typical exposure scenarios, given the compound's rapid degradation and low expected environmental levels.^[50]^[41] The production of triacetin contributes positively to environmental sustainability, as it is increasingly derived from renewable sources like crude glycerol, a byproduct of biodiesel manufacturing, thereby reducing reliance on fossil fuel-based feedstocks and promoting circular economy principles. An estimated soil organic carbon-water partition coefficient (Koc) of 10.5 suggests high mobility and potential leaching to groundwater, but its low volatility—characterized by negligible Henry's law constant—limits atmospheric release and air pollution risks. In soil and water, triacetin has a short environmental half-life due to hydrolysis and biodegradation, minimizing persistence.^[51]^[48]^[41] Despite these attributes, data gaps exist concerning the long-term ecological impacts of large-scale triacetin releases, with most studies focusing on short-term degradation and acute toxicity rather than chronic exposure in diverse ecosystems.^[49]

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