Triacetin

Base Information

• Chemical Name: Triacetin
• CAS No.: 102-76-1
• Deprecated CAS: 2102168-03-4
• Molecular Formula: C9H14O6
• Molecular Weight: 218.207
• Hs Code.: 29153930
• European Community (EC) Number: 203-051-9,686-191-7
• ICSC Number: 1203
• NSC Number: 757364,4796
• UNII: XHX3C3X673
• DSSTox Substance ID: DTXSID3026691
• Nikkaji Number: J5.010E
• Wikipedia: Triacetin
• Wikidata: Q83253
• NCI Thesaurus Code: C82268
• RXCUI: 10756
• Metabolomics Workbench ID: 8970
• ChEMBL ID: CHEMBL1489254
• Mol file: 102-76-1.mol

Synonyms:Enzactin;Triacetin;Triacetyl glycerol;Triacetyl-glycerol;Triacetylglycerol

Chemical Property of Triacetin

Chemical Property:

• Appearance/Colour: colourless liquid with a bitter taste
• Vapor Pressure: 0.0141mmHg at 25°C
• Melting Point: 3 °C(lit.)
• Refractive Index: n25/D 1.429-1.431(lit.)
• Boiling Point: 258 °C at 760 mmHg
• Flash Point: 93.9 °C
• PSA: 78.90000
• Density: 1.16 g/mL at 25 °C(lit.)
• LogP: 0.04430
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in water, miscible with ethanol (96 per cent) and toluene.
• Water Solubility.: 64.0 g/L (20 ºC)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 218.07903816
• Heavy Atom Count: 15
• Complexity: 229

Purity/Quality:

98% ^*data from raw suppliers

Triacetin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CC(=O)OCC(COC(=O)C)OC(=O)C
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is mildly irritating to the skin.
• 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; it 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. This product 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, a component of cigarette filters, induced a contact dermatitis in a worker at a cigarette manufacturers. Triacetin is a colorless, oily liquid of slight fatty odor and bitter taste. It is soluble with water and is miscible with alcohol and ether. It functions in foods as a humectant and solvent. As fixative in perfumery; solvent in manufacture of celluloid, photographic films. Technical triacetin (a mixture of mono-, di-, and small quantities of triacetin) as a solvent for basic dyes, particularly indulines, and tannin in dyeing.
• Description: § 184.1901(a) Triacetin (C8H14O6), also known as 1,2,3-propanetriol triacetate or glyceryl triacetate, is the triester of glycerin and acetic acid. Triacetin can be prepared by heating glycerin with acetic anhydride alone or in the presence of finely divided potassium hydrogen sulfate. It 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.
• Therapeutic Function: Topical antifungal
• Clinical Use: Glyceryl triacetate (Enzactin, Fungacetin) is a colorless, oilyliquid with a slight odor and a bitter taste. The compound 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.

Technology Process of Triacetin

There total 85 articles about Triacetin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

acetic acid (64-19-7,77671-22-8) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → triacetylglycerol (102-76-1)

Guidance literature:

at 150 ℃; for 0.5h;

Reference yield: 99.0%

acetic anhydride (108-24-7) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → triacetylglycerol (102-76-1)

Guidance literature:

yttria-stabilized zirconia; In acetonitrile; for 8h; Heating;

DOI:10.1055/s-2001-10778

Reference yield: 98.0%

acetyl chloride (75-36-5) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → triacetylglycerol (102-76-1)

Guidance literature:

With aluminum oxide; at 25 ℃; for 1h;

DOI:10.1021/jo035412f

upstream raw materials:

1,2,3-tribromopropane

potassium acetate

silver(I) acetate

acetic anhydride

Downstream raw materials:

water

acetic acid

methylammonium carbonate

acrolein

Refernces

• 1、 Xu, Zichen,Gong, Honghui,Chen, Manyu,Luo, Ruihan,Qian, Wei,Peng, Qingpo,Hou, Zhenshan. "Catalytic hydrogenolysis of glycerol into propyl acetate with ruthenium complexes". . . Retrieved 2019.
• 2、 Adiels, Martin,Larsson, Thomas,Sutton, Pauline,Taskinen, Marja-Riitta,Boren, Jan,Fielding, Barbara A.. "Optimization of N-methyl-N-[tert-butyldimethylsilyl]- trifluoroacetamide as a derivatization agent for determining isotopic enrichment of glycerol in very-low density lipoproteins". . p. 586 - 592. Retrieved 2010.
• 3、 Sánchez, Julián A.,Hernández, Diana L.,Moreno, Jorge A.,Mondragón, Fanor,Fernández, Jhon J.. "Alternative carbon based acid catalyst for selective esterification of glycerol to acetylglycerols". . p. 55 - 60. Retrieved 2011.
• 4、 Zhu, Shanhui,Gao, Xiaoqing,Dong, Fang,Zhu, Yulei,Zheng, Hongyan,Li, Yongwang. "Design of a highly active silver-exchanged phosphotungstic acid catalyst for glycerol esterification with acetic acid". . p. 155 - 163. Retrieved 2013.
• 5、 Leng, Yan,Wang, Jun,Zhu, Dunru,Ren, Xiaoqian,Ge, Hanqing,Shen, Lei. "Heteropolyanion-based ionic liquids: Reaction-induced self-separation catalysts for esterification". . p. 168 - 171. Retrieved 2009.
• 6、 Jeong, Seong-Hee,Joo, Seongjoon,Kim, Kyung-Jin,Kim, Seon-Won,Seo, Hogyun,Sohn, Jung-Hoon,Tseten, Tenzin,Wang, Chonglong,Zada, Bakht. "Metabolic engineering of: Escherichia coli for production of non-natural acetins from glycerol". . p. 7788 - 7802. Retrieved 2020.
• 7、 Testa, Maria Luisa,La Parola, Valeria,Liotta, Leonarda F.,Venezia, Anna Maria. "Screening of different solid acid catalysts for glycerol acetylation". . p. 69 - 76. Retrieved 2013.
• 8、 Altino, Felyppe M. R. S.,Bortoluzzi, Janaína H.,Meneghetti, Simoni M. P.,da Silva, Débora S.. "Investigation of Sn(IV) catalysts in glycerol acetylation". . . Retrieved 2020.
• 9、 Whalen. "-". . p. 4973. Retrieved 1978.
• 10、 Leng, Yan,Zhao, Jiwei,Jiang, Pingping,Lu, Dan. "POSS-derived solid acid catalysts with excellent hydrophobicity for highly efficient transformations of glycerol". . p. 875 - 881. Retrieved 2016.