Acetyl triethyl citrate

Base Information

• Chemical Name: Acetyl triethyl citrate
• CAS No.: 77-89-4
• Molecular Formula: C14H22O8
• Molecular Weight: 318.324
• Hs Code.: 2918150000
• European Community (EC) Number: 201-066-5
• NSC Number: 3887
• UNII: 5WBR36T90E
• DSSTox Substance ID: DTXSID5044576
• Nikkaji Number: J10.678J
• Wikidata: Q27262956
• RXCUI: 1311603
• ChEMBL ID: CHEMBL2105928
• Mol file: 77-89-4.mol

Synonyms:1,2,3-Propanetricarboxylic acid, 2-(acetyloxy)-, triethyl ester;Triethyl 2-acetoxy-1,2,3-propanetricarboxylate;triethyl 2-acetylcitrate;acetyl triethyl citrate

Chemical Property of Acetyl triethyl citrate

Chemical Property:

• Appearance/Colour: colorless or light yellow liquid
• Vapor Pressure: 0.000205mmHg at 25°C
• Melting Point: -42 °C
• Refractive Index: n20/D 1.439(lit.)
• Boiling Point: 327.2 °C at 760 mmHg
• Flash Point: 136.9 °C
• PSA: 105.20000
• Density: 1.163 g/cm³
• LogP: 0.75780
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Soluble 1 in 140 of water; miscible with acetone, ethanol, and propan-2-ol.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 13
• Exact Mass: 318.13146766
• Heavy Atom Count: 22
• Complexity: 395

Purity/Quality:

98%, ^*data from raw suppliers

O-Acetyl- ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(CC(=O)OCC)(C(=O)OCC)OC(=O)C
• Uses: ATEC is produced by the reaction of citric acid triethyl ester with acetic acid anhydride. It is used as a solvent plasticizer for cellulose nitrate and cellulose acetate. Triethyl O-Acetylcitrate is used in the preparation of poly(lactic) acid biodegradable and flexible films, acting as a plasticizer. Also used in the synthesis of control-release capsules containing polymeric coatings.

Technology Process of Acetyl triethyl citrate

There total 3 articles about Acetyl triethyl citrate 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: 90.0%

citric acid triethyl ester (77-93-0) + acetic anhydride (108-24-7) → triethyl O-acetylcitrate (77-89-4)

Guidance literature:

With 4-(dimethylamino)pyridine hydrochloride; at 110 ℃; for 8h;

DOI:10.1021/ol4030875

Reference yield:

citric acid triethyl ester (77-93-0) + acetyl chloride (75-36-5) → triethyl O-acetylcitrate (77-89-4)

Guidance literature:

Reference yield:

→ triethyl O-acetylcitrate (77-89-4)

Guidance literature:

upstream raw materials:

citric acid triethyl ester

acetic anhydride

acetyl chloride

Downstream raw materials:

trimethyl citrate

citric acid triethyl ester

dimethyl 3-(tertbutylcarbamoyl)-3-acetoxy-pentanedioate

3-(tertbutylcarbamoyl)-3-acetoxy-pentanedioic acid

Refernces

• 1、 Liu, Zhihui,Ma, Qiaoqiao,Liu, Yuxiu,Wang, Qingmin. "4-(N,N -dimethylamino)pyridine hydrochloride as a recyclable catalyst for acylation of inert alcohols: Substrate scope and reaction mechanism". supporting information. p. 236 - 239. Retrieved 2014/01/23.
• 2、 Kvita, Vratislav. "Synthesis of 2-Oxo-2H-pyran-5-carboxylate Derivatives". . p. 411 - 416. Retrieved 2007/10/02.