77-89-4

Basic information

• Product Name: Triethyl acetyl citrate
• Synonyms: 1,2,3-Propanetricarboxylic acid, 2-(acetyloxy)-, triethyl ester;1,2,3-Propanetricarboxylicacid,2-(acetyloxy)-,triethylester;2,3-propanetricarboxylicacid,2-(acetyloxy)-triethylester;ATEC;Citric acid, acetyl triethyl ester;Citric acid, triethyl ester, acetate;citricacid,acetyltriethylester;citricacid,triethylester,acetate
• CAS NO: 77-89-4
• Molecular Formula: C₁₄H₂₂O₈
• Molecular Weight: 318.32
• EINECS: 201-066-5
• Product Categories: Hydroxycarboxylic Acid Esters (Plasticizer);Functional Materials;Plasticizer
• Mol File: 77-89-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: -42°C
• Boiling Point: 228-229 °C100 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.136 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000205mmHg at 25°C
• Refractive Index: n20/D 1.439(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Soluble 1 in 140 of water; miscible with acetone, ethanol, and propan-2-ol.
• BRN: 1804947
• CAS DataBase Reference: Triethyl acetyl citrate(CAS DataBase Reference)
• NIST Chemistry Reference: Triethyl acetyl citrate(77-89-4)
• EPA Substance Registry System: Triethyl acetyl citrate(77-89-4)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 1
• RTECS: GE8225000
• Hazardous Substances Data: 77-89-4(Hazardous Substances Data)

Usage

Chemical Properties

Acetyltriethyl citrate occurs as a clear, odorless, practically colorless oily liquid.

Uses

Different sources of media describe the Uses of 77-89-4 differently. You can refer to the following data:
1. 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.
2. 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.

Production Methods

Acetyltriethyl citrate is prepared by the esterification of citric acid with ethanol followed by acylation with acetic anhydride.

Definition

Aqueous-based pharmaceutical coat- ings.

General Description

Certified pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Triethyl 2-acetylcitrate is widely used in hydrophilic adhesives for medications and in biodegradable composition for papermaking and nonwoven production.

Pharmaceutical Applications

Acetyltriethyl citrate is used to plasticize polymers in formulated pharmaceutical coatings. The coating applications include capsules, tablets, beads and granules for taste masking, immediate release, sustained-release and enteric formulations. It is also used in diffusion-controlled release drug delivery systems.

Safety

Acetyltriethyl citrate is used in oral pharmaceutical formulations and is generally regarded as a nontoxic and nonirritating material. However, ingestion of large quantities may be harmful. LD50 (cat, oral): 8.5 g/kg LD50 (mouse, IP): 1.15 g/kg LD50 (rat, oral): 7 g/kg

storage

Acetyltriethyl citrate should be stored in dry, closed containers at temperatures not exceeding 388℃. When stored in accordance with these conditions, acetyltriethyl citrate is a stable product.

Incompatibilities

Acetyltriethyl citrate is incompatible with strong alkalis and oxidizing materials.

Regulatory Status

Approved in the USA for direct food contact in food films.

InChI:InChI=1/C14H22O8/c1-5-19-11(16)8-14(22-10(4)15,13(18)21-7-3)9-12(17)20-6-2/h5-9H2,1-4H3

Synthetic route

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

Conditions	Yield
With 4-(dimethylamino)pyridine hydrochloride at 110℃; for 8h;	90%
sulfuric acid at 80℃; for 3h;	88%
With H-type zeolite catalyst at 60 - 120℃; under 760.051 Torr; for 2.83333h; Reagent/catalyst; Sealed tube; Inert atmosphere;
unter kontinuierlicher Entfernung der entstehenden Essigsaeure;

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

triethyl O-acetylcitrate (77-89-4) → Diethyl-3-(ethoxycarbonyl)pent-2-endioat (5349-99-5)

Conditions	Yield
at 275℃; for 1.5h;	89%
at 270℃; under 760.051 Torr; for 0.4h;	74%
at 250 - 280℃;

triethyl O-acetylcitrate (77-89-4) → 1 propene 1,2,3 tricarboxylic acid (499-12-7)

Conditions	Yield
at 250 - 280℃; ueberdestilliert die Essigsaeure, dann verseift man mit konz.Salzsaeure und destilliert diese unter vermindertem Druck ab;

triethyl O-acetylcitrate (77-89-4) → 2,6-dihydroxy-isonicotinic acid amide (14533-64-3)

Conditions	Yield
With ammonium hydroxide

triethyl O-acetylcitrate (77-89-4) → acetic acid (64-19-7) + aconitic acid triethyl ester

Conditions	Yield
at 250 - 280℃;

triethyl O-acetylcitrate (77-89-4) + ammonium hydroxide → citrazinamide

triethyl O-acetylcitrate (77-89-4) → Diethyl-2-oxo-2H-pyran-4,5-dicarboxylat (101967-99-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 89 percent / 1.5 h / 275 °C 2: 45 percent / TiCl4, 4-Methylmorpholine / tetrahydrofuran; CCl4 / 20 h / Ambient temperature 3: HCOOH / 1 h / 95 °C View Scheme
Multi-step reaction with 3 steps 1.1: 0.4 h / 270 °C / 760.05 Torr 2.1: titanium tetrachloride / tetrachloromethane; tetrahydrofuran / 0.5 h / 0 °C 2.2: 20 h / 0 - 20 °C 3.1: formic acid / 1 h / 100 °C View Scheme

triethyl O-acetylcitrate (77-89-4) → Diethyl-3-(ethoxycarbonyl)-4-(ethoxymethylen)pent-2-endioat (129256-95-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / 1.5 h / 275 °C 2: 45 percent / TiCl4, 4-Methylmorpholine / tetrahydrofuran; CCl4 / 20 h / Ambient temperature View Scheme

propylamine (107-10-8) + triethyl O-acetylcitrate (77-89-4) → n-propylacetamide (5331-48-6) + (Z)-3-acetyl-5-oxo-N-propylhex-2-enamide (1242516-61-5) + (Z)-3-((propylcarbamoyl)-methylene)-4-oxopentanoic acid (1242516-60-4) + (Z)-3,4-bis(propylcarbamoyl)but-3-enoic acid (1242516-62-6) + 1,2,3-tris(propylcarbamoyl)propyl-2-yl acetate

Conditions	Yield
In methanol at 20℃;

triethyl O-acetylcitrate (77-89-4) + N-butylamine (109-73-9) → N-butylacetamide (1119-49-9) + 1,2,3-tris(butylcarbamoyl)propan-2yl acetate (1242516-63-7)

Conditions	Yield
In methanol at 20℃;

methanol (67-56-1) + triethyl O-acetylcitrate (77-89-4) + tert-butylamine (75-64-9) → trimethyl citrate (1587-20-8) + citric acid triethyl ester (77-93-0) + dimethyl 3-(tertbutylcarbamoyl)-3-acetoxy-pentanedioate (1242516-65-9) + 3-(tertbutylcarbamoyl)-3-acetoxy-pentanedioic acid (1242516-64-8)

Conditions	Yield
at 20℃;

triethyl O-acetylcitrate (77-89-4) → triethyl 4-ethoxybuta-1,3-diene-1,2,3-tricarboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 0.4 h / 270 °C / 760.05 Torr 2.1: titanium tetrachloride / tetrachloromethane; tetrahydrofuran / 0.5 h / 0 °C 2.2: 20 h / 0 - 20 °C View Scheme

Upstream product

• 77-93-0 citric acid triethyl ester 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 499-12-7 1 propene 1,2,3 tricarboxylic acid 
• 5349-99-5 Diethyl-3-(ethoxycarbonyl)pent-2-endioat 
• 14533-64-3 2,6-dihydroxy-isonicotinic acid amide 
• 1587-20-8 trimethyl citrate 
• 77-93-0 citric acid triethyl ester 
• 1242516-65-9 dimethyl 3-(tertbutylcarbamoyl)-3-acetoxy-pentanedioate 
• 1242516-64-8 3-(tertbutylcarbamoyl)-3-acetoxy-pentanedioic acid 
• 1119-49-9 N-butylacetamide 
• 1242516-63-7 1,2,3-tris(butylcarbamoyl)propan-2yl acetate 
• 5331-48-6 n-propylacetamide 
• 1242516-61-5 (Z)-3-acetyl-5-oxo-N-propylhex-2-enamide 
• 1242516-60-4 (Z)-3-((propylcarbamoyl)-methylene)-4-oxopentanoic acid 
• 1242516-62-6 (Z)-3,4-bis(propylcarbamoyl)but-3-enoic acid 

Relevant articles and documents

manufacturing method of acetyl-triethyl citrate using solid acid catalysts

The present invention relates to a method for producing acetyl triethyl citrate using a solid acid catalyst and, more specifically, to a method for producing acetyl triethyl citrate capable of increasing conversion rate of reactants while improving yield of acetyl triethyl citrate using zeolite as a catalyst. To this end, the method for producing the acetyl triethyl citrate comprises the following steps: an insertion step for inserting triethyl citrate and acetic anhydride into a reactor; and a reaction step for producing acetyl triethyl citrate by carrying out a reaction between triethyl citrate and acetic anhydride in the presence of the solid acid catalyst.COPYRIGHT KIPO 2017

SKIN EXTERNAL PREPARATIONS AND COSMETICS

An object of the present invention is to provide skin external preparations and cosmetics which contain a branched acyl carnitine and have excellent formulation stability. A skin external preparation of the present invention includes a carnitine derivative represented by the following Formula (1) and/or a carnitine derivative salt represented by the following Formula (2), and an amphoteric surfactant. In Formula (1), R1 and R2 are each independently a C1-18 optionally branched, saturated or unsaturated aliphatic hydrocarbon group. In Formula (2), R1 and R2 are the same as in Formula (1), X? is a specific anion and Y+ is a specific cation.