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77-93-0

Basic Information
CAS No.: 77-93-0
Name: 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-triethyl ester
Article Data: 31
Cas Database
Molecular Structure:
Molecular Structure of 77-93-0 (1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-triethyl ester)
Formula: C12H20O7
Molecular Weight: 276.287
Synonyms: 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, triethyl ester (9CI);Citric acid, triethyl ester (6CI,7CI,8CI);Citroflex 2;Citroflex C 2;Citroflex EC;Citroflex SC 60;Citrofol A 1;Citrofol AI;Ethyl citrate;Eudraflex;Hydragen CAT;Morflex C 2;Morflex TEC;NSC 8907;
EINECS: 201-070-7
Density: 1.177 g/cm3
Melting Point: -46 °C
Boiling Point: 294 °C at 760 mmHg
Flash Point: 95.4 °C
Solubility: 5.7 g/100 mL (25 °C) in water
Appearance: clear liquid
Hazard Symbols: Xn
Risk Codes: 20
Safety: 24/25
Transport Information: N/A
PSA: 99.13000
LogP: 0.18700
Synthetic route
64-17-5

ethanol

77-92-9

citric acid

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
Stage #1: ethanol With dicyclohexyl-carbodiimide at 20℃; for 36h; Large scale;
Stage #2: citric acid at 35℃; for 6h; Temperature; Autoclave; Large scale;
96%
With sulfonated graphene In neat (no solvent) at 90℃; for 4h;94%
With boric acid; benzenesulfonic acid at 85 - 90℃; for 3h;93.26%
105-50-0

diethyl 1,3-acetonedicarboxylate

109-94-4

formic acid ethyl ester

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
With potassium hydroxide
64-17-5

ethanol

199341-50-9

((S)-4-Methoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
With sodium ethanolate Ambient temperature; Yield given;
64-17-5

ethanol

((S)-4-Ethoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
With triethylamine Heating; Yield given;
105-50-0

diethyl 1,3-acetonedicarboxylate

109-94-4

formic acid ethyl ester

KOH

KOH

77-93-0

citric acid triethyl ester

109-94-4

formic acid ethyl ester

acetone-dicarboxylic acid-(1.3)-diethyl ester

acetone-dicarboxylic acid-(1.3)-diethyl ester

KOH

KOH

77-93-0

citric acid triethyl ester

10026-13-8, 874483-75-7

phosphorus pentachloride

77-92-9

citric acid

A

77-93-0

citric acid triethyl ester

B

aconitic acid chloride

aconitic acid chloride

Conditions
ConditionsYield
dann mit Alkohol;
75-03-6

ethyl iodide

citrate silver

citrate silver

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
at 100℃; in geschlossenem Rohr;
64-17-5

ethanol

77-92-9

citric acid

A

4552-00-5

ethyl citrate

B

101996-63-8

citric acid α,α'-diethyl ester

C

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
Amberlyst 15 at 25 - 120℃; for 7 - 16h; Product distribution / selectivity;
144-16-1

5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid)

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / dimethoxypropane, Dowex 50WX4, MeOH / 24 h / Heating
2: pig liver esterase, aq. phosphate buffer pH=7, aq. NaOH / 2 h / Ambient temperature
3: EtONa / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 85 percent / diethoxypropane, Dowex 50WX4, MeOH / 24 h / Heating
2: pig liver esterase, aq. phosphate buffer pH=7, aq. NaOH / 2 h / Ambient temperature
3: Et3N / Heating
View Scheme
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of Triethyl citrate is triethyl 2-hydroxypropane-1,2,3-tricarboxylate. With the CAS registry number 77-93-0, it is also named as 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, triethyl ester. The product's categories are Functional Materials; Hydroxycarboxylic Acid Esters (Plasticizer); Plasticizer; Amino Ester. It is clear liquid which is soluble in most organic solvents and insoluble in oils. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.49; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.49; (4)ACD/LogD (pH 7.4): 1.49; (5)ACD/BCF (pH 5.5): 8.02; (6)ACD/BCF (pH 7.4): 8.02; (7)ACD/KOC (pH 5.5): 154.52; (8)ACD/KOC (pH 7.4): 154.51; (9)#H bond acceptors: 7; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 12; (12)Index of Refraction: 1.461; (13)Molar Refractivity: 64.46 cm3; (14)Molar Volume: 234.6 cm3; (15)Polarizability: 25.55×10-24 cm3; (16)Surface Tension: 41.5 dyne/cm; (17)Enthalpy of Vaporization: 61.91 kJ/mol; (18)Vapour Pressure: 0.000175 mmHg at 25°C; (19)Rotatable Bond Count: 11; (20)Exact Mass: 276.120903; (21)MonoIsotopic Mass: 276.120903; (22)Topological Polar Surface Area: 99.1; (23)Heavy Atom Count: 19; (24)Complexity: 304.

Preparation of Triethyl citrate: It can be obtained by esterification of citric acid and alcohol in the presence of sulfuric acid.

Uses of Triethyl citrate: It is mainly used as plasticizer of cellulose, vinyl and other thermoplastic resin. It is also used as solvent, flavoring agent and chelating agent. In addition, it can react with acetic acid anhydride to get 2-acetoxy-propane-1,2,3-tricarboxylic acid triethyl ester. This reaction needs catalytic agent sulfuric acid at temperature of 80 °C. The reaction time is 3 hours. The yield is 88%.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(CC(O)(CC(=O)OCC)C(=O)OCC)OCC
2. InChI:InChI=1/C12H20O7/c1-4-17-9(13)7-12(16,11(15)19-6-3)8-10(14)18-5-2/h16H,4-8H2,1-3H3

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 3500mg/kg (3500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Food and Cosmetics Toxicology. Vol. 17, Pg. 389, 1979.
guinea pig LD50 oral > 25mL/kg (25mL/kg)   German Offenlegungsschrift Patent Document. Vol. #2703360,
mouse LD50 intraperitoneal 1750mg/kg (1750mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: OTHER CHANGES
Journal of Pharmaceutical Sciences. Vol. 53, Pg. 774, 1964.
 
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 389, 1979.
rat LC50 inhalation 1300ppm/6H (1300ppm) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
"Industrial Hygiene and Toxicology," 2nd ed., Patty, F.A., ed., New York, John Wiley & Sons, Inc., 1958-63Vol. 2, Pg. 1892, 1963.
rat LD50 intraperitoneal 4gm/kg (4000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 214, 1985.
rat LD50 oral 5900mg/kg (5900mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 214, 1985.
rat LD50 subcutaneous 6600mg/kg (6600mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 214, 1985.