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| CAS No.: | 77-93-0 |
|---|---|
| Name: | Triethyl citrate |
| Molecular Structure: | |
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| 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 |
| PSA: | 99.13000 |
| LogP: | 0.18700 |
| Conditions | Yield |
|---|---|
| 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% |
diethyl 1,3-acetonedicarboxylate
formic acid ethyl ester
citric acid triethyl ester
| Conditions | Yield |
|---|---|
| With potassium hydroxide |
ethanol
((S)-4-Methoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid
citric acid triethyl ester
| Conditions | Yield |
|---|---|
| With sodium ethanolate Ambient temperature; Yield given; |
| Conditions | Yield |
|---|---|
| With triethylamine Heating; Yield given; |
diethyl 1,3-acetonedicarboxylate
formic acid ethyl ester
citric acid triethyl ester
| Conditions | Yield |
|---|---|
| dann mit Alkohol; |
| Conditions | Yield |
|---|---|
| at 100℃; in geschlossenem Rohr; |
ethanol
citric acid
A
ethyl citrate
B
citric acid α,α'-diethyl ester
C
citric acid triethyl ester
| Conditions | Yield |
|---|---|
| Amberlyst 15 at 25 - 120℃; for 7 - 16h; Product distribution / selectivity; |
| Conditions | Yield |
|---|---|
| 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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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%.
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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. |
