Triethyl citrate supplier

Name
Triethyl citrate
EINECS 201-070-7
CAS No. 77-93-0
Article Data31
CAS DataBase
Density 1.177 g/cm³
Solubility 5.7 g/100 mL (25 °C) in water
Melting Point -46 °C
Formula C₁₂H₂₀O₇
Boiling Point 294 °C at 760 mmHg
Molecular Weight 276.287
Flash Point 95.4 °C
Transport Information
Appearance clear liquid
Safety 24/25
Risk Codes 20
Molecular Structure
Hazard Symbols Xn
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;
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

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%

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 109-94-4
formic acid ethyl ester

: 77-93-0
citric acid triethyl ester

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 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

...Expand

: 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

Conditions	Yield
dann mit Alkohol;

...Expand

: 75-03-6
ethyl iodide

citrate silver: citrate silver

: 77-93-0
citric acid triethyl ester

Conditions

Conditions	Yield
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

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

...Expand

: 144-16-1
5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid)

: 77-93-0
citric acid triethyl ester

Conditions

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

: 112535-39-4
(5-oxo-[1,3]dioxolane-4,4-diyl)-bis-acetic acid diethyl ester

: 77-93-0
citric acid triethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pig liver esterase, aq. phosphate buffer pH=7, aq. NaOH / 2 h / Ambient temperature 2: Et3N / Heating View Scheme

: 77862-72-7
(5-oxo-[1,3]dioxolane-4,4-diyl)-bis-acetic acid dimethyl ester

: 77-93-0
citric acid triethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pig liver esterase, aq. phosphate buffer pH=7, aq. NaOH / 2 h / Ambient temperature 2: EtONa / Ambient temperature View Scheme

: 67-56-1
methanol

: 77-89-4
triethyl O-acetylcitrate

: 75-64-9
tert-butylamine

A: 1587-20-8
trimethyl citrate

B: 77-93-0
citric acid triethyl ester

C: 1242516-65-9
dimethyl 3-(tertbutylcarbamoyl)-3-acetoxy-pentanedioate

D: 1242516-64-8
3-(tertbutylcarbamoyl)-3-acetoxy-pentanedioic acid

Conditions

Conditions	Yield
at 20℃;

...Expand

: 64-17-5
ethanol

: 77-92-9
citric acid

A: 4676-51-1
Diethyl 2-methylsuccinate

B: 77-93-0
citric acid triethyl ester

Conditions

Conditions	Yield
With hydrogen In water at 200℃; under 3000.3 Torr; for 6h;	A 19 %Spectr. B n/a

...Expand

: 107-10-8
propylamine

: 77-93-0
citric acid triethyl ester

: 367493-05-8
2-hydroxy-N1,N2,N3-tripropylpropane-1,2,3-tricarboxamide

Conditions

Conditions	Yield
In methanol at 20℃;	96%

: 77-93-0
citric acid triethyl ester

: 109-73-9
N-butylamine

: 38328-55-1
N1,N2,N3-tributyl-2-hydroxypropane-1,2,3-tricarboxamide

Conditions

Conditions	Yield
In methanol at 20℃;	93%

: 77-93-0
citric acid triethyl ester

: 108-24-7
acetic anhydride

: 77-89-4
triethyl O-acetylcitrate

Conditions

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;

: 77-93-0
citric acid triethyl ester

: 93-97-0
benzoic acid anhydride

: 145867-24-9
C19H24O8

Conditions

Conditions	Yield
With 4-(dimethylamino)pyridine hydrochloride at 110℃; for 28h;	88%

: 77-93-0
citric acid triethyl ester

: 302962-49-8
dasatanib

: C22H26ClN7O2S*C12H20O7

Conditions

Conditions	Yield
In methanol at 20℃; for 3h;	86%

: 77-93-0
citric acid triethyl ester

: 18960-42-4
2-hydroxypropane-1,2,3-tricarbohydrazide

Conditions

Conditions	Yield
With hydrazine hydrate In methanol for 6h; Reflux;	85%
With ethanol; hydrazine hydrate

: 77-93-0
citric acid triethyl ester

: 101996-63-8
citric acid α,α'-diethyl ester

Conditions

Conditions	Yield
With sodium hydroxide; chymotripsin; phosphate buffer pH=7 for 96h; Ambient temperature;	85%

: 77-93-0
citric acid triethyl ester

: 920-46-7
Methacryloyl chloride

: 186351-92-8
C16H24O8

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; triethylamine In toluene at 0 - 20℃; for 4h; Inert atmosphere;	82%

added-triethylcitrate: added-triethylcitrate

: 60-29-7
diethyl ether

: 77-93-0
citric acid triethyl ester

: 78-81-9
isobutylamine

: 367493-06-9
N,N',N"-tri-iso-butylcitramide

Conditions

Conditions	Yield
In methanol	80.3%

...Expand

: 77-93-0
citric acid triethyl ester

: 753-55-9
dimethyl aluminum fluoride

: 252270-77-2
[(C(CH2COOC2H5)2(COOC2H5)O)AlF(CH3)]2

Conditions

Conditions	Yield
In toluene byproducts: CH4; N2-atmosphere; dropwise addn. of citrate ester to 1 equiv. Al-compd. at room temp., stirring for 24 h; crystn. (-20°C); further crop on concn. of mother liquor; elem. anal.;	63%

: 60-29-7
diethyl ether

: 77-93-0
citric acid triethyl ester

: 38328-55-1
N1,N2,N3-tributyl-2-hydroxypropane-1,2,3-tricarboxamide

Conditions

Conditions	Yield
With N-butylamine In methanol	58%

: 60-29-7
diethyl ether

: 77-93-0
citric acid triethyl ester

: 367493-05-8
2-hydroxy-N1,N2,N3-tripropylpropane-1,2,3-tricarboxamide

Conditions

Conditions	Yield
With propylamine In methanol	55%

: 77-93-0
citric acid triethyl ester

: 6-(benzyloxy)-1,3-dimethyl-1,3,5-triazine-2,4(1H,3H)-dione

: 112031-19-3
triethyl 2-benzyloxy-1,2,3-propanetricarboxylate

Conditions

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane at 50℃; for 11h; Molecular sieve; Inert atmosphere;	55%

: 107-85-7
1-amino-3-methylbutane

: 60-29-7
diethyl ether

: 77-93-0
citric acid triethyl ester

: 367493-07-0
N,N',N''-triisopentyl citramide

Conditions

Conditions	Yield
In methanol	52.1%

...Expand

5%MeOH: 5%MeOH

: 77-93-0
citric acid triethyl ester

: 19958-02-2
3-Hydroxy-3,4-bis(ethoxycarbonyl)butanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; acetic acid In methanol; ethanol; water	38%

: 77-93-0
citric acid triethyl ester

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 112031-19-3
triethyl 2-benzyloxy-1,2,3-propanetricarboxylate

Conditions

Conditions	Yield
trifluorormethanesulfonic acid In dichloromethane; cyclohexane for 2.5h; Ambient temperature;	5%

: 77-93-0
citric acid triethyl ester

: 18852-51-2
sodium cyanoacetic acid ethyl ester

: 861310-20-5
1-cyano-butane-1,2,3,4-tetracarboxylic acid tetraethyl ester

Conditions

Conditions	Yield
With ethanol

: 77-93-0
citric acid triethyl ester

: 18852-51-2
sodium cyanoacetic acid ethyl ester

: 1703-61-3
rac-4-oxocyclopentane-1,2-dicarboxylic acid

Conditions

Conditions	Yield
With ethanol Verseifung des neben 1-Cyan-butan-tetracarbonsaeure-(1.2.3.4)-tetraaethylester entstehenden Produkts mit Schwefelsaeure;

: 77-93-0
citric acid triethyl ester

: 4552-01-6
citric acid β-ethyl ester

Conditions

Conditions	Yield
Verseifung;
With sodium hydroxide; Petroleum ether

: 77-93-0
citric acid triethyl ester

: 19958-02-2
3-Hydroxy-3,4-bis(ethoxycarbonyl)butanoic acid

Conditions

Conditions	Yield
With sodium hydroxide durch fraktionierte Verseifung;
With sodium hydroxide; Petroleum ether at 0℃;

: 77-93-0
citric acid triethyl ester

: 5349-99-5
Diethyl-3-(ethoxycarbonyl)pent-2-endioat

Conditions

Conditions	Yield
With phosphorus trichloride Destillation des Reaktionsproduktes;
With phosphorus pentachloride Destillation des Reaktionsproduktes;
Multi-step reaction with 2 steps 1: 88 percent / H2SO4 / 3 h / 80 °C 2: 89 percent / 1.5 h / 275 °C View Scheme

: 77-93-0
citric acid triethyl ester

: sulfurous acid bis-(1,2-bis-ethoxycarbonyl-1-ethoxycarbonylmethyl-ethyl ester)

Conditions

Conditions	Yield
With pyridine; thionyl chloride; diethyl ether at 10℃;

: 77-93-0
citric acid triethyl ester

: (4-hydroxy-3,6-dioxo-hexahydro-pyridazin-4-yl)-acetic acid hydrazide

Conditions

Conditions	Yield
With hydrazine hydrate

: 77-93-0
citric acid triethyl ester

: 103-71-9
phenyl isocyanate

: 2-phenylcarbamoyloxy-propane-1,2,3-tricarboxylic acid triethyl ester

Conditions

Conditions	Yield
at 130℃;

: 77-93-0
citric acid triethyl ester

: 75-36-5
acetyl chloride

: 77-89-4
triethyl O-acetylcitrate

: 77-93-0
citric acid triethyl ester

: 2524-64-3
chlorophosphoric acid diphenyl ester

: 102089-54-3
2-diphenoxyphosphoryloxy-propane-1,2,3-tricarboxylic acid triethyl ester

Conditions

Conditions	Yield
With pyridine

: 67-56-1
methanol

: 77-93-0
citric acid triethyl ester

: 64670-05-9
lithium sodium dianion of methyl acetoacetate

: 107182-07-0
methyl 1,8-dihydroxy-6-(ethoxycarbonyl)-2-(methoxycarbonyl)-3-naphthylacetate

Conditions

Conditions	Yield
With calcium acetate 1.) THF, 0 deg C, 2 h; 2.) reflux, 2 h; Yield given. Multistep reaction;

...Expand

: 77-93-0
citric acid triethyl ester

: 105-45-3
acetoacetic acid methyl ester

: 107182-07-0
methyl 1,8-dihydroxy-6-(ethoxycarbonyl)-2-(methoxycarbonyl)-3-naphthylacetate

Conditions

Conditions	Yield
With n-butyllithium; calcium acetate; sodium hydride 1.) THF, hexane, 1 h, room temperature, 2.) MeOH, 2 h, reflux; Yield given. Multistep reaction;

Triethyl citrate Consensus Reports

Reported in EPA TSCA Inventory.

Triethyl citrate 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.

Product Name

Triethyl citrate

Synthetic route

Triethyl citrate Consensus Reports

Triethyl citrate Specification

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