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77-94-1

Basic Information
CAS No.: 77-94-1
Name: 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-tributyl ester
Molecular Structure:
Molecular Structure of 77-94-1 (1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-tributyl ester)
Formula: C18H32O7
Molecular Weight: 360.50
Synonyms: 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, tributyl ester (9CI);Citric acid, tributyl ester (6CI,7CI,8CI);2-Hydroxy-1,2,3-propanetricarboxylic acid tributyl ester;Butyl citrate;Citroflex 4;Citroflex C 4;Morflex TBC;NSC 8491;Tri-n-butyl citrate;
EINECS: 201-071-2
Density: 1.041 g/cm3
Melting Point: ≥300 °C(lit.)
Boiling Point: 389.8 °C at 760 mmHg
Flash Point: 120.7 °C
Solubility: insoluble in water
Appearance: clear liquid
Hazard Symbols: ToxicT
Risk Codes: 25
Safety: 26-36/37/39-45-24/25
Transport Information: UN 2811 6.1/PG 2
PSA: 99.13000
LogP: 2.52760
Synthetic route
77-92-9

citric acid

71-36-3

butan-1-ol

77-94-1

Citroflex-4

Conditions
ConditionsYield
With 1,3-propanesultone; sulfuric acid; manganese(II) acetate; Cycloheximide In water; toluene at 65 - 100℃; for 31h; Temperature; Ionic liquid;98.6%
With dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 24h;97%
With 3H(1+)*O40SiW12(4-)*C21H22O3PS(1+) Concentration; Reflux; Dean-Stark;97.5%
7664-93-9

sulfuric acid

77-92-9

citric acid

71-36-3

butan-1-ol

77-94-1

Citroflex-4

Conditions
ConditionsYield
at 150℃; sowie bei 175grad und 200grad;
77-92-9

citric acid

71-36-3

butan-1-ol

A

118068-28-3

monobutyl citrate

B

142-96-1

dibutyl ether

C

77-94-1

Citroflex-4

D

101996-65-0

sym-di-n-butyl citrate

Conditions
ConditionsYield
Amberlyst 15 at 25 - 120℃; for 16h;
298-12-4

Glyoxilic acid

71-36-3

butan-1-ol

A

105-76-0

Dibutyl maleate

B

2050-60-4

di-n-butyl oxalate

C

141-03-7

dibutyl succinate

D

1587-18-4

L-(-)-di-n butyl malate

E

344268-32-2

dibutyl tartrate

F

38094-11-0

propane-1,2,3-tricarboxylic acid tributyl ester

G

77-94-1

Citroflex-4

H

105-75-9

dibutyl fumarate

I

117538-83-7

C11H20O5

J

94086-70-1

C12H22O4S3

Conditions
ConditionsYield
Stage #1: Glyoxilic acid With sodiumsulfide nonahydrate In water at 90℃; for 168h;
Stage #2: butan-1-ol With hydrogenchloride at 90℃; for 2h;
109-69-3

n-Butyl chloride

68-04-2

sodium citrate

77-94-1

Citroflex-4

Conditions
ConditionsYield
Stage #1: n-Butyl chloride With potassium iodide In acetone for 2h; Inert atmosphere; Reflux;
Stage #2: sodium citrate In N,N-dimethyl-formamide at 60℃; for 3h; Temperature;
77-94-1

Citroflex-4

108-24-7

acetic anhydride

77-90-7

acetyltributyl citrate

Conditions
ConditionsYield
dmap at 100℃; for 24h;93%
With 1-butyl-3-methylimidazolium 4-methylbenzenenesulfonate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 50℃; for 8h;19%
at 70 - 80℃; Concentration;
108-05-4

vinyl acetate

77-94-1

Citroflex-4

77-90-7

acetyltributyl citrate

Conditions
ConditionsYield
With potassium tert-butylate; 1-ethyl-3-methylimidazolium tetrafluoroborate In tetrahydrofuran at 70℃; for 12h; Reagent/catalyst; Solvent; Time; Temperature; Concentration; Inert atmosphere;81%
77-94-1

Citroflex-4

64-19-7

acetic acid

77-90-7

acetyltributyl citrate

Conditions
ConditionsYield
[Mes2NH2](+)[O3SC6F5](-) In n-heptane at 115℃; for 48h;31%
77-94-1

Citroflex-4

343599-72-4

1-propene-1,2,3-tricarboxylic acid tributyl ester

Conditions
ConditionsYield
With phosphoric acid; acetic anhydride at 155℃; durch Leiten des Reaktionsprodukts durch ein auf 425grad erhitztes Rohr;
With sulfuric acid; acetic anhydride at 155℃; durch Leiten des Reaktionsprodukts durch ein auf 425grad erhitztes Rohr;
77-94-1

Citroflex-4

111-27-3

hexan-1-ol

16544-70-0

tri-n-hexyl citrate

Conditions
ConditionsYield
aluminium(III) triflate at 150 - 195℃; under 37.5038 - 7500.75 Torr; Conversion of starting material;
77-94-1

Citroflex-4

C22H35ClO9

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrachloromethane / 4 h / 70 °C / Inert atmosphere
2: phosphorus trichloride / 60 °C
View Scheme
108-30-5

succinic acid anhydride

77-94-1

Citroflex-4

C22H36O10

Conditions
ConditionsYield
In tetrachloromethane at 70℃; for 4h; Inert atmosphere;
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77-90-7
16544-70-0
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    77-94-1

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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

PURITY: 99.0% min
CITRIC ACID 0.2% max
MOISTURE: 0.2% max
HEAVY METALS: 10ppm max
COLOR , APHA: 50 max

Specification

The IUPAC name of Tri-n-butyl citrate is tributyl 2-hydroxypropane-1,2,3-tricarboxylate. With the CAS registry number 77-94-1, it is also named as 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, tributyl ester. The product's categories are Functional Materials; Hydroxycarboxylic Acid Esters (Plasticizer); Plasticizer; Amino Ester. It is clear liquid which is insoluble in water, soluble in methanol, acetone, carbon tetrachloride, acetic acid, castor oil, mineral oil and other organic solvent. When heated to decomposition it emits acrid smoke and irritating vapors. Additionally, this chemical can be obtained by citric acid and n-butyl alcohol at the present of sulfuric acid.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.68; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.68; (4)ACD/LogD (pH 7.4): 4.68; (5)ACD/BCF (pH 5.5): 2124.92; (6)ACD/BCF (pH 7.4): 2124.65; (7)ACD/KOC (pH 5.5): 8381.24; (8)ACD/KOC (pH 7.4): 8380.19; (9)#H bond acceptors: 7; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 18; (12)Index of Refraction: 1.465; (13)Molar Refractivity: 92.26 cm3; (14)Molar Volume: 333.6 cm3; (15)Polarizability: 36.57×10-24 cm3; (16)Surface Tension: 39 dyne/cm; (17)Enthalpy of Vaporization: 73.91 kJ/mol; (18)Vapour Pressure: 1.09E-07 mmHg at 25°C; (19)Rotatable Bond Count: 17; (20)Exact Mass: 360.214803; (21)MonoIsotopic Mass: 360.214803; (22)Topological Polar Surface Area: 99.1; (23)Heavy Atom Count: 25; (24)Complexity: 382.

Uses of Tri-n-butyl citrate: It is used as GC stationary liquid, plastic, toughening agents of plastic, foam remover and solvent of cellulose nitrate. It is also used as plasticizer of polyvinyl chloride, polyethylene copolymer and cellulose resin. 

When you are using this chemical, please be cautious about it as the following:
It is toxic if swallowed. People should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OCCCC)CC(O)(C(=O)OCCCC)CC(=O)OCCCC
2. InChI:InChI=1/C18H32O7/c1-4-7-10-23-15(19)13-18(22,17(21)25-12-9-6-3)14-16(20)24-11-8-5-2/h22H,4-14H2,1-3H3

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 2900mg/kg (2900mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: OTHER CHANGES
Journal of Pharmaceutical Sciences. Vol. 53, Pg. 774, 1964.