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126-73-8

Basic Information
CAS No.: 126-73-8
Name: Tributyl phosphate
Article Data: 121
Molecular Structure:
Molecular Structure of 126-73-8 (Tributyl phosphate)
Formula: C12H27O4P
Molecular Weight: 266.318
Synonyms: Tributilfosfato;Celluphos 4;Butyl phosphate, tri-;1-dibutoxyphosphoryloxybutane;Butyl phosphate, ((BuO)3PO);Phosphoric acid tributyl ester;Tributyle (phosphate de)(FRENCH);Tributylfosfaat;Disflamoll TB;Tributoxyphosphine oxide;TBP;Tributylphosphat;Tri-n-butyl phosphate;Butyl phosphate;TBP Tributyl phosphate;Tributyl phosphate (TBP);
EINECS: 204-800-2
Density: 0.986 g/cm3
Melting Point: -79 °C
Boiling Point: 288.3 °C at 760 mmHg
Flash Point: 193.3 °C
Solubility: 0.6 g/100 mL in water
Appearance: clear liquid
Hazard Symbols: HarmfulXn,FlammableF
Risk Codes: 22-38-40-62-48/20-36/37/38-11
Safety: 36/37-46-45-36/37/39-16-53
Transport Information: UN 1208 3/PG 2
PSA: 54.57000
LogP: 4.54460
Synthetic route
71-36-3

butan-1-ol

126-73-8

phosphoric acid tributyl ester

Conditions
ConditionsYield
With oxygen; phosphan; copper dichloride at 24.9℃; Rate constant; Product distribution; other acohols and reagents, var. concentration of reagents and temperatures;100%
With oxygen; phosphan; copper dichloride at 24.9℃;100%
With oxygen; copper dichloride at 59.9℃;100%
71-36-3

butan-1-ol

A

126-73-8

phosphoric acid tributyl ester

B

109-69-3

n-Butyl chloride

Conditions
ConditionsYield
With hydrogenchloride; water; oxygen; copper dichloride at 59.9℃; Product distribution; Mechanism; other alcohols, var. conc. of reagents, var. temperat.;A 100%
B n/a
With phosphan; chlorine Rate constant; Thermodynamic data; Ea, ΔS(excit.); also in the presence of pyridine;
2372-45-4

sodium butanolate

126-73-8

phosphoric acid tributyl ester

Conditions
ConditionsYield
With trichlorophosphate In butan-1-ol at 10 - 30℃; for 1.83333h;98%
With diethyl ether; trichlorophosphate; butan-1-ol at 0℃;
71-36-3

butan-1-ol

A

1809-19-4

dibutyl hydrogen phosphite

B

126-73-8

phosphoric acid tributyl ester

Conditions
ConditionsYield
With sodium hypophosphite; copper dichloride at 24.9℃; for 214h;A 5.5%
B 94.5%
With hydrogenchloride; zinc(II) phosphide; iron(III) chloride at 70℃;A 90%
B 9%
With sodium hypophosphite; copper dichloride at 24.9℃; for 173h;A 16.7%
B 87.3%
78-47-7

O,O,O-tributyl phosphorothioate

126-73-8

phosphoric acid tributyl ester

Conditions
ConditionsYield
With ozone In dichloromethane at -75℃;92%
71-36-3

butan-1-ol

A

126-73-8

phosphoric acid tributyl ester

B

109-69-3

n-Butyl chloride

C

142-96-1

dibutyl ether

Conditions
ConditionsYield
With oxygen; phosphan; copper(l) chloride; copper dichloride at 24.9℃; Kinetics; Product distribution; Mechanism; ΔE(excit.), ΔS(excit.); other reagents, other catalysts;A 90%
B n/a
C n/a
With oxygen; phosphan; copper(l) chloride; copper dichloride at 24.9℃;A 90%
B n/a
C n/a
71-36-3

butan-1-ol

A

1623-15-0

n-butyl phosphoric acid

B

126-73-8

phosphoric acid tributyl ester

C

107-66-4

dibutyl phosphate

Conditions
ConditionsYield
With phosphorus; tetraethylammonium iodide In water; acetonitrile electrolysis;A n/a
B 87%
C n/a
542-69-8

1-iodo-butane

107-66-4

dibutyl phosphate

126-73-8

phosphoric acid tributyl ester

Conditions
ConditionsYield
With cesium fluoride In acetonitrile for 6h; Ambient temperature; also with n-butylbromide;86%
71-36-3

butan-1-ol

A

126-73-8

phosphoric acid tributyl ester

B

72095-77-3

butylbis(α-hydroxybutyl)phosphine oxide

Conditions
ConditionsYield
With phosphan; p-benzoquinone at 80℃; Kinetics; Condensation; oxidation;A 15%
B 85%
71-36-3

butan-1-ol

A

126-73-8

phosphoric acid tributyl ester

B

107-66-4

dibutyl phosphate

Conditions
ConditionsYield
With sodium bromate; phosphan at 80℃; Kinetics; Condensation;A 20%
B 80%
With sodium hypophosphite; copper dichloride at 24.9℃; for 4h;A 22.2%
B 77.8%
With phosphorous; air; ruthenium hydroxide trichloride; copper dichloride at 80℃; oxidative alkoxylation;A 33.7%
B 11.3%
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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 0.2 ppm
ACGIH TLV: TWA 0.2 ppm

Analytical Methods

For occupational chemical analysis use NIOSH: Tributyl Phosphate, S208.

Specification

1. Introduction of Tributyl phosphate
Tributyl phosphate, with CAS number of 126-73-8, can be called Tributilfosfato; Celluphos 4 ; Butyl phosphate, tri-; 1-dibutoxyphosphoryloxybutane; Butyl phosphate; Phosphoric acid tributyl ester; tributyl ester; Tributoxyphosphine oxide; TBP Tributyl phosphate; Tributyl phosphate (TBP). Tributyl phosphate, known commonly as TBP, is a solvent and plasticizer for cellulose esters such as nitrocellulose and cellulose acetate. The major uses of TBP in industry are as a component of aircraft hydraulic fluid and as a solvent for extraction and purification of rare earth metals from their ores. Tributyl phosphate is used also in mercerizing liquids, where it improves their wetting properties. Tributyl phosphate is also used as a heat exchange medium. TBP is used in some consumer products such as herbicides and water thinned paints and tinting bases.

2. Properties of Tributyl phosphate
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 12
Polar Surface Area: 54.57Å2
Index of Refraction: 1.43
Molar Refractivity: 69.75 cm3
Molar Volume: 269.8 cm3
Surface Tension: 31.7 dyne/cm
Density: 0.986 g/cm3
Flash Point: 193.3 °C
Enthalpy of Vaporization: 50.64 kJ/mol
Boiling Point: 288.3 °C at 760 mmHg
Vapour Pressure: 0.00409 mmHg at 25°C
Melting point: -79 °C
Water Solubility: 0.6 g/100 mL
Merck :14,9618
BRN: 1710584
Stability: Stable. Combustible. Incompatible with strong oxidizing agents. May be water sensitive
Product Categories: Organics; Functional Materials; Phosphates (Plasticizer); Plasticizer; Organic Building Blocks; Organic Phosphates/Phosphites; Phosphorus Compounds; Alphabetic; TP - TZ;T-Z, Puriss p.a.; Analytical Reagents for General Use; Puriss p.a.; Analytical/Chromatography; Ion Sensor Materials; Plasticizer for ISE

3. Structure Descriptors of Tributyl phosphate
InChI
InChI=1/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H3
Smiles
P(OCCCC)(OCCCC)(OCCCC)=O

4. Toxicity of Tributyl phosphate

1.    

skn-rbt 10 mg/24H

    JIHTAB    Journal of Industrial Hygiene and Toxicology. 26 (1944),269.
2.    

eye-rbt 97 mg

    AJOPAA    American Journal of Ophthalmology. 29 (1946),1363.
3.    

orl-rat LD50:1390 mg/kg

    JTSCDR    Journal of Toxicological Sciences. 5 (1980),270.
4.    

ipr-rat LD50:251 mg/kg

    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 15 (8)(1971),30.
5.    

ivn-rat LDLo:100 mg/kg

    NATUAS    Nature. 179 (1957),154.
6.    

orl-mus LD50:1189 mg/kg

    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 15 (8)(1971),30.
7.    

ihl-mus LC50:1300 mg/m3

    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 15 (8)(1971),30.
8.    

ipr-mus LD50:159 mg/kg

    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 15 (8)(1971),30.
9.    

scu-mus LDLo:3 g/kg

    EDWU**    Beitrag zur Toxikologie Technischer Weichmachungsmittel, Heinrich Eller Dissertation .(Pharmakologischen Institut der Universitat Wurzburg,Germany.: 1937).
10.      

5. Safety Information of Tributyl phosphate
Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion, inhalation, and subcutaneous routes. Experimental reproductive effects. A skin, eye, and mucous membrane irritant. Combustible when exposed to heat or flame. To fight fire, use CO2, dry chemical, fog, mist. When heated to decomposition it emits toxic fumes of POx.
Hazard Codes: Xn,F
Risk Statements: 22-38-40-62-48/22-36/37/38-11
R22:Harmful if swallowed.
R38:Irritating to skin.
R40:Limited evidence of a carcinogenic effect.
R62:Risk of impaired fertility.
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R11:Highly flammable.
Safety Statements: 36/37-46-45-36/37/39-16-53
S36/37:Wear suitable protective clothing and gloves.
S46:If swallowed, seek medical advice immediately and show this container or label.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S16:Keep away from sources of ignition.
S53:Avoid exposure - obtain special instructions before use.
RIDADR: UN 1208 3/PG 2
WGK Germany: 2
RTECS: TC7700000
HS Code: 29190010

6. Preparation of Tributyl phosphate
Tributyl phosphate is manufactured by esterification of orthophosphoric acid with butyl alcohol. A laboratory synthesis proceeds with phosphorus oxychloride:
POCl3 + 3C4H9OH → PO(OC4H9)3 + 3HCl