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CAS No.: | 126-73-8 |
---|---|
Name: | Tributyl phosphate |
Article Data: | 121 |
Molecular Structure: | |
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: | Xn,F |
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 |
Conditions | Yield |
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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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With trichlorophosphate In butan-1-ol at 10 - 30℃; for 1.83333h; | 98% |
With diethyl ether; trichlorophosphate; butan-1-ol at 0℃; |
Conditions | Yield |
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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% |
Conditions | Yield |
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With ozone In dichloromethane at -75℃; | 92% |
butan-1-ol
A
phosphoric acid tributyl ester
B
n-Butyl chloride
C
dibutyl ether
Conditions | Yield |
---|---|
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 |
butan-1-ol
A
n-butyl phosphoric acid
B
phosphoric acid tributyl ester
C
dibutyl phosphate
Conditions | Yield |
---|---|
With phosphorus; tetraethylammonium iodide In water; acetonitrile electrolysis; | A n/a B 87% C n/a |
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile for 6h; Ambient temperature; also with n-butylbromide; | 86% |
butan-1-ol
A
phosphoric acid tributyl ester
B
butylbis(α-hydroxybutyl)phosphine oxide
Conditions | Yield |
---|---|
With phosphan; p-benzoquinone at 80℃; Kinetics; Condensation; oxidation; | A 15% B 85% |
Conditions | Yield |
---|---|
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% |
Reported in EPA TSCA Inventory.
OSHA PEL: TWA 0.2 ppm
ACGIH TLV: TWA 0.2 ppm
For occupational chemical analysis use NIOSH: Tributyl Phosphate, S208.
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. |