Tributyl phosphate

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Tributyl phosphate
Tributyl-phosphate-2D-skeletal.png
Tributyl-phosphate-3D-vdW.png
Identifiers
CAS number 126-73-8 YesY, 6131-90-4 (trihydrate)
PubChem 31357
ChemSpider 29090 YesY
KEGG C14439 YesY
ChEBI CHEBI:35019 YesY
Jmol-3D images Image 1
Properties
Molecular formula C12H27O4P
Molar mass 266.31 g mol−1
Appearance Colorless to pale-yellow liquid[1]
Density 0.9727 g/mL
Melting point −80 °C (−112 °F; 193 K)
Boiling point 289 °C (552 °F; 562 K)
Solubility in water 1 mL/165 mL water
Hazards
MSDS External MSDS
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 146.1 °C (295.0 °F; 419.2 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Tributyl phosphate, known commonly as TBP, is an organophosphorus compound with the formula (CH3CH2CH2CH2O)3PO. This colourless, odorless liquid finds some applications as an extractant and a plasticizer. It is an ester of orthophosphoric acid with n-butanol.

Production[edit]

Tributyl phosphate is manufactured by esterification of orthophosphoric acid with n-butanol. A laboratory synthesis proceeds with phosphorus oxychloride:[2]

POCl3 + 3 C4H9OH → PO(OC4H9)3 + 3 HCl

Production is estimated at 3,000–5,000 tonnes worldwide.[3]

Use[edit]

TBP is a solvent and plasticizer for cellulose esters such as nitrocellulose and cellulose acetate. It forms stable hydrophobic complexes with some metals; these complexes are soluble in organic solvents as well as supercritical CO2. 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.[3]

TBP finds its use as a solvent in inks, synthetic resins, gums, adhesives (namely for veneer plywood) and herbicide and fungicide concentrates.

As it has no odour, it finds use as anti-foaming agent in detergent solutions, and in various emulsions, paints, and adhesives. It is also found as a defoamer in ethylene glycol-borax antifreeze solutions.[citation needed] In oil-based lubricants addition of TBP increases the oil film strength. It is used also in mercerizing liquids, where it improves their wetting properties. It is also used as a heat exchange medium.[4] TBP is used in some consumer products such as herbicides and water thinned paints and tinting bases.[5]

Nuclear chemistry[edit]

A 15–40% (usually about 30%) solution of tributyl phosphate in kerosene or dodecane is used in the liquid-liquid extraction (solvent extraction) of uranium, plutonium, and thorium from spent uranium nuclear fuel rods dissolved in nitric acid, as part of a nuclear reprocessing process known as PUREX.

The shipment of 20 tons of tributyl phosphate to North Korea from China in 2002, coinciding with the resumption of activity at Yongbyon Nuclear Scientific Research Center, was seen by the United States and the International Atomic Energy Agency as cause for concern; that amount was considered sufficient to extract enough material for perhaps three to five potential nuclear weapons.[6]

Hazards[edit]

In contact with concentrated nitric acid the TBP-kerosene solution forms hazardous and explosive red oil.

References[edit]

  1. ^ CDC - NIOSH Pocket Guide to Chemical Hazards
  2. ^ G. R. Dutton and C. R. Noller (1943), "n-Butyl phosphate", Org. Synth. ; Coll. Vol. 2: 109 
  3. ^ a b "Tributyl Phosphate | SIDS Initial Assessment Profile". Japan Chemical Industry Ecology-Toxicology & Information Center. 
  4. ^ "Tributyl Phosphate Product Information". Great Vista Chemicals. 
  5. ^ "Tributyl Phosphate". Scorecard. 
  6. ^ "Yongbyon - North Korean Special Weapons Facilities". GlobalSecurity.org.