{| align="right" width="250" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #fff; border-collapse: collapse"
|- style="border-bottom: 3px solid gray"
| align="center" colspan="2" |'''Tributyl phosphate''' <br /> [[Image:Tributylphosphate.png|Tributyl phosphate]]
|-
! bgcolor="#f0d0a0" colspan="2" | General
|-
| bgcolor="#f0e0d0" | [[Chemical formula]]
| ([[Carbon|C]][[Hydrogen|H]]<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>[[Oxygen|O]])<sub>3</sub>[[Phosphorus|P]]O
|-
| bgcolor="#f0e0d0" | [[Color|Appearance]]
| colorless to yellowish liquid
|-
| bgcolor="#f0e0d0" | [[CAS number]]
| 126-73-8 ([[anhydrous]])<br>6131-90-4 ([[hydrate|trihydrate]])
|-
! bgcolor="#f0d0a0" colspan="2" | Physical
|-
| bgcolor="#f0e0d0" | [[Molecular weight]]
| 266.32 [[atomic mass unit|amu]]
|-
| bgcolor="#f0e0d0" | [[Melting point]]
| 193[[kelvin|K]]<br>(-80°[[Celsius|C]]; -112°[[Fahrenheit|F]])
|-
| bgcolor="#f0e0d0" | [[Boiling point]]
| 562[[kelvin|K]]<br>(289°[[Celsius|C]]; 552°[[Fahrenheit|F]])
|-
| bgcolor="#f0e0d0" | [[Density]]
| 0.9727 [[gram|g]]/[[centimetre|cm]]<sup>3</sup>
|-
| bgcolor="#f0e0d0" | [[Crystal structure]]
| FIXME [[orthorhombic]]
|-
| bgcolor="#f0e0d0" | [[Solubility]]
| FIXME g/100 g of water
|-
! bgcolor="#f0d0a0" colspan="2" | Thermochemistry
|-
| bgcolor="#f0e0d0" | [[Standard enthalpy change of formation|Δ<sub>f</sub>H<sup>0</sup><sub>gas</sub>]]
| -?
|-
| bgcolor="#f0e0d0" | Δ<sub>f</sub>H<sup>0</sup><sub>liquid</sub>
| ?
|-
| bgcolor="#f0e0d0" | Δ<sub>f</sub>H<sup>0</sup><sub>solid</sub>
| ?
|-
| bgcolor="#f0e0d0" | [[Standard molar entropy|S<sup>0</sup><sub>gas, 1 bar</sub>]]
| ?
|-
| bgcolor="#f0e0d0" | S<sup>0</sup><sub>liquid, 1 bar</sub>
| ?
|-
| bgcolor="#f0e0d0" | S<sup>0</sup><sub>solid</sub>
| ?
|-
! bgcolor="#f0d0a0" colspan="2" | Safety
|-
| bgcolor="#f0e0d0" | Ingestion
| "May cause abdominal pain, vomiting. Other symptoms parallel inhalation." [1]
|-
| bgcolor="#f0e0d0" | Inhalation
| "Causes irritation to the respiratory tract. Symptoms may include coughing, shortness of breath. May cause headache. May also mildly affect blood cholinesterase levels, which will affect central nervous system operation." [1]
|-
| bgcolor="#f0e0d0" | Skin
| "Causes irritation to skin. Symptoms include redness, itching, and pain. May be absorbed through the skin with possible systemic effects." [1]
|-
| bgcolor="#f0e0d0" | Eyes
| "Causes irritation, redness, and pain." [1]
|-
! bgcolor="#f0d0a0" colspan="2" | Firefighting Data
|-
| bgcolor="#f0e0d0" | Flash point
| 120[[Celsius|C]] (248°[[Fahrenheit|F]])
|-
| bgcolor="#f0e0d0" | Extingushing Media
| "Water spray, dry chemical, alcohol foam, or carbon dioxide.  Water or foam may cause frothing."[1]
|-
| bgcolor="#f0d0a0" colspan="2" align="center" |
<small>
'''[[SI]] units and [[standard temperature and pressure|standard conditions]] used unless otherwise stated'''.<br/>
[[Wikipedia:Chemical infoboxes|Disclaimer and references]]
</small>
|-
|}

'''Tributyl phosphate''' ('''TBP'''), '''''n''-tributyl phosphate''', or '''tri-''n''-butyl phosphate''', is an odorless liquid, colorless to pale yellow in appearance, with applications in industrial and nuclear chemistry. It is slightly flammable and moderately dangerous to humans. It is an [[ester]] of [[orthophosphoric acid]] and ''n''-[[butanol]]. It is a very good [[solvent]].

== History ==

Section pending.

== Production ==

Tributyl phosphate is manufactured by [[esterification]] of [[orthophosphoric acid]] with [[butyl alcohol]].

== Use ==
=== Industrial ===

TBP is a [[solvent]] and [[plasticizer]] for [[cellulose ester]]s (eg. [[nitrocellulose]] and [[cellulose acetate]]). It forms stable hydrophobic complexes with some metals; these complex are soluble in organic solvents and in [[supercritical fluid extraction|supercritical CO<sub>2</sub>]].
It is used for [[solvent extraction]] of [[rare earth metal]]s from their [[ore]]s, and of components of spent nuclear fuel (see [[#Nuclear Chemistry|Nuclear Chemistry section]]).

TBP finds its use as a solvent in [[ink]]s, synthetic [[resin]]s, [[gum]]s, [[adhesive]]s (namely for [[veneer (wood)|veneer]] [[plywood]]) and [[herbicide]] and [[fungicide]] concentrates.

As it has no odour, together with a small amount of eg. [[isopropyl alcohol]] it finds use as [[anti-foaming agent]] in most [[detergent]] solutions, and in various [[emulsion]]s, paints, and adhesives. It is also found as a defoamer in [[ethylene glycol]]-[[borax]] [[antifreeze (coolant)|antifreze]] solutions.

In oil-based [[lubricant]]s 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.

[http://www.greatvistachemicals.com/industrial_and_specialty_chemicals/tributyl_phosphate.html]

=== Nuclear Chemistry ===

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]].

Because of this, the shipment of 20 tons of tributyl phosphate to [[North Korea]] from [[China]] in 2002, coinciding with the resumption of activity at the [[Yongbyon]] nuclear facilities, 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 weapon|nuclear weapons]].

== Hazards ==

The material will burn, but (in the absence of significant vaporization) should not pose a particular explosive hazard.  Inhalation and ingestion should be avoided due to possible [[central nervous system]] effects.  A lab coat and safety glasses should be worn; an
tributyl phosphate is not presently known to be, or suspected of being, a carcinogen, but may be mutagenic or have reproductive effects; consult the substance's [[MSDS]] for full details (see link at bottom).

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

== Sources ==
[http://www.jtbaker.com/msds/englishhtml/t4706.htm Material Safety Data Sheet (MSDS) for tributyl phosphate]

== See also ==
* [[Red oil]]

[[Category:Organophosphates]]
[[Category:Solvents]]
[[Category:Esters]]
[[Category:Plasticizers]]
[[Category:Radioactive waste]]