Tributyl phosphate, known commonly as TBP, is an

organophosphorus compound Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...

with the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

(CH₃CH₂CH₂CH₂O)₃PO. This colourless, odorless liquid finds some applications as an extractant and a

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticiz ...

. It is an

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

phosphoric acid Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solutio ...

with ''n''-butanol.

Production

Tributyl phosphate is manufactured by reaction of

phosphoryl chloride Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula . It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosp ...

with ''n''-butanol. : POCl₃ + 3 C₄H₉OH → PO(OC₄H₉)₃ + 3 HCl Production is estimated at 3,000–5,000 tonnes worldwide.

Use

TBP is a

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

and

for cellulose esters such as

nitrocellulose Nitrocellulose (also known as cellulose nitrate, flash paper, flash cotton, guncotton, pyroxylin and flash string, depending on form) is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid and ...

and

cellulose acetate In biochemistry, cellulose acetate refers to any acetate ester of cellulose, usually cellulose diacetate. It was first prepared in 1865. A bioplastic, cellulose acetate is used as a film base in photography, as a component in some coatings, ...

. It forms stable

hydrophobic In chemistry, hydrophobicity is the physical property of a molecule that is seemingly repelled from a mass of water (known as a hydrophobe). In contrast, hydrophiles are attracted to water. Hydrophobic molecules tend to be nonpolar and, ...

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 A hydraulic fluid or hydraulic liquid is the medium by which power is transferred in hydraulic machinery. Common hydraulic fluids are based on mineral oil or water. Examples of equipment that might use hydraulic fluids are excavators and backhoe ...

brake fluid Brake fluid is a type of hydraulic fluid used in hydraulic brake and hydraulic clutch applications in automobiles, motorcycles, light trucks, and some bicycles. It is used to transfer force into pressure, and to amplify braking force. It works b ...

, and as a solvent for extraction and purification of rare-earth metals from their

ore Ore is natural rock or sediment that contains one or more valuable minerals, typically containing metals, that can be mined, treated and sold at a profit.Encyclopædia Britannica. "Ore". Encyclopædia Britannica Online. Retrieved 7 April ...

s. TBP finds its use as a solvent in inks, synthetic

resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on n ...

gum Gum may refer to: Types of gum * Adhesive * Bubble gum * Chewing gum * Gum (botany), sap or other resinous material associated with certain species of the plant kingdom ** Gum arabic, made from the sap of ''Acacia senegal'', an Old World tree s ...

s, adhesives (namely for

veneer Veneer may refer to: Materials * Veneer (dentistry), a cosmetic treatment for teeth * Masonry veneer, a thin facing layer of brick * Stone veneer, a thin facing layer of stone * Wood veneer, a thin facing layer of wood Arts and entertainment ...

plywood), and herbicide and fungicide concentrates. As it has no odour, it is used as an anti-foaming agent in

detergent A detergent is a surfactant or a mixture of surfactants with cleansing properties when in dilute solutions. There are a large variety of detergents, a common family being the alkylbenzene sulfonates, which are soap-like compounds that are m ...

solutions, and in various

emulsion An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Althou ...

paint Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...

s, and adhesives. It is also found as a de-foamer in

ethylene glycol Ethylene glycol ( IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an od ...

borax Borax is a salt (chemistry), salt (ionic compound), a hydration (chemistry), hydrated borate of sodium, with chemical formula often written . It is a colorless crystalline solid, that dissolves in water to make a base (chemistry), basic aqueo ...

antifreeze An antifreeze is an additive which lowers the freezing point of a water-based liquid. An antifreeze mixture is used to achieve freezing-point depression for cold environments. Common antifreezes also increase the boiling point of the liquid, al ...

solutions. In oil-based

lubricant A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, t ...

s addition of TBP increases the oil film strength. It is used also in

mercerizing Mercerisation is a textile finishing treatment for cellulose fabric and yarn, mainly cotton and flax, which improves dye uptake and tear strength, reduces fabric shrinkage, and imparts a silk-like luster. Development The process was devis ...

liquids, where it improves their

wetting Wetting is the ability of a liquid to maintain contact with a solid surface, resulting from intermolecular interactions when the two are brought together. This happens in presence of a gaseous phase or another liquid phase not miscible with ...

properties. It can be used as a

heat-exchange A heat exchanger is a system used to transfer heat between a source and a working fluid. Heat exchangers are used in both cooling and heating processes. The fluids may be separated by a solid wall to prevent mixing or they may be in direct contac ...

medium. TBP is used in some consumer products such as herbicides and water-thinned paints and tinting bases.

Nuclear chemistry

A 15–40% (usually about 30%) solution of tributyl phosphate in

kerosene Kerosene, paraffin, or lamp oil is a combustible hydrocarbon liquid which is derived from petroleum. It is widely used as a fuel in aviation as well as households. Its name derives from el, κηρός (''keros'') meaning " wax", and was reg ...

dodecane Dodecane (also known as dihexyl, bihexyl, adakane 12, or duodecane) is an oily liquid ''n''-alkane hydrocarbon with the chemical formula C12H26 (which has 355 isomers). It is used as a solvent, distillation chaser, and scintillator component. It ...

is used in the

liquid–liquid extraction Liquid–liquid extraction (LLE), also known as solvent extraction and partitioning, is a method to separate compounds or metal complexes, based on their relative solubilities in two different immiscible liquids, usually water (polar) and an orga ...

(solvent extraction) of

uranium Uranium is a chemical element with the symbol U and atomic number 92. It is a silvery-grey metal in the actinide series of the periodic table. A uranium atom has 92 protons and 92 electrons, of which 6 are valence electrons. Uranium is weakly ...

plutonium Plutonium is a radioactive chemical element with the symbol Pu and atomic number 94. It is an actinide metal of silvery-gray appearance that tarnishes when exposed to air, and forms a dull coating when oxidized. The element normally exhib ...

, and

thorium Thorium is a weakly radioactive metallic chemical element with the symbol Th and atomic number 90. Thorium is silvery and tarnishes black when it is exposed to air, forming thorium dioxide; it is moderately soft and malleable and has a high ...

from spent uranium

nuclear fuel Nuclear fuel is material used in nuclear power stations to produce heat to power turbines. Heat is created when nuclear fuel undergoes nuclear fission. Most nuclear fuels contain heavy fissile actinide elements that are capable of undergoi ...

rods dissolved in

nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available ni ...

, as part of a

nuclear reprocessing Nuclear reprocessing is the chemical separation of fission products and actinides from spent nuclear fuel. Originally, reprocessing was used solely to extract plutonium for producing nuclear weapons. With commercialization of nuclear power, ...

process known as

PUREX PUREX (plutonium uranium reduction extraction) is a chemistry, chemical method used to purify fuel for nuclear reactors or nuclear weapons. PUREX is the ''de facto'' standard aqueous nuclear reprocessing method for the recovery of uranium and p ...

. The shipment of 20 tons of tributyl phosphate to

North Korea North Korea, officially the Democratic People's Republic of Korea (DPRK), is a country in East Asia. It constitutes the northern half of the Korean Peninsula and shares borders with China and Russia to the north, at the Yalu (Amnok) and ...

from China in 2002, coinciding with the resumption of activity at

Yongbyon Nuclear Scientific Research Center The Nyongbyon Nuclear Scientific Research Center is North Korea's major nuclear facility, operating its first nuclear reactors. It is located in Nyongbyon County in North Pyongan Province, about 100 km north of Pyongyang. The center produ ...

, was seen by the United States and the

International Atomic Energy Agency The International Atomic Energy Agency (IAEA) is an intergovernmental organization that seeks to promote the peaceful use of nuclear energy and to inhibit its use for any military purpose, including nuclear weapons. It was established in 1 ...

as cause for concern; that amount was considered sufficient to extract enough material for perhaps three to five potential

nuclear weapon A nuclear weapon is an explosive device that derives its destructive force from nuclear reactions, either fission (fission bomb) or a combination of fission and fusion reactions ( thermonuclear bomb), producing a nuclear explosion. Both bom ...

s.{{cite web , title = Yongbyon - North Korean Special Weapons Facilities , url = http://www.globalsecurity.org/wmd/world/dprk/yongbyon.htm , publisher = GlobalSecurity.org

Hazards

In contact with concentrated

the TBP-kerosene solution forms hazardous and explosive red oil.

References

Organophosphates Solvents Plasticizers Radioactive waste Chelating agents Phosphate esters Butyl compounds