Tributyl phosphate, known commonly as TBP, is an organophosphorus compound with the

chemical formula 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, such as pare ...

(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. Plasticizer ...

. It is an

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

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 solution, ...

with ''n''-butanol.

Production

Tributyl phosphate is manufactured by reaction of phosphoryl chloride 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 (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

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, and ...

, similarly to tricresyl phosphate. It is also used as a

flame retardant Flame retardants are a diverse group of chemicals that are added to manufactured materials, such as plastics and textiles, and surface finishes and coatings. Flame retardants are activated by the presence of an combustion, ignition source and pr ...

for cellulose fabrics such as cotton. It forms stable

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

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 backho ...

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 wo ...

, and as a solvent for extraction and purification of

rare-earth metal The rare-earth elements (REE), also called the rare-earth metals or rare earths, and sometimes the lanthanides or lanthanoids (although scandium and yttrium, which do not belong to this series, are usually included as rare earths), are a set of ...

s from their

ore Ore is natural rock or sediment that contains one or more valuable minerals, typically including metals, concentrated above background levels, and that is economically viable to mine and process. The grade of ore refers to the concentration ...

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

resin A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, predominantly terpenes. Commo ...

s, gums,

adhesive Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...

s (namely for veneer

plywood Plywood is a composite material manufactured from thin layers, or "plies", of wood veneer that have been stacked and glued together. It is an engineered wood from the family of manufactured boards, which include plywood, medium-density fibreboa ...

), and

herbicide Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...

and

fungicide Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...

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 Cleanliness, cleansing properties when in Concentration, dilute Solution (chemistry), solutions. There are a large variety of detergents. A common family is the alkylbenzene sulfonate ...

solutions, and in various

emulsion An emulsion is a mixture of two or more liquids that are normally Miscibility, 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 colloi ...

paint Paint is a material or mixture that, when applied to a solid material and allowed to dry, adds a film-like layer. As art, this is used to create an image or images known as a painting. Paint can be made in many colors and types. Most paints are ...

s, and

s. 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 odo ...

borax The BORAX Experiments were a series of safety experiments on boiling water nuclear reactors conducted by Argonne National Laboratory in the 1950s and 1960s at the National Reactor Testing Station in eastern Idaho.

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, allow ...

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, ...

s addition of TBP increases the oil film strength. It is used also in mercerizing liquids, where it improves their

wetting Wetting is the ability of a liquid to displace gas to maintain contact with a solid surface, resulting from intermolecular interactions when the two are brought together. These interactions occur in the presence of either a gaseous phase or ...

properties. It can be used as a heat-exchange medium. TBP is used in some consumer products such as

s and water-thinned paints and tinting bases.

Nuclear chemistry

Tributyl phosphate is used in combination with di(2-ethylhexyl)phosphoric acid for the

solvent extraction A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

of uranium, as part of the purification of natural ores. It is also used in

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, the ...

as part of the

PUREX PUREX (plutonium uranium reduction extraction) is a chemical method used to purify fuel for nuclear reactors or nuclear weapons. It is based on liquid–liquid extraction ion-exchange. PUREX is the '' de facto'' standard aqueous nuclear reproc ...

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

kerosene Kerosene, or paraffin, is a combustibility, combustible hydrocarbon liquid which is derived from petroleum. It is widely used as a fuel in Aviation fuel, aviation as well as households. Its name derives from the Greek (''kērós'') meaning " ...

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, also known as solvent extraction and partitioning, is a method to separate compounds or metal complexes, based on their relative solubility, solubilities in two different Miscibility, immiscible liquids, usually wate ...

(solvent extraction) of

uranium Uranium is a chemical element; it has chemical symbol, 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. Ura ...

plutonium Plutonium is a chemical element; it has symbol Pu and atomic number 94. It is a silvery-gray actinide metal that tarnishes when exposed to air, and forms a dull coating when oxidized. The element normally exhibits six allotropes and four ...

, and

thorium Thorium is a chemical element; it has symbol Th and atomic number 90. Thorium is a weakly radioactive light silver metal which tarnishes olive grey when it is exposed to air, forming thorium dioxide; it is moderately soft, malleable, and ha ...

from spent uranium

nuclear fuel Nuclear fuel refers to any substance, typically fissile material, which is used by nuclear power stations or other atomic nucleus, nuclear devices to generate energy. Oxide fuel For fission reactors, the fuel (typically based on uranium) is ...

rods dissolved in

nitric acid Nitric acid is an inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into nitrogen oxide, oxides of nitrogen. Most com ...

. Liquid extraction can also be used for chemical uranium enrichment.{{cite book , edition=1. , publisher=Taylor , title=Nuclear energy and nuclear weapon proliferation , url=https://vufind.techlib.cz/Record/000148165

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 esters Flame retardants