Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tributyl phosphate: Difference between pages

| Verifiedfields = changed

| verifiedrevid = 470613300

| ImageFile = Tributyl phosphate Structural Formula V1.svg

| ImageFileL2 = Tributyl-phosphate-3D-vdW.png

| ImageNameL2 = Spacefill model of Tributyl phosphate

| ImageFileR2 = Tributyl phosphate-3D-balls-by-AHRLS-2012.png

| ImageNameR2 = Ball and stick model of Tributyl phosphate

| PIN = Tributyl phosphate

| OtherNames =

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| CASNo2_Ref ={{fdacite|correct|FDA}}

| UNII = 95UAS8YAF5

| PubChem = 31357

| ChEBI_Ref = {{ebicite|correct|EBI}}

| Section2 = {{Chembox Properties

| C=12 | H=27 | O=4 | P=1

| MolarMass =

| Appearance = Colorless to pale-yellow liquid<ref name=PGCH/>

| Density = 0.9727 g/mL

| MeltingPtC = -80

| BoilingPtC = 289

| Solubility = 0.4 g/L<ref>{{cite journal |last1=Velavendan |first1=P |last2=Sachithanantham |first2=Ganesh |last3=Pandey |first3=N.K. |last4=Geetha |first4=R |last5=Ahmed |first5=M |last6=Mudali |first6=Kamachi |last7=Natarajan |first7=Rajamani |title=Studies on solubility of TBP in aqueous solutions of fuel reprocessing |journal=Journal of Radioanalytical and Nuclear Chemistry |date=2012 |volume=295 |issue=2 |pages=1113–1117 |doi=10.1007/s10967-012-1945-1|s2cid=95976379 }}</ref>

| VaporPressure = 0.004 mmHg (25°C)<ref name=PGCH/>

| RefractIndex = 1.4231 (at 20&nbsp;°C) <ref>{{cite journal|author1=Pabst, Florian|author2=Blochowicz, Thomas |title=On the intensity of light scattered by molecular liquids - Comparison of experiment and quantum chemical calculations|journal=[[The Journal of Chemical Physics]]|language=en|date=December 2022|volume=157|issue=24|pages=244501|doi=10.1063/5.0133511|pmid=36586992 |bibcode=2022JChPh.157x4501P |doi-access=free}}</ref>

}}

| Section3 = {{Chembox Hazards

| ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/t4706.htm External MSDS]

| NFPA-S =

| HPhrases =

| PPhrases =

| GHS_ref =

| FlashPtC = 146.1

| AutoignitionPtC =

| PEL = TWA 5 mg/m³<ref name=PGCH>{{PGCH|0625}}</ref>

| IDLH = 30 ppm<ref name=PGCH/>

| REL = TWA 0.2 ppm (2.5 mg/m³)<ref name=PGCH/>

| LC50 = 227&nbsp;ppm (cat, 4–5&nbsp;h)<br/>123&nbsp;ppm (rat, 6&nbsp;h)<br/>117&nbsp;ppm (rat)<br/>2529&nbsp;ppm (rat, 1&nbsp;h)<ref name=IDLH>{{IDLH|126738|Tributyl phosphate}}</ref>

| LD50 = 1189&nbsp;mg/kg (mouse, oral)<br/>3000&nbsp;mg/kg (rat, oral)<ref name=IDLH/>

| LCLo = 2214&nbsp;ppm (cat, 5&nbsp;h)<ref name=IDLH/>

}}

'''Tributyl phosphate''', known commonly as '''TBP''', is an [[Organophosphorus|organophosphorus compound]] with the [[chemical formula]] (CH₃CH₂CH₂CH₂O)₃PO. This colourless, odorless liquid finds some applications as an [[Liquid-liquid extraction|extractant]] and a [[plasticizer]]. It is an [[ester]] of [[phosphoric acid]] with [[n-Butanol|''n''-butanol]].

== Production ==

Tributyl phosphate is manufactured by reaction of [[phosphoryl chloride]] with [[n-Butanol|''n''-butanol]].<ref name="Dutton1943">{{OrgSynth | author = G. R. Dutton and C. R. Noller | title = n-Butyl phosphate | collvol = 2 | collvolpages = 109| year = 1943 | prep = CV2P0109}}</ref>

: POCl₃ + 3 C₄H₉OH → PO(OC₄H₉)₃ + 3 HCl

Production is estimated at 3,000–5,000 tonnes worldwide.<ref name = sids/>

== Use ==

TBP is a [[solvent]] and [[plasticizer]] for cellulose esters such as [[nitrocellulose]] and [[cellulose acetate]]. It is also used as a [[flame retardant]] for cellulose fabrics such as cotton.<ref>{{cite journal |last1=Alongi |first1=Jenny |last2=Malucelli |first2=Giulio |title=Cotton flame retardancy: state of the art and future perspectives |journal=RSC Advances |date=2015 |volume=5 |issue=31 |pages=24239–24263 |doi=10.1039/C5RA01176K|bibcode=2015RSCAd...524239A }}</ref><ref>{{cite journal |last1=Gaan |first1=Sabyasachi |last2=Sun |first2=Gang |title=Effect of phosphorus flame retardants on thermo-oxidative decomposition of cotton |journal=Polymer Degradation and Stability |date=June 2007 |volume=92 |issue=6 |pages=968–974 |doi=10.1016/j.polymdegradstab.2007.03.009}}</ref> It forms stable [[hydrophobic]] [[complex (chemistry)|complexes]] with some metals; these complexes are soluble in organic solvents as well as [[supercritical fluid extraction|supercritical CO₂]]. The major uses of TBP in industry are as a component of aircraft [[hydraulic fluid]], [[brake fluid]], and as a solvent for extraction and purification of [[rare-earth metal]]s from their [[ore]]s.<ref name=sids>{{cite web | publisher = Japan Chemical Industry Ecology-Toxicology & Information Center | title = Tributyl Phosphate &#124; SIDS Initial Assessment Profile | url = http://www.jetoc.or.jp/HP_SIDS/pdffiles/126-73-8.pdf | url-status = dead | archiveurl = https://web.archive.org/web/20071011140920/http://www.jetoc.or.jp/HP_SIDS/pdffiles/126-73-8.pdf | archivedate = 2007-10-11 }}</ref>

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

As it has no odour, it is used as an [[anti-foaming agent]] in [[detergent]] solutions, and in various [[emulsion]]s, [[paint]]s, and [[adhesive]]s. It is also found as a de-foamer in [[ethylene glycol]]-[[borax]] [[antifreeze (coolant)|antifreeze]] solutions.{{Citation needed|date=January 2008}} 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 can be used as a [[heat transfer|heat-exchange]] medium.<ref name="Ref_">{{cite web | publisher = Great Vista Chemicals | url = http://www.greatvistachemicals.com/industrial_and_specialty_chemicals/tributyl_phosphate.html | title = Tributyl Phosphate Product Information| date = 20 January 2023 }}</ref> TBP is used in some consumer products such as [[herbicide]]s and water-thinned paints and tinting bases.<ref name="Ref_a">{{cite web | title = Tributyl Phosphate | publisher = Scorecard | url = http://www.scorecard.org/chemical-profiles/consumer-products.tcl?edf_substance_id=126-73-8}}</ref>

=== Nuclear chemistry ===

Tributyl phosphate is used in combination with [[di(2-ethylhexyl)phosphoric acid]] for the [[solvent extraction]] of uranium, as part of the purification of natural ores.<ref>{{cite journal |last1=Kumar |first1=Jyothi Rajesh |last2=Kim |first2=Joon-Soo |last3=Lee |first3=Jin-Young |last4=Yoon |first4=Ho-Sung |title=A Brief Review on Solvent Extraction of Uranium from Acidic Solutions |journal=Separation & Purification Reviews |date=18 February 2011 |volume=40 |issue=2 |pages=77–125 |doi=10.1080/15422119.2010.549760|s2cid=95358600 }}</ref> It is also used in [[nuclear reprocessing]] as part of the [[PUREX]] process. 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]]. Liquid extraxction can also be used for chemical uranium enrichment.<ref name=":0">{{cite book |edition=1. |publisher=Taylor |title=Nuclear energy and nuclear weapon proliferation |url=https://vufind.techlib.cz/Record/000148165}} </ref>

== Hazards==

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

==References==

<references/>

[[Category:Organophosphates]]

[[Category:Solvents]]

[[Category:Plasticizers]]

[[Category:Radioactive waste]]

[[Category:Chelating agents]]

[[Category:Phosphate esters]]

[[Category:Butyl esters]]

[[Category:Flame retardants]]