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{{Chembox
{{Chembox
| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 470613300
| verifiedrevid = 470613300
| ImageFile = Tributyl-phosphate-2D-skeletal.png
| ImageFile = Tributyl phosphate Structural Formula V1.svg
| ImageFileL2 = Tributyl-phosphate-3D-vdW.png
| ImageFileL2 = Tributyl-phosphate-3D-vdW.png
| ImageNameL2 = Spacefill model of Tributyl phosphate
| ImageNameL2 = Spacefill model of Tributyl phosphate
| ImageFileR2 = Tributyl phosphate-3D-balls-by-AHRLS-2012.png
| ImageFileR2 = Tributyl phosphate-3D-balls-by-AHRLS-2012.png
| ImageNameR2 = Ball and stick model of Tributyl phosphate
| ImageNameR2 = Ball and stick model of Tributyl phosphate
| PIN = Tributyl phosphate
| PIN = Tributyl phosphate
| OtherNames =
| OtherNames =
|Section1={{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 29090
| ChemSpiderID = 29090
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| SMILES = O=P(OCCCC)(OCCCC)OCCCC
| SMILES = O=P(OCCCC)(OCCCC)OCCCC
}}
}}
|Section2={{Chembox Properties
| Section2 = {{Chembox Properties
| C=12 | H=27 | O=4 | P=1
| C=12 | H=27 | O=4 | P=1
| MolarMass =
| MolarMass =
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| 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>
| 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/>
| 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
| Section3 = {{Chembox Hazards
| ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/t4706.htm External MSDS]
| ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/t4706.htm External MSDS]
| NFPA-H = 2
| NFPA-H = 2
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== Use ==
== Use ==
TBP is a [[solvent]] and [[plasticizer]] for cellulose esters such as [[nitrocellulose]] and [[cellulose acetate]]. It forms stable [[hydrophobic]] [[complex (chemistry)|complexes]] with some metals; these complexes are soluble in organic solvents as well as [[supercritical fluid extraction|supercritical CO<sub>2</sub>]]. 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 is a [[solvent]] and [[plasticizer]] for cellulose esters such as [[nitrocellulose]] and [[cellulose acetate]], similarly to [[tricresyl phosphate]]. 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 CO<sub>2</sub>]]. 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.
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}}</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>
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 ===
=== 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]].
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 extraction 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>

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 weapon]]s.<ref name="Ref_b">{{cite web | title = Yongbyon - North Korean Special Weapons Facilities | url = http://www.globalsecurity.org/wmd/world/dprk/yongbyon.htm | publisher = GlobalSecurity.org}}</ref>


== Hazards==
== Hazards==
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[[Category:Chelating agents]]
[[Category:Chelating agents]]
[[Category:Phosphate esters]]
[[Category:Phosphate esters]]
[[Category:Butyl esters]]
[[Category:Flame retardants]]

Latest revision as of 21:14, 17 December 2024

Tributyl phosphate
Spacefill model of Tributyl phosphate
Spacefill model of Tributyl phosphate
Ball and stick model of Tributyl phosphate
Ball and stick model of Tributyl phosphate
Names
Preferred IUPAC name
Tributyl phosphate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.365 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H3 checkY
    Key: STCOOQWBFONSKY-UHFFFAOYSA-N checkY
  • InChI=1/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H3
    Key: STCOOQWBFONSKY-UHFFFAOYAN
  • O=P(OCCCC)(OCCCC)OCCCC
Properties
C12H27O4P
Molar mass 266.318 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)
0.4 g/L[2]
Vapor pressure 0.004 mmHg (25°C)[1]
1.4231 (at 20 °C) [3]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
1
1
Flash point 146.1 °C (295.0 °F; 419.2 K)
Lethal dose or concentration (LD, LC):
1189 mg/kg (mouse, oral)
3000 mg/kg (rat, oral)[4]
227 ppm (cat, 4–5 h)
123 ppm (rat, 6 h)
117 ppm (rat)
2529 ppm (rat, 1 h)[4]
2214 ppm (cat, 5 h)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 5 mg/m3[1]
REL (Recommended)
 TWA 0.2 ppm (2.5 mg/m3)[1]
IDLH (Immediate danger)
 30 ppm[1]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

Production

[edit]

Tributyl phosphate is manufactured by reaction of phosphoryl chloride with n-butanol.[5]

POCl3 + 3 C4H9OH → PO(OC4H9)3 + 3 HCl

Production is estimated at 3,000–5,000 tonnes worldwide.[6]

Use

[edit]

TBP is a solvent and plasticizer for cellulose esters such as nitrocellulose and cellulose acetate, similarly to tricresyl phosphate. It is also used as a flame retardant for cellulose fabrics such as cotton.[7][8] 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, brake fluid, and as a solvent for extraction and purification of rare-earth metals from their ores.[6]

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 is used as an anti-foaming agent in detergent solutions, and in various emulsions, paints, and adhesives. It is also found as a de-foamer 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 can be used as a heat-exchange medium.[9] TBP is used in some consumer products such as herbicides and water-thinned paints and tinting bases.[10]

Nuclear chemistry

[edit]

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.[11] 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 extraction can also be used for chemical uranium enrichment.[12]

Hazards

[edit]

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

References

[edit]
  1. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0625". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Velavendan, P; Sachithanantham, Ganesh; Pandey, N.K.; Geetha, R; Ahmed, M; Mudali, Kamachi; Natarajan, Rajamani (2012). "Studies on solubility of TBP in aqueous solutions of fuel reprocessing". Journal of Radioanalytical and Nuclear Chemistry. 295 (2): 1113–1117. doi:10.1007/s10967-012-1945-1. S2CID 95976379.
  3. ^ Pabst, Florian; Blochowicz, Thomas (December 2022). "On the intensity of light scattered by molecular liquids - Comparison of experiment and quantum chemical calculations". The Journal of Chemical Physics. 157 (24): 244501. Bibcode:2022JChPh.157x4501P. doi:10.1063/5.0133511. PMID 36586992.
  4. ^ a b c "Tributyl phosphate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ G. R. Dutton and C. R. Noller (1943). "n-Butyl phosphate". Organic Syntheses; Collected Volumes, vol. 2, p. 109.
  6. ^ a b "Tributyl Phosphate | SIDS Initial Assessment Profile" (PDF). Japan Chemical Industry Ecology-Toxicology & Information Center. Archived from the original (PDF) on 2007-10-11.
  7. ^ Alongi, Jenny; Malucelli, Giulio (2015). "Cotton flame retardancy: state of the art and future perspectives". RSC Advances. 5 (31): 24239–24263. Bibcode:2015RSCAd...524239A. doi:10.1039/C5RA01176K.
  8. ^ Gaan, Sabyasachi; Sun, Gang (June 2007). "Effect of phosphorus flame retardants on thermo-oxidative decomposition of cotton". Polymer Degradation and Stability. 92 (6): 968–974. doi:10.1016/j.polymdegradstab.2007.03.009.
  9. ^ "Tributyl Phosphate Product Information". Great Vista Chemicals. 20 January 2023.
  10. ^ "Tributyl Phosphate". Scorecard.
  11. ^ Kumar, Jyothi Rajesh; Kim, Joon-Soo; Lee, Jin-Young; Yoon, Ho-Sung (18 February 2011). "A Brief Review on Solvent Extraction of Uranium from Acidic Solutions". Separation & Purification Reviews. 40 (2): 77–125. doi:10.1080/15422119.2010.549760. S2CID 95358600.
  12. ^ Nuclear energy and nuclear weapon proliferation (1. ed.). Taylor.
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