| Revision as of 14:18, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 445155378 of page Trioctylphosphine_oxide for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 20:06, 22 July 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,204 edits Phosphine oxides link |
| Line 1: |
Line 1: |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{Chembox |
|
{{Chembox |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 413980168 |
|
| verifiedrevid = 470616197 |
|
| ImageFile = Trioctylphosphine oxide.png |
|
| ImageFile = Trioctylphosphine oxide.png |
|
| ImageFile_Ref = {{Chemboximage|correct|??}} |
|
| ImageFile_Ref = {{Chemboximage|correct|??}} |
|
| ImageSize = 244 |
|
| ImageSize = 244 |
|
| ImageName = Structural formula of trioctylphosphine oxide |
|
| ImageName = Structural formula of trioctylphosphine oxide |
|
| IUPACName = Trioctyl-λ<sup>5</sup>-phosphanone |
|
| PIN = Trioctyl-λ<sup>5</sup>-phosphanone |
|
| OtherNames = Tri-''n''-octylphosphine oxide |
|
| OtherNames = Tri-''n''-octylphosphine oxide |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| Abbreviations = TOPO |
|
| Abbreviations = TOPO |
|
| CASNo = 78-50-2 |
|
| CASNo = 78-50-2 |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| PubChem = 65577 |
|
|
|
| UNII = EXU8U2AM5A |
|
| PubChem_Ref = {{Pubchemcite|correct|PubChem}} |
|
|
| ChemSpiderID = 59020 |
|
| PubChem = 65577 |
|
|
| ChemSpiderID = 59020 |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| EINECS = 201-121-3 |
|
|
| UNNumber = 3077 |
|
| EINECS = 201-121-3 |
|
| MeSHName = Trioctyl+phosphine+oxide |
|
| UNNumber = 3077 |
|
|
| MeSHName = Trioctyl+phosphine+oxide |
|
| RTECS = SZ1662500 |
|
| RTECS = SZ1662500 |
|
| Beilstein = 1796648 |
|
| Beilstein = 1796648 |
|
| SMILES = CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC |
|
| SMILES = CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC |
|
| StdInChI = 1S/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3 |
|
| StdInChI = 1S/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3 |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| InChI = 1/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3 |
|
| InChI = 1/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3 |
|
| StdInChIKey = ZMBHCYHQLYEYDV-UHFFFAOYSA-N |
|
| StdInChIKey = ZMBHCYHQLYEYDV-UHFFFAOYSA-N |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| InChIKey = ZMBHCYHQLYEYDV-UHFFFAOYAY |
|
| InChIKey = ZMBHCYHQLYEYDV-UHFFFAOYAY |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C = 24 |
|
| C=24 | H=51 | O=1 | P=1 |
|
⚫ |
| Appearance = White, opaque crystals |
|
| H = 51 |
|
|
| O = 1 |
|
| MeltingPtC = 50 to 54 |
|
| P = 1 |
|
| BoilingPtC = 411.2 |
|
|
| BoilingPt_notes = at 760 mmHg<ref>{{cite journal | author = Nakhutin, I. E. | journal = Zhurnal Obshchei Khimii | year = 1971 | volume = 41 | issue = 5 | pages = 940–943}}</ref> |
|
| ExactMass = 386.367752766 g mol<sup>-1</sup> |
|
| ⚫ |
| Appearance = White, opaque crystals |
|
|
| MeltingPtCL = 50 |
|
|
| MeltingPtCH = 54 |
|
|
| BoilingPtC = 238 |
|
|
| Boiling_notes = at 3 mmHg |
|
|
}} |
|
}} |
|
| Section3 = {{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
|
| Hazards_ref=<ref>{{cite web |title=C&L Inventory |url=https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/59317 |website=echa.europa.eu}}</ref> |
|
| EUClass = {{Hazchem Xi}} |
|
|
| RPhrases = {{R38}}, {{R41}} |
|
| GHSPictograms = {{GHS05}} |
|
|
| GHSSignalWord = Danger |
|
| SPhrases = {{S26}}, {{S39}} |
|
|
|
| HPhrases = {{H-phrases|315|318}} |
| ⚫ |
| NFPA-H = 3 |
|
|
|
| PPhrases = {{P-phrases|264|280|302+352|305+351+338|310|332+313|362}} |
|
| NFPA-F = 1 |
|
|
| NFPA-R = 0 |
|
| NFPA-H = 3 |
|
| FlashPt = 110 °C |
|
| NFPA-F = 1 |
|
⚫ |
| NFPA-R = 0 |
|
|
| FlashPtC = 110 |
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Trioctylphosphine oxide''' ('''TOPO''') is an ] with the ] OP(C<sub>8</sub>H<sub>17</sub>)<sub>3</sub>. Frequently referred to as TOPO, this compound is used as an extraction or stabilizing agent. It is an air-stable white solid at room temperature. It is lipophilic, and like other ] serves as a ] owing to a partial negative charge at the O atom. |
|
|
|
|
|
==Preparation and use== |
|
|
TOPO is usually prepared by oxidation of trioctylphosphine, which in turn is produced by alkylation of ]. |
|
|
|
|
|
The main use of TOPO is in solvent extraction of metals, especially uranium.<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> The high ]ity and high polarity are properties key to this application. Its high ], which results from the dipolar phosphorus-oxygen bond, allows this compound to bind to metal ions. The octyl groups confer solubility in low polarity solvents such as ].<ref>Watson, E. K.; Rickelton, W. A. "A review of the industrial and recent potential applications of trioctylphosphine oxide" |
|
|
Solvent Extraction and Ion Exchange 1992, volume 10, pp. 879-89. {{doi|10.1080/07366299208918141}}</ref> |
|
|
|
|
|
In the research laboratory, both trioctylphosphine and TOPO are frequently useful as a capping ] for the production of ] such as those consisting of ]. In these cases, TOPO serves as solvent for the synthesis and solubilizes the growing ]. TOPO-coated quantum dots are typically soluble in ], ], and (to a lesser extent) ].<ref>{{cite journal |doi=10.1021/cm3035642|title=Conversion Reactions of Cadmium Chalcogenide Nanocrystal Precursors |year=2013 |last1=García-Rodríguez |first1=Raúl |last2=Hendricks |first2=Mark P. |last3=Cossairt |first3=Brandi M. |last4=Liu |first4=Haitao |last5=Owen |first5=Jonathan S. |journal=Chemistry of Materials |volume=25 |issue=8 |pages=1233–1249 }}</ref><!-- tangential These quantum dots are also used in ] as part of the protective barrier to prevent degradation as it travels through the harsh climate of the body.--> |
|
|
|
|
|
==References== |
|
|
{{Reflist}} |
|
|
|
|
|
] |