查看“︁三苯基硫化膦”︁的源代码

{{NoteTA|G1=Chemistry}}
{{chembox
|Verifiedfields=changed
|Watchedfields=changed
|verifiedrevid=470616934
|ImageFile=Triphenylphosphine-sulfide-2D-skeletal.png
|ImageSize=
|ImageFile1=Triphenylphosphine-sulfide-3D-balls.png
|ImageSize1=
|PIN=Triphenyl-λ<sup>5</sup>-phosphanethione
|IUPACName=Triphenyl-λ<sup>5</sup>-phosphanethione<br>Triphenylphosphane sulfide<br>Triphenylphosphine sulfide
|OtherNames=三苯基膦硫
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 18610
| InChI = 1/C18H15PS/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
| InChIKey = VYNGFCUGSYEOOZ-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H15PS/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VYNGFCUGSYEOOZ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 3878-45-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Q68E5JRQ8V
| PubChem =19758
| SMILES = c1ccc(cc1)P(=S)(c2ccccc2)c3ccccc3
}}
|Section2={{Chembox Properties
| Formula =C<sub>18</sub>H<sub>15</sub>PS
| MolarMass =294.350461
| Appearance = 
| Density =
| MeltingPtC = 161 - 163
| MeltingPt_notes = 
| BoilingPt =
| SolubleOther= [[二氯甲烷]], [[乙醇]]，[[異辛烷]]
  }}|Section4={{Chembox Related
| OtherCpds = [[三苯基氧化膦]]、[[三苯基膦]]、[[三苯基硒化膦]]、[[三苯基碲化膦]]
  }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = 
 }}}}
'''三苯基硫化膦'''，又名'''三苯基硫膦'''，化學式為<chem>(C6H5)3PS</chem>，或簡寫為<chem>Ph3PS </chem>（<chem>Ph</chem>為苯基）。它是一種[[有机磷化合物|有機磷化合物]]，呈無色固體，在常溫常壓下穩定<ref>{{Cite web |date=2022-01-17 21:12:51 |title=三苯基瞵硫 |website=化源網 |language=中文 |access-date=3-9-2022 |quote=常温常压下稳定}}</ref>，可溶於[[2,2,4-三甲基戊烷|異辛烷]]<ref>{{Cite web |title=三苯基瞵硫 |url=https://www.chemicalbook.com/ProductChemicalPropertiesCB1695472.htm |website=ChemicalBook |access-date=3-9-2022 |quote=isooctane: soluble |archive-date=2022-09-03 |archive-url=https://web.archive.org/web/20220903213351/https://www.chemicalbook.com/ProductChemicalPropertiesCB1695472.htm |dead-url=no }}</ref>、[[乙醇]]等[[有机溶剂|有機溶劑]]。其結構與[[三苯基氧化膦]]相似，具有''C''<sub>3</sub> 點群。<ref>{{cite journal |last1=Codding |first1=P. W. |last2=Kerr |first2=K. A. |year=1978 |title=Triphenylphosphine sulfide |journal=[[Acta Crystallographica Section B]] |volume=34 |issue=12 |pages=3785 |doi=10.1107/S0567740878012212 |doi-access=free}}</ref>

== 產生 ==
=== 無機反應 ===
<chem>P4S6</chem>可以透過<chem>P4S7</chem>與[[三苯基膦]]的反應而製備。而在<chem>P4S6</chem>的產生過程中，三苯基硫化膦是一個副產物。<ref name="Encyclo">{{cite book|title=Encyclopedia of Inorganic Chemistry, 2nd edition|chapter=Phosphorus|author1=R. Bruce King|author2=|publisher=Wiley|year=2005|isbn=9780470862100|page=3711}}</ref>

<chem>P4S7 + Ph3P -> P4S6 + Ph3PS</chem>

銥配合物<chem> [(dppe)2IrS2O2]</chem>（<chem>dppe</chem>是[[1,2-双(二苯基膦)乙烷|1,2-雙(二苯基膦)乙烷]]）與[[三苯基膦]]反應，分解成[[三苯基氧化膦]]和三苯基硫化膦。<ref name="Schmid1975">{{cite journal |last1=Schmid |first1=Günter |last2=Ritter |first2=Günter |last3=Debaerdemaeker |first3=Tony |year=1975 |title=Die Komplexchemie niederer Schwefeloxide. II. Schwefelmonoxid und Dischwefeldioxid als Komplexliganden |trans-title=The complex chemistry of lower sulfur oxides. II. Sulfur monoxide and disulfur dioxide as complex ligands |journal=Chemische Berichte |volume=108 |issue=9 |pages=3008–3013 |doi=10.1002/cber.19751080921 |issn=0009-2940}}</ref>

=== 有機反應 ===
在[[巴顿–凯洛格反应|巴頓–凱洛格反應]]中，[[酮]]與[[硫酮]]縮合產生[[烯烃|烯烴]]，<ref>[[德里克·巴顿|D. H. R. Barton]] and B. J.Willis, ''[[Chem. Commun.|J. Chem. Soc. D]]'' '''1970''', 1225.</ref><ref>Kellogg, R. M.; Wassenaar, S. ''[[Tetrahedron Lett.]]'' '''1970''', ''11'', 1987.</ref><ref>R. M. Kellogg, ''[[Tetrahedron (journal)|Tetrahedron]]'' '''1976''', ''32'', 2165.</ref>三苯基硫化膦便是副產物。過程中出現[[环硫乙烷|環硫乙烷]]環系。[[三苯基膦]]進攻環硫乙烷，所產生的烷硫負離子再對磷原子進行分子內[[親核進攻]]，產生類似於 [[Wittig反应|Wittig反應]]的四元硫磷雜環中間體。它最後發生[[消除反应|消除反應]]，得到產物[[烯烃|烯烴]]還有副產物三苯基硫化膦。詳細的[[反应机理|反應機理]]如下：
[[File:Barton-Kellogg_reaction_mechanism.svg|center|600x600px]]

== 應用 ==
=== 有機化學 ===
三苯基硫化膦可以將[[環氧化合物]]轉換成相對應的[[環硫化物]]，而三苯基硫化膦則會被轉化成[[三苯基氧化膦]]：<ref>{{cite encyclopedia|first1=Darrin L.|last1=Mayhew|first2=Derrick L. J.|last2=Clive|title=Triphenylphosphine Sulfide|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|publisher=John Wiley|date=Apr 15, 2001|location=New York, NY|doi=10.1002/047084289X.rt379}}</ref>

<chem>Ph2C2H2O + Ph3PS -> Ph2C2H2S + Ph3PO</chem>

=== 分析化學 ===
在[[分析化学|分析化學]]上，三苯基硫化膦可以被用作分析不同的[[硫化合物]]。於某些油中存在的[[硫]]（<chem>S8</chem>）、硫化[[橡膠]]中的硫、[[有機三硫化物]]等不穩定的化合物等可以跟[[三苯基膦]]發生反應，生成三苯基硫化膦。而三苯基硫化膦則可以用[[气相色谱法|氣相色譜法]]來測定。<ref>{{cite article |author=R. E. Pauls |title=Determination of Elemental Sulfur in Gasoline by Gas Chromatography with On-Column Injection and Flame Ionization Detection Following Derivatization with Triphenylphosphine |volume=48 |pages=283-288 |doi=10.1016/S0021-9673(01)97867-7 |pmid=20412650 |accessdate=17 june 2018 |language=en}}</ref><ref>{{cite journal |author1=Leroy G. Borchardt, Dwight B. Easty |title=Gas chromatographic determination of elemental and polysulfide sulfur in kraft pulping liquors |journal=Journal of Chromatography A |date=1984 |volume=299 |page=471-476 |doi=10.1016/S0021-9673(01)97867-7 |url=https://www.sciencedirect.com/science/article/pii/S0021967301978677 |accessdate=17 june 2018 |language=en}}</ref>

== 參考資料 ==
{{reflist}}

{{Organic-compound-stub}}

[[Category:苯基化合物]]
[[Category:磷-硫化合物]]