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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">5-Decen</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
<tbody><tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
</th></tr>
<tr>
<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span> <br> <br><span typeof="mw:File"></span>
</td></tr>
<tr>
<td colspan="2" style="text-align:center; font-size:80%;"><i>cis</i>-Form (oben) <i>trans</i>-Form (unten)
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>5-Decen
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<p>Dec-5-en
</p>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>10</sub>H<sub>20</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>farblose Flüssigkeit<sup id="cite_ref-Sigma_1-0" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
</th></tr>
<tr>
<td colspan="2" style="padding:0;">
<table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);">
<tbody><tr>
<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td>
<ul><li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=19689-19-1">19689-19-1</a><span class="editoronly" style="display:none;"></span></li>
<li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=7433-78-5">7433-78-5</a><span class="editoronly" style="display:none;"></span> (<i>cis</i>)</li>
<li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=7433-56-9">7433-56-9</a><span class="editoronly" style="display:none;"></span> (<i>trans</i>)</li></ul>
</td>
<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
<tr style="display:none;" class="editoronly">
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><span class="wikidata-content"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.039.282">100.039.282</a></span>
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/23916">23916</a>
</td></tr>
<tr>
<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q30118589" class="extiw external" title="d:Q30118589">Q30118589</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>140,27 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>flüssig<sup id="cite_ref-Sigma_1-1" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Dichte" title="Dichte">Dichte</a>
</td>
<td>
<p>0,74 g·cm<sup>−3</sup> (25 °C)<sup id="cite_ref-Sigma_1-2" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<ul><li>−112 °C (<i>cis</i>)<sup id="cite_ref-William_M._Haynes_2-0" class="reference"><a href="#cite_note-William_M._Haynes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li>
<li>−73 °C (<i>trans</i>)<sup id="cite_ref-William_M._Haynes_2-1" class="reference"><a href="#cite_note-William_M._Haynes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<td><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>
<ul><li>170 °C (<i>cis</i>)<sup id="cite_ref-William_M._Haynes_2-2" class="reference"><a href="#cite_note-William_M._Haynes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li>
<li>171 °C (<i>trans</i>)<sup id="cite_ref-William_M._Haynes_2-3" class="reference"><a href="#cite_note-William_M._Haynes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<ul><li>unlöslich in Wasser<sup id="cite_ref-Thermofisher_3-0" class="reference"><a href="#cite_note-Thermofisher-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li>
<li>mischbar mit Ethanol und Ether<sup id="cite_ref-William_M._Haynes_2-4" class="reference"><a href="#cite_note-William_M._Haynes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<td><a href="Brechungsindex" title="Brechungsindex">Brechungsindex</a>
</td>
<td>
<p>1,424 (20 °C)<sup id="cite_ref-Sigma_1-3" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
<tbody><tr>
<td colspan="2" style="text-align:center"><b><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-Sigma_1-4" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><span typeof="mw:File"><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien#Übersicht:_EU-Gefahrensymbole,_UN/GHS-Gefahrenpiktogramme,_UN/ADR-Gefahrensymbole" title="02 – Leicht-/Hochentzündlich"></a></span>
</td>
<td><span typeof="mw:File"><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien#Übersicht:_EU-Gefahrensymbole,_UN/GHS-Gefahrenpiktogramme,_UN/ADR-Gefahrensymbole" title="07 – Achtung"></a></span>
</td></tr></tbody></table>
<p><b>Achtung</b>
</p>
</td></tr>
<tr>
<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>
</td>
<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Flüssigkeit und Dampf entzündbar.">226</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Verursacht Hautreizungen.">315</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Verursacht schwere Augenreizung.">319</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Kann die Atemwege reizen.">335</span></span></a>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Einatmen von Staub / Rauch / Gas / Nebel / Dampf / Aerosol vermeiden.">261</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Bei Kontakt mit den Augen: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
(Geänderter Text seit Inkraftreten der „8. Anpassung an den Technischen Fortschritt“ am 1. Februar 2018)">305+351+338</span></span></a><sup id="cite_ref-Sigma_1-5" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td></tr>
</tbody></table>
</td></tr>
<tr>
<td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa). Brechungsindex: <a href="Natrium-D-Linie" title="Natrium-D-Linie">Na-D-Linie</a>, 20 °C
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>5-Decen</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Gruppe der <a href="Decene" title="Decene">Decene</a>, die in zwei <a href="Isomer" class="mw-redirect" title="Isomer">isomeren</a> Formen vorkommt.
</p>
<div class="mw-heading mw-heading2"><h2 id="Gewinnung_und_Darstellung">Gewinnung und Darstellung</h2></div>
<p><i>trans</i>-5-Decen kann durch Reaktion von <a href="5-Decin" title="5-Decin">5-Decin</a> mit <a href="Lithium" title="Lithium">Lithium</a> in <a href="Ammoniak" title="Ammoniak">Ammoniak</a> gewonnen werden.<sup id="cite_ref-John_E._McMurry_4-0" class="reference"><a href="#cite_note-John_E._McMurry-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Durch Reaktion von 5-Decin mit <a href="Wasserstoff" title="Wasserstoff">Wasserstoff</a> und einem <a href="Lindlar-Katalysator" title="Lindlar-Katalysator">Lindlar-Katalysator</a> kann <i>cis</i>-5-Decen dargestellt werden. Durch zusätzliche Reaktionsschritte (Reaktion mit <a href="Brom" title="Brom">Brom</a>, <a href="Dichlormethan" title="Dichlormethan">Dichlormethan</a> und <a href="Natriumamid" title="Natriumamid">Natriumamid</a> zu 5-Decin) ist auf diese Art und Weise eine Umwandlung der <i>cis</i>- in die <i>trans</i>-Form und umgekehrt möglich.<sup id="cite_ref-McMurry,_John_E._5-0" class="reference"><a href="#cite_note-McMurry,_John_E.-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Durch spezielle Katalysatoren ist auch Darstellung von <i>cis</i>-5-Decen mit hoher Reinheit durch <a href="Alkinmetathese" title="Alkinmetathese">Metathese</a> von <a href="1-Hexin" title="1-Hexin">1-Hexin</a> möglich.<sup id="cite_ref-mit.edu_6-0" class="reference"><a href="#cite_note-mit.edu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>5-Decen ist ein farblose Flüssigkeit, die praktisch unlöslich in Wasser ist.<sup id="cite_ref-Sigma_1-6" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-William_M._Haynes_2-5" class="reference"><a href="#cite_note-William_M._Haynes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Bei seiner <a href="Pyrolyse" title="Pyrolyse">Pyrolyse</a> entstehen neben <a href="Propen" title="Propen">Propen</a>, <a href="Ethen" title="Ethen">Ethen</a>, <a href="1-Buten" class="mw-redirect" title="1-Buten">1-Buten</a> und <a href="1-Hepten" title="1-Hepten">1-Hepten</a> zahlreiche weitere organische Verbindungen.<sup id="cite_ref-Serban_C._Moldoveanu_7-0" class="reference"><a href="#cite_note-Serban_C._Moldoveanu-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p><i>trans</i>-5-Decen kann verwendet werden, um die Wirkung der Cyclisierung und die Stabilität der bei der <a href="Ozonolyse" title="Ozonolyse">Ozonolyse</a> gebildeten Criegee-Zwischenprodukte zu charakterisieren.<sup id="cite_ref-Sigma_1-7" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Sigma-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_1-0">a</a></sup> <sup><a href="#cite_ref-Sigma_1-1">b</a></sup> <sup><a href="#cite_ref-Sigma_1-2">c</a></sup> <sup><a href="#cite_ref-Sigma_1-3">d</a></sup> <sup><a href="#cite_ref-Sigma_1-4">e</a></sup> <sup><a href="#cite_ref-Sigma_1-5">f</a></sup> <sup><a href="#cite_ref-Sigma_1-6">g</a></sup> <sup><a href="#cite_ref-Sigma_1-7">h</a></sup></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/ALDRICH/110485">trans-5-Decene, 99%</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 3. Juni 2017 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/110485?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-William_M._Haynes-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-William_M._Haynes_2-0">a</a></sup> <sup><a href="#cite_ref-William_M._Haynes_2-1">b</a></sup> <sup><a href="#cite_ref-William_M._Haynes_2-2">c</a></sup> <sup><a href="#cite_ref-William_M._Haynes_2-3">d</a></sup> <sup><a href="#cite_ref-William_M._Haynes_2-4">e</a></sup> <sup><a href="#cite_ref-William_M._Haynes_2-5">f</a></sup></span> <span class="reference-text">William M. Haynes: <cite style="font-style:italic">CRC Handbook of Chemistry and Physics, 94th Edition</cite>. CRC Press, 2016, ISBN 978-1-4665-7115-0, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>142</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=MmDOBQAAQBAJ&pg=RA3-PA142#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:5-Decen&rft.au=William+M.+Haynes&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics%2C+94th+Edition&rft.date=2016&rft.genre=book&rft.isbn=9781466571150&rft.pages=142&rft.pub=CRC+Press" style="display:none"> </span></span>
</li>
<li id="cite_note-Thermofisher-3"><span class="mw-cite-backlink"><a href="#cite_ref-Thermofisher_3-0">↑</a></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.thermofisher.com/order/catalog/product/L10689.03?SID=srch-srp-L10689.03">trans-5-Decene, 97%</a></span> bei <i><a href="Thermo_Fisher_Scientific" title="Thermo Fisher Scientific">Thermo Fisher Scientific</a></i>, abgerufen am 8. Februar 2024.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-John_E._McMurry-4"><span class="mw-cite-backlink"><a href="#cite_ref-John_E._McMurry_4-0">↑</a></span> <span class="reference-text">John E. McMurry: <cite style="font-style:italic">Organic Chemistry</cite>. Cengage Learning, 2015, ISBN 978-1-305-68646-5, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>286-IA10</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=3BKdBQAAQBAJ&pg=PA286-IA10#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:5-Decen&rft.au=John+E.+McMurry&rft.btitle=Organic+Chemistry&rft.date=2015&rft.genre=book&rft.isbn=9781305686465&rft.pages=286-IA10&rft.pub=Cengage+Learning" style="display:none"> </span></span>
</li>
<li id="cite_note-McMurry,_John_E.-5"><span class="mw-cite-backlink"><a href="#cite_ref-McMurry,_John_E._5-0">↑</a></span> <span class="reference-text">McMurry, John E.: <cite style="font-style:italic">Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 8th</cite>. Cengage Learning, 2011, ISBN 1-285-97481-6, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>209</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=4damAQAAQBAJ&pg=PA209#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:5-Decen&rft.au=McMurry%2C+John+E.&rft.btitle=Study+Guide+with+Student+Solutions+Manual+for+McMurry%27s+Organic+Chemistry%2C+8th&rft.date=2011&rft.genre=book&rft.isbn=1285974816&rft.pages=209&rft.pub=Cengage+Learning" style="display:none"> </span></span>
</li>
<li id="cite_note-mit.edu-6"><span class="mw-cite-backlink"><a href="#cite_ref-mit.edu_6-0">↑</a></span> <span class="reference-text">mit.edu: <a rel="nofollow" class="external text" href="https://dspace.mit.edu/handle/1721.1/73354">DSpace@MIT: Z-selective olefin metathesis processes and Cis/syndioselective ROMP with high oxidation state molybdenum alkylidenes</a>, abgerufen am 3. Juni 2017</span>
</li>
<li id="cite_note-Serban_C._Moldoveanu-7"><span class="mw-cite-backlink"><a href="#cite_ref-Serban_C._Moldoveanu_7-0">↑</a></span> <span class="reference-text">Serban C. Moldoveanu: <cite style="font-style:italic">Pyrolysis of Organic Molecules Applications to Health and Environmental Issues</cite>. Elsevier, 2009, ISBN 978-0-08-093215-6, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>181</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=lg2r9BDlbM8C&pg=PA181#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:5-Decen&rft.au=Serban+C.+Moldoveanu&rft.btitle=Pyrolysis+of+Organic+Molecules+Applications+to+Health+and+Environmental+Issues&rft.date=2009&rft.genre=book&rft.isbn=9780080932156&rft.pages=181&rft.pub=Elsevier" style="display:none"> </span></span>
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