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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Dodecane</span></h1>
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<p>Die <b>Dodecane</b> bilden eine <a href="Stoffgruppe" title="Stoffgruppe">Stoffgruppe</a> aus der Gruppe der <a href="Alkane" title="Alkane">Alkane</a>. Namensgeber ist der lineare Vertreter <a href="Dodecan" title="Dodecan">Dodecan</a>. Die Dodecane umfassen theoretisch 355 <a href="Isomerie#Konstitutionsisomerie_oder_Strukturisomerie" title="Isomerie">konstitutionsisomere</a> bzw. 900 konstitutions- und <a href="Isomerie#Konfigurationsisomerie" title="Isomerie">konfigurationsisomere</a> Verbindungen mit der <a href="Summenformel" title="Summenformel">Summenformel</a> C<sub>12</sub>H<sub>26</sub>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In öffentlich verfügbaren Datenbanken werden (Stand März 2024) zwischen 68 und 390 tatsächlich bekannte Isomere geführt, darunter auch Stereoisomere.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>In der Natur kommen Dodecan-Isomere beispielsweise bei der <a href="Amerikanische_Dickkopfelritze" class="mw-redirect" title="Amerikanische Dickkopfelritze">Amerikanischen Dickkopfelritze</a> als Stoffwechselprodukte vor, bei denen <i>n</i>-Dodecan und 2,2,4,6,6-Pentamethylheptan<sup id="cite_ref-:0_6-0" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>S 1<span class="cite-bracket">]</span></a></sup> <a href="Biotransformation" title="Biotransformation">biotransformiert</a> werden, um somit die <a href="Bioakkumulation" title="Bioakkumulation">Bioakkumulation</a> zu verhindern.<sup id="cite_ref-PMID12137037_7-0" class="reference"><a href="#cite_note-PMID12137037-7"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In der technischen Chemie wird eine Mischung aus Dodecan-Isomeren als <a href="Suspension_(Chemie)" title="Suspension (Chemie)">Suspensionsmittel</a> verwendet, vor allem für die katalytische <a href="Kettenpolymerisation" title="Kettenpolymerisation">Kettenpolymerisation</a> von <a href="Olefine" title="Olefine">Olefinen</a> (Polyolefine) mithilfe von Titaniumhalogenid-Materialien.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Konstitutionsisomere">Konstitutionsisomere</h2></div>
<p>Aufbauend auf einer Stammkette von fünf bis elf Kohlenstoffatomen müssen sieben bis ein Kohlenstoffatom in Seitenketten ergänzt werden. Diese <a href="Substituent" title="Substituent">Substituenten</a> können <a href="Methylgruppe" title="Methylgruppe">Methyl</a>-, <a href="Ethylgruppe" title="Ethylgruppe">Ethyl</a>-, <a href="Propylgruppe" title="Propylgruppe">Propyl</a>-, <a href="Propylgruppe" title="Propylgruppe">Isopropyl</a>- oder <a href="Butylgruppe" title="Butylgruppe">tert-Butylgruppen</a> sein. Einige Beispiele bekannter Verbindungen sind:
</p>
<ul><li>2,2,4,6,6-Pentamethylheptan<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_6-1" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>S 1<span class="cite-bracket">]</span></a></sup></li>
<li>4-Ethyldecan<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>S 2<span class="cite-bracket">]</span></a></sup></li>
<li>3,6-Diethyloctan<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>S 3<span class="cite-bracket">]</span></a></sup></li></ul>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a></span> <span class="reference-text">D. Bonchev: <cite style="font-style:italic">Chemical Graph Theory: Introduction and Fundamentals</cite>. CRC Press, 1991, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>300</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=X0AG7HhiccoC&pg=PA186&q=dodecane+355#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:Dodecane&rft.au=D.+Bonchev&rft.btitle=Chemical+Graph+Theory%3A+Introduction+and+Fundamentals&rft.date=1991&rft.genre=book&rft.pages=300&rft.pub=CRC+Press" style="display:none"> </span></span>
</li>
<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">Sascha Kurz: <cite style="font-style:italic">Anzahl von Strukturisomeren der Alkane</cite>. Universität Bayreuth, 11. Mai 2005 (<a rel="nofollow" class="external text" href="http://www.mathe2.uni-bayreuth.de/sascha/papers/alkane.pdf">uni-bayreuth.de</a> [PDF]).<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:Dodecane&rft.au=Sascha+Kurz&rft.btitle=Anzahl+von+Strukturisomeren+der+Alkane&rft.date=2005-05-11&rft.genre=book&rft.pub=Universit%C3%A4t+Bayreuth" style="display:none"> </span></span>
</li>
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><span class="cite"><a rel="nofollow" class="external text" href="https://oeis.org/A000628/list"><i>Number of n-node unrooted steric quartic trees; number of n-carbon alkanes C(n)H(2n+2) taking stereoisomers into account.</i></a> In: <i><a href="On-Line_Encyclopedia_of_Integer_Sequences" title="On-Line Encyclopedia of Integer Sequences">On-Line Encyclopedia of Integer Sequences</a>.</i><span class="Abrufdatum"> Abgerufen am 21. März 2024</span>.</span><span style="display: none;" class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rfr_id=info%3Asid%2Fde.wikipedia.org%3ADodecane&rft.title=Number+of+n-node+unrooted+steric+quartic+trees%3B+number+of+n-carbon+alkanes+C%28n%29H%282n%2B2%29+taking+stereoisomers+into+account.&rft.description=Number+of+n-node+unrooted+steric+quartic+trees%3B+number+of+n-carbon+alkanes+C%28n%29H%282n%2B2%29+taking+stereoisomers+into+account.&rft.identifier=https%3A%2F%2Foeis.org%2FA000628%2Flist"> </span></span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text"><span class="cite"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Search.aspx?q=c12h26"><i>Chemical Identifier Search | c12h26.</i></a><span class="Abrufdatum"> Abgerufen am 14. März 2024</span>.</span><span style="display: none;" class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rfr_id=info%3Asid%2Fde.wikipedia.org%3ADodecane&rft.title=Chemical+Identifier+Search+%7C+c12h26&rft.description=Chemical+Identifier+Search+%7C+c12h26&rft.identifier=https%3A%2F%2Fwww.chemspider.com%2FSearch.aspx%3Fq%3Dc12h26"> </span></span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text"><span class="cite">NIST Office of Data and Informatics: <a rel="nofollow" class="external text" href="https://webbook.nist.gov/cgi/cbook.cgi?Name=c12h26&Units=SI"><i>Search Results.</i></a><span class="Abrufdatum"> Abgerufen am 14. März 2024</span> (englisch).</span><span style="display: none;" class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rfr_id=info%3Asid%2Fde.wikipedia.org%3ADodecane&rft.title=Search+Results&rft.description=Search+Results&rft.identifier=https%3A%2F%2Fwebbook.nist.gov%2Fcgi%2Fcbook.cgi%3FName%3Dc12h26%26Units%3DSI&rft.creator=NIST+Office+of+Data+and+Informatics&rft.language=en"> </span></span>
</li>
<li id="cite_note-PMID12137037-7"><span class="mw-cite-backlink"><a href="#cite_ref-PMID12137037_7-0">↑</a></span> <span class="reference-text">J. Tolls, J. van Dijk: <i>Bioconcentration of n-dodecane and its highly branched isomer 2,2,4,6,6-pentamethylheptane in fathead minnows.</i> In: <i>Chemosphere.</i> Band 47, Nummer 10, Juni 2002, S. 1049–1057, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/12137037?dopt=Abstract">PMID 12137037</a>.</span>
</li>
<li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">
<span class="cite">Patent <a rel="nofollow" class="external text" href="https://worldwide.espacenet.com/publicationDetails/biblio?locale=de_EP&CC=EP&NR=0026655">EP0026655</a>: <i>Titanium halide material and production thereof.</i> Veröffentlicht am <span style="white-space:nowrap;">8. April 1981</span>, Erfinder: Ian William Parsons, John Andrew Licchelli, Anthony David Caunt.</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft_id=EP0026655&rft.applcc=EP&rft.title=Titanium+halide+material+and+production+thereof&rft.inventor=Ian+William+Parsons%2C+John+Andrew+Licchelli%2C+Anthony+David+Caunt&rft.pubdate=1981-04-08"></span></span>
</li>
<li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text"><span class="cite"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.24272.html"><i>2,2,4,6,6-PENTAMETHYLHEPTANE | C12H26 | ChemSpider.</i></a><span class="Abrufdatum"> Abgerufen am 17. März 2024</span>.</span><span style="display: none;" class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rfr_id=info%3Asid%2Fde.wikipedia.org%3ADodecane&rft.title=2%2C2%2C4%2C6%2C6-PENTAMETHYLHEPTANE+%7C+C12H26+%7C+ChemSpider&rft.description=2%2C2%2C4%2C6%2C6-PENTAMETHYLHEPTANE+%7C+C12H26+%7C+ChemSpider&rft.identifier=https%3A%2F%2Fwww.chemspider.com%2FChemical-Structure.24272.html"> </span></span>
</li>
<li id="cite_note-10"><span class="mw-cite-backlink"><a href="#cite_ref-10">↑</a></span> <span class="reference-text"><span class="cite"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.452929.html"><i>4-Ethyldecane | C12H26 | ChemSpider.</i></a><span class="Abrufdatum"> Abgerufen am 17. März 2024</span>.</span><span style="display: none;" class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rfr_id=info%3Asid%2Fde.wikipedia.org%3ADodecane&rft.title=4-Ethyldecane+%7C+C12H26+%7C+ChemSpider&rft.description=4-Ethyldecane+%7C+C12H26+%7C+ChemSpider&rft.identifier=https%3A%2F%2Fwww.chemspider.com%2FChemical-Structure.452929.html"> </span></span>
</li>
<li id="cite_note-12"><span class="mw-cite-backlink"><a href="#cite_ref-12">↑</a></span> <span class="reference-text"><span class="cite"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.458928.html"><i>3,6-Diethyloctane | C12H26 | ChemSpider.</i></a><span class="Abrufdatum"> Abgerufen am 17. März 2024</span>.</span><span style="display: none;" class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rfr_id=info%3Asid%2Fde.wikipedia.org%3ADodecane&rft.title=3%2C6-Diethyloctane+%7C+C12H26+%7C+ChemSpider&rft.description=3%2C6-Diethyloctane+%7C+C12H26+%7C+ChemSpider&rft.identifier=https%3A%2F%2Fwww.chemspider.com%2FChemical-Structure.458928.html"> </span></span>
</li>
</ol>
<div class="mw-heading mw-heading2"><h2 id="Externe_Links_zu_erwähnten_Verbindungen"><span id="Externe_Links_zu_erw.C3.A4hnten_Verbindungen"></span>Externe Links zu erwähnten Verbindungen</h2></div>
<ol class="references" data-mw-group="S">
<li id="cite_note-:0-6"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-:0_6-0">a</a></sup> <sup><a href="#cite_ref-:0_6-1">b</a></sup></span> <span class="reference-text">Externe Identifikatoren von bzw. Datenbank-Links zu <span style="font-style:italic">2,2,4,6,6-Pentamethylheptan</span>: <a href="CAS-Nummer" title="CAS-Nummer">CAS-Nr.</a>: <span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=13475-82-6">13475-82-6</a><span class="editoronly" style="display:none;"></span>, <a href="EG-Nummer" title="EG-Nummer">EG-Nr.</a>: <span class="wikidata-content">236-757-0</span><span style="display:none;"></span>, <a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard: <span class="wikidata-content"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.033.401">100.033.401</a></span><span style="display:none;"></span>, <a href="PubChem" title="PubChem">PubChem</a>: <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/26058">26058</a>, <a href="ChemSpider" title="ChemSpider">ChemSpider</a>: <a rel="nofollow" class="external text" href="http://www.chemspider.com/Chemical-Structure.24272.html"><span class="wikidata-content">24272</span></a><span style="display:none;"></span>, <a href="Wikidata" title="Wikidata">Wikidata</a>: <a href="https://www.wikidata.org/wiki/Q27147086" class="extiw external" title="d:Q27147086">Q27147086</a>.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-11"><span class="mw-cite-backlink"><a href="#cite_ref-11">↑</a></span> <span class="reference-text">Externe Identifikatoren von bzw. Datenbank-Links zu <span style="font-style:italic">4-Ethyldecan</span>: <a href="CAS-Nummer" title="CAS-Nummer">CAS-Nr.</a>: <span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1636-44-8">1636-44-8</a><span class="editoronly" style="display:none;"></span>, <a href="PubChem" title="PubChem">PubChem</a>: <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/519256">519256</a>, <a href="Wikidata" title="Wikidata">Wikidata</a>: <a href="https://www.wikidata.org/wiki/Q82913057" class="extiw external" title="d:Q82913057">Q82913057</a>.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-13"><span class="mw-cite-backlink"><a href="#cite_ref-13">↑</a></span> <span class="reference-text">Externe Identifikatoren von bzw. Datenbank-Links zu <span style="font-style:italic">3,6-Diethyloctan</span>: <a href="CAS-Nummer" title="CAS-Nummer">CAS-Nr.</a>: <span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=62183-94-2">62183-94-2</a><span class="editoronly" style="display:none;"></span>, <a href="PubChem" title="PubChem">PubChem</a>: <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/526424">526424</a>, <a href="Wikidata" title="Wikidata">Wikidata</a>: <a href="https://www.wikidata.org/wiki/Q82102258" class="extiw external" title="d:Q82102258">Q82102258</a>.<span class="editoronly" style="display:none;"></span></span>
</li>
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