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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">2-Decanol</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>
</td></tr>
<tr>
<td colspan="2" style="text-align:center; font-size:80%;">Vereinfachte Strukturformel ohne <a href="Stereochemie" title="Stereochemie">Stereochemie</a>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>2-Decanol
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>Methyloctylcarbinol</li>
<li>Decan-2-ol</li>
<li>2-Decylalkohol</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>10</sub>H<sub>22</sub>O
</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=1120-06-5">1120-06-5</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=33758-16-6">33758-16-6</a><span class="editoronly" style="display:none;"></span> [(<i>S</i>)-Form]</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>
<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a>
</td>
<td colspan="2">214-296-6
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.012.997">100.012.997</a>
</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/14254">14254</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/Q31838883" class="extiw external" title="d:Q31838883">Q31838883</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>158,28 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>0,827 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>
<p>−6 bis −4 <a href="Grad_Celsius" title="Grad Celsius">°C</a><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>
<td><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>
<p>211 °C<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>
</p>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<ul><li>löslich in Ethanol und Benzol<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>mischbar mit Aceton<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>
<li>praktisch unlöslich in Wasser<sup id="cite_ref-Richard_Daley_3-0" class="reference"><a href="#cite_note-Richard_Daley-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<td><a href="Brechungsindex" title="Brechungsindex">Brechungsindex</a>
</td>
<td>
<p>1,434 (20 °C)<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>
</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_1-6" 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><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table>
<p>
</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><i>keine H-Sätze</i>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i><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>
</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>2-Decanol</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Gruppe der <a href="Alkohole" title="Alkohole">Alkohole</a>, genauer der <a href="Chiralit%C3%A4t_(Chemie)" title="Chiralität (Chemie)">chiralen</a> Alkohole.
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>2-Decanol kommt natürlich in der <a href="Weinraute" title="Weinraute">Weinraute</a><sup id="cite_ref-Dr._Dukes_46864_4-0" class="reference"><a href="#cite_note-Dr._Dukes_46864-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> und den Mandibeldrüsen von Termiten<sup id="cite_ref-E._David_Morgan,_N._Bhushan_Mandava_5-0" class="reference"><a href="#cite_note-E._David_Morgan,_N._Bhushan_Mandava-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> vor.
</p>
<div style="clear:left;"></div>
<div class="mw-heading mw-heading2"><h2 id="Gewinnung_und_Darstellung">Gewinnung und Darstellung</h2></div>
<p>2-Decanol kann durch radikal katalysierte Addition von <a href="1-Octen" title="1-Octen">1-Octen</a> mit einem <a href="Aldehyd" class="mw-redirect" title="Aldehyd">Aldehyd</a> gewonnen werden.<sup id="cite_ref-Richard_O.C._Norman,_James_M._Coxon_6-0" class="reference"><a href="#cite_note-Richard_O.C._Norman,_James_M._Coxon-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Es kann auch durch <a href="Hydrierung" title="Hydrierung">Hydrierung</a> von 1-Octyloxiran mit <a href="Raney-Nickel" title="Raney-Nickel">Raney-Nickel</a> gewonnen werden.<sup id="cite_ref-Michael_B._Smith_7-0" class="reference"><a href="#cite_note-Michael_B._Smith-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Das (<i>R</i>)-<a href="Isomer" class="mw-redirect" title="Isomer">Isomer</a> kann durch enzymatische Reduktion des Ketons gewonnen werden.<sup id="cite_ref-Xuebing_Xu,_Zheng_Guo,_Ling-Zhi_Cheong_8-0" class="reference"><a href="#cite_note-Xuebing_Xu,_Zheng_Guo,_Ling-Zhi_Cheong-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>2-Decanol ist eine farblose Flüssigkeit,<sup id="cite_ref-Sigma_1-8" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> die praktisch unlöslich in Wasser ist.<sup id="cite_ref-Richard_Daley_3-1" class="reference"><a href="#cite_note-Richard_Daley-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>2-Decanol kann als Substrat für biochemische Untersuchungen verwendet werden.<sup id="cite_ref-Sigma_1-9" 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> <sup><a href="#cite_ref-Sigma_1-8">i</a></sup> <sup><a href="#cite_ref-Sigma_1-9">j</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/118311">2-Decanol, 98%</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 24. April 2017 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/118311?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></span> <span class="reference-text">William M. Haynes: <cite style="font-style:italic">CRC Handbook of Chemistry and Physics, 97th Edition</cite>. CRC Press, 2016, ISBN 978-1-4987-5429-3, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>70</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=VVezDAAAQBAJ&pg=RA3-PA70#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:2-Decanol&rft.au=William+M.+Haynes&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics%2C+97th+Edition&rft.date=2016&rft.genre=book&rft.isbn=9781498754293&rft.pages=70&rft.pub=CRC+Press" style="display:none"> </span></span>
</li>
<li id="cite_note-Richard_Daley-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Richard_Daley_3-0">a</a></sup> <sup><a href="#cite_ref-Richard_Daley_3-1">b</a></sup></span> <span class="reference-text">Richard Daley: <cite style="font-style:italic">Organic Chemistry, Part 1 of 3</cite>. Lulu.com, 2005, ISBN 978-1-304-67486-9, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>178</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=y8xEAgAAQBAJ&pg=PA178#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:2-Decanol&rft.au=Richard+Daley&rft.btitle=Organic+Chemistry%2C+Part+1+of+3&rft.date=2005&rft.genre=book&rft.isbn=9781304674869&rft.pages=178&rft.pub=Lulu.com" style="display:none"> </span></span>
</li>
<li id="cite_note-Dr._Dukes_46864-4"><span class="mw-cite-backlink"><a href="#cite_ref-Dr._Dukes_46864_4-0">↑</a></span> <span class="reference-text"><span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://phytochem.nal.usda.gov/phytochem/chemicals/show/46864">2-DECYL-ALCOHOL</a></span> (englisch). In: <i>Dr. Duke's Phytochemical and Ethnobotanical Database</i>, Hrsg. <a href="Landwirtschaftsministerium_der_Vereinigten_Staaten" title="Landwirtschaftsministerium der Vereinigten Staaten">U.S. Department of Agriculture</a>, abgerufen am 28. Juli 2024.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-E._David_Morgan,_N._Bhushan_Mandava-5"><span class="mw-cite-backlink"><a href="#cite_ref-E._David_Morgan,_N._Bhushan_Mandava_5-0">↑</a></span> <span class="reference-text">E. David Morgan, N. Bhushan Mandava: <cite style="font-style:italic">Handbook of Natural Pesticides Pheromono</cite>. CRC Press, 1988, ISBN 978-0-8493-3658-4, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>137</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=qR_9wD5YOD8C&pg=PA137#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:2-Decanol&rft.au=E.+David+Morgan%2C+N.+Bhushan+Mandava&rft.btitle=Handbook+of+Natural+Pesticides+Pheromono&rft.date=1988&rft.genre=book&rft.isbn=9780849336584&rft.pages=137&rft.pub=CRC+Press" style="display:none"> </span></span>
</li>
<li id="cite_note-Richard_O.C._Norman,_James_M._Coxon-6"><span class="mw-cite-backlink"><a href="#cite_ref-Richard_O.C._Norman,_James_M._Coxon_6-0">↑</a></span> <span class="reference-text">Richard O.C. Norman, James M. Coxon: <cite style="font-style:italic">Principles of Organic Synthesis, 3rd Edition</cite>. CRC Press, 1993, ISBN 978-0-7487-6162-3, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>538</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=irNujn8i7rsC&pg=PA538#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:2-Decanol&rft.au=Richard+O.C.+Norman%2C+James+M.+Coxon&rft.btitle=Principles+of+Organic+Synthesis%2C+3rd+Edition&rft.date=1993&rft.genre=book&rft.isbn=9780748761623&rft.pages=538&rft.pub=CRC+Press" style="display:none"> </span></span>
</li>
<li id="cite_note-Michael_B._Smith-7"><span class="mw-cite-backlink"><a href="#cite_ref-Michael_B._Smith_7-0">↑</a></span> <span class="reference-text">Michael B. Smith: <cite style="font-style:italic">Organic Synthesis</cite>. Academic Press, 2011, ISBN 978-0-12-415884-9, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>443</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=YgNSCInB-RQC&pg=PA443#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:2-Decanol&rft.au=Michael+B.+Smith&rft.btitle=Organic+Synthesis&rft.date=2011&rft.genre=book&rft.isbn=9780124158849&rft.pages=443&rft.pub=Academic+Press" style="display:none"> </span></span>
</li>
<li id="cite_note-Xuebing_Xu,_Zheng_Guo,_Ling-Zhi_Cheong-8"><span class="mw-cite-backlink"><a href="#cite_ref-Xuebing_Xu,_Zheng_Guo,_Ling-Zhi_Cheong_8-0">↑</a></span> <span class="reference-text">Xuebing Xu, Zheng Guo, Ling-Zhi Cheong: <cite style="font-style:italic">Ionic Liquids in Lipid Processing and Analysis Opportunities and Challenges</cite>. Elsevier, 2016, ISBN 978-1-63067-048-1, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>32</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=_U2XCgAAQBAJ&pg=PA32#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:2-Decanol&rft.au=Xuebing+Xu%2C+Zheng+Guo%2C+Ling-Zhi+Cheong&rft.btitle=Ionic+Liquids+in+Lipid+Processing+and+Analysis+Opportunities+and+Challenges&rft.date=2016&rft.genre=book&rft.isbn=9781630670481&rft.pages=32&rft.pub=Elsevier" style="display:none"> </span></span>
</li>
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