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<title>2-Nonanol</title>
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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">2-Nonanol</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>
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<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>
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<tr>
<td colspan="2" style="text-align:center; font-size:80%;">(<i>R</i>)-2-Nonanol (oben) und (<i>S</i>)-2-Nonanol (unten)
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>2-Nonanol
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>Nonan-2-ol</li>
<li>Heptylmethylcarbinol</li>
<li>Methylheptylcarbinol</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>9</sub>H<sub>20</sub>O
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>farblose Flüssigkeit<sup id="cite_ref-gestis_1-0" class="reference"><a href="#cite_note-gestis-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=628-99-9">628-99-9</a><span class="editoronly" style="display:none;"></span> <small>(<a href="Racemat" title="Racemat">Racemat</a>)</small></li>
<li><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">70419-06-6</span><span class="editoronly" style="display:none;"></span> <small>[(<i>S</i>)-(+)-2-Nonanol]</small></li>
<li><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">70419-07-7</span><span class="editoronly" style="display:none;"></span> <small>[(<i>R</i>)-(–)-2-Nonanol]</small></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">211-065-1
</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/100.010.060">100.010.060</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/12367">12367</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/Q4596913" class="extiw external" title="d:Q4596913">Q4596913</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>144,26 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
</p>
</td></tr>
<tr>
<td><a href="Dichte" title="Dichte">Dichte</a>
</td>
<td>
<p>0,82 g·cm<sup>−3</sup> <small>(Racemat)</small><sup id="cite_ref-Merck_2-0" class="reference"><a href="#cite_note-Merck-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>−35 <a href="Grad_Celsius" title="Grad Celsius">°C</a> <small>(Racemat)</small><sup id="cite_ref-Merck_2-1" class="reference"><a href="#cite_note-Merck-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>
<p>198 °C <small>(Racemat)</small><sup id="cite_ref-Merck_2-2" class="reference"><a href="#cite_note-Merck-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<p>nahezu unlöslich in Wasser<sup id="cite_ref-Merck_2-3" class="reference"><a href="#cite_note-Merck-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Brechungsindex" title="Brechungsindex">Brechungsindex</a>
</td>
<td>
<p>1,429<sup id="cite_ref-Merck_2-4" class="reference"><a href="#cite_note-Merck-2"><span class="cite-bracket">[</span>2<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-gestis_1-1" class="reference"><a href="#cite_note-gestis-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-gestis_1-2" class="reference"><a href="#cite_note-gestis-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-Nonanol</b> ist eine natürlich vorkommende <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Stoffgruppe der <a href="Aliphatische_Kohlenwasserstoffe" title="Aliphatische Kohlenwasserstoffe">aliphatischen</a> <a href="Alkohole" title="Alkohole">Alkohole</a>. Neben beiden <a href="Enantiomere" class="mw-redirect" title="Enantiomere">Enantiomeren</a> (<i>R</i>)-2-Nonanol und (<i>S</i>)-2-Nonanol existieren weitere Strukturisomere, zum Beispiel das <a href="1-Nonanol" title="1-Nonanol">1-Nonanol</a>, <a href="3-Nonanol" title="3-Nonanol">3-Nonanol</a> und <a href="4-Nonanol" title="4-Nonanol">4-Nonanol</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Natürlich kommt Nonan-2-ol in <a href="Ingwer" title="Ingwer">Ingwer</a> (<i>Zingiber officinale</i>),<sup id="cite_ref-roempp_3-0" class="reference"><a href="#cite_note-roempp-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> dem Aromaextrakt der <a href="Wald-Erdbeere" title="Wald-Erdbeere">Wald-Erdbeeren</a>,<sup id="cite_ref-ZNF1973-488_4-0" class="reference"><a href="#cite_note-ZNF1973-488-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> in <a href="Dill_(Pflanze)" title="Dill (Pflanze)">Dill</a> (<i>Anethum graveolens</i>),<sup id="cite_ref-Dr._Dukes_5-0" class="reference"><a href="#cite_note-Dr._Dukes-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="Boldo" title="Boldo">Boldo</a> (<i>Peumus boldus</i>),<sup id="cite_ref-Dr._Dukes_5-1" class="reference"><a href="#cite_note-Dr._Dukes-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="Weinraute" title="Weinraute">Weinraute</a> (<i>Ruta graveolens</i>),<sup id="cite_ref-Dr._Dukes_5-2" class="reference"><a href="#cite_note-Dr._Dukes-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> dem <a href="Gew%C3%BCrznelkenbaum" title="Gewürznelkenbaum">Gewürznelkenbaum</a> (<i>Syzygium aromaticum</i>),<sup id="cite_ref-Dr._Dukes_5-3" class="reference"><a href="#cite_note-Dr._Dukes-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
und in den Sekreten einer Reihe von <a href="Insekten" title="Insekten">Insekten</a><sup id="cite_ref-roempp_3-1" class="reference"><a href="#cite_note-roempp-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> vor. Der Alkohol ist ein <a href="Pheromon" title="Pheromon">Pheromon</a> der <a href="Honigbiene" class="mw-redirect" title="Honigbiene">Honigbiene</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Von 2-Nonanol existieren zwei <a href="Stereoisomere" class="mw-redirect" title="Stereoisomere">Stereoisomere</a>. Praktische Bedeutung hat allerdings nur das <a href="Racemat" title="Racemat">Racemat</a>. Dieses hat einen Schmelzpunkt bei −35 °C.<sup id="cite_ref-Merck_2-5" class="reference"><a href="#cite_note-Merck-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Der Siedepunkt unter <a href="Normaldruck" class="mw-redirect" title="Normaldruck">Normaldruck</a> liegt bei 198 °C.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Die <a href="Dampfdruck" title="Dampfdruck">Dampfdruckfunktion</a> ergibt sich nach <a href="Antoine-Gleichung" title="Antoine-Gleichung">Antoine</a> entsprechend log<sub>10</sub>(P) = A−(B/(T+C)) (P in Pa, T in °C) mit A = 10,179, B = 1961,437 und C = 189,330 im Temperaturbereich von 253 bis 353 K.<sup id="cite_ref-Guimbi_7-0" class="reference"><a href="#cite_note-Guimbi-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Die <a href="Kritischer_Punkt_(Thermodynamik)" title="Kritischer Punkt (Thermodynamik)">kritische Temperatur</a> liegt bei 377 °C, der <a href="Kritischer_Druck" class="mw-redirect" title="Kritischer Druck">kritischer Druck</a> bei 25,3 bar und das kritische Volumen bei 0,575 l·mol<sup>−1</sup>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>
</p><p><span typeof="mw:File"></span>
</p><p>Die Dämpfe der schwer entzündbaren Flüssigkeit (Flammpunkt 82 °C)<sup id="cite_ref-gestis_1-3" class="reference"><a href="#cite_note-gestis-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> können mit Luft beim Erhitzen des Stoffes über seinen Flammpunkt explosive Gemische bilden.
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>Nonan-2-ol wird – ebenso wie die isomeren Nonan-3-ol und Nonan-4-ol – als Bestandteil von <a href="Parf%C3%BCm" title="Parfüm">Parfüms</a> sowie als <a href="Aromastoff" class="mw-redirect" title="Aromastoff">Aromastoff</a> in Lebensmitteln, etwa Backwaren, eingesetzt.<sup id="cite_ref-roempp_3-2" class="reference"><a href="#cite_note-roempp-3"><span class="cite-bracket">[</span>3<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-gestis-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-gestis_1-0">a</a></sup> <sup><a href="#cite_ref-gestis_1-1">b</a></sup> <sup><a href="#cite_ref-gestis_1-2">c</a></sup> <sup><a href="#cite_ref-gestis_1-3">d</a></sup></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=493573">2-Nonanol</a></span> in der <a href="GESTIS-Stoffdatenbank" title="GESTIS-Stoffdatenbank">GESTIS-Stoffdatenbank</a> des <a href="Institut_f%C3%BCr_Arbeitsschutz_der_Deutschen_Gesetzlichen_Unfallversicherung" title="Institut für Arbeitsschutz der Deutschen Gesetzlichen Unfallversicherung">IFA</a>, abgerufen am 24. Juli 2013.<small class="noscript"><span></span> (JavaScript erforderlich)</small></span>
</li>
<li id="cite_note-Merck-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Merck_2-0">a</a></sup> <sup><a href="#cite_ref-Merck_2-1">b</a></sup> <sup><a href="#cite_ref-Merck_2-2">c</a></sup> <sup><a href="#cite_ref-Merck_2-3">d</a></sup> <sup><a href="#cite_ref-Merck_2-4">e</a></sup> <sup><a href="#cite_ref-Merck_2-5">f</a></sup></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.merckmillipore.com/DE/de/product/msds/MDA_CHEM-818793?Origin=PDP">2-Nonanol zur Synthese</a></span> bei <a href="Merck_KGaA" title="Merck KGaA">Merck</a>, abgerufen am 24. Juli 2013.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-roempp-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-roempp_3-0">a</a></sup> <sup><a href="#cite_ref-roempp_3-1">b</a></sup> <sup><a href="#cite_ref-roempp_3-2">c</a></sup></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://roempp.thieme.de/lexicon/RD-14-01611"><i>Nonanole</i></a>. In: <i><a href="R%C3%B6mpp_Online" class="mw-redirect" title="Römpp Online">Römpp Online</a>.</i> Georg Thieme Verlag, abgerufen am 25. Juli 2013.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-ZNF1973-488-4"><span class="mw-cite-backlink"><a href="#cite_ref-ZNF1973-488_4-0">↑</a></span> <span class="reference-text">Friedrich Drawert, Roland Tressl, Günter Staudt, Hans Köppler: <i>Gaschromatographisch-massenspektrometrische Differenzierung von Erdbeerarten.</i> In: <i><a href="Zeitschrift_f%C3%BCr_Naturforschung_C" title="Zeitschrift für Naturforschung C">Zeitschrift für Naturforschung C</a>.</i> 28, 1973, S. 488–493 (<a rel="nofollow" class="external text" href="http://zfn.mpdl.mpg.de/data/Reihe_C/28/ZNC-1973-28c-0488.pdf">PDF</a>, freier Volltext).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Dr._Dukes-5"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Dr._Dukes_5-0">a</a></sup> <sup><a href="#cite_ref-Dr._Dukes_5-1">b</a></sup> <sup><a href="#cite_ref-Dr._Dukes_5-2">c</a></sup> <sup><a href="#cite_ref-Dr._Dukes_5-3">d</a></sup></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/47069">2-NONANOL</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 18. August 2024.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">Ellis, L.M.; Reid, E.E.: <i>The Preparation and Properties of A Double Series of Aliphatic Mercaptans</i> in <a href="J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a> 54 (1932) 1674–1687, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1021/ja01343a067">10.1021/ja01343a067</a></span>.</span>
</li>
<li id="cite_note-Guimbi-7"><span class="mw-cite-backlink"><a href="#cite_ref-Guimbi_7-0">↑</a></span> <span class="reference-text">N'Guimbi, J.; Berro, C.; Mokbel, I.; Rauzy, E.; Jose, J.: <i>Experimental vapour pressure of 13 secondary and ternary alcohols - correlation and prediction by group contribution method</i> in Fluid Phase Equilibria 162 (1999) 143–158, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1016/S0378-3812%2899%2900168-5">10.1016/S0378-3812(99)00168-5</a></span>.</span>
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<li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">Gude, M.; Teja, A.S.: <i>Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols</i> in <a href="J._Chem._Eng._Data" class="mw-redirect" title="J. Chem. Eng. Data">J. Chem. Eng. Data</a> 40 (1995) 1025–1036, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1021/je00021a001">10.1021/je00021a001</a></span>.</span>
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