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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Butandiole</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"><p><b>Butandiole</b> (synonym auch <i>Butylenglycole</i>) sind kettenförmige <a href="Organische_Verbindung" class="mw-redirect" title="Organische Verbindung">organische Verbindungen</a> aus vier <a href="Kohlenstoff" title="Kohlenstoff">Kohlenstoff</a>- und acht <a href="Wasserstoff" title="Wasserstoff">Wasserstoffatomen</a> sowie zwei <a href="Hydroxygruppe" title="Hydroxygruppe">Hydroxygruppen</a>, somit <a href="Diol" class="mw-redirect" title="Diol">Diole</a>.
</p><p>Je nach Anordnung der Hydroxygruppe unterscheidet man – unter Vernachlässigung der <a href="Stereochemie" title="Stereochemie">Stereochemie</a> – vier Butandiole. 1,2-Butandiol und 1,3-Butandiol sind <a href="Chiralit%C3%A4t_(Chemie)" title="Chiralität (Chemie)">chiral</a> und enthalten je ein <a href="Stereozentrum" title="Stereozentrum">Stereozentrum</a>. Entsprechend gibt es zwei <a href="Stereoisomere" class="mw-redirect" title="Stereoisomere">Stereoisomere</a>: (<i>R</i>)-1,2-Butandiol und (<i>S</i>)-1,2-Butandiol sowie (<i>R</i>)-1,3-Butandiol und (<i>S</i>)-1,3-Butandiol. 2,3-Butandiol enthält zwei Stereozentren mit dem gleichen Substitutionsmuster, somit existieren drei Stereoisomere: (<i>R</i>,<i>R</i>)-2,3-Butandiol, (<i>S</i>,<i>S</i>)-2,3-Butandiol und <i><a href="Meso-Verbindung" title="Meso-Verbindung">meso</a></i>-2,3-Butandiol.
</p>
<table class="wikitable centered" style="text-align:center;">
<tbody><tr>
<td class="hintergrundfarbe6" colspan="12"><b>Butandiole</b>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Strukturformel" title="Strukturformel">Strukturformel</a>
</td>
<td><span typeof="mw:File"></span>
</td>
<td><span typeof="mw:File"></span>
</td>
<td><span typeof="mw:File"></span>
</td>
<td><span typeof="mw:File"></span>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left">Name
</td>
<td><a href="1%2C2-Butandiol" title="1,2-Butandiol">1,2-Butandiol</a>
</td>
<td><a href="1%2C3-Butandiol" title="1,3-Butandiol">1,3-Butandiol</a>
</td>
<td><a href="1%2C4-Butandiol" title="1,4-Butandiol">1,4-Butandiol</a>
</td>
<td><a href="2%2C3-Butandiol" title="2,3-Butandiol">2,3-Butandiol</a>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left">Stereoisomere
</td>
<td>(<i>R</i>)-1,2-Butandiol<br>(<i>S</i>)-1,2-Butandiol
</td>
<td>(<i>R</i>)-1,3-Butandiol<br>(<i>S</i>)-1,3-Butandiol
</td>
<td>keine
</td>
<td>(<i>R</i>,<i>R</i>)-2,3-Butandiol<br>(<i>S</i>,<i>S</i>)-2,3-Butandiol<br>(<i>R</i>,<i>S</i>)-2,3-Butandiol
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=584-03-2">584-03-2</a><span class="editoronly" style="display:none;"></span><br><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=40348-66-1">40348-66-1</a><span class="editoronly" style="display:none;"></span> (<i>R</i>)<br><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">73522-17-5</span><span class="editoronly" style="display:none;"></span> (<i>S</i>)
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=107-88-0">107-88-0</a><span class="editoronly" style="display:none;"></span><br><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=6290-03-5">6290-03-5</a><span class="editoronly" style="display:none;"></span> (<i>R</i>)<br><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=24621-61-2">24621-61-2</a><span class="editoronly" style="display:none;"></span> (<i>S</i>)
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=110-63-4">110-63-4</a><span class="editoronly" style="display:none;"></span>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=513-85-9">513-85-9</a><span class="editoronly" style="display:none;"></span><br><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=24347-58-8">24347-58-8</a><span class="editoronly" style="display:none;"></span> (<i>R</i>,<i>R</i>)<br><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=19132-06-0">19132-06-0</a><span class="editoronly" style="display:none;"></span> (<i>S</i>,<i>S</i>)<br><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=5341-95-7">5341-95-7</a><span class="editoronly" style="display:none;"></span> (<i>R</i>,<i>S</i>)
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/11429">11429</a>
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/7896">7896</a>
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/8064">8064</a>
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/262">262</a>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="ECHA" class="mw-redirect" title="ECHA">ECHA</a>-Infocard
</td>
<td><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.008.663">100.008.663</a>
</td>
<td><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.003.209">100.003.209</a>
</td>
<td><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.003.443">100.003.443</a>
</td>
<td><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.007.431">100.007.431</a>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>−114 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-GESTIS-12_1-0" class="reference"><a href="#cite_note-GESTIS-12-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td>
<td><−50 °C<sup id="cite_ref-GESTIS-13_2-0" class="reference"><a href="#cite_note-GESTIS-13-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td>
<td>20 °C<sup id="cite_ref-GESTIS-14_3-0" class="reference"><a href="#cite_note-GESTIS-14-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</td>
<td>19 °C<sup id="cite_ref-GESTIS-23_4-0" class="reference"><a href="#cite_note-GESTIS-23-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>192 °C<sup id="cite_ref-GESTIS-12_1-1" class="reference"><a href="#cite_note-GESTIS-12-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td>
<td>207 °C<sup id="cite_ref-GESTIS-13_2-1" class="reference"><a href="#cite_note-GESTIS-13-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td>
<td>230 °C<sup id="cite_ref-GESTIS-14_3-1" class="reference"><a href="#cite_note-GESTIS-14-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</td>
<td>180 °C<sup id="cite_ref-GESTIS-23_4-1" class="reference"><a href="#cite_note-GESTIS-23-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Dichte" title="Dichte">Dichte</a> (20 °C)
</td>
<td>1,01 g·cm<sup>−3</sup><sup id="cite_ref-GESTIS-12_1-2" class="reference"><a href="#cite_note-GESTIS-12-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td>
<td>1,01 g·cm<sup>−3</sup><sup id="cite_ref-GESTIS-13_2-2" class="reference"><a href="#cite_note-GESTIS-13-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td>
<td>1,02 g·cm<sup>−3</sup><sup id="cite_ref-GESTIS-14_3-2" class="reference"><a href="#cite_note-GESTIS-14-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</td>
<td>1,01 g·cm<sup>−3</sup><sup id="cite_ref-GESTIS-23_4-2" class="reference"><a href="#cite_note-GESTIS-23-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Flammpunkt" title="Flammpunkt">Flammpunkt</a>
</td>
<td>102 °C<sup id="cite_ref-GESTIS-12_1-3" class="reference"><a href="#cite_note-GESTIS-12-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td>
<td>116 °C<sup id="cite_ref-GESTIS-13_2-3" class="reference"><a href="#cite_note-GESTIS-13-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td>
<td>ca. 130 °C<sup id="cite_ref-GESTIS-14_3-3" class="reference"><a href="#cite_note-GESTIS-14-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</td>
<td>85 °C<sup id="cite_ref-GESTIS-23_4-3" class="reference"><a href="#cite_note-GESTIS-23-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Toxizit%C3%A4t" title="Toxizität">Toxikologische Daten</a>
</td>
<td>16 000 mg·kg<sup>−1</sup> (<a href="Letale_Dosis" title="Letale Dosis">LD<sub>50</sub></a>, <a href="Ratten" title="Ratten">Ratte</a>, <a href="Peroral" title="Peroral">oral</a>)<sup id="cite_ref-GESTIS-12_1-4" class="reference"><a href="#cite_note-GESTIS-12-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><span class="editoronly" style="display:none;"></span>
</td>
<td>18 600 mg·kg<sup>−1</sup> (<a href="Letale_Dosis" title="Letale Dosis">LD<sub>50</sub></a>, <a href="Ratten" title="Ratten">Ratte</a>, <a href="Peroral" title="Peroral">oral</a>)<sup id="cite_ref-GESTIS-13_2-4" class="reference"><a href="#cite_note-GESTIS-13-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><span class="editoronly" style="display:none;"></span>
</td>
<td>1 530 mg·kg<sup>−1</sup> (<a href="Letale_Dosis" title="Letale Dosis">LD<sub>50</sub></a>, <a href="Ratten" title="Ratten">Ratte</a>, <a href="Peroral" title="Peroral">oral</a>)<sup id="cite_ref-GESTIS-14_3-4" class="reference"><a href="#cite_note-GESTIS-14-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><span class="editoronly" style="display:none;"></span>
</td>
<td>>5000 mg·kg<sup>−1</sup> (<a href="Letale_Dosis" title="Letale Dosis">LD<sub>50</sub></a>, <a href="Ratten" title="Ratten">Ratte</a>, <a href="Peroral" title="Peroral">oral</a>)<sup id="cite_ref-merck-23_5-0" class="reference"><a href="#cite_note-merck-23-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><span class="editoronly" style="display:none;"></span>
</td></tr></tbody></table>
<p>Die weiter denkbaren Butandiole 1,1-Butandiol und 2,2-Butandiol sind nach der <a href="Erlenmeyerregel" class="mw-redirect" title="Erlenmeyerregel">Erlenmeyerregel</a> als <a href="Geminal" title="Geminal">geminale</a> <a href="Diole" title="Diole">Diole</a> nicht stabil, da die Hydroxygruppen am gleichen C-Atom gebunden sind und daher zur Abspaltung von Wasser neigen.
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>Alle Butandiole dienen als <a href="Glycerin" title="Glycerin">Glycerinersatz</a> und Lösungsmittel sowie zur Synthese von Kunststoffen und Epoxidharzen.
</p>
<div class="mw-heading mw-heading2"><h2 id="Weblinks">Weblinks</h2></div>
<div class="sisterproject" style="margin:0.1em 0 0 0;"><div class="noresize noviewer" style="display:inline-block; line-height:10px; min-width:1.6em; text-align:center;" aria-hidden="true" role="presentation"><span class="mw-default-size" typeof="mw:File"><span title="Commons"></span></span></div><b><span class=""><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Butanediols?uselang=de"><span lang="en">Commons</span>: Butandiole</a></span></b> – Sammlung von Bildern, Videos und Audiodateien</div>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-GESTIS-12-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-GESTIS-12_1-0">a</a></sup> <sup><a href="#cite_ref-GESTIS-12_1-1">b</a></sup> <sup><a href="#cite_ref-GESTIS-12_1-2">c</a></sup> <sup><a href="#cite_ref-GESTIS-12_1-3">d</a></sup> <sup><a href="#cite_ref-GESTIS-12_1-4">e</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=022540">1,2-Butandiol</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 7. August 2019.<small class="noscript"><span></span> (JavaScript erforderlich)</small></span>
</li>
<li id="cite_note-GESTIS-13-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-GESTIS-13_2-0">a</a></sup> <sup><a href="#cite_ref-GESTIS-13_2-1">b</a></sup> <sup><a href="#cite_ref-GESTIS-13_2-2">c</a></sup> <sup><a href="#cite_ref-GESTIS-13_2-3">d</a></sup> <sup><a href="#cite_ref-GESTIS-13_2-4">e</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=012070">1,3-Butandiol</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 22. Dezember 2019.<small class="noscript"><span></span> (JavaScript erforderlich)</small></span>
</li>
<li id="cite_note-GESTIS-14-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-GESTIS-14_3-0">a</a></sup> <sup><a href="#cite_ref-GESTIS-14_3-1">b</a></sup> <sup><a href="#cite_ref-GESTIS-14_3-2">c</a></sup> <sup><a href="#cite_ref-GESTIS-14_3-3">d</a></sup> <sup><a href="#cite_ref-GESTIS-14_3-4">e</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=015800">1,4-Butandiol</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. April 2019.<small class="noscript"><span></span> (JavaScript erforderlich)</small></span>
</li>
<li id="cite_note-GESTIS-23-4"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-GESTIS-23_4-0">a</a></sup> <sup><a href="#cite_ref-GESTIS-23_4-1">b</a></sup> <sup><a href="#cite_ref-GESTIS-23_4-2">c</a></sup> <sup><a href="#cite_ref-GESTIS-23_4-3">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=022550">2,3-Butandiol</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 29. Mai 2018.<small class="noscript"><span></span> (JavaScript erforderlich)</small></span>
</li>
<li id="cite_note-merck-23-5"><span class="mw-cite-backlink"><a href="#cite_ref-merck-23_5-0">↑</a></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-818801?Origin=PDP">Butandiole</a></span> bei <a href="Merck_KGaA" title="Merck KGaA">Merck</a>, abgerufen am 18. Januar 2011.<span class="editoronly" style="display:none;"></span></span>
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