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1,5,9-cyclododecatrieen - Wikipedia
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class="firstHeading mw-first-heading"><span class="mw-page-title-main">1,5,9-cyclododecatrieen</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Ga naar een artikel in een andere taal. 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id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="nl" dir="ltr"><table class="infobox" cellpadding="1" cellspacing="1"> <tbody><tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center; font-size:120%;" colspan="3">1,5,9-cyclododecatrieen </th></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center;" colspan="3">Structuurformule en molecuulmodel </th></tr> <tr> <td style="text-align:center; padding:0;" colspan="3"><span typeof="mw:File"><a href="/wiki/Bestand:1,5,9-Cyclododecatriene.svg" class="mw-file-description"><img alt="Structuurformule van 1,5,9-cyclododecatrieen" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/1%2C5%2C9-Cyclododecatriene.svg/180px-1%2C5%2C9-Cyclododecatriene.svg.png" decoding="async" width="180" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/1%2C5%2C9-Cyclododecatriene.svg/270px-1%2C5%2C9-Cyclododecatriene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/1%2C5%2C9-Cyclododecatriene.svg/360px-1%2C5%2C9-Cyclododecatriene.svg.png 2x" data-file-width="620" data-file-height="620" /></a></span> </td></tr> <tr> <td style="text-align:center;" colspan="3"><div style="font-size:90%"><a href="/wiki/Structuurformule" title="Structuurformule">Structuurformule</a> van 1,5,9-cyclododecatrieen</div> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center;" colspan="3">Algemeen </th></tr> <tr> <th><a href="/wiki/Molecuulformule" title="Molecuulformule">Molecuulformule</a> </th> <td colspan="2">C<sub>12</sub>H<sub>18</sub> </td></tr> <tr> <th><a href="/wiki/IUPAC-nomenclatuur" title="IUPAC-nomenclatuur">IUPAC-naam</a> </th> <td colspan="2">cyclododeca-1,5,9-trieen </td></tr> <tr> <th><a href="/wiki/Molaire_massa" title="Molaire massa">Molmassa</a> </th> <td colspan="2">162,27 <a href="/wiki/Gram_(eenheid)" title="Gram (eenheid)">g</a>/<a href="/wiki/Mol_(eenheid)" title="Mol (eenheid)">mol</a> </td></tr> <tr> <th><a href="/wiki/SMILES" title="SMILES">SMILES</a> </th> <td colspan="2"><div style="word-wrap:break-word; width:127px;">C1CC=CCCC=CCCC=C1</div> </td></tr> <tr> <th><a href="/wiki/CAS-nummer" title="CAS-nummer">CAS-nummer</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=4904-61-4">4904-61-4</a> </td></tr> <tr> <th><a href="/wiki/EG-nummer" title="EG-nummer">EG-nummer</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="http://echa.europa.eu/web/guest/information-on-chemicals/cl-inventory-database/-/cl-inventory/search-clinventory-by-other-identifier/225-533-8">225-533-8</a> </td></tr> <tr> <th><a href="/wiki/PubChem" title="PubChem">PubChem</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5364361">5364361</a> </td></tr> <tr> <th><a href="/wiki/Wikidata" title="Wikidata">Wikidata</a> </th> <td colspan="2"><a href="https://www.wikidata.org/wiki/Q61739965" class="extiw" title="d:Q61739965">Q61739965</a> </td></tr> <tr> <th>Beschrijving </th> <td colspan="2">Kleurloze tot gele vloeistof </td></tr> <tr> <th>Vergelijkbaar met </th> <td colspan="2"><a href="/w/index.php?title=Trimethylcyclododecatrieen&action=edit&redlink=1" class="new" title="Trimethylcyclododecatrieen (de pagina bestaat niet)">trimethylcyclododecatrieen</a> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3">Waarschuwingen en veiligheidsmaatregelen </th></tr> <tr> <td class="ta-center" colspan="3"><table align="center" style="border-style:none;"><tbody><tr><td style="margin-left:auto;margin-right:auto;vertical-align:top;text-align:center;border-style:none;cell-padding:2px"><span typeof="mw:File"><a href="/wiki/Bestand:GHS-pictogram-acid.svg" class="mw-file-description" title="Corrosief"><img alt="Corrosief" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/60px-GHS-pictogram-acid.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/90px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/120px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span></td></tr></tbody></table><b>Gevaar</b> </td></tr> <tr> <th><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">H-zinnen</a> </th> <td colspan="2"><abbr title="Veroorzaakt ernstige brandwonden.">H314</abbr> </td></tr> <tr> <th><span class="nowrap"><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">EUH-zinnen</a></span> </th> <td colspan="2"><i>geen</i> </td></tr> <tr> <th><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">P-zinnen</a> </th> <td colspan="2"><abbr title="Beschermende handschoenen/beschermende kleding/oogbescherming/gelaatsbescherming dragen.">P280</abbr> - <abbr title="Bij contact met de ogen: voorzichtig afspoelen met water gedurende een aantal minuten; contactlenzen verwijderen, indien mogelijk; blijven spoelen.">P305+P351+P338</abbr>-<abbr title="Onmiddellijk een antigifcentrum of een arts raadplegen.">P310</abbr> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3">Fysische eigenschappen </th></tr> <tr> <th><a href="/wiki/Aggregatietoestand" title="Aggregatietoestand">Aggregatietoestand</a> </th> <td colspan="2">vloeibaar </td></tr> <tr> <th><a href="/wiki/Kleur_(hoofdbetekenis)" class="mw-redirect" title="Kleur (hoofdbetekenis)">Kleur</a> </th> <td colspan="2">kleurloos-geel </td></tr> <tr> <th><a href="/wiki/Massadichtheid" title="Massadichtheid">Dichtheid</a> </th> <td colspan="2">0,89 g/cm³ </td></tr> <tr> <th><a href="/wiki/Smeltpunt" title="Smeltpunt">Smeltpunt</a> </th> <td colspan="2">−17 °C </td></tr> <tr> <th><a href="/wiki/Kookpunt" title="Kookpunt">Kookpunt</a> </th> <td colspan="2">ca. 240 °C </td></tr> <tr> <th>Slecht oplosbaar in </th> <td colspan="2">water </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3"><small>Tenzij anders vermeld zijn <a href="/wiki/Standaardomstandigheden" title="Standaardomstandigheden">standaardomstandigheden</a> gebruikt (298,15 <a href="/wiki/Kelvin_(eenheid)" title="Kelvin (eenheid)">K</a> of 25 <a href="/wiki/Celsius" title="Celsius">°C</a>, 1 <a href="/wiki/Bar_(druk)" title="Bar (druk)">bar</a>).</small> </th></tr> <tr> <td class="infobox-kop notheme center" style="background-color:#DDEEFF; color:inherit;" colspan="3"> <table cellspacing="0" cellpadding="0"> <tbody><tr> <td style="vertical-align:middle;"><b>Portaal</b>  <span class="noviewer" typeof="mw:File"><a href="/wiki/Bestand:Portal.svg" class="mw-file-description" title="Portaalicoon"><img alt="Portaalicoon" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/22px-Portal.svg.png" decoding="async" width="22" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/33px-Portal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/44px-Portal.svg.png 2x" data-file-width="36" data-file-height="32" /></a></span>   </td> <td class="ta-left"><b><a href="/wiki/Portaal:Scheikunde" title="Portaal:Scheikunde">Scheikunde</a> </b> </td></tr></tbody></table> </td></tr> </tbody></table> <p><b>1,5,9-cyclododecatrieen</b> of <b>CDT</b> is een <a href="/wiki/Onverzadigde_verbinding" title="Onverzadigde verbinding">onverzadigde</a> <a href="/wiki/Cyclische_verbinding" title="Cyclische verbinding">cyclische</a> <a href="/wiki/Koolwaterstof" title="Koolwaterstof">koolwaterstof</a>, met drie <a href="/wiki/Dubbele_binding_(scheikunde)" title="Dubbele binding (scheikunde)">dubbele bindingen</a>. Het is het cyclisch <a href="/wiki/Trimeer" title="Trimeer">trimeer</a> van <a href="/wiki/1,3-butadieen" title="1,3-butadieen">1,3-butadieen</a>. Er bestaan vier <a href="/wiki/Stereo-isomerie" class="mw-redirect" title="Stereo-isomerie">stereo-isomeren</a> van: <i>E,E,E</i> of <i>trans,trans,trans</i>; <i>Z,Z,Z</i> of <i>cis,cis,cis</i>, <i>EZZ</i> en <i>EEZ</i>. </p> <div class="mw-heading mw-heading2"><h2 id="Synthese">Synthese</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1,5,9-cyclododecatrieen&veaction=edit&section=1" title="Bewerk dit kopje: Synthese" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=1,5,9-cyclododecatrieen&action=edit&section=1" title="De broncode bewerken van de sectie: Synthese"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>1,5,9-cyclododecatrieen wordt bereid door de cyclotrimerisatie van 1,3-butadieen. De reactie gebeurt in een <a href="/wiki/Apolaire_verbinding" title="Apolaire verbinding">apolair</a> <a href="/wiki/Oplosmiddel" title="Oplosmiddel">oplosmiddel</a> (bijvoorbeeld <a href="/wiki/Benzeen" title="Benzeen">benzeen</a>), waarin een <a href="/wiki/Katalysator" title="Katalysator">katalysator</a> is opgelost die een verbinding van een of meerdere <a href="/wiki/Overgangsmetaal" title="Overgangsmetaal">overgangsmetalen</a> bevat, bijvoorbeeld <a href="/wiki/Titanium(IV)chloride" title="Titanium(IV)chloride">titanium(IV)chloride</a>, en een <a href="/wiki/Organoaluminiumchemie" title="Organoaluminiumchemie">organoaluminiumverbinding</a> zoals <a href="/wiki/Di-ethylaluminiumchloride" title="Di-ethylaluminiumchloride">di-ethylaluminiumchloride</a> als cokatalysator:<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> </p> <dl><dd><figure class="mw-halign-left" typeof="mw:File"><a href="/wiki/Bestand:Synthesis_of_1,5,9-cyclododecatriene.svg" class="mw-file-description" title="Synthese van 1,5,9-cyclododecatrieen"><img alt="Synthese van 1,5,9-cyclododecatrieen" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Synthesis_of_1%2C5%2C9-cyclododecatriene.svg/370px-Synthesis_of_1%2C5%2C9-cyclododecatriene.svg.png" decoding="async" width="370" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Synthesis_of_1%2C5%2C9-cyclododecatriene.svg/555px-Synthesis_of_1%2C5%2C9-cyclododecatriene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/42/Synthesis_of_1%2C5%2C9-cyclododecatriene.svg/740px-Synthesis_of_1%2C5%2C9-cyclododecatriene.svg.png 2x" data-file-width="620" data-file-height="216" /></a><figcaption>Synthese van 1,5,9-cyclododecatrieen</figcaption></figure></dd></dl> <div style="clear:left;"></div> <p>Nevenproducten zijn andere cyclische of lineaire <a href="/wiki/Oligomeer" title="Oligomeer">oligomeren</a> van 1,3-butadieen zoals <a href="/wiki/1,5-cyclo-octadieen" title="1,5-cyclo-octadieen">1,5-cyclo-octadieen</a>, <a href="/wiki/4-vinylcyclohexeen" title="4-vinylcyclohexeen">4-vinylcyclohexeen</a> en laagmoleculair <a href="/wiki/Polybutadieen" title="Polybutadieen">polybutadieen</a>. 1,5,9-cyclododecatrieen wordt hieruit afgescheiden door middel van <a href="/wiki/Destillatie" title="Destillatie">destillatie</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Toepassingen">Toepassingen</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1,5,9-cyclododecatrieen&veaction=edit&section=2" title="Bewerk dit kopje: Toepassingen" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=1,5,9-cyclododecatrieen&action=edit&section=2" title="De broncode bewerken van de sectie: Toepassingen"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>1,5,9-cyclododecatrieen wordt gebruikt voor de productie van <a href="/w/index.php?title=1,12-dodecaandizuur&action=edit&redlink=1" class="new" title="1,12-dodecaandizuur (de pagina bestaat niet)">1,12-dodecaandizuur</a> en van het <a href="/wiki/Lactam" title="Lactam">lactam</a> <a href="/wiki/Laurolactam" title="Laurolactam">laurolactam</a>. Beide zijn <a href="/wiki/Monomeer" title="Monomeer">monomeren</a> voor de productie van respectievelijk <a href="/wiki/Polyester" title="Polyester">polyesters</a> en <a href="/wiki/Polyamide" title="Polyamide">polyamiden</a>. </p><p>De productie van 1,12-dodecaandizuur gebeurt door <a href="/wiki/Hydrogenering" title="Hydrogenering">hydrogenering</a> van 1,5,9-cyclododecatrieen tot <a href="/wiki/Cyclododecaan" title="Cyclododecaan">cyclododecaan</a> (<b>2</b>). Dat wordt <a href="/wiki/Oxidatie" title="Oxidatie">geoxideerd</a> met <a href="/wiki/Boorzuur" title="Boorzuur">boorzuur</a>. Daarbij ontstaan zowel het alcohol <a href="/wiki/Cyclododecanol" title="Cyclododecanol">cyclododecanol</a> <b>3a</b> als het keton <a href="/wiki/Cyclododecanon" title="Cyclododecanon">cyclododecanon</a> <b>3b</b>. Deze verbindingen worden dan met <a href="/wiki/Salpeterzuur" title="Salpeterzuur">salpeterzuur</a> omgezet in 1,12-dodecaandizuur: </p> <dl><dd><figure class="mw-halign-left" typeof="mw:File"><a href="/wiki/Bestand:Synthesis_of_1,12-dodecanedioic_acid.svg" class="mw-file-description" title="Synthese van 1,12-dodecaandizuur"><img alt="Synthese van 1,12-dodecaandizuur" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Synthesis_of_1%2C12-dodecanedioic_acid.svg/600px-Synthesis_of_1%2C12-dodecanedioic_acid.svg.png" decoding="async" width="600" height="236" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Synthesis_of_1%2C12-dodecanedioic_acid.svg/900px-Synthesis_of_1%2C12-dodecanedioic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/92/Synthesis_of_1%2C12-dodecanedioic_acid.svg/1200px-Synthesis_of_1%2C12-dodecanedioic_acid.svg.png 2x" data-file-width="620" data-file-height="244" /></a><figcaption>Synthese van 1,12-dodecaandizuur</figcaption></figure></dd></dl> <div style="clear:left;"></div> <p>Laurolactam wordt bereid door cyclododecanon om te zetten in <a href="/wiki/Cyclododecanonoxime" title="Cyclododecanonoxime">cyclododecanonoxime</a>, dat vervolgens een <a href="/wiki/Beckmann-omlegging" title="Beckmann-omlegging">Beckmann-omlegging</a> ondergaat tot laurolactam. </p><p>1,5,9-cyclododecatrieen wordt ook gebruikt voor de productie van de <a href="/wiki/Vlamvertrager" title="Vlamvertrager">vlamvertrager</a> <a href="/wiki/Hexabroomcyclododecaan" title="Hexabroomcyclododecaan">hexabroomcyclododecaan</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Externe_link">Externe link</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1,5,9-cyclododecatrieen&veaction=edit&section=3" title="Bewerk dit kopje: Externe link" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=1,5,9-cyclododecatrieen&action=edit&section=3" title="De broncode bewerken van de sectie: Externe link"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><style data-mw-deduplicate="TemplateStyles:r67679320">.mw-parser-output .taalaanduiding{font-family:sans-serif;font-size:85%;cursor:help;color:var(--color-subtle,#555)}.mw-parser-output .taalaanduiding span{border-bottom:1px dotted var(--color-subtle,#555)}</style><span class="taalaanduiding" title="Taal: Engels">(<span>en</span>) </span> <a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=024670&lang=en">Gegevens van <i>1,5,9-cyclododecatrieen</i></a> in de GESTIS-stoffendatabank van het IFA</li></ul> <div class="toccolours appendix" role="presentation" style="font-size:90%; margin:1em 0 -0.5em; clear:both;"> <div><span style="font-weight:bold">Bronnen, noten en/of referenties</span></div> <div class="reflist" style="list-style-type: decimal;"><div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://depatisnet.dpma.de/DepatisNet/depatisnet?action=bibdat&docid=BE000000555180A">Belgisch octrooi 555180, verleend op 20 augustus 1957 aan Studiengesellschaft Kohle (Duitsland)</a></span> </li> </ol></div></div> </div> <style data-mw-deduplicate="TemplateStyles:r67837862">.mw-parser-output .navigatie{position:relative;clear:both;overflow:auto;margin:1em auto -0.5em;padding:2px;background-color:var(--background-color-neutral-subtle,#f8f9fa);border:1px solid var(--border-color-base,#a2a9b1);text-align:center;font-size:87%}.mw-parser-output .navigatie-bewerken{margin-left:0.5em}.mw-parser-output .navigatie-bewerken .mw-ui-icon::before{background-size:0.9em}.mw-parser-output .navigatie-afb-links,.mw-parser-output .navigatie-afb-rechts{position:absolute}.mw-parser-output .navigatie-afb-rechts{right:2px}.mw-parser-output .navigatie-afb-groot{float:right;padding-left:0.5em}.mw-parser-output .navigatie-titel{background-color:#ddeef8;padding:2px 5.5em;font-weight:bold}.mw-parser-output .navigatie-inhoud{padding:0.5em}.mw-parser-output .navigatie-inhoud p:first-child{margin:0}.mw-parser-output .navigatie div[style*="background-color"],.mw-parser-output .navigatie div[style*="background"]{color:inherit}@media screen{html.skin-theme-clientpref-night .mw-parser-output .navigatie-titel{background-color:var(--background-color-interactive,#eaecf0)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navigatie-titel{background-color:var(--background-color-interactive,#eaecf0)!important}}</style> <div class="navigatie" role="navigation" aria-labelledby="Cycloalkenen"> <div class="navigatie-afb-links noviewer"><div class="navigatie-bewerken show-autoconfirmed nomobile"><span class="nowrap skin-invert-image"><span typeof="mw:File"><a href="/wiki/Sjabloon:Navigatie_cycloalkenen" title="Sjabloon:Navigatie cycloalkenen"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/OOjs_UI_icon_article-ltr.svg/16px-OOjs_UI_icon_article-ltr.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/OOjs_UI_icon_article-ltr.svg/24px-OOjs_UI_icon_article-ltr.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/OOjs_UI_icon_article-ltr.svg/32px-OOjs_UI_icon_article-ltr.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> · <span class="ui-state-disabled" typeof="mw:File"><span title="Overleg sjabloon (de pagina bestaat niet)"><img alt="Overleg sjabloon (de pagina bestaat niet)" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/OOjs_UI_icon_speechBubbles-ltr.svg/16px-OOjs_UI_icon_speechBubbles-ltr.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/OOjs_UI_icon_speechBubbles-ltr.svg/24px-OOjs_UI_icon_speechBubbles-ltr.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/40/OOjs_UI_icon_speechBubbles-ltr.svg/32px-OOjs_UI_icon_speechBubbles-ltr.svg.png 2x" data-file-width="20" data-file-height="20" /></span></span> · <span typeof="mw:File"><a href="//nl.wikipedia.org/w/index.php?title=Sjabloon:Navigatie_cycloalkenen&action=edit" title="Sjabloon bewerken"><img alt="Sjabloon bewerken" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/OOjs_UI_icon_edit-ltr.svg/16px-OOjs_UI_icon_edit-ltr.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/OOjs_UI_icon_edit-ltr.svg/24px-OOjs_UI_icon_edit-ltr.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/OOjs_UI_icon_edit-ltr.svg/32px-OOjs_UI_icon_edit-ltr.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></div></div> <div id="Cycloalkenen" class="navigatie-titel"><a href="/wiki/Cycloalkeen" title="Cycloalkeen">Cycloalkenen</a></div> <div class="navigatie-inhoud"> <style data-mw-deduplicate="TemplateStyles:r67785531">.mw-parser-output .navigatie-tabel{margin:0 auto 0 auto;text-align:left}.mw-parser-output .navigatie-tabel .links{text-align:right}.mw-parser-output .navigatie-tabel .rechts{padding-left:0.5em}@media screen and (max-width:640px){.mw-parser-output .navigatie-tabel tr{display:grid;grid-template-columns:1fr;width:100%;margin-bottom:0.5em}.mw-parser-output .navigatie-tabel tr:last-of-type{margin-bottom:0}.mw-parser-output .navigatie-tabel .links{text-align:unset}.mw-parser-output .navigatie-tabel .rechts{padding:unset}}</style><table class="navigatie-tabel vatop" cellpadding="0" cellspacing="0" style=""><tbody><tr><td class="links" style=""><b>Cycloalkeen:</b></td><td class="rechts"><a href="/wiki/Cyclopropeen" title="Cyclopropeen">Cyclopropeen</a> · <a href="/wiki/Cyclobuteen" title="Cyclobuteen">Cyclobuteen</a> · <a href="/wiki/Cyclopenteen" title="Cyclopenteen">Cyclopenteen</a> · <a href="/wiki/Cyclohexeen" title="Cyclohexeen">Cyclohexeen</a> · <a href="/wiki/Cyclohepteen" title="Cyclohepteen">Cyclohepteen</a> · <a href="/wiki/Cyclo-octeen" title="Cyclo-octeen">Cyclo-octeen</a> · <a href="/wiki/Cyclononeen" title="Cyclononeen">Cyclononeen</a></td></tr><tr><td class="links"><b>Cyclodieen:</b></td><td class="rechts"><a href="/wiki/Cyclobutadieen" title="Cyclobutadieen">Cyclobutadieen</a> · <a href="/wiki/Cyclopentadieen" title="Cyclopentadieen">Cyclopentadieen</a> · <a href="/wiki/1,3-cyclohexadieen" title="1,3-cyclohexadieen">1,3-cyclohexadieen</a> · <a href="/wiki/1,4-cyclohexadieen" title="1,4-cyclohexadieen">1,4-cyclohexadieen</a> · <a href="/wiki/1,3-cycloheptadieen" title="1,3-cycloheptadieen">1,3-cycloheptadieen</a> · <a href="/wiki/1,4-cycloheptadieen" title="1,4-cycloheptadieen">1,4-cycloheptadieen</a> · <a href="/wiki/1,3-cyclo-octadieen" title="1,3-cyclo-octadieen">1,3-cyclo-octadieen</a> · <a href="/wiki/1,4-cyclo-octadieen" title="1,4-cyclo-octadieen">1,4-cyclo-octadieen</a> · <a href="/wiki/1,5-cyclo-octadieen" title="1,5-cyclo-octadieen">1,5-cyclo-octadieen</a></td></tr><tr><td class="links"><b>Cyclotrieen:</b></td><td class="rechts"><a href="/wiki/Benzeen" title="Benzeen">Benzeen</a> · <a href="/wiki/Cycloheptatrieen" title="Cycloheptatrieen">Cycloheptatrieen</a> · <a href="/wiki/1,3,6-cyclo-octatrieen" title="1,3,6-cyclo-octatrieen">1,3,6-cyclo-octatrieen</a> · <a class="mw-selflink selflink">1,5,9-cyclododecatrieen</a></td></tr><tr><td class="links"><b>Cyclopolyeen:</b></td><td class="rechts"><a href="/wiki/Cyclo-octatetraeen" title="Cyclo-octatetraeen">Cyclo-octatetraeen</a> · <a href="/wiki/Cyclononatetraeen" title="Cyclononatetraeen">Cyclononatetraeen</a> · <a href="/wiki/Cyclo-octadecanonaeen" title="Cyclo-octadecanonaeen">Cyclo-octadecanonaeen</a></td></tr></tbody></table> </div></div> <!-- NewPP limit report Parsed by mw‐api‐int.codfw.main‐7f85796d66‐psshj Cached time: 20241127121029 Cache expiry: 2592000 Reduced expiry: false Complications: [] CPU time usage: 0.168 seconds Real time usage: 0.453 seconds Preprocessor visited node count: 2486/1000000 Post‐expand include size: 24046/2097152 bytes Template argument size: 9652/2097152 bytes Highest expansion depth: 12/100 Expensive parser function count: 1/500 Unstrip recursion depth: 0/20 Unstrip post‐expand size: 2896/5000000 bytes Lua time usage: 0.012/10.000 seconds Lua memory usage: 893113/52428800 bytes Number of Wikibase entities loaded: 1/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 197.340 1 -total 68.86% 135.889 1 Sjabloon:Infobox_chemische_stof 66.40% 131.029 1 Sjabloon:Infobox_generiek 22.65% 44.692 3 Sjabloon:Wikidata 15.40% 30.396 1 Sjabloon:Navigatie_cycloalkenen 14.44% 28.501 1 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