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div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Benzene" title="Benzene">Benzene</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <p><b>Cyclohexane</b> is a <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkane</a> with the <a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap"><b>C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub></b></span>. Cyclohexane is <a href="/wiki/Non-polar" class="mw-redirect" title="Non-polar">non-polar</a>. Cyclohexane is a colourless, <a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a> liquid with a distinctive <a href="/wiki/Detergent" title="Detergent">detergent</a>-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexane is mainly used for the industrial production of <a href="/wiki/Adipic_acid" title="Adipic acid">adipic acid</a> and <a href="/wiki/Caprolactam" title="Caprolactam">caprolactam</a>, which are <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursors</a> to <a href="/wiki/Nylon" title="Nylon">nylon</a>.<sup id="cite_ref-Campbell2011_5-0" class="reference"><a href="#cite_note-Campbell2011-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><table class="infobox ib-chembox"> <caption>Cyclohexane </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert" typeof="mw:File"><a href="/wiki/File:Cyclohexane-2D-skeletal.svg" class="mw-file-description" title="Cyclohexane"><img alt="Cyclohexane" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Cyclohexane-2D-skeletal.svg/110px-Cyclohexane-2D-skeletal.svg.png" decoding="async" width="110" height="127" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Cyclohexane-2D-skeletal.svg/165px-Cyclohexane-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/Cyclohexane-2D-skeletal.svg/220px-Cyclohexane-2D-skeletal.svg.png 2x" data-file-width="200" data-file-height="230"></a><figcaption>Cyclohexane</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Cyclohexane_molecule_chair_spacefill.png" class="mw-file-description" title="3D structure of a cyclohexane molecule"><img alt="3D structure of a cyclohexane molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Cyclohexane_molecule_chair_spacefill.png/110px-Cyclohexane_molecule_chair_spacefill.png" decoding="async" width="110" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Cyclohexane_molecule_chair_spacefill.png/165px-Cyclohexane_molecule_chair_spacefill.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Cyclohexane_molecule_chair_spacefill.png/220px-Cyclohexane_molecule_chair_spacefill.png 2x" data-file-width="1877" data-file-height="2000"></a><figcaption>3D structure of a cyclohexane molecule</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert" typeof="mw:File"><a href="/wiki/File:Chair_conformation_of_cyclohexane.svg" class="mw-file-description" title="Skeletal formula of cyclohexane in its chair conformation"><img alt="Skeletal formula of cyclohexane in its chair conformation" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Chair_conformation_of_cyclohexane.svg/110px-Chair_conformation_of_cyclohexane.svg.png" decoding="async" width="110" height="46" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Chair_conformation_of_cyclohexane.svg/165px-Chair_conformation_of_cyclohexane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Chair_conformation_of_cyclohexane.svg/220px-Chair_conformation_of_cyclohexane.svg.png 2x" data-file-width="131" data-file-height="55"></a><figcaption>Skeletal formula of cyclohexane in its chair conformation</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Cyclohexane-chair-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of cyclohexane in its chair conformation"><img alt="Ball-and-stick model of cyclohexane in its chair conformation" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Cyclohexane-chair-3D-balls.png/110px-Cyclohexane-chair-3D-balls.png" decoding="async" width="110" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Cyclohexane-chair-3D-balls.png/165px-Cyclohexane-chair-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Cyclohexane-chair-3D-balls.png/220px-Cyclohexane-chair-3D-balls.png 2x" data-file-width="1100" data-file-height="940"></a><figcaption>Ball-and-stick model of cyclohexane in its chair conformation</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Cyclohexane<sup id="cite_ref-iupac2013_2-0" class="reference"><a href="#cite_note-iupac2013-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Hexanaphthene (archaic)<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></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=110-82-7">110-82-7</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C1CCCCC1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1900225 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=29005">CHEBI:29005</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL15980">ChEMBL15980</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.7787.html">7787</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB03561">DB03561</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.003.461">100.003.461</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q211433#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20"></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>1662 </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C11249">C11249</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/8078">8078</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>GU6300000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/48K5MKG32S">48K5MKG32S</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>1145 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID4021923">DTXSID4021923</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q211433#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20"></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H12/c1-2-4-6-5-3-1/h1-6H2<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XDTMQSROBMDMFD-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C6H12/c1-2-4-6-5-3-1/h1-6H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XDTMQSROBMDMFD-UHFFFAOYAZ</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C1CCCCC1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>6</sub><span title="Hydrogen">H</span><sub>12</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001841620000000000♠"></span>84.162</span> g·mol<sup>−1</sup> </td></tr> <tr> <td>Appearance </td> <td>Colourless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Sweet, <a href="/wiki/Gasoline" title="Gasoline">gasoline</a>-like </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.7739 g/ml (liquid); 0.996 g/ml (solid) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>6.47 °C (43.65 °F; 279.62 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>80.74 °C (177.33 °F; 353.89 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Immiscible </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Soluble in <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Ethanol" title="Ethanol">alcohol</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a> </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>78 mmHg (20 °C)<sup id="cite_ref-PGCH_3-0" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−68.13·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.42662 </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>1.02 <a href="/wiki/Poise_(unit)" title="Poise (unit)">cP</a> at 17 °C </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512"></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724"></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512"></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724"></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H225: Highly flammable liquid and vapour">H225</abbr>, <abbr class="abbr" title="H304: May be fatal if swallowed and enters airways">H304</abbr>, <abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H336: May cause drowsiness or dizziness">H336</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P242: Use only non-sparking tools.">P242</abbr>, <abbr class="abbr" title="P243: Take precautionary measures to prevent static discharges.">P243</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.">P301+P310</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P331: Do NOT induce vomiting.">P331</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P391: Collect spillage.">P391</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P403+P235: Store in a well ventilated place. Keep cool.">P403+P235</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_dc8789d9d8c839e4"></span><map name="ImageMap_dc8789d9d8c839e4"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine"><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline"><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen"><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code"></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>−20 °C (−4 °F; 253 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br>temperature</a></div> </td> <td>245 °C (473 °F; 518 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>1.3–8%<sup id="cite_ref-PGCH_3-1" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>12705 mg/kg (rat, oral)<br>813 mg/kg (mouse, oral)<sup id="cite_ref-IDLH_4-0" class="reference"><a href="#cite_note-IDLH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LCLo" title="Lethal dose">lowest published</a>)</div> </td> <td>17,142 ppm (mouse, 2 <a href="/wiki/Hour" title="Hour">h</a>)<br>26,600 ppm (rabbit, 1 h)<sup id="cite_ref-IDLH_4-1" class="reference"><a href="#cite_note-IDLH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 300 ppm (1050 mg/m<sup>3</sup>)<sup id="cite_ref-PGCH_3-2" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>TWA 300 ppm (1050 mg/m<sup>3</sup>)<sup id="cite_ref-PGCH_3-3" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>1300 ppm<sup id="cite_ref-PGCH_3-4" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br>formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−156 kJ/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br>combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−3920 kJ/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkanes</a></div> </td> <td><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a><br><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a><br><a href="/wiki/Benzene" title="Benzene">Benzene</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Cyclohexane_(data_page)" title="Cyclohexane (data page)">Cyclohexane (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464366627&page2=Cyclohexane">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600"></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table> <p><b>Cyclohexyl</b> (<b><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">11</sub></span></b>) is the <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> <a href="/wiki/Substituent" title="Substituent">substituent</a> of cyclohexane and is abbreviated <b>Cy</b>.<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> </p> <div id="toc" class="toc" role="navigation" aria-labelledby="mw-toc-heading"><input type="checkbox" role="button" id="toctogglecheckbox" class="toctogglecheckbox" style="display:none"><div class="toctitle" lang="en" dir="ltr"><h2 id="mw-toc-heading">Contents</h2><span class="toctogglespan"><label class="toctogglelabel" for="toctogglecheckbox"></label></span></div> <ul> <li class="toclevel-1 tocsection-1"><a href="#Production"><span class="tocnumber">1</span> <span class="toctext">Production</span></a> <ul> <li class="toclevel-2 tocsection-2"><a href="#Modern_industrial_synthesis"><span class="tocnumber">1.1</span> <span class="toctext">Modern industrial synthesis</span></a></li> <li class="toclevel-2 tocsection-3"><a href="#History_of_synthesis"><span class="tocnumber">1.2</span> <span class="toctext">History of synthesis</span></a> <ul> <li class="toclevel-3 tocsection-4"><a href="#Failure"><span class="tocnumber">1.2.1</span> <span class="toctext">Failure</span></a></li> <li class="toclevel-3 tocsection-5"><a href="#Success"><span class="tocnumber">1.2.2</span> <span class="toctext">Success</span></a></li> </ul> </li> </ul> </li> <li class="toclevel-1 tocsection-6"><a href="#Reactions_and_uses"><span class="tocnumber">2</span> <span class="toctext">Reactions and uses</span></a></li> <li class="toclevel-1 tocsection-7"><a href="#Conformation"><span class="tocnumber">3</span> <span class="toctext">Conformation</span></a> <ul> <li class="toclevel-2 tocsection-8"><a href="#Solid_phases"><span class="tocnumber">3.1</span> <span class="toctext">Solid phases</span></a></li> </ul> </li> <li class="toclevel-1 tocsection-9"><a href="#See_also"><span class="tocnumber">4</span> <span class="toctext">See also</span></a></li> <li class="toclevel-1 tocsection-10"><a href="#References"><span class="tocnumber">5</span> <span class="toctext">References</span></a></li> <li class="toclevel-1 tocsection-11"><a href="#External_links"><span class="tocnumber">6</span> <span class="toctext">External links</span></a></li> </ul> </div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(1)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Production">Production</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=1" title="Edit section: Production" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-1 collapsible-block" id="mf-section-1"> <p>Cyclohexane is one of components of <a href="/wiki/Naphtha" title="Naphtha">naphtha</a>, from which it can be extracted by advanced distillation methods. Distillation is usually combined with <a href="/wiki/Isomerization" title="Isomerization">isomerization</a> of <a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">methylcyclopentane</a>, a similar component extracted from naphtha by similar methods. Together, these processes cover only a minority (15-20%) of the modern industrial demand, and are complemented by synthesis.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Modern_industrial_synthesis">Modern industrial synthesis</h3><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=2" title="Edit section: Modern industrial synthesis" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div> <p>On an industrial scale, cyclohexane is produced by <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of <a href="/wiki/Benzene" title="Benzene">benzene</a> in the presence of a <a href="/wiki/Raney_nickel" title="Raney nickel">Raney nickel</a> catalyst.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (October 2024)">citation needed</span></a></i>]</sup> Producers of cyclohexane account for approximately 11.4% of global demand for benzene.<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> The reaction is highly exothermic, with ΔH(500 K) = -216.37 kJ/mol. Dehydrogenation commenced noticeably above 300 °C, reflecting the favorable entropy for dehydrogenation.<sup id="cite_ref-Ullmann_9-0" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="skin-invert" typeof="mw:File"><a href="/wiki/File:Industrial_synthesis_of_cyclohexane.svg" class="mw-file-description" title="Catalytic hydrogenation of benzene to cyclohexane with a raney-nickel catalyst"><noscript><img alt="Catalytic hydrogenation of benzene to cyclohexane with a raney-nickel catalyst" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Industrial_synthesis_of_cyclohexane.svg/300px-Industrial_synthesis_of_cyclohexane.svg.png" decoding="async" width="300" height="66" class="mw-file-element" data-file-width="496" data-file-height="109"></noscript><span class="lazy-image-placeholder" style="width: 300px;height: 66px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Industrial_synthesis_of_cyclohexane.svg/300px-Industrial_synthesis_of_cyclohexane.svg.png" data-alt="Catalytic hydrogenation of benzene to cyclohexane with a raney-nickel catalyst" data-width="300" data-height="66" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Industrial_synthesis_of_cyclohexane.svg/450px-Industrial_synthesis_of_cyclohexane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Industrial_synthesis_of_cyclohexane.svg/600px-Industrial_synthesis_of_cyclohexane.svg.png 2x" data-class="mw-file-element"> </span></a></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="History_of_synthesis">History of synthesis</h3><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=3" title="Edit section: History of synthesis" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div> <p>Unlike <a href="/wiki/Benzene" title="Benzene">benzene</a>, cyclohexane is not found in natural resources such as coal. For this reason, early investigators synthesized their cyclohexane samples.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Failure">Failure</h4><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=4" title="Edit section: Failure" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div> <ul><li>In 1867 <a href="/wiki/Marcellin_Berthelot" title="Marcellin Berthelot">Marcellin Berthelot</a> <a href="/wiki/Organic_reduction" class="mw-redirect" title="Organic reduction">reduced</a> <a href="/wiki/Benzene" title="Benzene">benzene</a> with <a href="/wiki/Hydroiodic_acid" title="Hydroiodic acid">hydroiodic acid</a> at elevated temperatures.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li> <li>In 1870, <a href="/wiki/Adolf_von_Baeyer" title="Adolf von Baeyer">Adolf von Baeyer</a> repeated the reaction<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> and pronounced the same reaction product "hexahydrobenzene".</li> <li>In 1890 <a href="/wiki/Vladimir_Markovnikov" title="Vladimir Markovnikov">Vladimir Markovnikov</a> believed he was able to distill the same compound from Caucasus <a href="/wiki/Petroleum" title="Petroleum">petroleum</a>, calling his concoction "hexanaphtene".<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (May 2023)">citation needed</span></a></i>]</sup></li></ul> <p>Surprisingly, their cyclohexanes boiled higher by 10 °C than either hexahydrobenzene or hexanaphthene, but this riddle was solved in 1895 by Markovnikov, <a href="/wiki/Nikolai_Kischner" title="Nikolai Kischner">N.M. Kishner</a>, and <a href="/wiki/Nikolay_Zelinsky" title="Nikolay Zelinsky">Nikolay Zelinsky</a> when they reassigned "hexahydrobenzene" and "hexanaphtene" as <a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">methylcyclopentane</a>, the result of an unexpected <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearrangement reaction</a>. </p> <dl><dd><span class="skin-invert" typeof="mw:File"><a href="/wiki/File:CyclohexaneBerthelot.svg" class="mw-file-description" title="reduction of benzene to methylcyclopentane"><noscript><img alt="reduction of benzene to methylcyclopentane" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/CyclohexaneBerthelot.svg/180px-CyclohexaneBerthelot.svg.png" decoding="async" width="180" height="62" class="mw-file-element" data-file-width="512" data-file-height="176"></noscript><span class="lazy-image-placeholder" style="width: 180px;height: 62px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/CyclohexaneBerthelot.svg/180px-CyclohexaneBerthelot.svg.png" data-alt="reduction of benzene to methylcyclopentane" data-width="180" data-height="62" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/CyclohexaneBerthelot.svg/270px-CyclohexaneBerthelot.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/CyclohexaneBerthelot.svg/360px-CyclohexaneBerthelot.svg.png 2x" data-class="mw-file-element"> </span></a></span></dd></dl> <div class="mw-heading mw-heading4"><h4 id="Success">Success</h4><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=5" title="Edit section: Success" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div> <p>In 1894, Baeyer synthesized cyclohexane starting with a <a href="/wiki/Ketonic_decarboxylation" title="Ketonic decarboxylation">ketonic decarboxylation</a> of <a href="/wiki/Pimelic_acid" title="Pimelic acid">pimelic acid</a> followed by multiple reductions: </p> <dl><dd><span class="skin-invert" typeof="mw:File"><a href="/wiki/File:Cyclohexane_Synthesis.svg" class="mw-file-description" title="1894 cyclohexane synthesis Baeyer"><noscript><img alt="1894 cyclohexane synthesis Baeyer" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Cyclohexane_Synthesis.svg/550px-Cyclohexane_Synthesis.svg.png" decoding="async" width="550" height="79" class="mw-file-element" data-file-width="512" data-file-height="74"></noscript><span class="lazy-image-placeholder" style="width: 550px;height: 79px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Cyclohexane_Synthesis.svg/550px-Cyclohexane_Synthesis.svg.png" data-alt="1894 cyclohexane synthesis Baeyer" data-width="550" data-height="79" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Cyclohexane_Synthesis.svg/825px-Cyclohexane_Synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Cyclohexane_Synthesis.svg/1100px-Cyclohexane_Synthesis.svg.png 2x" data-class="mw-file-element"> </span></a></span></dd></dl> <p>In the same year, E. Haworth and W.H. Perkin Jr. (1860–1929) prepared it via a <a href="/wiki/Wurtz_reaction" title="Wurtz reaction">Wurtz reaction</a> of 1,6-dibromohexane. </p> <dl><dd><span class="skin-invert" typeof="mw:File"><a href="/wiki/File:Cyclohexane_Synthesis_Perkin.svg" class="mw-file-description" title="1894 cyclohexane synthesis Perkin / haworth"><noscript><img alt="1894 cyclohexane synthesis Perkin / haworth" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Cyclohexane_Synthesis_Perkin.svg/300px-Cyclohexane_Synthesis_Perkin.svg.png" decoding="async" width="300" height="51" class="mw-file-element" data-file-width="512" data-file-height="87"></noscript><span class="lazy-image-placeholder" style="width: 300px;height: 51px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Cyclohexane_Synthesis_Perkin.svg/300px-Cyclohexane_Synthesis_Perkin.svg.png" data-alt="1894 cyclohexane synthesis Perkin / haworth" data-width="300" data-height="51" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Cyclohexane_Synthesis_Perkin.svg/450px-Cyclohexane_Synthesis_Perkin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/Cyclohexane_Synthesis_Perkin.svg/600px-Cyclohexane_Synthesis_Perkin.svg.png 2x" data-class="mw-file-element"> </span></a></span></dd></dl> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(2)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Reactions_and_uses">Reactions and uses</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=6" title="Edit section: Reactions and uses" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-2 collapsible-block" id="mf-section-2"> <p>Although rather unreactive, cyclohexane undergoes <a href="/wiki/Autoxidation" title="Autoxidation">autoxidation</a> to give a mixture of <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a> and <a href="/wiki/Cyclohexanol" title="Cyclohexanol">cyclohexanol</a>. The cyclohexanone–cyclohexanol mixture, called "<i>KA oil</i>", is a raw material for <a href="/wiki/Adipic_acid" title="Adipic acid">adipic acid</a> and <a href="/wiki/Caprolactam" title="Caprolactam">caprolactam</a>, precursors to <a href="/wiki/Nylon" title="Nylon">nylon</a>. Several million kilograms of cyclohexanone and cyclohexanol are produced annually.<sup id="cite_ref-Ullmann_9-1" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>It is used as a solvent in some brands of correction fluid. Cyclohexane is sometimes used as a non-polar organic solvent, although <a href="/wiki/N-hexane" class="mw-redirect" title="N-hexane">n-hexane</a> is more widely used for this purpose. It is frequently used as a <a href="/wiki/Recrystallization_(chemistry)" title="Recrystallization (chemistry)">recrystallization</a> solvent, as many organic compounds exhibit good solubility in hot cyclohexane and poor solubility at low temperatures. </p><p>Cyclohexane is also used for calibration of <a href="/wiki/Differential_scanning_calorimetry" title="Differential scanning calorimetry">differential scanning calorimetry</a> (DSC) instruments, because of a convenient crystal-crystal transition at −87.1 °C.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Cyclohexane vapour is used in vacuum carburizing furnaces, in heat treating equipment manufacture. </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(3)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Conformation">Conformation</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=7" title="Edit section: Conformation" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-3 collapsible-block" id="mf-section-3"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cyclohexane_conformation" title="Cyclohexane conformation">Cyclohexane conformation</a></div> <p>The 6-vertex edge ring does not conform to the shape of a perfect <a href="/wiki/Hexagon" title="Hexagon">hexagon</a>. The conformation of a flat 2D planar hexagon has considerable strain because the C-H bonds would be <a href="/wiki/Eclipsed_conformation" title="Eclipsed conformation">eclipsed</a>. Therefore, to reduce <a href="/wiki/Strain_(chemistry)#Torsional_strain" title="Strain (chemistry)">torsional strain</a>, cyclohexane adopts a three-dimensional structure known as the <a href="/wiki/Chair_conformation" class="mw-redirect" title="Chair conformation">chair conformation</a>, which rapidly interconvert at room temperature via a process known as a <a href="/wiki/Ring_flip" title="Ring flip">chair flip</a>. During the chair flip, there are three other intermediate conformations that are encountered: the half-chair, which is the most unstable conformation, the more stable boat conformation, and the twist-boat, which is more stable than the boat but still much less stable than the chair. The chair and twist-boat are energy minima and are therefore conformers, while the half-chair and the boat are transition states and represent energy maxima. The idea that the chair conformation is the most stable structure for cyclohexane was first proposed as early as 1890 by Hermann Sachse, but only gained widespread acceptance much later. The new conformation puts the carbons at an angle of 109.5°. Half of the hydrogens are in the plane of the ring (<i>equatorial</i>) while the other half are perpendicular to the plane (<i>axial</i>). This conformation allows for the most stable structure of cyclohexane. Another conformation of cyclohexane exists, known as <a href="/wiki/Boat_conformation" class="mw-redirect" title="Boat conformation">boat conformation</a>, but it interconverts to the slightly more stable chair formation. If cyclohexane is mono-substituted with a large <a href="/wiki/Substituent" title="Substituent">substituent</a>, then the substituent will most likely be found attached in an equatorial position, as this is the slightly more stable <a href="/wiki/Chemical_structure" title="Chemical structure">conformation</a>. </p><p>Cyclohexane has the lowest angle and torsional strain of all the cycloalkanes; as a result cyclohexane has been deemed a 0 in total ring strain. </p> <div class="mw-heading mw-heading3"><h3 id="Solid_phases">Solid phases</h3><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=8" title="Edit section: Solid phases" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div> <p>Cyclohexane has two crystalline phases. The high-temperature phase I, stable between 186 K and the melting point 280 K, is a <a href="/wiki/Plastic_crystal" title="Plastic crystal">plastic crystal</a>, which means the molecules retain some rotational degree of freedom. The low-temperature (below 186 K) phase II is ordered. Two other low-temperature (metastable) phases III and IV have been obtained by application of moderate pressures above 30 MPa, where phase IV appears exclusively in <a href="/wiki/Deuterated" class="mw-redirect" title="Deuterated">deuterated</a> cyclohexane (application of pressure increases the values of all transition temperatures).<sup id="cite_ref-phase_15-0" class="reference"><a href="#cite_note-phase-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable" style="text-align:center"> <caption>Cyclohexane phases<sup id="cite_ref-phase_15-1" class="reference"><a href="#cite_note-phase-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>No</th> <th>Symmetry</th> <th><a href="/wiki/Space_group" title="Space group">Space group</a></th> <th>a (Å)</th> <th>b (Å)</th> <th>c (Å)</th> <th>Z</th> <th>T (K)</th> <th>P (MPa) </th></tr> <tr> <td>I</td> <td>Cubic</td> <td>Fm3m</td> <td>8.61</td> <td></td> <td></td> <td>4</td> <td>195</td> <td>0.1 </td></tr> <tr> <td>II</td> <td><a href="/wiki/Monoclinic" class="mw-redirect" title="Monoclinic">Monoclinic</a></td> <td>C2/c</td> <td>11.23</td> <td>6.44</td> <td>8.20</td> <td>4</td> <td>115</td> <td>0.1 </td></tr> <tr> <td>III</td> <td><a href="/wiki/Orthorhombic" class="mw-redirect" title="Orthorhombic">Orthorhombic</a></td> <td>Pmnn</td> <td>6.54</td> <td>7.95</td> <td>5.29</td> <td>2</td> <td>235</td> <td>30 </td></tr> <tr> <td>IV</td> <td>Monoclinic</td> <td>P12(1)/n1</td> <td>6.50</td> <td>7.64</td> <td>5.51</td> <td>4</td> <td>160</td> <td>37 </td></tr></tbody></table> <p>Here Z is the number structure units per <a href="/wiki/Unit_cell" title="Unit cell">unit cell</a>; the unit cell constants a, b and c were measured at the given temperature T and pressure P. </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(4)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="See_also">See also</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=9" title="Edit section: See also" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-4 collapsible-block" id="mf-section-4"> <ul><li><a href="/wiki/Flixborough_disaster" title="Flixborough disaster">The Flixborough disaster</a>, a major industrial accident caused by an explosion of cyclohexane</li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a></li> <li><a href="/wiki/Ring_flip" title="Ring flip">Ring flip</a></li> <li><a href="/wiki/Cyclohexane_(data_page)" title="Cyclohexane (data page)">Cyclohexane (data page)</a></li></ul> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(5)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="References">References</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=10" title="Edit section: References" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-5 collapsible-block" id="mf-section-5"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20180212201838/http://www.dictionary.com/browse/hexanaphthene">"Hexanaphthene"</a>. <i>dictionary.com</i>. Archived from <a rel="nofollow" class="external text" href="http://www.dictionary.com/browse/hexanaphthene">the original</a> on 2018-02-12.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=dictionary.com&rft.atitle=Hexanaphthene&rft_id=http%3A%2F%2Fwww.dictionary.com%2Fbrowse%2Fhexanaphthene&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclohexane" class="Z3988"></span></span> </li> <li id="cite_note-iupac2013-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1">"Front Matter". <i>Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. 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John Wiley & Sons. p. 345. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-61459-2" title="Special:BookSources/978-3-527-61459-2"><bdi>978-3-527-61459-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Industrial+Organic+Chemistry&rft.pages=345&rft.pub=John+Wiley+%26+Sons&rft.date=2008-07-11&rft.isbn=978-3-527-61459-2&rft.aulast=Weissermel&rft.aufirst=Klaus&rft.au=Arpe%2C+Hans-J%C3%BCrgen&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DAO5HyPl_X0wC%26pg%3DPA345&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclohexane" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCeresana" class="citation web cs1">Ceresana. <a rel="nofollow" class="external text" href="http://www.ceresana.com/en/market-studies/chemicals/benzene/">"Benzene - Study: Market, Analysis, Trends 2021 - Ceresana"</a>. <i>www.ceresana.com</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20171221002731/http://www.ceresana.com/en/market-studies/chemicals/benzene/">Archived</a> from the original on 21 December 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">4 May</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.ceresana.com&rft.atitle=Benzene+-+Study%3A+Market%2C+Analysis%2C+Trends+2021+-+Ceresana&rft.au=Ceresana&rft_id=http%3A%2F%2Fwww.ceresana.com%2Fen%2Fmarket-studies%2Fchemicals%2Fbenzene%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclohexane" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_9-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMichael_Tuttle_Musser2005" class="citation encyclopaedia cs1">Michael Tuttle Musser (2005). "Cyclohexanol and Cyclohexanone". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. 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href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBertholet1867" class="citation journal cs1 cs1-prop-long-vol cs1-prop-foreign-lang-source">Bertholet (1867). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=YVgSAAAAYAAJ&pg=PA53">"Nouvelles applications des méthodes de réduction en chimie organique"</a> [New applications of reduction methods in organic chemistry]. <i>Bulletin de la Société Chimique de Paris</i> (in French). series 2 (7): <span class="nowrap">53–</span>65.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bulletin+de+la+Soci%C3%A9t%C3%A9+Chimique+de+Paris&rft.atitle=Nouvelles+applications+des+m%C3%A9thodes+de+r%C3%A9duction+en+chimie+organique&rft.volume=series+2&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E53-%3C%2Fspan%3E65&rft.date=1867&rft.au=Bertholet&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DYVgSAAAAYAAJ%26pg%3DPA53&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclohexane" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBertholet1868" class="citation journal cs1 cs1-prop-long-vol cs1-prop-foreign-lang-source">Bertholet (1868). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=r1sSAAAAYAAJ&q=Bertholet&pg=PA17">"Méthode universelle pour réduire et saturer d'hydrogène les composés organiques"</a> [Universal method for reducing and saturating organic compounds with hydrogen]. <i>Bulletin de la Société Chimique de Paris</i> (in French). series 2 (9): <span class="nowrap">8–</span>31. <q>En effet, la benzine, chauffée à 280° pendant 24 heures avec 80 fois son poids d'une solution aqueuse saturée à froid d'acide iodhydrique, se change à peu près entièrement en hydrure d'hexylène, C<sub>12</sub>H<sub>14</sub>, en fixant 4 fois son volume d'hydrogène: C<sub>12</sub>H<sub>6</sub> + 4H<sub>2</sub> = C<sub>12</sub>H<sub>14</sub> … Le nouveau carbure formé par la benzine est un corps unique et défini: il bout à 69°, et offre toutes les propriétés et la composition de l'hydrure d'hexylène extrait des pétroles.</q> [In effect, benzene, heated to 280° for 24 hours with 80 times its weight of an aqueous solution of cold saturated hydroiodic acid, is changed almost entirely into hydride of hexylene, C<sub>12</sub>H<sub>14</sub>, [Note: this formula for hexane (C<sub>6</sub>H<sub>14</sub>) is wrong because chemists at that time used the incorrect atomic mass for carbon.] by fixing [i.e., combining with] 4 times its volume of hydrogen: C<sub>12</sub>H<sub>6</sub> + 4H<sub>2</sub> = C<sub>12</sub>H<sub>14</sub> The new carbon compound formed by benzene is a unique and well-defined substance: it boils at 69° and presents all the properties and the composition of hydride of hexylene extracted from oil.)]</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bulletin+de+la+Soci%C3%A9t%C3%A9+Chimique+de+Paris&rft.atitle=M%C3%A9thode+universelle+pour+r%C3%A9duire+et+saturer+d%27hydrog%C3%A8ne+les+compos%C3%A9s+organiques&rft.volume=series+2&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E8-%3C%2Fspan%3E31&rft.date=1868&rft.au=Bertholet&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dr1sSAAAAYAAJ%26q%3DBertholet%26pg%3DPA17&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclohexane" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAdolf_Baeyer1870" class="citation journal cs1">Adolf Baeyer (1870). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=RJU8AAAAIAAJ&pg=PA266">"Ueber die Reduction aromatischer Kohlenwasserstoffe durch Jodphosphonium"</a> [On the reduction of aromatic compound by phosphonium iodide [H<sub>4</sub>IP]]. <i>Annalen der Chemie und Pharmacie</i>. <b>55</b>: <span class="nowrap">266–</span>281. <q>Bei der Reduction mit Natriumamalgam oder Jodphosphonium addiren sich im höchsten Falle sechs Atome Wasserstoff, und es entstehen Abkömmlinge, die sich von einem Kohlenwasserstoff C<sub>6</sub>H<sub>12</sub> ableiten. Dieser Kohlenwasserstoff ist aller Wahrscheinlichkeit nach ein geschlossener Ring, da seine Derivate, das Hexahydromesitylen und Hexahydromellithsäure, mit Leichtigkeit wieder in Benzolabkömmlinge übergeführt werden können.</q> [During the reduction [of benzene] with sodium amalgam or phosphonium iodide, six atoms of hydrogen are added in the extreme case, and there arise derivatives, which derive from a hydrocarbon C<sub>6</sub>H<sub>12</sub>. This hydrocarbon is in all probability a closed ring, since its derivatives — hexahydromesitylene [1,3,5 - trimethyl cyclohexane] and hexahydromellithic acid [cyclohexane-1,2,3,4,5,6-hexacarboxylic acid] — can be converted with ease again into benzene derivatives.]</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Chemie+und+Pharmacie&rft.atitle=Ueber+die+Reduction+aromatischer+Kohlenwasserstoffe+durch+Jodphosphonium&rft.volume=55&rft.pages=%3Cspan+class%3D%22nowrap%22%3E266-%3C%2Fspan%3E281&rft.date=1870&rft.au=Adolf+Baeyer&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DRJU8AAAAIAAJ%26pg%3DPA266&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclohexane" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPrice1995" class="citation journal cs1">Price, D. M. (1995). "Temperature Calibration of Differential Scanning Calorimeters". <i>Journal of Thermal Analysis</i>. <b>45</b> (6): <span class="nowrap">1285–</span>1296. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF02547423">10.1007/BF02547423</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:97402835">97402835</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Thermal+Analysis&rft.atitle=Temperature+Calibration+of+Differential+Scanning+Calorimeters&rft.volume=45&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1285-%3C%2Fspan%3E1296&rft.date=1995&rft_id=info%3Adoi%2F10.1007%2FBF02547423&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A97402835%23id-name%3DS2CID&rft.aulast=Price&rft.aufirst=D.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclohexane" class="Z3988"></span></span> </li> <li id="cite_note-phase-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-phase_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-phase_15-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMayerUrbanHabryloHolderna1991" class="citation journal cs1">Mayer, J.; Urban, S.; Habrylo, S.; Holderna, K.; Natkaniec, I.; Würflinger, A.; Zajac, W. (1991). "Neutron Scattering Studies of C6H12 and C6D12 Cyclohexane under High Pressure". <i>Physica Status Solidi B</i>. <b>166</b> (2): 381. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1991PSSBR.166..381M">1991PSSBR.166..381M</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fpssb.2221660207">10.1002/pssb.2221660207</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Physica+Status+Solidi+B&rft.atitle=Neutron+Scattering+Studies+of+C6H12+and+C6D12+Cyclohexane+under+High+Pressure&rft.volume=166&rft.issue=2&rft.pages=381&rft.date=1991&rft_id=info%3Adoi%2F10.1002%2Fpssb.2221660207&rft_id=info%3Abibcode%2F1991PSSBR.166..381M&rft.aulast=Mayer&rft.aufirst=J.&rft.au=Urban%2C+S.&rft.au=Habrylo%2C+S.&rft.au=Holderna%2C+K.&rft.au=Natkaniec%2C+I.&rft.au=W%C3%BCrflinger%2C+A.&rft.au=Zajac%2C+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclohexane" class="Z3988"></span></span> </li> </ol></div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(6)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="External_links">External links</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cyclohexane&action=edit&section=11" title="Edit section: External links" class="cdx-button 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.side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><noscript><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" data-file-width="1024" data-file-height="1376"></noscript><span class="lazy-image-placeholder" style="width: 30px;height: 40px;" data-src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" data-alt="" data-width="30" data-height="40" data-srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-class="mw-file-element"> </span></a></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Cyclohexane" class="extiw" title="commons:Category:Cyclohexane">Cyclohexane</a></span>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0242.htm">International Chemical Safety Card 0242</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060819025512/http://npi.gov.au/database/substance-info/profiles/30.html">National Pollutant Inventory – Cyclohexane fact sheet</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0163.html">NIOSH Pocket Guide to Chemical Hazards</a></li> <li><a rel="nofollow" class="external text" href="http://www.3dchem.com/molecules.asp?ID=176">Cyclohexane@3Dchem</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20100707214900/http://www.chem.yale.edu/~chem125/125/history/Baeyer/Sachse.html">Hermann Sachse</a> and the first suggestion of a chair conformation.</li> <li><a rel="nofollow" class="external text" href="http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@na+Cyclohexane">NLM Hazardous Substances Databank – Cyclohexane</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060409110115/http://www.labnews.co.uk/new_labnews/article.php?artid=1017&categoryid=2&scheme=2">Methanol Discovered in Space</a></li> <li>Calculation of <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?component=Cyclohexane">vapor pressure</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105CalculationCGI.exe?component=Cyclohexane">liquid density</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/VogelCalculation/VogelCalculationCGI.exe?component=Cyclohexane">dynamic liquid viscosity</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/DIPPR106SFTCalculation/DIPPR106SFTCalculationCGI.exe?component=Cyclohexane">surface tension</a> of cyclohexane</li> <li><a rel="nofollow" class="external text" href="http://processflowsheet.com/cyclohexane-production-by-benzene-hydrogenation/">Cyclohexane production process flowsheet, benzene hydrogenation technique</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist 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data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D1%85%D0%B5%D0%BA%D1%81%D0%B0%D0%BD" title="Циклохексан – Bulgarian" lang="bg" hreflang="bg" data-title="Циклохексан" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Ciclohex%C3%A0" title="Ciclohexà – Catalan" lang="ca" hreflang="ca" data-title="Ciclohexà" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Cyklohexan" title="Cyklohexan – Czech" lang="cs" hreflang="cs" data-title="Cyklohexan" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da badge-Q17559452 badge-recommendedarticle mw-list-item" title="recommended article"><a href="https://da.wikipedia.org/wiki/Cyklohexan" title="Cyklohexan – Danish" lang="da" hreflang="da" data-title="Cyklohexan" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Cyclohexan" title="Cyclohexan – German" lang="de" hreflang="de" data-title="Cyclohexan" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Ts%C3%BCkloheksaan" title="Tsükloheksaan – Estonian" lang="et" hreflang="et" data-title="Tsükloheksaan" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CF%85%CE%BA%CE%BB%CE%BF%CE%B5%CE%BE%CE%AC%CE%BD%CE%B9%CE%BF" title="Κυκλοεξάνιο – Greek" lang="el" hreflang="el" data-title="Κυκλοεξάνιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Ciclohexano" title="Ciclohexano – Spanish" lang="es" hreflang="es" data-title="Ciclohexano" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Cikloheksano" title="Cikloheksano – Esperanto" lang="eo" hreflang="eo" data-title="Cikloheksano" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Ziklohexano" title="Ziklohexano – Basque" lang="eu" hreflang="eu" data-title="Ziklohexano" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%DA%A9%D9%84%D9%88%D9%87%DA%AF%D8%B2%D8%A7%D9%86" title="سیکلوهگزان – Persian" lang="fa" hreflang="fa" data-title="سیکلوهگزان" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Cyclohexane" title="Cyclohexane – French" lang="fr" hreflang="fr" data-title="Cyclohexane" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Ciclohexano" title="Ciclohexano – Galician" lang="gl" hreflang="gl" data-title="Ciclohexano" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%82%AC%EC%9D%B4%ED%81%B4%EB%A1%9C%ED%97%A5%EC%84%B8%EC%9D%B8" title="사이클로헥세인 – Korean" lang="ko" hreflang="ko" data-title="사이클로헥세인" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%91%D5%AB%D5%AF%D5%AC%D5%B8%D5%B0%D5%A5%D6%84%D5%BD%D5%A1%D5%B6" title="Ցիկլոհեքսան – Armenian" lang="hy" hreflang="hy" data-title="Ցիկլոհեքսան" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B8%E0%A4%BE%E0%A4%87%E0%A4%95%E0%A5%8D%E0%A4%B2%E0%A5%8B-%E0%A4%B9%E0%A5%87%E0%A4%95%E0%A5%8D%E0%A4%B8%E0%A5%87%E0%A4%A8" title="साइक्लो-हेक्सेन – Hindi" lang="hi" hreflang="hi" data-title="साइक्लो-हेक्सेन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Sikloheksana" title="Sikloheksana – Indonesian" lang="id" hreflang="id" data-title="Sikloheksana" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Cicloesano" title="Cicloesano – Italian" lang="it" hreflang="it" data-title="Cicloesano" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A6%D7%99%D7%A7%D7%9C%D7%95%D7%94%D7%A7%D7%A1%D7%90%D7%9F" title="ציקלוהקסאן – Hebrew" lang="he" hreflang="he" data-title="ציקלוהקסאן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%AA%E1%83%98%E1%83%99%E1%83%9A%E1%83%9D%E1%83%B0%E1%83%94%E1%83%A5%E1%83%A1%E1%83%90%E1%83%9C%E1%83%98" title="ციკლოჰექსანი – Georgian" lang="ka" hreflang="ka" data-title="ციკლოჰექსანი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B3%D0%B5%D0%BA%D1%81%D0%B0%D0%BD" title="Циклогексан – Kyrgyz" lang="ky" hreflang="ky" data-title="Циклогексан" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Cikloheks%C4%81ns" title="Cikloheksāns – Latvian" lang="lv" hreflang="lv" data-title="Cikloheksāns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Ciklohex%C3%A1n" title="Ciklohexán – Hungarian" lang="hu" hreflang="hu" data-title="Ciklohexán" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D1%85%D0%B5%D0%BA%D1%81%D0%B0%D0%BD" title="Циклохексан – Macedonian" lang="mk" hreflang="mk" data-title="Циклохексан" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Sikloheksana" title="Sikloheksana – Malay" lang="ms" hreflang="ms" data-title="Sikloheksana" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyclohexaan" title="Cyclohexaan – Dutch" lang="nl" hreflang="nl" data-title="Cyclohexaan" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B7%E3%82%AF%E3%83%AD%E3%83%98%E3%82%AD%E3%82%B5%E3%83%B3" title="シクロヘキサン – Japanese" lang="ja" hreflang="ja" data-title="シクロヘキサン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Sykloheksan" title="Sykloheksan – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Sykloheksan" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Sykloheksan" title="Sykloheksan – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Sykloheksan" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cykloheksan" title="Cykloheksan – Polish" lang="pl" hreflang="pl" data-title="Cykloheksan" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Cicloexano" title="Cicloexano – Portuguese" lang="pt" hreflang="pt" data-title="Cicloexano" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Ciclohexan" title="Ciclohexan – Romanian" lang="ro" hreflang="ro" data-title="Ciclohexan" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B3%D0%B5%D0%BA%D1%81%D0%B0%D0%BD" title="Циклогексан – Russian" lang="ru" hreflang="ru" data-title="Циклогексан" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Cyclohexane" title="Cyclohexane – Simple English" lang="en-simple" hreflang="en-simple" data-title="Cyclohexane" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Cyklohex%C3%A1n" title="Cyklohexán – Slovak" lang="sk" hreflang="sk" data-title="Cyklohexán" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Cikloheksan" title="Cikloheksan – Slovenian" lang="sl" hreflang="sl" data-title="Cikloheksan" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cikloheksan" title="Cikloheksan – Serbian" lang="sr" hreflang="sr" data-title="Cikloheksan" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Cikloheksan" title="Cikloheksan – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cikloheksan" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Sykloheksaani" title="Sykloheksaani – Finnish" lang="fi" hreflang="fi" data-title="Sykloheksaani" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Cyklohexan" title="Cyklohexan – Swedish" lang="sv" hreflang="sv" data-title="Cyklohexan" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%B5%E0%AE%B3%E0%AF%88%E0%AE%AF%E0%AE%8E%E0%AE%95%E0%AF%8D%E0%AE%9A%E0%AF%87%E0%AE%A9%E0%AF%8D" title="வளையஎக்சேன் – Tamil" lang="ta" hreflang="ta" data-title="வளையஎக்சேன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Siklohekzan" title="Siklohekzan – Turkish" lang="tr" hreflang="tr" data-title="Siklohekzan" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B3%D0%B5%D0%BA%D1%81%D0%B0%D0%BD" title="Циклогексан – Ukrainian" lang="uk" hreflang="uk" data-title="Циклогексан" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Cyclohexan" title="Cyclohexan – Vietnamese" lang="vi" hreflang="vi" data-title="Cyclohexan" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%92%B0%E5%B7%B1%E7%83%B7" title="環己烷 – Cantonese" lang="yue" hreflang="yue" data-title="環己烷" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%8E%AF%E5%B7%B1%E7%83%B7" title="环己烷 – Chinese" lang="zh" hreflang="zh" data-title="环己烷" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li></ul> </section> </div> <div class="minerva-footer-logo"><img src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" alt="Wikipedia" width="120" height="18" style="width: 7.5em; height: 1.125em;"/> </div> <ul id="footer-info" class="footer-info hlist hlist-separated"> <li id="footer-info-lastmod"> This page was last edited on 4 February 2025, at 15:58<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Content is available under <a class="external" rel="nofollow" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">CC BY-SA 4.0</a> unless otherwise noted.</li> </ul> <ul id="footer-places" class="footer-places hlist hlist-separated"> <li 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