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Revision as of 10:12, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464317679 of page Cyclohexane for the Chem/Drugbox validation project (updated: '').		Latest revision as of 22:59, 16 December 2024 edit Arthurfragoso (talk | contribs)Extended confirmed users2,009 edits Fixes image on dark mode
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			{{Short description|Organic compound; 6-sided hydrocarbon ring}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			{{distinguish|Benzene}}
	{{chembox		{{chembox
			|Watchedfields = changed
	| verifiedrevid = 443679934
			|verifiedrevid = 464366627
	| name=Cyclohexane
	| ImageFileL1 = Cyclohexane-2D-skeletal.svg		|Name=Cyclohexane
			|ImageFileL1 = Cyclohexane-2D-skeletal.svg
			|ImageNameL1 = Cyclohexane
	| ImageSizeL1 = 80px
			|ImageClassL1 = skin-invert
	| ImageNameL1 = Cyclohexane
	| ImageFileR1 = Cyclohexane-3D-space-filling.png		|ImageFileR1 = Cyclohexane molecule chair spacefill.png
			|ImageNameR1 = 3D structure of a cyclohexane molecule
	| ImageSizeR1 = 100px
	| ImageNameR1 = 3D structure of a cyclohexane molecule		|ImageFileL2 = Chair conformation of cyclohexane.svg
			|ImageNameL2 = Skeletal formula of cyclohexane in its chair conformation
	| ImageFileL2 = Cyclohexane-chair-2D-stereo-skeletal.png
			|ImageClassL2 = skin-invert
	| ImageSizeL2 = 100px
			|ImageFileR2 = Cyclohexane-chair-3D-balls.png
	| ImageNameL2 = Skeletal formula of cyclohexane in its chair conformation
			|ImageNameR2 = Ball-and-stick model of cyclohexane in its chair conformation
	| ImageFileR2 = Cyclohexane-chair-3D-balls.png
			|PIN = Cyclohexane<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | pages = P001–P004 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
	| ImageSizeR2 = 100px
			|OtherNames = Hexanaphthene (archaic)<ref>{{cite web|url=http://www.dictionary.com/browse/hexanaphthene|title=Hexanaphthene|archive-url=https://web.archive.org/web/20180212201838/http://www.dictionary.com/browse/hexanaphthene|archive-date=2018-02-12|work=dictionary.com}}</ref>
	| ImageNameR2 = Ball-and-stick model of cyclohexane in its chair conformation
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChEBI_Ref = {{ebicite|correct|EBI}}		|ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 29005		|ChEBI = 29005
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			|SMILES = C1CCCCC1
	| DrugBank = DB03561
			|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| SMILES = C1CCCCC1
			|ChemSpiderID = 7787
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|PubChem = 8078
	| ChemSpiderID = 7787
			|UNII_Ref = {{fdacite|correct|FDA}}
	| PubChem = 8078
			|UNII = 48K5MKG32S
	| UNII_Ref = {{fdacite|correct|FDA}}
			|KEGG_Ref = {{keggcite|correct|kegg}}
	| UNII = 48K5MKG32S
			|KEGG = C11249
	| KEGG_Ref = {{keggcite|correct|kegg}}
			|InChI = 1/C6H12/c1-2-4-6-5-3-1/h1-6H2
	| KEGG = C11249
			|InChIKey = XDTMQSROBMDMFD-UHFFFAOYAZ
	| InChI = 1/C6H12/c1-2-4-6-5-3-1/h1-6H2
			|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| InChIKey = XDTMQSROBMDMFD-UHFFFAOYAZ
			|ChEMBL = 15980
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 15980		|DrugBank = DB03561
			|Gmelin = 1662
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|Beilstein = 1900225
	| StdInChI = 1S/C6H12/c1-2-4-6-5-3-1/h1-6H2
			|3DMet = B04304
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			|RTECS = GU6300000
	| StdInChIKey = XDTMQSROBMDMFD-UHFFFAOYSA-N
			|UNNumber = 1145
	| CASNo_Ref = {{cascite|correct|CAS}}
			|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| CASNo = 110-82-7
			|StdInChI = 1S/C6H12/c1-2-4-6-5-3-1/h1-6H2
	}}
			|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| Section2 = {{Chembox Properties
			|StdInChIKey = XDTMQSROBMDMFD-UHFFFAOYSA-N
	| Formula = C<sub>6</sub>H<sub>12</sub>
			|CASNo_Ref = {{cascite|correct|CAS}}
	| MolarMass = 84.16 g/mol
			|CASNo = 110-82-7
	| Density = 0.779 g/mL, liquid
	| Solubility = Immiscible
	| FreezingPtC = 6.5
	| BoilingPtC = 80.74
	| Viscosity = 1.02 ] at 17 °C
	| RefractIndex = 1.4262
	}}
	| Section4 = {{Chembox Thermochemistry
	| DeltaHf = -156 kJ/mol
	| DeltaHc = -3920 kJ/mol
	| Entropy =
	}}
	| Section7 = {{Chembox Hazards
	| EUClass = Flammable ('''F''')<br />Harmful ('''Xn''')<br />Dangerous for<br />the environment ('''N''')<br />Severe eye irritant, may cause corneal clouding
	| FlashPt = -20 °C
	| NFPA-H = 1
	| NFPA-F = 3
	| NFPA-R =
	| RPhrases = {{R11}}, {{R38}}, {{R65}}, {{R67}}, {{R50/53}}
	| SPhrases = {{S2}}, {{S9}}, {{S16}}, {{S25}}, {{S33}}, {{S60}}, {{S61}}, {{S62}}
	}}
	| Section8 = {{Chembox Related
	| Function = ]s
	| OtherFunctn = ]<br />]
	| OtherCpds = ]<br />]
	}}
	}}		}}
			|Section2={{Chembox Properties
			|C=6|H=12
			|Appearance = Colourless liquid
			|Odor = Sweet, ]-like
			|Density = 0.7739 g/ml (liquid); 0.996 g/ml (solid)
			|Solubility = Immiscible
			|SolubleOther = Soluble in ], ], ]
			|MeltingPtC = 6.47
			|BoilingPtC = 80.74
			|Viscosity = 1.02 ] at 17 °C
			|RefractIndex = 1.42662
			|VaporPressure = 78 mmHg (20 °C)<ref name=PGCH/>
			|MagSus = −68.13·10<sup>−6</sup> cm<sup>3</sup>/mol }}
			|Section4={{Chembox Thermochemistry
			|DeltaHf = −156 kJ/mol
			|DeltaHc = −3920 kJ/mol
			}}
			|Section3={{Chembox Hazards
			|GHSPictograms = {{GHS flame}} {{GHS health hazard}} {{GHS exclamation mark}} {{GHS environment}}
			|GHSSignalWord = Danger
			|HPhrases = {{H-phrases|225|304|315|336}}
			|PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|273|280|301+310|302+352|303+361+353|304+340|312|321|331|332+313|362|370+378|391|403+233|403+235|405|501}}
			|FlashPtC = -20
			|AutoignitionPtC = 245
			|NFPA-H = 1
			|NFPA-F = 3
			|NFPA-R = 0
			|PEL = TWA 300 ppm (1050 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0163}}</ref>
			|ExploLimits = 1.3–8%<ref name=PGCH/>
			|IDLH = 1300 ppm<ref name=PGCH/>
			|REL = TWA 300 ppm (1050 mg/m<sup>3</sup>)<ref name=PGCH/>
			|LD50 = 12705 mg/kg (rat, oral)<br/>813 mg/kg (mouse, oral)<ref name=IDLH>{{IDLH|110827|Cyclohexane}}</ref>
			|LCLo = 17,142 ppm (mouse, 2&nbsp;])<br/>26,600 ppm (rabbit, 1&nbsp;h)<ref name=IDLH/>
			}}
			|Section9={{Chembox Related
			|OtherFunction_label = ]s
			|OtherFunction = ]<br />]
			|OtherCompounds = ]<br />]
			}}
			}}
			'''Cyclohexane''' is a ] with the ] {{chem2|'''C6H12'''}}. Cyclohexane is ]. Cyclohexane is a colourless, ] liquid with a distinctive ]-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexane is mainly used for the industrial production of ] and ], which are ] to ].<ref name="Campbell2011">{{Cite book |last1=Campbell |first1=M. Larry |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2011 |doi=10.1002/14356007.a08_209.pub2 |isbn=978-3527306732 |chapter=Cyclohexane}}</ref>
			'''Cyclohexyl''' ('''{{chem2|C6H11}}''') is the ] ] of cyclohexane and is abbreviated '''Cy'''.<ref>{{cite web |url=http://pubs.acs.org/paragonplus/submission/joceah/joceah_abbreviations.pdf |title=Standard Abbreviations and Acronyms |publisher=The Journal of Organic Chemistry |archive-url=https://web.archive.org/web/20180801004052/http://pubs.acs.org/paragonplus/submission/joceah/joceah_abbreviations.pdf |archive-date=1 Aug 2018}}</ref>
			==Production==
			Cyclohexane is one of components of ], from which it can be extracted by advanced distillation methods. Distillation is usually combined with ] of ], 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.<ref>{{Cite book |last=Weissermel |first=Klaus |url=https://books.google.com/books?id=AO5HyPl_X0wC&pg=PA345 |title=Industrial Organic Chemistry |last2=Arpe |first2=Hans-Jürgen |date=2008-07-11 |publisher=John Wiley & Sons |isbn=978-3-527-61459-2 |pages=345 |language=en}}</ref>
			===Modern industrial synthesis===
			On an industrial scale, cyclohexane is produced by ] of ] in the presence of a ] catalyst.{{Citation needed|date=October 2024}} Producers of cyclohexane account for approximately 11.4% of global demand for benzene.<ref>{{cite web|url=http://www.ceresana.com/en/market-studies/chemicals/benzene/|title=Benzene - Study: Market, Analysis, Trends 2021 - Ceresana|last=Ceresana|website=www.ceresana.com|access-date=4 May 2018|url-status=live|archive-url=https://web.archive.org/web/20171221002731/http://www.ceresana.com/en/market-studies/chemicals/benzene/|archive-date=21 December 2017}}</ref> The reaction is highly exothermic, with ΔH(500 K) = -216.37 kJ/mol. Dehydrogenation commenced noticeably above 300&nbsp;°C, reflecting the favorable entropy for dehydrogenation.<ref name=Ullmann/>
			:]
			===History of synthesis===
			Unlike ], cyclohexane is not found in natural resources such as coal. For this reason, early investigators synthesized their cyclohexane samples.<ref>{{cite journal |title=The Curiously Intertwined Histories of Benzene and Cyclohexane |first=E. W. |last=Warnhoff |journal=] |year=1996 |volume=73 |issue=6 |pages=494 |doi=10.1021/ed073p494 |bibcode=1996JChEd..73..494W}}</ref>
			====Failure====
			* In 1867 ] ] ] with ] at elevated temperatures.<ref>{{cite journal|last=Bertholet|year=1867|url=https://books.google.com/books?id=YVgSAAAAYAAJ&pg=PA53|title=Nouvelles applications des méthodes de réduction en chimie organique|trans-title=New applications of reduction methods in organic chemistry|journal=Bulletin de la Société Chimique de Paris|volume=series 2|issue=7|pages=53–65|language=fr}}</ref><ref>{{cite journal|last=Bertholet|year=1868|title=Méthode universelle pour réduire et saturer d'hydrogène les composés organiques|trans-title=Universal method for reducing and saturating organic compounds with hydrogen|journal=Bulletin de la Société Chimique de Paris|volume=series 2|issue=9|pages=8–31|url=https://books.google.com/books?id=r1sSAAAAYAAJ&q=Bertholet&pg=PA17|quote=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.|trans-quote=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>, by fixing 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.)|language=fr}}</ref>
			* In 1870, ] repeated the reaction<ref>{{cite journal|author=Adolf Baeyer|year=1870|url=https://books.google.com/books?id=RJU8AAAAIAAJ&pg=PA266|title=Ueber die Reduction aromatischer Kohlenwasserstoffe durch Jodphosphonium|trans-title=On the reduction of aromatic compound by phosphonium iodide |journal=Annalen der Chemie und Pharmacie|volume=55|pages=266–281|quote=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.|trans-quote=During the reduction 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 and hexahydromellithic acid — can be converted with ease again into benzene derivatives.}}</ref> and pronounced the same reaction product "hexahydrobenzene".
			* In 1890 ] believed he was able to distill the same compound from Caucasus ], calling his concoction "hexanaphtene".{{citation needed|date=May 2023}}
			Surprisingly, their cyclohexanes boiled higher by 10&nbsp;°C than either hexahydrobenzene or hexanaphthene, but this riddle was solved in 1895 by Markovnikov, ], and ] when they reassigned "hexahydrobenzene" and "hexanaphtene" as ], the result of an unexpected ].
			:]
			====Success====
			In 1894, Baeyer synthesized cyclohexane starting with a ketonization of ] followed by multiple reductions:
			:]
			In the same year, E. Haworth and W.H. Perkin Jr. (1860–1929) prepared it via a ] of 1,6-dibromohexane.
			:]
			==Reactions and uses==
			Although rather unreactive, cyclohexane undergoes ] to give a mixture of ] and ]. The cyclohexanone&ndash;cyclohexanol mixture, called "''KA oil''", is a raw material for ] and ], precursors to ]. Several million kilograms of cyclohexanone and cyclohexanol are produced annually.<ref name=Ullmann>{{cite encyclopedia|author=Michael Tuttle Musser |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|location=Weinheim|year=2005|doi=10.1002/14356007.a08_217|isbn=978-3527306732 |chapter=Cyclohexanol and Cyclohexanone }}</ref>
			It is used as a solvent in some brands of correction fluid. Cyclohexane is sometimes used as a non-polar organic solvent, although ] is more widely used for this purpose. It is frequently used as a ] solvent, as many organic compounds exhibit good solubility in hot cyclohexane and poor solubility at low temperatures.
			Cyclohexane is also used for calibration of ] (DSC) instruments, because of a convenient crystal-crystal transition at −87.1&nbsp;°C.<ref>{{cite journal |first=D. M. |last=Price |title=Temperature Calibration of Differential Scanning Calorimeters |journal=Journal of Thermal Analysis |volume=45 |issue=6 |year=1995 |pages=1285–1296 |doi=10.1007/BF02547423 |s2cid=97402835 }}</ref>
			Cyclohexane vapour is used in vacuum carburizing furnaces, in heat treating equipment manufacture.
			==Conformation==
			{{main|Cyclohexane conformation}}
			The 6-vertex edge ring does not conform to the shape of a perfect ]. The conformation of a flat 2D planar hexagon has considerable strain because the C-H bonds would be ]. Therefore, to reduce ], cyclohexane adopts a three-dimensional structure known as the ], which rapidly interconvert at room temperature via a process known as 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 (''equatorial'') while the other half are perpendicular to the plane (''axial''). This conformation allows for the most stable structure of cyclohexane. Another conformation of cyclohexane exists, known as ], but it interconverts to the slightly more stable chair formation. If cyclohexane is mono-substituted with a large ], then the substituent will most likely be found attached in an equatorial position, as this is the slightly more stable ].
			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.
			===Solid phases===
			Cyclohexane has two crystalline phases. The high-temperature phase I, stable between 186 K and the melting point 280 K, is 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 ] cyclohexane (application of pressure increases the values of all transition temperatures).<ref name=phase>{{cite journal|doi=10.1002/pssb.2221660207|title=Neutron Scattering Studies of C6H12 and C6D12 Cyclohexane under High Pressure|year=1991|last1=Mayer|first1=J.|last2=Urban|first2=S.|last3=Habrylo|first3=S.|last4=Holderna|first4=K.|last5=Natkaniec|first5=I.|last6=Würflinger|first6=A.|last7=Zajac|first7=W.|journal=Physica Status Solidi B|volume=166|issue=2|pages=381|bibcode=1991PSSBR.166..381M}}</ref>
			{|class="wikitable" style="text-align:center"
			|+Cyclohexane phases<ref name=phase/>
			!No!!Symmetry!! ] !! a (Å) !! b (Å) !! c (Å) !! Z !! T (K) !! P (MPa)
			|-
			| I || Cubic || Fm3m || 8.61 || || || 4 || 195 || 0.1
			|-
			| II || ] || C2/c || 11.23 || 6.44 || 8.20 || 4 || 115 || 0.1
			|-
			| III || ] || Pmnn || 6.54 || 7.95 || 5.29 || 2 || 235 || 30
			|-
			| IV || Monoclinic || P12(1)/n1 || 6.50 || 7.64 || 5.51 || 4 || 160 || 37
			|}
			Here Z is the number structure units per ]; the unit cell constants a, b and c were measured at the given temperature T and pressure P.
			==See also==
			* ], a major industrial accident caused by an explosion of cyclohexane
			* ]
			*]
			* ]
			==References==
			<references/>
			==External links==
			{{commons category|Cyclohexane}}
			*
			*
			*
			*
			* and the first suggestion of a chair conformation.
			*
			*
			* Calculation of , , , of cyclohexane
			*
			{{cycloalkanes}}
			{{Authority control}}
			]
			]
			]
			]
			]