| Revision as of 07:22, 19 July 2011 editM97uzivatel (talk | contribs)Extended confirmed users6,631 edits cs:Cyklododekan← Previous edit |
Latest revision as of 09:34, 27 December 2024 edit undoPreimage (talk | contribs)Extended confirmed users1,380 edits →Conformation: Mention chirality |
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{{Use dmy dates|date=September 2021}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 396320292 |
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|ImageFile=Cyclododecane.png |
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| verifiedrevid = 440266645 |
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|ImageSize=180px |
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| ImageFile = Structural formula of cyclododecane.svg |
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|IUPACName=cyclododecane |
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| ImageSize = 150px |
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|OtherNames= |
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| ImageAlt = Structural formula of cyclododecane<!--This is misleading, lowest-energy conformation is "square" --> |
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|Section1= {{Chembox Identifiers |
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| ImageFile1 = Cyclododecane 3D ball.png |
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| InChIKey = DDTBPAQBQHZRDW-UHFFFAOYAN |
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| ImageSize1 = 160 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ImageAlt1 = Ball-and-stick model of the cyclododecane molecule |
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| StdInChIKey = DDTBPAQBQHZRDW-UHFFFAOYSA-N |
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| PIN = Cyclododecane |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8911 |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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| InChI = 1/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 294-62-2 |
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| StdInChI = 1S/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=C1CCCCCCCCCCC1 |
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| UNII = 97CN13ZD83 |
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| MeSHName= |
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| InChIKey = DDTBPAQBQHZRDW-UHFFFAOYAN |
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}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|Section2= {{Chembox Properties |
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| StdInChIKey = DDTBPAQBQHZRDW-UHFFFAOYSA-N |
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| Formula=C<sub>12</sub>H<sub>24</sub> |
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| MolarMass =168.319 |
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| PubChem = 9268 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Appearance=white waxy solid |
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| ChemSpiderID = 8911 |
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| Density= 0.79 g/cm<sup>3</sup> |
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| InChI = 1/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2 |
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| MeltingPt = |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| BoilingPt = |
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| StdInChI = 1S/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2 |
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| SMILES = C1CCCCCCCCCCC1 |
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| ChEMBL = 3185808 |
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| MeSHName = |
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}} |
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|Section3= {{Chembox Hazards |
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| Section2 = {{Chembox Properties |
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| C = 12 | H = 24 |
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| FlashPt=87.6 °C |
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| Appearance = White waxy solid<ref name=":0" /> |
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| Density = 0.855 g/cm<sup>3</sup><ref name="ECHA REACH">ECHA REACH</ref> |
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| MeltingPtC = 60.4 | MeltingPt_ref = <ref name="PubChem" /> |
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| BoilingPtC = 244.0 | BoilingPt_ref = <ref name="ECHA REACH"/> |
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}} |
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| Section3 = {{Chembox Structure |
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| Structure_ref =<ref name=DunitzShearer1960>{{cite journal |last1=Dunitz |first1=JD |author-link1=Jack D. Dunitz |last2=Shearer |first2=HMM |title=Die Strukturen der mittleren Ringverbindungen III. Die Struktur des Cyclododecans |journal=Helvetica Chimica Acta |date=1960 |volume=43 |issue=1 |pages=18–35 |doi=10.1002/hlca.19600430104}}</ref> |
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| CrystalStruct = Monoclinic |
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| SpaceGroup = C2/m |
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| PointGroup = D<sub>4</sub><ref name=Atavin1989>{{cite journal |last1=Atavin |first1=EG |last2=Mastryukov |first2=VS |last3=Allinger |first3=NL |last4=Almenningen |first4=A |last5=Seip |first5=R |title=Molecular structure of cyclododecane, C<sub>12</sub>H<sub>24</sub>, as determined by electron diffraction and molecular mechanics |journal=Journal of Molecular Structure |date=September 1989 |volume=212 |pages=87–95 |doi=10.1016/0022-2860(89)85069-0}}</ref> |
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| LattConst_a = 13.27 Å |
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| LattConst_b = 8.28 Å |
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| LattConst_c = 5.44 Å |
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| LattConst_beta = 99.5 |
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| UnitCellVolume = 589.7 Å<sup>3</sup> |
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| UnitCellFormulas = 2 |
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}} |
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| Section4 = {{Chembox Hazards |
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| FlashPtC = 87.6 |
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| HPhrases = {{H-phrases|413}}<ref name="PubChem" /> |
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| PPhrases = {{P-phrases|273|501}}<ref name="PubChem" /> |
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'''Cyclododecane''' is an organic ] with the ] C<sub>12</sub>H<sub>24</sub>. |
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'''Cyclododecane''' is an ] with the ] (CH<sub>2</sub>)<sub>12</sub>.<ref name="PubChem">{{Cite PubChem|cid=9268|title=Cyclododecane|access-date=2021-09-01}}</ref> It is a waxy white solid at room temperature,<ref name=":0" />{{Rp|17}} and is soluble in nonpolar organic solvents. |
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It is an ] of ], ], and synthetic lubricating oils.<ref name="PubChem" />{{Rp|8.1}} It is also used as a temporary ] to stabilise fragile objects or to seal water-sensitive parts; it slowly ] over days or weeks without leaving any residue.<ref name=":0" />{{Rp|17}} |
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Cyclododecane is mainly used as an ] in production of ]s, ]s, and other chemicals. |
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==Synthesis== |
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Cyclododecane is also used as a ], a temporary ] for sealing and conservation of ] and structurally weak materials, e.g. during ] and transport of ] objects and in ], e.g. to protect water-sensitive parts during cleaning. Due to its relatively slow evaporation in comparison with other volatile binding mediums the layer can last for several weeks. Very pure material has to be used so it does not leave any residue. Cyclododecane can be applied in molten state or dissolved in a nonpolar ]. Other volatile binding mediums in use are ], ] and with some limits ]. |
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Cyclododecane is produced industrially through catalytic trimerisation of ] to ], followed by hydrogenation.<ref>{{cite book|first=Hans-Jürgen|last=Arpe|title=Industrielle Organische Chemie|date=12 March 2007 |lang=de|page=291|publisher=John Wiley & Sons |isbn=978-3-527-31540-6}}</ref> |
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==Uses== |
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Cyclododecane is highly volatile. It is persistent in the environment, as it does not biodegrade easily and does not under go ]. Cyclododecane is ], usually present in the environment as adsorbed on the surface of soil particles. Due to its tendency to persist in ] it has a very high potential to ]. |
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It is a precursor to ], a precursor to the polymer ].<ref>{{Cite encyclopedia|last1=Schiffer|first1=T.|last2=Oenbrink|first2=G.|title=Cyclododecanol, Cyclododecanone, and Laurolactam|encyclopedia=Ullman's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|date=2009|doi=10.1002/14356007.a08_201.pub2|isbn=978-3527306732 }}</ref> |
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] |
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Cyclododecane is also an intermediate in production of ]s, ]s, and other chemicals. |
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{{hydrocarbon-stub}} |
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Cyclododecane is also used as a ], a temporary binder for sealing and conservation of ] and structurally weak materials, e.g. during ] and transport of ] objects and in ], e.g. to protect water-sensitive parts during cleaning.<ref name=":0">{{cite journal | doi = 10.1179/sic.2008.53.Supplement-2.17 | title = The uses of cyclododecane in conservation | journal = Studies in Conservation | volume = 53 | pages = 17–31 | year = 2008 | last1 = Rowe | first1 = Sophie | last2 = Rozeik | first2 = Christina | s2cid = 192201300 }}</ref> Due to its relatively slow evaporation in comparison with other volatile binding mediums the layer can last for several weeks. Very pure material has to be used so it does not leave any residue. Cyclododecane can be applied in molten state or dissolved in a nonpolar ]. Other volatile binding mediums in use are ], ] and with some limits ]. |
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==Environmental considerations== |
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Cyclododecane is persistent in the environment, as it does not biodegrade easily. Cyclododecane is ], usually present in the environment as adsorbed on the surface of soil particles. It has the potential to ]. Cyclododecane may cause long lasting harmful effects to aquatic life.<ref>{{cite web | url = https://echa.europa.eu/brief-profile/-/briefprofile/100.005.486 | title = Cyclododecane | publisher = European Chemicals Agency }}</ref> |
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==Conformation== |
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Cyclododecane has low ]. It adopts a ] ] with square (]) symmetry.<ref name=Atavin1989/><ref name=Wilen1994>{{cite book |last1=Wilen |first1=Samuel H. |last2=Eliel |first2=Ernest Ludwig |author-link2=Ernest L. Eliel |last3=Mander |first3=Lewis N. |author-link3=Lew Mander |title=Stereochemistry of organic compounds |date=1994 |publisher=Wiley |location=New York |isbn=9780471016700 |page=769 |url=https://archive.org/details/stereochemistryo0000elie_a9t3/page/768/mode/2up?q=3333}}</ref><ref name=Dragojlovic2015>{{cite journal |last1=Dragojlovic |first1=Veljko |title=Conformational analysis of cycloalkanes |journal=ChemTexts |date=September 2015 |volume=1 |issue=3 |doi=10.1007/s40828-015-0014-0 |url=https://link.springer.com/article/10.1007/s40828-015-0014-0#Fig70}}</ref>{{rp|at=Fig. 70}}<ref name=condis>{{cite book |author-last1=Wunderlich |author-first1=Bernhard |author-last2=Möller |author-first2=Martin |author-last3=Grebowicz |author-first3=Janusz |author-last4=Baur |author-first4=Herbert |title=Conformational Motion and Disorder in Low and High Molecular Mass Crystals |date=1988 |publisher=Springer-Verlag Springer e-books |location=Berlin, Heidelberg |isbn=978-3-540-38867-8 |chapter=Condis crystals of cyclic alkanes, silanes and related compounds |pages=26–44 |doi=10.1007/BFb0008610}}</ref>{{rp|p=24}} While highly stable, this conformation is not derivable from a ],<ref name=Dragojlovic2015/> unlike the lowest-energy conformations of ], ], and ].<ref name=Wilen1994/> Monosubstituted cyclododecanes also typically adopt the conformation,<ref>{{cite journal |last1=Khorasani |first1=Sanaz |last2=Fernandes |first2=Manuel A. |last3=Perry |first3=Christopher B. |title=Do 12-Membered Cycloalkane Rings Only Exist As One Conformation in the Solid-State? A Detailed Solid-State Analysis Involving Polymorphs of N,N'-Biscyclododecyl Pyromellitic Diimide |journal=Crystal Growth & Design |date=5 December 2012 |volume=12 |issue=12 |pages=5908–5916 |doi=10.1021/cg300765b}}</ref>{{rp|p=5916}} though more highly substituted cyclododecanes may adopt alternative conformations, such as .<ref>{{cite journal |last1=Skibinski |first1=Maciej |last2=Wang |first2=Yi |last3=Slawin |first3=Alexandra M. Z. |last4=Lebl |first4=Tomas |last5=Kirsch |first5=Peer |last6=O'Hagan |first6=David |title=Alicyclic Ring Structure: Conformational Influence of the CF<sub>2</sub> Group in Cyclododecanes |journal=Angewandte Chemie International Edition |date=4 November 2011 |volume=50 |issue=45 |pages=10581–10584 |doi=10.1002/anie.201105060}}</ref>{{rp|p=10583}} |
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==References== |
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{{Reflist}} |
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==External links== |
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*{{Commonscatinline}} |
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{{cycloalkanes}} |
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{{cycloalkanes}} |
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