| Revision as of 11:31, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit |
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{{redirect|Cetane|the diesel fuel analysis|Cetane number}} |
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{{chembox |
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{{chembox|Watchedfields=changed|verifiedrevid=443855529|ImageFile=Hexadecane.svg|ImageFile_Ref={{chemboximage|correct|??}}|ImageSize=280|ImageAlt=Structural formula of hexadecane|ImageFile1=Hexadecane 3D ball.png|ImageFile1_Ref={{chemboximage|correct|??}}|ImageSize1=280|ImageAlt1=Ball-and-stick model of the hexadecane molecule|ImageFile2=Hexadecane 3d.png|PIN=Hexadecane<ref>{{PubChem|11006}}</ref> |
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| Watchedfields = changed |
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|OtherNames=Cetane |
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| verifiedrevid = 408947052 |
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|Section1={{Chembox Identifiers |
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| Reference = <ref></ref> |
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| CASNo = 544-76-3 |
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| ImageFile = Hexadecane.svg |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ImageSize = 290 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ImageName = Skeletal formula of hexadecane |
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| UNII = F8Z00SHP6Q |
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| ImageFile1 = Hexadecane-3D-balls.png |
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| ImageSize1 = 300 |
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| PubChem = 11006 |
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| ChemSpiderID = 10540 |
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| ImageName1 = Ball-and-stick model of hexadecane |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| IUPACName = Hexadecane |
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| EINECS = 208-878-9 |
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| OtherNames = Cetane<br>''n''-Hexadecane |
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| MeSHName = n-hexadecane |
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| Section1 = {{Chembox Identifiers |
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| ChEBI = 45296 |
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| InChIKey = DCAYPVUWAIABOU-UHFFFAOYAR |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 134994 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 134994 |
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| Beilstein = 1736592 |
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| Gmelin = 103739 |
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| SMILES = CCCCCCCCCCCCCCCC |
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| StdInChI = 1S/C16H34/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h3-16H2,1-2H3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DCAYPVUWAIABOU-UHFFFAOYSA-N |
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| StdInChI = 1S/C16H34/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h3-16H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}}|Section2={{Chembox Properties |
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| StdInChIKey = DCAYPVUWAIABOU-UHFFFAOYSA-N |
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| C=16 | H=34 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Appearance = Colourless liquid |
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| CASNo = 544-76-3 |
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| Odor = Gasoline-like to odorless |
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| EINECS = 208-878-9 |
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| Density = 0.77 g/cm<sup>3</sup><ref name=CRC/><ref name=GESTIS>{{GESTIS|ZVG=13200}}</ref> |
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| PubChem = 11006 |
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| MeltingPtC = 18.18 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| MeltingPt_ref = <ref name=CRC>Haynes, p. 3.294</ref> |
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| ChemSpiderID = 10540 |
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| ChEBI = 45296 |
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| BoilingPtC = 286.9 |
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| BoilingPt_ref = <ref name=CRC/> |
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| SMILES = CCCCCCCCCCCCCCCC |
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| LogP = 8.859 |
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| InChI = 1/C16H34/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h3-16H2,1-2H3 |
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| VaporPressure = < 0.1 mbar (20 °C) |
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}} |
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| HenryConstant = 43 nmol Pa<sup>−1</sup> kg<sup>−1</sup> |
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| Section2 = {{Chembox Properties |
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| RefractIndex = 1.4329<ref name=CRC/> |
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| C=16|H=34 |
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| MagSus = -187.6·10<sup>−6</sup> cm<sup>3</sup>/mol<ref>Haynes, p. 3.578</ref> |
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| Appearance = |
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| Viscosity = 3.03 mPa·s<ref>Haynes, p. 6.245</ref> |
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| Density = |
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| ThermalConductivity = 0.140 W/(m·K)<ref>Haynes, p. 6.256</ref> |
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| MeltingPtC = 18 |
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}}|Section3={{Chembox Thermochemistry |
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| BoilingPtC = 287 |
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| Thermochemistry_ref =<ref>Haynes, p. 5.21</ref> |
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| Solubility = Insoluble |
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| DeltaHf = −456.1 kJ mol<sup>−1</sup> |
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| Specific Heat Capacity (liq)=2.20(+-0.1093) kJ/kg/K <ref>"Determination of enthalpy temperature curves of phase change materials with the temperature-history method: improvement to the temperature dependent properties" Table 1 by Marin et al. Measurement Science and Technology V 14 pg184-189 , http://iopscience.iop.org/0957-0233/14/2/305 accessed 2011.01.19</ref> |
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| DeltaHc = |
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| Specific Heat Capacity (solid)=2.25 (+-0.2549) kJ/kg/K <ref>"Determination of enthalpy temperature curves of phase change materials with the temperature-history method: improvement to the temperature dependent properties" Table 1 by Marin et al. Measurement Science and Technology V 14 pg184-189 , http://iopscience.iop.org/0957-0233/14/2/305 accessed 2011.01.19</ref> |
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| Entropy = |
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| Heat of Fusion = 252.01 (+-15.18)<ref>"Determination of enthalpy temperature curves of phase change materials with the temperature-history method: improvement to the temperature dependent properties" Table 1 by Marin et al. Measurement Science and Technology V 14 pg184-189 , http://iopscience.iop.org/0957-0233/14/2/305 accessed 2011.01.19</ref> |
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| HeatCapacity = 501.6 J K<sup>−1</sup> mol<sup>−1</sup> |
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}}|Section4={{Chembox Hazards |
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| GHSPictograms = {{gHS exclamation mark}} |
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| GHSSignalWord = '''WARNING''' |
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| HPhrases = {{h-phrases|315}} |
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| FlashPtC =136 |
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| FlashPt_ref = <ref name=CRC2>Haynes, p. 16.25</ref> |
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| AutoignitionPtC =202 |
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| AutoignitionPt_ref = <ref name=CRC2/> |
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}}|Section5={{Chembox Related |
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| OtherFunction_label = alkanes |
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| OtherFunction = {{unbulleted list|]|]}} |
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}}}} |
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'''Hexadecane''' (also called '''cetane''') is an ] ] with the ] C<sub>16</sub>H<sub>34</sub>. Hexadecane consists of a chain of 16 ]s, with three ]s bonded to the two end carbon atoms, and two hydrogens bonded to each of the 14 other carbon atoms. |
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==Cetane number== |
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{{main|Cetane number}} |
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''Cetane'' is often used as a shorthand for ], a measure of the combustion of ].<ref name="McKinsey">{{Cite web |title=Cetane |url=http://www.mckinseyenergyinsights.com/resources/refinery-reference-desk/cetane/ |access-date=2021-02-24 |website=www.mckinseyenergyinsights.com |language=en |archive-date=2020-06-29 |archive-url=https://web.archive.org/web/20200629191931/https://www.mckinseyenergyinsights.com/resources/refinery-reference-desk/cetane/ |url-status=live }}</ref> Cetane ignites very easily under compression; for this reason, it is assigned a cetane number of 100, and serves as a reference for other fuel mixtures.<ref name="Speight2015">{{Cite book |last=Speight |first=James G. |url=https://www.worldcat.org/oclc/903318141 |title=Handbook of Petroleum Product Analysis. |publisher=Wiley |year=2015 |isbn=978-1-322-95015-0 |location=Hoboken, NJ |pages=158–159 |oclc=903318141}}</ref> |
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==Hexadecyl radical== |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = {{convert|135|C|F}} |
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| Autoignition = {{convert|201|C|F}} |
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}} |
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}} |
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Hexadecyl is an ] ] of ] and ] derived from hexadecane, with formula C<sub>16</sub>H<sub>33</sub> and with mass 225.433,<ref name="csh">{{cite news |title=Hexadecyl |url=http://www.chemspider.com/Chemical-Structure.150674.html |access-date=3 April 2021 |agency=ChemSpider |publisher=Royal Society of Chemistry}}</ref> occurring especially in ] alcohol.<ref name="mwh">{{cite news |title=hexadecyl noun |url=https://www.merriam-webster.com/dictionary/hexadecyl |publisher=Merriam-Webster}}</ref> It confers strong hydrophobicity on molecules containing it.<ref name="horvath11">{{cite book |last1=Hatanaka |first1=K |editor1-last=Horváth |editor1-first=István T. |title=Fluorous Chemistry |date=2011 |publisher=Springer Science & Business Media |page=294 |isbn=9783642252334 |url=https://books.google.com/books?id=7KdIV-iPA5cC&pg=PA294}}</ref> ] modified with hexadecyl and ] has increased ] and ], proposed to useful in ], specifically ].<ref name="lang21">{{cite journal |doi=10.1080/10717544.2021.1938754|title=Prodrug-based nano-delivery strategy to improve the antitumor ability of carboplatin in vivo and in vitro|year=2021|last1=Lang|first1=Tingting|last2=Li|first2=Nuannuan|last3=Zhang|first3=Jing|last4=Li|first4=Yi|last5=Rong|first5=Rong|last6=Fu|first6=Yuanlei|journal=Drug Delivery|volume=28|issue=1|pages=1272–1280|pmid=34176381|pmc=8238065}}</ref> |
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'''Hexadecane''' (also called '''cetane''') is an ] ] with the ] C<sub>16</sub>H<sub>34</sub>. Hexadecane consists of a chain of 16 carbon atoms, with three hydrogen atoms bonded to the two end carbon atoms, and two hydrogens bonded to each of the 14 other carbon atoms. It has 10,359 ]s. |
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Hexadecyl was used from 1982 for ],<ref name="pool82">{{cite journal |doi=10.1007/BF02535225|title=Use of radiolabeled hexadecyl cholesteryl ether as a liposome marker|year=1982|last1=Pool|first1=G. L.|last2=French|first2=M. E.|last3=Edwards|first3=R. A.|last4=Huang|first4=L.|last5=Lumb|first5=R. H.|journal=Lipids|volume=17|issue=6|pages=448–452|pmid=7050582|s2cid=42583970}}</ref> and this continues to be useful,<ref name="kollareth17">{{cite journal |doi=10.1016/j.bbrep.2017.10.007|title=Radiolabeled cholesteryl ethers: A need to analyze for biological stability before use|year=2018|last1=Manual Kollareth|first1=Denny Joseph|last2=Chang|first2=Chuchun L.|last3=Hansen|first3=Inge H.|last4=Deckelbaum|first4=Richard J.|journal=Biochemistry and Biophysics Reports|volume=13|pages=1–6|pmid=29188234|pmc=5697731}}</ref> for example for radiolabelling ] and ],<ref name="lee17">{{cite book |last1=Lee |first1=Yanick |title=Radiosynthesis of hexadecyl-4-fluorobenzoate for labeling exosomes and chitosan hydrogels |date=July 2017 |publisher=Université de Montréal |url=https://papyrus.bib.umontreal.ca/xmlui/bitstream/handle/1866/19446/Lee_Yanick_2017_memoire.pdf?sequence=2&isAllowed=y |format=Master's thesis}}</ref> |
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''Cetane'' is often used as a short-hand for ], a measure of the detonation of ]. Cetane ignites very easily under compression; for this reason, it is assigned a cetane number of 100, and serves as a reference for other fuel mixtures. |
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and for ].<ref name="krpat">{{cite news |title=Radioactive cell labeling agent |url=https://patents.google.com/patent/KR101130737B1/en |work=KR101130737B1 |date=2012}}</ref> |
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Hexadecyl ] has profound effects on the lung,<ref name="haroldsen87">{{cite journal |doi=10.1172/JCI113028|title=Metabolism of platelet-activating factor in isolated perfused rat lung|year=1987|last1=Haroldsen|first1=P. E.|last2=Voelkel|first2=N. F.|last3=Henson|first3=J. E.|last4=Henson|first4=P. M.|last5=Murphy|first5=R. C.|journal=Journal of Clinical Investigation|volume=79|issue=6|pages=1860–1867|pmid=3108322|pmc=424530}}</ref> and hexadecyl glyceryl ether participates in the ] of ].<ref name="wood70">{{cite journal |doi=10.1016/0006-291x(70)90697-2|title=Tumor lipids: Biosynthesis of plasmalogens|year=1970|last1=Wood|first1=Randall|last2=Healy|first2=Kathleen|journal=Biochemical and Biophysical Research Communications|volume=38|issue=2|pages=205–211|pmid=5418699}}</ref> |
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It has one of the lowest ]s, at <−30.<ref>, Purdue University</ref> |
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==See also== |
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==See also== |
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==References== |
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==References== |
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{{reflist}} |
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<references/> |
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==Cited sources== |
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== External links == |
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*{{cite book | editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293}} |
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==External links== |
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{{engineering-stub}} |
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{{alkanes}} |
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{{alkanes}} |
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