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| verifiedrevid = 371084998 |
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| Watchedfields = changed |
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| Name = Sebacoyl chloride |
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| verifiedrevid = 432939426 |
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| ImageFile = Sebacoyl-chloride-2D-skeletal.png |
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| Name = Sebacoyl chloride |
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| ImageSize = 240px |
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| ImageFile = Sebacoyl-chloride-2D-skeletal.png |
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| ImageName = Skeletal formula of sebacoyl chloride |
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| ImageSize = 240px |
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| ImageFile1 = Sebacoyl-chloride-3D-balls.png |
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| ImageName = Skeletal formula of sebacoyl chloride |
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| ImageSize1 = 240px |
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| ImageFile1 = Sebacoyl-chloride-3D-balls.png |
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| ImageName1 = Ball-and-stick model |
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| ImageSize1 = 240px |
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| IUPACName = Decanedioyl dichloride |
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| ImageName1 = Ball-and-stick model |
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| OtherNames = Sebacoyl dichloride |
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| PIN = Decanedioyl dichloride |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Sebacoyl dichloride |
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| CASNo = 111-19-3 |
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|Section1={{Chembox Identifiers |
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| SMILES = ClC(=O)CCCCCCCC(=O)CCl |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 111-19-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 8JT2RJH7AU |
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| SMILES = ClC(=O)CCCCCCCC(=O)CCl |
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| EINECS = 203-843-4 |
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| PubChem = 66072 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 59462 |
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| InChI = 1/C10H16Cl2O2/c11-9(13)7-5-3-1-2-4-6-8-10(12)14/h1-8H2 |
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| InChIKey = WMPOZLHMGVKUEJ-UHFFFAOYAH |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C10H16Cl2O2/c11-9(13)7-5-3-1-2-4-6-8-10(12)14/h1-8H2 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = WMPOZLHMGVKUEJ-UHFFFAOYSA-N |
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| RTECS = |
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| MeSHName = C061659 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>16</sub>Cl<sub>2</sub>O<sub>2</sub> |
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| Formula = C<sub>10</sub>H<sub>16</sub>Cl<sub>2</sub>O<sub>2</sub> |
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| MolarMass = 239.14 g/mol |
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| MolarMass = 239.14 g/mol |
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| Density = 1.12 g cm<sup>3</sup> |
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| Density = 1.12 g cm<sup>−3</sup> |
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| MeltingPt = −2.5 °C |
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| MeltingPtC = −2.5 |
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| BoilingPt = 220 °C |
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| BoilingPtC = 220 |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| NFPA-H = 3 |
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| NFPA-H = 3 |
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| NFPA-F = 0 |
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| NFPA-F = 0 |
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| NFPA-R = 2 |
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| NFPA-R = 2 |
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| NFPA-O = W |
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| NFPA-S = W |
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| ExternalMSDS = |
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| ExternalSDS = |
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'''Sebacoyl chloride''' (or '''sebacoyl dichloride''') is a di-], with formula (CH<sub>2</sub>)<sub>8</sub>(COCl)<sub>2</sub>. A colorless oily liquid with a pungent odor, it is soluble in hydrocarbons and ethers. Sebacoyl chloride is corrosive; like all ]s, it hydrolyzes, evolving ]. It is less susceptible to ] though than shorter chain aliphatic acyl chlorides.<ref>{{cite journal|last1=Morgan|first1=Paul W.|last2=Kwolek|first2=Stephanie L.|title=The nylon rope trick: Demonstration of condensation polymerization|journal=Journal of Chemical Education|date=April 1959|volume=36|issue=4|pages=182|doi=10.1021/ed036p182|bibcode=1959JChEd..36..182M}}</ref> |
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'''Sebacoyl chloride''' (or '''sebacoyl dichloride''') is a di-], with formula C<sub>10</sub>H<sub>16</sub>Cl<sub>2</sub>O<sub>2</sub>. |
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==Preparation== |
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Sebacoyl chloride is a light-yellow liquid with a pungent odor, soluble in hydrocarbons and ethers. |
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Sebacoyl chloride can be prepared by reacting ] with an excess of ]. Residual thionyl chloride can be removed by ].<ref>{{cite journal|last1=Erdmann|first1=L.|last2=Uhrich|first2=K.E.|title=Synthesis and degradation characteristics of salicylic acid-derived poly(anhydride-esters)|journal=Biomaterials|date=October 2000|volume=21|issue=19|pages=1941–1946|doi=10.1016/S0142-9612(00)00073-9|pmid=10941915}}</ref> |
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Sebacoyl chloride is corrosive; like all ]s, it hydrolyzes in water rapidly, evolving ]. |
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== Use == |
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Sebacoyl chloride can be reacted with ], to give the polymer, ]. |
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Sebacoyl chloride can be ] with ] yielding ].<ref>{{Cite journal|last1=Enkelmann|first1=Volker|last2=Wegner|first2=Gerhard|date=1976-11-01|title=Mechanism of interfacial polycondensation and the direct synthesis of stable polyamide membranes|journal=Die Makromolekulare Chemie|language=en|volume=177|issue=11|pages=3177–3189|doi=10.1002/macp.1976.021771106|issn=0025-116X}}</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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{{Unreferenced|date =September 2007}} |
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{{reflist}} |
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{{reflist}} |
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{{Navbox acyl chlorides}} |
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