View source for 1,4-Dichlorobut-2-ene

{{Orphan|date=January 2010}}
{{chembox
| ImageFile=1,4-Dichlorobut-2-ene.svg
| Section1 = {{Chembox Identifiers
|   InChI = 1/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+
|   StdInChI = 1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+
|   InChIKey = FQDIANVAWVHZIR-OWOJBTEDBY
|   StdInChIKey = FQDIANVAWVHZIR-OWOJBTEDSA-N
|   ChemSpiderID = 557415
|   SMILES = ClC/C=C/CCl
| CASNo = 110-57-6
|   CASNo_Comment =  <!-- CASRN verified at ESIS and NIST -->
|   EC-number = 203-779-7
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>4</sub>H<sub>6</sub>Cl<sub>2</sub>
|   MolarMass = 125.00 g/mol
  }}
| Section7 = {{Chembox Hazards
|   Reference = <ref>Index no.&nbsp;602-073-00-X of Annex&nbsp;VI, Part&nbsp;3, to [http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2008:353:0001:1355:EN:PDF Regulation&nbsp;(EC) No&nbsp;1272/2008 of the European Parliament and of the Council of 16&nbsp;December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation&nbsp;(EC) No&nbsp;1907/2006]. ''OJEU'' L353, 31.12.2008, pp&nbsp;1–1355 at p&nbsp;473.</ref>
|   EUIndex = 602-073-00-X<!--
|   EUClass = Carc. Cat. 2<br/>Very toxic ('''T+''')<br/>Corrosive ('''C''')<br/>Dangerous for the environment ('''N''')
|   RPhrases = R45, R24/25, R26, R34, R50/53
|   SPhrases = S53, S45, S60, S61-->
|   GHSPictograms = {{GHS skull and crossbones}}{{GHS health hazard}}<br/>{{GHS corrosion}}{{GHS environment}}
|   GHSSignalWord = DANGER
|   HPhrases = {{H-phrases|350|330|311|301|314|410}}
|   PPhrases = 
  }}
}}

'''1,4-Dichlorobut-2-ene''' is a chlorinated [[butene]]. It is an intermediate in the industrial production of [[chloroprene]], and the main impurity in technical grade chloroprene.<ref>{{citation | pages = 227–50 | url = http://monographs.iarc.fr/ENG/Monographs/vol71/mono71-9.pdf | series = IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 71 | publisher = International Agency for Research on Cancer | location = Lyon, France | title = Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide | year = 1999 | isbn = 92-832-1271-1 | chapter-url = Chloroprene}}.</ref> The (''E'')-isomer is also one of the starting materials for [[Birman's synthesis of sceptrin|Birman's total synthesis]] of the [[Sponge|poriferic]] natural product [[sceptrin]].<ref name="sceptrin">{{citation | last1 = Birman | first1 = Vladimir B. | last2 = Jiang | first2 = Xun-Tian | title = Synthesis of Sceptrin Alkaloids | journal = Org. Lett. | year = 2004 | volume = 6 | issue = 14 | pages = 2369–71 | doi=10.1021/ol049283g | pmid = 15228281}}. {{citation | last1 = Baran | first1 = Phil S. | last2 = Zografos | first2 = Alexandros L. | last3 = O'Malley | first3 = Daniel P. | title = Short Total Synthesis of (±)-Sceptrin | journal = J. Am. Chem. Soc. | year = 2004 | volume = 126 | issue = 12 | pages = 3726–27 | doi=10.1021/ja049648s | pmid = 15038721}}.</ref>

==Production of chloroprene==
Chloroprene is a monomer for the production of [[synthetic rubber]]s such as [[Neoprene]]. It is produced from [[butadiene]] in a three-step process. The first step is the liquid- or vapour-phase chlorination of butadiene to a mixture of [[3,4-dichlorobut-1-ene]] and 1,4-dichlorobut-2-ene (both isomers). In the second step, the mixture of 1,4-dichlorobut-2-ene and 3,4-dichlorobut-1-ene is isomerized to pure 3,4-dichlorobut-1-ene by heating to temperatures of 60–120&nbsp;°C in the presence of a catalyst. Finally, [[dehydrochlorination]] ([[Elimination reaction|elimination]] of [[hydrogen chloride]]) of 3,4-dichlorobut-1-ene with dilute [[sodium hydroxide]] solution in the presence of [[polymerization inhibitor]]s gives crude chloroprene.<ref>{{citation | last = Kleinschmidt | first = P. | year = 1986 | contribution = Chlorinated hydrocarbons. 6.4. 2-Chloro-1,3-butadiene | editor1-last = Gerhartz | editor1-first = W. | editor2-last = Yamamoto | editor2-first = Y. S. | title = Ullmann’s Encyclopedia of Industrial Chemistry | edition = 5th | volume = A6 | location = Weinheim | publisher = VCH | pages = 315–18}}. {{citation | last = Stewart | first = C. A., Jr. | year = 1993 | contribution = Chlorocarbons, -hydrocarbons (chloroprene) | editor1-last = Kroschwitz | editor1-first = J. I. | editor2-last = Howe-Grant | editor2-first = M. | title = Kirk-Othmer Encyclopedia of Chemical Technology | edition = 4th | volume = 6 | location = New York | publisher = John Wiley | pages = 70–78}}. </ref>

==References==
{{reflist}}

{{DEFAULTSORT:Dichlorobutene-2, 1,4-}}
[[Category:Alkenes]]
[[Category:Organochlorides]]
[[Category:2Fix]]