Difference between revisions of "(E)-1,4-Dichlorobut-2-ene"
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{{chembox | {{chembox | ||
| + | | Name = (''E'')-1,4-Dichlorobut-2-ene | ||
| Section1 = {{Chembox Identifiers | | Section1 = {{Chembox Identifiers | ||
| InChI = 1/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+ | | InChI = 1/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+ | ||
| Line 7: | Line 8: | ||
| ChemSpiderID = 557415 | | ChemSpiderID = 557415 | ||
| CASNo = 110-57-6 <!-- CASRN verified at ESIS and NIST --> | | CASNo = 110-57-6 <!-- CASRN verified at ESIS and NIST --> | ||
| − | | | + | | EC-number = 203-779-7 |
}} | }} | ||
| Section2 = {{Chembox Properties | | Section2 = {{Chembox Properties | ||
| − | | Reference = <ref>{{NIST | + | | Reference = <ref>{{NIST chemistry|id=1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+|name=2-Butene, 1,4-dichloro-, (E)-|accessdate=2009-08-21}}.</ref> |
| Formula = C<sub>4</sub>H<sub>6</sub>Cl<sub>2</sub> | | Formula = C<sub>4</sub>H<sub>6</sub>Cl<sub>2</sub> | ||
| MolarMass = 125.00 g/mol | | MolarMass = 125.00 g/mol | ||
| − | | BoilingPt = 75 ºC at 53 mbar | + | | BoilingPt = 75 ºC at 53 mbar (41 Torr) |
}} | }} | ||
| Section7 = {{Chembox Hazards | | Section7 = {{Chembox Hazards | ||
| Reference = <ref>{{CLP Regulation|index=602-073-00-X|page=473}}</ref> | | Reference = <ref>{{CLP Regulation|index=602-073-00-X|page=473}}</ref> | ||
| EUIndex = 602-073-00-X | | EUIndex = 602-073-00-X | ||
| − | + | | GHSPictograms = {{GHS06}}{{GHS08}}<br/>{{GHS05}}{{GHS09}} | |
| − | |||
| − | |||
| − | | GHSPictograms = {{GHS06}}{{GHS08}}{{GHS05}}{{GHS09}} | ||
| GHSSignalWord = DANGER | | GHSSignalWord = DANGER | ||
| − | | HPhrases = | + | | HPhrases = {{H-phrases|350|330|311|301|314|410}} |
| PPhrases = | | PPhrases = | ||
}} | }} | ||
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'''(''E'')-1,4-Dichlorobut-2-ene''' is a chlorinated [[butene]]. Along with its [[(Z)-1,4-Dichlorobut-2-ene|(''Z'')-isomer]], it is an intermediate in the industrial production of [[chloroprene]], and the main impurity in technical grade chloroprene.<ref>{{citation | chaptertitle = Chloroprene | 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}}.</ref> It is also one of the starting materials for [[Birman's synthesis of sceptrin|Birman's total synthesis]] of the 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}}. {{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}}.</ref> | '''(''E'')-1,4-Dichlorobut-2-ene''' is a chlorinated [[butene]]. Along with its [[(Z)-1,4-Dichlorobut-2-ene|(''Z'')-isomer]], it is an intermediate in the industrial production of [[chloroprene]], and the main impurity in technical grade chloroprene.<ref>{{citation | chaptertitle = Chloroprene | 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}}.</ref> It is also one of the starting materials for [[Birman's synthesis of sceptrin|Birman's total synthesis]] of the 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}}. {{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}}.</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 °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>{{Ullmann5th | last = Kleinschmidt | first = P. | contribution = Chlorinated hydrocarbons. 6.4. 2-Chloro-1,3-butadiene | volume = A6 | pages = 315–18}}. {{Kirk-Othmer4th | last = Stewart | first = C. A., Jr. | ||
| + | | contribution = Chlorocarbons, -hydrocarbons (chloroprene) | volume = 6 | pages = 70–78}}.</ref> | ||
==References== | ==References== | ||
Latest revision as of 09:18, 24 August 2009
| (E)-1,4-Dichlorobut-2-ene | |
|---|---|
| Identifiers | |
| InChI | InChI=1/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+ |
| InChIKey | FQDIANVAWVHZIR-OWOJBTEDBY |
| Standard InChI | InChI=1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+ |
| Standard InChIKey | FQDIANVAWVHZIR-OWOJBTEDSA-N |
| CAS number | [] |
| EC number | |
| ChemSpider | |
| Properties[1] | |
| Chemical formula | C4H6Cl2 |
| Molar mass | 125.00 g/mol |
| Boiling point |
75 ºC at 53 mbar (41 Torr) |
| Hazards[2] | |
| EU index number | 602-073-00-X |
| GHS pictograms |    
|
| GHS signal word | DANGER |
| GHS hazard statements | H350, H330, H311, H301, H314, H410 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
(E)-1,4-Dichlorobut-2-ene is a chlorinated butene. Along with its (Z)-isomer, it is an intermediate in the industrial production of chloroprene, and the main impurity in technical grade chloroprene.[3] It is also one of the starting materials for Birman's total synthesis of the poriferic natural product sceptrin.[4]
Production of chloroprene
Chloroprene is a monomer for the production of synthetic rubbers 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 °C in the presence of a catalyst. Finally, dehydrochlorination (elimination of hydrogen chloride) of 3,4-dichlorobut-1-ene with dilute sodium hydroxide solution in the presence of polymerization inhibitors gives crude chloroprene.[5]
References
- ↑ 2-Butene, 1,4-dichloro-, (E)-. In NIST Chemistry WebBook; National Institute for Standards and Technology, <http://webbook.nist.gov/cgi/inchi/InChI%3D1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+>. (accessed 21 August 2009).
- ↑ Index no. 602-073-00-X of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 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 (EC) No 1907/2006. OJEU L353, 31.12.2008, pp 1–1355 at p 473.
- ↑ Chloroprene. In Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide; IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 71; International Agency for Research on Cancer: Lyon, France, 1999; pp 227–50. ISBN 92-832-1271-1, <http://monographs.iarc.fr/ENG/Monographs/vol71/mono71-9.pdf>.
- ↑ Birman, Vladimir B.; Jiang, Xun-Tian Synthesis of Sceptrin Alkaloids. Org. Lett. 2004, 6 (14), 2369–71. DOI: 10.1021/ol049283g. Baran, Phil S.; Zografos, Alexandros L.; O'Malley, Daniel P. Short Total Synthesis of (±)-Sceptrin. J. Am. Chem. Soc. 2004, 126 (12), 3726–27. DOI: 10.1021/ja049648s.
- ↑ Kleinschmidt, P. Chlorinated hydrocarbons. 6.4. 2-Chloro-1,3-butadiene. In Ullmann’s Encyclopedia of Industrial Chemistry, 5th ed.; Gerhartz, W.; Yamamoto, Y. S., Eds.; VCH: Weinheim, 1986; Vol. A6, pp 315–18. Stewart, C. A., Jr. Chlorocarbons, -hydrocarbons (chloroprene). In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I.; Howe-Grant, M., Eds.; John Wiley: New York, 1994; Vol. 6, pp 70–78.
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