Difference between revisions of "(E)-1,4-Dichlorobut-2-ene"
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| − | | | + | | 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 32: | Line 32: | ||
==Production of chloroprene== | ==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. 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>{{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> | + | 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>{{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== | ==References== | ||
Revision as of 09:47, 18 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 | [] |
| ChemSpider | |
| Properties[1] | |
| Chemical formula | C4H6Cl2 |
| Molar mass | 125.00 g/mol |
| Boiling point |
75 ºC at 53 mbar |
| 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
- ↑ 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+>
- ↑ 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, 1993; Vol. 6, pp 70–78.
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