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Article: Catalytic Dehalogenation of Highly Chlorinated Benzenes and Aroclors Using PdCl2(dppf) and NaBH4: Efficiency, Selectivity, and Base Support

TitleCatalytic Dehalogenation of Highly Chlorinated Benzenes and Aroclors Using PdCl2(dppf) and NaBH4: Efficiency, Selectivity, and Base Support
Authors
Issue Date1998
Citation
Journal of Organic Chemistry, 1998, v. 63, n. 11, p. 3538-3543 How to Cite?
AbstractReported herein is a convenient one-pot system that can dehalogenate highly chlorinated benzenes at room temperature with reasonable conversion rates using PdCl2(dppf) (dppf = 1,1′-bis-(diphenylphosphino)ferrocene) as catalyst, NaBH4 as reducing agent, TMEDA (N,N,N',N'-tetra-methyl-1,2-ethylenediamine) as supporting base, and THF as solvent. Total conversion of substrate to less chlorinated isomers is achieved within 200 h when hexachloro-, pentachloro-, and tetrachlorobenzenes are used. Degradation to benzene is not achievable, but the efficiency shown in the partial dechlorination is encouraging. A pronounced selectivity is accomplished with removal of meta-substituted chlorines being preferred over ortho- or para-substituted Cl atoms. The sequence in which reagents are added is also critical, thus indicating a protective role of the base. The effectiveness of the method was tested on the PCB mixtures Aroclor 1242, 1248, and 1254. Dechlorination efficiency at 67 °C is satisfactory.
Persistent Identifierhttp://hdl.handle.net/10722/219350
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095

 

DC FieldValueLanguage
dc.contributor.authorLassová, Luisa-
dc.contributor.authorLee, Hian Kee-
dc.contributor.authorHor, T. S Andy-
dc.date.accessioned2015-09-23T02:56:51Z-
dc.date.available2015-09-23T02:56:51Z-
dc.date.issued1998-
dc.identifier.citationJournal of Organic Chemistry, 1998, v. 63, n. 11, p. 3538-3543-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/10722/219350-
dc.description.abstractReported herein is a convenient one-pot system that can dehalogenate highly chlorinated benzenes at room temperature with reasonable conversion rates using PdCl2(dppf) (dppf = 1,1′-bis-(diphenylphosphino)ferrocene) as catalyst, NaBH4 as reducing agent, TMEDA (N,N,N',N'-tetra-methyl-1,2-ethylenediamine) as supporting base, and THF as solvent. Total conversion of substrate to less chlorinated isomers is achieved within 200 h when hexachloro-, pentachloro-, and tetrachlorobenzenes are used. Degradation to benzene is not achievable, but the efficiency shown in the partial dechlorination is encouraging. A pronounced selectivity is accomplished with removal of meta-substituted chlorines being preferred over ortho- or para-substituted Cl atoms. The sequence in which reagents are added is also critical, thus indicating a protective role of the base. The effectiveness of the method was tested on the PCB mixtures Aroclor 1242, 1248, and 1254. Dechlorination efficiency at 67 °C is satisfactory.-
dc.languageeng-
dc.relation.ispartofJournal of Organic Chemistry-
dc.titleCatalytic Dehalogenation of Highly Chlorinated Benzenes and Aroclors Using PdCl2(dppf) and NaBH4: Efficiency, Selectivity, and Base Support-
dc.typeArticle-
dc.description.natureLink_to_subscribed_fulltext-
dc.identifier.scopuseid_2-s2.0-0000465248-
dc.identifier.volume63-
dc.identifier.issue11-
dc.identifier.spage3538-
dc.identifier.epage3543-

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