Comparison of the epoxidation of cyclohexene, dicyclopentadiene and 1,5-cyclooctadiene over LDH hosted Fe and Mn sulfonato-salen complexes

Samiran Bhattacharjee, James Arthur Anderson

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

Sulfonato-salen metal complexes containing Fe or Mn metal centres have been synthesised and intercalated into Zn/Al layered double hydroxide hosts and used as catalyst for the epoxidation of cyclohexene, dicyclopentadiene and 1,5-cyclooctadiene. Using a combination of pivalaldehyde and molecular oxygen at atmospheric or higher pressures to produce the corresponding peracid as oxidant, cyclohexene gave two oxidation products, cyclohexene oxide and 2-cyclohexen-1-one, whereas, dicyclopentadiene was transformed exclusively into the corresponding mono-epoxide. The relative order of olefin activity correlates with the C-C=C bond angle for both metal centres. The product selectivity was found to be largely independent of the central metal ion suggesting that the local environment around the central metal ion was of greater importance. A possible mechanism-based on the product distribution is suggested. (c) 2006 Elsevier B.V. All rights reserved.

Original languageEnglish
Pages (from-to)103-110
Number of pages7
JournalJournal of Molecular Catalysis A: Chemical
Volume249
DOIs
Publication statusPublished - 2006

Keywords

  • chiral salen-metal compound
  • LDH host catalyst
  • layered double hydroxide
  • epoxidation
  • layered double hydroxides
  • hydrogen-peroxide
  • molecular-oxygen
  • selective oxidation
  • allylic alcohols
  • cyclic alkenes
  • catalysts
  • olefins
  • hydrotalcite
  • mechanism

Cite this

Comparison of the epoxidation of cyclohexene, dicyclopentadiene and 1,5-cyclooctadiene over LDH hosted Fe and Mn sulfonato-salen complexes. / Bhattacharjee, Samiran; Anderson, James Arthur.

In: Journal of Molecular Catalysis A: Chemical, Vol. 249, 2006, p. 103-110.

Research output: Contribution to journalArticle

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title = "Comparison of the epoxidation of cyclohexene, dicyclopentadiene and 1,5-cyclooctadiene over LDH hosted Fe and Mn sulfonato-salen complexes",
abstract = "Sulfonato-salen metal complexes containing Fe or Mn metal centres have been synthesised and intercalated into Zn/Al layered double hydroxide hosts and used as catalyst for the epoxidation of cyclohexene, dicyclopentadiene and 1,5-cyclooctadiene. Using a combination of pivalaldehyde and molecular oxygen at atmospheric or higher pressures to produce the corresponding peracid as oxidant, cyclohexene gave two oxidation products, cyclohexene oxide and 2-cyclohexen-1-one, whereas, dicyclopentadiene was transformed exclusively into the corresponding mono-epoxide. The relative order of olefin activity correlates with the C-C=C bond angle for both metal centres. The product selectivity was found to be largely independent of the central metal ion suggesting that the local environment around the central metal ion was of greater importance. A possible mechanism-based on the product distribution is suggested. (c) 2006 Elsevier B.V. All rights reserved.",
keywords = "chiral salen-metal compound, LDH host catalyst, layered double hydroxide, epoxidation, layered double hydroxides, hydrogen-peroxide, molecular-oxygen, selective oxidation, allylic alcohols, cyclic alkenes, catalysts, olefins, hydrotalcite, mechanism",
author = "Samiran Bhattacharjee and Anderson, {James Arthur}",
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AU - Anderson, James Arthur

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N2 - Sulfonato-salen metal complexes containing Fe or Mn metal centres have been synthesised and intercalated into Zn/Al layered double hydroxide hosts and used as catalyst for the epoxidation of cyclohexene, dicyclopentadiene and 1,5-cyclooctadiene. Using a combination of pivalaldehyde and molecular oxygen at atmospheric or higher pressures to produce the corresponding peracid as oxidant, cyclohexene gave two oxidation products, cyclohexene oxide and 2-cyclohexen-1-one, whereas, dicyclopentadiene was transformed exclusively into the corresponding mono-epoxide. The relative order of olefin activity correlates with the C-C=C bond angle for both metal centres. The product selectivity was found to be largely independent of the central metal ion suggesting that the local environment around the central metal ion was of greater importance. A possible mechanism-based on the product distribution is suggested. (c) 2006 Elsevier B.V. All rights reserved.

AB - Sulfonato-salen metal complexes containing Fe or Mn metal centres have been synthesised and intercalated into Zn/Al layered double hydroxide hosts and used as catalyst for the epoxidation of cyclohexene, dicyclopentadiene and 1,5-cyclooctadiene. Using a combination of pivalaldehyde and molecular oxygen at atmospheric or higher pressures to produce the corresponding peracid as oxidant, cyclohexene gave two oxidation products, cyclohexene oxide and 2-cyclohexen-1-one, whereas, dicyclopentadiene was transformed exclusively into the corresponding mono-epoxide. The relative order of olefin activity correlates with the C-C=C bond angle for both metal centres. The product selectivity was found to be largely independent of the central metal ion suggesting that the local environment around the central metal ion was of greater importance. A possible mechanism-based on the product distribution is suggested. (c) 2006 Elsevier B.V. All rights reserved.

KW - chiral salen-metal compound

KW - LDH host catalyst

KW - layered double hydroxide

KW - epoxidation

KW - layered double hydroxides

KW - hydrogen-peroxide

KW - molecular-oxygen

KW - selective oxidation

KW - allylic alcohols

KW - cyclic alkenes

KW - catalysts

KW - olefins

KW - hydrotalcite

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JO - Journal of Molecular Catalysis A: Chemical

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SN - 1381-1169

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