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Discovery and optimization of rapid manganese catalysts for the epoxidation of terminal olefins

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Title: Discovery and optimization of rapid manganese catalysts for the epoxidation of terminal olefins
Authors: Murphy, Andrew1, Stack, T. Daniel P. stack@stanford.edu
Source: Journal of Molecular Catalysis A: Chemistry. May2006, Vol. 251 Issue 1/2, p78-88. 11p.
Subjects: Manganese catalysts, Alkenes, Epoxy compounds, Peracetic acid
Abstract: Abstract: Twenty-two MnII complexes were screened for the catalytic epoxidation of terminal olefins using peracetic acid as the oxidant. A limited number of these complexes are efficient catalysts using peracetic acid solutions generated with H2SO4 (PAAC), but most complexes are effective at 1mol% catalyst loading using peracetic acid generated with strongly acidic resins (PAAR). Under the less acidic conditions of PAAR, [MnII(phen)2(CF3SO3)2] has the highest activity of the catalysts screened, and epoxides terminal olefins using as little as 0.02mol% catalyst within 5min. The dimeric species [MnIII,IV 2(phen)4(O)2](ClO4)3 is also a viable epoxidation catalyst with PAAR, but the dimeric species is reduced by the residual H2O2 to monomeric MnII species under the reaction conditions. By comparison, a similar dimeric complex [MnIII,IV 2(R,R-mcp)2(O)2](ClO4)3, is not reduced by H2O2 under the reaction conditions and is not catalytically active, supportive of the notion that the catalytically relevant species is monomeric. [Copyright &y& Elsevier]
Copyright of Journal of Molecular Catalysis A: Chemistry is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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  Data: Discovery and optimization of rapid manganese catalysts for the epoxidation of terminal olefins
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  Data: <searchLink fieldCode="AR" term="%22Murphy%2C+Andrew%22">Murphy, Andrew</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Stack%2C+T%2E+Daniel+P%2E%22">Stack, T. Daniel P.</searchLink><i> stack@stanford.edu</i>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Molecular+Catalysis+A%3A+Chemistry%22">Journal of Molecular Catalysis A: Chemistry</searchLink>. May2006, Vol. 251 Issue 1/2, p78-88. 11p.
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  Data: <searchLink fieldCode="DE" term="%22Manganese+catalysts%22">Manganese catalysts</searchLink><br /><searchLink fieldCode="DE" term="%22Alkenes%22">Alkenes</searchLink><br /><searchLink fieldCode="DE" term="%22Epoxy+compounds%22">Epoxy compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Peracetic+acid%22">Peracetic acid</searchLink>
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  Data: Abstract: Twenty-two MnII complexes were screened for the catalytic epoxidation of terminal olefins using peracetic acid as the oxidant. A limited number of these complexes are efficient catalysts using peracetic acid solutions generated with H2SO4 (PAAC), but most complexes are effective at 1mol% catalyst loading using peracetic acid generated with strongly acidic resins (PAAR). Under the less acidic conditions of PAAR, [MnII(phen)2(CF3SO3)2] has the highest activity of the catalysts screened, and epoxides terminal olefins using as little as 0.02mol% catalyst within 5min. The dimeric species [MnIII,IV 2(phen)4(O)2](ClO4)3 is also a viable epoxidation catalyst with PAAR, but the dimeric species is reduced by the residual H2O2 to monomeric MnII species under the reaction conditions. By comparison, a similar dimeric complex [MnIII,IV 2(R,R-mcp)2(O)2](ClO4)3, is not reduced by H2O2 under the reaction conditions and is not catalytically active, supportive of the notion that the catalytically relevant species is monomeric. [Copyright &y& Elsevier]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Journal of Molecular Catalysis A: Chemistry is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1016/j.molcata.2006.01.042
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      – Code: eng
        Text: English
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      – SubjectFull: Manganese catalysts
        Type: general
      – SubjectFull: Alkenes
        Type: general
      – SubjectFull: Epoxy compounds
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      – SubjectFull: Peracetic acid
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      – TitleFull: Discovery and optimization of rapid manganese catalysts for the epoxidation of terminal olefins
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              Text: May2006
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