Copper(II) complexes of arylhydrazone of 1H-indene-1,3(2H)-dione as catalysts for the oxidation of cyclohexane in ionic liquids

Gonçalo A. O. Tiago; Ana P. C. Ribeiro; M. Fátima C. Guedes da Silva; Kamran T. Mahmudov; Luís C. Branco; Armando J. L. Pombeiro

doi:10.3390/catal8120636

Copper(II) complexes of arylhydrazone of 1H-indene-1,3(2H)-dione as catalysts for the oxidation of cyclohexane in ionic liquids

Gonçalo A. O. Tiago, Ana P. C. Ribeiro, M. Fátima C. Guedes da Silva, Kamran T. Mahmudov, Luís C. Branco, Armando J. L. Pombeiro

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Abstract

The copper(II) complexes [CuL(H ₂ O) ₂ ]·H ₂ O (1) and [CuL(dea)] (2) [L = 2-(2-(1,3-dioxo-1H-inden-2(3H)-ylidene)hydrazinyl)benzenesulfonate, dea = diethanolamine] were applied as catalysts in the peroxidative (with tert-butyl-hydroperoxide or hydrogen peroxide) conversion of cyclohexane to cyclohexanol and cyclohexanone, either in acetonitrile or in any of the ionic liquids [bmim][NTf ₂ ] and [hmim][NTf ₂ ] [bmim = 1-butyl-3-methylimidazolium, hmim = 1-hexyl-3-methylimidazolium, NTf ₂ = bis(trifluoromethanesulfonyl) imide]. Tert-butyl-hydroperoxide led to better product yields, as compared to H ₂ O ₂ , with a selectivity directed towards cyclohexanone. The ILs showed a better performance than the conventional solvent for the copper complex 1. No catalytic activity was observed for 2 in the presence of an IL.

Original language	English
Article number	636
Journal	Catalysts
Volume	8
Issue number	12
DOIs	https://doi.org/10.3390/catal8120636
Publication status	Published - 1 Dec 2018

Keywords

Arylhydrazones
Catalysis
Copper
Cyclohexane oxidation
Ionic liquids

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Copper(II) complexes of arylhydrazone of 1H-indene-1,3(2H)-dioneFinal published version, 1.06 MBLicence: CC BY

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@article{89dd4b3c1e2c47259aa92d798b7a6cc2,

title = "Copper(II) complexes of arylhydrazone of 1H-indene-1,3(2H)-dione as catalysts for the oxidation of cyclohexane in ionic liquids",

abstract = " The copper(II) complexes [CuL(H 2 O) 2 ]·H 2 O (1) and [CuL(dea)] (2) [L = 2-(2-(1,3-dioxo-1H-inden-2(3H)-ylidene)hydrazinyl)benzenesulfonate, dea = diethanolamine] were applied as catalysts in the peroxidative (with tert-butyl-hydroperoxide or hydrogen peroxide) conversion of cyclohexane to cyclohexanol and cyclohexanone, either in acetonitrile or in any of the ionic liquids [bmim][NTf 2 ] and [hmim][NTf 2 ] [bmim = 1-butyl-3-methylimidazolium, hmim = 1-hexyl-3-methylimidazolium, NTf 2 = bis(trifluoromethanesulfonyl) imide]. Tert-butyl-hydroperoxide led to better product yields, as compared to H 2 O 2 , with a selectivity directed towards cyclohexanone. The ILs showed a better performance than the conventional solvent for the copper complex 1. No catalytic activity was observed for 2 in the presence of an IL. ",

keywords = "Arylhydrazones, Catalysis, Copper, Cyclohexane oxidation, Ionic liquids",

author = "Tiago, {Gon{\c c}alo A. O.} and Ribeiro, {Ana P. C.} and Silva, {M. F{\'a}tima C. Guedes da} and Mahmudov, {Kamran T.} and Branco, {Lu{\'i}s C.} and Pombeiro, {Armando J. L.}",

note = "info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F90883%2F2012/PT# This research was founded by the Foundation for Science and Technology (FCT), grant PD/BD/106015/2014. The APC was funded by SFRH/BPD/90883/2012).",

year = "2018",

month = dec,

day = "1",

doi = "10.3390/catal8120636",

language = "English",

volume = "8",

journal = "Catalysts",

issn = "2073-4344",

publisher = "MDPI - Multidisciplinary Digital Publishing Institute",

number = "12",

}

TY - JOUR

T1 - Copper(II) complexes of arylhydrazone of 1H-indene-1,3(2H)-dione as catalysts for the oxidation of cyclohexane in ionic liquids

AU - Tiago, Gonçalo A. O.

AU - Ribeiro, Ana P. C.

AU - Silva, M. Fátima C. Guedes da

AU - Mahmudov, Kamran T.

AU - Branco, Luís C.

AU - Pombeiro, Armando J. L.

N1 - info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F90883%2F2012/PT# This research was founded by the Foundation for Science and Technology (FCT), grant PD/BD/106015/2014. The APC was funded by SFRH/BPD/90883/2012).

PY - 2018/12/1

Y1 - 2018/12/1

N2 - The copper(II) complexes [CuL(H 2 O) 2 ]·H 2 O (1) and [CuL(dea)] (2) [L = 2-(2-(1,3-dioxo-1H-inden-2(3H)-ylidene)hydrazinyl)benzenesulfonate, dea = diethanolamine] were applied as catalysts in the peroxidative (with tert-butyl-hydroperoxide or hydrogen peroxide) conversion of cyclohexane to cyclohexanol and cyclohexanone, either in acetonitrile or in any of the ionic liquids [bmim][NTf 2 ] and [hmim][NTf 2 ] [bmim = 1-butyl-3-methylimidazolium, hmim = 1-hexyl-3-methylimidazolium, NTf 2 = bis(trifluoromethanesulfonyl) imide]. Tert-butyl-hydroperoxide led to better product yields, as compared to H 2 O 2 , with a selectivity directed towards cyclohexanone. The ILs showed a better performance than the conventional solvent for the copper complex 1. No catalytic activity was observed for 2 in the presence of an IL.

AB - The copper(II) complexes [CuL(H 2 O) 2 ]·H 2 O (1) and [CuL(dea)] (2) [L = 2-(2-(1,3-dioxo-1H-inden-2(3H)-ylidene)hydrazinyl)benzenesulfonate, dea = diethanolamine] were applied as catalysts in the peroxidative (with tert-butyl-hydroperoxide or hydrogen peroxide) conversion of cyclohexane to cyclohexanol and cyclohexanone, either in acetonitrile or in any of the ionic liquids [bmim][NTf 2 ] and [hmim][NTf 2 ] [bmim = 1-butyl-3-methylimidazolium, hmim = 1-hexyl-3-methylimidazolium, NTf 2 = bis(trifluoromethanesulfonyl) imide]. Tert-butyl-hydroperoxide led to better product yields, as compared to H 2 O 2 , with a selectivity directed towards cyclohexanone. The ILs showed a better performance than the conventional solvent for the copper complex 1. No catalytic activity was observed for 2 in the presence of an IL.

KW - Arylhydrazones

KW - Catalysis

KW - Copper

KW - Cyclohexane oxidation

KW - Ionic liquids

UR - http://www.scopus.com/inward/record.url?scp=85062559947&partnerID=8YFLogxK

U2 - 10.3390/catal8120636

DO - 10.3390/catal8120636

M3 - Article

AN - SCOPUS:85062559947

SN - 2073-4344

VL - 8

JO - Catalysts

JF - Catalysts

IS - 12

M1 - 636

ER -

Copper(II) complexes of arylhydrazone of 1H-indene-1,3(2H)-dione as catalysts for the oxidation of cyclohexane in ionic liquids

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