Catalytic effect of different hydroxyl-functionalised ionic liquids together with Zn(II) complex in the synthesis of cyclic carbonates from CO2

Ana B. Paninho; Andreia Forte; Malgorzata E. Zakrzewska; Kamran T. Mahmudov; Armando J. L. Pombeiro; M. Fátima C. Guedes da Silva; Manuel  Nunes da Ponte; Luís C. Branco; Ana V. M. Nunes

doi:10.1016/j.mcat.2020.111292

Catalytic effect of different hydroxyl-functionalised ionic liquids together with Zn(II) complex in the synthesis of cyclic carbonates from CO₂

Ana B. Paninho, Andreia Forte, Malgorzata E. Zakrzewska, Kamran T. Mahmudov, Armando J. L. Pombeiro, M. Fátima C. Guedes da Silva, Manuel Nunes da Ponte, Luís C. Branco, Ana V. M. Nunes

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Abstract

Quaternary ammonium salts bearing different alkyl chains and hydroxyl groups were synthesized and tested for the first time as co-catalysts in the cycloaddition reaction between CO₂ and propylene oxide. Their synergetic catalytic effect together with the known tetranuclear zinc(II) complex [Zn₄(μ₃-OH)₂ (1κO:2κO-HL)₄(κO-HL)₂(H₂O)₄] (1), H₂L = 3-(2-carboxyphenyl-hydrazone)pentane-2,4-dione, was investigated at 60 °C and 4 MPa. Results obtained highlight the importance of exploring the hydrogen bonding effect via functionalization with hydroxyl groups but show that the length of the alkyl chains of the ammonium cation is a more relevant factor affecting the reaction kinetic for the system studied.

Original language	English
Article number	111292
Journal	Molecular Catalysis
Volume	499
DOIs	https://doi.org/10.1016/j.mcat.2020.111292
Publication status	Published - Jan 2021

Keywords

arylhydrazones of B-diketones
catalysis
CO utilization
epoxides
ionic liquids
organic carbonates
propylene carbonate

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10.1016/j.mcat.2020.111292

https://reader.elsevier.com/reader/sd/pii/S2468823120305551?token=94C09568EDF7CF2AC997275F19E9A1BBDCAAEB8A47800731C87752CE659BB469817704E07A529B645A9BB6DD1E7CAA0D&originRegion=eu-west-1&originCreation=20210407143429

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Paninho, A. B., Forte, A., Zakrzewska, M. E., Mahmudov, K. T., Pombeiro, A. J. L., da Silva, M. F. C. G., Nunes da Ponte, M., Branco, L. C., & Nunes, A. V. M. (2021). Catalytic effect of different hydroxyl-functionalised ionic liquids together with Zn(II) complex in the synthesis of cyclic carbonates from CO₂. Molecular Catalysis, 499, [111292]. https://doi.org/10.1016/j.mcat.2020.111292

Paninho, Ana B. ; Forte, Andreia ; Zakrzewska, Malgorzata E. ; Mahmudov, Kamran T. ; Pombeiro, Armando J. L. ; da Silva, M. Fátima C. Guedes ; Nunes da Ponte, Manuel ; Branco, Luís C. ; Nunes, Ana V. M. / Catalytic effect of different hydroxyl-functionalised ionic liquids together with Zn(II) complex in the synthesis of cyclic carbonates from CO₂. In: Molecular Catalysis. 2021 ; Vol. 499.

@article{ddcea665c4d2410cad5e47ed38e590e7,

title = "Catalytic effect of different hydroxyl-functionalised ionic liquids together with Zn(II) complex in the synthesis of cyclic carbonates from CO2",

abstract = "Quaternary ammonium salts bearing different alkyl chains and hydroxyl groups were synthesized and tested for the first time as co-catalysts in the cycloaddition reaction between CO2 and propylene oxide. Their synergetic catalytic effect together with the known tetranuclear zinc(II) complex [Zn4(μ3-OH)2 (1κO:2κO-HL)4(κO-HL)2(H2O)4] (1), H2L = 3-(2-carboxyphenyl-hydrazone)pentane-2,4-dione, was investigated at 60 °C and 4 MPa. Results obtained highlight the importance of exploring the hydrogen bonding effect via functionalization with hydroxyl groups but show that the length of the alkyl chains of the ammonium cation is a more relevant factor affecting the reaction kinetic for the system studied.",

keywords = "arylhydrazones of B-diketones, catalysis, CO utilization, epoxides, ionic liquids, organic carbonates, propylene carbonate",

author = "Paninho, {Ana B.} and Andreia Forte and Zakrzewska, {Malgorzata E.} and Mahmudov, {Kamran T.} and Pombeiro, {Armando J. L.} and {da Silva}, {M. F{\'a}tima C. Guedes} and {Nunes da Ponte}, Manuel and Branco, {Lu{\'i}s C.} and Nunes, {Ana V. M.}",

note = "This work was supported by Fundacao para a Ciencia e Tecnologia FCT/MCTESprojects PTDC/EQU-EPQ/31926/2017, UIDB/50006/2020 of the Associate Laboratory for Green Chemistry - LAQV, and UIDB/00100/2020 of the Centro de Quimica Estrutural - CQE. The authors also thanks to the project {"}SunStorage: Harvesting and storage of solar energy{"}, with reference POCI-01-0145-FEDER-016387, funded by European Regional Development Fund (ERDF), through COMPETE 2020Operational Programme for Competitiveness and Internationalisation (OPCI). A.V.M. Nunes is thankful to FCT/MCTES for contract IF/01374/2014. K.T. Mahmudov acknowledges the FCT/MCTES and IST for DL 57/2016 and L 57/2017 Program and for contract IST-ID/85/2018. M.E. Zakrzewska is thankful to FCT/MCTES for the postdoctoral grant SFRH/BPD/122655/2016. The NMR spectrometers at FCT NOVA are part of Rede Nacional de RMN (PTNMR), supported by FCT/MCTES through ROTEIRO/0031/2013 -PINFRA/22161/2016 and co-financed by FEDER through COMPETE 2020, POCI, and PORL and FCT through PIDDAC.",

year = "2021",

month = jan,

doi = "10.1016/j.mcat.2020.111292",

language = "English",

volume = "499",

journal = "Molecular Catalysis",

issn = "2468-8231",

publisher = "Elsevier BV",

}

Catalytic effect of different hydroxyl-functionalised ionic liquids together with Zn(II) complex in the synthesis of cyclic carbonates from CO₂. / Paninho, Ana B.; Forte, Andreia ; Zakrzewska, Malgorzata E.; Mahmudov, Kamran T.; Pombeiro, Armando J. L.; da Silva, M. Fátima C. Guedes; Nunes da Ponte, Manuel ; Branco, Luís C.; Nunes, Ana V. M.

In: Molecular Catalysis, Vol. 499, 111292, 01.2021.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Catalytic effect of different hydroxyl-functionalised ionic liquids together with Zn(II) complex in the synthesis of cyclic carbonates from CO2

AU - Paninho, Ana B.

AU - Forte, Andreia

AU - Zakrzewska, Malgorzata E.

AU - Mahmudov, Kamran T.

AU - Pombeiro, Armando J. L.

AU - da Silva, M. Fátima C. Guedes

AU - Nunes da Ponte, Manuel

AU - Branco, Luís C.

AU - Nunes, Ana V. M.

N1 - This work was supported by Fundacao para a Ciencia e Tecnologia FCT/MCTESprojects PTDC/EQU-EPQ/31926/2017, UIDB/50006/2020 of the Associate Laboratory for Green Chemistry - LAQV, and UIDB/00100/2020 of the Centro de Quimica Estrutural - CQE. The authors also thanks to the project "SunStorage: Harvesting and storage of solar energy", with reference POCI-01-0145-FEDER-016387, funded by European Regional Development Fund (ERDF), through COMPETE 2020Operational Programme for Competitiveness and Internationalisation (OPCI). A.V.M. Nunes is thankful to FCT/MCTES for contract IF/01374/2014. K.T. Mahmudov acknowledges the FCT/MCTES and IST for DL 57/2016 and L 57/2017 Program and for contract IST-ID/85/2018. M.E. Zakrzewska is thankful to FCT/MCTES for the postdoctoral grant SFRH/BPD/122655/2016. The NMR spectrometers at FCT NOVA are part of Rede Nacional de RMN (PTNMR), supported by FCT/MCTES through ROTEIRO/0031/2013 -PINFRA/22161/2016 and co-financed by FEDER through COMPETE 2020, POCI, and PORL and FCT through PIDDAC.

PY - 2021/1

Y1 - 2021/1

N2 - Quaternary ammonium salts bearing different alkyl chains and hydroxyl groups were synthesized and tested for the first time as co-catalysts in the cycloaddition reaction between CO2 and propylene oxide. Their synergetic catalytic effect together with the known tetranuclear zinc(II) complex [Zn4(μ3-OH)2 (1κO:2κO-HL)4(κO-HL)2(H2O)4] (1), H2L = 3-(2-carboxyphenyl-hydrazone)pentane-2,4-dione, was investigated at 60 °C and 4 MPa. Results obtained highlight the importance of exploring the hydrogen bonding effect via functionalization with hydroxyl groups but show that the length of the alkyl chains of the ammonium cation is a more relevant factor affecting the reaction kinetic for the system studied.

AB - Quaternary ammonium salts bearing different alkyl chains and hydroxyl groups were synthesized and tested for the first time as co-catalysts in the cycloaddition reaction between CO2 and propylene oxide. Their synergetic catalytic effect together with the known tetranuclear zinc(II) complex [Zn4(μ3-OH)2 (1κO:2κO-HL)4(κO-HL)2(H2O)4] (1), H2L = 3-(2-carboxyphenyl-hydrazone)pentane-2,4-dione, was investigated at 60 °C and 4 MPa. Results obtained highlight the importance of exploring the hydrogen bonding effect via functionalization with hydroxyl groups but show that the length of the alkyl chains of the ammonium cation is a more relevant factor affecting the reaction kinetic for the system studied.

KW - arylhydrazones of B-diketones

KW - catalysis

KW - CO utilization

KW - epoxides

KW - ionic liquids

KW - organic carbonates

KW - propylene carbonate

UR - http://www.scopus.com/inward/record.url?scp=85097110685&partnerID=8YFLogxK

U2 - 10.1016/j.mcat.2020.111292

DO - 10.1016/j.mcat.2020.111292

M3 - Article

AN - SCOPUS:85097110685

VL - 499

JO - Molecular Catalysis

JF - Molecular Catalysis

SN - 2468-8231

M1 - 111292

ER -

Catalytic effect of different hydroxyl-functionalised ionic liquids together with Zn(II) complex in the synthesis of cyclic carbonates from CO₂

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