1,2-Cyclohexanediamine, N,N'-bis(2-pyridinylmethylene)-

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CAS: 907179-34-4
MF: C18H20N4
MW: 292.3782
Synonyms: 1,2-Cyclohexanediamine, N,N'-bis(2-pyridinylmethylene)-

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Xianhong Wang

Chinese Academy of Sciences
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Yusheng Qin

Chinese Academy of Sciences
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Co-reporter: Xingfeng Sheng, Lijun Qiao, Yusheng Qin, Xianhong Wang, Fosong Wang
pp: 129-133
Publication Date(Web):28 May 2014
DOI: 10.1016/j.poly.2014.02.047
The novel iron complexes [N,N′-bis-2-pyridinylmethylene-cyclohexane-1,2- diamine]iron(II) chloride (1) and [N,N′-bis-2-pyridinylmethyl-cyclohexane-1,2-diamine]iron(II) chloride (2) were designed, and they showed excellent activity for the coupling reaction epoxides and CO2 to generate the corresponding cyclic carbonates. When complex 2 was used alone as a catalyst for the cycloaddition of propylene oxide (PO) and CO2, the PO conversion was 95% at 130 °C and 4 MPa CO2 pressure in 4 h. Once a co-catalyst like tetrabutylammonium bromide (TBAB) was added, the conversion could reach 100% with nearly 100% selectivity for propylene carbonate (PC), with a turnover number (TON) of 1000 at 100 °C and 4 MPa CO2 pressure in 6 h, i.e. the quantitative synthesis of propylene carbonate can be realized. Moreover, in combination with TBAB, the iron complex can also catalyze the cycloaddition of cyclohexene oxide (CHO) and epichlorohydrin (ECH) with CO2 to produce the corresponding cyclic carbonates, and the cyclohexene carbonate obtained was mainly the cis-isomer.Graphical abstractNovel iron complexes in combination with TBAB showed excellent activity for the coupling reaction of epoxides and CO2 to generate the corresponding cyclic carbonates.Image for unlabelled figure

Yu-Lin Yang

Harbin Institute of Technology
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Rui-Qing Fan 范瑞清

Harbin Institute of Technology
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XianHong Wang

Changchun Institute of Applied Chemistry, Chinese Academy of Sciences
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Co-reporter: Xingfeng Sheng, Lijun Qiao, Yusheng Qin, Xianhong Wang, Fosong Wang
pp: 129-133
Publication Date(Web):28 May 2014
DOI: 10.1016/j.poly.2014.02.047
The novel iron complexes [N,N′-bis-2-pyridinylmethylene-cyclohexane-1,2- diamine]iron(II) chloride (1) and [N,N′-bis-2-pyridinylmethyl-cyclohexane-1,2-diamine]iron(II) chloride (2) were designed, and they showed excellent activity for the coupling reaction epoxides and CO2 to generate the corresponding cyclic carbonates. When complex 2 was used alone as a catalyst for the cycloaddition of propylene oxide (PO) and CO2, the PO conversion was 95% at 130 °C and 4 MPa CO2 pressure in 4 h. Once a co-catalyst like tetrabutylammonium bromide (TBAB) was added, the conversion could reach 100% with nearly 100% selectivity for propylene carbonate (PC), with a turnover number (TON) of 1000 at 100 °C and 4 MPa CO2 pressure in 6 h, i.e. the quantitative synthesis of propylene carbonate can be realized. Moreover, in combination with TBAB, the iron complex can also catalyze the cycloaddition of cyclohexene oxide (CHO) and epichlorohydrin (ECH) with CO2 to produce the corresponding cyclic carbonates, and the cyclohexene carbonate obtained was mainly the cis-isomer.Graphical abstractNovel iron complexes in combination with TBAB showed excellent activity for the coupling reaction of epoxides and CO2 to generate the corresponding cyclic carbonates.Image for unlabelled figure

Yusheng Qin

Changchun Institute of Applied Chemistry
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Fosong Wang

Institute of Chemistry
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