Citation: Jin-Fa YU, Min-Jie MAO, Hui-Ping LI, Xian-Bo ZHOU, Dan-Dan ZHANG, Jian-Xin CHEN, Zhi-Chun ZHANG. Synthesis, Characterization and Catalytic Activity of SalenCo(III)Cl in Alternating Copolymerization of CO₂ and Propylene Oxide[J]. Chinese Journal of Structural Chemistry, ;2020, 39(1): 86-95. doi: 10.14102/j.cnki.0254-5861.2011-2352 shu

Synthesis, Characterization and Catalytic Activity of SalenCo(III)Cl in Alternating Copolymerization of CO₂ and Propylene Oxide

a.
College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350007, China
b.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China

Corresponding author: Jian-Xin CHEN, jxchen_1964@163.com
Received Date: 4 March 2019
Accepted Date: 11 April 2019

Fund Project: the Natural Science Foundation of Fujian Province 2010J01026the Ministry of Education of China 208066the Education Department of Fujian Province JA07029the State Key Laboratory of Structural Chemistry 20130013

Figures(12)

The title complex SalenCo(III)Cl (Salen = 6, 6'-((1E, 1'E)-(cyclohexane-1, 2-diylbis(azaneylylidene))bis(methaneylylidene))bis(2, 4-di-tert-butylphenol)) was synthesized and characterized by elemental analysis, IR spectroscopy, ¹H NMR and UV-Vis. The complex can be used as catalyst for the propylene oxide (PO)/CO₂ copolymerization in different conditions of reaction time, reaction temperature, carbon dioxide pressure and monomer concentration, and the optimum conditions for copolymerization were obtained.
- cobalt(III) complex,
- salen,
- ploy(propylene carbonate),
- catalytic activity
References
1. [1]
  Firouz, A. Q.; Torabi, F. Utilization of carbon dioxide and methane in huff- and -puff injection scheme to improve heavy oil recovery. Fuel 2014, 117, 966-973. doi: 10.1016/j.fuel.2013.10.040
2. [2]
  Perathoner, S.; Centi, G. CO₂ recycling: a key strategy to introduce green energy in the chemical production chain. ChemSusChem. 2014, 7, 1274-1282. doi: 10.1002/cssc.201300926
3. [3]
  Chen, Q.; Lv, M.; Tang, Z. Y.; Wang, H.; Wei, W.; Sun, Y. H. Opportunities of integrated systems with CO₂, utilization technologies for green fuel & chemicals production in a carbon-constrained society. J. CO₂. Util. 2016, 14, 1-9. doi: 10.1016/j.jcou.2016.01.004
4. [4]
  Darensbourg, D. J.; Mackiewicz, R. M.; Phelps, A. L.; Damon, R. B. Copolymerization of CO₂ and epoxides catalyzed by metal salen complexes. Acc. Chem. Res. 2004, 37, 836-844. doi: 10.1021/ar030240u
5. [5]
  Eberhardt, R.; Allmendinger, M.; Rieger, B. DMAP/Cr(III) catalyst ratio: the decisive factor for poly(propylene carbonate) formation in the coupling of CO₂ and propylene oxide. Macromol. Rapid. Commun. 2010, 24, 194-196.
6. [6]
  Rulev, Y. A.; Gugkaeva, Z.; Maleev, V. I.; Belokon, Y. N.; North, M. Robust bifunctional aluminium-salen catalysts for the preparation of cyclic carbonates from carbon dioxide and epoxides. Beilstein. J. Org. Chem. 2015, 11, 1614-1623. doi: 10.3762/bjoc.11.176
7. [7]
  Niu, Y. S.; Li, H. C. Silica supported Schiff-base cobalt(III) complex-Lewis base system: a highly selective catalyst for alternating copolymerization of CO₂ and propylene oxide. E-Polymers 2011, 11, 55-62.
8. [8]
  Darensbourg, D. J.; Yeung, A. D. Kinetics of the (salen)Cr(III) and (salen)Co(III) catalyzed copolymerization of epoxides with CO₂, and of the accompanying degradation reactions. Poly. Chem. -UK. 2015, 6, 1103-1117. doi: 10.1039/C4PY01322K
9. [9]
  Jacobsen, E. N. Asymmetric catalysis of epoxide ring-opening reactions. Acc. Chem. Res. 2000, 33, 421-431. doi: 10.1021/ar960061v
10. [10]
  Liu, T. T.; Liang, J.; Xu, R.; Huang, Y. B.; Cao, R. Salen-Co(III) insertion in multivariate cationic metal-organic frameworks for the enhanced cycloaddition reaction of carbon dioxide. Chem. Commun. 2019, DOI: 10.1039/c8cc10268f.
11. [11]
  Qin, Z.; Thomas, C. M.; Lee, S.; Coates, G. W. Cobalt-based complexes for the copolymerization of propylene oxide and CO₂: active and selective catalysts for polycarbonate synthesis. Angew. Chem. Int. Ed. 2003, 42, 5484-5487. doi: 10.1002/anie.200352605
12. [12]
  Darensbourg, D. J. Making plastics from carbon dioxide: salen metal complexes as catalysts for the production of polycarbonates from epoxides and CO₂. Chem. Rev. 2007, 38, 2388-2410.
13. [13]
  Lednor, P. W.; Rol, N. C. Copolymerization of propene oxide with carbon dioxide: a selective incorporation of propene oxide into the polycarbonate chains, determined by 100 MHz ¹³C NMR spectroscopy. J. Chem. Soc. Chem. Commun. 1985, 9, 598-599.
14. [14]
  Lu, B. Y.; Gao, Y. H.; Zhao, X.; Yan, W. D.; Wang, X. H. Alternating copolymerization of carbon dioxide and propylene oxide under bifunctional cobalt salen complexes: role of Lewis base substituent covalent bonded on salen ligand. J. Polym. Sci. Pol. Chem. 2010, 48, 359-365. doi: 10.1002/pola.23792
15. [15]
  Decortes, A.; Haak, R. M.; Martin, C.; Martin, E.; Belmonte, M. M.; Kleij, A. Copolymerization of CO₂ and cyclohexene oxide mediated by Yb(salen)-based complexes. Macromolecules 2015, 48, 8197-8207. doi: 10.1021/acs.macromol.5b01880
16. [16]
  Kember, M. R.; Buchard, A.; Williams, C. K. Catalysts for CO₂/epoxide copolymerisation. Chem. Commun. 2011, 47, 141-163. doi: 10.1039/C0CC02207A
1. [1]
  Firouz, A. Q.; Torabi, F. Utilization of carbon dioxide and methane in huff- and -puff injection scheme to improve heavy oil recovery. Fuel 2014, 117, 966-973. doi: 10.1016/j.fuel.2013.10.040
2. [2]
  Perathoner, S.; Centi, G. CO₂ recycling: a key strategy to introduce green energy in the chemical production chain. ChemSusChem. 2014, 7, 1274-1282. doi: 10.1002/cssc.201300926
3. [3]
  Chen, Q.; Lv, M.; Tang, Z. Y.; Wang, H.; Wei, W.; Sun, Y. H. Opportunities of integrated systems with CO₂, utilization technologies for green fuel & chemicals production in a carbon-constrained society. J. CO₂. Util. 2016, 14, 1-9. doi: 10.1016/j.jcou.2016.01.004
4. [4]
  Darensbourg, D. J.; Mackiewicz, R. M.; Phelps, A. L.; Damon, R. B. Copolymerization of CO₂ and epoxides catalyzed by metal salen complexes. Acc. Chem. Res. 2004, 37, 836-844. doi: 10.1021/ar030240u
5. [5]
  Eberhardt, R.; Allmendinger, M.; Rieger, B. DMAP/Cr(III) catalyst ratio: the decisive factor for poly(propylene carbonate) formation in the coupling of CO₂ and propylene oxide. Macromol. Rapid. Commun. 2010, 24, 194-196.
6. [6]
  Rulev, Y. A.; Gugkaeva, Z.; Maleev, V. I.; Belokon, Y. N.; North, M. Robust bifunctional aluminium-salen catalysts for the preparation of cyclic carbonates from carbon dioxide and epoxides. Beilstein. J. Org. Chem. 2015, 11, 1614-1623. doi: 10.3762/bjoc.11.176
7. [7]
  Niu, Y. S.; Li, H. C. Silica supported Schiff-base cobalt(III) complex-Lewis base system: a highly selective catalyst for alternating copolymerization of CO₂ and propylene oxide. E-Polymers 2011, 11, 55-62.
8. [8]
  Darensbourg, D. J.; Yeung, A. D. Kinetics of the (salen)Cr(III) and (salen)Co(III) catalyzed copolymerization of epoxides with CO₂, and of the accompanying degradation reactions. Poly. Chem. -UK. 2015, 6, 1103-1117. doi: 10.1039/C4PY01322K
9. [9]
  Jacobsen, E. N. Asymmetric catalysis of epoxide ring-opening reactions. Acc. Chem. Res. 2000, 33, 421-431. doi: 10.1021/ar960061v
10. [10]
  Liu, T. T.; Liang, J.; Xu, R.; Huang, Y. B.; Cao, R. Salen-Co(III) insertion in multivariate cationic metal-organic frameworks for the enhanced cycloaddition reaction of carbon dioxide. Chem. Commun. 2019, DOI: 10.1039/c8cc10268f.
11. [11]
  Qin, Z.; Thomas, C. M.; Lee, S.; Coates, G. W. Cobalt-based complexes for the copolymerization of propylene oxide and CO₂: active and selective catalysts for polycarbonate synthesis. Angew. Chem. Int. Ed. 2003, 42, 5484-5487. doi: 10.1002/anie.200352605
12. [12]
  Darensbourg, D. J. Making plastics from carbon dioxide: salen metal complexes as catalysts for the production of polycarbonates from epoxides and CO₂. Chem. Rev. 2007, 38, 2388-2410.
13. [13]
  Lednor, P. W.; Rol, N. C. Copolymerization of propene oxide with carbon dioxide: a selective incorporation of propene oxide into the polycarbonate chains, determined by 100 MHz ¹³C NMR spectroscopy. J. Chem. Soc. Chem. Commun. 1985, 9, 598-599.
14. [14]
  Lu, B. Y.; Gao, Y. H.; Zhao, X.; Yan, W. D.; Wang, X. H. Alternating copolymerization of carbon dioxide and propylene oxide under bifunctional cobalt salen complexes: role of Lewis base substituent covalent bonded on salen ligand. J. Polym. Sci. Pol. Chem. 2010, 48, 359-365. doi: 10.1002/pola.23792
15. [15]
  Decortes, A.; Haak, R. M.; Martin, C.; Martin, E.; Belmonte, M. M.; Kleij, A. Copolymerization of CO₂ and cyclohexene oxide mediated by Yb(salen)-based complexes. Macromolecules 2015, 48, 8197-8207. doi: 10.1021/acs.macromol.5b01880
16. [16]
  Kember, M. R.; Buchard, A.; Williams, C. K. Catalysts for CO₂/epoxide copolymerisation. Chem. Commun. 2011, 47, 141-163. doi: 10.1039/C0CC02207A
1. [1]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
2. [2]
  Qiaojia GUO , Junkai CAI , Chunying DUAN . Effects of anions on the structural regulation of Zn-salen-modified metal-organic cage. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2203-2211. doi: 10.11862/CJIC.20240209
3. [3]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
4. [4]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
5. [5]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
6. [6]
  Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
7. [7]
  Minghui Zhang , Na Zhang , Qian Zhao , Chao Wang , Alexander Steiner , Jianliang Xiao , Weijun Tang . Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines. Chinese Chemical Letters, 2025, 36(4): 110081-. doi: 10.1016/j.cclet.2024.110081
8. [8]
  Juan Yuan , Bin Zhang , Jinping Wu , Mengfan Wang . Design of a Comprehensive Experiment on Preparation and Characterization of Cu₂(Salen)₂ Nanomaterials with Two Distinct Morphologies. University Chemistry, 2024, 39(10): 420-425. doi: 10.3866/PKU.DXHX202402014
9. [9]
  Peng Zhang , Yitao Yang , Tian Qin , Xueqiu Wu , Yuechang Wei , Jing Xiong , Xi Liu , Yu Wang , Zhen Zhao , Jinqing Jiao , Liwei Chen . Interface engineering of Pt/CeO₂-{100} catalysts for enhancing catalytic activity in auto-exhaust carbon particles oxidation. Chinese Chemical Letters, 2025, 36(2): 110396-. doi: 10.1016/j.cclet.2024.110396
10. [10]
  Panpan Wang , Hongbao Fang , Mengmeng Wang , Guandong Zhang , Na Xu , Yan Su , Hongke Liu , Zhi Su . A mitochondria targeting Ir(III) complex triggers ferroptosis and autophagy for cancer therapy: A case of aggregation enhanced PDT strategy for metal complexes. Chinese Chemical Letters, 2025, 36(1): 110099-. doi: 10.1016/j.cclet.2024.110099
11. [11]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
12. [12]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
13. [13]
  Ruiying Liu , Li Zhao , Baishan Liu , Jiayuan Yu , Yujie Wang , Wanqiang Yu , Di Xin , Chaoqiong Fang , Xuchuan Jiang , Riming Hu , Hong Liu , Weijia Zhou . Modulating pollutant adsorption and peroxymonosulfate activation sites on Co3O4@N,O doped-carbon shell for boosting catalytic degradation activity. Chinese Journal of Structural Chemistry, 2024, 43(8): 100332-100332. doi: 10.1016/j.cjsc.2024.100332
14. [14]
  Yang Yang , Jing-Li Luo , Xian-Zhu Fu . Water-oxidation intermediates enabling electrochemical propylene epoxidation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100269-100269. doi: 10.1016/j.cjsc.2024.100269
15. [15]
  Xinyu Liu , Jialin Yang , Zonglin He , Jiaoyan Ai , Lina Song , Baohua Liu . Linear polyurethanes with excellent comprehensive properties from poly(ethylene carbonate) diol. Chinese Chemical Letters, 2025, 36(1): 110236-. doi: 10.1016/j.cclet.2024.110236
16. [16]
  Jun Zhang , Zhiyao Zheng , Can Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160
17. [17]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
18. [18]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
19. [19]
  Lu-Lu He , Lan-Tu Xiong , Xin Wang , Yu-Zhen Li , Jia-Bao Li , Yu Shi , Xin Deng , Zi-Ning Cui . Application of inhibitors targeting the type III secretion system in phytopathogenic bacteria. Chinese Chemical Letters, 2025, 36(4): 110044-. doi: 10.1016/j.cclet.2024.110044
20. [20]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(324)
HTML views(24)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis, Characterization and Catalytic Activity of SalenCo(III)Cl in Alternating Copolymerization of CO2 and Propylene Oxide

References

Metrics

通讯作者: 陈斌, bchen63@163.com

Synthesis, Characterization and Catalytic Activity of SalenCo(III)Cl in Alternating Copolymerization of CO₂ and Propylene Oxide