One-pot synthesis of 3D-ZIF-7 supported on 2D-Zn–Benzimidazole– Acetate and its catalytic activity in the methoxycarbonylation of aniline with dimethyl carbonate

다국어 초록 (Multilingual Abstract)

For thefirst time, three-dimensional Zeolitic Imidazole Framework (3D) ZIF-7 (Zn(BeIM)2, BeIM= benzimidazole) supported on two-dimensional (2D) Zn(BeIM)OAc (Zinc–Benzimidazole–Acetate) wassynthesized by reacting Zn(OAc)2 and benzimidazole in a one-pot reaction. By modulating the amount ofdiethylamine during the reaction, the ZIF-7/Zn(BeIM)OAc with a 1 to 1 molar ratio was obtained when thereactant molar ratio of Zn(OAc)2 and benzimidazole was 1 to 1.5. It was found that 3D-ZIF-7 wassynthesizedfirst and then transformed into 2D-Zn(BeIM)OAc by the reaction with remaining Zn(OAc)2.
The synthesized ZIF-7 (Zn(BeIM)2) supported on Zn(BeIM)OAc (1/1) showed enhanced catalyticperformance in the methoxycarbonylation of aniline with dimethyl carbonate. The yield of methylN-phenyl carbamate reached 92.0% in 2 h at 190 C, which was higher than yields obtained using thesingle component catalysts ZIF-7 (69.9%) and Zn(BeIM)OAc (35.4%). Furthermore, this catalyst wassuccessfully reused four times, maintaining an MPC yield of 92.0%–95.8%.

참고문헌 (Reference)

1 S. Wang, 46 (46): 6858-, 2007

2 Sergio Rojas-Buzo, "Zr-MOF-808@MCM-41 catalyzed phosgene-free synthesis of polyurethane precursors" Royal Society of Chemistry (RSC) 9 (9): 146-156, 2019

3 Bibimaryam Mousavi, "Zeolitic imidazole framework-67 as an efficient heterogeneous catalyst for the conversion of CO2 to cyclic carbonates" Royal Society of Chemistry (RSC) 40 (40): 5170-5176, 2016

4 Chun-Yi Sun, "Zeolitic imidazolate framework-8 as efficient pH-sensitive drug delivery vehicle" Royal Society of Chemistry (RSC) 41 (41): 6906-, 2012

5 Xi Zhou, "Zeolitic imidazolate framework as efficient heterogeneous catalyst for the synthesis of ethyl methyl carbonate" Elsevier BV 366 : 43-47, 2013

6 Brian R. Pimentel, "Zeolitic Imidazolate Frameworks: Next-Generation Materials for Energy-Efficient Gas Separations" Wiley 7 (7): 3202-3240, 2014

7 Yu-Ri Lee, "ZIF-8: A comparison of synthesis methods" Elsevier BV 271 : 276-280, 2015

8 Sebastian C. Junggeburth, "Ultrathin 2D Coordination Polymer Nanosheets by Surfactant-Mediated Synthesis" American Chemical Society (ACS) 135 (135): 6157-6164, 2013

9 Ming He, "Toluene-assisted synthesis of RHO-type zeolitic imidazolate frameworks: synthesis and formation mechanism of ZIF-11 and ZIF-12" Royal Society of Chemistry (RSC) 42 (42): 16608-, 2013

10 Wanxi Cai, "Thermal Structural Transitions and Carbon Dioxide Adsorption Properties of Zeolitic Imidazolate Framework-7 (ZIF-7)" American Chemical Society (ACS) 136 (136): 7961-7971, 2014

11 Maarten Goesten, "The Molecular Pathway to ZIF-7 Microrods Revealed by In Situ Time-Resolved Small- and Wide-Angle X-Ray Scattering, Quick-Scanning Extended X-Ray Absorption Spectroscopy, and DFT Calculations" Wiley 19 (19): 7809-7816, 2013

12 Fang Li, "The Induction Period and Novel Active Species in Zn(OAc)2 Catalyzed Synthesis of Aromatic Carbamates" Springer Science and Business Media LLC 147 (147): 1478-1484, 2017

13 Pietro Tundo, "The Chemistry of Dimethyl Carbonate" American Chemical Society (ACS) 35 (35): 706-716, 2002

14 Zi-Hua Fu, "Synthesis of methyl N-phenyl carbamate by methoxycarbonylation of aniline with dimethyl carbonate using Pb compounds as catalysts" Elsevier BV 91 (91): 399-405, 1994

15 Ming He, "Synthesis of Zeolitic Imidazolate Framework-7 in a Water/Ethanol Mixture and Its Ethanol-Induced Reversible Phase Transition" Wiley 78 (78): 1222-1225, 2013

16 Fang Li, "Synthesis of Methyl N-Phenyl Carbamate from Aniline and Dimethyl Carbonate over Supported Zirconia Catalyst" American Chemical Society (ACS) 45 (45): 4892-4897, 2006

17 Xinqiang Zhao, "Synthesis of MDI from Dimethyl Carbonate over Solid Catalysts" American Chemical Society (ACS) 41 (41): 5139-5144, 2002

18 Xiang Wang, "Rapid and Cost-Effective Synthesis of Nanosized Zeolitic Imidazolate Framework-7 withN,N′-Dimethylformamide as Solvent and Metal Acetate Salt as Metal Source" Wiley 79 (79): 907-913, 2014

19 Xiu-Mei Li, "Poly[μ2-acetato-μ2-benzimidazolato-zinc(II)]" International Union of Crystallography (IUCr) 63 (63): m1984-m1984, 2007

20 Sandra Grego, "Phosgene-free carbamoylation of aniline via dimethyl carbonate" Walter de Gruyter GmbH 84 (84): 695-705, 2011

21 Aisheng Huang, "Organosilica-Functionalized Zeolitic Imidazolate Framework ZIF-90 Membrane with High Gas-Separation Performance" Wiley 51 (51): 10551-10555, 2012

22 Nishita Lucas, "Non-phosgene route for the synthesis of methyl phenyl carbamate using ordered AlSBA-15 catalyst" Elsevier BV 295 (295): 29-33, 2008

23 Min Kang, "Methyl N-phenyl carbamate synthesis over Zn/Al/Ce mixed oxide derived from hydrotalcite-like precursors" Royal Society of Chemistry (RSC) 9 (9): 42474-42480, 2019

24 Guang Lu, "Metal−Organic Frameworks as Sensors: A ZIF-8 Based Fabry−Pérot Device as a Selective Sensor for Chemical Vapors and Gases" American Chemical Society (ACS) 132 (132): 7832-7833, 2010

25 Fang Li, "Investigation of supported Zn(OAc)2 catalyst and its stability in N-phenyl carbamate synthesis" Elsevier BV 475 : 355-362, 2014

26 Deliana Dahnum, "Formation of defect site on ZIF-7 and its effect on the methoxycarbonylation of aniline with dimethyl carbonate" Elsevier BV 380 : 297-306, 2019

27 Lifeng Zhang, "Experimental and theoretical investigation of reaction of aniline with dimethyl carbonate catalyzed by acid–base bifunctional ionic liquids" Elsevier BV 158 (158): 279-285, 2010

28 Thanh Truong, "Expanding applications of zeolite imidazolate frameworks in catalysis: synthesis of quinazolines using ZIF-67 as an efficient heterogeneous catalyst" Royal Society of Chemistry (RSC) 5 (5): 24769-24776, 2015

29 Kyo Sung Park, "Exceptional chemical and thermal stability of zeolitic imidazolate frameworks" Proceedings of the National Academy of Sciences 103 (103): 10186-10191, 2006

30 Yi Wang, "Efficient and recyclable heterogeneous zinc alkyl carboxylate catalyst for the synthesis of N-phenyl carbamate from aniline and dimethylcarbonate" Royal Society of Chemistry (RSC) 5 (5): 109-113, 2015

31 Yichang Pan, "Effective separation of propylene/propane binary mixtures by ZIF-8 membranes" Elsevier BV 390-391 : 93-98, 2012

32 Feng Xue, "Direct Synthesis of 7 nm-Thick Zinc(II)–Benzimidazole–Acetate Metal–Organic Framework Nanosheets" American Chemical Society (ACS) 30 (30): 69-73, 2018

33 Janosch Cravillon, "Controlling Zeolitic Imidazolate Framework Nano- and Microcrystal Formation: Insight into Crystal Growth by Time-Resolved In Situ Static Light Scattering" American Chemical Society (ACS) 23 (23): 2130-2141, 2011

34 Yan-Shuo Li, "Controllable Synthesis of Metal-Organic Frameworks: From MOF Nanorods to Oriented MOF Membranes" Wiley 22 (22): 3322-3326, 2010

35 Fang Li, "Clean synthesis of methyl N-phenyl carbamate over ZnO-TiO2catalyst" Wiley 84 (84): 48-53, 2009

36 Jin Chong Tan, "Chemical structure, network topology, and porosity effects on the mechanical properties of Zeolitic Imidazolate Frameworks" Proceedings of the National Academy of Sciences 107 (107): 9938-9943, 2010

37 Toshihide Baba, "Characteristics of methoxycarbonylation of aromatic diamine with dimethyl carbonate to dicarbamate using a zinc acetate catalyst" Royal Society of Chemistry (RSC) 7 (7): 159-, 2005

38 Toshihide Baba, "Catalytic synthesis of N-alkyl carbamates by methoxycarbonylation of alkylamines with dimethyl carbonate using Pb(NO3)2" Elsevier BV 227 (227): 1-6, 2002

39 Tao Li, "Carbon dioxide selective mixed matrix composite membrane containing ZIF-7 nano-fillers" Elsevier BV 425-426 : 235-242, 2013

40 Massimo Curini, "Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis" Elsevier BV 43 (43): 4895-4897, 2002

41 Adam F. Gross, "Aqueous room temperature synthesis of cobalt and zinc sodalite zeolitic imidizolate frameworks" Royal Society of Chemistry (RSC) 41 (41): 5458-, 2012

42 Long Xiang, "Amino-Functionalized ZIF-7 Nanocrystals: Improved Intrinsic Separation Ability and Interfacial Compatibility in Mixed-Matrix Membranes for CO2 /CH4 Separation" Wiley 29 (29): 1606999-, 2017

43 Elisenda Reixach, "Alkoxycarbonylation of Industrially Relevant Anilines Using Zn4O(O2CCH3)6 as Catalyst" American Chemical Society (ACS) 51 (51): 16165-16170, 2012

44 Meipeng Jian, "Adsorptive removal of arsenic from aqueous solution by zeolitic imidazolate framework-8 (ZIF-8) nanoparticles" Elsevier BV 465 : 67-76, 2015

45 Roshith Roshan Kuruppathparambil, "A solid solution zeolitic imidazolate framework as a room temperature efficient catalyst for the chemical fixation of CO2" Royal Society of Chemistry (RSC) 18 (18): 6349-6356, 2016

46 Robin Babu, "A room temperature synthesizable zeolitic imidazolium framework catalyst for the solvent-free synthesis of cyclic carbonates" Elsevier BV 25 : 6-13, 2018