Synthesis of UiO-66-NH2Grafted Pyridineimine Cobalt Catalyst and Its Catalytic Performance in Ethylene Oligomerization

doi:10.19894/j.issn.1000-0518.210084

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (02): 258-265.DOI: 10.19894/j.issn.1000-0518.210084

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Synthesis of UiO-66-NH₂Grafted Pyridineimine Cobalt Catalyst and Its Catalytic Performance in Ethylene Oligomerization

Jing TANG, Na ZHANG(), Dong-Xu SHI, Fang-Hui ZHANG, Jian-Jie TANG

College of Chemistry& Chemical Engineering, Northeast Petroleum University, Daqing 163318, China

Received:2021-03-01 Accepted:2021-07-02 Published:2022-02-10 Online:2022-02-09
Contact: Na ZHANG
Supported by:
Heilongjiang Province College Students Innovation and Entrepreneurship Training Program(202010220044)

Abstract

Abstract:

UiO-66-NH₂grafted pyridineimine ligand was prepared by post synthetic modification with metal organic frameworks (MOFs) UiO-66-NH₂and 2-pyridinecarboxaldehyde as raw materials, and then a novel UiO-66-NH₂grafted pyridineimine cobalt catalyst was synthesized by complexation reaction with UiO-66-NH₂ grafted pyridineimine ligand and CoCl₂·6H₂O as raw materials. The structure of the products was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscope, inductively coupled plasma mass spectrometry and nitrogen adsorption-desorption, and the catalytic performance of the UiO-66-NH₂grafted pyridineimine cobalt catalyst in ethylene oligomerization was investigated. The results show that the reaction temperature, Al/Co molar ratio and ethylene pressure have a significant effect on the catalytic activity and products selectivity. The catalytic activity of 1.23×10⁵g/ (mol_Co·h) and 88.96% selectivity of butene are obtained under the condition of the reaction temperature 25℃, Al/Co molar ratio of 1000 and ethylene pressure of 1.0 MPa.

Key words: Metal organic frameworks, Ethylene oligomerization, Catalyst, Activity, Selectivity

CLC Number:

O631

Jing TANG, Na ZHANG, Dong-Xu SHI, Fang-Hui ZHANG, Jian-Jie TANG. Synthesis of UiO-66-NH₂Grafted Pyridineimine Cobalt Catalyst and Its Catalytic Performance in Ethylene Oligomerization[J]. Chinese Journal of Applied Chemistry, 2022, 39(02): 258-265.

Figures/Tables 11

References 18

[1]	SUO H Y, SOLAN G A, MA Y P, et al. Developments in compartmentalized bimetallic transition metal ethylene polymerization catalysts[J]. Coordin Chem Rev, 2018, 372:101-106.
[2]	LEE H, JOEY, PARKH. Chromiumcatalystsforethylenetrimerization/tetramerizationfunctionalizedwith ortho-fluorinated arylphosphine ligand[J]. Catal Commun, 2019, 121:15-18.
[3]	张娜, 马莉丽, 陈丽铎, 等. 超支化镍系催化剂构效关系及催化乙烯齐聚机理[J]. 化工进展, 2020, 39(2):539-547.
	ZHANG N, MA L L, CHEN L D, et al. Structure-property relationship and mechanism of catalytic ethylene oligomerization of hyperbrached nickel catalyst[J]. Chem Ind Eng Prog, 2020, 39(2):539-547.
[4]	王俊, 刘锦义, 陈丽铎, 等. 超支化双吡啶亚胺铬催化剂的合成及催化乙烯齐聚性能[J]. 应用化学, 2019, 36(7):773-781.
	WANG J, LIU J Y, CHEN L D, et al. Synthesis and ethylene oligomerization behavior of hyperbranched bispyridineimine chromium catalyst[J]. Chinese J Appl Chem, 2019, 36(7):773-781.
[5]	ALAM F, WANG J D, DONG C H, et al. Chromium (Ⅲ) catalysts based on tridentate silicon-bridged tris (diphenylphosphine) ligands for selective ethylene tri-/tetramerization[J]. J Catal, 2020, 392:278-286.
[6]	ANTONOV A A, SEMIKOLENOVA N V, TALSI E P, et al. Catalytic ethylene oligomerization on cobalt (Ⅱ) bis (imino) pyridine complexes bearing electron-withdrawing groups[J]. J Organomet Chem, 2019, 884(30):55-58.
[7]	FENG C Y, ZHOU S M, WANG D B, et al. Cooperativity in highly active ethylene dimerization by dinuclear nickel complexes bearing a bifunctional PN ligand[J]. Organometallics, 2021, 40(2):184-193.
[8]	WANG M Z, WU W, WANG X, et al. Research progress of iron-based catalysts for selective oligomerization of ethylene[J]. RSC Adv, 2020, 10(71):43640-43652.
[9]	SHIN M, SUH Y W. Ethylene oligomerization over SiO₂-Al₂O₃supported Ni₂P catalyst[J]. ChemCatChem, 2020, 12(1):135-140.
[10]	JIN F, YAN Y Z, WU G Y. Ethylene oligomerization over H-and Ni-form aluminosilicate composite with ZSM-5 and MCM-41 structure: effect of acidity strength, nickel site and porosity[J]. Catal Today, 2020, 355:148-161.
[11]	GOETJEN T A, ZHANG X, LIU J, et al. Metal-organic framework supported single site chromium (Ⅲ) catalyst for ethylene oligomerization at low pressure and temperature[J]. ACS Sustainable Chem Eng, 2019, 7(2):2553-2557.
[12]	山东明, 韩阳, 户艳平, 等. MOFs作为催化剂在乙烯选择性齐聚中的应用进展[J]. 石油化工, 2019, 48(2):203-208.
	SHAN D M, HAN Y, LU Y P, et al. Application progress of MOFs as catalysts for selective ethylene oligomerization[J]. Petrochem Technol, 2019, 48(2):203-208.
[13]	ARROZI U S F, BON V, KRAUSE S, et al. In situ imine-based linker formation for the synthesis of zirconium MOFs: a route to CO₂capture materials and ethylene oligomerization catalysts[J]. Inorg Chem, 2020, 59(1):350-359.
[14]	LIU B, JIE S Y, BU Z Y, et al. Post synthetic modifification of mixed-linker metal-organic frameworks for ethylene oligomerization[J]. RSC Adv, 2014, 4(107):62343-62346.
[15]	MADRAHIMOV S T, GALLAGHER J R, ZHANG G H, et al. Gas-phase dimerization of ethylene under mild conditions catalyzed by MOF materials containing (bpy) Ni^Ⅱcomplexes[J]. ACS Catal, 2015, 5(11):6713-6718.
[16]	PANCHENKO V N, MATROSOVA M M, JEONA J, et al. Catalytic behavior of metal-organic frameworks in the Knoevenagel condensation reaction[J]. J Catal, 2014, 316:251-259.
[17]	ZUBKEVICH S V, TUSKAEV V A, GAGIEVA S C, et al. NNNO-Heteroscorpionate nickel (Ⅱ) and cobalt (Ⅱ) complexes for ethylene oligomerization: the unprecedented formation of odd carbon number olefins[J]. Appl Organomet Chem, 2020, 34(10):5873-5887.
[18]	CHEN L D, MA L L, JIANG Y, et al. Synthesis and characterization of iron, cobalt and nickel complexes bearing para-phenylene-linked pyridine imine ligand and their catalytic properties for ethylene oligomerization[J]. Polym Bull, 2021, 78(1):415-432.

样品名称	比表面积	孔容	孔径
Sample	BET／（m²·g^－1）	Pore volume／（cm³·g^－1）	Pore size／nm
UiO-66-NH₂	1020.41	0.77	3.63
UiO-66-Pyr-Co	910.21	0.62	2.74

样品名称	比表面积	孔容	孔径
Sample	BET／（m²·g^－1）	Pore volume／（cm³·g^－1）	Pore size／nm
UiO-66-NH₂	1020.41	0.77	3.63
UiO-66-Pyr-Co	910.21	0.62	2.74

温度	活性	产物选择性
Temperature／℃	10^－5Activity／（g·mol^－1　_Co·h^－1）	Product selectivity／%
Temperature／℃	10^－5Activity／（g·mol^－1　_Co·h^－1）	C₄	C₆	C₈
15	0.36	87.42	11.59	0.99
25	0.52	90.17	8.76	1.07
35	0.47	90.89	7.95	1.16
45	0.40	92.39	7.25	0.36
55	0.29	92.52	7.00	0.48

温度	活性	产物选择性
Temperature／℃	10^－5Activity／（g·mol^－1　_Co·h^－1）	Product selectivity／%
Temperature／℃	10^－5Activity／（g·mol^－1　_Co·h^－1）	C₄	C₆	C₈
15	0.36	87.42	11.59	0.99
25	0.52	90.17	8.76	1.07
35	0.47	90.89	7.95	1.16
45	0.40	92.39	7.25	0.36
55	0.29	92.52	7.00	0.48

n（Al）／n（Co）	活性	产物选择性
	10^－5Activity／（g·mol^－1　_Co·h^－1）	Product selectivity／%
	10^－5Activity／（g·mol^－1　_Co·h^－1）	C₄	C₆	C₈
300	0.29	86.16	12.38	1.46
500	0.52	90.17	8.76	1.07
700	0.57	91.20	8.03	0.77
1000	0.81	91.62	7.99	0.39
1500	0.74	93.35	6.16	0.49

Synthesis of UiO-66-NH₂Grafted Pyridineimine Cobalt Catalyst and Its Catalytic Performance in Ethylene Oligomerization

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压力	活性	产物选择性
Pressure／MPa	10^－5Activity／（g·mol^－1　_Co·h^－1）	Product selectivity／%
Pressure／MPa	10^－5Activity／（g·mol^－1　_Co·h^－1）	C₄	C₆	C₈
0.1	0.50	93.78	6.11	0.11
0.3	0.79	91.85	8.02	0.13
0.5	0.81	91.62	7.99	0.39
0.7	0.94	89.03	9.14	1.83
1.0	1.23	88.96	9.59	1.44

循环次数	活性	产物选择性
Cycles	10^-5Activity／（g·mol^－1　_Co·h^－1）	Product selectivity／%
Cycles	10^-5Activity／（g·mol^－1　_Co·h^－1）	C₄	C₆	C₈
1	1.23	88.96	9.59	1.44
2	1.06	90.31	8.86	0.83
3	0.92	89.25	9.97	0.78
4	0.68	91.04	8.35	0.61

催化剂	活性	产物选择性
Catalyst	10^－5Activity／（g··h^－1）	Product selectivity／%
Catalyst	10^－5Activity／（g··h^－1）	C₄	C₆	C₈₊
Uio-66-Pyr-Co ^a	1.23	88.96	9.59	1.44
Pyr-Co ^b	0.20	81.67	13.11	5.22

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