Synthesis and Ethylene Oligomerization Behavior of Hyperbranched Bispyridineimine Chromium Catalyst

doi:10.11944/j.issn.1000-0518.2019.07.180401

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (7): 773-781.DOI: 10.11944/j.issn.1000-0518.2019.07.180401

• Full Papers • Previous Articles Next Articles

Synthesis and Ethylene Oligomerization Behavior of Hyperbranched Bispyridineimine Chromium Catalyst

WANG Jun^a^*(),LIU Jinyi^a,CHEN Liduo^a,LAN Tianyu^a,WANG Libo^b

^aProvincial Key Laboratory of Oil & Gas Chemical Technology, Northeast Petroleum University,Daqing,Heilongjiang 163318,China
^bDaqing Petrochemical Research Center,CNPC,Daqing,Heilongjiang 163312,China

Received:2018-12-17 Accepted:2019-03-06 Published:2019-07-01 Online:2019-07-02
Contact: WANG Jun
Supported by:
Supported by the National Key R&D Program of China(No.2017YFB0306701)

Abstract

Abstract:

A new hyperbranched bispyridineimine ligand was derived from 1.0 generation hyperbranched macromolecules and 2-chloro-4-methylpyridine through substitution reaction. Multinuclear chromium complex was synthesized from the reaction with chromium(Ⅲ) chloride tetrahydrofuran complex. The structure of hyperbranched bispyridineimine ligand and chromium complex were characterized by ultraviolet-visible spectrophotometer(UV-Vis), Fourier transform infrared spectroscopy(FT-IR), proton nuclear magnetic resonance(¹H NMR), and electrospray ionization mass spectrometer(ESI-MS) and elemental analysis. The result accords with what we designed theoretically. The novel hyperbranched chromium complex was evaluated as catalyst precursor in the ethylene oligomerization, using methylaluminoxane(MAO) as an activator. At the same time, we investigated the effects of reaction temperature, ethylene pressure, Al/Cr molar ratio, co-catalysts and solvents on the catalytic activity and product selectivity. The oligomerization results show that the activity of the catalyst is 1.32×10⁵ g/(mol(Cr)·h) and the selectivity for C₆ and C₈reaches up to 59.30% at 45 ℃ and 4 MPa, Al/Cr molar ratio of 300 and 7 μmol catalyst loading with MAO as co-catalyst in toluene.

Key words: 1.0 generation hyperbranched macromolecule, hyperbranched bispyridineimine ligand, chromium complex, ethylene oligomerization

WANG Jun,LIU Jinyi,CHEN Liduo,LAN Tianyu,WANG Libo. Synthesis and Ethylene Oligomerization Behavior of Hyperbranched Bispyridineimine Chromium Catalyst[J]. Chinese Journal of Applied Chemistry, 2019, 36(7): 773-781.

References

[1]	Agapie T.Selective Ethylene Oligomerization: Recent Advances in Chromium Catalysis and Mechanistic Investigations[J]. Coord Chem Rev,2011,255(7):861-880.
[2]	McGuinness D S. Olefin Oligomerization via Metallacycles: Dimerization, Trimerization, Tetramerization and Beyond[J]. Chem Rev,2011,111(3):2321-2341.
[3]	Bryliakov K P,Talsi E P.Frontiers of Mechanistic Studies of Coordination Polymerization and Oligomerization of α-Olefins[J]. Coord Chem Rev,2012,256(23):2994-3007.
[4]	Chemical and Engineering News Group. Several Ecolabel Seals for Cleaners and Other Products[J]. Chem Eng News,2013,91(4):10-15.
[5]	CAO Shengxian,CHEN Qian,ZU Chunxing.Linear Alpha Olefin Technology Today and Application Prospects[J]. Sino-Global Energy,2012,17(2):80-85(in Chinese). 曹胜先,陈谦,祖春兴. 线性α-烯烃的技术现状及应用前景[J]. 中外能源,2012,17(2):80-85.
[6]	SONG Xianfeng,BI Siyong,MAO Guoliang,et al. Advance in Catalysts for Trimerization and Tetramerization of Ethylene[J]. Petrochem Technol,2008,37(8):858-861(in Chinese). 宋宪风,毕四勇,毛国梁,等. 乙烯三聚和四聚催化剂的研究进展[J]. 石油化工,2008,37(8):858-861.
[7]	ZHANG Juntao,ZHANG Guoli,LIANG Shengrong,et al. Recent Developments in Heterogeneous Catalyst of Ethylene Oligomerization to α-Oefins[J]. Chem Ind Eng Prog,2008,27(1):157-163(in Chinese). 张君涛,张国利,梁生荣,等. 乙烯齐聚制α-烯烃多相催化剂研究进展[J]. 化工进展,2008,27(1):157-163 .
[8]	Finiels A,Fajula F,Hulea V.Nickel-based Solid Catalysts for Ethylene Oligomerization-A Review[J]. Catal Rev-Sci Eng,2014,4(8):2412-2426.
[9]	Chen L,Hou J,Sun W H.Ethylene Oligomerization by Hydrazone Ni(Ⅱ) Complexes/MAO[J]. Appl Catal A Gen,2003,246(1):11-16.
[10]	Breuil P R,Magna L,Olivier-Bourbigou H.ChemInform Abstract: Role of Homogeneous Catalysis in Oligomerization of Olefins:Focus on Selected Examples Based on Group 4 to Group 10 Transition Metal Complexes[J]. Catal Lett,2015,46(13):173-192.
[11]	Keim W.Oligomerization of Ethylene to α-Olefins:Discovery and Development of the Shell Higher Olefin Process(SHOP)[J]. Angew Chem Int Edit,2013,52(48):12492-12496.
[12]	Boudier A,Breuil P A R,Magna L,et al. Ethylene Oligomerization Using Iron Complexes:Beyond the Discovery of Bis(imino)pyridine Ligands[J]. Chem Commun,2014,50(12):1398-1407.
[13]	Li C Q,Wang F F,Lin Z Y.Novel Nickel Complexes with Hyperbranched Structure:Synthesis, Characterization and Performance in Ethylene Oligomerization[J]. Inorg Chim Acta,2016,453:430-438.
[14]	Boulens P,Lutz M,Jeanneau E,et al. Iminobisphosphines to (Non-)Symmetrical Diphosphinoamine Ligands:Metal-Induced Synthesis of Diphosphorus Nickel Complexes and Application in Ethylene Oligomerisation Reactions[J]. Eur J Inorg Chem,2014,2014(23):3754-3762.
[15]	Kermagoret A,Braunstein P.Mono- and Dinuclear Nickel Complexes with Phosphino-, Phosphinito-, and Phosphonitopyridine Ligands:Synthesis, Structures, and Catalytic Oligomerization of Ethylene[J]. Organometallics,2008,27(1):88-99.
[16]	Boulens P,Pellier E,Jeanneau E.Self-assembled Organometallic Nickel Complexes as Catalysts for Selective Dimerization of Ethylene into 1-Butene[J]. Organometallics,2015,34(7):1139-1142.
[17]	Ainooson M K,Guzei I A,Spencer L C,et al. Pyrazolylimine Iron and Cobalt, and Pyrazolylamine Nickel Complexes:Synthesis and Evaluation of Nickel Complexes as Ethylene Oligomerization Catalysts[J]. Polyhedron,2013,53(4):295-303.
[18]	PEI Haixiang,SHI Pengfei,CHEN Yanhui,et al. Study on the Influence of Cr(Ⅲ) Complex/MAO on Catalytic Oligomerization of Ethylene[J]. Spec Petrochem,2014,31(6):61-66(in Chinese). 裴海香,时鹏飞,陈延辉,等. Cr(Ⅲ)络合物/MAO对催化乙烯齐聚选择性影响的研究[J]. 精细石油化工,2014,31(6):61-66.
[19]	Reagan W K,Freeman J W,Conroy B K.Process for the Preparation of a Catalyst for Olefin Polymerization:EP,EP0608447[P]. 2007.
[20]	Bollmann A,Blann K,Dixon J T,et al. Ethylene Tetramerization:A New Route to Produce 1-Octene in Exceptionally High Selectivities[J]. J Am Chem Soc,2004,126(45):14712-14713.
[21]	Overett M J,Blann K,Bollmann A,et al. Carbon-Bridged Diphosphine Ligands for Chromium-Catalysed Ethylene Tetramerisation and Trimerisation Reactions[J]. J Mol Catal A-Chem,2008,283(1/2):114-119.
[22]	Kim S K,Kim T J,Chung J H,et al. Bimetallic Ethylene Tetramerization Catalysts Derived from Chiral DPPDME Ligands:Syntheses, Structural Characterizations, and Catalytic Performance of [(DPPDME)CrCl3]2(DPPDME=S,S- and R,R-Chiraphos and meso-Achiraphos)[J]. Organometallics,2014,29(22):5805-5811.
[23]	Shaikh Y, Gurnham J, Albahily K,et al. Aminophosphine-Based Chromium Catalysts for Selective Ethylene Tetramerization[J]. Organometallics,2012,31(21):7427-7433.
[24]	Jiang T,Zhang S,Jiang X,et al. The Effect of N-Aryl Bisphosphineamine Ligands on the Selective Ethylene Tetramerization[J]. J Mol Catal A-Chem,2008,279(1):90-93.
[25]	Shaikh Y,Albahily K,Sutcliffe M,et al. A Highly Selective Ethylene Tetramerization Catalyst[J]. Angew Chem Int Ed,2012,124(6):1395-1398.
[26]	Chen Y,Zuo W,Hao P,et al. Chromium(III) Complexes Ligated by 2-(1-Isopropyl-2-benzimidazolyl)-6- (1-(arylimino)ethyl)pyridines:Synthesis, Characterization and Their Ethylene Oligomerization and Polymerization[J]. J Organomet Chem,2008,693(4):750-762.
[27]	Zhang J,Li A,Hor T S A. Ligand Effect on Ethylene Trimerisation with [NNN]-Heteroscorpionate Pyrazolyl Cr(Ⅲ) Catalysts[J]. Dalton Trans,2009,42(42):9327-9333.
[28]	Overett M J,Blann K,Bollmann A,et al. Ethylene Trimerisation and Tetramerisation Catalysts with Polar-substituted Diphosphinoamine Ligands[J]. Chem Commun,2005,2005(5):622.
[29]	Mcguinness D S,Wasserscheid P,Keim W.Novel Cr-PNP Complexes as Catalysts for the Trimerisation of Ethylene[J]. Cheminform,2003,34(23):334-335.
[30]	Killian E,Blann K,Bollmann A.The Use of Bis(diphenylphosphino)amines with N-Aryl Functionalities in Selective Ethylene Tri- and Tetramerisation[J]. J Mol Catal A-Chem,2007,270(1):214-218.
[31]	Albahily K,Fomitcheva V,Gambarotta S,et al. Preparation and Characterization of a Reduced Chromium Complex via Vinyl Oxidative Coupling: Formation of a Self-activating Catalyst for Selective Ethylene Trimerization[J]. J Am Chem Soc,2011,133(16):6380-6387.
[32]	Yang Y,Liu Z,Liu B,et al. Selective Ethylene Tri-/Tetramerization by in Situ-Formed Chromium Catalysts Stabilized by N,P-Based Ancillary Ligand Systems[J]. ACS Catal,2013,3(10):2353-2361.
[33]	Stennett T E,Haddow M F,Wass D F.Avoiding MAO:Alternative Activation Methods in Selective Ethylene Oligomerization[J]. Organometallics,2012,31(19):6960-6965.
[34]	WANG Jun,GAO Rui,YU Yanlong,et al. Synthesis and Catalytic Performance of Novel Dendritic PNP Chromium Catalysts[J]. Chem J Chinese Univ,2017,38(7): 1257-1263(in chinese). 王俊,高瑞,于彦龙,等. 新型树枝状PNP铬催化剂的合成及催化性能[J]. 高等学校化学学报,2017,38(7):1257-1263.
[35]	Wang J,Li C Q,Zhang S Y,et al. Synthesis and Characterization of Lower Generation Broom Molecules[J]. Chinese Chem Lett,2008,19(1):43-46.
[36]	WANG Qiuan,FAN Huafang,LIAO Tougen. Technical Handbook of Organic Chemistry Laboratory[M]. Beijing:Chemical Industry Press,2012:201-221(in Chinese). 王秋安,范华芳,廖头根. 有机化学实验室技术手册[M]. 北京:化学工业出版社,2012:201-221.
[37]	NING Yongcheng. Structural Identification and Organic Spectroscopy of Organic Compounds[M]. Beijing:Science Press,2014(in chinese). 宁永成. 有机化合物结构鉴定与有机波谱学[M]. 北京:科学出版社,2014.
[38]	ZHANG Danfeng,SUN Yue,DENG Xiaojuan,et al. Synthesis and Catalytic Ethylene Polymerization of Di(β-Hydroxyimine) Titanium Dichloride Complex[J]. Chem J Chinese Univ,2012,33(9):2121-2128(in Chinese). 张丹枫,孙悦,邓筱娟,等. 二(β-羟亚胺)二氯化钛配合物的合成及催化乙烯聚合[J]. 高等学校化学学报,2012,33(9):2121-2128.
[39]	SHI Weiguang,FU Zijian,WANG Sihan,et al. Synthesis of Hyperbranched Salicylaldimine Nickel Catalyst and Its Catalytic Performance for Ethylene Oligomerization with Isopropylamine as a Nuclear[J]. Chem Ind Eng Prog,2017,36(5):1727-1733(in Chinese). 施伟光,符子剑,王斯晗,等. 异丙胺为核合成超支化水杨醛亚胺镍系催化剂及其催化乙烯齐聚性能[J]. 化工进展,2017,36(5):1727-1733.
[40]	Pokutsa A P,Sheparovich R B,Zaborovskii A B.Mild Oxidation of Cyclohexane Catalyzed by Cobalt(Ⅱ) Acetate and Initiated by H2O2 in the Acetic Acid Medium[J]. Kinet Catal,2002,43(5):691-697.
[41]	Malgas-enus R. The Preparation and Characterization of Multinuclear Catalysts Based on Novel Dendrimers:Application in the Oligomerization and Polymerization of Unsaturated Hydrocarbons[D]. Stellenbosch: University of Stellenbosch,2011:163.

Synthesis and Ethylene Oligomerization Behavior of Hyperbranched Bispyridineimine Chromium Catalyst

RichHTML

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 3

Recommended Articles

Metrics

Comments

[1]	Feng LI, Shi-Yu LU, Yu ZHANG, Li-Jun GUO, Xue ZHAI, Cui-Qin LI. Catalytic Properties of Silylated⁃Salicylaldimine Transition Metal Complexes Functionalized Nano⁃silica Catalysts in Ethylene Oligomerization [J]. Chinese Journal of Applied Chemistry, 2022, 39(6): 949-959.
[2]	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.
[3]	Song Baolin, Sun Baiwang, Niu Dezhong, Lu Zaisheng, Lu Xiangsheng. SYNTHESIS AND PROPERTIES OF THE COORDINATION COMPOUNDS OF Cr(Ⅲ)WITH 1-HYDROXY-2(1H)-PYRIDINETHIONE AND ITS METHYL DERIVATIVES [J]. Chinese Journal of Applied Chemistry, 1993, 0(5): 78-80.