Progress of Friedel-Crafts alkylation reaction in catalyst system of ethylene oligomerization

doi:10.11949/j.issn.0438-1157.20160644

Abstract

Abstract:

Using transition metal complexes to catalyse ethylene oligomerization is an important route for preparing α-olefins. The partially catalytic systems have entered the stage of pilot and industrial production. However, the recent researches have suggested that the oligomerization products of some transition metal catalysts in toluene solvent may react with toluene directly as Friedel-Crafts alkylation reaction, which could open a new way for the production of alkylbenzene. This paper reviews the progress of Friedel-Crafts alkylation reaction in ethylene oligomerization in recent years. The influence of the structure of catalysts, catalytic system and process conditions on the alkylation reaction is described in detail. Meanwhile, it gives the Friedel-Crafts alkylation reaction process in ethylene oligomerization, which would be of great significance to design the catalysts that could catalyse ethylene oligomerization to make mixed alkylbenzenes.

Key words: catalysis, ethylene oligomerization, catalyst, Friedel-Crafts alkylation, alkylbenzene, reaction

摘要：

采用过渡金属配合物催化乙烯齐聚是制备α-烯烃的一条重要工艺路线，部分催化体系已进入了中试和工业化生产阶段，但近年来的研究工作表明，一些过渡金属催化剂在甲苯溶剂中的齐聚产物可直接与甲苯发生Friedel-Crafts烷基化反应，这将为烷基苯的生产开辟一条新的途径。综述了近年来乙烯齐聚过程中发生Friedel-Crafts烷基化反应的研究进展，详细阐述了催化剂的结构、催化体系、工艺条件等对烷基化反应及烷基化产物分布的影响。同时，给出了乙烯齐聚中Friedel-Crafts烷基化反应的反应过程，对设计可催化乙烯齐聚制备混合烷基苯的催化剂具有重要的意义。

关键词: 催化, 乙烯齐聚, 催化剂, Friedel-Crafts烷基化, 烷基苯, 反应

CLC Number:

O643.32

WANG Jun, HOU Shuang, SONG Lei, WANG Sihan, LI Cuiqin. Progress of Friedel-Crafts alkylation reaction in catalyst system of ethylene oligomerization[J]. CIESC Journal, 2016, 67(11): 4541-4551.

王俊, 侯爽, 宋磊, 王斯晗, 李翠勤. 乙烯齐聚催化体系中的Friedel-Crafts烷基化反应研究进展[J]. 化工学报, 2016, 67(11): 4541-4551.

References 45

[1]	OLECHOWSKI J. Alkylation process:US 3720725[P]. 1973-3-13.
[2]	OJWACH S O, GUZEI I A, BENADE L L, et al. (Pyrazol-1-ylmethyl)pyridine nickel complexes:ethylene oligomerization and unusual Friedel-Crafts alkylation catalysts[J]. Organometallics, 2009, 28(7):2127-2133.
[3]	ZHANG Y, CAO Y, LENG X, et al. Cationic palladium (Ⅱ) complexes of phosphine-sulfonamide ligands:synthesis, characterization, and catalytic ethylene oligomerization[J]. Organometallics, 2014, 33(14):3738-3745.
[4]	DOHERTY M D, TRUDEAU S, WHITE P S, et al. Ethylene oligomerization catalyzed by a unique phosphine-oxazoline palladium (Ⅱ) complex. Propagation and chain transfer mechanisms[J]. Organometallics, 2007, 26(5):1261-1269.
[5]	SMALL B L, RIOS R, FERNANDEZ E R, et al. Oligomerization of ethylene using new iron catalysts bearing pendant donor modified α-diimine ligands[J]. Organometallics, 2007, 26(7):1744-1749.
[6]	ITTEL S D, JOHNSON L K, BROOKHART M. Late-metal catalysts for ethylene homo-and copolymerization[J]. Chemical Reviews, 2000, 100(4):1169-1204.
[7]	AINOOSON M K, OJWACH S O, GUZEI I A, et al. Pyrazolyl iron, cobalt, nickel, and palladium complexes:synthesis, molecular structures, and evaluation as ethylene oligomerization catalysts[J]. Journal of Organometallic Chemistry, 2011, 696(8):1528-1535.
[8]	KEIM W, HOFFMANN B, LODEWICK R, et al. Linear oligomerization of olefins via nickel chelate complexes and mechanistic considerations based on semi-empirical calculations[J]. Journal of Molecular Catalysis, 1979, 6(2):79-97.
[9]	BUDHAI A, OMONDI B, OJWACH S O, et al. Tandem ethylene oligomerisation and Friedel-Crafts alkylation of toluene catalysed by bis-(3,5-dimethylpyrazol-1-ylmethyl) benzene nickel(Ⅱ) complexes and ethylaluminium dichloride[J]. Catalysis Science &Technology, 2013, 3(12):3130-3135.
[10]	KERMAGORET A, BRAUNSTEIN P. Mono-and dinuclear nickel complexes with phosphino-, phosphinito-, and phosphonitopyridine ligands:synthesis, structures, and catalytic oligomerization of ethylene[J]. Organometallics, 2007, 27(1):88-99.
[11]	KERMAGORET A, TOMICKI F, BRAUNSTEIN P. Nickel and iron complexes with N, P, N-type ligands:synthesis, structure and catalytic oligomerization of ethylene[J]. Dalton Transactions, 2008, 252(22):2945-2955.
[12]	SPEISER F, BRAUNSTEIN P, SAUSSINE L. Nickel and iron complexes with oxazoline-or pyridine-phosphonite ligands; synthesis, structure and application for the catalytic oligomerisation of ethylene[J]. Dalton Transactions, 2004, 10(10):1539-1545.
[13]	KERMAGORET A, BRAUNSTEIN P. Contrasting bonding modes of a tridentate bis(oxazoline)phosphine ligand in cobalt and iron vs palladium complexes:unprecedented N, N-coordination for a N, P, N ligand[J]. Dalton Transactions, 2008, 2008(5):585-587.
[14]	SPEISER F, BRAUNSTEIN P, SAUSSINE L. New nickel ethylene oligomerization catalysts bearing bidentate P, N-phosphinopyridine ligands with different substituents α to phosphorus[J]. Organometallics, 2004, 23(11):2625-2632.
[15]	SPEISER F, BRAUNSTEIN P, SAUSSINE L. Nickel complexes bearing new P, N-phosphinopyridine ligands for the catalytic oligomerization of ethylene[J]. Organometallics, 2004, 23(11):2633-2640.
[16]	SPEISER F, BRAUNSTEIN P, SAUSSINE L. Nickel complexes bearing new P, N-phosphinopyridine ligands for the catalytic oligomerization of ethylene[J]. Accounts of Chemical Research, 2005, 38(10):784-793.
[17]	SPEISER F, BRAUNSTEIN P, SAUSSINE L, et al. Nickel complexes with oxazoline-based P, N-chelate ligands:synthesis, structures, and catalytic ethylene oligomerization behavior[J]. Organometallics, 2004, 23(11):2613-2624.
[18]	OBUAH C, OMONDI B, NOZAKI K, et al. Solvent and co-catalyst dependent pyrazolylpyridinamine and pyrazolylpyrroleamine nickel(Ⅱ) catalyzed oligomerization and polymerization of ethylene[J]. Journal of Molecular Catalysis A Chemical, 2014, 382(382):31-40.
[19]	NYAMATO G S, OJWACH S O, AKERMAN M P, et al. Unsymmetrical (pyrazolylmethyl)pyridine metal complexes as catalysts for ethylene oligomerization reactions:role of solvent and co-catalyst in product distribution[J]. Journal of Molecular Catalysis A Chemical, 2014, 394(10):274-282.
[20]	RUEPING M, NACHTSHEIM B J. A review of new developments in the Friedel-Crafts alkylation-from green chemistry to asymmetric catalysis[J]. Beilstein Journal of Organic Chemistry, 2010, 6(4):1007-1013.
[21]	NYAMATO G S, ALAM M, OJWACH S O, et al. Nickel (Ⅱ) complexes bearing pyrazolylpyridines:synthesis, structures and ethylene oligomerization reactions[J]. Applied Organometallic Chemistry, 2016, 30(2):89-94.
[22]	SCHWEINFURTH D, SU C Y, WEI S C, et al. Nickel complexes with "click"-derived pyridyl-triazole ligands:weak intermolecular interactions and catalytic ethylene oligomerisation[J]. Dalton Transactions, 2012, 41(41):12984-12990.
[23]	BOUDIER A, BREUIL P A R, MAGNA L, et al. Ethylene oligomerization using iron complexes:beyond the discovery of bis(imino) pyridine ligands[J]. Chemical Communications, 2014, 50(12):1398-1407.
[24]	HE F, HAO X, CAO X, et al. Nickel halide complexes bearing 2-benzimidazolyl-N-arylquinoline-8-carboxamide derived ligands:synthesis, characterization and catalytic behavior towards ethylene oligomerization and the vinyl polymerization of norbornene[J]. Journal of Organometallic Chemistry, 2012, 712(5):46-51.
[25]	BOUDIER A, BREUIL P A R, MAGNA L, et al. Nickel(Ⅱ) complexes with imino-imidazole chelating ligands bearing pendant donor groups (SR, OR, NR2, PR2) as precatalysts in ethylene oligomerization[J]. Journal of Organometallic Chemistry, 2012, 718:31-37.
[26]	CHANDRAN D, LEE K M, CHANG H C, et al. Ni(Ⅱ) complexes with ligands derived from phenylpyridine, active for selective dimerization and trimerization of ethylene[J]. Journal of Organometallic Chemistry, 2012, 718(718):8-13.
[27]	MA J, FENG C, WANG S, et al. Bi-and tri-dentate imino-based iron and cobalt pre-catalysts for ethylene oligo-/polymerization[J]. Inorganic Chemistry Frontiers, 2014, 1(1):14-34.
[28]	ASTRUC D, CHARDAC F. Dendritic catalysts and dendrimers in catalysis.[J]. Chemical Reviews, 2001, 101(9):2991-3024.
[29]	ANDRES R, JESUS E D, FLORES J C. Catalysts based on palladium dendrimers[J]. New Journal of Chemistry, 2007, 31(7):1161-1191.
[30]	MALGAS-ENUS R, MAPOLIE S F, SMITH G S. Norbornene polymerization using multinuclear nickel catalysts based on a polypropyleneimine dendrimer scaffold[J]. Journal of Organometallic Chemistry, 2008, 693(13):2279-2286.
[31]	MALGAS-ENUS R, MAPOLIE S F. A novel nickel (Ⅱ) complex based on a cyclam-cored generation-one dendrimeric salicylaldimine ligand and its application as a catalyst precursor in norbornene polymerization:comparative study with some other first generation DAB-polypropyleneimine metallodendrimers[J]. Polyhedron, 2012, 47(1):87-93.
[32]	MALGAS-ENUS R, MAPOLIE S F. Nickel metallodendrimers as catalyst precursors in the tandem oligomerization of ethylene and Friedel-Crafts alkylation of its olefinic products[J]. Inorganica Chimica Acta, 2014, 409(1):96-105.
[33]	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.
[34]	王海琛. 树枝状亚胺水杨醛镍配合物的合成及催化性能研究[D]. 大庆:东北石油大学, 2013. WANG H C. Study on the synthesis and catalysis of dendritic imine salicylad nickel complexes[D].Daqing:Northeast Petroleum University, 2013.
[35]	DYER P W, FAWCETT J, HANTON M J. et al. Rigid N-phosphino guanidine P, N ligands and their use in nickel-catalyzed ethylene oligomerization[J]. Organometallics, 2008, 27(19):5082-5087.
[36]	秦一超, 叶健, 蒋斌波, 等. 芳氧基锆系催化剂催化乙烯齐聚与Friedel-Crafts烷基化的串联反应[J]. 高等学校化学学报, 2015, 36(9):1825-1831. QIN Y C, YE J, JIANG B B, et al. Ethylene oligomerization and Friedel-Crafts alkylation tandem action catalyzed by aryloxy zirconium catalyst[J]. Chemical Journal of Chinese Universities, 2015, 36(9):1825-1831.
[37]	ZAIDMAN A V, KAYUMOV R R, BELOV G P, et al. Ethylene oligomerization in the presence of catalytic systems based on nickel(Ⅱ) formazanates[J]. Petroleum Chemistry, 2010, 50(6):450-454.
[38]	ZAIDMAN A V, PERVOVA I G, VILMS A I, et al. Synthesis, characterization and ethylene oligomerization studies of nickel (Ⅱ) based new formazane derivatives[J]. Inorganica Chimica Acta, 2011, 367(1):29-34.
[39]	PAVLOVA I S, PERVOVA I G, BELOV G P, et al. Ethylene oligomerization mediated by iron formazanates and organoaluminum compounds[J]. Petroleum Chemistry, 2013, 53(2):127-133.
[40]	SONG K, GAO H, LIU F, et al. Syntheses, structures, and catalytic ethylene oligomerization behaviors of bis (phosphanyl) aminenickel (Ⅱ) complexes containing N-functionalized pendant groups[J]. European Journal of Inorganic Chemistry, 2009, 2009(20):3016-3024.
[41]	PEREGO C, INGALLINA P. Recent advances in the industrial alkylation of aromatics:new catalysts and new processes[J]. Catalysis Today, 2002, 73(1):3-22.
[42]	XIAO L, JOHNSON K E, TREBLE R G. Alkane cracking, alkene polymerization, and Friedel-Crafts alkylation in liquids containing the acidic anions HX2-, XH (AlX4)-, XH (Al2 X7)-, and Al2 X7-(X=chlorine, bromine)[J]. Journal of Molecular Catalysis A:Chemical, 2004, 214(1):121-127.
[43]	ORMA A, GARCIA H. Lewis acids:from conventional homogeneous to green homogeneous and heterogeneous catalysis[J]. Chemical Reviews, 2003, 103(11):4307-4366.
[44]	BUSCA G. Acid catalysts in industrial hydrocarbon chemistry[J]. Chemical Reviews, 2007, 107(11):5366-5410.
[45]	DAVIS R J. New perspectives on basic zeolites as catalysts and catalyst supports[J]. Journal of Catalysis, 2003, 216(1):396-405.