Preparation Method and Use Of Ethylene Oligomerization Catalyst

Fe ^{2 + , Co 2 + and Ni 2 + < ethylene, 2-imino-1,10-phenanthroline ligand polymerization and low Polymerization catalyst / chloride. The invention also discloses methods of making and using the catalyst. Under the action of methylaluminoxane cocatalyst, the catalyst has good ethylene oligomerization and polymerization performance, and the ethylene oligomeric iron (II) complex exhibits high polymerization activity, reaching 10 7 gmolFe -1 ħ -1 . The oligomerization product includes C _{4 , C 6 , C 8 , C 10 , C 12 < / / sub>, C 14 , C 16 , C 18 , C 20 and C 22 The selectivity of the α-olefin is as high as 99.5%; the polymer is a low molecular weight polyolefin and a polyolefin wax. The alkyl aluminum chloride includes trimethyl aluminum, triethyl aluminum, triisobutyl aluminum, tri-n-hexyl aluminum, tri-n-octyl aluminum, diethyl aluminum chloride, ethyl aluminum dichloride cocatalyst, when The catalytic system can also be subjected to catalytic oligomerization and polymerization of ethylene. The dependence of the present invention on the oligomerization of ethylene and the polymerization activity of the catalyst and the changing conditions were measured.}}

 

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a late transition metal complex of a class of ethylene oligomerization and polymerization catalysts, i.e., containing tridentate N, AN iron ligand (II), cobalt (II) And a catalyst for the complex of nickel (II), which is prepared and used for the purpose of catalytic oligomerization polymerization of ethylene. BACKGROUND OF THE INVENTION Ethylene oligomerization of linear olefins may be a large-scale production, the products of which are important organic chemical intermediates having many different properties and uses, for example as detergents, plasticizers, synthetic lubricants and preparation straight Chain low density polyethylene (LLDPE) comonomers, and the like. Since the 1970s, homogeneous transition metal complexes have attracted attention for ethylene oligomerization. The earliest Shell (Shdl) discovered a method for preparing shell higher olefins, namely SHOP (shell higher olefin process) method, related patents. U.S. Patent 3,686,351,197,712,011 and US Pantent 3676523,19720822, which are OP bridged ligand type nickel catalysts, the catalytic activity of ethylene oligomerization is about 105 g mol·((Ni)h'1, 99% of the products in the process are Linear olefins, in which α-olefins are suitable for 98X, and have been widely used in industrial production and .Ph PhA / Ni \ Ph ^ O PPh3 However, while efforts are being made to improve existing catalysts, efforts have been made to study novel catalysts and to simplify synthesis of catalysts. And preparation processes, increased catalytic activity. Product selectivity and catalytic activity of active catalysts In recent years, various late transition metal catalyst systems O, N, P, etc. have been developed as heteroatom ligands, wherein the ligand is nitrogen of the teeth. The procatalyst has attracted a lot of attention in recent patents, for example: Jpn Kokai Tokkyo Koho JP 11060627, A2 March 2, 1999. PCT Int Appl WO 9923096 Al 14Mayl999; PCT In.t. Application WO 9951550 Al 140ctl999. The oligomerization and polymerization of ethylene follow the same reaction mechanism, therefore, the oligomerization and polymerization of ethylene are the catalytic properties of two different ethylene reaction products. Polyolefin resin 5, Compared with other resin materials, olefin resin has excellent environmental compatibility and is used in materials developed by the developed countries in the automotive industry. In 2003, the world's output reached 83.3 million tons; among them, polyethylene is the fastest growing, output. The highest and most versatile synthetic resin, with an annual output of 51.1 million tons. Commercially available catalysts for polyethylene are Ziegler-Natta type catalysts (DE Pat 889229 (1953); IT Pat 545332 (195'6) Wo B IT Pat 536899 (1955); Chem Rev" 2000, 100, 1169 and special Literature), Phillips type catalyst (Belg Pat 530617 (1955 ..); Chem Rev. 1996, 96, 3327) and homogeneous metallocene catalyst 20 (W. Kaminsky, Synthetic and Polymerized Metal Organic Catalyst, Berlin: Springer) , 1999). In recent years, the development of high-efficiency oligomeric transition metal-type metal complexes, the development of oligomerization and polymerization catalysts. In 1995, Brookhart et al. reported a class of a-diimine Ni which can be polymerized with highly reactive ethylene. (II) Complex. The following formula (..J. ​​Am Chem Soc, 1995, 117, 6414-6415.):

 

In 1998, Brookhart and Gibson et al. reported that Fe(II) and Co(II) complexes of pyridine diimine can be oligomerized or polymerized into ethylene by adjusting the substituents on the benzene ring. The structure is as shown below. (.J. Am Chem, Soc, 1998, 120, 4049-4050; Chem Commun 1998, 849-850 ...): In the past few years, applicants have been working on ethylene oligomerization and polymerization catalysts and methods.

 

Research and development of various types of nickel complexes low polyethylene catalysts TYPE: Chinese patent ZL00 121033.5, application date, 2000 July 17, 2003 authorization notice 8; China patent application submitted in May 2001 01118455.8; May 31st; Chinese patent ZL01 1 20214.9, application date: July 6, 2001, authorization notice 2004.7.7; Chinese patent application number 01120554.7 submitted on July 20, 2001; Chinese patent ZL 02 1 18523.9, applied for Japan 2002 April 26, Authorization Announcement 2004.12.22; Chinese Patent ZL02 1 23213.X, Application Date June 12, 2002, Authorization Announcement 2003.11.19; China Patent Application No. 01317727.0 submitted in June 2003 (May 23) Chinese Patent Application No. 03148378.X, Application Date July 2, 2003; Chinese Patent Application No. 03154463.0 filed on Oct. 8, 2003; Chinese Patent Application No. 200410086284.7 filed on Oct. 29, 2004. China please review the patent number 200410081711.2 submitted on December 30, 2004. At the same time, research and invention on oligomerization and ethylene polymerization of iron complexes.

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CAS No. 100914-80-5 [1,1'-Biphenyl]-2-carboxaldehyde, 2'-acetyl- Catalog No.:AG00036O MDL No.: MF:C15H12O2 MW:224.2546	CAS No. 100915-02-4 Benzoic acid, 4-(4-formylphenoxy)-, methyl ester Catalog No.:AG00036N MDL No.: MF:C15H12O4 MW:256.2534	CAS No. 100915-48-8 Pentanedioic acid, 2,4-diacetyl-3-formyl-, 1,5-diethyl ester Catalog No.:AG00036M MDL No.: MF:C14H20O7 MW:300.3044
CAS No. 100915-63-7 Butanamide, N-(4-chlorophenyl)-3-(diethylamino)- Catalog No.:AG00037O MDL No.: MF:C14H21ClN2O MW:268.7823	CAS No. 10092-04-3 Azuleno[6,5-b]furan-2,5-dione, 4-(acetyloxy)-3,3a,4,4a,7a,8,9,9a-octahydro-3,4a,8-trimethyl-, (3R,3aR,4R,4aR,7aR,8R,9aS)- Catalog No.:AG00037R MDL No.: MF:C17H22O5 MW:306.3536	CAS No. 10092-63-4 8-Quinolinesulfonic acid, 5-fluoro- Catalog No.:AG00037Q MDL No.: MF:C9H6FNO3S MW:227.2122
CAS No. 10092-77-0 Phosphonic acid, P-butyl-, bis(2-methylpropyl) ester Catalog No.:AG00037P MDL No.: MF:C12H27O3P MW:250.3147	CAS No. 100920-71-6 Benzenesulfonamide, 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]-, mixt. with N'-(3,4-dichlorophenyl)-N-methoxy-N-methylurea Catalog No.:AG00037N MDL No.: MF:C21H22Cl3N7O6S MW:606.8667	CAS No. 100922-16-5 2-Butenedioic acid (2E)-, 1-(1,1-dimethylethyl) 4-ethyl ester Catalog No.:AG00037M MDL No.: MF:C10H14O4-- MW:198.2158
CAS No. 100922-54-1 L-Lysine, N2-(N-L-γ-glutamyl-L-γ-glutamyl)- (9CI) Catalog No.:AG00037L MDL No.: MF:C16H28N4O8 MW:404.4155	CAS No. 100922-79-0 Pyridinium, 1-(4-cyanophenyl)-, chloride (1:1) Catalog No.:AG00037K MDL No.: MF:C12H9ClN2 MW:216.6663	CAS No. 100922-96-1 1H-Indazol-3-ol Catalog No.:AG00037J MDL No.:MFCD00044658 MF:C7H6N2O MW:134.1353
CAS No. 100922-97-2 1H-Indazol-3-ol, 1-methyl- Catalog No.:AG00037I MDL No.: MF:C8H8N2O MW:148.1619	CAS No. 100923-72-6 Methanone, (4-amino-2,6-dimethylphenyl)phenyl- Catalog No.:AG00037H MDL No.: MF:C15H15NO MW:225.2857	CAS No. 100923-74-8 Methanone, (2-hydroxy-4,6-dimethylphenyl)(2,4,6-trimethylphenyl)- Catalog No.:AG00037G MDL No.: MF:C18H20O2 MW:268.3502
CAS No. 100923-75-9 Methanone, (4-hydroxy-2,6-dimethyl-3-nitrophenyl)phenyl- Catalog No.:AG00037F MDL No.: MF:C15H13NO4 MW:271.2680	CAS No. 1009237-29-9 2-Pyrrolidinecarboxamide, N-(1,3-benzodioxol-5-ylmethyl)-5-oxo- Catalog No.:AG000373 MDL No.: MF:C13H14N2O4 MW:262.2613	CAS No. 100924-63-8 Butanenitrile, 4,4-dimethoxy-2-methyl- Catalog No.:AG00037E MDL No.: MF:C7H13NO2 MW:143.1836
CAS No. 100924-68-3 Benzenamine, 2-[(1H-benzimidazol-2-ylsulfinyl)methyl]-N,N-dimethyl- Catalog No.:AG00037D MDL No.: MF:C16H17N3OS MW:299.3907	CAS No. 100924-69-4 Adenosine, 5'-S-[3-amino-3-(hydroxyphosphinyl)propyl]-5'-thio- (9CI) Catalog No.:AG00037C MDL No.: MF:C13H21N6O5PS MW:404.3818	CAS No. 100925-29-9 Benzenamine, 4-methoxy-2-methyl-N-(2-methylphenyl)- Catalog No.:AG00037B MDL No.: MF:C15H17NO MW:227.3016
CAS No. 100925-76-6 4H-Cyclopenta[b]thiophene-4,6(5H)-dione Catalog No.:AG00037A MDL No.:MFCD18451561 MF:C7H4O2S MW:152.1705	CAS No. 100926-71-4 Carbamic acid, (4-methoxyphenyl)-, 7-quinolinyl ester (9CI) Catalog No.:AG000379 MDL No.: MF:C17H14N2O3 MW:294.3047	CAS No. 100926-72-5 Carbamic acid, (4-methoxyphenyl)-, 6-quinolinyl ester (9CI) Catalog No.:AG000378 MDL No.: MF:C17H14N2O3 MW:294.3047
CAS No. 100926-75-8 Carbamic acid, (2-methoxyphenyl)-, 6-quinolinyl ester (9CI) Catalog No.:AG000377 MDL No.: MF:C17H14N2O3 MW:294.3047	CAS No. 100927-10-4 Carbamic acid, N-[(1R)-2-amino-1-methylethyl]-, 1,1-dimethylethyl ester Catalog No.:AG000376 MDL No.:MFCD11112229 MF:C8H18N2O2 MW:174.2407	CAS No. 100928-14-1 2-Pyridinecarboxylic acid, 6-[[(acetyloxy)imino]methyl]- Catalog No.:AG000375 MDL No.: MF:C9H8N2O4 MW:208.1708
CAS No. 100929-39-3 Cyclodecatrienetetraylium (9CI) Catalog No.:AG000374 MDL No.: MF:C10H10++++ MW:130.1864	CAS No. 1009298-59-2 Benzamide, 3-[2,4-bis[(3S)-3-methyl-4-morpholinyl]pyrido[2,3-d]pyrimidin-7-yl]-N-methyl- Catalog No.:AG000382 MDL No.:MFCD22628784 MF:C25H30N6O3 MW:462.5441	CAS No. 1009299-03-9 1H-Inden-1-one, 4-(1,1-dimethylethyl)-2,3-dihydro- Catalog No.:AG000381 MDL No.: MF:C13H16O MW:188.2655
CAS No. 1009303-44-9 Pyrido[2,3-d]pyrimidine, 7-chloro-2,4-bis[(3S)-3-methyl-4-morpholinyl]- Catalog No.:AG000380 MDL No.:MFCD18782759 MF:C17H22ClN5O2 MW:363.8419	CAS No. 1009303-56-3 Boronic acid, B-[4-fluoro-3-(2H-tetrazol-5-yl)phenyl]- Catalog No.:AG00037Z MDL No.:MFCD13176533 MF:C7H6BFN4O2 MW:207.9575	CAS No. 1009303-59-6 Boronic acid, B-[3-cyano-4-(1-methylethoxy)phenyl]- Catalog No.:AG00037Y MDL No.:MFCD17011847 MF:C10H12BNO3 MW:205.0182
CAS No. 1009303-77-8 Benzenemethanol, 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Catalog No.:AG00037X MDL No.:MFCD13184694 MF:C14H21BO4 MW:264.1251	CAS No. 1009303-78-9 Benzoic acid, 2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Catalog No.:AG00037W MDL No.: MF:C13H17BO5 MW:264.0821	CAS No. 1009306-52-8 3-Quinolinecarboxylic acid, 2-(chloromethyl)-4-methyl-, ethyl ester, hydrochloride (1:1) Catalog No.:AG00037V MDL No.:MFCD07308466 MF:C14H15Cl2NO2 MW:300.1804
CAS No. 1009307-13-4 2-Propenoic acid, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester, (2E)- Catalog No.:AG00037U MDL No.:MFCD09027313 MF:C11H19BO4 MW:226.0772	CAS No. 1009309-65-2 Ethanamine, N-[(4-bromophenyl)methylene]-2,2-dimethoxy- Catalog No.:AG00037T MDL No.: MF:C11H14BrNO2 MW:272.1384	CAS No. 1009318-82-4 1H-Pyrazole-4-carboxylic acid, 3-(difluoromethyl)-1-methyl-, methyl ester Catalog No.:AG00037S MDL No.: MF:C7H8F2N2O2 MW:190.1474