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Preparation method of benzoyl-substituted 1,10-phenanthroline complex and catalytic application in ethylene oligomerization
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A kind of technology of benzoyl group and phenanthroline is applied in the field of preparation of olefin oligomerization catalyst, and can solve the problems of many synthesis steps and the like
Active Publication Date: 2013-03-13
CHINA PETROLEUM & CHEM CORP +1
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However, this catalyst preparation method has the following disadvantages: too many steps for ligand synthesis, and highly toxic potassiumcyanide and expensive and highly toxic selenium dioxide are required to participate in the reaction
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Embodiment 1
[0033] 1. Catalyst chlorination of 2-benzoyl-1,10-phenanthroline 2,6-diethylanilinate iron (II) complex synthesis:
[0034] Step A, the synthesis of 2-benzoyl-1,10-phenanthroline;
[0035]
[0036] Put 5.1 g (0.03 mol) of 1,10-phenanthroline into a 250 ml three-necked flask, and dissolve it with 100 ml of toluene under nitrogen protection and magnetic stirring. Slowly add 60ml of benzyllithium 1.2M n-hexane solution (0.07mol) dropwise to the three-necked flask under stirring at -60°C, and the dropwise addition is completed in about 15 minutes. Continue stirring at this temperature for 18 hours, and then heat up to At about 30°C, continue to stir for 10 hours. Then the temperature of the reaction mixture was lowered to about -10°C, 50ml of distilled water was slowly added thereto, and then the temperature was raised to 30°C and stirred for 10 hours. Separate the liquids, take out the organic phase, extract the inorganic phase three times with dichloromethane (50 ml each ti...
Embodiment 2-47
[0054] Repeat the three steps of A, B and C in Example 1 to prepare the catalyst, except that the 2,6-diethylaniline in the step B of Example 1 is replaced by the following substituted anilines: 2-methylaniline , 3-methylaniline, 4-methylaniline, 2,3-dimethylaniline, 2,4-dimethylaniline, 2,5-dimethylaniline, 2,6-dimethylaniline, 3 , 4-dimethylaniline, 3,5-dimethylaniline, 2,4,6-trimethylaniline, 4-bromo-2,6-dimethylaniline, 2-ethylaniline, 2-ethyl Base-6-methylaniline, 2-isopropylaniline, 2,6-diisopropylaniline, 2-fluoroaniline, 2-fluoro-4-methylaniline, 2-fluoro-5-methylaniline, 2,4-difluoroaniline, 2,5-difluoroaniline, 2,6-difluoroaniline, 3,4-difluoroaniline, 2,3,4-trifluoroaniline, 2,4,5-trifluoroaniline Aniline, 2,4,6-trifluoroaniline, 2,3,4,5,6-pentafluoroaniline, 3-chloroaniline, 2,6-dichloroaniline, 2,3,4-trichloroaniline, 2 , 4,5-trichloroaniline, 2,4,6-trichloroaniline, 2-bromoaniline, 2-bromo-4-methylaniline, 2-bromo-4-fluoroaniline, 4-bromo-2-fluoro Aniline, 2,6...
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Abstract
The invention provides a method for preparing a chlorinated 2-benzoyl-1,10-phenanthroline condensed amine iron (II) complex shown in formula I, and its catalytic application in ethylene oligomerization. The preparation method comprises the following steps: orderly performing hydrolysis and an oxidation reaction with nitrobenzene of initial reaction raw materials of 1,10-phenanthroline and benzyl lithium to obtain 2-benzoyl-1,10-phenanthroline, then performing condensation of 2-benzoyl-1,10-phenanthroline with substituted aniline to obtain 2-benzoyl-1,10-phenanthroline condensed amine ligand, and reacting the ligand with ferrouschloride to obtain a target product I. The synthetic method provided by the invention is few in steps, and simple in process, substitutes nitrobenzene for selenium dioxide in the prior art for the oxidation reaction, substitutes nontoxic benzyl lithium for hypertoxic potassiumcyanide in the prior art, reduces the preparation cost of the catalyst, and has wide industrialization prospects.
Description
technical field [0001] The present invention relates to the preparation method of olefin oligomerization catalyst, more specifically relate to the preparation method of benzoyl-substituted 1,10-phenanthroline amido iron (II) complex, and the complex prepared thereby is used as ethylene Application of oligomerization catalysts. Background technique [0002] Ethylene oligomerization is one of the most important reactions in the olefin polymerization industry. Through oligomerization, cheap small molecule olefins can be transformed into products with high added value. Ethylene oligomerization product-linear α-olefin (LAO) is an important organic chemical raw material. e.g. C 4 -C 30 LAO can be used to prepare daily cleaning agents, flotation agents, emulsifiers, lubricating components of refrigerators and drilling fluids, plasticizers, various additives, low-viscosity synthetic oils, polymers and copolymers , Petroleum and petroleum product additives, higher alkylamines, h...
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