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P-phenyl substituted alpha-diimine palladium catalyst and preparation method thereof

A phenyl-substituted, diimide palladium technology, applied in the field of lubricating oil, can solve the problems of harsh oligomerization reaction conditions and difficult process, and achieve the effects of high viscosity, improved catalytic activity and high viscosity index

Inactive Publication Date: 2019-10-18
JIANGSU ZHONGSHENG GAOKE ENVIRONMENTAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The lubricating oil obtained by using MAO catalyst has excellent comprehensive properties, but MAO easily reacts with water in the air, so the oligomerization reaction conditions are extremely harsh and the process is very difficult

Method used

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  • P-phenyl substituted alpha-diimine palladium catalyst and preparation method thereof
  • P-phenyl substituted alpha-diimine palladium catalyst and preparation method thereof
  • P-phenyl substituted alpha-diimine palladium catalyst and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] This embodiment is to prepare the α-diimine palladium catalyst substituted by p-phenyl, which is denoted as catalyst C1 here, and its specific preparation process is as follows:

[0033] S1: Synthesis of Ligand L1:

[0034] 4-Phenyl-2,6-diisopropylaniline (5.07 g, 20 mmol) and 2,3-butanedione (0.85 g, 10 mmol) were dissolved in 30 mL of anhydrous methanol, and 0.25 g of formic acid was added under stirring , reflux at 45°C for 40h, remove the solvent to obtain a crude product, and then use CH 3 OH / CH 2 Cl 2 (v / v=15:1) mixed solvent recrystallization, precipitated solid precipitate, filtered and dried to obtain ligand 4.41g, yield 74%.

[0035] Its reaction formula is as follows:

[0036]

[0037] S2: Synthesis of Catalyst C1:

[0038] in N 2 Under protection, the above ligand (2.78 g, 0.50 mmol) was added to a 100 mL dry flask, followed by PdCl 2 (MeCN) 2 (1.3g, 5mmol) and 30mL CH 2 Cl 2 , stirred at room temperature for 24 h, filtered the suspension, filte...

Embodiment 2

[0042] This embodiment is to prepare the α-diimine palladium catalyst substituted by p-phenyl group, which is denoted as catalyst C2 here, and its specific preparation process is as follows:

[0043] S1: Synthesis of Ligand L2:

[0044] 4-Phenyl-2,6-diethylaniline (4.51g, 20mmol) and 2,3-butanedione (0.90g, 10mmol) were dissolved in 32mL of anhydrous methanol, and 0.27g of formic acid was added under stirring, Reflux the reaction at 20°C for 12h, remove the solvent to obtain a crude product, and then use CH 3 OH / CH 2 Cl 2 (v / v=15:1) mixed solvent recrystallization, precipitated solid precipitate, filtered and dried to obtain ligand 4.90g, yield 75%.

[0045] S2: Synthesis of Catalyst C2:

[0046] in N 2 Under protection, the above ligand (2.80 g, 0.50 mmol) was added to a 100 mL dry flask, followed by PdCl 2 (MeCN) 2 (1.3g, 5mmol) and 30mL CH 2 Cl 2 , stirred at room temperature for 12 h, filtered the suspension, filtered the mixture, and removed the solvent in vacuo....

Embodiment 3

[0050] This embodiment is to prepare the α-diimine palladium catalyst substituted by p-phenyl group, which is denoted as catalyst C3 here, and its specific preparation process is as follows:

[0051] S1: Synthesis of Ligand L3:

[0052] Dissolve 4-benzhydryl-2,6-dimethylaniline (3.95 g, 20 mmol) and 2,3-butanedione (0.83 g, 10 mmol) in 29 mL of anhydrous methanol, and add 0.24 g of Formic acid, reflux at 55°C for 60h, remove the solvent to obtain a crude product, and then use CH 3 OH / CH 2 Cl 2 (v / v=15:1) mixed solvent recrystallization, precipitated solid precipitate, filtered and dried to obtain ligand 4.71g, yield 76%.

[0053] S2: Synthesis of Catalyst C3:

[0054] in N 2 Under protection, the above ligand (2.82 g, 0.50 mmol) was added to a 100 mL dry flask, followed by PdCl 2 (MeCN) 2 (1.3g, 5mmol) and 30mL CH 2 Cl 2 , stirred at room temperature for 48 h, filtered the suspension, filtered the mixture, and removed the solvent in vacuo. The obtained solid was washe...

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Abstract

The invention discloses a p-phenyl substituted alpha-diimine palladium catalyst and a preparation method thereof. The preparation method comprises the following steps: adding a p-phenyl substituted aniline derivative and 2,3-butanedione into a dry flask, carrying out a reflux reaction by taking absolute methanol as a solvent and formic acid as a catalyst to obtain a precipitate, recrystallizing the obtained crude product through a mixed solvent, carrying out filtering, carrying out washing with cold ethanol, and carrying out vacuum drying to obtain a p-phenyl substituted alpha-diimine ligand;and under protection of N2, mixing the p-phenyl substituted alpha-diimine ligand with PdCl2(MeCN)2, adding CH2Cl2, carrying out stirring for reacting, filtering the mixed solution, removing the solvent of the obtained liquid by rotary evaporation, washing the obtained solid with diethyl ether, and finally carrying out vacuum drying to obtain the catalyst. The catalyst disclosed by the invention isapplied to an alpha-olefin polymerization reaction, and polyalpha-olefin (PAO) lubricating oil base oil obtained through a polymer has the advantages of low pour point, high viscosity index and the like, so that the use effect of PAO lubricating oil is greatly improved, and use requirements on the market are met.

Description

technical field [0001] The invention belongs to the technical field of lubricating oil, and in particular relates to a p-phenyl substituted α-diimine palladium catalyst and a preparation method thereof. The catalyst is used to catalyze α-olefin polymerization to prepare PAO lubricating oil base oil. Background technique [0002] With the rapid development of industrial technology, higher requirements are placed on the performance of mechanical equipment. Therefore, the demand for high-performance lubricating oil is also increasing. Poly-α-olefin oil (PAO) is one of the four major types of lubricating oil base oils. Its raw material components and polymerization degree can be adjusted according to actual needs. The obtained polymerization product has low pour point, wide viscosity range, high viscosity index and good oxidation stability. Therefore, lubricating oils synthesized with PAO as base oil quickly occupy the market and the demand is increasing day by day. [0003] A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07F15/00C07C2/32C07C11/02C10M105/04
CPCB01J31/1805C07F15/0066C07C2/32C10M105/04B01J2531/0213B01J2531/824C07C2531/22C07C11/02
Inventor 高琦蒋华良李瑞萍李为民
Owner JIANGSU ZHONGSHENG GAOKE ENVIRONMENTAL CO LTD
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