Catalysis systems for preparing highly branched alkane by using olefin

An alkyl and compound technology, applied in the preparation of sulfides, imino compounds, organic chemistry, etc., can solve problems such as inability to meet requirements, lack of methods and catalytic systems, etc.

Active Publication Date: 2012-11-21
NANJING CHEMRUN CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The polyethylene obtained by Brookhart et al. from nickel-based catalysts has a certain degree of branching, but still cannot meet the requirements, showing that the product is in a solid state
[0006] In summary, there is still a lack of satisfactory methods and catalytic systems for the direct preparation of highly branched oily polymers from ethylene.

Method used

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  • Catalysis systems for preparing highly branched alkane by using olefin
  • Catalysis systems for preparing highly branched alkane by using olefin
  • Catalysis systems for preparing highly branched alkane by using olefin

Examples

Experimental program
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preparation example Construction

[0123] Preparation of Ligand Compounds and Complexes

[0124] The present invention also provides the synthesis of the ligand compound of formula I, comprising steps:

[0125] (a) C is obtained by reacting the corresponding diketone A with an amine compound B.

[0126] (b) Ligand I is obtained by reacting C with amine compound D.

[0127] Described compound A, B, C, D have the following structural formula:

[0128]

[0129] The reaction needs to add 0.001-100% corresponding catalysts to promote the condensation reaction, such as acetic acid, p-toluenesulfonic acid, TiCl 4 , orthosilicate, etc. Specifically, diketone A and amine B are firstly mixed in an inert solvent, and activated by 0.001-100% acetic acid to generate monoimine C, and C continues to react with amine D to obtain the product represented by formula (I). Described inert solvent can be all solvents commonly used in condensation reaction, comprises alcohol, aromatic hydrocarbon, aliphatic hydrocarbon, haloge...

Embodiment 1

[0182] Synthesis of Ligand L1a

[0183]

[0184] In a 100mL egg-shaped flask, add 3.644g (20mmol) of acenaphthoquinone, add 40mL of methanol, add 4.0mL (20mmol) of 2,6-diisopropylaniline, add 2 drops of anhydrous acetic acid, stir at room temperature, and track the reaction by TLC to End, concentrated under reduced pressure, neutral alumina column chromatography, EA: PE = 1: 20-EA: PE = 1: 10 to obtain the orange-yellow product monoimine, the yield is 60%. 1 HNMR (300MHz, CDCl 3 ): δ=8.21(2H, m), 8.01(1H, d), 7.82(1H, t), 7.41(1H, t), 7.27(3H, s), 6.64(1H, d), 2.84(2H, m), 1.18(6H,d), 0.90(6H,d).

[0185] In a 100mL egg-shaped bottle, add 1.708g (5.0mmol) of monoimine, add 40mL of methanol, add 7.5mmol of aniline, add 2 drops of anhydrous acetic acid, stir at room temperature, follow the reaction to the end by TLC, concentrate under reduced pressure, neutral alumina Column chromatography, EA:PE=1:15 gave the orange-yellow product L1a. 1 H NMR (300MHz, CDCl 3 ): δ=7.88-...

Embodiment 2

[0187] Synthesis of Ligand L1b

[0188]

[0189] According to the synthesis method of ligand L1a in Example 1, the second step was to replace aniline with 2,6-dichloroaniline, and the other operating conditions were the same to obtain an orange solid. 1 H NMR (300MHz, CDCl 3 ): δ=8.32(1H, d), 8.10(1H, d), 7.96(1.5H, m), 7.53(2H, d), 7.41(3H, m), 7.38(2H, m), 6.91(0.5 H, m), 6.58 (1H, t), 2.77 (2H, m), 1.29 (2H, d), 0.97 (10H, d), 13 C NMR (75MHz, CDCl3): δ = 162.2, 157.8, 146.1, 133.1, 130.7, 127.5, 124.8, 124.4, 124.3, 123.39, 123.1, 122.7, 120.7, 77.4, 77.6, 28.5, 27.9, 23.5, 22.8. IR(KBr):v(cm -1 )=3052, 2960, 2923, 2865, 1674, 1640, 1602, 1463, 1433, 1242, 1077, 1033, 831, 779, 760, 730; C 30 h 26 Cl 2 N 2 (484.45): Anal. Calc. C 74.22, H 5.40, N 5.77; Found C 73.99, H 5.39, N 5.65.

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Abstract

The present invention discloses a class of catalysis systems for preparing highly branched alkanes by using olefins. The catalysis systems comprise a class of novel nickel complexes and palladium complexes. With effects of the catalysis systems, only mild conditions are required to efficiently obtain oily highly branched alkane mixtures by using ethylene and other olefins, wherein the alkane mixtures have a low bromine value, and can be used for processing aids, and high-performance base oil of lubricants,. The present invention further provides a preparation method for catalysts, and a preparation method for oily olefin polymers.

Description

technical field [0001] The present invention relates to the field of catalysis and base oil of lubricating oil, in particular to a class of α-diimine nickel and palladium catalysts and their preparation technology, and under the action of such catalysts, the direct preparation of oily high Method for branching alkanes. Background technique [0002] The base oil of lubricating oil in industry is a mixture of various branched alkanes, obtained by petroleum cracking or α-olefin oligomerization (PAO). Among them, PAO, as a very important class of lubricant base oil with excellent performance, is obtained through oligomerization of α-olefins, and the main raw materials are α-octene, α-decene, α-dodecene and other expensive high-grade α - Alkenes. [0003] Therefore, the prerequisite for obtaining high-quality base oil PAO is to first catalyze the oligomerization of ethylene to obtain α-olefins, especially α-decene. It is technically difficult to selectively produce α-olefins a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/20C07C251/24C07C249/02C07C321/30C07C321/20C07C319/20C07F15/04C07F15/00C07F19/00C08F4/26C08F110/02C08F110/06C08F110/08C08K5/01C10G50/02
Inventor 唐勇陶闻杰孙秀丽李军方
Owner NANJING CHEMRUN CO LTD
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