Binuclear xanthene bridging amino-pyridine nickel catalyst and preparation method and application thereof

A technology for bridging amine groups and nickel catalysts is applied in the field of catalysis, which can solve the problems of high reaction temperature and high production cost, and achieve the effects of high catalytic activity, low production cost and low cost.

Active Publication Date: 2018-04-13
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Most of the above pour point depressants are ester polymers or copolymers of esters and

Method used

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  • Binuclear xanthene bridging amino-pyridine nickel catalyst and preparation method and application thereof
  • Binuclear xanthene bridging amino-pyridine nickel catalyst and preparation method and application thereof
  • Binuclear xanthene bridging amino-pyridine nickel catalyst and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of 9,9-dimethyl-9-xanthane-4,4′-bis[2-(2,6-diisopropyl)aniline-2-ethyl]pyridine, the reaction formula is as follows.

[0033]

[0034] Take xanthene diboronic acid (1.0g, 3.4mmol), 1,6-diisopropyl-p-bromoaniline (2.6g, 10.0mmol), sodium carbonate (1.0g, 9.4mmol), Pd (dba) 2 (0.2g, 0.35mmol), triphenylphosphine (0.1g, 0.4mmol), H 2 O (4mL), ethanol (7mL) and toluene (24mL) were mixed, stirred overnight at room temperature, after the reaction stopped, extracted with ethyl acetate, washed with sodium chloride, dried with magnesium sulfate, spin-dried the solvent, and added 10mL of methanol Recrystallized, filtered, and dried to obtain off-white solid 9,9-dimethyl-9-xanthene-4,4'-bis(2,6-diisopropyl)aniline (i.e., diamine compound C) (1.0g ,54%).

[0035] Take 9,9-dimethyl-9-xanthene-4,4'-bis(2,6-diisopropyl)aniline (1.0g, 1.79mmol), 2-pyridinecarbaldehyde (1.30g, 12.1mmol) And 0.05 equivalent of p-toluenesulfonic acid, dissolved in toluene (30mL), refluxed ...

Embodiment 2

[0038] Synthesis of 9,9-dimethyl-9-xanthane-4,4′-bis[2-(2,6-dimethyl)aniline-2-ethyl]pyridine, the reaction formula is as follows.

[0039]

[0040]

[0041] The procedure is the same as above, and 1,6-dimethyl-p-bromoaniline (2.0g, 10mmol) is added to finally obtain 9,9-dimethyl-9-xanthene-4,4'-bis[2-(2,6- Dimethyl)aniline-2-ethyl]pyridine, 84% (1.01 g). 1H NMR (500MHz, CDCl3, ppm): δ8.44(m, 2H, pydine-H), 7.33(m, pydine-H), 7.19(d, J=7.4Hz, 2H, pydine-H), 7.01( d,J=8.0Hz,4H,pydine-H,aryl-H),6.9(m,4H,aryl-H),6.80(s,4H,aryl-H),4.31(m,4H,CHCH3),3.94 (s,2H,NH),1.86(s,12H,aryl-CH3),1.53(m,6H,xanthene-CH3),1.36(m,6H,CHCH3);13C{1H}NMR(125MHz,CDCl3,ppm ):δ164.2,149.2,147.5,143.9,136.2,130.4,130.2,130.0,128.8,128.4,124.2,122.7,121.9,121.3,57.8(CHCH3),34.4(C(CH3)2),32.3(C(CH3) 2), 23.1 (CHCH3), 18.8 (aryl-CH3); HRMS (m / z): calcd for C45H47N4O: 659.3750; found: 659.4578 [M+H]+.

Embodiment 3

[0043] Synthesis of 9,9-Dimethyl-9-xanthene-4,4′-bis[2-(2,6-diisopropyl)aniline-2-ethyl]pyridine nickel complex (Ni-A) .

[0044]

[0045] Take (DME)NiBr 2 (0.17g, 0.54mmol) and 9,9-dimethyl-9-xanthen-4,4′-bis[2-(2,6-diisopropyl)aniline-2-ethyl]pyridine (0.21 g, 0.27mmol) into the Schlenk flask, add CH 2 Cl 2 (20 mL), the mixture was stirred at room temperature for 12 hours. The resulting suspension was filtered, the solvent was spin-dried, and the obtained powder was washed with diethyl ether (2×10 mL), and then vacuum-dried at room temperature to obtain a brown solid, which was Ni-A (0.21 g, 67%). Elemental analysis results: C, 52.78; H, 5.01; N, 4.65; found: C, 52.38; H, 4.69; N, 4.57; M–2Br]+.

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Abstract

The invention relates to a novel binuclear xanthene bridging amino-pyridine nickel catalyst and a preparation method thereof. The novel binuclear xanthene bridging amino-pyridine nickel catalyst is used for catalyzing ethylene polymerization to prepare polyethylene which is low in polymerization degree and high in branching degree. The binuclear nickel catalyst has the advantages that the catalystis high in thermal stability and catalytic activity and capable of effectively regulating the molecular weight and branching degree of polyethylene, and the prepared polyethylene which is low in polymerization degree and high in branching degree can be used as a diesel oil pour point depressant and can effectively lower the condensation point and cold filter plugging point of diesel oil.

Description

technical field [0001] The invention belongs to the field of catalysis, and in particular relates to a dinuclear xanthene-bridged amino-nickel pyridine catalyst and a preparation method and application thereof. Background technique [0002] The main reason why diesel oil loses fluidity at low temperature is that the wax in diesel oil crystallizes out and forms wax crystals. These wax crystals grow rapidly and bond into a network skeleton structure to wrap the diesel oil inside, thus making it lose its fluidity. After adding an appropriate amount of pour point depressant, although it cannot prevent the precipitation of wax, it can change the size and shape of wax and weaken the ability of wax crystals to form a network structure, thereby improving the flow performance of diesel oil. [0003] At present, there are few varieties of diesel pour point depressants developed in China. Feng Lijuan et al. Four kinds of alkyl acrylate-vinyl acetate-styrene terpolymers with different...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07C2/22C07F15/04C07C11/02C08F10/02C08F4/80C10L1/16C10L10/14
CPCB01J31/1815B01J2231/20B01J2531/0241B01J2531/847C07C2/22C07F15/045C08F10/02C10L1/1633C10L10/14C07C11/02C08F4/80Y02P20/52
Inventor 李为民戎春勇孙进龙王福周陈昶乐
Owner CHANGZHOU UNIV
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