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Pyridylimine group complex containing asymmetric fused rings and preparation method and application of pyridylimine group complex

A kind of compound and cycloalkyl technology, applied in the field of asymmetric condensed ring pyridineimine complex and preparation thereof

Active Publication Date: 2019-10-29
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

We have missed the competition opportunities of Ziegler-Natta catalytic system and metallocene catalytic system, and are surrounded by foreign patented technology

Method used

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  • Pyridylimine group complex containing asymmetric fused rings and preparation method and application of pyridylimine group complex
  • Pyridylimine group complex containing asymmetric fused rings and preparation method and application of pyridylimine group complex
  • Pyridylimine group complex containing asymmetric fused rings and preparation method and application of pyridylimine group complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114] Example 1 Preparation of Formula VI-1 Intermediate 7,8,9,10-tetrahydro-6H-cycloheptaquinoline compound

[0115]

[0116] With 123.0g (1.0mol) o-aminobenzyl alcohol represented by IV-1 formula, 136.8g (1.20mol) V-1 cycloheptanol and 134.4g (1.20mol) potassium tert-butoxide and 380mg (0.5mmol) Ru-cat .Dissolved in a mixed solution of 150mL tetrahydrofuran and 750mL toluene, under nitrogen atmosphere, at 120°C, stirred and refluxed for 72h. TLC detects that the reaction is complete. Cool to room temperature, remove tetrahydrofuran and toluene under reduced pressure to obtain a brown oil, add 200mL of water to it, stir for 0.5h, then extract with ethyl acetate (2×400mL), combine the organic phases, wash with deionized water (2×100mL ) and washed with anhydrous Na 2 SO 4 After drying and filtering, the solvent was removed from the filtrate to obtain 180g of red oil, which was dissolved in dichloromethane (100mL), and then a large amount of n-hexane (300mL) was added, a...

Embodiment 2

[0122] Example 2 Preparation of Formula VII-1 Intermediate 2,3,4,6,7,8,9,10-octahydro-1H-cycloheptaquinoline compound

[0123]

[0124] 145.0g (0.73mol) formula VI-1, 14.5g (10%) Pd / C and 500mL trifluoroacetic acid are put into 1000mL stainless steel alloy autoclave, replace with hydrogen three times, under 40bar H 2 Under pressure, at 80°C, the reaction was stirred for 24h. Stop the reaction, release excess hydrogen, filter the reaction solution, distill the filtrate to remove trifluoroacetic acid to obtain a yellow oil, add 10% NaOH aqueous solution, adjust pH≈14, extract with dichloromethane (2×100mL), and use anhydrous Na 2 SO 4 Drying, filtering to obtain a light yellow liquid, and distilling off the solvent to obtain 118.0 g of 2,3,4,6,7,8,9,10-octahydro-1H-cycloheptaquinoline compound shown in formula VII-1. The yield is 80%, melting point: 45–46°C.

[0125] The structural confirmation data are as follows:

[0126] 1 H NMR (500MHz, CDCl 3 )δ7.08(s,1H),3.01–2.9...

Embodiment 3

[0130] Example 3 Preparation of intermediate 2,3,7,8,9,10 hexahydro-1H-cycloheptaquinoline-4,6-dione compound represented by formula II-1

[0131]

[0132] 2,3,4,6,7,8,9,10-octahydro-1H-cycloheptaquinoline compound represented by 60.0g (0.30mol) VII-1 formula was dissolved in 318.0g (3.00mol) benzene Formaldehyde and 240.0 g (2.40 mol) of acetic anhydride were reacted under reflux at 180° C. for 72 h under a nitrogen atmosphere. After the reaction was detected by TLC, it was cooled to room temperature, and a vacuum distillation device was set up, and the reaction solution was subjected to vacuum distillation (100° C., 10 mm Hg) to remove unreacted benzaldehyde, acetic anhydride, and by-products. After vacuum distillation, the brown oil was dissolved in 1200 mL of dichloromethane. The reaction solution was cooled to below -40°C and passed through dry O 3 / O 2 , carry out ozonation reaction until the solution turns light yellow or light blue, react for about 3 hours, TLC d...

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Abstract

The invention provides a pyridylimine group complex containing asymmetric fused rings and a preparation method and application of an intermediate of the pyridylimine group complex. The complex has high catalytic activity, can realize the regulation of the molecular weight of a polymer by changing a ligand structure and polymerization conditions, and has the advantages such as low cost and stable performance. The preparation method of the intermediate 2,3,7,8,9,10 hexahydro-1H-cycloheptaquinoline-4,6-dione compound and the complex has the advantages such as mild conditions, short cycle and simple operating conditions. The complex can be applied to a catalyst for ethylene polymerization, especially when an iron complex provided has high thermal stability, the catalytic activity can be as high as 15.86x10<6> g.mol<-1>(Fe)h<-1> under the action of a catalyst promoter MMAO, highly linear polyethylene is obtained, the catalytic activity can still be maintained at 5.44x10<6> g.mol<-1>(Fe)h<-1> even at a high temperature of 90 DEG C, the temperature is in line with the operating temperature of industrial production, and the pyridylimine group complex has good industrial application prospects.

Description

technical field [0001] The invention relates to the technical field of polyolefin catalysts, in particular to complexes containing asymmetric fused ring pyridyl imine groups and their preparation methods and applications. Background technique [0002] Polyethylene (PE) is the variety with the largest output among the general-purpose synthetic resins in the world, and occupies a pivotal position in the field of synthetic olefin materials. Polyethylene not only has the advantages of high cost performance, good mechanical properties, and excellent processing properties, but also has stable thermal and chemical properties, so it is widely used in various fields of national economy such as daily life, medical care, agriculture, industry, and military affairs. The olefin polymerization catalyst is the key to research in the field of polyethylene, and its development and structure determine the performance of polyolefin. Throughout the industrial development history of polyolefins...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/02C07F15/04C07F15/06C07F13/00C08F10/00C08F110/02C08F4/70
CPCC07F13/005C07F15/025C07F15/045C07F15/065C08F4/7042C08F10/00C08F110/02Y02P20/52
Inventor 王征马艳平孙文华
Owner INST OF CHEM CHINESE ACAD OF SCI
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