Novel imine compound and preparation method thereof

A compound and imine technology, which is applied in the field of new imine ester compounds and their preparation, can solve the problem of unremarkable catalyst effect

Active Publication Date: 2021-05-07
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There have been many new internal electron donor compounds containing nitrogen atom structures recently, such as maleamide internal electron donor compounds (CN102268109) and hydrazide structure electron donor compounds (CN103539874 and CN103694385), and the electron donor compounds in the diamide structure (US2017 / 0240667), diamine internal electron donor compounds (CN1087918), imine internal electron donor compounds (CN105085733 and CN105085746), amino ester compounds (CN101104589, CN101125896 and CN101172965) and amide esters Internal electron donor compound (US2012322962), but the obtained catalyst effect is not outstanding

Method used

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  • Novel imine compound and preparation method thereof
  • Novel imine compound and preparation method thereof
  • Novel imine compound and preparation method thereof

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Experimental program
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Effect test

Embodiment approach

[0028] According to some embodiments of the present invention, the substituent is selected from halogen, hydroxyl, amino, C 6 -C 20 Aryl, C 7 -C 20 Aralkyl, C 7 -C 20 Alkaryl, C 1 -C 10 Alkyl and C 1 -C 20 Alkoxy, preferably selected from halogen, hydroxy, amino, phenyl, naphthyl, benzyl, phenethyl, C 1 -C 6 Alkyl-substituted phenyl, C 1 -C 10 Alkyl and C 1 -C 20 Alkoxy, more preferably selected from fluorine, chlorine, bromine, iodine, hydroxyl, amino, phenyl, naphthyl, benzyl, phenethyl, methyl, ethyl, isopropyl, n-propyl, n-butyl base, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, methoxy, ethoxy, isopropoxy, n-propoxy, n-butoxy, isobutoxy, tert One or more of butoxy, n-pentyloxy, isopentyloxy, and n-hexyloxy.

[0029] According to some embodiments of the present invention, R 1 and R 2 each independently selected from hydrogen, C with or without substituents 1 -C 20 Alkyl, C with or without substituents 2 -C 20 Alkenyl, C with or without substitue...

Embodiment 1

[0071] The synthesis of embodiment 1 compound benzoic acid (3-benzylidene amino propyl ester)

[0072]

[0073] Method 1: In a 250 ml three-necked flask, add 3.26 g of 3-(benzylidene amino) propanol, 120 ml of THF and 2.15 ml of triethylamine after purging with nitrogen, and add 2.80 g of benzene dropwise at room temperature Formyl chloride, stir well. Stir the reaction for 4 hours, then raise the temperature and reflux for 8 hours. After concentrating under reduced pressure, recrystallize from a mixed solution of diethyl ether / petroleum ether (1:50) to obtain pale yellow crystals, and dry in vacuo to obtain 2.47 g of the product (yield 40%). 1 H-NMR (δ, ppm, TMS, CDCl 3 ):8.13-8.10(1H,m,=CH),7.97-7.94(2H,m,ArH),7.63-7.61(2H,m,ArH),7.46-7.44(1H,m,ArH),7.36-7.34 (2H,m,ArH),7.30-7.28(3H,m,ArH),4.25-4.23(2H,t,OCH 2 ),3.55-3.53(2H,m,=NCH 2 ),2.12-2.10(2H,t,CH 2 ).

[0074] Method 2: In a 250 ml three-necked flask, add 3.58 g of (3-amino)propyl benzoate, 120 ml of isoprop...

Embodiment 2

[0075] The synthesis of embodiment 2 compound benzoic acid [4-(3,5-di-tert-butylbenzylidene amino)-2-pentyl ester]

[0076]

[0077] In a 250 ml three-neck flask, add 3.03 g of 4-(3,5-di-tert-butylbenzylidene amino)-2-pentanol, 120 ml of THF and 1.10 ml of triethylamine after purging with nitrogen 1.40 g of benzoyl chloride was added dropwise at room temperature and stirred evenly. After stirring for 4 hours, the temperature was raised to reflux for 10 hours. After concentrating under reduced pressure, recrystallize from a mixed solution of diethyl ether / petroleum ether (1:50) to obtain light yellow crystals, and dry in vacuo to obtain 2.10 g of the product (yield 51%). 1 H-NMR (δ, ppm, TMS, CDCl 3 ):8.23-8.22(1H,m,=CH),7.99-7.98(2H,m,ArH),7.46-7.44(3H,m,ArH),7.36-7.34(3H,m,ArH),4.20-4.18 (1H,t,OCH),3.35-3.32(1H,t,NCH),2.04-2.03(2H,m,CH 2 ), 1.41-1.39 (3H,d,CH 3 ),1.35-1.32(18H,m,CH 3 ),1.28-1.26(3H,d,CH 3 ).

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Abstract

The invention discloses a novel imine compound and a preparation method thereof. The imine compound has a structure as shown in a formula I and can be used as an internal electron donor compound of an olefin polymerization reaction catalyst, the catalyst is good in hydrogen regulation sensitivity, and the molecular weight distribution of the obtained polymer is wide.

Description

technical field [0001] The invention relates to a novel imine ester compound and a preparation method thereof. Background technique [0002] For traditional Ziegler-Natta catalysts, with the development of electron donor compounds in the catalyst, polyolefin catalysts are constantly updated, and the process technology of polypropylene is also improved. Catalyst research and development from the first / second generation TiCl 3 Alkyl aluminum system to the third generation of magnesium chloride as a carrier, TiCl 4 As the active center, add monoester or aromatic dibasic acid ester as the internal electron donor and silane as the external electron donor of TiCl 4 · ED · MgCl 2 / AlR 3 · In ED system, the catalytic olefin polymerization activity of the catalyst and the high isotacticity of the obtained polypropylene have been greatly improved. In the prior art, most catalyst systems for propylene polymerization use magnesium, titanium, halogen and electron donor as basic comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/24C07C249/02C07C251/08C07C251/18C08F10/00C08F110/06C08F4/649
CPCC07C251/24C07C251/08C07C251/18C08F10/00C08F110/06C08F4/6495C08F2500/03
Inventor 王军马吉星高明智刘海涛马晶蔡晓霞刘文蕊何世雄胡建军李昌秀许景琦
Owner CHINA PETROLEUM & CHEM CORP
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