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Latent chiral bridged perfluoroaryl borate compound and preparation thereof

A technology of perfluoroaryl borate and magnesium perfluoroaryl borate, which is applied in the field of organic compounds and its preparation, can solve the problem of structural modification and functional modulation of perfluorophenyl borate without the control of stereoselectivity and other problems, to achieve the effect of increasing adjustable performance, simple synthesis route, and high degree of functionalization

Inactive Publication Date: 2018-10-02
CHINA PETROCHEMICAL TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the structural modification and functional modulation of perfluorophenyl borate have not involved the control of stereoselectivity

Method used

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  • Latent chiral bridged perfluoroaryl borate compound and preparation thereof
  • Latent chiral bridged perfluoroaryl borate compound and preparation thereof
  • Latent chiral bridged perfluoroaryl borate compound and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]Under anhydrous and oxygen-free conditions, 100 mL of solvent n-pentane was added to a 250 mL reaction flask, 2-butyne (0.1 mol, 7.8 mL) was added, and dichloroborane dioxane ( 3M dichloromethane solution, 0.1mol, 33.3mL), reacted for 5h, and obtained 14.6g of the product after removing the solvent, with a yield of 67%. used directly in the next reaction.

[0033] Under anhydrous and oxygen-free conditions, dissolve 0.06 mol (13.2 g) of the obtained product in 100 mL of n-pentane, adjust the temperature to -78 °C, then add 0.3 mol of perfluoroaryllithium reagent, and slowly rise to room temperature to continue the reaction 1- After 48 hours, filter, wash with n-pentane, combine the filtrates, and remove the solvent to obtain 35.2 g of the product, with a yield of 79%. used directly in the next reaction.

[0034] Under anhydrous and oxygen-free conditions, in a 250mL reaction flask, add 100mL of solvent tetrahydrofuran, add 2.1g (0.085mol) of magnesium metal and a catal...

Embodiment 2

[0039] Substitute tetra-n-butylammonium chloride in embodiment 1 with the triethylamine hydrochloride of equimolar quantity, other conditions are the same as embodiment 1, obtain solid 22.1g, be a kind of latex shown in formula (1) Sexually bridged perfluorophenyl borate.

[0040] The spectrogram data is as follows:

[0041] 13 C NMR(125MHz,Common NMR Solvents)δ161.66,155.07,155.69,155.68,155.67,155.65,146.00,146.05,146.02,145.98,136.77,136.76,136.74,136.73,136.48,111.46,70.97,70.96,56.04,45.18 , 31.24, 14.92, 11.26, 10.41.

Embodiment 3

[0043] Substitute tetrahydrofuran in Example 1 with diethyl ether of equal volume, replace the toluene in Example 1 with dichloromethane of equal volume, and other conditions are the same as Example 1, and finally obtain 24.5 g of viscous solid, which is represented by formula (1). A latent chiral bridged perfluorophenyl borate is shown.

[0044] product of 13 C NMR is the same as the product of Example 1.

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Abstract

The invention relates to a kind of latent chiral bridged perfluoroaryl borate compound and preparation thereof. Functionalization degree of the perfluoroaryl borate is greatly increased by introducinglatent chiral bridging groups in the perfluoroaryl borate, and when the perfluoroaryl borate is used as an activator for an olefin polymerization catalyst, an ability to control the stereoselectivityof the olefin polymerization is increased when the symmetry with carrier conjugation is lost. The invention provides a reasonable and effective preparation method of the bridged perfluoroaryl borate.

Description

technical field [0001] The invention relates to organic compounds and their preparation, in particular to a class of latent chiral bridged perfluoroaryl borate compounds and their preparation methods. Background technique [0002] Perfluoroaryl borate is a type of compound with aromatic groups directly attached to the boron atom, and at least 1 to 3 of them are perfluorophenyl groups, and the cations are Li, Na, K and other inorganic ions or organic ammonium ions , This type of compound can be divided into two categories: symmetrical perfluoroaryl borate and asymmetrical perfluoroaryl borate. Due to the weak coordination of the anionic groups of perfluoroaryl borate compounds, this type of compound can be widely used as an important cocatalyst in the synthesis of high-performance single-site catalysts. As for latent chiral bridged perfluoroaryl borate, there are latent chiral carbon atoms in the structure, which can form a chiral center after being combined with the carrier...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 布志捷曹育才宁晓燕王凡刘方涛沈安徐浩夏磊
Owner CHINA PETROCHEMICAL TECH CO LTD