Catalytic Synthesis of Butene-1 and Hexene-1 in the Homogeneous Oligomerization of Ethylene in the Presence of Nickel Complexes Based on N-Heteroaryl-Substituted α-Diphenylphosphinoglycines

О. S. Soficheva; Софьичева О. С.; G. E. Bekmukhamedov; Бекмухамедов Г. Э.; D. G. Yakhvarov; Яхваров Д. Г.

doi:10.31857/S0453881124010029

Catalytic Synthesis of Butene-1 and Hexene-1 in the Homogeneous Oligomerization of Ethylene in the Presence of Nickel Complexes Based on N-Heteroaryl-Substituted α-Diphenylphosphinoglycines

Authors: Soficheva О.S.¹, Bekmukhamedov G.E.², Yakhvarov D.G.²
Affiliations:
1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences
2. Kazan Federal University
Issue: Vol 65, No 1 (2024)
Pages: 12-21
Section: ARTICLES
URL: https://journals.rcsi.science/0453-8811/article/view/259631
DOI: https://doi.org/10.31857/S0453881124010029
EDN: https://elibrary.ru/HAELEK
ID: 259631

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Abstract

It has been experimentally shown that N-heteroaryl-substituted α-diphenylphosphinoglycines N-(pyrazin-2-yl)-α-diphenylphosphinoglycine, N-(pyridin-2-yl)-α-diphenylphosphinoglycine and N-(pyrimidin-2-yl)-α-diphenylphosphinoglycine obtained by the reaction of three-component condensation of diphenylphosphine, the corresponding primary amine and glyoxylic acid monohydrate are capable in combination with Ni(COD)₂, where COD is cyclooctadiene-1,5, to form active forms of catalysts for selective homogeneous dimerization and trimerization of ethylene with the formation of butene-1 and hexene-1 as the main products. It has been established that the obtained organo-nickel catalytic systems provide a yield of short-chain (C₄–C₆) olefins at the level of 90% with a selectivity for linear α-olefins of 97%. The study of the influence of temperature on the process of homogeneous ethylene oligomerization using the obtained compounds made it possible to establish that the optimal temperature for ethylene oligomerization, providing the highest selectivity to butene-1 and hexene-1, is 80–105°C at the optimum pressure of ethylene is 20–35 atm. Under these conditions, the selectivity for butenes is 71.4–72.6% (selectivity for butene-1 – 69.3–71.1%), for hexenes 20.6–21.2% (selectivity for hexene-1 – 19.2–19.5%), and the optimal duration of the oligomerization process at a temperature 105°C is 1.5 h, which provides the rate of formation of butene-1 equal to 168.1 golig gNi⁻¹h⁻¹) and the rate of formation of hexene-1 – 47.3 golig gNi⁻¹h⁻¹).

Keywords

nickel complexes, oligomerization, ethylene, (Р,О)-ligand, α-phosphinoglycines, diphenylphosphinoamino acids

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