Synthesis of Branched α-Olefins via Trimerization and Tetramerization of Ethylene

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Lukas, Fabian ; Simon, Paula A. ; Dietel, Thomas ; Kretschmer, Winfried ; Kempe, Rhett:
Synthesis of Branched α-Olefins via Trimerization and Tetramerization of Ethylene.
In: Advanced Science. Bd. 11 (2024) Heft 38 . - 2405653.
ISSN 2198-3844
DOI der Verlagsversion: https://doi.org/10.1002/advs.202405653

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Abstract

α-Olefins are very important bulk and fine chemicals and their synthesis from ethylene, an abundantly available and inexpensive feedstock, is highly attractive. Unfortunately, the direct or on-purpose synthesis of olefins from ethylene is limited to three examples, 1-butene, 1-hexene, and 1-octene, all having a linear structure. Herein, the direct synthesis of 3-methylenepentane and 4-ethylhex-1-ene, branched trimerization, and tetramerization products of ethylene, respectively, is reported. Different molecular titanium catalysts, all highly active, with a selectivity toward the formation of the branched ethylene trimer or tetramer, the employment of different activators, and different reaction conditions are the key to selective product formation. The long-time stability of selected catalysts employed permits upscaling as demonstrated for the synthesis of 4-ethylhex-1-ene (52 g isolated, TON(ethylene) 10.7 · 10⁶).