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N-Pyrrolylphosphines as ligands for highly regioselective rhodium-catalyzed 1-butene hydroformylation: effect of water on the reaction selectivity

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Abstract

The hydroformylation of 1-butene catalyzed by Rh(acac)(CO)2 with an excess of N-pyrrolylphosphine ligands, L = P(NC4H4)3, PPh2(NC4H4) or PPh(NC4H4)2, was investigated under constant pressure of synthesis gas (4–10 bar, H2/CO = 1) and 2 bar of 1-butene at temperatures ranging from 50 to 80 °C. N-Pyrrolylphosphine ligands facilitated excellent selectivity towards aldehydes and regioselectivity towards linear aldehydes. The application of a higher temperature, the presence of a small amount of water, and a [L]/[Rh] ratio of ca. 13 resulted in the achievement of the highest n/iso values in a short time. A further increase in selectivity was achieved after the addition of water to the reaction mixture. The catalytic performance of the studied systems showed an increase in selectivity (n/iso) with the increase of the number of pyrrolyl groups in phosphine: (P(NC4H4)3 > PPh(NC4H4)2 > PPh2(NC4H4)) > PPh3.

Graphical abstract: N-Pyrrolylphosphines as ligands for highly regioselective rhodium-catalyzed 1-butene hydroformylation: effect of water on the reaction selectivity

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Publication details

The article was received on 01 Feb 2017, accepted on 05 Jun 2017 and first published on 06 Jun 2017


Article type: Paper
DOI: 10.1039/C7CY00200A
Citation: Catal. Sci. Technol., 2017, Advance Article
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    N-Pyrrolylphosphines as ligands for highly regioselective rhodium-catalyzed 1-butene hydroformylation: effect of water on the reaction selectivity

    W. Alsalahi, R. Grzybek and A. M. Trzeciak, Catal. Sci. Technol., 2017, Advance Article , DOI: 10.1039/C7CY00200A

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