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The Use of Perfluoroalkanesulfonic Acids in the Palladium-Catalyzed Carbomethoxylation of Olefins

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Catalytic Conversions of Synthesis Gas and Alcohols to Chemicals

Abstract

The incorporation of CO via metal carbonyls into various unsaturated substrates was first developed by Reppe during the thirties and forties [1]. Rohm and Haas, BASF, and Dow Badische have success fully utilized modified Reppe technology in the manufacture of acrylic acid (Equation 1) from acetylene [2]. Using Ni propionate as a

$$ HC \equiv CH + CO + ROH\xrightarrow[{Ni\left( {CO} \right)_4 }]{}H_2 C = CHCO_2 R $$
(1)

catalyst precursor, BASF also produces propionic acid (Equation 2)

$$ H_2 C = CH_2 + CO + ROH \to CH_3 CH_2 CO_2 R $$
(2)

by phosphine-modified palladium(II)-group 4B metal halide complexes [3]. The regioselectivity to the branched isomer, R = CH3, is controlled by both aryl arsine and phosphine-modified palladium(II)-group 4B metal halide complexes [3]. The regioselectivity to the branched isomer, R = CH3, is controlled by both aryl arsine- and phosphine-modified palladium(II) complexes [4,5]. For example, propene yields predominantly (>90 mol %) methyl isobutyrate, a compound of interest as a possible precursor to methyl methacrylate.

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Author information

Authors and Affiliations

  1. Central Research & Development Department, E. I. du Pont de Nemours and Company Experimental Station, Wilmington, Delaware, 19898, USA

    F. J. Waller

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  1. F. J. Waller
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Editor information

Editors and Affiliations

  1. Lehigh University, Bethlehem, Pennsylvania, USA

    Richard G. Herman

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© 1984 Plenum Press, New York

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Waller, F.J. (1984). The Use of Perfluoroalkanesulfonic Acids in the Palladium-Catalyzed Carbomethoxylation of Olefins. In: Herman, R.G. (eds) Catalytic Conversions of Synthesis Gas and Alcohols to Chemicals. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2737-0_11

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  • DOI: https://doi.org/10.1007/978-1-4613-2737-0_11

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4612-9696-6

  • Online ISBN: 978-1-4613-2737-0

  • eBook Packages: Springer Book Archive

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