Abstract
Alcohols were obtained by the one-stage hydroformylation of olefins from the hydrocarbon fraction C6–C9, which was produced in the Fischer—Tropsch synthesis followed by the hydrogenation of aldehydes yielded by the hydroformylation products. The process is carried out on the cobalt catalyst modified by tertiary phosphines under the synthesis gas pressure 85 bar and temperature 180 °C. The role of the solvent is performed by paraffins of the hydrocarbon fraction from the Fischer—Tropsch synthesis. Cobalt acetylacetonate Co(acac)2, acetate Co(OAc)2, and carbonate CoCO3 can serve as catalyst precursors. The complexes with bulky and basic phosphines were shown to possess satisfactory activity and high selectivity to alcohols. Tricyclohexyl- and triphenylphosphines are the most promising for the implementation of the process. The full conversion is achieved within 8 h at the cobalt concentration ∼0.2 wt.%: the residual olefin content is <1% and the selectivity to alcohols is ⩾97%.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
B. Cornils, in New Synthesis with Carbon Monoxide, Ed. J. Falbe, Springer-Verlag, Berlin—Heidelberg—New York, 1980, p. 1.
P. Pino, F. Piacenti, M. Bianchi, in Organic Synthesis via Metal Carbonyls, Eds I. Wender, P. Pino, Willey-Interscience, New York, 1977, 2, p. 43.
RF Patent No. 2 493 913; Byul. Izobret. [Invention Bulletin], 2013, 27 (in Russian).
EN ISO 22854/ASTM D 6839; https://www.iso.org/standard/68966.html; https://www.astm.org/Standards/D6839.html.
US Pat. 3400163; Chem. Abstrs, 1974, 80, 146299.
A. R. Manning, J. Chem. Soc. (A), 1968, 1135.
RF Patent No. 2 581 191; Byul. Izobret. [Invention Bulletin], 2016, 11 (in Russian).
W. A. Henderson, C. A. Streuli, J. Am. Chem. Soc., 1960, 82, 5791.
T. Allman, R. G. Goel, Canad. J. Chem., 1982, 60, 716.
C. A. Tolman, Chem. Rev., 1977, 77, 313.
A. C. Comely, S. E. Gibson, N. J. Hales, C. Johnstone, A. Stevenazzi, Org. Biomol. Chem., 2003, 1, 1959.
P. Szabo, L. Fekete, G. Bor, Z. Nagy-Magos, L. Marko, J. Organomet. Chem., 1968, 12, 245.
K. Y. Lee, J. K. Kochi, Inorg. Chem., 1989, 28, 567.
E. J. Moor, J. M. Sullivan, J. R. Norton, J. Am. Chem. Soc., 1986, 108, 2257.
M. Abshi-Halabi, J. B. Atwood, N. P. Forbus, T. L. Brown, J. Am. Chem. Soc., 1980, 102, 6248.
D. G. Gorenstein, Progr. Nucl. Magn. Reson. Spectr., 1983, 16, 35.
O. Kühl, Phosphorus-31 NMR Spectroscopy: A Concise Introduction for the Synthetic Organic and Organometallic Chemist, Springer-Verlag, Berlin—Heidelberg, 2008, p. 86.
J. Schraml, M. Capka, V. Blechta, Magn. Reson. Chem., 1992, 30, 544.
O. Kühl, Phosphorus-31 NMR Spectroscopy: A Concise Introduction for the Synthetic Organic and Organometallic Chemist, Springer-Verlag, Berlin—Heidelberg, 2008, p. 32.
Comprehensive Coordination Chemistry. II. From Biology to Nanotechnology, Eds J. A. McCleverty, T. J. Meyer, Elsevier, Amsterdam, 2005, 6, p. 13.
Spectral Database for Organic Compounds; http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi (date of treatment 04.06.2018).
RF Patent No. 2 602 239; Byul. Izobret. [Invention Bulletin], 2016, 31 (in Russian).
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1662–1668, September, 2019.
Rights and permissions
About this article
Cite this article
Noskov, Y.G., Kron, T.E., Karchevskaya, O.G. et al. Hydroformylation of olefins produced in the Fischer—Tropsch synthesis. Russ Chem Bull 68, 1662–1668 (2019). https://doi.org/10.1007/s11172-019-2609-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-019-2609-x