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A study of ruthenium-based catalysts used in homogeneous transfer hydrogenation of acetophenone

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Języki publikacji
EN
Abstrakty
EN
A detailed comparison of catalytic properties of two different ruthenium-based catalysts in the reaction of homogeneous hydrogenation of acetophenone was performed. Additionally, methods of synthesis of both catalysts were tested and optimized in order to achieve the best possible quality and purity of the final catalysts. NMR analysis was used to analyze and identify the composition of ruthenium compounds and gas chromatography was used to analyze the conversion rate of hydrogenation reactions. It was determined that RuCl2(PPh3)3 obtained with a modified method described by Shaw’s group (Shawet al., 2007) had the best catalytic properties in the reaction performed under conditions described in Liang Wang’s publication (Wang et al., 2014). It was also determined that for concentration ratio of substrate to RuCl2(PPh3)3 amounting to 250:1 the conversion rate was much higher than that of the reaction performed with a double dose of the catalyst. Results of experiments also show that samples of the post-reaction solution should be analyzed right after the reaction, because even if they are stored in low temperature the amount of product can change up to 3–5% compared to the base sample and this change is not predictable. These findings have significant implications for further research of the reaction of homogeneous transfer hydrogenation of ketones. With the right catalysts and methods of their synthesis other parameters of this reaction can be optimized. The most important one is a change of solvent from isopropyl alcohol to a less toxic substance like water. This may increase the value of the reaction in green chemistry and chemical industry.
Rocznik
Strony
213–--222
Opis fizyczny
Bibliogr. 13 poz., rys., tab.
Twórcy
  • Lodz University of Technology, Faculty of Process and Environmental Engineering, 213 Wolczanska Street, 90-924 Łódź, Poland
  • Lodz University of Technology, Faculty of Process and Environmental Engineering, 213 Wolczanska Street, 90-924 Łódź, Poland
Bibliografia
  • 1. Bhanage B.M., Divekar S.S. Deshpande R.M., Chaudhari R.V., 2000. Selectivity in sulfonation of triphenyl phosphine. Org. Process Res. Dev., Organic Process Research & Development, 4, 342–345. DOI: 10.1021/op0000226.
  • 2. Brieger G., Nestrick T.J., 1974. Catalytic transfer hydrogenation. Chem. Rev., 74, 567–580. DOI: 10.1021/cr60291 a003.
  • 3. Cho C.S., Kim B.T., Kim T., Shim S.C., 2001. An unusual type of ruthenium-catalyzed transfer hydrogenation of ketones with alcohols accompanied by C-C coupling. J. Org. Chem., 66, 9020–9022. DOI: 10.1021/jo0108459.
  • 4. Gatsis J.G., 1972. Regeneration of unsupported vanadium sulfide catalyst. American patent, US 3635838A, 18 January 1972.
  • 5. Grzywa E., Molenda J., 2000. Technologia podstawowych syntez organicznych. Tom 2. Wydawnictwa NaukowoTechniczne, Warszawa, 11–121.
  • 6. Herrmann W.A., Brauer G., 2000. Synthetic methods of organometallic and inorganic chemistry. Volume 9: Transition metals Part 3. Thieme Verlagsgruppe, Stuttgart, New York, Delhi, Rio. DOI: 10.1055/b-0035-108457.
  • 7. Houghton R.P., 1985. Kompleksy metali w chemii organicznej. Warszawa, Państwowe Wydawnictwo Naukowe, 248–257.
  • 8. Hurd C.D., Perletz P., 1946. Aryloxyacetones. J. Am. Chem. Soc., 68, 38–40. DOI: 10.1021/ja01205a012.
  • 9. Ryandler P.N., 1979. Catalytic hydrogenation in organic syntheses. Academic Press. Inc., San Diego, 82–88. DOI: 10.1016/B978-0-12-605355-5.50009-4.
  • 10. Shaw A.P., Ryland B.L., Norton J.R., Buccella D., Moscatelli A., 2007. Electron exchange involving a sulphurstabilized ruthenium radical cation. Inorg. Chem., 46, 5805–5812. DOI: 10.1021/ic700580u.
  • 11. Ugo R. (Ed.), 1970. Aspects of homogeneous catalysis. Volume 1. Carlo Manfredi, Milano, 46–48.
  • 12. Vougioukalakis G.C., Grubbs R.H., 2010. Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts, Chem. Rev., 110, 1746–1787. DOI: 10.1021/cr9002424.
  • 13. Wang L., Ma H., Song L., Li L., Wang Y., Wang H., 2014. Transfer hydrogenation of acetophenone in an organic aqueous biphasic system containing double long-chain surfactants. RSC Adv., 4., 1567–1569. DOI: 10.10
Uwagi
PL
Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2019).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-79cf2b3a-90d1-44f4-a0c1-6c1209b2c111
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