Hydrogenation of terminal and internal olefins using a biowaste-derived heterogeneous cobalt catalyst by Florian Korbinian Scharnagl, Maximilian Franz.

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Presentation transcript:

Hydrogenation of terminal and internal olefins using a biowaste-derived heterogeneous cobalt catalyst by Florian Korbinian Scharnagl, Maximilian Franz Hertrich, Francesco Ferretti, Carsten Kreyenschulte, Henrik Lund, Ralf Jackstell, and Matthias Beller Science Volume 4(9):eaau1248 September 21, 2018 Copyright © 2018 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC).

Scheme 1 Recycling of Co@Chitosan-700 in the hydrogenation of 1-octene. Recycling of Co@Chitosan-700 in the hydrogenation of 1-octene. General conditions: 1.5 mmol 1-octene, 1.5 ml of H2O, 2.9 mol % of Co@Chitosan-700, 60°C, 10 bar H2, 18 hours. Florian Korbinian Scharnagl et al. Sci Adv 2018;4:eaau1248 Copyright © 2018 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC).

Fig. 1 Characterization of fresh and recycled Co@Chitosan-700 by HAADF-STEM. Characterization of fresh and recycled Co@Chitosan-700 by HAADF-STEM. Images of fresh (A and B) and nine times–used (C and D) Co@Chitosan-700 catalyst, giving an overview on the general morphology. Florian Korbinian Scharnagl et al. Sci Adv 2018;4:eaau1248 Copyright © 2018 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC).

Scheme 2 Olefin hydrogenation with Co@Chitosan-700: Investigation of functional group tolerance. Olefin hydrogenation with Co@Chitosan-700: Investigation of functional group tolerance. General conditions: 1.5 mmol substrate, 2.9 mol % (8.8 mg) of catalyst with respect to Co, 1.5 of ml H2O. Yields were determined via 1H NMR using mesitylene as internal standard. Isolated yields are given in parentheses. aYield was determined via gas chromatography (GC) using hexadecane as internal standard. bYields were determined via 13C NMR using mesitylene as internal standard. cReaction was conducted in methanol. dReaction was conducted neat. Florian Korbinian Scharnagl et al. Sci Adv 2018;4:eaau1248 Copyright © 2018 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC).

Scheme 3 Olefin hydrogenation with Co@Chitosan-700: Investigation of aromatic mono- and disubstituted substrates. Olefin hydrogenation with Co@Chitosan-700: Investigation of aromatic mono- and disubstituted substrates. General conditions: 1.5 mmol substrate, 2.9 mol % (8.8 mg) of catalyst with respect to Co, 1.5 ml of H2O. Yields were determined via 1H NMR using mesitylene as internal standard. Florian Korbinian Scharnagl et al. Sci Adv 2018;4:eaau1248 Copyright © 2018 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC).

Scheme 4 Olefin hydrogenation with Co@Chitosan-700: Investigation of industrially relevant unsaturated hydrocarbons. Olefin hydrogenation with Co@Chitosan-700: Investigation of industrially relevant unsaturated hydrocarbons. General conditions: 1.5 mmol substrate, 2.9 mol % (8.8 mg) of catalyst with respect to Co, 1.5 ml of H2O. Yields were determined via GC using hexadecane as internal standard. aReaction was carried out on a 10-ml scale (7.2 g, 64 mmol) without additional solvent. Isolated yield is given. bYields were determined via 1H NMR using mesitylene as internal standard. cReaction was carried out on a 5-ml scale (3.5 g, 42.1 mmol) without solvent. Florian Korbinian Scharnagl et al. Sci Adv 2018;4:eaau1248 Copyright © 2018 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC).

Scheme 5 Hydrogenation of fatty acids and esters. Hydrogenation of fatty acids and esters. Hydrogenation of (A) oleic acid and its triglyceride triolein and (B) sunflower oil. General conditions: (A) 1.5 mmol substrate, 2.9 mol % (8.8 mg) of catalyst with respect to Co, 0.5 ml of solvent if used, 150°C, 40 bar H2, 18 hours; (B) 30 ml (25.68 g) of substrate, 100 mg of catalyst, 150°C, 40 bar H2, 19 hours. Conversions were determined via 1H NMR using mesitylene as internal standard. Florian Korbinian Scharnagl et al. Sci Adv 2018;4:eaau1248 Copyright © 2018 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC).