Highly Efficient Hydrogenation of Levulinic Acid into γ‐Valerolactone using an Iron Pincer Complex

Yi, Yuxuan; Liu, Huiying; Xiao, Ling‐Ping; Wang, Bo; Song, Guoyong

doi:10.1002/cssc.201800435

Cited by 38 publications

(24 citation statements)

References 63 publications

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“…However, various homogeneous catalysts recently have entered the spotlights by displaying high activities and excellentor at least tunableselectivity towards GVL. Among the homogeneous examples some outstanding turn-over numbers (TON) up to 174 000 have been reported for catalysts based on ruthenium 15 and iridium 16 predominantly, while iron 17 has recently made its debut.…”

Section: Introductionmentioning

confidence: 99%

Solvent-free hydrogenation of levulinic acid to γ-valerolactone using a Shvo catalyst precursor: optimization, thermodynamic insights, and life cycle assessment

et al. 2020

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Section: Introductionmentioning

confidence: 99%

Solvent-free hydrogenation of levulinic acid to γ-valerolactone using a Shvo catalyst precursor: optimization, thermodynamic insights, and life cycle assessment

et al. 2020

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“…In this one‐pot ‘two‐step’ process, acid and hydrogenation catalysts were loaded together. No separation and/or neutralization step reported in the literature was needed, which greatly simplified the process for GVL production from biomass. Thus, in all the following experiments, the one‐pot ‘two‐step’ process was adopted.…”

Section: Resultsmentioning

confidence: 99%

“…The common approach for the conversion of carbohydrate to GVL is multistep and energy‐intensive. Before the hydrogenation process, separation of LeA or levulinate from the acidic aqueous solution, neutralization of the acidic solution with alkali or alkaline‐oxide, or filtration to remove solid by‐products, are needed. For example, cellulose was first hydrolyzed to LeA in sulfuric acid (H 2 SO 4 ) aqueous solution, subsequently esterification and separation of levulinate from the acidic solution using 1‐butanol before the hydrogenation process on Au/ZrO 2 .…”

Section: Introductionmentioning

confidence: 99%

One‐pot conversion of carbohydrates into γ‐valerolactone under the coordination of heteropoly acid based ionic liquid and Ru/ZrO₂ in water media

Ren

Zhu

et al. 2019

J of Chemical Tech & Biotech

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BACKGROUND: The chemical catalytic conversion of carbohydrates into -valerolactone (GVL) is a sustainable alternative to the petrochemical process starting from the depleting fossil resources. Direct conversion of carbohydrates (fructose, glucose, starch and cellulose) into GVL was achieved via the combined heteropoly acid based SO 3 H-functionalized ionic liquid (HAIL) and supported ruthenium (Ru) catalyst system in one pot and in water media. RESULTS: A 63% GVL yield (based on fructose) was obtained under the catalysis of 1-methyl-3-(3-sulfopropylimidazolium) silicotungstate ([MIMPS] 4 SiW) and Ru/ZrO2 at 180 ∘ C, first in 0.1 MPa nitrogen (N 2 ) for 3 h (dehydration), and then in 4 MPa hydrogen (H 2 ) for 10 h (hydrogenation). Under the same reaction conditions, the GVL yields from glucose, starch and cellulose were 68%, 60% and 60%, respectively. The recyclability of the catalytic system consisting of [MIMPS] 4 SiW and Ru/ZrO 2 was investigated in four runs. The activity for [MIMPS] 4 SiW did not change after use. Partial deactivation of Ru/ZrO 2 was observed, which was ascribed to the severe carbon deposition.CONCLUSIONS: In the present method, HAIL and Ru/ZrO 2 catalysts were loaded together. No separation and/or neutralization step reported in the literature was needed and only an atmosphere change (from N 2 to H 2 ) step was involved. Therefore, we provide a promising method for efficient conversion of carbohydrates into GVL.

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“…Based on these promising results, Song et al described an efficient and useful application of the iron‐catalysed hydrogenation for the conversion of levulinic acid (LA) to γ‐valerolactone (GVL) (Scheme ) …”

Section: Multi‐step Reactions Involving Iron‐catalysed Hydrogenationmentioning

confidence: 99%

Multi‐Step Reactions Involving Iron‐Catalysed Reduction and Hydrogen Borrowing Reactions

2019

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Iron catalysis has seen an impressive breakthrough during the last two decades, and iron can now be considered as a valuable alternative transition metal for organic synthetic transformations. More precisely, in the reduction area, it became an efficient player for the selective reduction of olefins, alkynes, carbonyl and carboxylic derivatives, imines and nitro [a] Sortais. His work focuses on the homogeneous iron, manganese and rhenium-catalysed reduction and dehydrogenation reactions. Chakkrit Netkaew (left) was born in Nakhon Sawan, Thailand, in 1992. He completed his Bachelor's degree in Chemistry in 2017 from Mahidol University in Bangkok, Thailand, under the supervision of Assoc. Prof. Pasit Pakawatpanurut. After his graduation, he received a Franco-Thai scholarship 2018 from the French Embassy to attend the International Master's Program (Catalysis, Molecules and Green Chemistry) at the University of Rennes 1. Currently, he is carrying out research on the homogeneous iron-catalysed reduction reactions in Prof. C. Darcel's team. Prof. Christophe Darcel (centre) grew up in the north coast of Britany and studied chemistry at the University of Rennes 1, where he obtained his PhD in 1995 under the joint-supervision of Dr. Christian Bruneau and Prof. Pierre H. Dixneuf on Ru-and Pd-catalysed transformations of functional alkynes. After a year's postdoctoral stay with Prof. Wolfgang Oppolzer (Switzerland) working on sultam stereoselective chemistry and application in natural products synthesis, he then joined the group of Prof. Paul Knochel in Marburg (Germany) as an Alexander von Humboldt postdoctoral fellow and worked on the development of chiral zinc derivatives. In 1997, he was then appointed at the University of Cergy-Pontoise as assistant professor, and at the University of Burgundy as associate professor developing in collaboration with Prof. Sylvain Jugé P-chirogenic ligands for asymmetric catalysis. In 2007, he became full professor at the University of Rennes 1. His current research interests concentrate on homogeneous catalysis with particular emphasis on well-defined iron complexes in catalysis. 2474Scheme 12. Proposed mechanism for the selective formation of the secondary imines.Scheme 13. Selective reductive cross-coupling of nitriles and amines to form secondary aldimines. 2475Scheme 49. Iridium-iron-catalysed tandem conversion of alkanes to alkylsilanes. 2485 the use of CO 2 as a C1 building block, (ii) a step devoted to reduction of carboxylic derivatives, (iii) an enantioselective reduction step, and (iv) the use of biomass derivatives as starting materials.These achievements in iron-catalysed multi-step processes have already led to very impressive and promising results and will without any doubt stimulate their development in the near future.

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Highly Efficient Hydrogenation of Levulinic Acid into γ‐Valerolactone using an Iron Pincer Complex

Cited by 38 publications

References 63 publications

Solvent-free hydrogenation of levulinic acid to γ-valerolactone using a Shvo catalyst precursor: optimization, thermodynamic insights, and life cycle assessment

Solvent-free hydrogenation of levulinic acid to γ-valerolactone using a Shvo catalyst precursor: optimization, thermodynamic insights, and life cycle assessment

One‐pot conversion of carbohydrates into γ‐valerolactone under the coordination of heteropoly acid based ionic liquid and Ru/ZrO₂ in water media

Multi‐Step Reactions Involving Iron‐Catalysed Reduction and Hydrogen Borrowing Reactions

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Highly Efficient Hydrogenation of Levulinic Acid into γ‐Valerolactone using an Iron Pincer Complex

Cited by 38 publications

References 63 publications

Solvent-free hydrogenation of levulinic acid to γ-valerolactone using a Shvo catalyst precursor: optimization, thermodynamic insights, and life cycle assessment

Solvent-free hydrogenation of levulinic acid to γ-valerolactone using a Shvo catalyst precursor: optimization, thermodynamic insights, and life cycle assessment

One‐pot conversion of carbohydrates into γ‐valerolactone under the coordination of heteropoly acid based ionic liquid and Ru/ZrO2 in water media

Multi‐Step Reactions Involving Iron‐Catalysed Reduction and Hydrogen Borrowing Reactions

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One‐pot conversion of carbohydrates into γ‐valerolactone under the coordination of heteropoly acid based ionic liquid and Ru/ZrO₂ in water media