Ruthenium-catalyzed hydrogenation of aromatic amino acids in aqueous solution

Sun, Bing; Süß‐Fink, Georg

doi:10.1016/j.jorganchem.2015.09.011

Cited by 11 publications

(4 citation statements)

References 35 publications

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“…However, racemization of amino alcohols and C−O hydrogenolysis to the corresponding amines were more pronounced under these conditions. Moreover, the aromatic moieties in phenylalanine and tyrosine were completely reduced to their saturated analogs, but this side reaction has been observed for Ru‐based catalysts as well . Poisoning of the Rh catalyst by cysteine and methionine was avoided by applying an oxidative pretreatment with performic acid, to convert the S‐containing thiol and thioether groups into inert sulfonic acid and sulfone groups, which do not possess lone pairs anymore …”

Section: Amino Acids As Direct Precursors To Value‐added Chemicalsmentioning

confidence: 99%

Protein‐Rich Biomass Waste as a Resource for Future Biorefineries: State of the Art, Challenges, and Opportunities

et al. 2019

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Protein‐rich biomass provides a valuable feedstock for the chemical industry. This Review describes every process step in the value chain from protein waste to chemicals. The first part deals with the physicochemical extraction of proteins from biomass, hydrolytic degradation to peptides and amino acids, and separation of amino acid mixtures. The second part provides an overview of physical and (bio)chemical technologies for the production of polymers, commodity chemicals, pharmaceuticals, and other fine chemicals. This can be achieved by incorporation of oligopeptides into polymers, or by modification and defunctionalization of amino acids, for example, their reduction to amino alcohols, decarboxylation to amines, (cyclic) amides and nitriles, deamination to (di)carboxylic acids, and synthesis of fine chemicals and ionic liquids. Bio‐ and chemocatalytic approaches are compared in terms of scope, efficiency, and sustainability.

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Section: Amino Acids As Direct Precursors To Value‐added Chemicalsmentioning

confidence: 99%

Protein‐Rich Biomass Waste as a Resource for Future Biorefineries: State of the Art, Challenges, and Opportunities

et al. 2019

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“…Nanoparticles with controllable chemical and physical properties can conveniently be obtained by employing suitable organometallic precursors [24]. We have previously shown that the selectivity during catalytic hydrogenation reactions can be conveniently controlled with nano ruthenium, which was obtained from arene ruthenium complexes devoid of interfering chloride ions [21,[25][26][27][28][29][30][31]. In this work, dicationic aqua complex [Me(C6H4)Pr i )Ru(H2O)3] 2+ was used as a precursor to avoid the presence of contaminants on the surface of nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium Nanoparticles Intercalated in Montmorillonite (nano-Ru@MMT) Is Highly Efficient Catalyst for the Selective Hydrogenation of 2-Furaldehyde in Benign Aqueous Medium

et al. 2021

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Chemoselective hydrogenation of 2-furaldehyde to furfuryl alcohol using green solvents is an important research area to get eco-friendly fuels and fine chemicals. Herein, we report ruthenium nanoparticles (~1.8 nm) intercalated in montmorillonite as an efficient catalytic system, which can selectively hydrogenate 2-furaldehyde in a benign aqueous medium. The complete conversion was observed at 40 °C with 1 MPa H2, the selectivity of furfuryl alcohol being >99%, and turnover number 1165. After a catalytic run, the montmorillonite-supported ruthenium nanoparticles can be recycled and reused without losing their activity and selectivity.

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“…glycine, alanine, valine, leucine, isoleucine, proline, serine, threonine, and lysine) or ester derivatives thereof have been modified successfully to the corresponding amino alcohols. ,,,,,,,,, The hydrogenation of other amino acids is more challenging due to the presence of multiple and potentially interfering functional groups in the side chain. For instance, the aromatic moieties in phenylalanine, tyrosine, and tryptophan are preferentially reduced compared to the carboxylic acid, and glutamic acid is converted readily to pyroglutamic acid under typical reaction conditions. , Moreover, the hydrogenation of mixtures is currently limited to synthetic mixtures of three amino acids with an aliphatic side chain …”

Section: Introductionmentioning

confidence: 99%

Rh-Catalyzed Hydrogenation of Amino Acids to Biobased Amino Alcohols: Tackling Challenging Substrates and Application to Protein Hydrolysates

Vandekerkhove

Claes

Schouwer

et al. 2018

ACS Sustainable Chem. Eng.

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While protein-rich biomass waste is nowadays mainly used for animal feed, conversion of its amino acid constituents to nitrogenous chemicals is a potential higher value route. To that end, the hydrogenation of amino acids to amino alcohols was studied in this work. Using a bimetallic Rh-MoOx/SiO2 catalyst, glutamic acid was for the first time hydrogenated to the aminodiol in high yield. By minimizing partial reduction and consecutive hydrogenolysis, and by suppressing the competitive cyclization to pyroglutamic acid (and derivatives thereof), glutamidiol was obtained in 77% yield at 70 bar H2 and 80 °C. High yields (typically > 80%) and selectivities were also achieved for most other natural amino acids, except for the S-containing amino acids 2 cysteine and methionine, which act as catalyst poisons. This limitation was overcome by applying a simple oxidation step with performic acid prior to the hydrogenation. The system was applied successfully to a mixture of amino acids obtained by hydrolysis of pre-oxidized bovine serum albumin. Amino alcohols were produced with high overall conversion (> 90%) and selectivity (88%) without the need for an intermediate, expensive and difficult separation step. The reaction proceeds with very high atom economies for both carbon and nitrogen, and generates only water as a by-product.

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Ruthenium-catalyzed hydrogenation of aromatic amino acids in aqueous solution

Cited by 11 publications

References 35 publications

Protein‐Rich Biomass Waste as a Resource for Future Biorefineries: State of the Art, Challenges, and Opportunities

Protein‐Rich Biomass Waste as a Resource for Future Biorefineries: State of the Art, Challenges, and Opportunities

Ruthenium Nanoparticles Intercalated in Montmorillonite (nano-Ru@MMT) Is Highly Efficient Catalyst for the Selective Hydrogenation of 2-Furaldehyde in Benign Aqueous Medium

Rh-Catalyzed Hydrogenation of Amino Acids to Biobased Amino Alcohols: Tackling Challenging Substrates and Application to Protein Hydrolysates

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