Reductive Amination of 1-Hydroxy-2-propanone Over Nickel and Copper Catalysts

Trégner, T.

doi:10.15255/cabeq.2017.1077

Cited by 7 publications

(4 citation statements)

References 37 publications

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“…The reductive amination of 1-hydroxy-2-propanone (acetol) with anhydrous, gaseous NH 3 to 2-aminopropanol in the gas phase over a commercial Ni catalyst (KL6527-CY; KataLeuna) was presented by Trejbal and co-workers in 2017 (Scheme 46B). 90 The catalyst material was reduced in a fixed-bed reactor (in situ) at 230 °C in a nitrogen−hydrogen atmosphere with gradually increased hydrogen concentration and, finally, kept at 260 °C in a hydrogen stream for an additional 18 h. The selectivity to 2-aminopropanol achieved with this catalyst was about 45% at most. The optimal molar ratio of H 2 /acetol was 25, and the optimal molar ratio of H 2 /NH 3 was 1.…”

Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

“…203 The Au >99 Ag In 2017, Trejbal and co-workers reported the reductive amination of 1-hydroxy-2-propanone (acetol) with NH 3 to form 2-aminopropanol in a fixed-bed reactor at 220 °C. 90 The commercial Adkins (Cu/Cr) catalyst (T-4466; Sud-Chemie) was used as a tablet with a size of 3 × 3 mm (53% CuO and 45% Cr 2 O 3 ). The tablets were first reduced in the fixed-bed reactor at 230 °C in a nitrogen−hydrogen atmosphere with gradually increased hydrogen concentration.…”

Section: Multimetal Catalysts On Reductive Aminationmentioning

confidence: 99%

“…In 2017, Trejbal and co-workers reported the reductive amination of 1-hydroxy-2-propanone (acetol) with NH 3 to form 2-aminopropanol in a fixed-bed reactor at 220 °C . The commercial Adkins (Cu/Cr) catalyst (T-4466; Süd-Chemie) was used as a tablet with a size of 3 × 3 mm (53% CuO and 45% Cr 2 O 3 ).…”

Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

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Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

2020

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The reductive amination, the reaction of an aldehyde or a ketone with ammonia or an amine in the presence of a reducing agent and often a catalyst, is an important amine synthesis and has been intensively investigated in academia and industry for a century. Besides aldehydes, ketones, or amines, starting materials have been used that can be converted into an aldehyde or ketone (for instance, carboxylic acids or organic carbonate or nitriles) or into an amine (for instance, a nitro compound) in the presence of the same reducing agent and catalyst. Mechanistically, the reaction starts with a condensation step during which the carbonyl compound reacts with ammonia or an amine, forming the corresponding imine followed by the reduction of the imine to the alkyl amine product. Many of these reduction steps require the presence of a catalyst to activate the reducing agent. The reductive amination is impressive with regard to the product scope since primary, secondary, and tertiary alkyl amines are accessible and hydrogen is the most attractive reducing agent, especially if large-scale product formation is an issue, since hydrogen is inexpensive and abundantly available. Alkyl amines are intensively produced and use fine and bulk chemicals. They are key functional groups in many pharmaceuticals, agro chemicals, or materials. In this review, we summarize the work published on reductive amination employing hydrogen as the reducing agent. No comprehensive review focusing on this subject has been published since 1948, albeit many interesting summaries dealing with one or the other aspect of reductive amination have appeared. Impressive progress in using catalysts based on earth-abundant metals, especially nanostructured heterogeneous catalysts, has been made during the early development of the field and in recent years.

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Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

Section: Multimetal Catalysts On Reductive Aminationmentioning

confidence: 99%

Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

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Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

2020

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“…They followed a unique approach by first performing an acid-catalyzed hydrolysis of cellulose and retro-aldol of glucose into GA, followed by the reductive amination of GA with NH 3 in water. 27,34 Control of selectivity is the major concern in the reductive amination of aldehydes and ketones, and it is particularly challenging with α-hydroxy substrates such as GA. 35,36 Carbonyls are intrinsically susceptible for nucleophilic addition (e.g., with alcohols or water) and for aldol reactions. In reductive amination circumstances, the reactive carbonyl group can also reduce to the alcohol, causing depletion of substrate.…”

Section: ■ Introductionmentioning

confidence: 99%

Glycolaldehyde as a Bio-Based C₂ Platform Chemical: Catalytic Reductive Amination of Vicinal Hydroxyl Aldehydes

et al. 2019

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Reductive amination of glycolaldehyde (GA), the smallest sugar molecule and obtainable from biomass, creates a versatile platform for ethylamine products, potentially replacing current pathways via toxic ethylene oxide and dichloroethane. Given the high reactivity of α-OH carbonyls, the main challenge was control of selectivity in a cascade of parallel and consecutive reactions during reductive amination. The type of solvent and catalyst, preferably methanol and Pd, respectively, are key enabling parameters to achieve high product yields. A kinetic study on product intermediates accompanied with detailed product analysis (MS and NMR) suggested a general mechanistic scheme and validation with density functional theory calculations provided a rational understanding of the solvent effect in terms of energetics and kinetics. Primary alkanolamines (AA) such as 2-(dimethylamino)-ethanol are preferred products, and large excess of the amine reagent is not required to reach almost quantitative yields. Interestingly substoichiometric amine-to-GA ratio allows for high yield of higher (consecutive) AAs such as N-methyldiethanolamine (MDEA) and triethanolamine, for which a peculiar cyclic 5-membered oxazolidinic precursor was analyzed (e.g., for reaction with monomethylamine to MDEA). The shift to diamine-selective (DA) reactions is possible by switching to a two-step one-pot approach. With ethylene glycol as a preferred solvent, high yield of an unsaturated C 2 -enediamine precursor is obtained under an inert atmosphere, followed by its metal-catalyzed hydrogenation at elevated temperature to the final DA product such as N,N,N′,N′-tetramethylethylene-diamine. A conceptual model of the catalytic reductive amination routes that allows production of a variety of ethylamines with up to +90 C % yield is thus presented. The successful preparation and sensory assessment of a GA-based diester quat in fabric softener formulations demonstrates the viability of a full bio-based and drop-in production route for high-value chemicals, directly from GA as a platform molecule.

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Earth‐abundant Metal‐catalyzed Reductive Amination: Recent Advances and Prospect for Future Catalysis

Liu

Song

2021

Chemistry An Asian Journal

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Nitrogen‐containing compounds, as an important class of chemicals, have been used widely in pharmaceuticals, materials synthesis. Transition metal‐catalyzed reductive amination of an aldehyde or a ketone with ammonia or an amine has been proved to be an efficient and practical method for the preparation of nitrogen‐containing compounds in academia and industry for a century. Given the above, several effective methods using transition metals have been developed in recent years. Noble transition metals like Pd, Pt, and Au‐based catalysts have been predominately used in reductive amination. Because of their high prices, strict official regulations of residues in pharmaceuticals, and deleterious effects on the biological system, their industrial applications are severely hampered. With the increasing sustainable and environmental problems, the Earth‐abundant transition metals including Ti, Fe, Co, Ni, and Zr have also been investigated for the reductive amination reaction and showed great potential to the advancement of sustainable and cost‐effective reductive amination processes. This critical review will mainly summarize the work using Earth‐abundant metals. The effects of different transition metals used in catalytic reduction amination were discussed and compared, and some suggestions were given. The last section highlights the catalytic activities of bi‐ and tri‐metallic catalysts. Indeed, this latter family is very promising and simultaneously benefits from increased stability, and selectivity, compared to monometallic NPs, due to synergistic substrate activation. Few comprehensive reviews focusing on Earth‐abundant transition metals catalyst has been published since 1948, although several authors reported some summaries dealing with one or the other part of this aspect. It is hoped that this critical review will inspire researchers to develop new efficient and selective earth‐abundant metal catalysts for highly, environmentally sustainable reductive amination methods, as well as improve the pharmaceutical industry and related chemical synthesis company traditional method with the utilization of the green method widely.

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Reductive Amination of 1-Hydroxy-2-propanone Over Nickel and Copper Catalysts

Cited by 7 publications

References 37 publications

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Glycolaldehyde as a Bio-Based C₂ Platform Chemical: Catalytic Reductive Amination of Vicinal Hydroxyl Aldehydes

Earth‐abundant Metal‐catalyzed Reductive Amination: Recent Advances and Prospect for Future Catalysis

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Reductive Amination of 1-Hydroxy-2-propanone Over Nickel and Copper Catalysts

Cited by 7 publications

References 37 publications

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Glycolaldehyde as a Bio-Based C2 Platform Chemical: Catalytic Reductive Amination of Vicinal Hydroxyl Aldehydes

Earth‐abundant Metal‐catalyzed Reductive Amination: Recent Advances and Prospect for Future Catalysis

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Glycolaldehyde as a Bio-Based C₂ Platform Chemical: Catalytic Reductive Amination of Vicinal Hydroxyl Aldehydes