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Some Catalytic Problems in Reductive Amination of Aldehydes and Ketones
Published in Mike G. Scaros, Michael L. Prunier, Catalysis of Organic Reactions, 2017
The reaction of ammonia or primary or secondary amines with aldehydes or ketones in the presence of hydrogen and a hydrogenation catalyst to produce new amines is generally referred to as ‘reductive alkylation’ of the ammonia or amine or ‘reductive amination’ of the aldehydes or ketones. () R1R2NH+R3R4C=O+H2→R1R2(R3R4CH2)N+H2O
Catalytic Chemical Syntheses at High Pressure
Published in Ian L. Spain, Jac Paauwe, High Pressure Technology, 2017
Reductive amination is a process by which aldehydes and ketones react with ammonia in the presence of hydrogen and a catalyst to yield primary amines. Raney nickel has been widely used in reactions of different type ketones with excess ammonia under both moderate hydrogenation conditions and at elevated temperature and pressure. In the aliphatic series 2- and 3-aminoalkanes were prepared by amination of the corresponding ketones at 50 – 60°C and 90 – 100°C and 6 atm (~0.6 MPa); 2-aminoheptane was obtained from 2-heptanone at 90°C and 440 600 psi (3.03 – 4.14 MPa).
Catalytic Amination of Alcohols and Its Potential for the Synthesis of Amines
Published in John R. Kosak, Thomas A. Johnson, Catalysis of Organic Reactions, 2020
The most important process parameters to be optimized for selective catalytic amination are catalyst, temperature, molar ratio of reactants, hydrogen partial pressure, and the choice of the reactor. Since the choice of the catalyst will greatly influence all of the other parameters, we shall only consider here the amination over supported copper catalysts.
Putting the squeeze on imine synthesis: citrus juice as a reaction medium in the introductory organic laboratory
Published in Green Chemistry Letters and Reviews, 2023
Manisha Nigam, Dylan Tuttle, Barbora Morra, Andrew P. Dicks, Jose Rodriguez
After completing this reaction sequence, successful students will be able to: Complete a two-step reductive amination involving an acid-catalyzed imine synthesis in a citrus juice solvent.Perform a variety of fundamental laboratory techniques including heating under reflux, vacuum filtration, and crude product recrystallization.Characterize the imine and amine products by both proton nuclear magnetic resonance (1H NMR) spectroscopy and melting point determination.Identify the principles of green chemistry highlighted in the experiment and describe how each are used to help make chemical work safer and more responsible.Describe the reaction mechanism for the imine synthesis, including the effect of media acidity.
A review of immobilization techniques to improve the stability and bioactivity of lysozyme
Published in Green Chemistry Letters and Reviews, 2021
Paul T. Anastas, Alina Rodriguez, Tamara M. de Winter, Philip Coish, Julie B. Zimmerman
Muszanska et al. (119) constructed polymer-protein conjugates that were adsorbed onto gold-coated quartz surfaces to create functional coatings for biological systems, such as biomaterials implant surfaces. The polymer-protein conjugates consisted of lysozyme as the protein and a synthetic co-polymer made from one unit of polypropylene oxide (PPO) and two units of polyethylene oxide (PEO). The lysozyme was attached to the co-polymer via reductive amination of the aldehyde functionalized PEO blocks and the amine groups of lysine residues of the lysozyme. Testing the antibacterial activity of the lysozyme-PEO system against B. subtilis showed that it had a slightly lower antibacterial activity than that of free lysozyme. Some activity loss for lysozyme-PEO was possibly due to conformational changes of lysozyme as a result of the covalent coupling.
Amino acids: Building blocks for the synthesis of greener amphiphiles
Published in Journal of Dispersion Science and Technology, 2018
Nausheen Joondan, Sabina Jhaumeer Laulloo, Prakashanand Caumul
Damen et al.[54] reported the synthesis of the serine-proline-lysine-arginine Gemini surfactants 46 using solid phase techniques. The synthesis of 46 was initiated by the reductive amination of aldehyde resin followed by coupling with Fmoc-Arg(Pmc)-OH giving rise to oleyl amine. The amino acids Fmoc-Lys(Boc)-OH, Fmoc-Pro-OH and Fmoc-Ser(tBu)-OH were coupled to the resin after deprotection of the Fmoc group using 20% piperidine. The oleic acid was then coupled to the arginine and serine moieties of the peptide. Cleavage of the peptide from the resin followed by deprotection of the side chains gave the desired surfactant 46.