Efficient capturing of hydrogen peroxide in dilute aqueous solution by co-crystallization with amino acids

Abstract

Hydrogen peroxide (H2O2) in dilute aqueous solution can be efficiently captured by co-crystallisation with enantiomeric and racemic amino acids as evidenced by colourimetric titration and the single crystal X-ray structural...

Solid–Liquid Phase Equilibrium and Diagram of a l-Phenylalanine–Hydrogen Peroxide–Water Ternary System

“…It is well known that solid–liquid equilibrium data is of noteworthy scientific and practical importance in the crystallization operation process. As described in previous works, − l -phenylalanine reacts with hydrogen peroxide in solutions and l -phenylalanine perhydrate crystallizes from the solution system. Obviously, the basis of the preparation process of l -phenylalanine perhydrate is the ternary phase diagram of the l -phenylalanine–hydrogen peroxide–water system.…”

“…Hydrogen bonding of hydrogen peroxide and amino acids has attracted noteworthy scientific attention because of the significance of transport of hydrogen peroxide in cellular membranes − and the bio-oxidation process of hydrogen peroxide. , Since amino acids are insoluble in lots of organic solvents that can dissolve hydrogen peroxide, amino acid perhydrates are particularly appropriate materials for the preparation of solutions of anhydrous hydrogen peroxide. Until now, many amino acid perhydrates have been reported in previous works, for instance, serine perhydrate, − glycine perhydrate, dl -2-aminobutyric acid perhydrate, l -isoleucine perhydrate, l -phenylalanine perhydrate, − and cysteine perhydrate, . Synthesis of most of them needs higher concentrations of the hydrogen peroxide solution, for example, >70 wt %.…”

“…Synthesis of most of them needs higher concentrations of the hydrogen peroxide solution, for example, >70 wt %. However, pure crystalline l -phenylalanine perhydrate can be obtained from the commonly used 50 wt % hydrogen peroxide , and even a dilute aqueous solution of H 2 O 2 (30 wt %) . It is generally synthesized by introducing a certain amount of l -phenylalanine into an aqueous solution of H 2 O 2 to obtain saturated solutions.…”

“…Then, the prepared solutions are allowed to cool to generate colorless crystals of l -phenylalanine perhydrate. Yamaguchi and co-workers studied the single-crystal structures of this perhydrate . Nevertheless, to the best of the authors’ current knowledge, further investigations on this perhydrate have not yet been made in open publications.…”

Comparison of Proton Acceptor and Proton Donor Properties of H2O and H2O2 in Organic Crystals of Drug-like Compounds: Peroxosolvates vs. Crystallohydrates

“…The H 2 O 2 molecule forms one or two H-bonds as a proton acceptor in about half of the peroxosolvates [ 14 ]. A significant number of these crystals contain zwitterions [ 17 , 18 , 19 ]. The oxygen of the H 2 O 2 molecule and the + H 3 N- group of the amino acid zwitterion often form nonlinear H-bonds (the O∙∙∙H-N + angle is less than 140 degrees), Figure S1 .…”