Production of a low‐cost scavenger resin to capture aldehydes and ketones in solutions

Abstract

Over the past years, polymer-supported reagents have been extensively studied and used in various applications. One class of such reagents is called "scavengers," which can be used to easily eliminate compounds in a solution. The present work describes the production of a resin that can be used for scavenging ketones and aldehydes using low-cost reagents and simple reaction steps, named here Amb15-Iso. This resin is obtained by reacting a low-cost commercial sulfonyl resin, Amberlyst-15, with isoniazid, a drug used for the treatment of tuberculosis. Acetone and isobutyraldehyde were used as carbonyl compound models. The reactions were monitored in-line by ATR-FTIR and results showed that the polarity of the solvent influences the kinetics of the production of the resin and water proved to be the fastest solvent. For the scavenging of acetone and isobutyraldehyde, two factors showed to have an impact in the amount of compounds captured: the polarity of the solvent and the solubility of water in the solvent. The capacity of scavenging acetone in water varied from 0.11 to 0.28 mmol per gram of resin, depending on the initial acetone concentration. The equilibrium of this reaction was modeled and the equilibrium constant was calculated to be 0.63 6 0.07 L mol 21 . The resin was also recycled and tested in a second round of scavenging and results showed that there was not much difference between the new resin and the recycled one, proving that the Amberlyst-15 could be reused for a second cycle of scavenging. V C 2015 Wiley Periodicals, Inc. J.Appl. Polym. Sci. 2015, 132, 42291.

Effects of Solvent Polarity on the Reaction of Aldehydes and Ketones with a Hydrazide-Bound Scavenger Resin

“…This behavior is in agreement with the results presented in an earlier paper. 15 However, if hexane is included in the discussion, the correlation with solvent polarity disappears, which may be explained by the water solubility of the different solvents. While water is miscible with ethanol and acetonitrile, it has a low solubility in dichloromethane and an even lower solubility in hexane.…”

“…The saturation that was achieved for the isoniazid in the resin was 2 mEq/g resin. 15 However, the capacity of the acidic sites in the commercial Amberlyst-15 is 4.7 mEq/g. The smaller saturation concentration of isoniazid with respect to the concentration of acidic sites in the resin indicates that there are still free acid sites left in the resin, as shown in Scheme 3.…”

“…15 For the batch system, 40 mL of the solvent (water) and 2 g of isoniazid were added to the reaction vessel. The system was maintained at a constant temperature of 40 °C, at a stirring speed of 150 rpm.…”

“…8−14 To investigate the possibility of a novel and low-cost resin for the scavenging of aldehyde and ketones, we previously investigated the synthesis of a resin, named Amb15-Iso, which was obtained from the reaction between a commercial acid resin (Amberlyst-15) and isoniazid (isonicotinic acid hydrazide, CAS: 54-85-3), a drug for tuberculosis treatment. 15 Amb15-Iso is a low-cost resin and has the ability to remove aldehydes and ketones from solutions in a single-step reaction. Acetone and isobutyraldehyde were used as models to study the capture of molecules by the resin.…”

Aldehydes as Wort Off-Flavours in Alcohol-Free Beers—Origin and Control

“…An effort of producing such a polyamides resin at low cost to capture aldehydes and ketones was made by de Oliveira et al (de Oliveira et al 2015). The authors synthesised the isoniazid-functionalized resin Amb15-iso by reacting commercially available Amberlyst 15 with isoniazid, which is an antibiotic commonly used in the treatment of tuberculosis.…”