Theoretical and experimental studies on the separation of cinnamyl acetate and cinnamaldehyde by adsorption onto a β-cyclodextrin polyurethane polymer

Abstract

In order to isolate cinnamyl acetate (CAc) and cinnamaldehyde (CA), which coexist in cinnamon oil, a crosslinked polymer of b-cyclodextrin polyurethane (CDPU) was synthesized via a facile route and investigated as a selective adsorbent. The successful crosslinking was confirmed by FTIR, TG-DSC, XRD, SEM and N 2 adsorption-desorption analysis. The adsorption mechanism was investigated through a series of instrumental analyses and theoretical calculations, indicating that the combination of noncovalent interactions (e.g., hydrogen bonding, hydrophobic interactions) accounts for the superior affinity of CAc to CDPU, compared with CA. The adsorption behaviors of CAc and CA on CDPU were performed in the static adsorption mode, in which CDPU exhibited a selective adsorption property to CAc. The adsorption kinetics and isotherms in a single component system agreed well with the pseudosecond-order kinetic model and Freundlich isotherm model, respectively. It is noteworthy that the equilibrium adsorption amount was enhanced in the presence of the co-solute, presumably resulting from the cooperative effect arising from Lewis acid-base and p-p stacking interactions between the adsorbed CAc and CA molecules. Due to the stronger adsorption affinity of CAc to CDPU, adsorption enhancement of CAc in the presence of CA is greater than that of CA in the presence of CAc, resulting in higher CAc/CA selectivity with increasing concentrations of the equimolar mixture of CAc and CA.Additionally, CDPU could be easily regenerated and maintained high adsorption capacities and separation efficiency even after six adsorption/desorption cycles.

Synthesis, Characterization and Antibacterial Activity of Novel β-Cyclodextrin Polyurethane Materials

“…3.1. Characterization of QAS-β-CDPU cm -1 and 1550cm -1 are attributed to stretching vibration of C=O and amide group [22].…”

“…The peak at 1155 cm -1 and 1440 cm -1 are severally corresponded to the stretching vibration of C-C/C-O and methylene. The peak at 1660 cm -1 and 1550cm -1 are attributed to stretching vibration of C=O and amide group [22].…”

Dual Spinneret Electrospun Polyurethane/PVA-Gelatin Nanofibrous Scaffolds Containing Cinnamon Essential Oil and Nanoceria for Chronic Diabetic Wound Healing: Preparation, Physicochemical Characterization and In-Vitro Evaluation

“…It displayed a broad-spectrum antimicrobial effect against molds, yeast, and bacteria through its major active constituent, cinnamaldehyde [ 30 ]. Natural CEO is used in a wide variety of fields in spices, food medicine, cosmetic products, and agricultural chemicals due to the presence of chemical constituents, including cinnamaldehyde (70–88%), o -methoxycinnamaldehyde (4–12%), cinnamyl acetate (CAc, 0.5–10%), and benzaldehyde (0.5–1%) [ 31 , 32 ]. Two challenges stand against bringing CEO, or essential oils (EOs) in general, to biological applications or clinical trials.…”

Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β‐cyclodextrin

“…Considering these merits, we have used the selective inclusion method for the isolation of several organic compounds with an aqueous solution of β‐CD . In a previous study, we reported that a β‐CD polyurethane polymer exhibited good adsorption selectivity for CAc over CA, thanks to the recognition ability of the β‐CD cavity …”

“…27,28 In a previous study, we reported that a b-CD polyurethane polymer exhibited good adsorption selectivity for CAc over CA, thanks to the recognition ability of the b-CD cavity. 29 In this study, b-CD was used for inclusion separation of CAc and CA. Firstly, the feasibility of the method was investigated in terms of the configuration and thermodynamic constants of inclusion complexes.…”