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A Simplified Method of Synthesis to Obtain Zwitterionic Cellulose under Mild Conditions with Active Ionic Moieties.

ABSTRACT: A simplified procedure to synthesize zwitterionic cellulose by means of N-protected aspartic anhydride under mild conditions was developed. The preparation of modified cellulose samples was carried out under heterogeneous, aqueous conditions by reacting NH4OH-activated cellulose with aspartic anhydrides N-protected with trifluoroacetyl (TFAc) and carbobenzyloxy (Cbz). Modified cellulose samples Cel-Asp-N-TFAc and Cel-Asp-N-Cbz were characterized by Fourier Transform Infrared (FTIR) and 13C solid state Nuclear Magnetic Resonance (NMR) spectroscopy. The functionalization degree of each cellulose sample was determined by the 13C NMR signal integration values corresponding to the cellulose C1 vs. the C? of the aspartate residue and corroborated by elemental analysis. In agreement, both analytical methods averaged a grafting degree of 20% for Cel-Asp-N-TFAc and 16% for Cel-Asp-N-Cbz. Conveniently, Cel-Asp-N-TFAc was concomitantly partially N-deprotected (65%) as determined by the ninhydrin method. The zwitterion character of this sample was confirmed by a potentiometric titration curve and the availability of these amino acid residues on the cellulose was inspected by adsorption kinetics method with a 100 mg L-1 cotton blue dye solution. In addition, the synthesis reported in the present work involves environmentally related advantages over previous methodologies developed in our group concerning to zwitterionic cellulose preparation.

SUBMITTER: Haro-Mares NB

PROVIDER: S-EPMC7412472 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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A Simplified Method of Synthesis to Obtain Zwitterionic Cellulose under Mild Conditions with Active Ionic Moieties.

Haro-Mares Nadia B NB Meza-Contreras Juan C JC López-Dellamary Toral Fernando A FA González-Cruz Ricardo R Silva-Guzmán José A JA Manríquez-González Ricardo R

Molecules (Basel, Switzerland) 20200705 13

A simplified procedure to synthesize zwitterionic cellulose by means of N-protected aspartic anhydride under mild conditions was developed. The preparation of modified cellulose samples was carried out under heterogeneous, aqueous conditions by reacting NH<sub>4</sub>OH-activated cellulose with aspartic anhydrides N-protected with trifluoroacetyl (TFAc) and carbobenzyloxy (Cbz). Modified cellulose samples Cel-Asp-N-TFAc and Cel-Asp-N-Cbz were characterized by Fourier Transform Infrared (FTIR) an ...[more]

PMID: 32635597

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Project description:A new class of surface active ionic liquids (SAIL) have been reported to be a greener alternative to the conventional surfactants in enhanced oil recovery (EOR). These SAILs work efficiently under harsh salinity conditions encountered in the reservoir thereby recovering more additional oil during the tertiary oil recovery process. Adsorption mechanism of SAILs on different rock surface is however, not yet reported in the literature. This article highlights adsorption mechanism of three cationic SAILs having different headgroups, viz., imidazolium, pyridinium, pyrrolidinium, on different rock surfaces (crushed natural carbonate rock and crushed sandstone rock). All the SAILs studied here however had the same tail length and same anion (Br-) attached to it. XRD and XPS characterization techniques reveal that the crushed natural carbonate rock contains a substantial amount of silica, thus rendering it a slight negative charge. Static adsorption tests show that the retention efficiency on the natural carbonate type of rock for all the SAILs was lower than the conventional cationic surfactant, CTAB. The adsorption data obtained thereby was examined using four different adsorption isotherm models (Langmuir, Freundlich, Redlich-Peterson, and Sips). Results suggest that Sips adsorption isotherm model can satisfactorily estimate the adsorption of all the surface active agents on the natural carbonate rock. Factors like mineralogical composition of rock surface, presence of divalents, temperature, and structure of surfactants strongly affect the amount of surfactant adsorbed on reservoir rock. In order to evaluate the simultaneous effect all these factors as well as their interdependence on the retention capability of the three SAILs, a design of experiments approach has been employed further in this study. Statistical analysis of the data obtained after performing the full factorial experiments reveal that at high salinity, imidazoluim based SAIL show minimal adsorption on crushed natural carbonate rock at higher temperature. In general, at a given ionic strength, with increasing temperature as the amount of divalent in the aqueous solution increases, the amount of SAIL adsorbed on both the rock types decreases. Electrostatic attraction is the basic mechanism in governing adsorption of SAILs on the two types of rock surfaces. Results presented in this work can be used for EOR schemes.

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A Simplified Method of Synthesis to Obtain Zwitterionic Cellulose under Mild Conditions with Active Ionic Moieties.

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A Simplified Method of Synthesis to Obtain Zwitterionic Cellulose under Mild Conditions with Active Ionic Moieties.

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