Greener process to prepare and scale-up zwitterionic macro cyclic dihydroxy-aza-crown ether and their corresponding supramolecular pairs to enhanced oil recovery application

• Published in: Journal of cleaner production Vol. 420; p. 138446
• Main Authors: Cerón-Camacho, Ricardo, Cisneros-Dévora, Rodolfo, Soto-Castruita, Enrique, Ramírez-Pérez, Jorge F., Martínez-Magadán, José M., Oviedo-Roa, Raúl, Zamudio-Rivera, Luis S.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 25.09.2023
• Subjects: Enhanced oil recovery; Green metrics; Green scale-up; Macro cyclic dihydroxy-aza-crown ether; Supramolecular pair; Supramolecular pair; Green metrics; Macro cyclic dihydroxy-aza-crown ether; Green scale-up; Enhanced oil recovery
• ISSN: 0959-6526; 1879-1786
• DOI: 10.1016/j.jclepro.2023.138446

This manuscript discusses a green and clean route to prepare macro cyclic dihydroxy-aza-crown ether (MC-DACE) compounds, their zwitterionic derivatives, and the corresponding supramolecular pairs with a cationic surfactant. A conventional one vessel two-step process developed as the synthetic route. The first step consists of a reaction without solvent to obtain MC-DACE, and the next stage occurs in aqueous to get zwitterionic macro cyclic dihydroxy-aza-crown ether (ZWMC-DACE). We prepared the first instance in the lab scale, and a subsequent scale-up process was carried out. Green metrics were determined and performed through Andraos pentagon, showing that synthetic approaches are greener and environmentally friendly concerning other routes to prepare analog compounds. These ZWMC-DACE and corresponding supramolecular pairs with dodecyl trimethyl ammonium chloride (DTAC) have been tested with good performance in the enhanced oil recovery (EOR) application to study their wettability-altering and non-emulsion formation. •Green and clean process to prepare macro cyclic dihydroxy-aza-crown ether derivatives.•One-vessel two-steps process to get zwitterionic macro cyclic dihydroxy-aza-crown ether.•Supramolecular pairs derived from zwitterionic macro cyclic compounds.•Application in EOR of the zwitterionic macro cyclic dihydroxy-aza-crown ether and their supramolecular pairs.•Scale-up process in pilot plant through a clean process maintaining green metrics.