The Application of Quantitative Structure–Property Relationship Modeling and Exploratory Analysis to Screen Catalysts for the Synthesis of Oleochemical Carbonates from CO₂ and Bio‐Based Epoxides

Abstract

Screening catalysts for the synthesis of cyclic carbonates from CO 2 and epoxides presents a challenge for the research community. Thus, we propose the application of quantitative structure-property relationships (QSPR) modeling and exploratory analysis to assist in the selection of catalysts to produce oleochemical carbonates. QSPR modeling was developed by applying 2D-descriptors to evaluate the relationship between the molecular structure of organocatalysts and their activity in the production of biobased organic carbonates. From the virtual screening, 122 potential catalysts were selected, their catalytic activities were estimated, and the best molecular targets highlighted. Already from the data mining and exploratory analysis, the catalysts' key structural features (e.g. organic structure, molecular arrangement, carbon chain size, and substituent type) were identified. Thus, it was possible to evaluate the similarity between the catalysts and to relate the 2D-descriptors to their activity. Then, based on QSPR modeling results, cetyltrimethylammonium bromide (CTAB) was proposed as a new catalyst to produce oleochemical carbonates. From the CTAB application, conversions greater than 98% of epoxide were observed in the cycloaddition of CO 2 to epoxidized vegetable oil (rice bran, canola, and soybean). Thus, it was concluded that QSPR modeling and exploratory analysis show potential for screening catalysts for oleochemical carbonate synthesis.

Catalytic Systems for the Effective Fixation of CO2 into Epoxidized Vegetable Oils and Derivates to Obtain Biobased Cyclic Carbonates as Precursors for Greener Polymers

“…dos Santos et al. carried out a selection of the most suitable ionic liquids to be employed as catalysts in the synthesis of oleochemical carbonates by quantitative structure–property relationship (QSPR) modeling and exploratory analysis . This theoretical approach allowed the authors the selection of 122 potential available catalysts for the target reaction.…”

Epoxidation of Vegetable Oils via the Prilezhaev Reaction Method: A Review of the Transition from Batch to Continuous Processes

“…The oxirane ring shows a high reactivity, indeed. Thus, epoxidized vegetable oils (EVOs) can be used as starting materials to produce alcohols, , diols, − carbonylic compounds, − hydroxyesters, , N -hydroxy­alkylamides , and polymers such as polyols, polyesters and polyurethanes. ,− Furthermore, EVOs find direct applications as plasticizers and stabilizers for poly­(vinyl chloride) (PVC) resins − and in biodegradable packaging materials, , reactive diluents for painting, and low- and high-temperature lubricant bases. − The use of EVOs as plasticizers is definitely the main reason why these compounds have attracted interest, as they can replace phthalates, a class of compounds which have been restricted in the European Union since July 2020 in textiles that are in contact with the skin, including clothes, and in a large number of products such as children’s accessories, flooring, coated fabrics and paper, mattresses and footwear. , Limitations of phthalates in plastic products are regulated worldwide following different criteria and rules . The use of EVOs as plasticizers in PVC has been widely studied, proving the enhancement in terms of thermal and mechanical properties of the final material, as well as replacing toxic compounds, namely phthalates, with respect to conventional ones. ,,,,− However, the properties and compatibility as plasticizers are mainly affected by the nature of the EVOs. ,, The compatibility between the epoxidized oil and the macromolecules of the polymer is affected by the quality of the EVO.…”