Synthesis, Characterization, and Evaluation of Solution Properties of Sesame Fatty Methyl Ester Sulfonate Surfactant

Abstract

The search for alternative, biodegradable, and sustainable raw materials to replace finite petrochemicals is an area of great interest. Triglycerides obtained from oilseed crops are such potential raw materials. In this study, sesame oil was trans-esterified to sesame fatty methyl esters (SEFAMEs) that were used as precursors in the synthesis of sesame fatty methyl esters sulfonate (SEFAMESO) surfactant. SEFAME and SEFAMESO surfactants were characterized by high-performance liquid chromatography–mass spectrometry (HPLC-MS), 1H NMR, and Fourier transform infrared (FTIR) spectra. HPLC-MS, 1H NMR, and FTIR spectra indicated successful trans-esterification and conversion of SEFAMEs to SEFAMESO. Solution properties of the SEFAMESO surfactant including hydrophilic–lipophilic balance (HLB) value, Krafft point, foam-ability, critical micelle concentration (CMC), counterion degree of binding and thermodynamic parameters such as ΔG°mic, ΔH°mic, ΔS°mic, ΔH°mic,* and T C were evaluated. The CMC values of SEFAMESO at 298.15 K were relatively lower than that of the sodium dodecyl sulfate (SDS) standard, and these values decreased to a minimum at 303.15 K and then increased with an increase in temperature. ΔG°mic values were negative indicating a spontaneous micellization process. ΔH°mic and ΔS°mic values revealed that micellization was entropy-driven at low temperatures and both entropy- and enthalpy-driven at high temperatures. ΔH°mic,* values were negative suggesting formation of stable micelles. The evaluated properties revealed the potential application of the synthesized surfactant as a cleansing agent.

Artificial Intelligence Techniques and Response Surface Methodology for the Optimization of Methyl Ester Sulfonate Synthesis from Used Cooking Oil by Sulfonation

“…Figure presents the FTIR analysis conducted on both ME and MES to determine the functional groups. The FTIR spectra of ME and MES revealed some peaks around 2939–2911 cm –1 , indicating −CH 3 (methyl) stretching vibration. , Also, the peak at 1745 cm –1 (CO stretching) appeared in the spectra of both samples, suggesting that the sulfonation process did not affect the ester group, as reported for ME and MES obtained from sesame oil . The new peaks at 1351, 1168, and 1089 cm –1 on the spectrum of the UCO MES were all attributed to SO vibration reductions, indicating that sulfonic acid (−SO 3 H) was successfully incorporated into the MES structure in the form of C-SO 3 H .…”

“…The 1 H NMR results of the ME and MES samples are shown in Figure . The signals at around 0.88–0.97 ppm in the ME spectrum were attributed to the methyl (CH 3 −) proton of the fatty acid chains, whereas the signals at around 1.41–2.10 ppm were attributed to the methylene (−CH 2 −) protons of saturated acyl chains . Peaks at 3.71 and 5.42 ppm, respectively, indicated the presence of protons of CH 3 –O– in ester and −CHCH of the vinyl group .…”

“…4,13 Also, the peak at 1745 cm −1 (C�O stretching) appeared in the spectra of both samples, suggesting that the sulfonation process did not affect the ester group, as reported for ME and MES obtained from sesame oil. 1 The new peaks at 1351, 1168, and 1089 cm −1 on the spectrum of the UCO MES were all attributed to S�O vibration reductions, indicating that sulfonic acid (−SO 3 H) was successfully incorporated into the MES structure in the form of C-SO 3 H. 4 These FTIR data confirmed that the sulfonation product was methyl ester sulfonate. 47 However, after the conversion of ME to MES via the sulfonation process, some signal disappeared while some new 15 displays the plot of surface tension against MES concentration.…”

“…5,6 As a result, there is a need to develop an innovative technology for collecting UCO from various locations and using it as a feedstock in the commercial production of fatty acid methyl ester (FAME) for surfactant (methyl ester sulfonate, MES) synthesis. 1,7 Surfactants are derived from either petrochemicals or oleochemicals. 1 Surfactants derived from bio-oils have been found to be nontoxic, less viscous, biodegradable, soluble in water, and slightly irritant to humans 4,8 when compared to petroleum-based surfactants such as cetyltrimethylammonium-bromide (CTAB), internal olefin sulfonate (IOS), and sodium dodecyl sulfate (SDS), which may soon be phased out owing to the depletion of crude oil reserves.…”

Review of the Application of Natural Surfactants in Enhanced Oil Recovery: State-of-the-Art and Perspectives

“…The preferable feature of this method is a relatively high yield percentage to the initial reaction feedstock, which is the herbal oil in this method. Based on the 2022 report by Soy et al, the final produced anionic surfactant yield from sesame oil was 89.5% . According to Hutchinson et al, the most common steps after oil extraction are tarn esterification and a sulphonating process; the two-step preparation of natural surfactant from natural oil is shown in Figure…”