A Process for the Production of Φ-Sulfo Fatty Methyl Ester Sulfonates (Φ-MES)

Abstract

AbstractΦ-Sulfo Fatty Methyl Esters sulfonates (Φ-MES) were obtained via sulfoxidation of fatty acid methyl esters (FAME) with SO2, O2, and ultraviolet light of appropriate wavelength. Expectedly, these products may be used as linear alkylbenzene sulfonate (LAS) and alkyl ether sulfate (AES) partners, either in heavy-duty or in hand dishwashing liquids. Φ-MES are new anionic surfactants that can be regarded as potential components for detergent formulations and body care products as well. In this work we summarize the most relevant results of our research started fifteen years ago, on the synthesis, separation and analysis of Φ-sulfo fatty methyl ester sulfonates known as Φ-MES, and we update our last findings. We have to point out that we are for the time being, the only research group in the world to have published our research on Φ-MES. This paper describes the optimum batch conditions for the sulfoxidation of FAME and a reaction mechanism is proposed. The paper depicts an improved workup for the separation of reaction products from non reacted methyl ester and the GC-MS analysis of Φ-sulfo fatty methyl ester sulfonate is shown. Finally, an interpretation of conversion and selectivity of sulfoxydation reaction is given.

Sulfonated methyl esters of fatty acids in aqueous solutions: Interfacial and micellar properties

“…The production of SME has been growing during the last ten years and currently it stands at more than ten percent of the LAS production. In general, sodium methyl ester sulfonates with random positioning of the SO 3 group in the alkyl chain, known as U-MES, have been synthesized [6][7][8][9][10][11]. Our study is focused on the a-sulfo fatty acid methyl esters (Fig.…”

Study of Synthesis Polyethylene glycol oleate Sulfonated as an Anionic Surfactant for Enhanced Oil Recovery (EOR)

“…This reaction has been performed by using Li [17], for PEG Dioleate (PDO), the sulfonation process was carried out using 50% of total weight H 2 O 2 reactants. Furthermore, the sample is washed using 50% methanol to convert all remaining fatty acids [18]. The following sulfonation process: (1) amount of sulfuric acid as a sulfonation agent, was added with varying mole ratio of 1:0,5; 1:1; and 1:1,5.…”

“…While the mole ratio of 1:0,5, sulfuric acid as sulfonation agent used is not optimal, so iodine value is still high. The highest number of iodine on TM (without methanol) indicates that there are still many reactants that do not react [6,8,18]. In Figure 2, ester value is an indicator of the ester compound.…”

“…On the other hand, the ester value increased with sulfonation reactions. Increasing ester value occurred because of extension chain of reactive carboxyl from PDO [17], it will react with the base which means the residual acid in the anionic surfactant product is reduced [6,8,18]. Babu in his study made sodium methyl ester sulfonate from ricinoleic acid, with the result of acid value, saponification value and iodine value are 10-12, 185-190, and 80-90 respectively.…”

Influence of process conditions on the sulfonation of methyl ester synthesized from used cooking oil: Optimization by Taguchi approach

“…MES is an oleochemical‐based surfactant with molecules consisting of carbon chains (hydrophobic) and a sulfonic functional group (hydrophilic) (Jin et al, 2016). Because of its low oil/H 2 O interfacial tension and environmental friendliness, MES, unlike common petroleum‐derived surfactants, could be used directly as a phosphide‐free detergent (Cohen et al, 2010; Kang et al, 2013). Aside from that, MES is water soluble (Jin et al, 2016), nontoxic and low viscous (Cohen et al, 2008), biodegradable (Afida et al, 2016), has a low irritant to humans and has better wetting power (Stirton, 1962), and is more resistant to different water hardness than petroleum‐based surfactants (Maurad et al, 2020).…”