Synthesis, Characterization and Exploratory Application of Anionic Surfactant Fatty Acid Methyl Ester Sulfonate from Waste Cooking Oil

Abstract

The environmentally friendly anionic surfactant fatty acid methyl ester sulfonate (MES) was prepared by esterification of waste cooking oil (WCO), a low-cost raw material, followed by sulfonation with chlorosulfonic acid. MES production from WCO (W-MES) gave yields up to 78 %. Such a value is only slightly lower than the one obtained from soybean oil (S-MES), 82 %, and almost the same as that from reused cooking oil (R-MES), 76 %. According to the two-phase titration results, the content of the active component, a-MES, in S-MES, R-MES and W-MES was equal to 76.82, 69.19 and 66.60 %, respectively. The disalt, RCH(CO 2 Na)SO 3 Na, contents were instead 3.2, 3.8 and 4.7 %, respectively. As proved by the results of the FTIR and NMR characterizations, the chemical structure of W-MES is almost the same as that of S-MES and R-MES. The critical micelle concentration of W-MES is 5.38 mmol/L and the corresponding surface tension is 32.3 mN/m. The hydrophile-lipophile balance value of W-MES is 12.33, which indicates that it can form oil/water emulsions. The three MES demonstrated the same adsorption efficiency, yielding a pC20 value of 3.22, and similar foam stability. Their detergency can be up to 75 % at a concentration of 400 mg/kg and the tolerance to Ca 2? is higher than the one exhibited by linear alkylbenzene sulphonic acid and alpha olefin sulfonate. Additionally, W-MES shows a considerable solubilization capacity towards polycyclic aromatic hydrocarbon as the molar solubilization ratios to pyrene, phenanthrene and acenaphthene in a 30 mmol/L solution are 1.22 9 10 -3 , 2.67 9 10 -3 and 3.81 9 10 -3 , respectively.

Preparation of a Sulfonic‐Acid‐Type Ordered Mesoporous Carbon Solid Acid via Hydrothermal Synthesis for the Transesterification of Waste Frying Oil

“…[47] FAMEs are also used in the industrial-scale synthesis of socalled green surfactants based on fatty acids. [48] The preparation of FAMEs generally involves the transesterification reaction of vegetable oils or waste cooking oils with methanol in the presence of acid or alkali catalysts. [49] Because waste cooking oil will normally contain some amount of free fatty acids, which readily undergo saponification in the presence of alkali catalysts, acid catalysts are more suitable for the preparation of FAMEs via transesterification.…”

Selective Syntheses and Properties of Anionic Surfactants Derived from Isosorbide

“…The reaction between alkyl bromide and lithium hydroxide in DMSO at 90 °C produced 72% D, 3% E, and 6% F (D:E ratio of 24:1) after 3 h, showing the highest selectivity. Zhu et al performed an alkylation of isosorbide using lithium hydroxide in DMSO, and obtained 5% D and 32% E after separation and purification (Jin et al, ). Abenhaïm's group performed this reaction with lithium hydride in Dimethylformamide (DMF) with ultrasound, and the reaction yielded 5% D, 60% E, and 15% F. Owing to the effects from the solvent, the bases showed a selectivity order of Li + > Na + > K + (Abenhaïm et al, ).…”

“…However, because APG is currently priced higher than alkylphenolethoxylates, it is only used for specialized purposes such as cosmetics, medicines, and food (Roussel et al, ; Rybinski and Hill, ). Another example of sustainable, eco‐friendly surfactant is fatty‐acid methyl ester sulfonate, which can be easily synthesized using biological oils as raw material, and is widely used in the chemical industry on account of its great surface activity and self‐assembly behavior (Jin et al, ).…”

Sulfonic Acids Supported on UiO-66 as Heterogeneous Catalysts for the Esterification of Fatty Acids for Biodiesel Production

“…Fatty acid esters are derivatives of fatty acids that play an important role in daily life and industrial production [1,2]. The main applications of fatty acid ester products are industrial washing solvents, lubricants, surfactants, plastic processing additives, cosmetic additives and so on [3][4][5]. More importantly, fatty acid esters, including fatty acid methyl esters, fatty acid ethyl esters and fatty acid butyl esters, are a class of biodiesel, used as a renewable energy source [6][7][8].…”