Oxyethylation of Fatty Acid Methyl Esters. Molar Ratio and Temperature Effects. Pressure Drop Modeling

Abstract

The effect of reagent molar ratio and temperature upon the composition of oxyethylated fatty acid methyl esters and surface tension reduction at air/water interfaces was studied. It was found that oxyethylation of fatty acid methyl esters carried out in the presence of calciumbased catalyst gives narrow range distributed products. The distribution depends on temperature, and more narrow products are obtained at higher temperatures. Oxyethylated fatty acid methyl esters contain less unreacted hydrophobic starter than oxyethylated alcohols. The pressure drop in the batch process can be satisfactorily modeled, assuming the reaction proceeds in the liquid phase and estimating the concentration of the ethylene oxide in the liquid phase from vaporliquid equilibrium. The modeling supports the important role of ethylene oxide diffusion from the gas to the liquid phase. The distribution of the polyoxyethylene chain in hydrophilic oxyethylated fatty acid methyl esters has only a minor effect upon the surface tension reduction and the values of characteristic adsorption coefficients. The effect of the synthesis temperature is not reflected in the surface tension reduction.

Rheological Behavior of Selected Water‐Nonionic–Anionic Surfactant Quasi‐ternary Systems

“…• rapeseed acid methyl ester ethoxylated with 10 mol of ethylene oxide (RAMEO), prepared by the ethoxylation of suitable rapeseed acid methyl ester (Biodiesel Producers Association); the preparation method as well as analytical characteristics (HPLC, GC) of the product were described in [11,18]; • dodecanoic (lauryl) acid methyl ester ethoxylated with 10 mol of ethylene oxide (LAMEO), prepared by ethoxylation of suitable dodecanoic acid methyl ester (EDENOR 12, 98-100 Henkel, Germany); the preparation method as well as analytical characteristics (HPLC, GC) of the product were described in [17,18]; • coconut oil fatty acid methyl ester ethoxylated with 10 mol of ethylene oxide (CAMEO), prepared by ethoxylation of commercial coconut oil fatty acid methyl ester (EDENOR PK-12-18F, Henkel Germany); the preparation method as well as analytical characteristics (HPLC, GC) of the product were described in [11]. • linear dodecylbenzenesulfonic acid (LABSA), manufactured commercially by Henkel Polska production plant through the sulfonation of linear (C 10 -C 13 )alkylbenzene with sulfur trioxide, employing the Ballestra SULPHUREX Ò process.…”

“…Another very important reason why this group of surfactants are so interesting to the market, in contrast to others, so to say, traditional detergent components, is the regular development of methods to improve their detergency by modifying the parameters of distribution of the content of the various fractions of the ethoxylate homolog series, leading to the determining of ethoxylate having what is called a narrow distribution range [12][13][14]. It also is important that techniques for direct ethoxylation of fatty acid esters have been discovered and improved [15][16][17][18]. This last aspect is especially important, given the appearance during the last decade, of a new raw material base in connection with the occurrence of favorable conditions for the implementation of a technological process to manufacture fuels based on fatty acid methyl esters obtained by refining vegetable oils (for instance, rapeseed oil).…”

Surfactants Based on Natural Fatty Acids

“…Furthermore, the technique has also been shown to be applicable to ethoxylation of several types of fatty acid esters like triglycerides or branched alkyl esters [62,64], as well as for propoxylation of fatty acid esters [65]. Alejski et al [66,67] and Bialowas and Szymanowski [68] have contributed to the understanding of how the oxyethylation reaction of fatty acid methyl esters proceeds in stepwise incorporation of the ethylene oxide units. In particular, the ethoxylation of inexpensive methyl esters of common oils like that of rapeseed oil (rapeseed oil methyl ester, or RME) have been attractive, because of the increasing production of this ester as a biodiesel alternative in Europe [69,70].…”

Interfacial Tensions of Ethoxylated Fatty Acid Methyl Ester Solutions Against Crude Oil

“…Compared to ethoxylated alcohols, they have better properties, lower aquatic toxicity and higher biodegradability [27,28]. They also possess excellent surface activity, for example the surface tension of ethoxylated fatty acid methyl ester (MRAEO 15 ) is 35.5 mN/m [29]. This kind of surfactant has been considered as a model of new prospective nonionic surfactants which can be obtained by direct reaction of fatty acids methyl esters with ethylene oxide in the presence of appropriate catalysts.…”