2-Ethylhexyl laurate, as an exemplary longerchain aliphatic ester, was subjected to direct ethoxylation. The synthesis was described and the obtained products were analyzed qualitatively by means of the mass spectrometry and chromatographic methods. Solubility of the obtained ethoxylates was studied by determination of their cloud points in selected model solutions. It was shown that longer-chain aliphatic esters are feasible as raw materials for ethoxylation in the presence of an appropriate catalyst. They undergo effective and selective reaction with ethylene oxide without formation of excessive amounts of by-products. The obtained products exhibit typical properties of ethoxylate-type nonionic surfactants. Their solubility in water and butyldiglycol solution was relatively lower compared to their methyl ester equivalents.Paper no. S1226 in JSD 4, 167-173 (April 2001).KEY WORDS: Aliphatic esters, ethoxylation, 2-ethylhexyl laurate.The common definition of ethoxylation requires the presence of a labile hydrogen group in the substrate subjected to the reaction, according to Equation (1):where R denotes hydrocarbon chain and X means an intermediate group, such as -O-, -N-, or -S-. However, it was found recently that the reaction can also be performed efficiently with fatty acid methyl ester as the substrate (2,3). Since then several catalysts that allow efficient performance of the reaction have been reported (4-6). Ethoxylation of fatty methyl esters was also carried out using the conventional alkaline catalysts (7), although the rate of ethylene oxide (EO) addition was slow and the product distribution obtained was broad. It was proven that during ethoxylation of fatty methyl ester, EO was inserted selectively between the carbonyl carbon and the methoxy group (8).RCOOCH 3 + nCH 2 CH 2 O → RCO(OCH 2 CH 2 ) n OCH 3[2] Substrate Adduct Ethoxylation product Propoxylation of fatty acid methyl esters was also reported in the literature (9). Earlier studies described the impact of methyl ester chain length, degree of unsaturation, and EO content on the physical properties and performance of methyl ester ethoxylates (7,10,11). However, in considering the more recently described effective ethoxylation of the ester bond, a wide spectrum of additional raw materials appears to be relevant for the manufacture of nonionic surfactants. Some of them are already available commercially. They include longer aliphatic esters applied as ecological organic solvents, lubricants, modern bio-fuel additives, or other auxiliary agents. The aim of this work was to present the results from direct ethoxylation of 2-ethylhexyl laurate as an exemplary longer-chain aliphatic ester subjected to the reaction and to study the solubility of the products obtained in water and in 2-(2-butoxyethoxy)ethanol (butyldiglycol: BDG) solution. EXPERIMENTAL PROCEDURESThe following materials were used: oxirane (Mazovian Petrochemical Works, P / lock, Poland); 2-ethylhexyl laurate, marked as Polcet L (CHEMCO Production and Trade Company, Sobowidz, Poland); and ...

The effect of catalyst (potassium hydroxide, triethylamine, and sulfuric acid) on oxyethylation and oxypropylation of methanol, ethanol, and butanol is studied. Exemplary optimization of the process is performed at selectivity equal to 90% of the monoglycol alkyl ether fraction. It is shown that the most advantageous for oxyalkylation of methanol are the alkaline catalysts, especially triethylamine. The same relationship was observed for oxypropylation of ethanol and butanol. However, in oxyethylation of ethanol and butanol much better results are obtained using sulfuric acid as the catalyst.

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