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Various triglycerides (coconut oil, palm kernel oil, tallow) were ethoxylated with a proprietary catalyst (calcium/aluminum alkoxide complex partially neutralized in an alcohol ethoxylate base) to obtain triglyceride ethoxylates. Triglyceride ethoxylates were then partially saponified with sodium hydroxide to form mixtures of mono-, di-, and triglyceride ethoxylates, fatty acid soap, and glycerol ethoxylate. These mixtures were characterized in terms of physical properties, surface activity, and mildness. Partially saponified triglyceride ethoxylates were found to be unexpectedly mild and capable of imparting mildness to other surfactants.Paper no. S1157 in JSD 3, 213-220 (April 2000).Ethoxylation is the most common method for adding a nonionic hydrophile to an organic hydrophobe. Prior to 1989, substrates suitable for ethoxylation were thought to require a labile hydrogen, most commonly a hydroxyl hydrogen, in order for ethoxylation to occur. In the late 1980s, the concept of ethoxylating esters was introduced by Hoechst and Henkel (1,2). Hoechst demonstrated that ethoxylation of esters was feasible using catalysts based on alkali and alkali earth metals (e.g., sodium hydroxide, sodium methoxide, barium hydroxide, etc.), while Henkel showed that calcined hydrotalcite (aluminum/magnesium oxide complexes) had potential as well. Relatively poor reactivities and conversions, however, prevented these catalysts from being utilized commercially. In the early 1990s, Vista Chemical Company (now CON-DEA Vista Company, Houston, TX) developed a commercially viable process for ethoxylating esters (3). Their process utilized a more complex alkoxylation catalyst (activated calcium and aluminum alkoxides) that efficiently and effectively inserted ethylene oxide between the carbonyl carbon and the ester oxygen. Immediately thereafter, Lion Corporation (Tokyo, Japan) demonstrated that a magnesium/aluminum oxide-based catalyst also worked well (4). Since then, the development and use of ester alkoxylates have become an active area of research (5-22). This paper deals with an extension of ester alkoxylation technology. Previous studies have demonstrated that the CONDEA Vista catalyst (a calcium and aluminum alkoxide complex partially neutralized in an alcohol ethoxylate base) can be used to ethoxylate esters, including triglycerides (5,13-16). It is also known that mono-and diglyceride ethoxylates are mild surfactants (23). The object of this research was first to prepare triglyceride ethoxylates and then partially saponify them to obtain a mild surfactant blend of mono-, di-, and triglyceride ethoxylates and fatty acid soap. It was thought that such a blend would make a lower-cost surfactant for mild personal-wash bars, pastes, and gels. This paper details our initial studies on partially saponified triglyceride ethoxylates (PSTE). It describes the preparation and cursory assessment of PSTE made from three different triglycerides. The impacts of surfactant structure (carbon chain length, unsaturation, degree of ethoxylation, degre...
Various triglycerides (coconut oil, palm kernel oil, tallow) were ethoxylated with a proprietary catalyst (calcium/aluminum alkoxide complex partially neutralized in an alcohol ethoxylate base) to obtain triglyceride ethoxylates. Triglyceride ethoxylates were then partially saponified with sodium hydroxide to form mixtures of mono-, di-, and triglyceride ethoxylates, fatty acid soap, and glycerol ethoxylate. These mixtures were characterized in terms of physical properties, surface activity, and mildness. Partially saponified triglyceride ethoxylates were found to be unexpectedly mild and capable of imparting mildness to other surfactants.Paper no. S1157 in JSD 3, 213-220 (April 2000).Ethoxylation is the most common method for adding a nonionic hydrophile to an organic hydrophobe. Prior to 1989, substrates suitable for ethoxylation were thought to require a labile hydrogen, most commonly a hydroxyl hydrogen, in order for ethoxylation to occur. In the late 1980s, the concept of ethoxylating esters was introduced by Hoechst and Henkel (1,2). Hoechst demonstrated that ethoxylation of esters was feasible using catalysts based on alkali and alkali earth metals (e.g., sodium hydroxide, sodium methoxide, barium hydroxide, etc.), while Henkel showed that calcined hydrotalcite (aluminum/magnesium oxide complexes) had potential as well. Relatively poor reactivities and conversions, however, prevented these catalysts from being utilized commercially. In the early 1990s, Vista Chemical Company (now CON-DEA Vista Company, Houston, TX) developed a commercially viable process for ethoxylating esters (3). Their process utilized a more complex alkoxylation catalyst (activated calcium and aluminum alkoxides) that efficiently and effectively inserted ethylene oxide between the carbonyl carbon and the ester oxygen. Immediately thereafter, Lion Corporation (Tokyo, Japan) demonstrated that a magnesium/aluminum oxide-based catalyst also worked well (4). Since then, the development and use of ester alkoxylates have become an active area of research (5-22). This paper deals with an extension of ester alkoxylation technology. Previous studies have demonstrated that the CONDEA Vista catalyst (a calcium and aluminum alkoxide complex partially neutralized in an alcohol ethoxylate base) can be used to ethoxylate esters, including triglycerides (5,13-16). It is also known that mono-and diglyceride ethoxylates are mild surfactants (23). The object of this research was first to prepare triglyceride ethoxylates and then partially saponify them to obtain a mild surfactant blend of mono-, di-, and triglyceride ethoxylates and fatty acid soap. It was thought that such a blend would make a lower-cost surfactant for mild personal-wash bars, pastes, and gels. This paper details our initial studies on partially saponified triglyceride ethoxylates (PSTE). It describes the preparation and cursory assessment of PSTE made from three different triglycerides. The impacts of surfactant structure (carbon chain length, unsaturation, degree of ethoxylation, degre...
Methyl ester ethoxylates are a new class of ethylene oxide (EO)-derived surfactants. Little is known about the impact of structural variations on their performance properties. The effects of carbon chain length, EO content, the degree of unsaturation of the methyl ester feedstock, and feedstock purity were examined for their impact on both physical properties and surfactant performance properties. Physical properties examined included surface properties (surface tension, critical micelle concentration, surface excess adsorption), melting point, water solubility, viscosity, foam stability, color, clarity, and odor. The impact of molecular structure on performance was examined for various applications, including laundry detergents, dishwashing detergents, and hard-surface cleaners. JSD 1, 11-22 (1998).a Unethoxylated methyl ester (0-mol ethoxymer); NMR, nuclear magnetic resonance; PEG, polyethylene glycol; EO, ethylene oxide. For other abbreviation see Table 1.
Insertion of propylene oxide into methyl esters is accomplished using a proprietary alkoxylation catalyst. The alkoxylation mechanism is believed to involve transesterification between the alkoxylated metal-alkoxide of the catalyst and the ester. Optimal alkoxylation conditions are discussed. The effect of inserting propylene oxide prior to ethoxylation on surface properties and foam performance is examined. JSD 1, 167-175 (1998). KEY WORDS:Fatty methyl ester propoxylates, methyl ester propoxylates, performance, physical properties, propoxylated methyl esters.Annually, approximately 500 million pounds of various propoxylates (excluding those used for making polyurethanes) are used worldwide today (1). Most of this volume is made up of various ethylene oxide (EO)/propylene oxide (PO) block copolymers. The majority of the remaining volume consists of various alcohol ethoxylates which have been "capped" by adding PO to the end of the molecule.The utility of PO lies in the ability of the propoxy group to reduce foaming. These groups are branched, which sterically hinders the capacity of the surfactant to pack at the interface.Until recently, the application of PO (and other alkylene oxides) has been restricted to molecules having an active terminal hydrogen, such as alcohols, alcohol ethoxylates, polyethylene glycols, etc. New alkoxylation catalysts, however, have been developed which effectively insert alkylene oxide into esters between the ester carbonyl and the alkoxy group. These catalysts are described elsewhere (2-9).The purpose of this paper is to detail studies examining the ability of a unique alkoxylation catalyst to insert PO into methyl esters, and the impact of PO on the performance of methyl ester alkoxylates. EXPERIMENTAL PROCEDURESPropoxylation of methyl esters. The alkoxylation catalyst (NOVEL® II) consists of a calcium and aluminum complex partially neutralized in an alcohol ethoxylate base (8). Alkoxylations were performed in conventional alkoxylation equipment using 2.67% catalyst (based on the final weight of the catalyst in the product-batch size 150 g). The alkoxylations were performed in a 600-mL stainless steel autoclave equipped with a magnetic stir bar, an internal cooling line, and thermocouples. The autoclave was placed into a heating block which was controlled using an I 2 R therm-o-watch model TCP3-1200 controller (I 2 R, Inc., Chaltenham, PA). The cooling line in the autoclave was hooked up to either water or air for cooling. Air or water cooling lines were controlled using a therm-o-watch model L9-1500 RTD controller (I 2 R, Inc.). A cooling line was opened or closed, dependent on temperature readings from the autoclave thermocouple. A 500-mL bomb containing the alkylene oxide under 50 pounds (23 kg) of N 2 pressure was connected in parallel with a graduated site-glass and connected to the autoclave via stainless steel tubing.The basic alkoxylation procedure can be broken down into five major steps: (i) charging the EO reservoir, (ii) charging the methyl ester, (iii) removal of moistu...
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