Micellization and Adsorption of a Series of Fatty Amide Ethoxylates

Folmer, Britta; Nydén, Magnus; Holmberg, Krister

doi:10.1006/jcis.2001.7782

Cited by 11 publications

(1 citation statement)

References 15 publications

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“…Both vertebrate and invertebrate surfactants contain a lipid moiety conjugated via an amide bond to an amino acid. Amide bonds tend to make surfactants more stable in alkaline solutions (35) and form smaller micelles (36). In vertebrates, the lipid moiety is sterol-based (37), while in invertebrates it is fatty acid-based (9,38).…”

Section: Discussionmentioning

confidence: 99%

Commercially Available Chemicals That Mimic a Deposit Feeder's (Arenicola marina) Digestive Solubilization of Lipids

Voparil

Mayer

2004

Environ. Sci. Technol.

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To develop a simple and cost-effective bioavailability test for sediment-bound contaminants, the solubilization strengths of mixtures of four commercially available surfactants and four proteins were compared to that of digestive fluids from a deposit-feeding benthic polychaete Arenicola marina. Initial tests indicated that sodium taurocholate, a vertebrate bile salt, was the most accurate mimic of A. marina gut fluids' solubilization of individual polycyclic aromatic hydrocarbons (PAH). Further testing with nutritional lipids and other hydrophobic contaminants confirmed the similarities of these fluids. Bovine serum albumin (BSA) solubilization of PAH was the most efficient of all the proteins tested. A cocktail of sodium taurocholate and BSA was compared to A. marina's solubilization of 12 PAH from four different contaminated sediments (from Boston, Charleston, Jacksonville, and San Diego harbors). The two solutions released most PAH to similar extents; 40 of 48 PAH-sediment combinations were released at amounts within a factor of 2 in cocktail and gut fluid solutions. Therefore, the cocktail may serve as a surrogate for real gut fluids and allow easier adoption of the in vitro incubation approach to bioavailability testing.

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Section: Discussionmentioning

confidence: 99%

Commercially Available Chemicals That Mimic a Deposit Feeder's (Arenicola marina) Digestive Solubilization of Lipids

Voparil

Mayer

2004

Environ. Sci. Technol.

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Amides, Fatty Acid

Johansson

2003

Kirk-Othmer Encyclopedia of Chemical Technology

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Fatty acid amides, which contain a saturated or unsaturated alkyl chain derived from a fatty acid, can be divided into three categories. The first is primary monoamides in which R is a fatty alkyl or alkenyl chain of C 5 C 23 and R′ = R″ = H. The second is substituted monoamides, including secondary, tertiary, and alkanolamides in which R is a fatty alkyl or alkenyl chain of C 5 C 23 ; R′ and R″ may be a hydrogen, fatty alkyl, aryl, or alkylene oxide condensation groups with at least one alkyl, aryl, or alkylene oxide group. The third category is bisamides where R groups are fatty alkyl or alkenyl chains. R′ and R″ may be hydrogen, fatty alkyl, aryl, or alkylene oxide condensation groups. Primary and secondary amides show strong hydrogen bonding that account for their high melting points and low solubilities in most solvents. With tertiary amides (disubstituted amides), hydrogen bonding is not possible, as exhibited by their increased solubility and lower melting points. Many fatty acid amides are essentially insoluble in water. Amides have a strong tendency to reduce friction on various surfaces by forming a layer on surfaces. This coating action may be attributed to their hydrophobic character and strong hydrogen bonding. Primary, secondary, and bisamides are widely used as lubricating or slip agents and alkanolamides. Their ethoxylated counterparts are commonly used as surfactants in personal care and detergent applications. Amides in general are stable to elevated processing temperatures, air oxidation, and dilute acids and bases. The dehydration of amides that produces nitriles is of great commercial value. The most widely used synthetic route for primary amides is the reaction of a fatty acid with anhydrous ammonia. Alkanol amides are made from triglycerides or fatty acid methyl esters reacted with monoethanolamine or diethanolamine that then can be ethoxylated with ethylene oxide under basic catalyses. Common products are stearamide, cocamide, ethylene bis(stearamide), cocamide, DEA or MEA, cocamidopropyl dimethyl amine, and cocamide monoethanolamine ethoxylate.

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Characterizations of surfactant synthesized from Jatropha oil and its application in enhanced oil recovery

Kumar

Mandal

2017

AIChE Journal

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Surfactants are frequently used in chemical enhanced oil recovery (EOR) as it reduces the interfacial tension (IFT) to an ultra‐low value and also alter the wettability of oil‐wet rock, which are important mechanisms for EOR. However, most of the commercial surfactants used in chemical EOR are very expensive. In view of that an attempt has been made to synthesis an anionic surfactant from non‐edible Jatropha oil for its application in EOR. Synthesized surfactant was characterized by FTIR, NMR, dynamic light scattering, thermogravimeter analyser, FESEM, and EDX analysis. Thermal degradability study of the surfactant shows no significant loss till the conventional reservoir temperature. The ability of the surfactant for its use in chemical EOR has been tested by measuring its physicochemical properties, viz., reduction of surface tension, IFT and wettability alteration. The surfactant solution shows a surface tension value of 31.6 mN/m at its critical micelle concentration (CMC). An ultra‐low IFT of 0.0917 mN/m is obtained at CMC of surfactant solution, which is further reduced to 0.00108 mN/m at optimum salinity. The synthesized surfactant alters the oil‐wet quartz surface to water‐wet which favors enhanced recovery of oil. Flooding experiments were conducted with surfactant slugs with different concentrations. Encouraging results with additional recovery more than 25% of original oil in place above the conventional water flooding have been observed. © 2017 American Institute of Chemical Engineers AIChE J, 63: 2731–2741, 2017

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Micellization and Adsorption of a Series of Fatty Amide Ethoxylates

Cited by 11 publications

References 15 publications

Commercially Available Chemicals That Mimic a Deposit Feeder's (Arenicola marina) Digestive Solubilization of Lipids

Commercially Available Chemicals That Mimic a Deposit Feeder's (Arenicola marina) Digestive Solubilization of Lipids

Amides, Fatty Acid

Characterizations of surfactant synthesized from Jatropha oil and its application in enhanced oil recovery

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