Optimization of HPLC Conditions to Analyze Widely Distributed Ethoxylated Alkylphenol Surfactants
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Abstract Commercial ethoxylated alkylphenol surfactants are always a mixture of oligomers with different ethylene oxide number (EON). The different oligomers can be separated by various HPLC techniques. Isocratic mode with mixed solvent on silica column allows to separate oligomers up to EON = 10; gradient programming moves the limit up to EON = 15. For higher EON values (up to 25) a NH2 column has to be used, either with isocratic or gradient mode. Applications to the analysis of microemulsion systems and to the separation of tributyl phenol ethoxylates are discussed. Extreme separation of wide range EON distribution is attained with two columns (Si and NH2) in series, and a solvent programming.Keywords:
Alkylphenol
Oligomer
Microemulsion
This report deals with study of detergency of nonionic surfactant to asphaltic soil with non-polar solvent to which nonionic surfactant is added to determine detergency of surfactant in organic solvents.Among the agents tested markedly effective were those of alkylamine-ethylene oxide condensates, particularly those in which gram moles of ethylene oxide were 4 moles or less.In addition, n-alkylmercaptane-4 moles ethylene oxide condensates indicated fairly good results; while higher alcohol and alkylphenol-ethylene oxide condensates did not yield so good effects.It was also found that anionic surfactants were much inferior to those described above.
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Although poly(oxyethylene)alkylphenyl ether (APE) nonionic surfactants with longer ethylene oxide (EO) chain than 2 can be the important pollutants in natural aquatic environments as the potential precursor of alkylphenol, an endocrine disrupting chemical, little attention has been paid to those. Water samples were seasonally collected at five sites of each of the three main rivers in Tokyo. APE with different alkyl chains were separated and fractionated using a reversed-phase adsorption enrichment technique with gradient elution in high performance liquid chromatography (HPLC). After the concentration of each fraction, EO chain length (polymerization degree of EO) in APE was determined by electrospray ionization mass spectrometry (ESI/MS). The results indicated that, in three main river waters in Tokyo, poly(oxyethylene)nonylphenyl ether (NPE) was the dominant pollutant among APE, total NPE concentrations with different EO chain lengths were 2−6 nM in summer and 10−35 nM in winter, and its peak in the abundance of NPE components with different EO chain lengths was at 5−8 EO units in winter and shifted to 2−5 units in summer. Laboratory biodegradation experiments using filtered and NPE-spiked river water confirmed that seasonal changes in the abundance of NPE components with different EO chain lengths would be mainly caused by increased bacterial activity due to high water temperature, producing mainly the persistent nonylphenol diethoxylate.
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Summary The foam stability of several light‐duty liquid dishwashing formulations containing sulfated ethoxylates of tridecyl alcohol, lauryl alcohol, and nonylphenol have been compared. The effects of water hardness, sulfating agent, and ethylene oxide/hydrophobe mole ratio have been examined. In very soft water formulations containing alkanolamide and tridecyl alcohol derivatives were shown to be especially effective. At higher water‐hardnesses, combinations containing sulfated ethoxylates of tridecyl alcohol and nonylphenol performed best. Optimum ethylene oxide content for the sulfated tridecyl alcohol ethoxylates has been shown to be 4 to 5 moles/mole of alcohol regardless of water hardness or detergent concentration. The alcohol ethoxylates were shown to be more tolerant of stronger sulfating agents with respect to product quality than the alkylphenol ethoxylates.
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Alkylphenol
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Summary. Several alkylphenol ethylene oxide ether non‐ionic surfactants were tested in aqueous foliar sprays with dalapon, amitrole and paraquat for (heir enhancement of phytocidal activity against Zea mays L. With three homologous series of surfactants studied (octyl‐, nonyl‐ and laurylphenol types), the herbicide, the surfactant concentration and the hydrophilic constitution (ethylene oxide content) of the surfactant molecule all markedly influenced maximum toxicity. Smaller apparent differences in effectiveness were also attributable to the hydrophobic (alkylphenol) portion of the surfactant. The results arc discussed in relation to possible cuticle‐spray solution interactions and their influence on herbicide penetration. Relations entre la structure et l'activite de produits tensio‐actifs non ionigues, a base d'éther d'oxyde éthylénique et d'alkylphénol, en présence de trois herbicides hydrosolubles
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The reactivity of phenol under noncatalytic conditions with propionaldehyde, acetone, and propionic acid were determined in the presence of water at supercritical conditions and in the absence of water at 673 K. The reaction of phenol with propionaldehyde gave alkylphenols in supercritical water. The yield of the alkylphenol products and ratio of para isomers to ortho ones increased with increasing water density. Over the range of reaction conditions studied, acetone showed no reactivity with phenol regardless of whether water was present or not. The reaction of propionic acid with phenol yielded the corresponding ester in the absence of water.
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The toxicity of 22 commercial surfactants was assessed because of the possibility that these materials may contact food. Among these surfactants the ethylene oxide chain lengths ranged from 4-40 and the alkylphenols included di(seconday butyl) octyl nonyl and dodecyl. 3 products were given to rats and dogs in a diet for 2 years 13 were given to rats for 90 days and 8 were given to dogs for 90 days. In rats absorption and elimination of the 2 products were studied. As a result of the 90-day feedings no effects were found for: nonyl 4--rats and dogs at .4 gm/kg/day; nonyl 6--rats < .04 dogs .04% in diet; dodecyl 6-- < .04; octyl 9--rats .3 dogs < .04; nonyl 9--rats .01 dogs .04% in diet; dodecyl 9--rats .04; nonyl 15--rats and dogs .04; nonyl 20--rats 1 dogs < .04%; nonyl 30--rats 5 dogs 1; octyl 40--rats and dogs 5% in diet; nonyl 40--rats .3% in diet; di(sec-butyl)40--rats 1% in diet; dodecyl 40--rats 5%. The effect at the next highest level fed was focal myocardial necrosis for nonyl 20 but was only trivial for the other samples. No effect was found in 2 years from nonylphenol ethylene oxide 9 on rats at .14 or dogs at .03 gm/kg/day in the diet; from nonylphenol ethylene oxide 4 at .2 and .04 respectively; or from octylphenol ethylene 40 on rats at .7 gm/kg/day. No carcinogenic effect was found in any feeding test. In dogs but not in rats there was nonprogressive myocardial toxicity from oral doses apparently a direct pharmacodynamic effect on the heart muscle proportional to the content of ethers with ethylene oxide chains 20 units in length. This effect was marked in products with an average chain length of 20 but was not detected with averages of 12 or 25.
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Abstract A model compound representing the nonionic surfactants of the alkylphenol‐ethylene oxide condensate type was prepared in high purity. The homogeneous detergent p‐n ‐nonylphenoxyde‐caethoxyethanol was obtained as a crystalline product by a several step synthesis starting from phenol.
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Abstract The hard‐surface cleaning performance of various nonionic homologs was evaluated as a function of carbon chain length, ethylene oxide (EO) content, blending and concentration. Results show carbon chain length to be very important to hard‐surface cleaning. Performance significantly increases as carbon‐chain length decreases, probably as a result of an increase in solvency properties as carbon chain length is decreased. EO content is also important, particularly if nonionics with longer carbon chain lengths are used. Surfactant concentration (dilution) has little effect on the optimum ethylene oxide content but significantly affects the optimum carbon chain length of the hydrophobe. With 5% homolog solutions, the optimally performing nonionic contains a C6 hydrophobe, but with 0.2% solutions, the optimal carbon chain length is shifted to the C8–C10 range. This is thought to result from a trade‐off between the surfactant and solvent properties of the nonionic. Overall results show the optimal nonionic for hard‐surface cleaning to consist of a blend of C6, C8 and C10 alcohols ethoxylated to a 50% EO level. Commonly used surfactant systems, e.g., alkylphenol ethoxylates and alkylphenol ethoxylate (APE)‐butyl cellosolve (BC) blends, were also examined. Results show that alkylphenol ethoxylates give relatively poor performance compared with lower molecular weight linear nonionics because of the large size of their hydrophobe. Under concentrated use, a synergism does exist between APE and BC, but under dilute conditions, the addition of BC is ineffective. BC does not help the performance of low molecular weight nonionics. Surfactant‐soil diffusion studies indicate that surfactant penetration of the soil may be the primary mechanism involved in the hard‐surface cleaning of solid soils.
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Hydrophobe
Nonylphenol
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Oligomer
Trimethylsilyl
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A method for quantitative determination of trace amounts of alkylphenol ethoxylates (APE) in environmental water is described. Levels of 1 to 3 μg/L can be detected and resolved into their complete oligomer distribution (1EO to 18EO) while maintaining integrity of the oligomer distribution. This is a major improvement over previous methods; for the first time distortion of oligomer distribution due to work‐up conditions of earlier methods has been prevented. Isolation of the APE from water is achieved using a simple and rapid dual‐column procedure. The first column removes interfering ionic materials, the second traps the APE on alkyl‐bonded silica. Assay of the extract employs HPLC with a fluorescence detector. The method was used for analyzing treated waste‐water and river water. A much better picture of the biodegradation behavior of APE in the environment has emerged as a result of keeping APE oligomer distribution intact during sample extraction. There is no accumulation of alkylphenol and the low EO oligomers during wastewater treatment, although the oligomer distribution may become skewed toward these species. Concentrations in the receiving waters examined were very low, in the range of 1–2 μg/L total APE species (OEO to 18EO).
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