Effects of stereochemistry and alternation on the adsorption properties of surface-active cis- and trans-2-n-alkyl-5-hydroxy-1,3-dioxanes

Lunkenheimer, Klaus; Burczyk, Bogdan; Piasecki, Andrzej; Hirte, R.

doi:10.1021/la00056a031

Cited by 29 publications

(41 citation statements)

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“…Please note that the A min values for fully or partially dissociated ionic species do not have an unambiguous interpretation since the counterions can also be present in the adsorbed layer and should be accounted for (see discussion below). In any case, the even/odd effects are very distinct and are the strongest ones we have observed so far, comparable only to those found for the homologous series of diastereomeric amphiphiles of the 2-nalkyl-5-hydroxy-1,3-dioxanes and of the sodium n-alkyl sulfates (18,19).…”

Section: Resultssupporting

confidence: 79%

“…However, following our results on the adsorption properties of homologous series of surface-chemically pure amphiphiles, even/odd phenomena seem to be widespread. In fact, we observed this phenomenon for non-ionic (18,31) and ionic (8,19,33) amphiphiles at the air/water as well as at the oil/water (33) interfaces with respect to alternation of the number of the hydrocarbon chain length of the surfactant and of the solvent n-alkanes. We also found even/odd effects for surfactants when the number of their propylene oxide (34) and/or ethylene oxide units (35) was successively increased.…”

Section: Figmentioning

confidence: 76%

“…Also, novel features in the adsorption properties of amphiphiles were detected (18,19,31). However, it should be remembered that neither the Traube nor the Langmuir/Frumkin isotherm is an appropriate model for the adsorption of fully or partly dissociated ionic surfactants (38).…”

Section: Evaluation Of Equilibrium Surface Tension Vs Concentration Imentioning

confidence: 99%

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On the Adsorption Behavior of Soluble, Surface-Chemically Pure Hemicyanine Dyes at the Air/Water Interface

Lunkenheimer

Laschewsky

Warszyński

et al. 2002

Journal of Colloid and Interface Science

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Section: Resultssupporting

confidence: 79%

Section: Figmentioning

confidence: 76%

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On the Adsorption Behavior of Soluble, Surface-Chemically Pure Hemicyanine Dyes at the Air/Water Interface

Lunkenheimer

Laschewsky

Warszyński

et al. 2002

Journal of Colloid and Interface Science

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“…5). Higher surface activity of trans isomers in comparison to cis isomers was usually observed by us for many homologous series of diastereomeric 1,3-dioxane derivatives (24)(25)(26). However, the superiority of trans isomers was independent of the length of the hydrophobic alkyl substituents.…”

Section: Figmentioning

confidence: 54%

Synthesis, Surface Properties, and Hydrolysis of Chemodegradable Anionic Surfactants: Diastereomeric Sodium Carboxylates Derived from 1,3-Dioxane

Piasecki

Ruchała

2000

Journal of Colloid and Interface Science

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“…These hydrophobic intermediates are useful for the synthesis of sulfate-type anionic surfactants with high surface activity. Surface-active 2,5-disubstituted-1,3-dioxane derivatives also are model surfactants with defined chemical and geometric structures used for investigations of the effects of hydrophilic (11)(12)(13) or hydrophobic (8) substituent configuration on surface activity.…”

mentioning

confidence: 99%

Synthesis and surface properties of chemodegradable anionic surfactants: Diastereomeric (2‐n‐alkyl‐1,3‐dioxan‐5‐yl) sulfates with monovalent counter‐ions

Piasecki¹,

Mayhew²

2000

J Surfact & Detergents

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Sodium, potassium and ammonium cis-and trans-(2-n-alkyl-1,3-dioxan-5-yl) sulfates 6-8 (alkyl: n-C 9 H 19 , 6a-8a, and n-C 11 H 23 , 6b-8b) were synthesized in a reaction of aliphatic aldehydes 1a,b with glycerol 2 followed by separation in high yields of individual geometric isomers of cis-and trans-2-n-alkyl-5-hydroxy-1,3-dioxanes, cis-3a,b and trans-3a,b, followed by sulfation with sulfur trioxide-pyridine complex, and finally neutralization with NaOH, KOH, and NH 4 OH, respectively. Physical data of the compounds and some surface properties of 2-nnonyl derivatives, such as critical micelle concentration (CMC), effectiveness of aqueous surface tension reduction (Π CMC ), surface excess concentration (Γ CMC ), and the surface area demand per molecule (A CMC ), were determined. It was shown that the surface activity of these compounds is influenced both by their geometric structure and by the monovalent counter-ion.Paper no. S1164 in JSD 3, 59-65 (January 2000). KEY WORDS:Aliphatic aldehyde, (2-n-alkyl-1,3-dioxan-5-yl) sulfate, 2-n-alkyl-5-hydroxy-1,3-dioxane, cis-trans isomerism, critical micelle concentration, 1,3-dioxane derivative, surface activity.World resources of glycerol obtained primarily from renewable natural oleochemicals are only partly utilized. This is a good motivation for using glycerol for syntheses of high-performance surfactants that are environmentally friendly. Surface-active compounds containing an acetal group are the largest group of chemodegradable surfactants (1-8). They are susceptible to hydrolytic decomposition and are biodegradable (9). Recently, we devised a convenient and simple method for isolating long-chain cisand trans-2-alkyl-5-hydroxy-1,3-dioxanes from four-component mixtures of glycerol acetals (10), i.e., reaction products of long-chain aliphatic aldehydes and glycerol. These hydrophobic intermediates are useful for the synthesis of sulfate-type anionic surfactants with high surface activity. Surface-active 2,5-disubstituted-1,3-dioxane derivatives also are model surfactants with defined chemical and geometric structures used for investigations of the effects of hydrophilic (11-13) or hydrophobic (8) substituent configuration on surface activity.In previous papers, we reported a relationship between surface activity and configuration of the anionic polar group joined to the C-5 carbon atom of the 1,3-dioxane ring: sulfate group in micelle-forming sodium cis-and trans-(2-n-alkyl-1,3-dioxan-5-yl) sulfates (13); methyl sulfate group in sodium cis-and trans-(2-n-undecyl-1,3-dioxan-5-yl)methyl sulfates (14); propanesulfonate group in sodium cis-and trans-3- [(2-n-undecyl-1,3-dioxan-5-yl)oxy]propanesulfonates (14); and carboxylate group in sodium cis-(15) and trans-(2-n-alkyl-5-methyl-1,3-dioxan-5-yl)carboxylates (Piasecki, A., and P. Ruchal / a, unpublished data).Formation of an ionic micelle from monomeric ions results from a balance between hydrophobic interactions of the amphipathic micelle-forming ions and electrostatic interactions between charged hydrophilic parts, as we...

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Effects of stereochemistry and alternation on the adsorption properties of surface-active cis- and trans-2-n-alkyl-5-hydroxy-1,3-dioxanes

Abstract: A systematic study of adsorption properties of cis-and trons-2-n-alkyl-5-hydroxy-1,3-dioxanes

Cited by 29 publications

References 0 publications

On the Adsorption Behavior of Soluble, Surface-Chemically Pure Hemicyanine Dyes at the Air/Water Interface

On the Adsorption Behavior of Soluble, Surface-Chemically Pure Hemicyanine Dyes at the Air/Water Interface

Synthesis, Surface Properties, and Hydrolysis of Chemodegradable Anionic Surfactants: Diastereomeric Sodium Carboxylates Derived from 1,3-Dioxane

Synthesis and surface properties of chemodegradable anionic surfactants: Diastereomeric (2‐n‐alkyl‐1,3‐dioxan‐5‐yl) sulfates with monovalent counter‐ions

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