Synthesis, Surface Properties, and Hydrolysis of Chemodegradable Anionic Surfactants: Diastereomerically Purecis- andtrans-2,5-Disubstituted-1,3-dioxanes

Piasecki, Andrzej; Sokołowski, Adam; Burczyk, Bogdan; Gancarz, Roman; Kotlewska, Urszula

doi:10.1006/jcis.1997.4967

Cited by 7 publications

(10 citation statements)

References 27 publications

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“…Furthermore, the influence of the polar carbonyl group configuration in molecules of 3 upon the rate of hydrolysis in an acidic medium is opposite to that already obtained for other diastereomeric 1,3-dioxane derivatives (25)(26)(27), i.e., cis isomers of 3 hydrolyze faster than trans isomers. It can be explained by taking into account the modeled structures of cis-3 and trans-3 (Fig.…”

Section: Hydrolysis/isomerizationcontrasting

confidence: 47%

“…• C) with those already obtained for nonmicellizing cis-and trans-2-n-alkyl-5-hydroxy-1,3-dioxanes (27) and micellizing diastereomeric 1,3-dioxane derivatives containing at the C5 carbon atom polar sodium sulfate group (25,26) or sodium sulfonate group (25), it can be seen that, investigated here, isomeric sodium salts 3 are more resistant to hydrolysis. Furthermore, the influence of the polar carbonyl group configuration in molecules of 3 upon the rate of hydrolysis in an acidic medium is opposite to that already obtained for other diastereomeric 1,3-dioxane derivatives (25)(26)(27), i.e., cis isomers of 3 hydrolyze faster than trans isomers.…”

Section: Hydrolysis/isomerizationmentioning

confidence: 54%

“…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: 83%

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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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Section: Hydrolysis/isomerizationcontrasting

confidence: 47%

Section: Hydrolysis/isomerizationmentioning

confidence: 54%

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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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“…The present work introduces a further reasoning to the above idea. Its main purpose was to describe quantitatively the way in which the packing of two surfactants, namely twin-tailed AOT and single-tailed sodium cis - or trans -(2- n -alkyl-1,3-dioxan-yl) sulfates (cis-C n and trans-C n in Figure ) or sodium alkyl sulfates (C n OSO 3 Na), affects the interfacial tensions γ c in mixed adsorbed films. The application of anionics other than SDS, especially those differing in geometrical structure, could increase variety and effectivity of thermodynamically stable Winsor II−Winsor III−Winsor I system transitions.…”

Section: Introductionmentioning

confidence: 99%

Adsorption of Diastereomerically Pure Sodium cis- and trans-(2-n-Alkyl-1,3-dioxan-5-yl) Sulfates at the n-Heptane−Water Interface

et al. 1999

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A systematic study concerning adsorption and aggregation of chemodegradable, diastereomerically pure sodium cis-and trans- (2-n-alkyl-1,3-dioxan-5-yl) sulfates (alkyl: n-C 9 H 19 and n-C 11 H 23 ) in the system consisting of n-heptane in contact with aqueous 0.2 M NaCl at 31°C has been undertaken. The role of the six-membered 1,3-dioxane ring has been discussed in terms of comparison between studied surfactants and "classical" sodium decyl and dodecyl sulfates. Surface parameters of compounds under study at the oil-water interface, i.e., surface tension reduction (π), surface excess concentration (Γ), surface area demand per molecule (A), critical micelle concentration (cmc), standard free energy of adsorption (∆G o ads ), and of micellization (∆G o cmc ), show differences due to the alkyl chain length and to the hydrophilic, i.e., sulfate group configuration at the C-5 atom of the 1,3-dioxane ring. The cmc, ∆G o ads , and ∆G o cmc values are lower for the trans isomers than for the cis ones, whereas the effectiveness of surface tension reduction is nearly the same for both isomers. Additionally, the interfacial tensions of the studied acetal-type isomers have been described for the heptaneaqueous NaCl systems containing Aerosol OT. According to our findings the configuration of the -OSO 3 -Na polar group at the C-5 carbon atom of the 1,3-dioxane ring, i.e., equatorial in trans isomers and axial in cis isomers, involves diastereomeric differentiation in the aggregation abilities.

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“…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).…”

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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Synthesis, Surface Properties, and Hydrolysis of Chemodegradable Anionic Surfactants: Diastereomerically Purecis- andtrans-2,5-Disubstituted-1,3-dioxanes

Cited by 7 publications

References 27 publications

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

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

Adsorption of Diastereomerically Pure Sodium cis- and trans-(2-n-Alkyl-1,3-dioxan-5-yl) Sulfates at the n-Heptane−Water Interface

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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