Sustainable oleic and stearic acid based biodegradable surfactants

Bhadani, Avinash; Iwabata, Kazuki; Sakai, Kenichi; Koura, Setsuko; Sakai, Hideki; Abe, Masahiko

doi:10.1039/c6ra27036k

Cited by 49 publications

(32 citation statements)

References 52 publications

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“…These results are consistent with experimental data where water-air surface tension calculated for oleyl surfactant (unsaturated with cis conformation) is lower than that of stearyl surfactant. 86 In that study, Bhadani et al 86 suggested that the decrease in the IFT of the oleyl surfactant is probably due to cation-p interactions between the CQC double bond and the surfactant headgroup.…”

Section: Temperature Effects On Interfacial Tensionmentioning

confidence: 98%

“…Experimental observations indicate that surfactants with unsaturated alkyl chains induce lower surface/interfacial tension than those with saturated alkyl chains of equivalent chain length. 85,86 To provide a solid scientific basis for those observations, a double bond was added to the middle of the SDS alkyl tail (between carbon numbers 6 and 7), and then the IFT was calculated and correlated to the interfacial film's molecular properties. We expect that adding a double bond to the SDS surfactant tails will increase the disorder of the interfacial film, inspired by the fact that vegetable oils with double bonds in the hydrophobic tails have lower melting temperature than animal fat (with saturated tails) of the same length due to their low chain packing efficiency, 87 thus further reducing the IFT.…”

Section: Temperature Effects On Interfacial Tensionmentioning

confidence: 99%

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Water/oil interfacial tension reduction – an interfacial entropy driven process

Bui

Frampton

Huang

et al. 2021

Phys. Chem. Chem. Phys.

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Section: Temperature Effects On Interfacial Tensionmentioning

confidence: 98%

Section: Temperature Effects On Interfacial Tensionmentioning

confidence: 99%

Water/oil interfacial tension reduction – an interfacial entropy driven process

Bui

Frampton

Huang

et al. 2021

Phys. Chem. Chem. Phys.

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“…Polymers obtained from renewable raw material sources biodegrade under controlled conditions, for example under composting conditions or through fermentation. In this context, the biodegradability of an oleic acid-based compound has been recently assessed by the biochemical oxygen demand (BOD) method using activated sludge and found to be readily biodegradable [ 31 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Partially Renewable Oleic Acid-Based Ionomers for Proton Exchange Membranes

et al. 2020

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The future availability of synthetic polymers is compromised due to the continuous depletion of fossil reserves; thus, the quest for sustainable and eco-friendly specialty polymers is of the utmost importance to ensure our lifestyle. In this regard, this study reports on the use of oleic acid as a renewable source to develop new ionomers intended for proton exchange membranes. Firstly, the cross-metathesis of oleic acid was conducted to yield a renewable and unsaturated long-chain aliphatic dicarboxylic acid, which was further subjected to polycondensation reactions with two aromatic diamines, 4,4′-(hexafluoroisopropylidene)bis(p-phenyleneoxy)dianiline and 4,4′-diamino-2,2′-stilbenedisulfonic acid, as comonomers for the synthesis of a series of partially renewable aromatic-aliphatic polyamides with an increasing degree of sulfonation (DS). The polymer chemical structures were confirmed by Fourier transform infrared (FTIR) and nuclear magnetic resonance (1H, 13C, and 19F NMR) spectroscopy, which revealed that the DS was effectively tailored by adjusting the feed molar ratio of the diamines. Next, we performed a study involving the ion exchange capacity, the water uptake, and the proton conductivity in membranes prepared from these partially renewable long-chain polyamides, along with a thorough characterization of the thermomechanical and physical properties. The highest value of the proton conductivity determined by electrochemical impedance spectroscopy (EIS) was found to be 1.55 mS cm−1 at 30 °C after activation of the polymer membrane.

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“…Poor selectivity of the product, in case of catalyst 3 , is due to the absence of sufficient olefinicity (only single cis ‐pi bond) failed to stabilize the inner core during enamine formation. It has been observed that amount of catalyst loaded for the reaction is one of the factors that control the selectivity− and the enantioselective reactions proceed under kinetic control when low %loading of catalyst is used. Rulli et al reported shift from kinetic to thermodynamic controlled regime through variation in loading of Singh's catalyst 8 (0.5 to 10 mol%) in water .…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Direct Aldol Reaction in Confined Space: Molecular Conformations of Organocatalyst Affect Chiral Induction

et al. 2019

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We have demonstrated that chiral induction in the aldol product is possible by generating an enzyme‐like cavity in molecular framework of the amphiphlic catalyst. The esters of trans‐4‐hydroxy‐L‐proline and long chain fatty acids have been synthesized by O‐acylation. Synthesized molecules were used as organocatalysts for asymmetric direct aldol reaction between 4‐nitrobenzaldehyde and cyclohexanone. The molecular framework of the catalyst not only induces the amphiphilicity but also acquires specific conformation leads to formation of catalytic cavity facilitating stereo‐induction in the aldol product. Systematic addition of olefinic bonds in the long hydrocarbon chain makes this cavity more robust stabilizing transition state of the aldol product. By proper tuning of the water content and % loading of the catalyst in aldol reaction, o/w or w/o type emulsion is formed due to aggregation of catalyst molecules. Performance based evaluation of catalytic activity suggests that aldol reaction proceeds with ∼ 99% yield, 84% dr and 97.94% ee in presence of 10% catalyst (having three π bonds), in an o/w emulsion (85 equiv. of water) within 12 h. The stereoselectivity of the catalyst is almost maintained up to 2.5% loading. The high stereoselectivity of the aldol reaction is maintained even on increasing the amount of water to 300 equiv. A plausible reason has been proposed for retaining the high stereoselectivity and corroborated by computational analysis.

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Sustainable oleic and stearic acid based biodegradable surfactants

Abstract: Renewable ester functionalized fatty acid based imidazolium surfactant.

Cited by 49 publications

References 52 publications

Water/oil interfacial tension reduction – an interfacial entropy driven process

Water/oil interfacial tension reduction – an interfacial entropy driven process

Synthesis and Characterization of Partially Renewable Oleic Acid-Based Ionomers for Proton Exchange Membranes

Asymmetric Direct Aldol Reaction in Confined Space: Molecular Conformations of Organocatalyst Affect Chiral Induction

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