Synthesis of an ionic sugar-amino acid based surfactant in aqueous media

Esmaeilian, Nima; Dabir, Bahram; Malek, Reza Mohammad Ali; Arami, Mokhtar; Mazaheri, Firooz Mehr

doi:10.1016/j.molliq.2020.114269

Cited by 4 publications

(5 citation statements)

References 21 publications

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“…The commitment to a fully green process has also not yet been fulfilled has these methods still rely on toxic reagents and solvents, and finally, another challenge to overcome are the low yields attained with some processes [37,38,[51][52][53] The synthesis of cationic sugar-based surfactants has been developing since the 40 0 s with the reaction of glucose with amines [54]. Currently, synthetic methods to produce cationic single chain sugar-based surfactants and cationic sugar-based gemini are described in the literature [37][38][39][45][46][47][48][49][51][52][53][55][56][57][58][59][60][61][62]. In the following sections the synthesis of these surfactants will be discussed in detail with the respective yields presented for each reaction pathway after purification.…”

Section: Synthetic Methods For the Production Of Cationic Sugar-based...mentioning

confidence: 99%

“…As the name suggests, single chain surfactants are constituted by a single hydrocarbon chain which can be branched or linear. Most cationic sugar-based surfactants bear a glucose molecule as their hydrophilic group [38,39,49,60], however, surfactants with other sugar molecules in their headgroup have also been described including glucose-d-lactone [47,61], lactobionic acid [61] and lactose [60].…”

Section: Cationic Sugar-based Surfactants With Single Chainmentioning

confidence: 99%

“…The second method, dimethylformamide (DMF) was used as solvent, in the presence of NaHCO 3 as the catalyst. The product was obtained with a 32% yield [49].…”

Section: Cationic Sugar-based Surfactants With Single Chainmentioning

confidence: 99%

See 2 more Smart Citations

Mini-review: Synthetic methods for the production of cationic sugar-based surfactants

Jesus

Alves²,

Fiuza³

et al. 2021

Journal of Molecular Liquids

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Section: Synthetic Methods For the Production Of Cationic Sugar-based...mentioning

confidence: 99%

Section: Cationic Sugar-based Surfactants With Single Chainmentioning

confidence: 99%

See 1 more Smart Citation

Mini-review: Synthetic methods for the production of cationic sugar-based surfactants

Jesus

Alves²,

Fiuza³

et al. 2021

Journal of Molecular Liquids

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“…Nima et al synthesized a cationic sugar-based surfactant [ N , N , N -trimethyl-2-oxo-2-(((2 R ,3 S ,4 S ,5 R )-3,4,5-trihydroxy-6-(tetradecyloxy)tetrahydro-2 H -pyran-2yl)methoxy)ethan-1-aminiumiodide, and with the help of a computational study, the size, shape, and aggregation number of the micelle were evaluated using the DFT (B3LYP/6-311G) approach. 69 …”

Section: Surfactant–surfactant Interactionsmentioning

confidence: 99%

A Review on Interactions between Amino Acids and Surfactants as Well as Their Impact on Corrosion Inhibition

Muhammad

Singh

et al. 2022

ACS Omega

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Amino acid−surfactant interactions are central to numerous studies because of their increased effectiveness in chemical, biological, household and industrial use. This review will focus on the impact and effect of the physicochemical properties, temperature, pH, and surfactant chain length of the amino acid for detailed exploration of amino acids and surfactants in aqueous medium. The impact of cosolvent on self-aggregation, critical micelle concentration (CMC), and binding affinity with other biomolecules, as well as amino acid−surfactant interactions, are the epicenters. The results show that increasing the temperature causes negative enthalpy for ionic surfactants and micellization, implying that micellization and amino acids are thermodynamically spontaneous and exothermic, accompanied by positive entropy. As these physicochemical studies are additive, the amino acid and ionic surfactant interactions provide clues on protein unfolding and denaturation under different media, which further changes with a change in physiological conditions like pH, cosolvent, chain length, and temperature. On varying the pH, the net charge of the amino acid also changes and, subsequently, the binding efficiency of the amino acids to the surfactants. The presence of cosolvent causes a lowering in the hydrophobic chain, which changes the surfactant's CMC. At a reduced CMC, the hydrophobic characteristic of amino acid−surfactant associations is amplified, leading to rapid denaturation of proteins that act as propulsion under the influence of extended chain surfactants. Amino acids are one of the most intriguing classes of chemicals that produce high inhibitory efficacy. Amino acids are also a component of proteins and therefore, found in a significant part of the human body, further making them a promising candidate as corrosion inhibitors. In this review article, authors have also focused on the collection and investigation for application of amino acid−surfactant interactions in corrosion inhibition. Various predictive studies/in silico studies are also reported by many research groups, such as density functional theory (DFT) calculations and molecular dynamics simulations to obtain tentative electronic, structural, and physiochemical characteristics like energies of the highest occupied molecular orbitals and lowest unoccupied molecular orbitals, binding energy, Gibb's free energy, electronegativity, polarizability, and entropy. In silico studies are helpful for the mechanism predictions of the process occurring on metal surfaces.

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“…In the past few years, there has been an increase in sugar-based surfactant production due to their green character, good biodegradability, low toxicity, and dermatologically compatible properties. − Additionally, this novel class of products is more advantageous, since they are derived from natural and renewable sources. In a sugar-based surfactant, a sugar molecule represents the hydrophilic moiety, while another hydrophobic molecule represents the hydrophobic moiety.…”

Section: Introductionmentioning

confidence: 99%

Efficient Demulsification of Crude Oil Emulsion Using Novel Sugar-based Surfactant

Abdullah,

Al-Lohedan,

Faqihi

et al. 2024

ACS Omega

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This study aimed to synthesize ecofriendly and low-cost surfactant-based sugar, HA-ST, under mild conditions and a short route via an opening ring of hexadecylsuccinic anhydride (HA) using starch (ST). HA-ST's chemical structure, thermal behavior, and surface activity were evaluated using Fourier Transform Infrared (FTIR) spectroscopy, thermogravimetric analysis, and a pendant drop technique. The results indicated HA-ST formation, thermal stability, and surface activity. HA-ST's green character, low cost, and surface activity recommended its use as a demulsifier for crude oil emulsions at different affecting parameters such as temperature, seawater ratio (SR), demulsifier concentration, demulsification time (DT), and pH. HA-ST demulsification efficiency (DE) was evaluated and compared with a commercial demulsifier (CD). The results showed improved HA-ST's DE with rising temperature, SR, demulsifier concentration, DT, and pH. The DE of HAST reached 100% at 50% of SR and 250 ppm of demulsifier concentration; the same results were obtained using CD. In contrast, HA-ST gave relatively lower DE at low SR (10%) with a value of 70% than the obtained using CD with a value of 75%. The green character, low cost, and DE of HA-ST make it suitable for demulsifying crude oil emulsions, especially those containing more than 30% seawater, compared with CD, which commonly contains two or more traditional surfactants.

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Synthesis of an ionic sugar-amino acid based surfactant in aqueous media

Cited by 4 publications

References 21 publications

Mini-review: Synthetic methods for the production of cationic sugar-based surfactants

Mini-review: Synthetic methods for the production of cationic sugar-based surfactants

A Review on Interactions between Amino Acids and Surfactants as Well as Their Impact on Corrosion Inhibition

Efficient Demulsification of Crude Oil Emulsion Using Novel Sugar-based Surfactant

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