Selective Syntheses and Properties of Anionic Surfactants Derived from Isosorbide

Cho, Jung‐Eun; Sim, Dae-Seon; Kim, Young‐Wun; Lim, JongChoo; Jeong, Nakcheol; Kang, Ho‐Cheol

doi:10.1002/jsde.12182

Cited by 14 publications

(10 citation statements)

References 29 publications

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“…Various physicochemical properties such as solubility, foamability, surface tension, and critical micelle concentration (CMC) were determined (Table 3). 24 Since most cleaning formulations are water-based, a high water solubility of the surfactant is desired. 33 The synthesized surfactants with L-Ara and D-GalA contain an alkyl chain length varying from 6 to 12 carbons.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In particular, we found that the tertiary amine surfactants are more soluble in water and display favorable surfactant properties such as foamability, stable foams, and emulsions, lowered surface tension of solutions, and a variable critical micelle concentration. 24,25 Hence, this class of molecules may represent a promising set of biobased surfactants derived from sugar beet pulp.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis and Performance of Biobased Surfactants Prepared by the One-Pot Reductive Amination of l-Arabinose and d-Galacturonic Acid

Jansen,

van Rijbroek,

den Bakker

et al. 2023

ACS Sustainable Chem. Eng.

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Herein, we report a method for the synthesis of biobased surfactants derived from sugar beet pulp (SBP) monosaccharides, L-Ara and D-GalA. The surfactants were prepared via one-pot reductive amination, allowing the introduction of different alkyl chain lengths and methyl modifications. Optimal reaction conditions were established to achieve high yields and easy purification. The synthesized surfactants including the tertiary amines exhibited desirable properties, including solubility, foamability, and reduction of surface tension. Notably, the anionic surfactants derived from D-GalA demonstrated better solubility and foam performance compared to those derived from L-Ara. In addition, these surfactants exhibited surface tension and critical micelle concentration (CMC) comparable to those of the commercial surfactant sodium lauryl ether sulfate (SLES). Furthermore, the biodegradable surfactant GalA1.8 displayed excellent emulsifying properties and low skin irritation potential. On the L-Ara surfactant with a short chain, Ara1.6 has potential as a hydrotrope. These findings suggest that biobased surfactants derived from SBP monosaccharides have promising applications in various industries, including pharmaceuticals, cosmetics, detergents, and chemicals.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Performance of Biobased Surfactants Prepared by the One-Pot Reductive Amination of l-Arabinose and d-Galacturonic Acid

Jansen,

van Rijbroek,

den Bakker

et al. 2023

ACS Sustainable Chem. Eng.

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“…Thus, its monoethers cannot be considered surfactants. Nevertheless, anionic and cationic isosorbide‐derived surfactants have been recently synthetized (Cho et al, 2018; Parikh et al, 2020). Lauric isosorbide monoethers can be converted into molecules with a more balanced hydrophilic–lipophilic affinity.…”

Section: Building Blocks and Chemicals Derived From Carbohydratesmentioning

confidence: 99%

Surfactants produced from carbohydrate derivatives: A review of the biobased building blocks used in their synthesis

Ortiz

Alvarado

Zambrano³

et al. 2022

J Surfact & Detergents

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This work reviews the use of carbohydrates and their derivatives as renewable raw materials in the production of surfactants. Methods to attain state‐of‐the‐art carbohydrate‐derived surfactants are described. This includes surfactants widely used nowadays and others that have not yet transcended beyond the academic field. Given the abundance of hydroxyl groups in carbohydrates and the considerable quantity of different surfactant structures that can be generated during their synthesis, selectively obtaining a target product represents a challenge. Therefore, this work focuses on the platform chemicals available to synthesize biobased surfactants. The first part of the review comprises a brief introduction of simple and complex carbohydrates to better understand their chemistry. Then, a description of the processes to obtain biobased building blocks derived from carbohydrates according to the National Renewable Energy Laboratory (NREL, USA), and their usefulness in synthesizing surfactants is presented. This provides an organized inventory of the knowledge around the synthesis–production of surfactants from carbohydrate derivatives, emphasizing raw materials that could be inserted into the circular bioeconomy concept. Finally, the current industry trends and the potential role of biobased surfactants around new dioxane regulations are discussed.

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“…Recently, Cho et al [ 63 ] have proposed a new method for the synthesis of isosorbide-based sulfonate anionic surfactants, with hexyl, octyl, decyl, and dodecyl side chains, in the presence of KOH and toluene or using lithium hydroxide and alkyl bromide in dimethyl sulfoxide.…”

Section: Bio-based Surfactantsmentioning

confidence: 99%

Synthetic and Bio-Derived Surfactants Versus Microbial Biosurfactants in the Cosmetic Industry: An Overview

Moldes

Rincón-Fontán

López-Prieto

et al. 2021

IJMS

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This article includes an updated review of the classification, uses and side effects of surfactants for their application in the cosmetic, personal care and pharmaceutical industries. Based on their origin and composition, surfactants can be divided into three different categories: (i) synthetic surfactants; (ii) bio-based surfactants; and (iii) microbial biosurfactants. The first group is the most widespread and cost-effective. It is composed of surfactants, which are synthetically produced, using non-renewable sources, with a final structure that is different from the natural components of living cells. The second category comprises surfactants of intermediate biocompatibility, usually produced by chemical synthesis but integrating fats, sugars or amino acids obtained from renewable sources into their structure. Finally, the third group of surfactants, designated as microbial biosurfactants, are considered the most biocompatible and eco-friendly, as they are produced by living cells, mostly bacteria and yeasts, without the intermediation of organic synthesis. Based on the information included in this review it would be interesting for cosmetic, personal care and pharmaceutical industries to consider microbial biosurfactants as a group apart from surfactants, needing specific regulations, as they are less toxic and more biocompatible than chemical surfactants having formulations that are more biocompatible and greener.

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Selective Syntheses and Properties of Anionic Surfactants Derived from Isosorbide

Cited by 14 publications

References 29 publications

Synthesis and Performance of Biobased Surfactants Prepared by the One-Pot Reductive Amination of l-Arabinose and d-Galacturonic Acid

Synthesis and Performance of Biobased Surfactants Prepared by the One-Pot Reductive Amination of l-Arabinose and d-Galacturonic Acid

Surfactants produced from carbohydrate derivatives: A review of the biobased building blocks used in their synthesis

Synthetic and Bio-Derived Surfactants Versus Microbial Biosurfactants in the Cosmetic Industry: An Overview

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