New Family of Surfactants from Biobased Materials

Abstract

β-C-Glycoside ketone derivatives of glucose, lactose, and maltose were converted to amines via a reductive amination using 5 wt % Rh/Al 2 O 3 in ammoniacal methanol under 34 bar H 2 . The amines were isolated and then were used as the amine in the reductive amination of 2-undecanone that can be prepared from the seed oil of Cuphea. The resulting β-C-glycoside-2-aminoundecanes were characterized by MALDI-TOF mass spectrometry and 2D NMR. The critical micelle concentrations of the products as measured by isothermal calorimetry titration ranged from 1 to 5 mM, and the micelles carry a positive charge as measured by zeta potentials. The β-C-glycoside 2-aminoundecanes have antimicrobial activity against Bacillus subtilis, Pseudomonas aeruginosa, Erwinia amylovora, and Escherichia coli, with the C-glucoside derivative having the greatest activity with a minimum inhibitory concentration of 0.31 mM and a minimum bactericide concentration of 0.62 mM against the Gram positive organisms. Against the Gram negative Erwinia and Escherichia, the MIC is 0.62 mM. This work introduces a new family of sustainable surfactants with potential uses in personal care and cleaning products.

Cuphea as a Source of Fully Crop-Based Plasticizers for Poly(vinyl chloride)

“…This results in 2-undecanone that contains one nonrenewable carbon. 33 This is retained in the conversion to 2-aminoundecane. The three furans are sugar-sourced and are fully renewable.…”

The Genus Cuphea P. Browne as a Source of Biologically Active Phytochemicals for Pharmaceutical Application and Beyond—A Review

“…Cuphea oil can be an ingredient in decorative cosmetics (e.g., lipsticks), body-care products (bath oils and creams) or hair-care cosmetics (lotions) [ 134 ]. Oils with high levels of decanoic acid, due to cross ketonisation reactions with acetic acid, are used in the production of 2-undecanone, which is a well-known aromatic compound and an insect repellent [ 135 ]. Cuphea oils are being investigated as a source of biobased lubricants [ 136 ].…”

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

“…The latter includes additional purification steps that imply higher capital and operational costs and result in a higher cost of goods (Narasimhan et al, 2015; Sebastiani et al, 2021; Yang, 1980). In this context, the higher cost of fatty alcohol ethoxylates opens a window of opportunity for biobased surfactants to be more cost‐competitive and substitute fatty alcohol ethoxylates in household products and biocompatible formulations (Jackson et al, 2021; Kandasamy et al, 2019; Sreenu et al, 2015). Nevertheless, biobased surfactants present a distribution of different substances (due to the nature of fermentation reactions and the variability of feedstocks), making the formulation with such products more challenging (although more environmentally friendly) (Hayes & Smith, 2019).…”

“…Nevertheless, biobased surfactants present a distribution of different substances (due to the nature of fermentation reactions and the variability of feedstocks), making the formulation with such products more challenging (although more environmentally friendly) (Hayes & Smith, 2019). In addition, high selectivity processes to synthesize APGs and N ‐palmitoyl aminoacids surfactants generate byproducts as glycosidic compounds and fatty acids, which are eco‐friendly (Jackson et al, 2021; Sreenu et al, 2015). Life cycle analyses indicate that the biodegradability and sustainability of biobased surfactants (Athaley et al, 2019; Hayes et al, 2019; Shah et al, 2016) is higher compared to that of alcohol ethoxylates.…”