Microwave‐Assisted Synthesis and Characterization of Stearic Acid Sucrose Ester: A Bio‐Based Surfactant

Abstract

Sugar esters of fatty acids are bio‐based surfactants that were synthesized by transesterification of table sugar (sucrose) with stearic acid methyl ester (SAME) in high yield and purity using an optimized microwave‐assisted method. The maximum surfactant product yield of 88.2% was obtained by combining reactants with potassium methoxide and irradiating the mixture with microwaves to achieve an ideal reaction temperature of 132 °C over 21 min. The synthetic procedure described herein minimized undesirable sugar pyrolysis as evidenced by retention of white color characteristic of a pure bio‐based surfactant product. The experiment implemented Box–Behnken design for response surface methodology to refine reaction parameters for optimal product yield. The following parameters were augmented: the irradiation time, the mole ratio of catalyst to sucrose, and temperature.

Microwave‐assisted low‐cost synthesis of sucrose‐soya ester from vegetable oil refinery by‐product and its application in toothpaste formulation for oral hygiene

“…SE contains no sulfate and phosphate group and hence they are low toxic and completely biodegradable (Gumel et al, 2011; Jadhav & Pratap, 2017). SE can be designed to obtain desired hydrophilic–lipophilic balance (HLB) value by changing fatty acid/FAME composition (Benito et al, 2010; Kondamudi & McDougal, 2019; Nakayama et al, 2015; Okamoto et al, 2011; van Kempen et al, 2014).…”

“…The conventional base catalyzed transesterification between SAFAME and sucrose for SE synthesis requires use of mutual solvents like pyridine, DMSO, DMF, and so forth to solubilize both polar and non‐polar reactants and heating under reflux conditions (Chortyk et al, 1996; Osipow et al, 1956; Therisod & Klibanov, 1986). Various techniques reported in the literature include microwave‐assisted (Kondamudi & McDougal, 2019), incubator shaker (Jadhav & Pratap, 2017), six‐station assembly (Deshpande et al, 2013), ultrasound (Huang et al, 2010), without solvent using sand mill (Chen et al, 2019; Gutiérrez et al, 2018), and so forth. The reported methods of SE synthesis based on use of supercritical CO 2 /enzyme catalyst/ionic liquid media or pyridine as catalyst are either low yielding, hazardous or necessitates prolonged reaction time (Ganske & Bornscheuer, 2005; Jadhav & Pratap, 2017; Osipow et al, 1956; Sabeder et al, 2006).…”

Solvent-Free Synthesis of High-Purity Sucrose Fatty Acid Monoesters and a Comparison of Their Properties with Those of Their Commercial Counterparts

“…However, due to the immiscibility of the starting materials required for synthetic production, solvent-free methods frequently suffer from long reaction times, poor yields, and the formation of impure products . Potential solutions to these deficiencies have been reported and include employing sand-milling pretreatment, co-melting, ultrasonic irradiation, heterogeneous base catalysis, and the addition of surfactants. − Although such modifications have improved the yields of the target SEs, to the best of our knowledge, no protocol that can simultaneously generate sucrose monoesters in high purity (∼70%) and practically useful yields (∼50%) has been reported. The work we report here addresses this deficiency.…”

Fatty Acid Evaluation of Seeds and Nuts by Spectroscopy and Chromatography

“…Fatty acid methyl esters needed by the industry are linolenate (ω-3), linoleate (ω-6) [5], oleate (ω-9) [6], and stearate [6][7][8]. Stearic acid or stearate is an SFA found in palm oil and sunflower [6,9], Nymphaea pubescens seeds [10], Ocimum basilicum [5], candlenut [11,12], sesame [13], Cactus opuntia dillenii [14], sacha inchi [15] and almond seeds [16].…”