Sulfonated surfactants obtained from furfural

Abstract

Furfural obtained from pentose containing biomass such as hemicelluloses is subjected to photooxygenation. The resulting hydroxyfuranone obtained in high yields undergoes acetalization with fatty alcohols. Using NaHSO 3 , surfactants are obtained by addition of a sulfonate group to α,β-unsaturated carboxyl or carbonyl compounds. Addition occurred either at the CvC double bond (6) or at the aldehyde function (7). Compared to conventional surfactants of this type, the resulting compounds possess similar good detergent properties. In the case of compound family 6 and when compared to the corresponding alkylsulfate and alkylsulfonate surfactants, even lower critical micelle concentrations (CMC) are observed. Biodegradation of the new surfactants was determined according to the OECD Test guideline 301 F. Compounds of family 6 are biodegradable. Biodegradation of compounds of family 7 stopped after 10 days.

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

“…Furfural serves as the basis for obtaining multiple value‐added organic compounds that can be upcycled (Figure 23) (Lichtenthaler, 2010b). Gassama et al (2013) obtained 5‐hydroxyfuran‐2(5H)‐one by photooxygenation of furfural that served as a precursor to synthesized sulfonated surfactants. As seen in Figure 24, 5‐hydroxyfuran‐2(5H)‐one is converted into an α,β‐unsaturated alkoxyfuranone, by etherification with fatty alcohol (C 8 , C 10, and C 12 ) (Gassama et al, 2013).…”

“…Gassama et al (2013) obtained 5‐hydroxyfuran‐2(5H)‐one by photooxygenation of furfural that served as a precursor to synthesized sulfonated surfactants. As seen in Figure 24, 5‐hydroxyfuran‐2(5H)‐one is converted into an α,β‐unsaturated alkoxyfuranone, by etherification with fatty alcohol (C 8 , C 10, and C 12 ) (Gassama et al, 2013). Then, α,β‐unsaturated alkoxyfuranone is converted into the respective sulfonate.…”

“…cmc for n = 6, 8 measured at 25°C, cmc for n = 10 measured at 50°C. Adapted from Gassama et al (2013) and Kipshagen et al (2019)…”

Synthesis and Surface Properties of a Novel Sodium 3‐(3‐Alkyloxy‐3‐oxopropoxy)‐3‐oxopropane‐1‐sulfonate at the Air–Water Interface

“…The desired compound was characterized by NMR ( 1 H and 13 C), IR and mass spectroscopy. IR (cm -1 ): 2928, 2958 (aliphatic C-H stretching), 1734 (carbonyl stretching), 1466 (C-H scissoring), 1177 (O-C-O stretching), 721 (C-H rocking); 1 H NMR (300 MHz, CDCl 3 , ppm): d 6.4 (d, 1H; CH 2 =CH-; cis to carbonyl), 6.1 (dd, General Procedure for the Synthesis of Sodium 3-(3-Alkyloxy-3-oxopropoxy)-3-oxopropane-1-sulfonate Sulfonation of 3-(alkyloxy)-3-oxopropyl acrylate was carried out according to the method reported in the literature [10]. Briefly, a solution of 3-(alkyloxy)-3-oxopropyl acrylate in isopropanol was added to an aqueous solution of NaHSO 3 (1.5 mole equivalent) and the resultant reaction mixture was stirred at 50°C for 28 h. After completion, the organic solvent was evaporated using a rotary evaporator and the dried mass was solubilized in 100 mL of methanol and filtered through Whatman filter paper to remove unreacted NaHSO 3 .…”

“…The structures of all the esterified products were established by NMR ( 1 H and 13 C), IR and mass spectral data. Finally, the sulfonation of 3-alkyloxy-3-oxopropyl acrylate was carried out efficiently at the active terminal olefin according to the method reported in the literature [10]. The structures of the sodium 3-(3-alkyloxy-3-oxopropoxy)-3-oxopropane-1-sulfonates were confirmed by HRMS data.…”