Synthesis and interfacial properties of monoacyl glyceric acids as a new class of green surfactants.
Glyceric acid (GA) is one of the most promising functional hydroxyl acids, and it is abundantly obtained from glycerol by a bioprocess using acetic acid bacteria. In this study, several monoacyl GAs were synthesized by esterification of GA and saturated fatty acyl chlorides (C12, C14, C16, and C18), forming a new class of bio-based surfactants. By the present method, a mixture of two isomers, namely 2-O-acyl and 3-O-acyl GAs, was produced, in which the 2-O-acyl derivatives were obtained as a major product. These isomers were isolated, and their surface-active properties were investigated for the first time. The surface tensions of 2-O-acyl GAs with different chain lengths were determined by the Wilhelmy method. At concentrations below 10(-4) M, the 2-O-acyl GAs exhibited higher surface-active properties compared to commercially available synthetic surfactants. For example, 2-O-lauroyl GA reduced the surface tension of water to around 25 mN/m above the critical micelle concentration (3.0×10(-4) M). In addition, 2-O-acyl derivatives showed higher surface-tension-lowering activity than 3-O-acyl GAs. The monoacyl GAs synthesized herein can potentially be used as "green surfactants."
Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan.
Tokuma
T
Fukuoka
Shintaro
S
Ikeda
Hiroshi
H
Habe
Shun
S
Sato
Hideki
H
Sakai
Masahiko
M
Abe
Dai
D
Kitamoto
Keiji
K
Sakaki
D001709:Biotechnology / Q000379:methods; D004305:Dose-Response Relationship, Drug; D020576:Gluconobacter / Q000378:metabolism; D005988:Glyceric Acids / Q000737:chemistry; D005990:Glycerol / Q000737:chemistry; D055772:Green Chemistry Technology / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008823:Micelles; D008956:Models, Chemical; D050178:Monoglycerides / Q000737:chemistry*; D013499:Surface Properties; D013500:Surface Tension; D013501:Surface-Active Agents / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D005988:Glyceric Acids; D008823:Micelles; D050178:Monoglycerides; D013501:Surface-Active Agents; D014867:Water; C042971:glyceric acid; D005990:Glycerol