Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans

Journal Article · Wed Oct 19 00:00:00 EDT 2016 · ACS Central Science

DOI:https://doi.org/10.1021/acscentsci.6b00208· OSTI ID:1329339

Park, Dae Sung ^[1]; Joseph, Kristeen E. ^[1]; Koehle, Maura ^[2]; Krumm, Christoph ^[3]; Ren, Limin ^[1]; Damen, Jonathan N. ^[4]; Shete, Meera H. ^[4]; Lee, Han Seung ^[4]; Zuo, Xiaobing ^[5]; Lee, Byeongdu ^[5]; Fan, Wei ^[6]; Vlachos, Dionisios G. ^[2]; Lobo, Raul F. ^[2]; Tsapatsis, Michael ^[1]; Dauenhauer, Paul J. ^[1]

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1. Department of Chemical Engineering and Materials Science, University of Minnesota, Minneapolis, Minnesota 55455, United States, Catalysis Center for Energy Innovation, Energy Frontier Research Center, U.S. Department of Energy, Newark, Delaware 19716, United States
2. Department of Chemical Engineering, University of Delaware, Newark, Delaware 19716, United States, Catalysis Center for Energy Innovation, Energy Frontier Research Center, U.S. Department of Energy, Newark, Delaware 19716, United States
3. Department of Chemical Engineering and Materials Science, University of Minnesota, Minneapolis, Minnesota 55455, United States, Sironix Renewables, Minneapolis, Minnesota 55455, United States
4. Department of Chemical Engineering and Materials Science, University of Minnesota, Minneapolis, Minnesota 55455, United States
5. X-ray Science Division, Argonne National Laboratory, Lemont, Illinois 60439, United States
6. Department of Chemical Engineering, University of Massachusetts Amherst, Amherst, Massachusetts 01003, United States, Catalysis Center for Energy Innovation, Energy Frontier Research Center, U.S. Department of Energy, Newark, Delaware 19716, United States

One important advance in fluid surface control was the amphiphilic surfactant composed of coupled molecular structures (i.e., hydrophilic and hydrophobic) to reduce surface tension between two distinct fluid phases. However, implementation of simple surfactants has been hindered by the broad range of applications in water containing alkaline earth metals (i.e., hard water). This disrupts surfactant function and requires extensive use of undesirable and expensive chelating additives. We show that sugar-derived furans can be linked with triglyceride-derived fatty acid chains via Friedel–Crafts acylation within single layer (SPP) zeolite catalysts. Finally, these alkylfuran surfactants independently suppress the effects of hard water while simultaneously permitting broad tunability of size, structure, and function, which can be optimized for superior capability for forming micelles and solubilizing in water.

• Research Organization: Univ. of Minnesota, Minneapolis, MN (United States); Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)
• Sponsoring Organization: USDOE Office of Science (SC), Basic Energy Sciences (BES)
• Grant/Contract Number: SC0001004; AC02-06CH11357
• OSTI ID: 1329339
• Alternate ID(s): OSTI ID: 1334181
• Journal Information: ACS Central Science, Journal Name: ACS Central Science Vol. 2 Journal Issue: 11; ISSN 2374-7943
• Publisher: American Chemical Society
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY