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Title: Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans

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.
Authors:
 [1] ;  [1] ;  [2] ;  [3] ;  [1] ;  [4] ;  [4] ;  [4] ;  [5] ;  [5] ;  [6] ;  [2] ;  [2] ;  [1] ;  [1]
  1. Univ. of Minnesota, Minneapolis, MN (United States). Dept. of Chemical Engineering; Energy Frontier Research Center, Newark, DE (United States)
  2. Energy Frontier Research Center, Newark, DE (United States); Univ. of Delaware, Newark, DE (United States). Dept. of Chemical Engineering
  3. Univ. of Minnesota, Minneapolis, MN (United States). Dept. of Chemical Engineering; Sironix Renewables, Minneapolis, MN (United States)
  4. Univ. of Minnesota, Minneapolis, MN (United States). Dept. of Chemical Engineering
  5. Argonne National Lab. (ANL), Argonne, IL (United States). X-ray Science Division
  6. Energy Frontier Research Center, Newark, DE (United States); Univ. of Massachusetts, Amherst, MA (United States). Dept. of Chemical Engineering
Publication Date:
Grant/Contract Number:
SC0001004; AC02-06CH11357
Type:
Published Article
Journal Name:
ACS Central Science
Additional Journal Information:
Journal Volume: 2; Journal Issue: 11; Journal ID: ISSN 2374-7943
Publisher:
American Chemical Society (ACS)
Research Org:
Univ. of Minnesota, Minneapolis, MN (United States)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1329339
Alternate Identifier(s):
OSTI ID: 1334181

Park, Dae Sung, Joseph, Kristeen E., Koehle, Maura, Krumm, Christoph, Ren, Limin, Damen, Jonathan N., Shete, Meera H., Lee, Han Seung, Zuo, Xiaobing, Lee, Byeongdu, Fan, Wei, Vlachos, Dionisios G., Lobo, Raul F., Tsapatsis, Michael, and Dauenhauer, Paul J.. Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans. United States: N. p., Web. doi:10.1021/acscentsci.6b00208.
Park, Dae Sung, Joseph, Kristeen E., Koehle, Maura, Krumm, Christoph, Ren, Limin, Damen, Jonathan N., Shete, Meera H., Lee, Han Seung, Zuo, Xiaobing, Lee, Byeongdu, Fan, Wei, Vlachos, Dionisios G., Lobo, Raul F., Tsapatsis, Michael, & Dauenhauer, Paul J.. Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans. United States. doi:10.1021/acscentsci.6b00208.
Park, Dae Sung, Joseph, Kristeen E., Koehle, Maura, Krumm, Christoph, Ren, Limin, Damen, Jonathan N., Shete, Meera H., Lee, Han Seung, Zuo, Xiaobing, Lee, Byeongdu, Fan, Wei, Vlachos, Dionisios G., Lobo, Raul F., Tsapatsis, Michael, and Dauenhauer, Paul J.. 2016. "Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans". United States. doi:10.1021/acscentsci.6b00208.
@article{osti_1329339,
title = {Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans},
author = {Park, Dae Sung and Joseph, Kristeen E. and Koehle, Maura and Krumm, Christoph and Ren, Limin and Damen, Jonathan N. and Shete, Meera H. and Lee, Han Seung and Zuo, Xiaobing and Lee, Byeongdu and Fan, Wei and Vlachos, Dionisios G. and Lobo, Raul F. and Tsapatsis, Michael and Dauenhauer, Paul J.},
abstractNote = {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.},
doi = {10.1021/acscentsci.6b00208},
journal = {ACS Central Science},
number = 11,
volume = 2,
place = {United States},
year = {2016},
month = {10}
}