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

Abstract

An important advance in fluid surface control was the amphiphilic surfactant comprised 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), which disrupt surfactant function and require extensive use of undesirable and expensive chelating additives. Here 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. 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:
; ; ; ; ; ; ; ; ; ; ; ; ; ;
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1375919
DOE Contract Number:  
AC02-06CH11357
Resource Type:
Journal 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)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

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., 2016. 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. Wed . "Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans". United States. doi:10.1021/acscentsci.6b00208.
@article{osti_1375919,
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 = {An important advance in fluid surface control was the amphiphilic surfactant comprised 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), which disrupt surfactant function and require extensive use of undesirable and expensive chelating additives. Here 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. 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},
issn = {2374-7943},
number = 11,
volume = 2,
place = {United States},
year = {2016},
month = {11}
}

Works referencing / citing this record:

Catalytic production of renewable lubricant base oils from bio-based 2-alkylfurans and enals
journal, January 2019

  • Liu, Sibao; Saha, Basudeb; Vlachos, Dionisios G.
  • Green Chemistry, Vol. 21, Issue 13
  • DOI: 10.1039/c9gc01044k