Cargando…

Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether

Despite the availability of a large number of alkyl tetrahydrofurfuryl ethers that have a wide range of applications, pure bis(tetrahydrofurfuryl) ether (BTHFE) has not been previously synthesized. Here, we report the synthesis of BTHFE (consisting of the RR, SS, and meso stereoisomers) at greater t...

Descripción completa

Detalles Bibliográficos
Autores principales: Stenger‐Smith, John D., Baldwin, Lawrence, Chafin, Andrew, Goodman, Paul A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4981047/
https://www.ncbi.nlm.nih.gov/pubmed/27547636
http://dx.doi.org/10.1002/open.201600013
_version_ 1782447559946534912
author Stenger‐Smith, John D.
Baldwin, Lawrence
Chafin, Andrew
Goodman, Paul A.
author_facet Stenger‐Smith, John D.
Baldwin, Lawrence
Chafin, Andrew
Goodman, Paul A.
author_sort Stenger‐Smith, John D.
collection PubMed
description Despite the availability of a large number of alkyl tetrahydrofurfuryl ethers that have a wide range of applications, pure bis(tetrahydrofurfuryl) ether (BTHFE) has not been previously synthesized. Here, we report the synthesis of BTHFE (consisting of the RR, SS, and meso stereoisomers) at greater than 99 % purity from tetrahydrofurfuryl alcohol, using (tetrahydrofuran‐2‐yl)methyl methanesulfonate as an intermediate. Additionally, we demonstrate that BTHFE can be used as a non‐volatile solvent in poly(3,4‐propylenedioxythiophene)‐based supercapacitors. Supercapacitor devices employing solutions of the ionic liquid 1‐ethyl‐3‐methyl‐imidizolium bis(trifluoromethylsulfonyl)imide in BTHFE display similar performances to those prepared by using the neat ionic liquid as an electrolyte, although solution‐based devices exhibit a somewhat higher resistance.
format Online
Article
Text
id pubmed-4981047
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-49810472016-08-19 Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether Stenger‐Smith, John D. Baldwin, Lawrence Chafin, Andrew Goodman, Paul A. ChemistryOpen Communications Despite the availability of a large number of alkyl tetrahydrofurfuryl ethers that have a wide range of applications, pure bis(tetrahydrofurfuryl) ether (BTHFE) has not been previously synthesized. Here, we report the synthesis of BTHFE (consisting of the RR, SS, and meso stereoisomers) at greater than 99 % purity from tetrahydrofurfuryl alcohol, using (tetrahydrofuran‐2‐yl)methyl methanesulfonate as an intermediate. Additionally, we demonstrate that BTHFE can be used as a non‐volatile solvent in poly(3,4‐propylenedioxythiophene)‐based supercapacitors. Supercapacitor devices employing solutions of the ionic liquid 1‐ethyl‐3‐methyl‐imidizolium bis(trifluoromethylsulfonyl)imide in BTHFE display similar performances to those prepared by using the neat ionic liquid as an electrolyte, although solution‐based devices exhibit a somewhat higher resistance. John Wiley and Sons Inc. 2016-05-03 /pmc/articles/PMC4981047/ /pubmed/27547636 http://dx.doi.org/10.1002/open.201600013 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Stenger‐Smith, John D.
Baldwin, Lawrence
Chafin, Andrew
Goodman, Paul A.
Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether
title Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether
title_full Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether
title_fullStr Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether
title_full_unstemmed Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether
title_short Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether
title_sort synthesis and characterization of bis(tetrahydrofurfuryl) ether
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4981047/
https://www.ncbi.nlm.nih.gov/pubmed/27547636
http://dx.doi.org/10.1002/open.201600013
work_keys_str_mv AT stengersmithjohnd synthesisandcharacterizationofbistetrahydrofurfurylether
AT baldwinlawrence synthesisandcharacterizationofbistetrahydrofurfurylether
AT chafinandrew synthesisandcharacterizationofbistetrahydrofurfurylether
AT goodmanpaula synthesisandcharacterizationofbistetrahydrofurfurylether