DOI: 10.1002/open.201600076

Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether

Chemistry Division, Code 4F0000D, Research Department Naval Air Warfare Center Weapons Division The Goodman team, from left to right: Andrew Chafin, Paul A. Goodman, Lawrence Baldwin, and John D. Stenger-Smith

Invited for this month’s cover are researchers from the Naval Air Warfare Center Weapons Division (USA). The cover picture shows the elusive symmetric molecule bis(tetrahydrofurfuryl) ether (BTHFE) in the making. For more details, read the full text of the Communication at 10.1002/open.201600013.

In one word, how would you describe your research?

What was the biggest surprise (on the way to the results presented in this paper)?

Diverse. Many topics are of interest to the Navy, and at their core each of them has fundamental aspects that need to be explored and understood. Our focus is on trying to identify the fundamental questions behind the Navy’s needs and then try to answer them.

The biggest surprise that we faced, as noted in the text, is that the intermediate, (tetrahydrofuran-2-yl)methyl methanesulfonate, reacts violently with air, but only when it is at an elevated temperature. At room temperature, it appears to be relatively stable, or at least the reaction is much slower.

What is the most significant result of this study?

Acknowledgement

The true significance of this study is that by using (tetrahydrofuran-2-yl)methyl methanesulfonate in the synthesis of bis(tetrahydrofurfuryl) ether, we demonstrated that this intermediate allows one to synthesize pure tetrahydrofurfuryl ethers with bulkier substituents in a relatively straightforward manner. Bis(tetrahydrofurfuryl) ether, in particular, is interesting because its structure suggests that it may act as a chelating agent for cations, which could be useful in organic synthesis or energystorage applications.

We gratefully acknowledge the NAWCWD Internal Investment Program, Power Systems Initiative for the funding that supported this effort.

What was the biggest challenge (on the way to the results presented in this paper)?

Our biggest challenge was finding out why our initial elemental analyses were slightly out of the calculated range. We sent multiple samples to multiple companies and, while the elemental analyses were close to the predicted values, they didn’t quite fit with our NMR and GC/MS analyses—all indicating at least 99.5% purity. It turns out that the samples picked up a little moisture during the trip to the elemental analysis facility. Once we figured this out and requested that the samples be dried, the elemental analyses matched the predicted values. ChemistryOpen 2016, 5, 269

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Ó 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether.

Invited for this month's cover are researchers from the Naval Air Warfare Center Weapons Division (USA). The cover picture shows the elusive symmetric...
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