Bistetrahydrofurfuryl ether

Prutkov, L. M.; Sanin, I. K.; Kamenskii, I. V.

doi:10.1007/bf00509453

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“…This spectrum is largely in agreement with the one presented by Prutkov et al., except for the area around 1700 cm −1 . In the spectrum presented by Prutkov et al., there is a medium intensity peak at approximately 1700 cm −1 that is absent in our spectrum . Alkene stretching occurs at this frequency, and we suspect, based on the evidence presented by Kirner related to the difficulty of producing alkyl tetrahydrofurfuryl ethers using tetrahydrofurfuryl halides as reagents, that the previously reported synthesis of BTHFE actually produced a mixture of the ether and 2‐methylene tetrahydrofuran.…”

Section: Figuresupporting

confidence: 49%

“…One tetrahydrofurfuryl ether derivative that has remained elusive is bis (tetrahydrofurfuryl) ether (BTHFE). We found one previous report of its synthesis, but this report lacked an in‐depth characterization of the compound, which left some doubt as to the true identity of the reported product …”

Section: Figurementioning

confidence: 93%

“…Previously, it has been reported that BTHFE had been produced by reacting tetrahydrofurfuryl bromide with sodium tetrahydrofurfurylate. In the previously published report of the synthesis, the chief spectroscopic evidence that the authors used to identify the compound was an IR spectrum . The IR spectrum for the BTHFE that we produced is shown in Figure .…”

Section: Figurementioning

confidence: 99%

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Synthesis and Characterization of bis (Tetrahydrofurfuryl) Ether

et al. 2016

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Despite the availability of al arge number of alkyl tetrahydrofurfuryle thers that have aw ide 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,a nd 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 an on-volatile solvent in poly(3,4-propylenedioxythiophene)-baseds upercapacitors. Supercapacitor devices employing solutions of the ionic liquid 1-ethyl-3-methyl-imidizolium bis(trifluoromethylsulfonyl)-imide in BTHFE display similarp erformances to those prepared by using the neat ionic liquid as an electrolyte, although solution-based devicese xhibit asomewhat higherresistance.Ar elativelyl arge number of scientific publications and patents have analyzed, or proposed, the use of alkyl tetrahydrofurfuryl ethers for ad iverse array of applications. In 1930, Kirner synthesized as mall library of alkyl tetrahydrofurfuryl ethers, and analyzed their toxicity in mice and guineap igs. [1] His study demonstrated that this class of ethers exhibit significant anesthetic effects when administered intraperitoneally.K irner also noted that, in larger doses, the compounds were toxic and, even at low doses, they appeared to initiate intestinal necrosis, which often proved fatal for the test animals. The synthetic methods employed by Kirner were very similar to those used by Wissell and To llens when they first synthesized furfuryl ether derivatives in 1892. [2] As ignificant body of published work shows the utility of these compounds as structuralm odifiers in rubbers. Modification of rubber with various alkyl tetrahydrofurfuryl ethers increases the static friction coefficient, and the rubberc an be used in automobile tires. [3] Additionally, these compoundsh ave been proposed as components of heat pumps, [4] paint strippers, [5] and as fuel additives. [6] Therei s clearly ap otentialm arket for these compounds, and there are severalr eportso fm ethods for their synthesis. [1, 7] One tetrahydrofurfuryl ether derivative that hasr emained elusive is bis(tetrahydrofurfuryl) ether (BTHFE). We found one previous report of its synthesis, but this report lacked an in-depth characterization of the compound, which left some doubt as to the true identityoft he reported product. [8] When Kirner attempted to make methyl tetrahydrofurfuryl ether using tetrahydrofurfuryl chloride and methanol as starting materials, he found that the chloride reactedv ery slowly, the reaction only occurred to as light extent, andi th ad the added disadvantageo fp roducinga nu nsaturated tetrahydrofuran derivative, 2-methylene tetrahydrofuran, as abyproduct. [1] Previously,i th as been reported that BTHFE had been produced by reacting tetrahydrofurfuryl bromide with sodium tetrahydrofurfurylate. In the previouslyp ublished report of the synthesis, the chief spectroscopic evidence that th...

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Section: Figuresupporting

confidence: 49%

Section: Figurementioning

confidence: 93%

Section: Figurementioning

confidence: 99%

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