Trapp mixture: Difference between revisions
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{{Short description|Low-melting mixture of organic solvents}} |
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{{Use dmy dates|date=March 2024}} |
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The '''Trapp mixture''' is a specific [[mixture]] of organic [[solvent]]s that allows [[chemical reaction]]s to take place at very low temperatures.<ref>{{cite journal | |
The '''Trapp mixture''' is a specific [[mixture]] of organic [[solvent]]s that allows [[chemical reaction]]s to take place at very low temperatures.<ref>{{cite journal | url=https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cber.19660990243| author1=G. Köbrich |author2=H. Trapp | journal = [[Chem. Ber.]] | date = February 1966 | volume = 99 | issue = 2 | pages = 680 | doi = 10.1002/cber.19660990243 | title = Darstellung und thermische Stabilität von 1-Chlor-2.2-diaryl-vinyllithium-Verbindungen ('The formation and thermal stability of 1-chloro-2,2-diaryl-vinyl lithium compounds')| accessdate = 10 March 2024}}</ref> It is made up of [[THF]]:[[diethyl ether]]:[[pentane]] in a 4:4:1 ratio which remains liquid down to −110 °C and the same solvents in a 4:1:1 ratio remain a liquid down to −120 °C. This solvent system retains a low viscosity until just before freezing and it allows a lower temperature reaction than pure THF, which melts at −108.4 °C. An illustrative application of Trapp solvent is the preparation of [[vinyllithium]] by [[Organolithium reagent#Lithium–halogen exchange|lithium halogen exchange]] from [[vinyl bromide]] and [[tert-Butyllithium|''tert''-butyllithium]].<ref>{{Cite journal|url=https://onlinelibrary.wiley.com/doi/10.1002/047084289X.rv015.pub2| author1 = Eric K. Eisenhart| author2 = Bernard Bessieres | title= "Vinyllithium" | work = e-EROS Encyclopedia of Reagents for Organic Synthesis| date = 17 September 2007| doi=10.1002/047084289X.rv015.pub2| accessdate = 10 March 2024}}</ref> The low temperatures suppress the reaction of the strongly basic organolithium reagent with the THF. |
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== References == |
== References == |
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[[Category:Solvents]] |
[[Category:Solvents]] |
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Latest revision as of 23:44, 10 March 2024
The Trapp mixture is a specific mixture of organic solvents that allows chemical reactions to take place at very low temperatures.[1] It is made up of THF:diethyl ether:pentane in a 4:4:1 ratio which remains liquid down to −110 °C and the same solvents in a 4:1:1 ratio remain a liquid down to −120 °C. This solvent system retains a low viscosity until just before freezing and it allows a lower temperature reaction than pure THF, which melts at −108.4 °C. An illustrative application of Trapp solvent is the preparation of vinyllithium by lithium halogen exchange from vinyl bromide and tert-butyllithium.[2] The low temperatures suppress the reaction of the strongly basic organolithium reagent with the THF.
References
[edit]- ^ G. Köbrich; H. Trapp (February 1966). "Darstellung und thermische Stabilität von 1-Chlor-2.2-diaryl-vinyllithium-Verbindungen ('The formation and thermal stability of 1-chloro-2,2-diaryl-vinyl lithium compounds')". Chem. Ber. 99 (2): 680. doi:10.1002/cber.19660990243. Retrieved 10 March 2024.
- ^ Eric K. Eisenhart; Bernard Bessieres (17 September 2007). ""Vinyllithium"". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rv015.pub2. Retrieved 10 March 2024.
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