1946
DOI: 10.1021/ja01212a085
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Preparation of Dihydropyran, δ-Hydroxyvaleraldehyde and 1,5-Pentanediol from Tetrahydrofurfuryl Alcohol

Abstract: conditions and deposited on the cool walls of the out let tube which was later cut off and weighed. Any unreacted water was condensed along with the generated hydrogen halide in a tfap of the fractionating line at liquid nitrogen temperatures and, after separation from the hydrogen halide at Dry Ice temperature, was weighed. «-Butane was then

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Cited by 109 publications
(71 citation statements)
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“…An interesting point is that the main product in THFA hydrogenolysis over Rh-ReO x /SiO 2 was 1,5-pentanediol, on the other hand, that over Rh/SiO 2 was 1, [33], was not detected at all over Rh-ReO x /SiO 2 . The maximum 77% yield of 1,5-pentanediol was higher than that of the multi-step method with dihydropyran and d-hydroxyvaleraldehyde as intermediates (70%) [34]. In 1,2-PrD hydrogenolysis, 1-and 2-propanols were produced and the former was major over both Rh-ReO x /SiO 2 and Rh/SiO 2 catalysts.…”
Section: Performance and Characterization Of Rh-reo X /Siomentioning
confidence: 86%
“…An interesting point is that the main product in THFA hydrogenolysis over Rh-ReO x /SiO 2 was 1,5-pentanediol, on the other hand, that over Rh/SiO 2 was 1, [33], was not detected at all over Rh-ReO x /SiO 2 . The maximum 77% yield of 1,5-pentanediol was higher than that of the multi-step method with dihydropyran and d-hydroxyvaleraldehyde as intermediates (70%) [34]. In 1,2-PrD hydrogenolysis, 1-and 2-propanols were produced and the former was major over both Rh-ReO x /SiO 2 and Rh/SiO 2 catalysts.…”
Section: Performance and Characterization Of Rh-reo X /Siomentioning
confidence: 86%
“…Therefore, in order to obtain 1,5-PeD selectively, the multi-step method has been reported (4) [25]. This system is composed of three separated steps including dehydration of THFA to dihydropyran, hydration of dihydropyran to δ-hydroxyvaleraldehyde, and hydrogenation of δ-hydroxyvaleraldehyde to 1,5-PeD.…”
Section: Conventional Hydrogenolysis Of Glycerol and Tetrahydrofurfurmentioning
confidence: 99%
“…(18)(19)(20)(21)(22) These types of catalysts are however either not very stable in aqueous acidic environments due to the dissolution of the support or suffer from rapid coking due to strong interactions between the polar substrates and the also polar catalyst surface. Typical heterogeneous hydrogenation and hydrogenolysis catalysts as used in the petrochemical industry, e.g., CuO•CrO 3 , Ni, Pd, Pt, or Ru on various supports and promoters such as C, SiO 2 , Al 2 O 3 , ZnO, TiO 2 , or zeolites have -as early as the 1930's -been adapted for the representative deoxygenations.…”
Section: Known Heterogeneously Catalyzed Deoxygenationsmentioning
confidence: 99%