The Preparation of Acetopropyl Alcohol and 1,4-Pentanediol from Methylfuran²

Selective Conversion of 2-Methylfuran to 1,4-Pentanediol Catalyzed by Bimetallic Ni-Sn Alloy

“…However, at 100% conversion of 2-MeF, 1,4-PeD yield decreased significantly to 33% while 2-MeTHF yield increased almost twice (61%) after a reaction time was extended to 19 h (entry 8). These results indicated that over hydrogenation of furan ring to produce 2-MeTHF occurred as it had been reported previously [10]. Therefore, it can be concluded that among the synthesized bimetallic Ni-Sn alloy catalysts, Ni-Sn alloy that consist of Ni3Sn and Ni3Sn2 alloy species are active for the hydrolysis-hydrogenation of 2-MeF to 1,4-PeD.…”

“…The kinetic profiles of catalyitic reaction of 2-MeTF over supported Ni-Sn(3.0)/AlOH alloy catalyst are shown in Figure 7. It can be observed that 2-MeTF conversion increased gradually as a function of reaction time and achieved after a reaction time of 12 h. At earlier time, the products were dominated by 2H2MeTHF with maximum 21% in yield (after 2 h) then decreased gradually as the reaction time prolonged to reach almost constant after reaction time was extended up to 16 h. Meanwhile the amount of 2-MeTHF and 1,4-PeD was almost equal indicating the hydrogenation and hydrolysis of double bond of furang ring occurred in parallel as indicated in the previous reports [10,14,[39][40][41][42]. As the reaction times were prolonged, yield 1,4-PeD also increased smoothly to reach maximum 64% in yield after 12 h and then gradually decreased after a reaction time of 14 h. On the other hand, yield of 2-MeTHF increased gradually after the reaction time was extended up to 16 h.…”

“…Interestingly, over aluminium hydroxide (AlOH) and -Al2O3 supported Ni-Sn(3.0) alloy catalysts, high yields of 1,4-PeD (64% and 51%, respectively) were achieved (entries 10 and 11). To the best of our knowledge, these results are the highest yield of 1,4-PeD from catalytic conversion of 2-MeF without the addition of formic acid or acetic acid glacial as it had been reported previously [10,39]. It can be also observed that aluminium hydroxide (AlOH) and -Al2O3 supported Ni-Sn(3.0) catalysts not only enhanced the yield of 1,4-PeD but also reduced the amount of undesired product of 2H2MeTHF.…”

“…By changing the reaction period to 8 h under the similar reaction conditions, 36% yield of 2-MeTHF and 62% yield 1,4-PeD were obtained. They proposed that 1,4-PeD was formed through hydrolysishydrogenation of furan ring in the form of either an open-chain (5-hydroxy-2-pentanone, 5H2PeO) or cyclic structure (2-methyl-2hydroxy tetrahydromethylfuran, 2H2MeTHF) intermediates [10,11]. However, the addition of homogeneous acidic materials (e.g.…”

Ring–Chain Tautomerism of Hydroxyketones

“…The compound was prepared by the reported method (14) and was a colorless liquid boiling at 115-116' (lit. 114.5" (14) …”