Hydrogenolysis of C-O bond over Re-modified Ir catalyst in alkane solvent

nnedy, CA; Macmillan, SN; Mcalduff, MJ; Marangoni, DG; Nakagawa, Y; Mori, K; Chen, K; Amada, Y; Tamura, M; Tomishige, K

HERO ID

4684005

Reference Type

Journal Article

Year

2013

HERO ID 4684005
In Press No
Year 2013
Title Hydrogenolysis of C-O bond over Re-modified Ir catalyst in alkane solvent
Authors nnedy, CA; Macmillan, SN; Mcalduff, MJ; Marangoni, DG; Nakagawa, Y; Mori, K; Chen, K; Amada, Y; Tamura, M; Tomishige, K
Journal Applied Catalysis A: General
Volume 468
Page Numbers 418-425
Abstract Hydrogenolysis of alcohols was carried out using n-heptane solvent and Ir-ReOx/SiO2 catalyst, which has been known to be active in water solvent. Hydrogenolysis of trans-1,2-cyclohexanediol proceeded more smoothly in n-heptane than in water. The maximum yield of cyclohexanol was 74%, and at longer reaction time cyclohexane was selectively formed (>80% yield). Stronger adsorption of substrate on catalyst surface in n-heptane than in water is one of factors in obtaining the good yields. Alkane solvent was also advantageous to water solvent in hydrogenolysis of mono-alcohols. The reaction route via acid-catalyzed dehydration and subsequent hydrogenation is enhanced in alkane solvent. On the other hand, the "direct" hydrogenolysis driven by the hydride-like species is suppressed in alkane solvent, leading lower activity in n-heptane for hydrogenolysis of tetrahydrofurfuryl alcohol or 1,2-hexanediol, which smoothly react over Ir-ReOx/SiO2 catalyst in water. (C) 2013 Elsevier B.V. All rights reserved.
Doi 10.1016/j.apcata.2013.09.021
Wosid WOS:000327804200048
Is Certified Translation No
Dupe Override No
Is Public Yes
Keyword Hydrogenolysis; Alcohol; Solvent effect; Iridium; Rhenium