Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol

Koso, Shuichi; Furikado, Ippei; Shimao, Akira; Miyazawa, Tomohisa; Kunimori, Kimio; Tomishige, Keiichi

doi:10.1039/b822942b

Cited by 264 publications

(232 citation statements)

References 17 publications

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“…Tomishige et al [54] proposed a mechanism for the reaction of THF-alcohol to 1,5 pentanediol using Rh-Re catalysts. It involves coordination of the OH group of the substrate to Re and subsequent hydrogenolysis of the C-O bond by the neighboring Rh centre.…”

Section: Detailed Studies Using Bimetallic Rh-re Catalystsmentioning

confidence: 99%

From 5-Hydroxymethylfurfural (HMF) to Polymer Precursors: Catalyst Screening Studies on the Conversion of 1,2,6-hexanetriol to 1,6-hexanediol

et al. 2012

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1,6-hexanediol (1) is an important polymer precursor for the polyester industry. In this paper, exploratory catalyst screening studies on the synthesis of 1 from 1,2,6-hexanetriol (2) are described via two different routes. The latter is available by a two-step procedure from 5-hydroxymethylfurfural (HMF, 3), a promising bio-based platform chemical. In the first approach, the direct catalytic hydrodeoxygenation of 2 to 1 with heterogeneous catalysts and molecular hydrogen was explored. Best results were obtained using a Rh-ReO x /SiO 2 catalyst in water (180°C, 80 bar H 2 , 20 h reaction time), leading to full conversion of 2 and 73 % selectivity to 1, the main byproduct being 1,5-hexanediol (4). In a second approach, 2 was first converted to tetrahydropyran-2-methanol (2-THPM, 5) in quantitative yield using triflic acid as catalyst (125°C, 30 min). Various catalysts were explored for the subsequent ring opening/hydrodeoxygenation of 5 to 1 using a hydrogenation protocol and the best results were obtained with a Rh-ReO x /SiO 2 catalyst, viz. 96 % selectivity to 1 at 26 % conversion (120°C, 80 bar H 2 , 20 h).

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Section: Detailed Studies Using Bimetallic Rh-re Catalystsmentioning

confidence: 99%

From 5-Hydroxymethylfurfural (HMF) to Polymer Precursors: Catalyst Screening Studies on the Conversion of 1,2,6-hexanetriol to 1,6-hexanediol

et al. 2012

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“…Industrially, more than 300,000 metric tons/year of FFald are produced [3]. The hydrogenated product such as furfuryl alcohol (FFalc) and tetrahydrofurfuryl alcohol (THFalc) have been also studied to produce more valuable compounds such as levulinic acid, levulinate ester, and a, diols [4][5][6]. FFald also can be converted into methylfuran (MTF) and methyltetrahydrofuran (MTHF), important compound for gasoline-blended.…”

Section: Introductionmentioning

confidence: 99%

Total Hydrogenation of Biomass-Derived Furfural Over Raney Nickel-Clay Nanocomposite Catalysts

Rodiansono¹,

Hara²,

Shimazu³

2013

Indones. J. Chem.

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“…Total hydrogenation reaction of furfural and HMF g ive s t e t r a h y d r o f u r f u r y l a l c o h o l ( T H FA ) a n d 2,5-bis(hydroxymethyl)tetrahydrofuran (BHTHF), respectively. In addition to the utilization of THFA as solvent, the utilization of THFA and BHTHF as a source of polymer has attracted much attention since a selective hydrogenolysis system of THFA to 1,5-pentanediol was discovered by our group in 2009 12) . We and other research groups have intensively investigated the hydrogenolysis of THFA and BHTHF to α,ω-diol (1,5-pentanediol and 1,6-hexanediol, respectively), which can be used as monomers of polyurethane or polyester resin (Fig.…”

Section: Introductionmentioning

confidence: 99%

Supported Metal Catalysts for Total Hydrogenation of Furfural and 5-Hydroxymethylfurfural

Nakagawa

Tamura

Tomishige

2017

J. Jpn. Petrol. Inst.

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Total hydrogenation of furfural and 5-hydroxymethylfurfural (HMF), both of which are important platform chemicals from biomass, produces tetrahydrofurfuryl alcohol (THFA) and 2,5-bis(hydroxymethyl)tetrahydrofuran (BHTHF), respectively, and these products can be used as solvent or raw material of resin. Ni catalysts can give good yields in these reactions; however the low activity and stability are problems. Supported monometallic Pd and Ru catalysts have been reported to be also active in hydrogenation, although the selectivity for total hydrogenation tends to be lower. Other monometallic catalysts such as Cu and Pt generally have low activity in furan ring hydrogenation of furfuryl alcohol (FOL) and 2,5-bis(hydroxymethyl)furan intermediates. We explored various multicomponent catalysts and found that Ni _ Pd/SiO2, Pd _ Ir/SiO2 and Rh _ Ir _ ReOx/SiO2 give good yield of THFA or BHTHF with much higher activity than the mixture of each component supported on SiO2.

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Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol

Cited by 264 publications

References 17 publications

From 5-Hydroxymethylfurfural (HMF) to Polymer Precursors: Catalyst Screening Studies on the Conversion of 1,2,6-hexanetriol to 1,6-hexanediol

From 5-Hydroxymethylfurfural (HMF) to Polymer Precursors: Catalyst Screening Studies on the Conversion of 1,2,6-hexanetriol to 1,6-hexanediol

Total Hydrogenation of Biomass-Derived Furfural Over Raney Nickel-Clay Nanocomposite Catalysts

Supported Metal Catalysts for Total Hydrogenation of Furfural and 5-Hydroxymethylfurfural

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