Cyclopentadienyl and pentamethylcyclopentadienyl ruthenium complexes as catalysts for the total deoxygenation of 1,2-hexanediol and glycerol

Thibault, Michelle E.; DiMondo, Domenico; Jennings, Michael C.; Abdelnur, Patrícia Verardi; Eberlin, Marcos N.; Schlaf, Marcel

doi:10.1039/c0gc00255k

Cited by 36 publications

(37 citation statements)

References 44 publications

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“…Also trans-2-penten-1-ol was poorly transformed (30-52%), the pivotal product being 1-pentanol, together with minor amounts of 2-pentenal (up to 8%) and of the corresponding (22,0,9) 45 (36,0,8) experiments. Conversions of cis-2-penten-1-ol were definitely larger than those of the trans-isomer (between 39% and 100%) and with 1-pentanol and pentane and/or pentene as the only products detected, with yields in 1-pentanol as high as 75%.…”

Section: Platinum Catalystsmentioning

confidence: 99%

“…1,2 At present, for one of the most promising derivative, i.e. [7][8][9] In general, the hydrogenation reactions have a crucial role in the preparation of required products for biorefinery and for the flavor, fragrance and pharmaceutical industries, [10][11][12][13][14][15] which are obtained from highly oxygenated biomasses by lowering their O/H ratio. [3][4][5] At the contrary, a useful building block for chemical and pharmaceutical processes, 1-propanol, 6 could be obtained by hydrogenation of 2-propen-1-ol, which, in turn, can be produced by deoxydehydration of glycerol, a by-product of biodiesel production, available in large amounts and at relatively low costs.…”

Section: Introductionmentioning

confidence: 99%

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Hydrogenation of allyl alcohols catalyzed by aqueous palladium and platinum nanoparticles

et al. 2015

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A series of Pd and Pt nanoparticles (NPs) was prepared starting from the corresponding metal ions and lignosulphonates; NPs were tested as catalysts for allyl alcohols hydrogenation in water at room temperature and pressure. All NPs were active with sharp differences in conversions and selectivites: Pt NPs formed mainly saturated alcohols, whereas Pd NPS were more active, but less selective, forming, in addition to saturated alcohols, also isomeric unsaturated alcohols and aldehydes, both saturated and unsaturated.. Results and DiscussionWe prepared a series of twelve NPs using two metals (Pt and Pd) and six water-soluble lignins: Kraft lignin (KrLig), ammonium lignosulphonate (AmLig), calcium (CaLig) and sodium (NaLig) lignosulphonates and the corresponding lowsugar ones (CaROLig and NaROLig); lignins, in water solution and at 80 °C, acted as both reducing agents for the metal ions, i.e. H 2 PtCl 6 and PdCl 2 , and as stabilizing agents for the formed

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Section: Platinum Catalystsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hydrogenation of allyl alcohols catalyzed by aqueous palladium and platinum nanoparticles

et al. 2015

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“…sulfuric acid) were added to improve catalytic conversions. There are also reports [46][47][48][49][50][51][52] on the use of homogeneous ruthenium catalysts in combination with triflic acid (HOTf) and sulfolane as the solvent for the selective hydrodeoxygenation of a secondary alcohol in the presence of a primary alcohol. For example, Schlaf et al [51] reported the production of 1-propanol from 6 using [{Cp*Ru(CO) 2 While preparing this manuscript, Dumesic et al [44] reported hydrodeoxygenation reactions of various diols and triols using bimetallic Rh-ReO x catalysts on carbon supports.…”

Section: 6-hexanediolmentioning

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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“…Bullock and Fagan found that {[Cp*Ru(CO) 2 ] 2 (-H)} + OTf − is a precursor for the selective hydrogenolysis of 1,2-propanediol to 1-propanol (Scheme 1) [19][20][21]. The total deoxygenation of glycerol and 1,2-hexanediol to saturated hydrocarbons by [LRu(H 2 O) x (diimine)] 2+ and [Cp*Ru(OH 2 )(N N)] + was reported by Schlaf and coworkers [22,23].…”

Section: Introductionmentioning

confidence: 82%

Ruthenium (II) sulfoxides-catalyzed hydrogenolysis of glycols and epoxides

Murru

Nicholas

Srivastava

2012

Journal of Molecular Catalysis A: Chemical

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Cyclopentadienyl and pentamethylcyclopentadienyl ruthenium complexes as catalysts for the total deoxygenation of 1,2-hexanediol and glycerol

Cited by 36 publications

References 44 publications

Hydrogenation of allyl alcohols catalyzed by aqueous palladium and platinum nanoparticles

Hydrogenation of allyl alcohols catalyzed by aqueous palladium and platinum nanoparticles

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

Ruthenium (II) sulfoxides-catalyzed hydrogenolysis of glycols and epoxides

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