Derivatives of γ-Valerolactone, 1,4-Pentanediol and 1,4-Di-(β-cyanoethoxy)-pentane<sup>1</sup>

Christian, Robert; Brown, Horace D.; Hixon, R. M.

doi:10.1021/ja01200a036

Cited by 115 publications

(79 citation statements)

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“…Although the hydrogenation of several lactones to the corresponding diols has been reported [26], only a few heterogeneous catalytic systems are known to convert GVL to 1,4-pentanediol [27] and/or 2-Me-THF. We have found a homogeneous catalytic system that can convert GVL (12.6 mmol) in high yield to 2-Me-THF using Ru(acac) 3 (0.03 mmol) with PBu 3 (1 mmol) and NH 4 PF 6 (0.527 mmol) as co-catalyst under 1,200 psi H 2 at 200°C for 1-2 days.…”

Section: Resultsmentioning

confidence: 99%

Integration of Homogeneous and Heterogeneous Catalytic Processes for a Multi-step Conversion of Biomass: From Sucrose to Levulinic Acid, γ-Valerolactone, 1,4-Pentanediol, 2-Methyl-tetrahydrofuran, and Alkanes

et al. 2008

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The multi-step conversion of sucrose to various C 5 -oxygenates and alkanes was achieved by integrating various homogeneous and heterogeneous catalytic systems. We have confirmed that the dehydration of sucrose to levulinic and formic acids is currently limited to about 30-40% in the presence of H 2 SO 4 , HCl, or Nafion NR50 in water. Performing the dehydration in the presence of a P(m-C 6 H 4 SO 3 Na) 3 modified ruthenium catalyst under hydrogen resulted in the in situ conversion of levulinic acid to c-valerolactone (GVL). Levulinic acid can be hydrogenated to GVL quantitatively by using P(m-C 6 H 4 SO 3 Na) 3 modified ruthenium catalyst in water or Ru(acac) 3 /PBu 3 / NH 4 PF 6 catalyst in neat levulinic acid. Formic acid can be used for the transfer hydrogenation of levulinic acid in water in the presence of [(g 6 -C 6 Me 6 )Ru(bpy)(H 2 O)][SO 4 ] resulting in GVL and 1,4-pentanediol. The hydrogenation of levulinic acid or GVL can be performed to yield 1,4-pentanediol and/or 2-methyl-tetrahydrofuran (2-Me-THF). The hydrogenolysis of 2-Me-THF in the presence of Pt(acac) 2 in CF 3 SO 3 H resulted in a mixture of alkanes. We have thus demonstrated that the conversion of carbohydrates to various C 5 -oxygenates and even to alkanes can be achieved by selecting the proper catalysts and conditions, which could provide a renewable platform for the chemical industry.

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Section: Resultsmentioning

confidence: 99%

Integration of Homogeneous and Heterogeneous Catalytic Processes for a Multi-step Conversion of Biomass: From Sucrose to Levulinic Acid, γ-Valerolactone, 1,4-Pentanediol, 2-Methyl-tetrahydrofuran, and Alkanes

et al. 2008

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“…[1,[9][10][11] Already in 1909, the hydrogenation of LA to GVL was reported by Sabatier and Mailhe [12] using a Raneynickel catalyst in gas phase at 250 °C. Also Christian et al [13] used a Raney-nickel catalyst at 220 °C for the hydrogenation of LA to GVL (GVL yields of 94 %) and Schütte and Thomas [14] investigated the GVL synthesis using platinum oxide as catalyst and diethyl ether as solvent (GVL yields of 87 %). Since 2000, the hydrogenation of LA to GVL has received renewed attention using supported Ru, Pd and Pt based catalysts in both continuous and discontinuous reaction modes at reaction temperatures between 130 and 220 °C and hydrogen pressures up to 55 bar.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of γ-valerolactone by hydrogenation of levulinic acid over supported nickel catalysts

Hengst

Schubert

Carvalho

et al. 2015

Applied Catalysis A: General

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“…The reported efforts regarding the synthesis of 2-MTHF go as far back as the 1940s, with the study of Christian et al [98] who demonstrated the use of a Cu-Cr catalyst for the hydrogenation of levulinic acid at 573 K and 200 atm of H 2 , with a low amount of 2-MTHF (4.5% yield) as a by-product. A similar yield was achieved by Yan et al [99], who used a noble-free Cu-Fe catalyst for the hydrogenation of levulinic acid, achieving a 2-MTHF yield of 3.5%.…”

Section: -Methyltetrahydrofuranmentioning

confidence: 99%

Recent Trends in the Production, Combustion and Modeling of Furan-Based Fuels

Eldeeb

Akih-Kumgeh

2018

Energies

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Abstract:There is growing interest in the use of furans, a class of alternative fuels derived from biomass, as transportation fuels. This paper reviews recent progress in the characterization of its combustion properties. It reviews their production processes, theoretical kinetic explorations and fundamental combustion properties. The theoretical efforts are focused on the mechanistic pathways for furan decomposition and oxidation, as well as the development of detailed chemical kinetic models. The experiments reviewed are mostly concerned with the temporal evolutions of homogeneous reactors and the propagation of laminar flames. The main thrust in homogeneous reactors is to determine global chemical time scales such as ignition delay times. Some studies have adopted a comparative approach to bring out reactivity differences. Chemical kinetic models with varying degrees of predictive success have been established. Experiments have revealed the relative behavior of their combustion. The growing body of literature in this area of combustion chemistry of alternative fuels shows a great potential for these fuels in terms of sustainable production and engine performance. However, these studies raise further questions regarding the chemical interactions of furans with other hydrocarbons. There are also open questions about the toxicity of the byproducts of combustion.

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Derivatives of γ-Valerolactone, 1,4-Pentanediol and 1,4-Di-(β-cyanoethoxy)-pentane¹

Abstract: with an amount of ether insufficient to dissolve the entire fraction and from the insoluble part the diol was recovered. The ether solution was concentrated and after discarding the first crop of crystalline material a second crop, decomposing at 139-140°, analyzed for a mono-tosyl ester.

Cited by 115 publications

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Integration of Homogeneous and Heterogeneous Catalytic Processes for a Multi-step Conversion of Biomass: From Sucrose to Levulinic Acid, γ-Valerolactone, 1,4-Pentanediol, 2-Methyl-tetrahydrofuran, and Alkanes

Integration of Homogeneous and Heterogeneous Catalytic Processes for a Multi-step Conversion of Biomass: From Sucrose to Levulinic Acid, γ-Valerolactone, 1,4-Pentanediol, 2-Methyl-tetrahydrofuran, and Alkanes

Synthesis of γ-valerolactone by hydrogenation of levulinic acid over supported nickel catalysts

Recent Trends in the Production, Combustion and Modeling of Furan-Based Fuels

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Derivatives of γ-Valerolactone, 1,4-Pentanediol and 1,4-Di-(β-cyanoethoxy)-pentane1

Cited by 115 publications

References 0 publications

Integration of Homogeneous and Heterogeneous Catalytic Processes for a Multi-step Conversion of Biomass: From Sucrose to Levulinic Acid, γ-Valerolactone, 1,4-Pentanediol, 2-Methyl-tetrahydrofuran, and Alkanes

Integration of Homogeneous and Heterogeneous Catalytic Processes for a Multi-step Conversion of Biomass: From Sucrose to Levulinic Acid, γ-Valerolactone, 1,4-Pentanediol, 2-Methyl-tetrahydrofuran, and Alkanes

Synthesis of γ-valerolactone by hydrogenation of levulinic acid over supported nickel catalysts

Recent Trends in the Production, Combustion and Modeling of Furan-Based Fuels

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Derivatives of γ-Valerolactone, 1,4-Pentanediol and 1,4-Di-(β-cyanoethoxy)-pentane¹