The Preparation of 1,3- and 1,4-Pentadienes from Furfural

Schniepp, L. E.; Geller, H. H.

doi:10.1021/ja01217a018

Cited by 24 publications

(3 citation statements)

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“…In addition to the crude oil route, the majority of the literature for piperylene production involves processes using thermochemical methods and homogeneous catalysis. Geller and Schniepp observed that pyrolytic decomposition of 1,5-pentanediol diacetate yielded 1,4-pentadiene with 90–96% purity at 848 K . Brookhart and co-workers have reported ∼40% yield to piperylenes via transfer dehydrogenation of pentane using an iridium pincer complex .…”

Section: Introductionmentioning

confidence: 99%

“…15 In addition to the crude oil route, the majority of the literature for piperylene production involves processes using thermochemical methods and homogeneous catalysis. 1,5-pentanediol diacetate yielded 1,4-pentadiene with 90−96% purity at 848 K. 16 Brookhart and co-workers have reported ∼40% yield to piperylenes via transfer dehydrogenation of pentane using an iridium pincer complex. 17 Recently, Goldman and co-workers have reported high yields (∼70%) to piperylenes for the same reaction catalyzed by pincer-ligated iridium complexes.…”

Section: ■ Introductionmentioning

confidence: 99%

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Ring Opening of Biomass-Derived Cyclic Ethers to Dienes over Silica/Alumina

et al. 2017

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We show that cyclic ethers, such 2-methyltetrahydrofuran (2-MTHF), can undergo dehydration to produce pentadienes over SiO2/Al2O3. The catalyst exhibited reversible deactivation due to coke deposition, with the yield to pentadienes decreasing from 68% to 52% at 623 K over 58 h time on stream. A reaction network for 2-MTHF dehydration was proposed on the basis of the results of space time studies. Pentadienes can be produced directly by a concerted hydride shift and dehydration of carbenium intermediates or indirectly through dehydration of pentanal and pentenol. Reaction kinetics studies were performed at temperatures ranging from 573 to 653 K and 2-MTHF partial pressures from 0.21 to 2.51 kPa. The apparent activation energy barrier for 2-MTHF conversion to pentadienes and the reaction rate order for ring opening were determined to be 74 kJ mol–1 and 0.24, respectively, indicating strong interaction between 2-MTHF and the SiO2/Al2O3 surface. Other solid acids such as γ-Al2O3, H-ZSM-5, and Al-Sn-Beta were found to be active for 2-MTHF dehydration to pentadienes. The rate of ring opening decreased in the order 2,5-dimethyltetrahydrofuran > 2-MTHF > tetrahydropyran > tetrahydrofuran. Over SiO2/Al2O3, the dehydration of 2,5-dimethyltetrahydrofuran resulted in 75% yield to hexadiene isomers.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Ring Opening of Biomass-Derived Cyclic Ethers to Dienes over Silica/Alumina

et al. 2017

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“…All of these factors inspire wide interest to study the production of 1,3-pentadiene [93][94][95]. From the view of sustainable development, many efforts have been made to develop alternative technologies for producing 1,3-pentadiene based on biomass-derived feedstocks [96][97][98][99]. Recently, Sun et al [100] developed a novel two-step synthetic approach using xylitol as a resource ( Figure 6).…”

Section: Synthesis Of Isoprenementioning

confidence: 99%

Synthesis of 1,3-Butadiene and Its 2-Substituted Monomers for Synthetic Rubbers

Liu

et al. 2019

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Synthetic rubbers fabricated from 1,3-butadiene (BD) and its substituted monomers have been extensively used in tires, toughened plastics, and many other products owing to the easy polymerization/copolymerization of these monomers and the high stability of the resulting material in manufacturing operations and large-scale productions. The need for synthetic rubbers with increased environmental friendliness or endurance in harsh environments has motivated remarkable progress in the synthesis of BD and its substituted monomers in recent years. We review these developments with an emphasis on the reactive routes, the products, and the synthetic strategies with a scaling potential. We present reagents that are primarily from bio-derivatives, including ethanol, C4 alcohols, unsaturated alcohols, and tetrahydrofuran; the major products of BD and isoprene; and the by-products, activities, and selectivity of the reaction. Different catalyst systems are also compared. Further, substituted monomers with rigid, polar, or sterically repulsive groups, the purpose of which is to enhance thermal, mechanical, and interface properties, are also exhaustively reviewed. The synthetic strategies using BD and its substituted monomers have great potential to satisfy the increasing demand for better-performing synthetic rubbers at the laboratory scale; the laboratory-scale results are promising, but a big gap still exists between current progress and large scalability.

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1,4‐Pentadiene

et al. 2003

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1,4‐Pentadiene reactant: 658 g. (645 ml., 3.5 moles) of 1,5‐pentanediol diacetate product: 1,4‐pentadiene reactant: 200 g. (201 ml.) of redistilled paraldehyde intermediate: α‐chloroethyl ethyl ether intermediate: α,β‐dibromoethyl ethyl ether reactant: 400 g. (287 ml., 3.31 moles) of allyl bromide reactant: allylmagnesium bromide intermediate: α‐allyl‐β‐bromoethyl ethyl ether reactant: 76.5 g. (82 ml., 1 mole) of allyl chloride reactant: allylmagnesium chloride

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The Preparation of 1,3- and 1,4-Pentadienes from Furfural

Cited by 24 publications

References 0 publications

Ring Opening of Biomass-Derived Cyclic Ethers to Dienes over Silica/Alumina

Ring Opening of Biomass-Derived Cyclic Ethers to Dienes over Silica/Alumina

Synthesis of 1,3-Butadiene and Its 2-Substituted Monomers for Synthetic Rubbers

1,4‐Pentadiene

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