Selective Hydrogenation of 5-Vinyl-2-Norbornene to 2-Vinylnorbornane

Shorunov, Sergey V.; Piskunova, Ekaterina S.; Петров, В. А.; Bykov, V. I.; Бермешев, М. В.

doi:10.1134/s0965544118120125

Cited by 13 publications

(8 citation statements)

References 10 publications

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“…All test solutions were prepared immediately before use. The investigated compound 2,2 '—bis (bicycle [2.2.1] heptane) was synthesized by the Diels-Alder reaction from 5-vinyl-2-norbornene and dicyclopentadiene according to [ 14 ] with the subsequent stage of exhaustive hydrogenation of the cycloadduct in methanol on a Pd/C catalyst (1%) with hydrogen (25°C, 20 ATM, 24 h) [ 1 , 6 ].…”

Section: Methodsmentioning

confidence: 99%

“…It is assumed that BBH is comparable with the unsymmetrical dimethylhydrazine (UDMH) in terms of specific impulse efficiency, but can be significantly less toxic to the environment and personnel working with rocketry. For the purpose of this study, BBH which consists of two strained structures made of 14 carbons and 22 hydrogens (Fig 1) was synthesized from 5-vinyl-2-norbornene [4][5][6]. Here we present the data describing the toxicity of BBH, which we had obtained by utilizing bacterial lux-biosensors.…”

Section: Introductionmentioning

confidence: 99%

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Genotoxic effect of 2,2’-bis(bicyclo[2.2.1] heptane) on bacterial cells

et al. 2020

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The toxic effect of strained hydrocarbon 2,2'—bis (bicyclo[2.2.1]heptane) (BBH) was studied using whole-cell bacterial lux-biosensors based on Escherichia coli cells in which luciferase genes are transcriptionally fused with stress-inducible promoters. It was shown that BBH has the genotoxic effect causing bacterial SOS response however no alkylating effect has been revealed. In addition to DNA damage, there is an oxidative effect causing the response of OxyR/S and SoxR/S regulons. The most sensitive to BBH lux-biosensor was E . coli pSoxS-lux which reacts to the appearance of superoxide anion radicals in the cell. It is assumed that the oxidation of BBH leads to the generation of reactive oxygen species, which provide the main contribution to the genotoxicity of this substance.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Genotoxic effect of 2,2’-bis(bicyclo[2.2.1] heptane) on bacterial cells

et al. 2020

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“…Modern aerospace vehicles have a limited fuel tank capacity, fly long distances without refueling, and operate at high altitudes at extremely low temperatures. The modernized flying vehicles have accordingly changed the requirements for fuel properties, which have a key influence on an aircraft's flight performance [1][2][3][4][5][6][7]. The most important fuel properties are heating value, density, low freezing point, and viscosity.…”

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confidence: 99%

Novel Strained Alicyclic Hydrocarbons Based on 5-Methylene-2-norbornene

et al. 2021

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The paper describes the synthesis of novel strained hydrocarbons based on a diene of the norbornene series, namely 5-methylene-2-norbornene, using catalytic cyclopropanation with diazomethane. The study demonstrated the possibility of selective cyclopropanation solely along the endocyclic double bond. The physicochemical properties of the hydrocarbons were investigated systematically. These hydrocarbons were shown to have an advantageous combination of high density, low freezing point, and high energy density value. The study’s findings indicate that the compounds synthesized are promising as a component of high-energy-density fuels for modern jet engines.

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“…Selective or total hydrogenation of C�C on the main chain/five-membered ring can be realized respectively by changing the catalyst composition or reaction conditions. 130 Lenhardt et al 131 used diimide to catalyze the hydrogenation of R-PDCPD at 75 °C, and the total HD reached 97% after 3 days of reaction. The oxygen content of HR-PDCPD was only 4.6%, much less than that before hydrogenation (16.3%).…”

Section: Dicyclopentadiene (Dcpd)mentioning

confidence: 99%

“…The ROMP polymerization product of DCPD contains CC double bonds on both the main chain and the five-membered ring. Selective or total hydrogenation of CC on the main chain/five-membered ring can be realized respectively by changing the catalyst composition or reaction conditions . Lenhardt et al .…”

Section: Catalytic Hydrogenation Of Unsaturated Polymersmentioning

confidence: 99%

Advances in the Catalytic Hydrogenation and Properties of Unsaturated Polymers

Yan

Cao

2023

Macromolecules

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Polymer reaction and performance improvement are one of the important contents in the field of polymer materials science and engineering, in which polymer catalytic hydrogenation is an important part of polymer reaction. We reviewed the research achievements on polymer hydrogenation over the past 70 years and studied the mechanism of the hydrogenation reaction from the aspects of performance changes before and after polymer hydrogenation, the catalyst preparation/structure−activity relationship, and polymer hydrogenation kinetics. We pointed out the difficulty in separation and unsatisfactory high-temperature adaptability of traditional homogeneous catalysts and first proposed four effects affecting traditional heterogeneous polymer hydrogenation: scale effect, conformation effect, viscosity effect, and adhesion effect. Based on the structure−activity relationship of polymers, we put forward the application direction of hydrogenated polymers at present. We found that using a new kind of nanometal catalyst (Pd/CNTs@FN) as hydrogenation catalyst can effectively reduce or eliminate the negative effects of these four effects on the polymer hydrogenation reaction, and it is easy to separate from the reaction system. The addition of CNTs can effectively increase the specific surface area of the catalyst and strengthen the interaction between reactants and catalyst. Subsequent research should focus on designing the multiscale structure and improving low-temperature activity of the catalyst, reducing process cost, and using green and efficient separation methods to eliminate adverse effects, create a green and efficient polymer reaction system, accelerate the industrialization of polymer hydrogenation process, and provide theoretical guidance for the research and development of new polymer materials.

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Selective Hydrogenation of 5-Vinyl-2-Norbornene to 2-Vinylnorbornane

Cited by 13 publications

References 10 publications

Genotoxic effect of 2,2’-bis(bicyclo[2.2.1] heptane) on bacterial cells

Genotoxic effect of 2,2’-bis(bicyclo[2.2.1] heptane) on bacterial cells

Novel Strained Alicyclic Hydrocarbons Based on 5-Methylene-2-norbornene

Advances in the Catalytic Hydrogenation and Properties of Unsaturated Polymers

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