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Usage

Uses

Used in Scientific Research:
Trans-2-Pentene is used as a chemical intermediate for the synthesis of various organic compounds in scientific research. Its unsaturated nature allows for a wide range of chemical reactions, making it a valuable compound for the development of new materials and pharmaceuticals.
Used in Industrial Applications:
In the industry, trans-2-pentene is used as a raw material for the production of polymers and other chemical products. Its reactivity and versatility make it a key component in the synthesis of various industrial chemicals, contributing to the manufacturing of plastics, rubber, and other materials.
Used in Natural Occurrence Studies:
Trans-2-pentene can also be found in nature, and its presence in certain plants and organisms is of interest to researchers studying natural product chemistry. It is used as a reference compound in the identification and analysis of natural compounds, helping to understand the chemical diversity and potential applications of these substances in various fields.

InChI:InChI=1/C5H10/c1-3-5-4-2/h3,5H,4H2,1-2H3/b5-3+

Upstream product

• 64-17-5 ethanol 
• 107-81-3 2-bromopentane 
• 917-58-8 potassium ethoxide 
• 101944-72-3 pentan-2-yl methane sulfonate 
• 22415-74-3 erythro-2,3-dibromopentane 
• 1809-10-5 3-bromopentane 
• 1809-05-8 3-pentyl iodide 
• 109-67-1 1-penten 
• 100910-84-7 (1-ethyl-propyl)-dimethyl-amine oxide 
• 620-11-1 3-pentyl acetate 
• 861310-83-0 2-ethyl-3-bromo-butyric acid 
• 855224-27-0 2-ethyl-3-iodo-butyric acid 
• 98429-20-0 dithiocarbonic acid O-(1-ethyl-propyl ester)-S-methyl ester 
• 1822-71-5 n-pentylsodium 

Downstream Products

• 600-11-3 (2RS,3SR)-2,3-dichloro-pentane 
• 6172-89-0 1-Methyl-butyl-phosphonsaeure-dimethylester 
• 42027-23-6 threo-pentane-2,3-diol 
• 5398-25-4 2,3-dibromo-pentane 
• 13269-52-8 trans-3-Hexene 
• 4050-45-7 trans-2-hexene 
• 674-76-0 (E)-4-methylpent-2-ene 
• 19781-69-2 trans-2-ethyl-3-methyloxirane 
• 13682-99-0 dichloro(n-pentyl)methylsilane 
• 141-05-9 Diethyl maleate 
• 111948-28-8 (E)-2-Hydroxy-3-methyl-1-phenyl-hex-4-en-1-one 
• 89959-74-0 threo(dl)-2,3-bis(tosyloxy)pentane 
• 61131-37-1 (E)-3-Methyl-2-(toluene-4-sulfonylamino)-hex-4-enoic acid butyl ester 

Relevant academic research and scientific papers

Mechanism of alkene isomerization by bifunctional ruthenium catalyst: A theoretical study

The molecular mechanism of the isomerization of 1-pentene to form (E)-2-pentene catalyzed by the bifunctional ruthenium catalyst has been investigated using density functional theory calculations. The reaction is likely to proceed through the following steps: 1) the β-H elimination to generate the ruthenium hydride intermediate; 2) the reductive elimination of the hydride intermediate to generate the nitrogen-protonated allyl intermediate; 3) the transportation of the hydrogen by the dihedral rotation with Ru-P bond acting as axis; 4) the oxidative addition to afford another hydride complex; 5) the reductive elimination of the hydride intermediate to form the C 2-C3 π-coordinated agostic intermediate; 6) the coordination of the nitrogen to the ruthenium center to give the final product. The rate-determining step is the oxidative addition step (the process of the hydrogen moves to ruthenium center from the nitrogen atom) with the free energy of 31.2 kcal/mol in the acetone solvent. And the N-heterocyclic ligand in the catalyst mainly functions in the two aspects: affords an important internal-basic center (nitrogen atom) and works as a transporter of hydrogen. Our results would be helpful for experimentalists to design more effective bifunctional catalysts for isomerization of a variety of heterofunctionalized alkene derivatives.

Designing and synthesis of phosphine derivatives of Ru3(CO)12 – Studies on catalytic isomerization of 1-alkenes

A comparative investigation on the isomerization reactions of 1-alkenes to their corresponding 2-alkenes catalyzed Ru3(CO)12 (1), Ru3(CO)9(PEt3)3 (2) and Ru3(CO)10(dppe) (3), (where dppe = 1,2-bis(diphenylphosphino)ethane) is described. Both the complexes of types 2 and 3 were characterized by all analytical and spectroscopic data. The molecular structure of 2 was confirmed by single-crystal X-ray analysis. It is observed that the nature of phosphine ligands plays an important role in the isomerization of 1-alkenes. When the chelated diphosphine is used, the internal isomerization reaction by [Ru3(CO)10(dppe)] (3) is completed relatively in less time compared to other derivatives. As per the DFT calculations, the observed reaction rate for the alkene isomerization may be explained based on the relative stability of 1, 2, and 3. The CO abstraction step is highly feasible in 3, the least stable among the three, thus the reaction occurs at the highest rate. Due to the increased relative stability from 2 to 1, the reaction requires more time at elevated temperatures and the rate decreases as a consequence.

CATALYTIC HYDROCARBON DEHYDROGENATION

A catalyst for dehydrogenation of hydrocarbons includes a support including zirconium oxide and Linde type L zeolite (L-zeolite). A concentration of the zirconium oxide in the catalyst is in a range of from 0.1 weight percent (wt. %) to 20 wt. %. The catalyst includes from 5 wt. % to 15 wt. % of an alkali metal or alkaline earth metal. The catalyst includes from 0.1 wt. % to 10 wt. % of tin. The catalyst includes from 0.1 wt. % to 8 wt. % of a platinum group metal. The alkali metal or alkaline earth metal, tin, and platinum group metal are disposed on the support.

C-F activation reactions at germylium ions: Dehydrofluorination of fluoralkanes

Reactions of the trityl cations with germanes afford the germylium ions [R3Ge][B(C6F5)4] (1a: R = Et, 1b: R = Ph, 1c: R = nBu). These compounds react with germane or fluorogermane to give polynuclear species, which are sources of the mononuclear ions, The latter convert with phosphines to yield the [R3Ge-PR3]+ (4a: R = Et, 4b: R = Ph) cations. Catalytic dehydrofluorination reactions were observed for the C-F bond activation of fluoroalkanes when using germanes as hydrogen source.

Competitive adsorptions between thiophenic compounds over a CoMoS/Al2O3 catalyst under deep HDS of FCC gasoline

The transformation of various model sulfur compounds (2-methylthiophene: 2MT, 3-methylthiophene: 3MT and benzothiophene: BT) representative of sulfur compounds in FCC gasoline was investigated over a CoMoS/Al2O3 catalyst. More specifically, a quantitative reactivity scale was established with BT being more reactive than 3MT and 2MT. In mixture, their reactivity was reduced due to the presence of the other sulfur compound, the scale of reactivity being preserved. BT strongly inhibits the transformation of 2MT. With a single kinetic model based on a Langmuir Hinshelwood formalism, kinetic and adsorption parameters were calculated and the results explained by mutual competitive adsorption between 2MT and BT with a higher adsorption constant for BT compared to that of 2MT.

Bimolecular Coupling as a Vector for Decomposition of Fast-Initiating Olefin Metathesis Catalysts

The correlation between rapid initiation and rapid decomposition in olefin metathesis is probed for a series of fast-initiating, phosphine-free Ru catalysts: the Hoveyda catalyst HII, RuCl2(L)(=CHC6H4-o-OiPr); the Grela catalyst nG (a derivative of HII with a nitro group para to OiPr); the Piers catalyst PII, [RuCl2(L)(=CHPCy3)]OTf; the third-generation Grubbs catalyst GIII, RuCl2(L)(py)2(=CHPh); and dianiline catalyst DA, RuCl2(L)(o-dianiline)(=CHPh), in all of which L = H2IMes = N,N′-bis(mesityl)imidazolin-2-ylidene. Prior studies of ethylene metathesis have established that various Ru metathesis catalysts can decompose by β-elimination of propene from the metallacyclobutane intermediate RuCl2(H2IMes)(κ2-C3H6), Ru-2. The present work demonstrates that in metathesis of terminal olefins, β-elimination yields only ca. 25-40% propenes for HII, nG, PII, or DA, and none for GIII. The discrepancy is attributed to competing decomposition via bimolecular coupling of methylidene intermediate RuCl2(H2IMes)(=CH2), Ru-1. Direct evidence for methylidene coupling is presented, via the controlled decomposition of transiently stabilized adducts of Ru-1, RuCl2(H2IMes)Ln(=CH2) (Ln = pyn′; n′ = 1, 2, or o-dianiline). These adducts were synthesized by treating in situ-generated metallacyclobutane Ru-2 with pyridine or o-dianiline, and were isolated by precipitating at low temperature (-116 or -78 °C, respectively). On warming, both undergo methylidene coupling, liberating ethylene and forming RuCl2(H2IMes)Ln. A mechanism is proposed based on kinetic studies and molecular-level computational analysis. Bimolecular coupling emerges as an important contributor to the instability of Ru-1, and a potentially major pathway for decomposition of fast-initiating, phosphine-free metathesis catalysts.

Cobalt-Iron-Manganese Catalysts for the Conversion of End-of-Life-Tire-Derived Syngas into Light Terminal Olefins

Co-Fe-Mn/γ-Al2O3 Fischer–Tropsch synthesis (FTS) catalysts were synthesized, characterized and tested for CO hydrogenation, mimicking end-of-life-tire (ELT)-derived syngas. It was found that an increase of C2-C4 olefin selectivities to 49 % could be reached for 5 wt % Co, 5 wt % Fe, 2.5 wt % Mn/γ-Al2O3 with Na at ambient pressure. Furthermore, by using a 5 wt % Co, 5 wt % Fe, 2.5 wt % Mn, 1.2 wt % Na, 0.03 wt % S/γ-Al2O3 catalyst the selectivity towards the fractions of C5+ and CH4 could be reduced, whereas the selectivity towards the fraction of C4 olefins could be improved to 12.6 % at 10 bar. Moreover, the Na/S ratio influences the ratio of terminal to internal olefins observed as products, that is, a high Na loading prevents the isomerization of primary olefins, which is unwanted if 1,3-butadiene is the target product. Thus, by fine-tuning the addition of promoter elements the volume of waste streams that need to be recycled, treated or upgraded during ELT syngas processing could be reduced. The most promising catalyst (5 wt % Co, 5 wt % Fe, 2.5 wt % Mn, 1.2 wt % Na, 0.03 wt % S/γ-Al2O3) has been investigated using operando transmission X-ray microscopy (TXM) and X-ray diffraction (XRD). It was found that a cobalt-iron alloy was formed, whereas manganese remained in its oxidic phase.

Alkanethiolate-capped palladium nanoparticles for selective catalytic hydrogenation of dienes and trienes

Selective hydrogenation of dienes and trienes is an important process in the pharmaceutical and chemical industries. Our group previously reported that the thiosulfate protocol using a sodium S-alkylthiosulfate ligand could generate catalytically active Pd nanoparticles (PdNP) capped with a lower density of alkanethiolate ligands. This homogeneously soluble PdNP catalyst offers several advantages such as little contamination via Pd leaching and easy separation and recycling. In addition, the high activity of PdNP allows the reactions to be completed under mild conditions, at room temperature and atmospheric pressure. Herein, a PdNP catalyst capped with octanethiolate ligands (C8 PdNP) is investigated for the selective hydrogenation of conjugated dienes into monoenes. The strong influence of the thiolate ligands on the chemical and electronic properties of the Pd surface is confirmed by mechanistic studies and highly selective catalysis results. The studies also suggest two major routes for the conjugated diene hydrogenation: the 1,2-addition and 1,4-addition of hydrogen. The selectivity between two mono-hydrogenation products is controlled by the steric interaction of substrates and the thermodynamic stability of products. The catalytic hydrogenation of trienes also results in the almost quantitative formation of mono-hydrogenation products, the isolated dienes, from both ocimene and myrcene.

β-Hydride Elimination and C-H Activation by an Iridium Acetate Complex, Catalyzed by Lewis Acids. Alkane Dehydrogenation Cocatalyzed by Lewis Acids and [2,6-Bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl]iridium

NaBArF4 (sodium tetrakis[(3,5-trifluoromethyl)phenyl]borate) was found to catalyze reactions of (Phebox)IrIII(acetate) (Phebox = 2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl) complexes, including (i) β-H elimination of (Phebox)Ir(OAc)(n-alkyl) to give (Phebox)Ir(OAc)(H) and the microscopic reverse, alkene insertion into the Ir-H bond of (Phebox)Ir(OAc)(H), and (ii) hydrogenolysis of the Ir-alkyl bond of (Phebox)Ir(OAc)(n-alkyl) and the microscopic reverse, C-H activation by (Phebox)Ir(OAc)(H), as indicated by H/D exchange experiments. For example, β-H elimination of (Phebox)Ir(OAc)(n-octyl) (2-Oc) proceeded on a time scale of minutes at -15 °C in the presence of (0.4 mM) NaBArF4 as compared with a very slow reaction at 125 °C in the absence of NaBArF4. In addition to NaBArF4, other Lewis acids are also effective. Density functional theory calculations capture the effect of the Na+ cation and indicate that it operates primarily by promoting κ2-κ1 dechelation of the acetate anion, which opens the coordination site needed to allow the observed reaction to proceed. In accord with the effect on these individual stoichiometric reactions, NaBArF4 was also found to cocatalyze, with (Phebox)Ir(OAc)(H), the acceptorless dehydrogenation of n-dodecane.

Sodium Diisopropylamide in Tetrahydrofuran: Selectivities, Rates, and Mechanisms of Alkene Isomerizations and Diene Metalations

Sodium diisopropylamide in tetrahydrofuran is an effective base for the metalation of 1,4-dienes and isomerization of alkenes. Dienes metalate via tetrasolvated sodium amide monomers, whereas 1-pentene is isomerized by trisolvated monomers. Facile, highly Z-selective isomerizations are observed for allyl ethers under conditions that compare favorably to those of existing protocols. The selectivity is independent of the substituents on the allyl ethers; rate and computational data show that the rates, mechanisms, and roles of sodium-oxygen contacts are substituent-dependent. The competing influences of substrate coordination and solvent coordination to sodium are discussed.