10281-53-5Relevant articles and documents
Selective reduction of mono- and disubstituted olefins by NaBH4 and catalytic RuCl3
Sharma, Pawan K.,Kumar, Surender,Kumar, Pawan,Nielsen, Poul
, p. 8704 - 8708 (2007)
Direct use of the relatively inexpensive reagent, RuCl3 × H2O, as a catalyst for the reductions of olefins in the presence of water is reported. The combination of cheap and readily available sodium borohydride and a catalytic amount of RuCl3 × H2O selectively reduces mono- and disubstituted olefins, whereas trisubstituted olefins, unless activated, and benzyl ethers remain inert.
Colloid and Nanosized Catalysts in Organic Synthesis: XXII. Hydrogenation of Cycloolefins Catalyzed by Immobilized Transition Metals Nanoparticles in a Three-Phase System
Nebykov,Popov, Yu. V.,Mokhov,Latyshova,Shcherbakova,Nemtseva,Shishkin
, p. 1985 - 1989 (2019)
The processes of unsaturated cyclic hydrocarbons hydrogenation in a three-phase gas-liquid-solid catalyst system in the presence of nanostructured nickel, cobalt, or iron catalysts in a flow reactor at 130°C and atmospheric pressure have studied. RX3Extra activated carbon, γ-Al2O3, NaX zeolite, and Purolite CT-175 cation-exchange resin have been used as supports; NaBH4 and NH2NH2·H2O were used as reducing agents. The catalytic activity of supported nanoparticles and their selectivity with respect to the product of exhaustive hydrogenation have been investigated.
Iridium(I) complexes with anionic N-heterocyclic carbene ligands as catalysts for the hydrogenation of alkenes in nonpolar media
Kolychev, Eugene L.,Kronig, Sabrina,Brandhorst, Kai,Freytag, Matthias,Jones, Peter G.,Tamm, Matthias
, p. 12448 - 12459 (2013)
A series of lithium complexes of anionic N-heterocyclic carbenes that contain a weakly coordinating borate moiety (WCA-NHC) was prepared in one step from free N-heterocyclic carbenes by deprotonation with n-butyl lithium followed by borane addition. The reaction of the resulting lithium-carbene adducts with [M(COD)Cl]2 (M = Rh, Ir; COD = 1,5-cyclooctadiene) afforded zwitterionic rhodium(I) and iridium(I) complexes of the type [(WCA-NHC)M(COD)], in which the metal atoms exhibit an intramolecular interaction with the N-aryl groups of the carbene ligands. For M = Rh, the neutral complex [(WCA-NHC)Rh(CO)2] and the ate complex (NEt4)[(WCA-NHC) Rh(CO)2Cl] were prepared, with the latter allowing an assessment of the donor ability of the ligand by IR spectroscopy. The zwitterionic iridium-COD complexes were tested as catalysts for the homogeneous hydrogenation of alkenes, which can be performed in the presence of nonpolar solvents or in the neat alkene substrate. Thereby, the most active complex showed excellent stability and activity in hydrogenation of alkenes at low catalyst loadings (down to 10 ppm).
Magnetically recyclable Ru immobilized on amine-functionalized magnetite nanoparticles and its high selectivity to prepare cis-pinane
Liu, Yue,Li, Lu,Liu, Shiwei,Xie, Congxia,Yu, Shitao
, p. 269 - 275 (2016)
cis-Pinane was efficient and selective prepared through the hydrogenation of α-pinene base on Ru nanoparticles stabilized by amine-functionalized magnetite nanoparticles (Fe3O4/NH2/Ru). The effects o`f changing carbon chain length on amine-functionalized catalyst formation have also been investigated. The characterization results showed that Ru nanoparticles could be efficient loaded by 1, 6-hexanediamine functionalized magnetite nanoparticles. At the same time, Fe3O4/1, 6-hexanediamine/Ru had good superparamagnetic properties and that the introduction of the amine-functionalized improved the monodispersity, morphological regularity and size uniformity of the Ru nanoparticles. The Fe3O4/1, 6-hexanediamine/Ru catalyst was completely recoverable with the simple application of an external magnetic field and the catalytic efficiency showed no obvious loss for the hydrogenation of α-pinene even after ten repeated cycles.
Preparation and Absolute Configuration of (-)-(E)-α-trans-Bergamotenone
Chapuis, Christian,Barthe, Michel,Muller, Bernard L.,Schulte-Elte, Karl H.
, p. 153 - 162 (1998)
The synthesis, absolute configuration, and olfactive evaluation of (-)-(E)-α-trans-bergamotenone (=(-)-(1′S,6′R,E)-5-(2′,6′-dimethylbicyclo[3.1.1]hept- 2′-en-6′-yl)pent-3-en-2-one; (-)-1), as well as its homologue (-)-19 are reported. The previously arbitrarily attributed absolute configuration of 1 and of (-)-α-trans-bergamotene (=(-)-(1S,6R)-2,6-dimethyl-6-(4-methylpent-3-enyl)bicyclo[3.1.1]hept-2-ene; (-)-2), together with those of the structurally related aldehydes (-)-3a,b and alcohols (-)-4a,b, have been rigorously assigned.
Hydrogenation and Skeleton Rearrangements of α-Pinene on Heterogeneous Catalysts
Bazhenov,Kas'yanova,Bokin,Kutepov,Khazipova,Travkin,Shchadneva,Khusnutdinov,Dzhemilev
, p. 234 - 237 (2003)
Hydrogenation and isomerization of α-pinene on heterogeneous catalysts were studied, and conditions were found for hydrogenation of pinene to cis-pinane on nickel catalysts and for its dehydrogenation to p-cymene on decationized zeolite Y.
Rhodium catalyzed hydroformylation of β-pinene and camphene: effect of phosphorous ligands and reaction conditions on stereoselectivity
Barros, Humberto J. V.,Ospina, Maria L.,Arguello, Eduardo,Rocha, William R.,Gusevskaya, Elena V.,Santos, Eduardo N. dos
, p. 150 - 157 (2003)
The effect of phosphorous ligands on the rhodium catalyzed hydroformylation of β-pinene and camphene has been studied. In unmodified systems, β-pinene undergoes a fast isomerization to α-pinene. At longer reaction times and higher temperatures, the isomerization equilibrium is shifted resulting in the 80 percent chemoselectivity for β-pinene hydrofromylation products (97 percent trans). The addition of various diphosphines or phosphites improves the chemoselectivity and shifts the hydroformylation towards cis aldehyde 3a. Both the rate and diastereoselectivity of the hydroformylation of β-pinene are largely influenced by the basicity of auxiliary ligands, but surprisingly no correlation between their steric characteristics and the diastereoselectivity of the catalytic system has been revealed for the ligands with cone angles 128-165 deg. The systems with more basic ligands show lower activities, higher diastereoselectivities and usually higher chemoselectivities in the β-pinene hydroformylation. Camphene gives linear aldehyde 6, with virtually 100 percent regio- and chemoselectivity in both modified and unmodified systems. The addition of phosphorous ligands favors the formation of endo isomer 6b:6a/6b ca. 1/1.5 , whereas the ratio ca. 1/1 unmodified systems. Neither steric nor electronic parameters of the ligands have been found to influence significantly the diastereoselectivity of the camphene hydroformylation.
Rate constant of the α-pinene + atomic hydrogen reaction at 295 K
Vinckier,Van Hoof
, p. 527 - 534 (1994)
The rate constant of the reaction of α-pinene with atomic hydrogen was determined at 295 K using the fast-flow reactor technique directly coupled to a mass spectrometric detection technique. The value was found to be equal to (9.8 ± 3.3) × 10-13 cm3 molecules-1 s-1 and independent of the helium pressure between 1 and 2 torr. The major reaction product formed is pinane showing that the stabilization of the adduct radical C10H17, followed by a subsequent hydrogen atom addition step, is the important reaction route.
The conversion of α-pinene to: Cis-pinane using a nickel catalyst supported on a discarded fluid catalytic cracking catalyst with an ionic liquid layer
Hu, Shunyou,Wang, Linlin,Chen, Xiaopeng,Wei, Xiaojie,Tong, Zhangfa,Yin, Lijiang
, p. 5978 - 5986 (2019)
The concept of a solid catalyst coated with a thin ionic liquid layer (SCILL) was applied to the stereoselective hydrogenation of α-pinene. Nickel, a non-noble metal, was supported on a discarded fluid catalytic cracking catalyst (DF3C) and then modified with different loadings of the ionic liquid 1-ethanol-3-methylimidazolium tetrafluoroborate ([C2OHmim][BF4]). The resulting catalysts showed a range of conversions and selectivities for the hydrogenation of α-pinene. The SCILL catalysts afforded cis-pinane with high selectivity and their activity depended on the ionic liquid loading. For an ionic liquid loading of 10 wt%, although the catalytic activity was suppressed, the selectivity and conversion could reach above 98% and 99%, respectively. In addition, the catalyst remained stable after 13 runs and the activity was almost unchanged with the conversion maintained at approximately 99%. Thus, the ionic liquid layer not only improved the selectivity for cis-pinane but also protected the active site of the catalyst and prolonged the service lifetime of the catalyst. The SCILL catalytic system provides an example of an ionic liquid catalytic system which eliminates organic solvents from the catalytic process.
Postassembly Transformation of a Catalytically Active Composite Material, Pt@ZIF-8, via Solvent-Assisted Linker Exchange
Stephenson, Casey J.,Hupp, Joseph T.,Farha, Omar K.
, p. 1361 - 1363 (2016)
2-Methylimidazolate linkers of Pt@ZIF-8 are exchanged with imidazolate using solvent-assisted linker exchange (SALE) to expand the apertures of the parent material and create Pt@SALEM-2. Characterization of the material before and after SALE was performed. Both materials are active as catalysts for the hydrogenation of 1-octene, whereas the hydrogenation of cis-cyclohexene occurred only with Pt@SALEM-2, consistent with larger apertures for the daughter material. The largest substrate, β-pinene, proved to be unreactive with H2 when either material was employed as a candidate catalyst, supporting the contention that substrate molecules, for both composites, must traverse the metal-organic framework component in order to reach the catalytic nanoparticles.
