Supported transition metal complexesV. Liquid phase catalytic hydrogenation of hexene-1, cyclohexene and isoprene under continuous flow conditions

Allum, K.G.; Hancock, Robert D.; Howell, I.V.; Lester, T.E.; McKenzie, S. G.; Pitkethly, R. C.; Robinson, Philip J.

doi:10.1016/0021-9517(76)90318-3

Cited by 47 publications

(6 citation statements)

References 3 publications

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“…[60] Silica-bonded complexes of Rh and Ir were used to catalyze the hydrogenation of 1-hexene, cyclohexene, and isoprene under a variety of continuous flow conditions (15-50 bar hydrogen, 20-160 8C) for 70 h without loss of activity. [61] The combination of supported ionic-liquid-phase catalysis and flow systems has been proposed as a promising new technical approach to catalysis. The Kiwi-Minsker [62] and Virtanen [63] groups used this technique for the selective hydrogenation of 1,3-cyclohexadiene and citral, respectively.…”

Section: Hydrogenation Reactions Under Flow Conditions 41 Carbon-camentioning

confidence: 99%

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

2011

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Microreactor technology and continuous flow processing in general are key features in making organic synthesis both more economical and environmentally friendly. Heterogeneous catalytic hydrogenation reactions under continuous flow conditions offer significant benefits compared to batch processes which are related to the unique gas-liquid-solid triphasic reaction conditions present in these transformations. In this review article recent developments in continuous flow heterogeneous catalytic hydrogenation reactions using molecular hydrogen are summarized. Available flow hydrogenation techniques, reactors, commonly used catalysts and examples of synthetic applications with an emphasis on laboratory-scale flow hydrogenation reactions are presented.

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Section: Hydrogenation Reactions Under Flow Conditions 41 Carbon-camentioning

confidence: 99%

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

2011

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“…Moreover, the drawbacks of homogeneous catalysis, such as the recovery of metal and the separation problem of catalyst and products, retard its practical application into wider fields. − Thus, the development of a practical heterogeneous catalyst would be desirable. Most of the studies have been concerned with supported rhodium and cobalt catalysts, − which have been tested in high-pressure autoclaves under liquid-phase reaction conditions. Kainulainen 7 et al applied the Co/SiO 2 catalyst to the liquid-phase hydroformylation of 1-hexene at 423 K and 7.5 MPa in the typical autoclave reactor and studied the effect of the different cobalt-containing precursors.…”

Section: Introductionmentioning

confidence: 99%

Low-Pressure Hydroformylation of Middle Olefins over Co and Rh Supported on Active Carbon Catalysts

Asami

et al. 2003

Energy Fuels

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The hydroformylation of olefin has been investigated on Co and Rh catalysts supported on active carbon at mild reaction conditions (403 K, 3.0 MPa) in the slurry phase reactor. Of the catalysts, Co/activated carbon catalysts showed excellent catalytic performance only in the alcoholic solvent, while Rh/activated carbon catalyst exhibited good activity in the nonpolar solvent. Rh/activated carbon catalyst showed stable activity for 14 h in the continuous feeding system, giving the total turnover number of 500. The effects of solvents were discussed in detail. The details of reaction conditions that affected the performance of the catalysts have been optimized. The higher catalytic activity was found at the lower temperature, about 403 K. About 20% of metal was dissolved from the support, a determination based on inductively coupled plasma (ICP) atomic emission spectrometry. The dissolved part was thought to deposit again on the support and work as active species as well.

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“…Immobilized homogeneous transition metal complex catalysts offer the advantage over their homogeneous counterparts of easy separation from the reactant and product solutions. − Numerous methods of heterogenization have been investigated for applications to various reactions. − However, lower activity−selectivity, leaching of the metals, and deactivation of the metal catalysts have limited the actual use of the heterogenized catalysts in the industry . Recently, Augustine et al have reported a novel approach for immobilizing homogeneous catalysts on solid supports in which the metal complex was tethered to the inorganic matrix for asymmetric hydrogenation of various alkenes, alkynes, and aldehydes. , A major advantage of this technique is that the transition metal complex is essentially present on the outer surface of the support and hence could give higher activity .…”

Section: Introductionmentioning

confidence: 99%

Hydroformylation of 1,4-Diacetoxy-2-butene Using HRh(CO)(PPh₃)₃ Tethered on Alumina as a Catalyst: Kinetic Study

Chansarkar

Kelkar

Chaudhari

2009

Ind. Eng. Chem. Res.

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Hydroformylation of 1,4-diacetoxy-2-butene (DAB) was studied using [HRh(CO)(PPh 3 ) 3 ] complex catalyst tethered on alumina using phosphotungstic acid (PTA) as an anchoring agent, with the aim to understand the product distribution, selectivity, and intrinsic kinetics. It was observed that with the tethered heterogeneous catalyst a simultaneous hydroformylation followed by deacetoxylation steps was possible, which is relevant for combining two steps in the sequence of synthesis of vitamin-A intermediate [2-formyl-4-acetoxy butene (FAB)]. 31 P cross-polarization magic angle spinning nuclear magnetic resonance (CP MAS NMR) and infrared (IR) instrumental techniques were found be the most effective techniques to establish the catalyst structure and true heterogeneity. On the basis of the spectroscopic evidence, we postulate the loss of a PPh 3 group during tethering to give HRh(CO)(PPh 3 ) 2 -PTA-Al 2 O 3 as a heterogeneous complex catalyst. Experimental data on the concentration-time and CO/H 2 consumption-time profiles were obtained and the effects of DAB concentration, CO partial pressure, H 2 partial pressure, and catalyst loading were studied in a 50 mL stirred batch reactor over a temperature range of 338-358 K. The analysis of solid-liquid-gas mass transfer effects was investigated to ensure that the reaction was operating in the kinetic regime. Various models were developed, and the best model was chosen by a model discrimination procedure. The agreement between the model prediction and the experimental data was found to be excellent. The activation energies for the hydroformylation and deacetoxylation steps were found to be 42.5 and 80.2 kJ/mol.

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Supported transition metal complexesV. Liquid phase catalytic hydrogenation of hexene-1, cyclohexene and isoprene under continuous flow conditions

Cited by 47 publications

References 3 publications

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

Low-Pressure Hydroformylation of Middle Olefins over Co and Rh Supported on Active Carbon Catalysts

Hydroformylation of 1,4-Diacetoxy-2-butene Using HRh(CO)(PPh₃)₃ Tethered on Alumina as a Catalyst: Kinetic Study

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Supported transition metal complexesV. Liquid phase catalytic hydrogenation of hexene-1, cyclohexene and isoprene under continuous flow conditions

Cited by 47 publications

References 3 publications

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

Low-Pressure Hydroformylation of Middle Olefins over Co and Rh Supported on Active Carbon Catalysts

Hydroformylation of 1,4-Diacetoxy-2-butene Using HRh(CO)(PPh3)3 Tethered on Alumina as a Catalyst: Kinetic Study

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Hydroformylation of 1,4-Diacetoxy-2-butene Using HRh(CO)(PPh₃)₃ Tethered on Alumina as a Catalyst: Kinetic Study