Rhodium-catalyzed hydroformylation of C6 alkenes and alkene mixtures – a comparative study in homogeneous and aqueous-biphasic media using PPh3, TPPTS and TPPMS ligands

Baricelli, Pablo J.; Lujano, E.; Modroño, María Esther Barreal; Marrero, A.C.; Garcia, Yeimy; Fuentes, Alberto; Sánchez‐Delgado, Roberto A.

doi:10.1016/j.jorganchem.2004.06.051

Cited by 32 publications

(20 citation statements)

References 9 publications

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“…The complexes RhH(CO) 4 , RhH(CO) 2 (PPh 3 ) 2 and RhH(CO) 2 (diphos) 2 showed to be active precatalysts for the hydroformylation of 1-hexene in toluene solution under moderate temperature and pressure (120 °C, 3 atm of syn-gas) yielding exclusively the corresponding aldehydes, heptanal and 2-methyl-hexanal (eq. 1).…”

Section: Resultsmentioning

confidence: 99%

“…Solvents were purified by known procedures. RhH(CO) 4 , RhH(CO) 2 (PPh 3 ) 2 and RhH(CO) 2 (diphos) 2 were prepared in situ by reaction of Rh(acac)(CO) 2 [6] with syn gas in absence of phosphine, in the presence of two equivalents of PPh 3 and one equivalent of the corresponding diphosphine, respectively. The reaction procedure was similar to that reported earlier [7].…”

Section: Methodsmentioning

confidence: 99%

“…Recently, Baricelli et al [4,5] have reported the use of ruthenium and rhodium complexes containing triphenylphosphine and/or its meta-sulfonato derivatives in the homogeneous and aqueous-biphasic hydroformylation of olefin mixtures as models of naphtha components. In this paper, we describe the effect of the addition of sulfur compounds, such as triphenylphosphine sulfide (TPPS), thiophene (T), benzo[b]thiophene (BT) and dibenzo[b,d]thiophene (DBT), on the hydroformylation of 1-hexene catalyzed by rhodium complexes RhH(CO) 4 , RhH(CO) 2 (PPh 3 ) 2 and RhH(CO) 2 (diphos) 2 .…”

Section: Introductionmentioning

confidence: 99%

“…In this paper, we describe the effect of the addition of sulfur compounds, such as triphenylphosphine sulfide (TPPS), thiophene (T), benzo[b]thiophene (BT) and dibenzo[b,d]thiophene (DBT), on the hydroformylation of 1-hexene catalyzed by rhodium complexes RhH(CO) 4 , RhH(CO) 2 (PPh 3 ) 2 and RhH(CO) 2 (diphos) 2 .…”

Section: Introductionmentioning

confidence: 99%

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Effect of the addition of sulfur compounds on the hydroformylation of 1-hexene catalyzed by rhodium systems

Rosales

Chacón

González

et al. 2007

React Kinet Catal Lett

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The effect of the addition of triphenylphosphine sulfide, thiophene, benzo[b]thiophene and dibenzo [b,d]thiophene on the hydroformylation of 1-hexene catalyzed by rhodium complexes RhH(CO) 4 , RhH(CO) 2 (PPh 3 ) 2 and RhH(CO) 2 (diphos) was studied. The addition of these sulfur compounds did not affect the activity of non modified rhodium precatalysts, decreased the activity of the PPh 3 -modified one and increased the activity of the diphos-modified ones, which is indicative of the sulfur tolerance of these precatalysts. The linear to branched ratio (l/b) varied from 0.5 to 3.4 for the non-modified precatalyst, and from 1.7 to 3.3 for the phosphine-modified ones.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Effect of the addition of sulfur compounds on the hydroformylation of 1-hexene catalyzed by rhodium systems

Rosales

Chacón

González

et al. 2007

React Kinet Catal Lett

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“…Since the Ruhrchemie-Rhone-Poulenc propene hydroformylation process in 1984 [1,2] the use of water-soluble metal complex catalysts has been recognized as an effective method for catalyst, product separation, and catalyst recycling [3][4][5][6][7][8]. A new hydroformylation application is the treatment of C4-C7 alkene mixtures from refinery cuts, converting some of the alkenes into valuable oxygenates (aldehydes or alcohols), that improves the combustion properties of the fuel.…”

Section: Introductionmentioning

confidence: 99%

Aqueous biphasic olefin hydroformylation catalyzed by water-soluble rhodium complexes

Suárez

Fontal

León

et al. 2006

Transition Met Chem

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Catalysis with water-soluble rhodium complexes, RhCl(CO)(TPPMS) 2 , [TPPMS = P(C 6 H 5 ) 2 (C 6 H 4 SO 3 )] (1), RhCl(CO)(TPPDS) 2 , [TPPDS = P(C 6 H 5 )(C 6 H 4 SO 3 ) 2 ] (2) and RhCl(CO)(TPPTS) 2 , [TPPTS = P(C 6 H 4 SO 3 ) 3 ] (3) in hydroformylation of 1-hexene, 2-pentene, 2,3-dimethyl-1-butene, cyclohexene and several mixtures of these olefins have been studied, under moderate reaction conditions (T: 50-150°C; pCO/pH 2 = 1; total p: 14-68 bar; Substrate/ Catalyst: 600/1) in biphasic toluene/water media. The catalytic system shows high activity but low selectivity. The linear and branched oxygenated products obtained are equally useful in naphtha upgrading, as observed in the real El Palito naphtha tried. The catalysts can be recycled several times without significant activity loss.

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Synthesis, characterization and hydroformylation activity of 7‐azaindolate‐bridged dinuclear rhodium(I)phosphines with pendant polar‐groups

Vasam

Modem

Kankala

et al. 2009

Applied Organom Chemis

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(where azi = 7-azaindolate, L = polar phosphine) were isolated from the reaction of [Rh(µ-Cl)(CO) 2 ] 2 with 7-azaindolate followed by some polar mono-and bis-phosphines (L 1 -L 8 ). A relationship between δ 31 P-NMR and ν(CO) values was considered to define the impact of polar-groups on σ -donor properties of the phosphines. These compounds were evaluated as catalyst precursors in the hydroformylation of 1-hexene and 1-dodecene both in mono-and biphasic aqueous organic systems. While the biphasic hydroformylations (water + toluene) gave exclusively the aldehydes, the monophasic one (aqueous ethanol) showed propensity to form both aldehydes and alcohols. The influence of bimetallic cooperative effects, and σ -donor and hydrophilic properties of the phosphines with pendant polar-groups in enhancing the yields and selectivity of hydroformylation products was emphasized. In addition, when strong σ -donor phosphine was used, the π -acceptor nature of pyridine ring of 7-azaindolate spacer was found to be a considerable factor in facilitating the facile cleavage of CO group during hydroformylation and in supplementing the cooperative effects. Copyright

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Rhodium-catalyzed hydroformylation of C6 alkenes and alkene mixtures – a comparative study in homogeneous and aqueous-biphasic media using PPh3, TPPTS and TPPMS ligands

Cited by 32 publications

References 9 publications

Effect of the addition of sulfur compounds on the hydroformylation of 1-hexene catalyzed by rhodium systems

Effect of the addition of sulfur compounds on the hydroformylation of 1-hexene catalyzed by rhodium systems

Aqueous biphasic olefin hydroformylation catalyzed by water-soluble rhodium complexes

Synthesis, characterization and hydroformylation activity of 7‐azaindolate‐bridged dinuclear rhodium(I)phosphines with pendant polar‐groups

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