Hydroformylation of 1-hexene catalyzed by nickel systems containing phosphines as ancillary ligand(Hydroformylation of 1-hexene with nickel systems)
Hidroformilación de 1-hexeno catalizada por sistemas de níquel conteniendo fosfinas como ligandos espectadores(Hidroformilación de 1-hexeno con sistemas de níquel)
Keywords:
Hydroformylation, catalysis, 1-hexene, nickel, triphenylphosphine
Abstract
In the present work, it was studied the hydroformylation of 1-hexene by using catalytic systems formed in situ by addition of triphenylphosphine to the nickel salt, NiCl2.6H2O, under mild reaction conditions (125 ºC and 50 atm syn-gas). The system that presented the highest catalytic activity was the one prepared by addition of 8 equivalents of triphenylphosphine to the nickel salt (Ni/8PPh3), obtaining a n/i ratio close to 3. The addition of amines produces the inhibition of this reaction. The systems containing bi- and tridentate phosphine showed to be inactive for this reaction. A coordination chemistry study allowed us to isolate and characterize the complex [Ni(CO)2(PPh3)2], which is proposed as the possible resting state for the hydroformylation reaction.
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References
BAYON J.C. Carbonilación en Fundamentos y Aplicaciones de la Catálisis Homogénea (Eds. ORO, L.A., SOLA, E.), INO Reproducciones S.A. Zaragoza (España). 75-92. 2000
JOO F. Aqueous Organometallic Catalysis in Catalysis by Metal Complexes (Eds. James B., van Leeuwen P.W.N.M.). Kluwer Academic Publishers. Dordrecht (The Netherlands). 149-190. 2001.
FROHNING C.D., KOHLPAINTNER C.W., BOHNEN H-W. Hydroformylation (OXO Synthesis, Roelen Reaction) in Applied homogeneous catalysis with organometallic compounds (Eds. CORNILS B, HERRMANN W.A.). Vol 1. 2nd Edn. Wiley. Weinheim. 31–103.
2002.
BHADURI S., MUKESH D. Homogeneous Catalysis: Mechanisms and Industrial Applications. Wiley. Nueva York (USA). 141-152. 2014.
GUANIPA V.J., MELEAN L.G., MODROÑO-ALONSO M., GONZÁLEZ A., ROSALES M., LÓPEZ-LINARES F., BARICELLI P.J. Appl Catal A: Gen 358:21. 2009.
MODROÑO-ALONSO M., GUANIPA V.J., MELEAN L.G., ROSALES M., GONZÁLEZ A., BARICELLI P.J. Appl Catal A: Gen 358:211. 2009.
MELEAN L.G., RIVERA S., GUANIPA V.J., MODROÑO-ALONSO M., GONZÁLEZ A., ROSALES M., BARICELLI P.J. Hydrocarbon World 6:12. 2011.
ROSALES M., BARICELLI P.J., GONZALEZ A. Ciencia 20: 73-85. 2012.
BARICELLI P.J., MELEAN L.G., MODROÑO-ALONSO M., RODRÍGUEZ A., ROSALES M., GONZÁLEZ A. Catal Today 247:124. 2015.
BEHR A., WESTFECHTEL A., PÉREZ GOMES J Chem Eng Technol 31:700. 2008.
WHITEKER G.T., COBLEY C.J. Top Organomet Chem 42:35. 2012.
FRANKE R., SELENT D., BÖRNER A. Chem Rev 112:5675, 2012.
ROSALES, M., ROSALES, J., PACHECO, I., BARICELLI, P.J., MELEÁN, L.G., ARGUELLO, E. Ciencia 22: 95-103. 2014.
HEBRARD, F., KALCK, P. Chem Rev 109:4272-4282. 2009.
VAN LEEUWEN P.W.N.M., CLAVER C. Rhodium catalyzed hydroformylation. Kluwer Academic Publishers. Dordrecht (The Netherlands). 2000.
DEL RIO, I., PAIMES, O., VAN LEEUWEN P.W.N.M., CLAVER, C. J. Organomet Chem 608: 115-121, 2000
ROSALES M., GONZALEZ A., GUERRERO Y., PACHECO I., SANCHEZ-DELGADO R.A. J Mol Catal A: Chem 270: 241-249. 2007.
ROSALES M., CHACON G., GONZALEZ A., PACHECO I., BARICELLI P. MELEAN L.G. J Mol Catal A: Chem 270: 250-256. 2007.
PROSPECH, J., FLEISCHER, I., FRANKE, R., BUSCHHOLZ, S., BELLER, M. Angew Chem Int Ed 52:2852-2872. 2013
CHIRIK, P., MORRIS, R. Acc Chem Res 48: 2495. 2015
BEHR, A., NEUBERT, P. Applied homogeneous Catalysis. Wiley-VCH, Alemania. 274-281. 2012.
TANG, C., ZENG T.Y., CAO, P., YANG, X., Wang, G. Catal Lett 129: 189-193. 2009
BARTIK, T., BUM, B.B., BARTIK, B., HANSON, B.E. Inorg Chem 33: 164-169. 1994
TOLMAN, C.A. Chem Rev 77: 313-348. 1977.
TOLMAN, C.A. J Am Chem Rev 92: 2956-2965. 1970.
LE PAGE, M.D. The synthesis, characterization and reactivity of nickel-2-pyridinephosphine complexes. Thesis submitted in partial fulfillments of the requirements for the Degree of Doctor of Philosophy. Department of Chemistry. The University of British Columbia. 2000.
VAN LEEUWEN P.W.N.M., CLAVER C. Rhodium catalyzed hydroformylation. Kluwer Academic Publishers. Dordrecht (The Netherlands). 2000.
DEL RIO, I., PAIMES, O., VAN LEEUWEN P.W.N.M., CLAVER, C. J. Organomet Chem 608: 115-121, 2000
ROSALES M., GONZALEZ A., GUERRERO Y., PACHECO I., SANCHEZ-DELGADO R.A. J Mol Catal A: Chem 270: 241-249. 2007.
ROSALES M., CHACON G., GONZALEZ A., PACHECO I., BARICELLI P. MELEAN L.G. J Mol Catal A: Chem 270: 250-256. 2007.
PROSPECH, J., FLEISCHER, I., FRANKE, R., BUSCHHOLZ, S., BELLER, M. Angew Chem Int Ed 52:2852-2872. 2013
CHIRIK, P., MORRIS, R. Acc Chem Res 48: 2495. 2015
BEHR, A., NEUBERT, P. Applied homogeneous Catalysis. Wiley-VCH, Alemania. 274-281. 2012.
TANG, C., ZENG T.Y., CAO, P., YANG, X., Wang, G. Catal Lett 129: 189-193. 2009
BARTIK, T., BUM, B.B., BARTIK, B., HANSON, B.E. Inorg Chem 33: 164-169. 1994
TOLMAN, C.A. Chem Rev 77: 313-348. 1977.
TOLMAN, C.A. J Am Chem Rev 92: 2956-2965. 1970.
LE PAGE, M.D. The synthesis, characterization and reactivity of nickel-2-pyridinephosphine complexes. Thesis submitted in partial fulfillments of the requirements for the Degree of Doctor of Philosophy. Department of Chemistry. The University of British Columbia. 2000.
JOO F. Aqueous Organometallic Catalysis in Catalysis by Metal Complexes (Eds. James B., van Leeuwen P.W.N.M.). Kluwer Academic Publishers. Dordrecht (The Netherlands). 149-190. 2001.
FROHNING C.D., KOHLPAINTNER C.W., BOHNEN H-W. Hydroformylation (OXO Synthesis, Roelen Reaction) in Applied homogeneous catalysis with organometallic compounds (Eds. CORNILS B, HERRMANN W.A.). Vol 1. 2nd Edn. Wiley. Weinheim. 31–103.
2002.
BHADURI S., MUKESH D. Homogeneous Catalysis: Mechanisms and Industrial Applications. Wiley. Nueva York (USA). 141-152. 2014.
GUANIPA V.J., MELEAN L.G., MODROÑO-ALONSO M., GONZÁLEZ A., ROSALES M., LÓPEZ-LINARES F., BARICELLI P.J. Appl Catal A: Gen 358:21. 2009.
MODROÑO-ALONSO M., GUANIPA V.J., MELEAN L.G., ROSALES M., GONZÁLEZ A., BARICELLI P.J. Appl Catal A: Gen 358:211. 2009.
MELEAN L.G., RIVERA S., GUANIPA V.J., MODROÑO-ALONSO M., GONZÁLEZ A., ROSALES M., BARICELLI P.J. Hydrocarbon World 6:12. 2011.
ROSALES M., BARICELLI P.J., GONZALEZ A. Ciencia 20: 73-85. 2012.
BARICELLI P.J., MELEAN L.G., MODROÑO-ALONSO M., RODRÍGUEZ A., ROSALES M., GONZÁLEZ A. Catal Today 247:124. 2015.
BEHR A., WESTFECHTEL A., PÉREZ GOMES J Chem Eng Technol 31:700. 2008.
WHITEKER G.T., COBLEY C.J. Top Organomet Chem 42:35. 2012.
FRANKE R., SELENT D., BÖRNER A. Chem Rev 112:5675, 2012.
ROSALES, M., ROSALES, J., PACHECO, I., BARICELLI, P.J., MELEÁN, L.G., ARGUELLO, E. Ciencia 22: 95-103. 2014.
HEBRARD, F., KALCK, P. Chem Rev 109:4272-4282. 2009.
VAN LEEUWEN P.W.N.M., CLAVER C. Rhodium catalyzed hydroformylation. Kluwer Academic Publishers. Dordrecht (The Netherlands). 2000.
DEL RIO, I., PAIMES, O., VAN LEEUWEN P.W.N.M., CLAVER, C. J. Organomet Chem 608: 115-121, 2000
ROSALES M., GONZALEZ A., GUERRERO Y., PACHECO I., SANCHEZ-DELGADO R.A. J Mol Catal A: Chem 270: 241-249. 2007.
ROSALES M., CHACON G., GONZALEZ A., PACHECO I., BARICELLI P. MELEAN L.G. J Mol Catal A: Chem 270: 250-256. 2007.
PROSPECH, J., FLEISCHER, I., FRANKE, R., BUSCHHOLZ, S., BELLER, M. Angew Chem Int Ed 52:2852-2872. 2013
CHIRIK, P., MORRIS, R. Acc Chem Res 48: 2495. 2015
BEHR, A., NEUBERT, P. Applied homogeneous Catalysis. Wiley-VCH, Alemania. 274-281. 2012.
TANG, C., ZENG T.Y., CAO, P., YANG, X., Wang, G. Catal Lett 129: 189-193. 2009
BARTIK, T., BUM, B.B., BARTIK, B., HANSON, B.E. Inorg Chem 33: 164-169. 1994
TOLMAN, C.A. Chem Rev 77: 313-348. 1977.
TOLMAN, C.A. J Am Chem Rev 92: 2956-2965. 1970.
LE PAGE, M.D. The synthesis, characterization and reactivity of nickel-2-pyridinephosphine complexes. Thesis submitted in partial fulfillments of the requirements for the Degree of Doctor of Philosophy. Department of Chemistry. The University of British Columbia. 2000.
VAN LEEUWEN P.W.N.M., CLAVER C. Rhodium catalyzed hydroformylation. Kluwer Academic Publishers. Dordrecht (The Netherlands). 2000.
DEL RIO, I., PAIMES, O., VAN LEEUWEN P.W.N.M., CLAVER, C. J. Organomet Chem 608: 115-121, 2000
ROSALES M., GONZALEZ A., GUERRERO Y., PACHECO I., SANCHEZ-DELGADO R.A. J Mol Catal A: Chem 270: 241-249. 2007.
ROSALES M., CHACON G., GONZALEZ A., PACHECO I., BARICELLI P. MELEAN L.G. J Mol Catal A: Chem 270: 250-256. 2007.
PROSPECH, J., FLEISCHER, I., FRANKE, R., BUSCHHOLZ, S., BELLER, M. Angew Chem Int Ed 52:2852-2872. 2013
CHIRIK, P., MORRIS, R. Acc Chem Res 48: 2495. 2015
BEHR, A., NEUBERT, P. Applied homogeneous Catalysis. Wiley-VCH, Alemania. 274-281. 2012.
TANG, C., ZENG T.Y., CAO, P., YANG, X., Wang, G. Catal Lett 129: 189-193. 2009
BARTIK, T., BUM, B.B., BARTIK, B., HANSON, B.E. Inorg Chem 33: 164-169. 1994
TOLMAN, C.A. Chem Rev 77: 313-348. 1977.
TOLMAN, C.A. J Am Chem Rev 92: 2956-2965. 1970.
LE PAGE, M.D. The synthesis, characterization and reactivity of nickel-2-pyridinephosphine complexes. Thesis submitted in partial fulfillments of the requirements for the Degree of Doctor of Philosophy. Department of Chemistry. The University of British Columbia. 2000.
Published
2021-05-24
How to Cite
Rosales, M., Lugo, D., González, Ángel, & Baricelli, P. (2021). Hydroformylation of 1-hexene catalyzed by nickel systems containing phosphines as ancillary ligand(Hydroformylation of 1-hexene with nickel systems): Hidroformilación de 1-hexeno catalizada por sistemas de níquel conteniendo fosfinas como ligandos espectadores(Hidroformilación de 1-hexeno con sistemas de níquel). Ciencia, 25(3-4), 129-135. Retrieved from https://produccioncientificaluz.org/index.php/ciencia/article/view/35986
Section
Química/Chemistry
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