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The Catalytic Transformation of Ethylene Using Chromium(III) Complexes with Bidentate Nitrogen-Containing Ligands

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Abstract

It has been shown that catalytic systems of the type Cr(III)/TEA/L, where Cr(III) is tris(2-ethylhexanoate)chromium(III) (Cr(EH)3), tris(acetylacetone)chromium(III) (Cr(acac)3); TEA is triethylaluminum; L is 2,2′-bipyridyne (bipy), 1,10-phenanthroline (Phen), N,N′-bis-(cyclohexyl)diazabutadiene-1,3 (DCy-DABD) and N,N′-bis-(2,6-diisopropylphenyl)diazabutadiene-1,3 (DPPh-DABD), can be employed for ethylene poly- and olygomerization at 60–80 °C and under pressure 2–3 MPa. The proton affinity of the used bidentate nitrogen-containing ligands is evaluated using quantum chemical calculations. The DCy-DABD, which has the lowest basicity, turns out to be the best ligand for the selective di- and trimerization of ethylene.

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References

  1. Dixon JT, Green MJ, Hess FM, Morgan DH (2004) Advances in selective ethylene trimerisation—a critical overview. J Organomet Chem 689(23):3641–3668. https://doi.org/10.1016/j.jorganchem.2004.06.008

    Article  CAS  Google Scholar 

  2. Agapie T (2011) Selective ethylene oligomerization: recent advances in chromium catalysis and mechanistic investigations. Coord Chem Rev 255(7–8):861–880. https://doi.org/10.1016/j.ccr.2010.11.035

    Article  CAS  Google Scholar 

  3. McGuinness DS (2011) Olefin oligomerization via metallacycles: dimerization, trimerization, tetramerization, and beyond. Chem Rev 111(3):2321–2341. https://doi.org/10.1021/cr100217q

    Article  CAS  PubMed  Google Scholar 

  4. Kinoshita S, Kawamura K, Fujita T (2011) Early-transition-metal catalysts with phenoxy–imine-type ligands for the oligomerization of ethylene. Chem Asian J 6(2):284–290. https://doi.org/10.1002/asia.201000563

    Article  CAS  PubMed  Google Scholar 

  5. van Leeuwen PWNM, Clement ND, Tschan MJL (2011) New processes for the selective production of 1-octene. Coord Chem Rev 255(13–14):1499–1517. https://doi.org/10.1016/j.ccr.2010.10.009

    Article  CAS  Google Scholar 

  6. Belov GP (2012) Tetramerization of ethylene to octene-1 (a review). Pet Chem 52(3):139–154. https://doi.org/10.1134/S0965544112030036

    Article  CAS  Google Scholar 

  7. Bryliakov KP, Talsi EP (2012) Frontiers of mechanistic studies of coordination polymerization and oligomerization of α-olefins. Coord Chem Rev 256(23–24):2994–3007. https://doi.org/10.1016/j.ccr.2012.06.023

    Article  CAS  Google Scholar 

  8. Otero A, Fernandez-Baeza J, Lara-Sanchez A, Sanchez-Barba LF (2013) Metal complexes with heteroscorpionate ligands based on the bis(pyrazol-1-yl)methane moiety: catalytic chemistry. Coord Chem Rev 257(11–12):1806–1868. https://doi.org/10.1016/j.ccr.2013.01.027

    Article  CAS  Google Scholar 

  9. Alferov KA, Babenko IA, Belov GP (2017) New catalytic systems on the basis of chromium compounds for selective synthesis of 1-hexene and 1-octene. Pet Chem 57(1):1–30. https://doi.org/10.1134/s0965544117010029

    Article  CAS  Google Scholar 

  10. Alferov KA, Belov GP, Meng Y (2017) Chromium catalysts for selective ethylene oligomerization to 1-hexene and 1-octene: recent results. Appl Catal A 542(25):71–124. https://doi.org/10.1016/j.apcata.2017.05.014

    Article  CAS  Google Scholar 

  11. Bariashir C, Huang C, Solan GA (2019) Sun W-H (2019) Recent advances in homogeneous chromium catalyst design for ethylene tri-, tetra-, oligo- and polymerization. Coord Chem Rev 385(15):208–229. https://doi.org/10.1016/j.ccr.2019.01.019

    Article  CAS  Google Scholar 

  12. Ittel SD, Johnson LK (2000) Late-metal catalysts for ethylene homo- and copolymerization. Chem Rev 100(4):1169–1204. https://doi.org/10.1021/cr9804644

    Article  CAS  PubMed  Google Scholar 

  13. Iwanga K, Tamura M (2000) US patent 6127301

  14. Zhang S, Jie S, Shi Q, Sun W-H (2007) Chromium(III) complexes bearing 2-imino-1,10-phenanthrolines: synthesis, molecular structures and ethylene oligomerization and polymerization. J Mol Catal A 276(1–2):174–183. https://doi.org/10.1016/j.molcata.2007.07.012

    Article  CAS  Google Scholar 

  15. Zhang M, Wang K, Sun W-H (2009) Chromium(III) complexes bearing 2-benzazole-1,10-phenanthrolines: synthesis, molecular structures and ethylene oligomerization and polymerization. Dalton Trans 32:6354–6363. https://doi.org/10.1039/b902361e

    Article  CAS  Google Scholar 

  16. Gordon AJ, Ford RA (1972) The Chemist’s companion. A handbook of practical data, techniques, and references. Wiley, New York

    Google Scholar 

  17. Jafarpour L, Stevens ED, Nolan SP (2000) A sterically demanding nucleophilic carbene: 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene). Thermochemistry and catalytic application in olefin metathesis. J Organomet Chem 606(1):49–54. https://doi.org/10.1016/s0022-328x(00)00260-6

    Article  CAS  Google Scholar 

  18. Briggs JR (1987) US patent 4668838

  19. Brauer G (1975) Handbuch der Praparativen anorganischen chemie. University of Michigan, Ann Arbor

    Google Scholar 

  20. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2010) Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford, CT

  21. Vilms AI, Babenko IA, Bezborodov VA, Ivanov AV, Belov GP (2017) Ethylene oligomerization over chromium(III) complexes with pyrrole derivatives. Pet Chem 57(3):244–250. https://doi.org/10.1134/s0965544117010145

    Article  CAS  Google Scholar 

  22. Riou D, Bouchoux G (2014) Protonation thermochemistry of gaseous 2,2′-, 4,4′- and 2,4′-Bipyridines and 1,10-phenanthroline. Croat Chem Acta 87(4):447–457. https://doi.org/10.5562/cca2486

    Article  Google Scholar 

  23. Oresmaa L, Haukka M, Vainiotalo P, Pakkanen TA (2002) Ab initio calculations and mass spectrometric determination of the gas-phase proton affinities of 4,4′-disubstituted 2,2′-bipyridines. J Org Chem 67(23):8216–8219. https://doi.org/10.1021/jo026126r

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Irkutsk State University, Karl Marks St., 1, Irkutsk, Russia, 664003

    Ilya A. Babenko, Igor B. Rozentsveig & Alexey I. Vilms

  2. Irkutsk Institute of Chemistry. A.E. Favorsky SB RAS, Favorsky St., 1, Irkutsk, Russia, 664033

    Evgeniy V. Kondrashov & Igor B. Rozentsveig

  3. Institute of Problems of Chemical Physics RAS, Prospect Academician Semenov, 1, Chernogolovka, Russia, 142432

    Gennadiy P. Belov

Authors
  1. Ilya A. Babenko
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  2. Evgeniy V. Kondrashov
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  3. Igor B. Rozentsveig
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  4. Gennadiy P. Belov
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  5. Alexey I. Vilms
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Correspondence to Ilya A. Babenko or Gennadiy P. Belov.

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Gennadiy P. Belov—deceased.

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Babenko, I.A., Kondrashov, E.V., Rozentsveig, I.B. et al. The Catalytic Transformation of Ethylene Using Chromium(III) Complexes with Bidentate Nitrogen-Containing Ligands. Catal Lett 150, 2873–2878 (2020). https://doi.org/10.1007/s10562-019-03080-3

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  • DOI: https://doi.org/10.1007/s10562-019-03080-3

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