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Oxidative Hydrophenylation of Ethylene Using a Cationic Ru(II) Catalyst: Styrene Production with Ethylene as the Oxidant

Journal Article · · Israel Journal of Chemistry
 [1];  [2];  [3];  [4];  [5]
  1. Univ. of Virginia, Charlottesville, VA (United States). Dept. of Chemistry; University of Virginia
  2. Stephen F. Austin State Univ., Nacogdoches, TX (United States). Dept. of Chemistry & Biochemistry
  3. Univ. of Virginia, Charlottesville, VA (United States). Dept. of Chemistry; Wuhan Textile University, Wuhan, Hubei (China). School of Materials Science and Engineering
  4. Univ. of North Texas, Denton, TX (United States). Dept. of Chemistry, Center for Advanced Scientific Computing and Modeling (CASCaM)
  5. Univ. of Virginia, Charlottesville, VA (United States). Dept. of Chemistry
+ Show Author Affiliations

The complex [(MeOTTM)Ru(P(OCH2)3CEt)(NCMe)Ph][BAr'4] (MeOTMM = 4,4',4"-(methoxymethanetriyl)-tris(1-benzyl-1H-1,2,3-triazole), BAr'4 = tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) is used to catalyze the hydrophenylation of ethylene to produce styrene and ethylbenzene. The selectivity of styrene versus ethylbenzene varies as a function of ethylene pressure, and replacing the MeOTTM ligand with tris(1-phenyl-1H-1,2,3-triazol-4-yl)methanol reduces the selectivity toward styrene. For styrene production ethylene serves as the oxidant to produce ethane, as determined by both 1H NMR spectroscopy and GC-MS. The Ru(III/II) potentials of [(MeOTTM)Ru[P(OCH2)3CEt](NCMe)Ph][BAr'4] (0.86 V) and [(HC(pz5)3)Ru[P(OCH2)3CEt](NCMe)Ph][BAr'4] (0.82 V) (HC(pz5)3 = tris(5-methyl-pyrazolyl)methane) are nearly identical. Since catalytic conversion of ethylene and benzene by [(HC(pz5)3)Ru[P(OCH2)3CEt](NCMe)Ph][BAr'4] is known to selectively produce ethylbenzene, the formation of styrene using [(MeOTTM)Ru[P(OCH2)3CEt](NCMe)Ph][BAr'4] is attributed to the substituents on the triazole rings of the MeOTTM ligand.

Research Organization:
Univ. of Virginia, Charlottesville, VA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Grant/Contract Number:
SC0000776; FG02-03ER15387
OSTI ID:
1596958
Alternate ID(s):
OSTI ID: 1537573
OSTI ID: 1434551
Journal Information:
Israel Journal of Chemistry, Journal Name: Israel Journal of Chemistry Journal Issue: 10-11 Vol. 57; ISSN 0021-2148
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English

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