A rhodium catalyst for single-step styrene production from benzene and ethylene

被引:103
作者
Vaughan, Benjamin A. [1 ]
Webster-Gardiner, Michael S. [1 ]
Cundari, Thomas R. [2 ]
Gunnoe, T. Brent [1 ]
机构
[1] Univ Virginia, Dept Chem, Charlottesville, VA 22903 USA
[2] Univ N Texas, Dept Chem, Ctr Adv Sci Comp & Modeling, Denton, TX 76203 USA
关键词
C-H BOND; OLEFINS; HYDROPHENYLATION; HYDROARYLATION; ARYLATION; SUBSTITUTION; ALKYLATION; ACTIVATION;
D O I
10.1126/science.aaa2260
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Rising global demand for fossil resources has prompted a renewed interest in catalyst technologies that increase the efficiency of conversion of hydrocarbons from petroleum and natural gas to higher-value materials. Styrene is currently produced from benzene and ethylene through the intermediacy of ethylbenzene, which must be dehydrogenated in a separate step. The direct oxidative conversion of benzene and ethylene to styrene could provide a more efficient route, but achieving high selectivity and yield for this reaction has been challenging. Here, we report that the Rh catalyst ((Fl)DAB)Rh(TFA)(eta(2)-C2H4) [(Fl)DAB is N,N'-bis(pentafluorophenyl)-2,3-dimethyl-1,4-diaza-1,3-butadiene; TFA is trifluoroacetate] converts benzene, ethylene, and Cu(II) acetate to styrene, Cu(I) acetate, and acetic acid with 100% selectivity and yields >= 95%. Turnover numbers >800 have been demonstrated, with catalyst stability up to 96 hours.
引用
收藏
页码:421 / 424
页数:4
相关论文
共 40 条
[1]  
American Chemical Society, 1961, CHEM ENG NEWS ARCH, V39, P52
[2]   Transition metal catalyzed hydroarylation of olefins using unactivated substrates: Recent developments and challenges [J].
Andreatta, Jeremy R. ;
McKeown, Bradley A. ;
Gunnoe, T. Brent .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) :305-315
[3]  
[Anonymous], 1977, CRC handbook of chemistry and physics
[4]   Hydrophenylation of ethylene using a cationic Ru(II) catalyst: comparison to a neutral Ru(II) catalyst [J].
Burgess, Samantha A. ;
Joslin, Evan E. ;
Gunnoe, T. Brent ;
Cundari, Thomas R. ;
Sabat, Michal ;
Myers, William H. .
CHEMICAL SCIENCE, 2014, 5 (11) :4355-4366
[5]   Acid-catalyzed synthesis of mono- and dialkyl benzenes over zeolites:: Active sites, zeolite topology, and reaction mechanisms [J].
Cejka, J ;
Wichterlová, B .
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2002, 44 (03) :375-421
[6]  
Chen S. S., 2000, KIRK OTHMER ENCY CHE, P325
[7]  
Eckert M., 2000, ULLMANNS ENCY IND CH, P1
[8]   Ru(II) Catalysts Supported by Hydridotris(pyrazolyl)borate for the Hydroarylation of Olefins: Reaction Scope, Mechanistic Studies, and Guides for the Development of Improved Catalysts [J].
Foley, Nicholas A. ;
Lee, John P. ;
Ke, Zhuofeng ;
Gunnoe, T. Brent ;
Cundari, Thomas R. .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (05) :585-597
[9]   AROMATIC SUBSTITUTION OF OLEFINS .6. ARYLATION OF OLEFINS WITH PALLADIUM(II) ACETATE [J].
FUJIWARA, Y ;
MORITANI, I ;
DANNO, S ;
ASANO, R ;
TERANISH.S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (25) :7166-&
[10]   Ethylbenzene Synthesis and Benzene Transalkylation with Diethylbenzenes on Zeolite Catalysts [J].
Gerzeliev, I. M. ;
Khadzhiev, S. N. ;
Sakharova, I. E. .
PETROLEUM CHEMISTRY, 2011, 51 (01) :39-48