Article

How do physical-chemical parameters influence the catalytic hydrogenation of 1,3-cyclohexadiene in ionic liquids?

Université de Lyon Institut de Chimie de Lyon, UMR 5265 CNRS-Université de Lyon 1-ESCPE Lyon, C2P2, Equipe Chimie Organometallique de Surface, ESCPE 43 Boulevard du 11 Novembre 1918, F-69616 Villeurbanne, France.
The Journal of Physical Chemistry B (impact factor: 3.7). 06/2010; 114(24):8156-65. DOI:10.1021/jp102941n pp.8156-65
Source: PubMed

ABSTRACT The catalytic hydrogenation of 1,3-cyclohexadiene using [Rh(COD)(PPh(3))(2)]NTf(2) (COD = 1,5-cyclooctadiene) was performed in two ionic liquids: 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [C(1)C(4)Im][NTf(2)], and 1-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide, [C(1)C(1)C(4)Im][NTf(2)]. It is observed that the reaction is twice as fast in [C(1)C(4)Im][NTf(2)] than in [C(1)C(1)C(4)Im][NTf(2)]. To explain the difference in reactivity, molecular interactions and the microscopic structure of ionic liquid +1,3-cyclohexadiene mixtures were studied by NMR and titration calorimetry experiments, and by molecular simulation in the liquid phase. Diffusivity and viscosity measurements allowed the characterization of mass transport in the reaction media. We could conclude that the diffusivity of 1,3-cyclohexadiene is 1.9 times higher in [C(1)C(4)Im][NTf(2)] than in [C(1)C(1)C(4)Im][NTf(2)] and that this difference could explain the lower reactivity observed in [C(1)C(1)C(4)Im][NTf(2)].

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Keywords

1,3-cyclohexadiene
 
COD
 
diffusivity
 
ionic liquid +1,3-cyclohexadiene mixtures
 
liquid phase
 
lower reactivity
 
mass transport
 
microscopic structure
 
molecular interactions
 
molecular simulation
 
NMR
 
reactivity
 
titration calorimetry experiments
 
viscosity measurements