A Diels-Alder reaction in supercritical carbon dioxide medium.

Ikushima, Yutaka; Itô, Shota; Asano, Takashi; Yokoyama, Toshirou; Saito, Norio; Hatakeda, Kiyotaka; Goto, Tomio

doi:10.1252/jcej.23.96

Cited by 27 publications

(29 citation statements)

References 4 publications

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“…In additional experiments, the UV absorption of maleic anhydride in acetonitrile was characterized. Maleic anhydride dissolved in acetonitrile exhibits the validity of Beer's law over a wide concentration range (0.05-1000 ppm), the maximum molar absorption coefficient is 10 …”

Section: Methodsmentioning

confidence: 96%

Kinetics of a Diels−Alder Reaction of Maleic Anhydride and Isoprene in Supercritical CO₂

et al. 2001

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The kinetics of the reaction of maleic anhydride and isoprene in supercritical carbon dioxide was studied over an extended concentration range, from 5 × 10 -5 to 1.3 × 10 -2 mole fractions of both maleic anhydride and isoprene at 60 °C and pressure 100 atm. The apparent rate constant of the reaction was found to be concentration dependent, in contradiction with the literature data. The results are interpreted in terms of limited solubility of maleic anhydride in supercritical CO 2 . The solubility of maleic anhydride in supercritical carbon dioxide was directly measured by sampling and analyzing the supercritical phase. The observed sharp increase in the apparent rate constant of the reaction between maleic anhydride and isoprene correlates with the solubility of maleic anhydride in supercritical carbon dioxide. The interpretation was confirmed using visual observations of the phase behavior. The rate constant of the reaction measured under the true supercritical, single phase, conditions is k x ) (17.0 ( 1.3) hr -1 (mole fraction units, 60 °C, pressure 100 atm).

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Section: Methodsmentioning

confidence: 96%

Kinetics of a Diels−Alder Reaction of Maleic Anhydride and Isoprene in Supercritical CO₂

et al. 2001

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“…The authors also correlated the endo-to exo-selectivity with the transition energy, E,, for phenol blue, and then used this correlation to predict the selectivity in the near-critical region. Ikushima et al (1990Ikushima et al ( , 1992 reported kinetics data for the Diels-Alder addition of methyl acrylate to isoprene in SC CO, at 323 K and pressures between 4.9 and 20.6 MPa. The rate constant increased with pressure, and the selectivity to the two different adducts (methyl 4-methyl-3-cyclohexene-lcarboxylate and methyl 3-methyl-3-cyclohexene-1-carboxylate) was also pressure dependent.…”

Section: Diels-alder Reactionsmentioning

confidence: 99%

Reactions at supercritical conditions: Applications and fundamentals

et al. 1995

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“…[46] also examined rate constant data for two other DielsAlder reactions from the literature [41,431 in this manner and showed the same density dependence in COz. In their paper the relationship between the normalized mole fraction based rate constant (k,), normalized concentration based rate constant (k), Gibbs free energy of reaction (AG:), the continued product of activity coefficients ( q ) , and the transmission coefficient (K) was presented in the following expressions:…”

Section: Density Dependence Of the Bimolecular Rate Constantmentioning

confidence: 99%

Supercritical and Sub-Critical Fluid Solvent Effects on a Diels-Alder Reaction

Reaves

Roberts

1999

Chemical Engineering Communications

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The effect of pressure on the measured bimolecular rate constant of the Diets-Alder reaction between maleic anhydride and isoprene was investigated in supercritical C 0 2 and subsritical propane. The reaction was carried out at 35°C in C 0 2 and 80°C in propane. Measured bimolecular rate constants are also compared to predictions from the thermodynamic pressure effect using transition state theory and the Peng-Robinson equation of state. The rate constants in supercritical C 0 2 agreed closely with the thermodynamic pressure effect predictions over the entire pressure range. Furthermore, the mole fraction based rate constants were found to vary linearly with the density of the solution. The rate constants in the sub-critical propane solvent significantly diverged from the thermodynamic pressure effect predictions and were round to deviate from this linear density dependence at the lower pressures studied. The results are interpreted in the context of local reactant concentrations about the reacting maleic anhydride and solvent-solute and cosolvent-solute interactions.

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A Diels-Alder reaction in supercritical carbon dioxide medium.

Cited by 27 publications

References 4 publications

Kinetics of a Diels−Alder Reaction of Maleic Anhydride and Isoprene in Supercritical CO₂

Kinetics of a Diels−Alder Reaction of Maleic Anhydride and Isoprene in Supercritical CO₂

Reactions at supercritical conditions: Applications and fundamentals

Supercritical and Sub-Critical Fluid Solvent Effects on a Diels-Alder Reaction

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A Diels-Alder reaction in supercritical carbon dioxide medium.

Cited by 27 publications

References 4 publications

Kinetics of a Diels−Alder Reaction of Maleic Anhydride and Isoprene in Supercritical CO2

Kinetics of a Diels−Alder Reaction of Maleic Anhydride and Isoprene in Supercritical CO2

Reactions at supercritical conditions: Applications and fundamentals

Supercritical and Sub-Critical Fluid Solvent Effects on a Diels-Alder Reaction

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Product

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Kinetics of a Diels−Alder Reaction of Maleic Anhydride and Isoprene in Supercritical CO₂

Kinetics of a Diels−Alder Reaction of Maleic Anhydride and Isoprene in Supercritical CO₂