scholarly journals Continuous flow synthesis of terpene-based monomers for green polymers production

2019 ◽  
Author(s):  
Lucas Pera Fernandes ◽  
Julio Cezar Pastre ◽  
Renan Galaverna ◽  
Gustavo Rodrigues Gomes
Keyword(s):  
Maleic Anhydride ◽  
Flow Regime ◽  
Continuous Flow ◽  
Cycloaddition Reaction ◽  
Hydrogenation Reaction ◽  
Diels Alder ◽  
Flow Conditions ◽  
Flow Synthesis ◽  
Green Polymers

The synthesis of monomers for the production of novel green polymers was evaluated in continuous flow conditions using terpenes as dienes and maleic anhydride as dienophile for the [4+2] Diels-Alder cycloaddition reaction. The hydrogenation reaction was also evaluated to prevent the retro-Diels-Alder and to expand the reactional scope by producing adducts with distinct characteristics of structures and reactivity. Fourteen different monomers were obtained in good yields in flow regime.

Stereoselective DielsAlder Reactions Promoted under Continuous-Flow Conditions by Silica-Supported Chiral Organocatalysts

2014 ◽  
Vol 54 (4) ◽  
pp. 381-394 ◽  
Author(s):  
Riccardo Porta ◽  
Maurizio Benaglia ◽  
Valerio Chiroli ◽  
Francesca Coccia ◽  
Alessandra Puglisi
Keyword(s):  
Continuous Flow ◽  
Diels Alder ◽  
Flow Conditions

scholarly journals p-Xylene from 2,5-dimethylfuran and acrylic acid using zeolite in a continuous flow system

2020 ◽  
Vol 22 (21) ◽  
pp. 7398-7405 ◽  
Author(s):  
Jose Alirio Mendoza Mesa ◽  
Francesco Brandi ◽  
Irina Shekova ◽  
Markus Antonietti ◽  
Majd Al-Naji
Keyword(s):  
Acrylic Acid ◽  
Lignocellulosic Biomass ◽  
Continuous Flow ◽  
Flow System ◽  
Diels Alder ◽  
Flow Synthesis ◽  
Continuous Flow System ◽  
System P ◽  
Different Types

The continuous flow synthesis of p-xylene (pXL) via Diels–Alder cycloaddition of lignocellulosic biomass-derivable 2,5-dimethylfuran (DMF) and acrylic acid (AA) was performed over different types of zeolites.

Continuous Flow Synthesis of Dimethylalkynylaluminum Reagents

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3272-3278 ◽  
Author(s):  
Riccardo Piccardi ◽  
Anais Coffinet ◽  
Erica Benedetti ◽  
Serge Turcaud ◽  
Laurent Micouin
Keyword(s):  
Continuous Flow ◽  
Terminal Alkynes ◽  
Flow Conditions ◽  
Flow Synthesis ◽  
New Process

A new process for the synthesis of dimethylalkynylaluminum reagents under flow conditions is described. It involves a base-catalyzed alumination of terminal alkynes using a resin-supported organocatalyst. Final organometallic species are obtained in solution, and can further react with various aldehydes or nitrones.

ChemInform Abstract: Stereoselective Diels-Alder Reactions Promoted under Continuous-Flow Conditions by Silica-Supported Chiral Organocatalysts

ChemInform ◽  
2014 ◽  
Vol 45 (40) ◽  
pp. no-no
Author(s):  
Riccardo Porta ◽  
Maurizio Benaglia ◽  
Valerio Chiroli ◽  
Francesca Coccia ◽  
Alessandra Puglisi
Keyword(s):  
Continuous Flow ◽  
Diels Alder ◽  
Flow Conditions

scholarly journals The Role of Supramolecular Intermediates in the Potential Energy Surface of the Diels-Alder Reaction

2017 ◽  
Vol 57 (4) ◽  
Author(s):  
Karla Ramírez-Gualito ◽  
Néstor López-Mora ◽  
Hugo A. Jiménez-Vázquez ◽  
Joaquín Tamariz ◽  
Gabriel Cuevas
Keyword(s):  
Maleic Anhydride ◽  
Potential Energy ◽  
Potential Energy Surface ◽  
Energy Surface ◽  
Van Der Waals ◽  
Cycloaddition Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Electrostatic Phenomena

The potential energy surface of four stereoselective Diels-Alder reactions was studied, namely: cyclopentadiene-maleic anhydride, furan-maleic anhydride, the dimerization of cyclopentadiene, and cyclopentadiene-cyclopropene. For completeness, we also studied the reaction between ethylene and 2-hydroxy-6-methyl-1,4-benzoquinone, a [5+2] cycloaddition reaction. For all cases at least a stationary state of supramolecular nature a van der Waals complex, was determined. These stationary states are complexes formed by the interaction between the reagents, minima located in the paths between the non-interacting molecules and the transition states. The existence of these complexes makes it necessary to reconsider the role of Secondary Orbital Interactions in the selectivity of these reactions. As it is the case with other complexes, the stability of these supramolecular intermediates depends on electrostatic phenomena such as dispersion forces. The observation of [5+2] intramolecular complexes in solution is important since up to now, this kind of van der Waals complexes had only been described in the gas phase.

On the Solvent and Temperature Driven Stereoselectivity of the Diels-Alder Cycloaddition Reactions of Furan with Maleic Anhydride and Maleimide

2019 ◽  
Author(s):  
Veejendra Yadav ◽  
Dasari L V K Prasad ◽  
Arpita Yadav ◽  
Kedar Yadav
Keyword(s):  
Free Energy ◽  
Maleic Anhydride ◽  
Gas Phase ◽  
Quantum Chemical ◽  
Room Temperature ◽  
Experimental Studies ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Endo Isomer ◽  
Equilibrium Process

In quantum chemical calculations, the Diels-Alder cycloaddition reaction of maleic anhydride with furan favors the endo-isomer kinetically in the gas phase. This preference, however, changes in favor of the exo-isomer on inclusion of solvent effects. For example, in acetonitrile, the exo-isomer was calculated to form twice as fast as the endo-isomer at room temperature, an observation that corroborates well with the experiments. The free energy change of the reaction is such that it allows faster reversal of the endo-isomer to the reactants in an equilibrium process and, thus, the predominance of the more stable exo-isomer eventually. The reaction of maleimide with furan is similar to that of maleic anhydride. However, it favors predominantly endo selectivity at temperatures below 320 K which is in excellent agreement with the experimental studies of temperature dependence of this DA reaction. Further, a gedanken calculation of the DA reaction of cyclopropene with furan has been investigated to delineate the effect of the retro-pathway on the stereoselectivity.

scholarly journals Continuous flow processing as a tool for the generation of terpene-derived monomer libraries

2019 ◽  
Vol 4 (2) ◽  
pp. 362-367 ◽  
Author(s):  
Renan Galaverna ◽  
Lucas P. Fernandes ◽  
Duncan L. Browne ◽  
Julio C. Pastre
Keyword(s):  
Continuous Flow ◽  
Alder Reaction ◽  
Diels Alder ◽  
Flow Conditions ◽  
Rapid Synthesis ◽  
Diels Alder Reaction

A Diels–Alder reaction employing terpenes for rapid synthesis of monomer libraries under flow conditions is presented.

On the Solvent and Temperature Driven Stereoselectivity of the Diels-Alder Cycloaddition Reactions of Furan with Maleic Anhydride and Maleimide

2019 ◽  
Author(s):  
Veejendra Yadav ◽  
Dasari L V K Prasad ◽  
Arpita Yadav ◽  
Kedar Yadav
Keyword(s):  
Free Energy ◽  
Maleic Anhydride ◽  
Gas Phase ◽  
Quantum Chemical ◽  
Room Temperature ◽  
Experimental Studies ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Endo Isomer ◽  
Equilibrium Process

In quantum chemical calculations, the Diels-Alder cycloaddition reaction of maleic anhydride with furan favors the endo-isomer kinetically in the gas phase. This preference, however, changes in favor of the exo-isomer on inclusion of solvent effects. For example, in acetonitrile, the exo-isomer was calculated to form twice as fast as the endo-isomer at room temperature, an observation that corroborates well with the experiments. The free energy change of the reaction is such that it allows faster reversal of the endo-isomer to the reactants in an equilibrium process and, thus, the predominance of the more stable exo-isomer eventually. The reaction of maleimide with furan is similar to that of maleic anhydride. However, it favors predominantly endo selectivity at temperatures below 320 K which is in excellent agreement with the experimental studies of temperature dependence of this DA reaction. Further, a gedanken calculation of the DA reaction of cyclopropene with furan has been investigated to delineate the effect of the retro-pathway on the stereoselectivity.

Sign in / Sign up

Export Citation Format

Share Document