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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Cationic Chain-Growth Polymerization: Mechanism00:57

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Bio-Catechol Electro-Reforming promovido por la coordinación hacia la producción sostenible de polímeros

Ran Wang1, Chong Li2, Jianxiang Wu1

  • 1Department of Chemistry and Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai 200438, China.

Journal of the American Chemical Society
|July 28, 2023
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Resumen

El ácido cis-mucónico derivado de la biomasa ofrece una vía sostenible hacia los polímeros. El catecol electro-reformado utilizando iones de zinc y un electrodo de espuma de CuO logra altos rendimientos de este químico clave y hidrógeno.

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Área de la Ciencia:

  • La electroquímica
  • Química ecológica
  • Ciencia de los Polímeros

Sus antecedentes:

  • La producción sostenible de polímeros es crucial para un futuro neutro en carbono.
  • El ácido cis-mucónico derivado de la biomasa es una molécula de plataforma clave para el ácido adípico y el ácido tereftálico, monómeros poliméricos esenciales.
  • Los métodos actuales para la producción de ácido mucónico a menudo implican condiciones adversas o carecen de sostenibilidad.

Objetivo del estudio:

  • Desarrollar un proceso de electro-reforma sostenible y eficiente para convertir el catecol biorrenovable en ácido cis-mucónico.
  • Investigar el papel de la coordinación de iones de zinc en la mejora del rendimiento y la selectividad de la reacción de electrooxidación.
  • Demostrar un sistema práctico de dos electrodos para la producción simultánea de ácido cis, cis-mucónico e hidrógeno.

Principales métodos:

  • Oxidación electroquímica del catecol utilizando un electrodo de espuma de CuO en condiciones ambientales.
  • Espectroscopia in situ, cinética electroquímica de estado estacionario y cálculos teóricos para dilucidar los mecanismos de reacción.
  • Utilizando la coordinación Zn2+ para controlar las vías de electrooxidación del catecol.

Principales resultados:

  • Se obtiene un alto rendimiento de cis, cis-muconato del 90% y una eficiencia faradaica del 87% sin oxidantes externos.
  • Se demostró que la coordinación Zn2+ suprime efectivamente la polimerización y promueve la escisión del anillo, mejorando la selectividad de los muconatos.
  • Un sistema práctico de dos electrodos produjo con éxito ácido cis, cis-mucónico y hidrógeno aislables.

Conclusiones:

  • El proceso de electro-reformación propuesto ofrece un método sostenible y eficiente para la producción de ácido cis-mucónico a partir de catecol derivado de la biomasa.
  • La coordinación Zn2+ juega un papel crítico en la dirección de la vía de electrooxidación hacia el producto deseado de ácido mucónico.
  • Este enfoque proporciona una solución viable para la producción sostenible de polímeros mediante la utilización de recursos alternativos de biomasa y procesos electrificados.