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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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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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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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Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
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Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
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Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization
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Nitriles as Functionalization and Coupling Agents for Polyolefins Obtained by Coordinative Chain Transfer

Ariane Desgranges1,2, François Jean-Baptiste-Dit-Dominique2, Robert Ngo2

  • 1Universite Claude Bernard Lyon 1, CPE Lyon, CNRS UMR 5128, Laboratoire CP2M, Equipe PCM, Villeurbanne, 69616, France.

Macromolecular Rapid Communications
|June 5, 2024
PubMed
Summary

This study demonstrates coordinative chain transfer polymerization of ethylene and butadiene using a neodymium complex and organomagnesium agents. Functionalized polymers, including ketone-terminated chains and coupled products, were successfully synthesized.

Keywords:
CCTPGrignard reagentmetallocenenitrilepolymerization

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Area of Science:

  • Polymer Chemistry
  • Organometallic Chemistry
  • Catalysis

Background:

  • Coordinative chain transfer polymerization (CCTP) offers precise control over polymer molecular weight and architecture.
  • Neodymium-based catalysts are effective for olefin polymerization, but control over chain transfer and functionalization requires further investigation.
  • Organomagnesium compounds are known chain transfer agents, but their role in CCTP with rare-earth metal catalysts needs detailed study.

Purpose of the Study:

  • To investigate the coordinative chain transfer polymerization (CCTP) of ethylene and its copolymerization with 1,3-butadiene using a specific neodymium complex.
  • To evaluate the influence of various organomagnesium compounds as chain transfer agents on polymerization kinetics and control.
  • To achieve functionalization of polymer chains, specifically ketone end-groups, and explore coupling strategies.

Main Methods:

  • Ethylene and 1,3-butadiene polymerization conducted in toluene at 80 °C.
  • Utilized a neodymium complex {(Me2Si(C13H8)2)Nd(μ-BH4)[(μ-BH4)Li(THF)]}2 (1) in combination with diverse organomagnesium compounds (BOMAG, n-BuMgMes, n-BuMgCl, n-C5H11MgBr, PDMB, i-BuMgCl).
  • Post-polymerization functionalization via deactivation with benzonitrile or methoxybenzonitrile, and coupling using dinitrile reagents.

Main Results:

  • Comparative analysis of polymerization kinetics and control based on the type of organomagnesium agent and presence of ether.
  • Successful synthesis of ketone ω-functionalized polymer chains through nitrile deactivation.
  • Demonstrated functionalization and coupling of high molar mass ethylene butadiene rubber (EBR).

Conclusions:

  • The neodymium-based CCTP system provides effective control over ethylene and butadiene polymerization.
  • Organomagnesium compounds play a crucial role as chain transfer agents, influencing polymerization performance.
  • The developed method enables versatile functionalization and coupling of polyolefins, expanding their application potential.