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Base-Catalyzed Ring-Opening of Epoxides02:26

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
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Base-Mediated Depolymerization of Amine-Cured Epoxy Resins.

Rebecca C DiPucchio1, Katherine R Stevenson1, Ciaran W Lahive1

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ACS Sustainable Chemistry & Engineering
|December 11, 2023
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Summary
This summary is machine-generated.

Researchers developed a new recycling method for carbon fiber composites, focusing on recovering epoxy monomers. This potassium tert-butoxide process efficiently breaks down epoxy resins, yielding valuable phenol and amine products for reuse.

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Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Sustainable Chemistry

Background:

  • Carbon fiber-reinforced epoxy composites offer high performance but pose recycling challenges.
  • Current recycling primarily focuses on fiber recovery, neglecting valuable epoxy components.
  • Developing efficient methods for epoxy monomer recovery is crucial for circular economy approaches.

Purpose of the Study:

  • To investigate the cleavage of C-O and C-N bonds in amine-cured epoxy resins using potassium tert-butoxide.
  • To develop a recycling strategy for recovering both epoxy monomers and fibers from composite materials.
  • To assess the efficiency of this method using model compounds and a commercial epoxy thermoset.

Main Methods:

  • Utilized potassium tert-butoxide to mediate the cleavage of C-O and C-N bonds in epoxy resins.
  • Employed model compounds representing C-O and C-N linkages in amine-cured composites.
  • Expanded the method to model linear thermoplastics and thermoset substrates.

Main Results:

  • Achieved high yields of phenol (up to 97% molar) and amine products (up to 99 mol %) from model compounds.
  • Obtained quantitative yields of bisphenol A (BPA) from model thermoplastic epoxy amines.
  • Recovered 71% molar yield of BPA from a commercial epoxy thermoset, representing 15% mass recovery.

Conclusions:

  • Potassium tert-butoxide mediated cleavage is an effective method for recycling amine-cured epoxy resins.
  • This approach enables the recovery of valuable epoxy monomers like phenol, amines, and BPA.
  • The developed strategy offers a promising pathway towards more sustainable recycling of carbon fiber composites.