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Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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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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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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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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Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
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Sharpless Epoxidation02:57

Sharpless Epoxidation

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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Nature-Derived Epoxy Resin Monomers with Reduced Sensitizing Capacity─Isosorbide-Based Bis-Epoxides.

Isabella Karlsson1, David J Ponting2, Miguel A Ortega2

  • 1Department of Environmental Science, Exposure and Effect, Stockholm University, SE-106 91Stockholm, Sweden.

Chemical Research in Toxicology
|January 18, 2023
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Summary

Researchers developed new, renewable epoxy resin monomers from isosorbide as safer alternatives to diglycidyl ether of bisphenol A (DGEBA). These isosorbide derivatives show significantly reduced skin sensitization potential and promising technical properties for various applications.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Green Chemistry

Background:

  • Epoxy resin systems (ERSs) are crucial thermosetting polymers used in coatings, adhesives, and composites.
  • The dominant epoxy resin monomer, diglycidyl ether of bisphenol A (DGEBA), is a potent skin sensitizer and derived from endocrine-disruptive bisphenol A (BPA).
  • There is a growing need for safer, sustainable alternatives to DGEBA in the plastics industry.

Purpose of the Study:

  • To synthesize and evaluate novel, renewable isosorbide-based bis-epoxides as potential replacements for DGEBA.
  • To assess the skin sensitization potential and reactivity of these new monomers.
  • To conduct preliminary investigations into the technical properties of polymers derived from these isosorbide derivatives.

Main Methods:

  • Synthesis of three isosorbide-based bis-epoxides: diglycidyl ether of isosorbide (1), and two novel derivatives (2, 3) with ester or ether linkages.
  • In vivo assessment of skin sensitization using the murine local lymph node assay (LLNA).
  • In vitro peptide reactivity assays and ex vivo skin permeation studies using pig skin and Franz cells.

Main Results:

  • All synthesized isosorbide bis-epoxides demonstrated significantly lower skin sensitization potency compared to DGEBA in the LLNA.
  • Compound 2 exhibited the lowest sensitization and peptide reactivity, showing no sensitization at 25% w/v.
  • Preliminary polymer characterization indicated promising technical properties for the new isosorbide-based resins.

Conclusions:

  • Isosorbide-based bis-epoxides represent a viable, less sensitizing, and renewable alternative to DGEBA.
  • Compound 2, with its benzoic ester linkage, shows particular promise as a safer epoxy resin monomer.
  • Further research into the technical properties of these novel polymers is warranted for commercial application.