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Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

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,...
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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 generated carbocation,...
Step-Growth Polymerization: Overview01:03

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Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...
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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Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.

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Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications
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1,4-Dioxane-2,5-dione-type monomers derived from l-ascorbic and d-isoascorbic acids. Synthesis and polymerisation.

Manuel Bueno1, Inmaculada Molina, Juan A Galbis

  • 1Departamento de Química Orgánica y Farmacéutica, Universidad de Sevilla, Spain.

Carbohydrate Research
|July 17, 2009
PubMed
Summary

Novel monomers derived from ascorbic acid were synthesized and polymerized. These new dioxane-dione polymers exhibit amorphous properties and thermal stability up to 250°C.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Ascorbic acid derivatives are valuable precursors for novel polymer synthesis.
  • 1,4-dioxane-2,5-dione monomers offer unique structural possibilities for biodegradable polymers.

Purpose of the Study:

  • To synthesize novel 1,4-dioxane-2,5-dione monomers from l-ascorbic and d-isoascorbic acids.
  • To investigate the ring-opening polymerization of a novel monomer, IPTA, derived from l-ascorbic acid.
  • To characterize the resulting polymers for their molecular weight and thermal properties.

Main Methods:

  • Synthesis of three novel monomers: IPTA, IPTP, and IPEA.
  • Ring-opening homopolymerization and copolymerization of IPTA with d,l-lactide.
  • Polymer characterization using elemental microanalysis, IR, 1H and 13C NMR spectroscopies, GPC, DSC, and TGA.

Main Results:

  • Successful preparation of three novel 1,4-dioxane-2,5-dione monomers.
  • Homopolymerization and copolymerization of IPTA yielded polymers with varying molecular weights.
  • All synthesized polymers were found to be amorphous and thermally stable up to 250°C under nitrogen.

Conclusions:

  • Novel ascorbic acid-derived dioxane-dione monomers can be synthesized and polymerized.
  • The resulting polymers possess amorphous characteristics and good thermal stability.
  • These findings open avenues for developing new functional biodegradable polymers.