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Related Concept Videos

Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
Types of Step-Growth Polymers: Polyesters01:20

Types of Step-Growth Polymers: Polyesters

The introduction of polyesters has brought major development to the textile industry. The wrinkle-free behavior of polyester blends has eliminated the need for starching and ironing clothes.
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the polymer...
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,...
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

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Related Experiment Video

Updated: May 10, 2026

Synthesis of Soft Polysiloxane-urea Elastomers for Intraocular Lens Application
11:49

Synthesis of Soft Polysiloxane-urea Elastomers for Intraocular Lens Application

Published on: March 8, 2019

Polyurethanes from isosorbide-based diisocyanates.

Michael D Zenner1, Ying Xia, Jason S Chen

  • 1Department of Chemistry, Iowa State University, Ames, IA 50011, USA.

Chemsuschem
|June 13, 2013
PubMed
Summary
This summary is machine-generated.

Stereochemically pure diisocyanates were synthesized from biobased succinic anhydride and isosorbide or isomannide. Resulting polyurethanes exhibit excellent thermal stability and tunable properties, offering a sustainable alternative to petroleum-derived materials.

Keywords:
green chemistryisocyanatespolymersrearrangementrenewable resources

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Sustainable Materials Science

Background:

  • Polyurethanes are versatile polymers with widespread applications.
  • Traditional polyurethane synthesis often relies on petroleum-derived monomers, raising environmental concerns.
  • Developing sustainable and biobased alternatives is crucial for green chemistry.

Purpose of the Study:

  • To synthesize stereochemically pure diisocyanates from renewable resources.
  • To characterize the properties of polyurethanes derived from these novel diisocyanates.
  • To explore the impact of stereochemistry on polyurethane morphology and performance.

Main Methods:

  • Multigram-scale synthesis of diisocyanates using succinic anhydride and isosorbide or isomannide.
  • Polymerization of synthesized diisocyanates to form polyurethanes.
  • Characterization of polyurethanes using techniques to determine molecular weight (polydispersity), thermal stability, and morphology.

Main Results:

  • Stereochemically pure diisocyanates were successfully prepared on a multigram scale.
  • Polyurethanes derived from these diisocyanates showed low polydispersity and high thermal stability.
  • The morphology of the resulting polyurethanes was found to be dependent on the stereochemistry of the diisocyanate building blocks.
  • Utilizing biobased succinic anhydride eliminates the need for stoichiometric petroleum-derived reagents.

Conclusions:

  • Renewable, stereochemically pure diisocyanates can be synthesized efficiently.
  • These biobased diisocyanates yield high-performance polyurethanes with tunable properties.
  • This approach offers a sustainable pathway for producing advanced polyurethane materials, reducing reliance on fossil fuels.