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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Stability of Conjugated Dienes

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Introduction
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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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Rational design, synthesis and evaluation of new azido-ester structures as green energetic plasticizers.

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Evaluation of the Curing of Adhesive Systems by Rheological and Thermal Testing
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Simulation and experimental study on the incompatibility issue between ADN and isocyanate.

Nasser Sheibani1

  • 1Faculty of Chemistry and Chemical Engineering, Malek-Ashtar University of Technology, Tehran, Iran. nassersheibani@gmail.com.

Journal of Molecular Modeling
|November 30, 2022
PubMed
Summary

Researchers explored green propellants by examining isocyanate curing agents for ammonium dinitramide (ADN) and glycidyl azide polymer (GAP). A novel curing system showed significant improvements in ADN/GAP composite propellants, addressing incompatibility issues.

Keywords:
Ammonium dinitramide (ADN)Glycidyl azide polymer (GAP)Green energetic materialsMolecular dynamics (MD) simulations

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Area of Science:

  • Materials Science
  • Chemical Engineering
  • Propulsion Technology

Background:

  • Growing demand for eco-friendly solid composite propellants necessitates alternatives to ammonium perchlorate (AP).
  • Ammonium dinitramide (ADN) and glycidyl azide polymer (GAP) offer promising green propellant characteristics.
  • A key challenge is the incompatibility between ADN and conventional isocyanate curing agents in polyurethane binders.

Purpose of the Study:

  • To investigate molecular factors influencing the selection of optimal curing systems for ADN/GAP composite propellants.
  • To evaluate the interaction energy between various isocyanates and ADN/GAP.
  • To determine the differential reactivity of isocyanates with ADN using molecular dynamics and experimental methods.

Main Methods:

  • Molecular dynamics simulations and solubility parameter concepts were employed to analyze molecular interactions.
  • The reactivity of isocyanates (N100, IPDI, TDI, DDI, IPDI/N100, DDI/N100) with ADN was simulated and experimentally verified.
  • Infrared spectroscopy was used to assess the activity of selected curing systems with ADN over time, comparing them to N100.

Main Results:

  • Significant differences in reactivity rates were observed among various isocyanates when interacting with ADN.
  • The selected novel curing system demonstrated a meaningful improvement in the performance of ADN/GAP composite propellants.
  • Experimental validation confirmed the simulation findings regarding isocyanate activity.

Conclusions:

  • The study successfully identified molecular factors governing the compatibility of curing agents with ADN/GAP propellants.
  • A new curing system offers a viable solution to the ADN incompatibility problem, enhancing green propellant performance.
  • This research paves the way for developing more stable and efficient eco-friendly energetic materials.