Synthesis and characterization of new nitrogen-rich polymers as candidates for energetic applications

Mahkam, Mehrdad; Nabati, Mehdi; Latifpour, Abolfazl; Aboudi, Javad

doi:10.1080/15685551.2013.867569

Cited by 15 publications

(6 citation statements)

References 21 publications

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“…Mehrdad Mahkam reported the synthesis and tetrazole functionalization of PAN by free radical initiating process for the preparation of polymer electrolyte membranes . This was achieved through the free radical copolymerization of 4‐chloromethyl styrene (CMS) 69 with acrylonitrile 12 (in various mole ratios) at 70°C using AIBN as the initiator.…”

Section: Nitrile Group Modifications In Polymersmentioning

confidence: 99%

An overview of synthetic modification of nitrile group in polymers and applications

Sruthi

Anas

2020

Journal of Polymer Science

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The physicochemical properties of polymers are mainly dependent on the nature of polymer backbone and/or pendant groups linked to the main chain. Therefore, synthetic modification of these functional groups via post functionalization is an important approach for obtaining novel polymeric systems with improved properties and targeted applications. In this context, the synthetic modifications of nitrile group in polymers into various useful functionalities have received considerable attention and several interesting applications of the resulting polymers have been identified. The majority of the studies are based on Polyacrylonitrile (PAN), and some isolated examples of nitrile functionalization in copolymers such as Poly (Styrene-co-Acrylonitrile) (SAN), Poly (Acrylonitrile-co-Butadiene-co-Styrene (ABS) and Nitrile Rubber (NBR) are available. These synthetic modifications are mainly accomplished by the reactions such as Nucleophilic addition, cycloaddition, reduction, and hydrolysis using various reagents. These studies describing the post-polymerization modifications of nitrile group in polymers reported during the last three decades are covered in this review.

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Section: Nitrile Group Modifications In Polymersmentioning

confidence: 99%

An overview of synthetic modification of nitrile group in polymers and applications

Sruthi

Anas

2020

Journal of Polymer Science

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“…An environmentally benign, one-pot synthesis of 5-substituted 1H-tetrazoles in good yields ('nearly 80%') from aldehydes or ketones, malononitrile, and sodium azide via Knoevenagel condensation and 1,3-dipolar cycloaddition reactions under mild conditions without any catalyst in water was reported by Mahkam and co-workers (Scheme 39). 86 5-Substituted 1H-tetrazoles were synthesized in up to 98% yields by Coca and Turek 87 by reaction between aryl-, alkyl-, and vinyl-substituted nitriles with sodium azide using ytterbium triflate hydrate in DMF at 120-140 °C (Scheme 40). Substrates containing electron-withdrawing groups were more reactive than those containing electrondonating groups.…”

Section: Scheme 38 Zncl 2 -Catalyzed Synthesis In Aliphatic Alcoholsmentioning

confidence: 99%

Recent Advances in the Synthesis of 5-Substituted 1H-Tetrazoles: A Complete Survey (2013–2018)

Mittal¹,

Awasthi

2019

Synthesis

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Tetrazoles are synthetic organic heterocyclic compounds comprising of high nitrogen content among stable heterocycles. Tetrazoles, chiefly 5-substituted 1H-tetrazoles have been used as a bioisosteric replacement for carboxylic acids in medicinal chemistry. Various clinical drugs, including losartan, cefazolin, and alfentanil, contain the tetrazole moiety. There have been significant developments in the synthesis of 5-substituted 1H-tetrazoles. Researchers are still working to develop more efficient and ecofriendly methods for their synthesis. In this review, we provide a comprehensive discussion of the recent advancements in the field of synthesis of 5-substituted 1H-tetrazoles.1 Introduction2 The Role of 5-Substituted 1H-Tetrazoles in Medicinal Chemistry3 Synthesis of 5-Substituted 1H-Tetrazoles3.1 Microwave-Assisted Synthesis3.2 Heterogeneous Catalysts3.3 Nanoparticles as Heterogeneous Catalysts3.4 Miscellaneous Methods4 Sartans: A Class of Tetrazole-Based Commercial Drugs5 Conclusions

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“…In recent time, tetrazole heterocycles, among the series of explosophoric functional groups, have aroused considerable interest in the chemistry of high-energy materials, as well as in the development of energetic polymers [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ]. Tetrazoles are a unique class of high-nitrogen, aromatic molecular cages that combine a high positive heat of formation and density and good thermal stability, together with a low toxicity and susceptibility to mechanical stimuli [ 40 , 41 ].…”

Section: Introductionmentioning

confidence: 99%

“…High-molecular compounds functionalized by tetrazole derivatives demonstrate excellent energetic characteristics, high thermal stability and resistance to mechanical impacts—which makes them promising candidates for application in energetic formulations of different purposes [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ].…”

Section: Introductionmentioning

confidence: 99%

New 5-Aminotetrazole-Based Energetic Polymers: Synthesis, Structure and Properties

et al. 2022

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An N-glycidyl-5-aminotetrazole homopolymer was synthesized herein by nucleophilic substitution of 5-aminotetrazole heterocycles for chlorine atoms in poly-(epichlorohydrin)-butanediol. Copolymers of N-glycidyl-5-aminotetrazole and glycidyl azide with a varied ratio of energetic elements were synthesized by simultaneously reacting the 5-aminotetrazole sodium salt and the azide ion with the starting polymeric matrix. The 5-aminotetrazole-based homopolymer was nitrated to furnish a polymer whose macromolecule is enriched additionally with energy-rich terminal ONO2 groups and nitrate anions. The structures of the synthesized polymers were characterized by 1H and 13C NMR and IR spectroscopies, elemental analysis and gel-permeation chromatography. The densities were experimentally measured, and thermal stability data were acquired by differential scanning calorimetry. The insertion of aminotetrazole heterocycles into the polymeric chain and their modification via nitration provides an acceptable thermal stability and a considerable enhancement in density and nitrogen content compared to azide homopolymer GAP. By the 1.3-dipolar cycloaddition reaction, we demonstrated the conceptual possibility of preparing spatially branched, energy-rich polymeric binders bearing 5-aminotetrazole and 1,2,3-triazole heterocycles starting from the plasticized azide copolymers. The presence of the aforesaid advantages makes the reported polymers attractive candidates for use as a scaffold of energetic binders.

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Synthesis and characterization of new nitrogen-rich polymers as candidates for energetic applications

Cited by 15 publications

References 21 publications

An overview of synthetic modification of nitrile group in polymers and applications

An overview of synthetic modification of nitrile group in polymers and applications

Recent Advances in the Synthesis of 5-Substituted 1H-Tetrazoles: A Complete Survey (2013–2018)

New 5-Aminotetrazole-Based Energetic Polymers: Synthesis, Structure and Properties

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