KFU. Card publication. Treatment of Substandard Rocket Fuel 1,1-Dimethylhydrazine via Its Methylene Derivative into Heterocycles Based on Pyrrolo-[3,4c]Quinolines, Cyclododeca[b]piran and Pyrrole

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TREATMENT OF SUBSTANDARD ROCKET FUEL 1,1-DIMETHYLHYDRAZINE VIA ITS METHYLENE DERIVATIVE INTO HETEROCYCLES BASED ON PYRROLO-[3,4C]QUINOLINES, CYCLODODECA[B]PIRAN AND PYRROLE

Form of presentation

Articles in international journals and collections

Year of publication

2023

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Authors, employees of KFU

Grishaev Denis Yurevich, author

Other authors

Andreeva Vera Vladimirovna, author

Vasileva Tatyana Vasilevna, author

Eryomkin Aleksey Vladimirovich, author

Ivanova Elizaveta Sergeevna, author

Lodochnikova Olga Aleksandrovna, author

Maryasov Maksim Aleksandrovich, author

Nasakin Oleg Evgenevich, author

Osipova Margarita Petrovna, author

Bibliographic description in the original language

Ivanova E. Treatment of Substandard Rocket Fuel 1,1-Dimethylhydrazine via Its Methylene Derivative into Heterocycles Based on Pyrrolo-[3,4c]Quinolines, Cyclododeca[b]piran and Pyrrole / E.Ivanova ,M. Maryasov ,V.Andreeva ,M.Osipova ,T. Vasilieva ,A.Eremkin, O. Lodochnikova, D. Grishaev , O. E. Nasakin // Int. J. Mol. Sci. - 2023. - Volume 24 - Issue 17.-Pages 13076

Annotation

1,1-Dimethylhydrazine (Heptil, rocket fuel (UDMH)) is characterized by extremely high toxicity, teratogenicity and the ability to constantly absorb water from the atmosphere, losing its energy characteristics. In this regard, as well as due to the alternative fuel (“Angara”) transition, there is a need for UDMH utilization in huge amounts. A more benign approach involves its immediate reaction with a formalin solution to form 1,1–dimethyl-2-methylene hydrazone (MDH), which is significantly less toxic by an order of magnitude. MDH can then be polymerized under acidic conditions, and the resulting product can be burned, yielding a substantial amount of nitrogen oxides. We propose an alternative to incineration by involving MDH in organic synthesis. We studied the reactions of MDH and its analog N,N-dimethyl-2-(methylenamino)ethane-1-amine (MDEA) with available CH-acids: tetracyanoethylated ketones (TCEKs) based on cyclohexanone, 4-propylcyclohexanone, 2-methylcyclohexanone, cyclododecanone and tetracyanoethane. The structures synthesized were confirmed by IR, 1H, 13C NMR and mass spectroscopy methods. MDH-based adducts were also identified by X-ray structural analysis. TCEKs and MDH, as well as TCEK based on cyclohexanone and MDEA, form bi- and tricyclic structures: pyrrolo [3,4c]-quinolines (using TCEKs based on cyclohexanone and 4-propylcyclohexanone), epiminomethanoquinoline-3,4-dicarbonitrile (using TCEK based on 2-methylcyclohexanone) and cyclododec[b]pyran-3,4-dicarbonitrile (using TCEK based on cyclododecanone). MDH and TCNEH2 formed a pyrrole derivative. Thus, we synthesized the structures that are of interest for molecular design and pharmaceutical chemistry.

Keywords

unsymmetrical dimethylhydrazine; methylene dimethylhydrazone; tetracyanoethylene; tetracyanoketones

The name of the journal

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES

On-line resource for training course

http://dspace.kpfu.ru/xmlui/bitstream/handle/net/183411/F_1.pdf?sequence=1&isAllowed=y

URL

https://www.mdpi.com/1422-0067/24/17/13076

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=297678&p_lang=2

Resource files

File name	Size (MB)	Format
F_1.pdf	8,58	pdf	show / download

Full metadata record

Field DC	Value	Language
dc.contributor.author	Grishaev Denis Yurevich	ru_RU
dc.contributor.author	Andreeva Vera Vladimirovna	ru_RU
dc.contributor.author	Vasileva Tatyana Vasilevna	ru_RU
dc.contributor.author	Eryomkin Aleksey Vladimirovich	ru_RU
dc.contributor.author	Ivanova Elizaveta Sergeevna	ru_RU
dc.contributor.author	Lodochnikova Olga Aleksandrovna	ru_RU
dc.contributor.author	Maryasov Maksim Aleksandrovich	ru_RU
dc.contributor.author	Nasakin Oleg Evgenevich	ru_RU
dc.contributor.author	Osipova Margarita Petrovna	ru_RU
dc.date.accessioned	2023-01-01T00:00:00Z	ru_RU
dc.date.available	2023-01-01T00:00:00Z	ru_RU
dc.date.issued	2023	ru_RU
dc.identifier.citation	Ivanova E. Treatment of Substandard Rocket Fuel 1,1-Dimethylhydrazine via Its Methylene Derivative into Heterocycles Based on Pyrrolo-[3,4c]Quinolines, Cyclododeca[b]piran and Pyrrole / E.Ivanova ,M. Maryasov ,V.Andreeva ,M.Osipova ,T. Vasilieva ,A.Eremkin, O. Lodochnikova, D. Grishaev , O. E. Nasakin // Int. J. Mol. Sci. - 2023. - Volume 24 - Issue 17.-Pages 13076	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/eng/?p_id=297678&p_lang=2	ru_RU
dc.description.abstract	INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES	ru_RU
dc.description.abstract	1,1-Dimethylhydrazine (Heptil, rocket fuel (UDMH)) is characterized by extremely high toxicity, teratogenicity and the ability to constantly absorb water from the atmosphere, losing its energy characteristics. In this regard, as well as due to the alternative fuel (“Angara”) transition, there is a need for UDMH utilization in huge amounts. A more benign approach involves its immediate reaction with a formalin solution to form 1,1–dimethyl-2-methylene hydrazone (MDH), which is significantly less toxic by an order of magnitude. MDH can then be polymerized under acidic conditions, and the resulting product can be burned, yielding a substantial amount of nitrogen oxides. We propose an alternative to incineration by involving MDH in organic synthesis. We studied the reactions of MDH and its analog N,N-dimethyl-2-(methylenamino)ethane-1-amine (MDEA) with available CH-acids: tetracyanoethylated ketones (TCEKs) based on cyclohexanone, 4-propylcyclohexanone, 2-methylcyclohexanone, cyclododecanone and tetracyanoethane. The structures synthesized were confirmed by IR, 1H, 13C NMR and mass spectroscopy methods. MDH-based adducts were also identified by X-ray structural analysis. TCEKs and MDH, as well as TCEK based on cyclohexanone and MDEA, form bi- and tricyclic structures: pyrrolo [3,4c]-quinolines (using TCEKs based on cyclohexanone and 4-propylcyclohexanone), epiminomethanoquinoline-3,4-dicarbonitrile (using TCEK based on 2-methylcyclohexanone) and cyclododec[b]pyran-3,4-dicarbonitrile (using TCEK based on cyclododecanone). MDH and TCNEH2 formed a pyrrole derivative. Thus, we synthesized the structures that are of interest for molecular design and pharmaceutical chemistry.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject		ru_RU
dc.title	Treatment of Substandard Rocket Fuel 1,1-Dimethylhydrazine via Its Methylene Derivative into Heterocycles Based on Pyrrolo-[3,4c]Quinolines, Cyclododeca[b]piran and Pyrrole	ru_RU
dc.type	Articles in international journals and collections	ru_RU