Synthesis of functionalized by an oxime group surfactants on the basis of imidazole, pyridine and alkylamines
Methods have been developed for the synthe-sis of a series of monomeric and dimeric surfactants functionalized by an oxime group based on imid-azole, pyridine and alkylamines. Alkyl radicals of varying degrees of branching were used, both as sub-stituents at the nitrogen atom of the head group and a...
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| Дата: | 2019 |
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| Автори: | , , , , , |
| Формат: | Стаття |
| Мова: | Англійська |
| Опубліковано: |
V.I.Vernadsky Institute of General and Inorganic Chemistry
2019
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| Онлайн доступ: | https://ucj.org.ua/index.php/journal/article/view/76 |
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| Назва журналу: | Ukrainian Chemistry Journal |
Репозитарії
Ukrainian Chemistry Journal| _version_ | 1856543744193462272 |
|---|---|
| author | Shumeiko, Alexander Kostrikin, Michael Kapitanov, Ilya Serdyuk, Anna Burakov, Nikolay Popov, Anatoly |
| author_facet | Shumeiko, Alexander Kostrikin, Michael Kapitanov, Ilya Serdyuk, Anna Burakov, Nikolay Popov, Anatoly |
| author_sort | Shumeiko, Alexander |
| baseUrl_str | |
| collection | OJS |
| datestamp_date | 2019-12-21T01:29:46Z |
| description | Methods have been developed for the synthe-sis of a series of monomeric and dimeric surfactants functionalized by an oxime group based on imid-azole, pyridine and alkylamines. Alkyl radicals of varying degrees of branching were used, both as sub-stituents at the nitrogen atom of the head group and as spacers in the formation of dimeric products. This allowed to create a whole spectrum of supramo-lecular systems with different physicochemical pro-perties and reactivity.Methods of obtaining a number of intermedi-ate products were improved, primarily for the reac-tion of the imidazole alkylation using interphase ca-talysis conditons — solid phase-liquid. The method of obtaining surfactants based on imidazole consisted in the interaction of alkylimidazoles with chloro-acetaloxime in a suitable solvent or with chloro-acetone and subsequent reaction with a hydroxyla-mine solution. In the preparation of pyridine-based surfactants, the corresponding oxo-substituted pyri-dine was reacted with a hydroxylamine solution, fol-lowed by reaction of the obtained product with al-kyl halide. A method has been developed for the syn-thesis of functionalized surfactants based on alipha-tic amines, where for monomeric products a path is chosen that is associated with the sequential alkyla-tion of 1-chloroacetoxime with dimethylamine and dodecyl bromide, and for dimeric ones, the direct interaction of 1,3-dichloroacetoxime with 1,1-dime-thyl-1-dodecylamine.The composition, structure and purity of the obtained compounds were confirmed by NMR spec-troscopy, thin-layer chromatography and elemental analysis. NMR spectra were recorded on a BRUKER Avance II 400 instrument (400 MHz), TMS was used as an internal standard. Chromatography in a thin layer of silica gel was performed on Merck Si-licaGel 60 F254 plates (eluent — chloroform: meth-anol = 10:1).The data presented by us testify to the pro-spects of the chosen pathway for structural modifica-tion of surfactants functionalized by the oxime group, and give direction for the further design of such microheterogeneous systems. |
| first_indexed | 2025-09-24T17:43:32Z |
| format | Article |
| id | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-76 |
| institution | Ukrainian Chemistry Journal |
| language | English |
| last_indexed | 2025-09-24T17:43:32Z |
| publishDate | 2019 |
| publisher | V.I.Vernadsky Institute of General and Inorganic Chemistry |
| record_format | ojs |
| spelling | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-762019-12-21T01:29:46Z Synthesis of functionalized by an oxime group surfactants on the basis of imidazole, pyridine and alkylamines СИНТЕЗ ФУНКЦИОНАЛИЗИРОВАННЫХ ОКСИМНЫМИ ГРУППАМИ ПАВ НА ОСНОВЕ ИМИДАЗОЛА, ПИРИДИНА И АЛКИЛАМИНОВ Shumeiko, Alexander Kostrikin, Michael Kapitanov, Ilya Serdyuk, Anna Burakov, Nikolay Popov, Anatoly functionalized surfactants, oximes, salts of pyridinium imidazolium, tetraalkylammonium. Methods have been developed for the synthe-sis of a series of monomeric and dimeric surfactants functionalized by an oxime group based on imid-azole, pyridine and alkylamines. Alkyl radicals of varying degrees of branching were used, both as sub-stituents at the nitrogen atom of the head group and as spacers in the formation of dimeric products. This allowed to create a whole spectrum of supramo-lecular systems with different physicochemical pro-perties and reactivity.Methods of obtaining a number of intermedi-ate products were improved, primarily for the reac-tion of the imidazole alkylation using interphase ca-talysis conditons — solid phase-liquid. The method of obtaining surfactants based on imidazole consisted in the interaction of alkylimidazoles with chloro-acetaloxime in a suitable solvent or with chloro-acetone and subsequent reaction with a hydroxyla-mine solution. In the preparation of pyridine-based surfactants, the corresponding oxo-substituted pyri-dine was reacted with a hydroxylamine solution, fol-lowed by reaction of the obtained product with al-kyl halide. A method has been developed for the syn-thesis of functionalized surfactants based on alipha-tic amines, where for monomeric products a path is chosen that is associated with the sequential alkyla-tion of 1-chloroacetoxime with dimethylamine and dodecyl bromide, and for dimeric ones, the direct interaction of 1,3-dichloroacetoxime with 1,1-dime-thyl-1-dodecylamine.The composition, structure and purity of the obtained compounds were confirmed by NMR spec-troscopy, thin-layer chromatography and elemental analysis. NMR spectra were recorded on a BRUKER Avance II 400 instrument (400 MHz), TMS was used as an internal standard. Chromatography in a thin layer of silica gel was performed on Merck Si-licaGel 60 F254 plates (eluent — chloroform: meth-anol = 10:1).The data presented by us testify to the pro-spects of the chosen pathway for structural modifica-tion of surfactants functionalized by the oxime group, and give direction for the further design of such microheterogeneous systems. V.I.Vernadsky Institute of General and Inorganic Chemistry 2019-08-15 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/76 10.33609/0041-6045.85.8.2019.94-105 Ukrainian Chemistry Journal; Vol. 85 No. 8 (2019): Ukrainian Chemistry Journal; 94-105 Украинский химический журнал; Том 85 № 8 (2019): Украинский химический журнал; 94-105 Український хімічний журнал; Том 85 № 8 (2019): Український хімічний журнал; 94-105 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/76/50 |
| spellingShingle | Shumeiko, Alexander Kostrikin, Michael Kapitanov, Ilya Serdyuk, Anna Burakov, Nikolay Popov, Anatoly Synthesis of functionalized by an oxime group surfactants on the basis of imidazole, pyridine and alkylamines |
| title | Synthesis of functionalized by an oxime group surfactants on the basis of imidazole, pyridine and alkylamines |
| title_alt | СИНТЕЗ ФУНКЦИОНАЛИЗИРОВАННЫХ ОКСИМНЫМИ ГРУППАМИ ПАВ НА ОСНОВЕ ИМИДАЗОЛА, ПИРИДИНА И АЛКИЛАМИНОВ |
| title_full | Synthesis of functionalized by an oxime group surfactants on the basis of imidazole, pyridine and alkylamines |
| title_fullStr | Synthesis of functionalized by an oxime group surfactants on the basis of imidazole, pyridine and alkylamines |
| title_full_unstemmed | Synthesis of functionalized by an oxime group surfactants on the basis of imidazole, pyridine and alkylamines |
| title_short | Synthesis of functionalized by an oxime group surfactants on the basis of imidazole, pyridine and alkylamines |
| title_sort | synthesis of functionalized by an oxime group surfactants on the basis of imidazole, pyridine and alkylamines |
| topic_facet | functionalized surfactants oximes salts of pyridinium imidazolium tetraalkylammonium. |
| url | https://ucj.org.ua/index.php/journal/article/view/76 |
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