New heat-resistant porous polymer sorbents – polynaphthalenebenzimidazoles for gas chromatographic separation and concentration of volatile substances
Abstract
The results of a study of polymers of polynaphthylenebenzimidazoles synthesized by the interaction of 1,4,5,8-naphthalene tetracarboxylic acid dianhydride with 3, 3' ,4, 4'- tetraaminodiphenyloxide (PNBI-1), 3, 3', 4, 4'- tetraaminodiphenyl (PNBI-2), 3, 3', 4,4',-tetraaminodiphenylsulfone (PNBI-3) and 3, 3', 4, 4',- tetraaminobenzophenone (PNBI-4) as heat-resistant porous polymer sorbents for gas chromatographic separation and concentration of volatile organic and inorganic compounds with a boiling point from -56 to +400°C. Temperature limit for the use of PNBI sorbents-1-4 480-500°C, specific surface area 20-30 m2/g.
It is advisable to use PNBI-1-4 for gas chromatographic separation of organic compounds. They are characterized by increased selectivity for the separation of isomeric, cyclic and linear compounds, unsaturated and saturated compounds with an equal number of carbon atoms in the molecule. The selectivity of PNBI for the separation of pairs of isomeric or cyclic compounds is 3-17 times higher than the selectivity of tenax GC sorbent, and the selectivity of PNBI for the separation of pairs of unsaturated and saturated compounds is 2-25 times higher than the selectivity of tenax GC sorbent and polysorbimide-1 sorbent. PNBI-1-4 can be used to separate mixtures of isomeric compounds, cyclic and linear compounds. The earlier elution of cyclic compounds in comparison with compounds of normal structure distinguishes the studied PNBI sorbents from most known sorbents and makes it possible to determine the impurities of cyclic compounds in compounds of normal structure.
Water elutes on the PNBI with a narrow symmetrical peak, which makes it possible to use these sorbents to determine water impurities in various mixtures. Complete separation of air, CO and CO2 in gas mixtures is observed on these sorbents.
Heat-resistant PNBI-1-4 are promising sorbents for the development of new methods for gas chromatographic analysis and concentration of trace amounts of organic substances released during sanitary and chemical assessment in natural and simulated operating conditions of wood and composite materials, polymer building and composite materials based on polyvinyl chloride, polystyrene, carbamide, melamine- and phenol-formaldehyde resins. Chromatographic analysis of trace amounts of formaldehyde, methanol, and phenol shows that when concentrated on PNBI-3, formaldehyde does not chemically interact with phenol and both substances are detected on the same chromatographic column; this reduces the analysis time by 2-3 times compared with separate concentration on the sorbent polychrome-3 phenol, and on the sorbent is polyphenylquinoxaline of formaldehyde and methanol.
Downloads
References
Sakodynskij K. I., Panina L.I. Poristye polimernye sorbenty v gazohromatograficheskom analize. Analiz na polimernyh sorbentah : sb. – M. : NIITEKhIM, 1974:24-65. (In Russ.)
Sakodynskij K.I., Panina L.I. Polimernye sorbenty dlja molekuljarnoj hromatografii. M.: Nauka, 1977, 166 р. (In Russ.)
Panina L.I., Sakodynskij K.I. Poristye polimernye sorbenty dlja gazovoj hromatografii. Reaktivy i osobo chistye vewestva. Obzornaja informacija. M.: NIITEKhIM, 198 p. (In Russ.)
Glazunova L.D., Panina L.I., Sakodynskij K.I. Ispol'zovanie poristyh polimernyh sorbentov dlja koncentrirovanija mikroprimesej organicheskih soedinenij iz gazovoj i zhidkih prob. Uspehi himii. 1983; 52(7): 1225-1246. (In Russ.)
Koncentrirovanie sledov organicheskih soedinenij. Problemy analiticheskoj himii, tom 10. Sb. nauch. trudov Instituta geohimii i analiticheskoj himii im. V.I.Vernadskogo pod red. Kuz'mina N.M., M.: Nauka, 1990. 280 p. (In Russ.)
Panina L.I. Diss. d-ra him. nauk. Moscow, 1992, 579 р. (In Russ.)
Panina L.I., Sakodynskij K.I. Polimernye sorbenty dlja jekologicheskogo i promyshlennogo monitoringa. Himicheskaja promyshlennost'. 1996; 10: 68-74. (In Russ.)
Beljakova L.D. Diss. d-ra him. nauk. Moscow, 1997, 231 р. (In Russ.)
Khabarov V.B. Diss. kand. him. nauk. Moscow,1997, 258 р. (In Russ.)
Khabarov V.B., Panina L.I., Chumichjova O.A. Polifenilhinoksalin dlja koncentrirovanija i gazohromatograficheskogo opredelenija nizkomolekuljarnyh organicheskih soedinenij v poliakrilonitril'nom volokne metodom parofaznogo analiza. Sorbtsionnye i Khromatograficheskie Protsessy. 2014;14(2): 240-253. (In Russ.)
Khabarov V.B., Panina L.I., Burjak A.K., Habarov M.V. Glava 6 «Poristye polimernye sorbenty v hromatografii» pp. 64-164, pp. 265-297 monografii «Biologicheski aktivnye vewestva (hitozan i ego proizvodnye)» pod redakciej akademika RAN A.Ja. Samujlenko. Krasnodar. 2018, 356 p. (In Russ.)
Khabarov V.B., Pronin A.Ja., Samujlenko A.Ja., Burjak A.K., Grin' A.V. Izuchenie metodom HPLC fiziko-himicheskih harakteristik preparatov hitozana pri ih izgotovlenii i hranenii. Doklady Rossijskoj akademii s/h nauk. 2009; 4: 58-60. (In Russ.)
Khabarov V.B., Pronin A.Ja., Burjak A.K., Samujlenko A.Ja. Vozmozhnosti molekuljarnogo himicheskogo analiza metodom HPLC pri ispol'zovanii polimernogo sorbenta na osnove vysokosshitogo polidivinilbenzola. Reports of the Academy of Sciences, 2009; 427(1): 57-60. (In Russ.)
153. Hollis O. H. Porous polymers used in GC and LC. Chromatogr. Sci. 1973; 11: 335-342.
Cjurupa M. P. Diss. d-ra him. nauk. Moscow, 1985, 426 р. (In Russ.)
Davankov V. A., Tsyurupa M. P. Hypercrosslinked Polymeric Networks and Adsorbing Materials: Synthesis, Properties, Structure, and Applications. Comprehensive Analytical Chemistry. 2011; 56. 648 p.
Hollis O.H. Gas Separation on Microporous Polymer. VI International Symposium on Gas Chromatography. Rome, Italy : Inst. Petroleum, 1966: 8-12.
Hollis O. H. Separation of gaseous mixtures using porous polyaromatic polymer beads. Anal. Chem. 1966; 38: 309-316.
Hollis O.H. Water Analysis by Gas Chromatography using Porous Polymer Columns. J. Gas Chromatogr. 1966; 4(7):235-239.
Patent № 3729457 USA, 1973. Macronet polystyrene structures for ionites and method of producing same. (In Russ.)
Cropper F.R., Kaminsky S. Determination of Toxic Organic Compounds in Admixture in the Atmosphere by Gas Chromatography. Anal.Chem. 1963; 35(6): 735-743.
Novak J., Vasak V., Janak J. Chromatographic Method for the Concentration of Trace Impurities in the Atmopsphere and Other Gases. Anal. Chem. 1965; 37(6): 661-666.
Raymond A., Guiochon G. The Use of Graphitized Carbon Black as a Trapping Material for Organic Compounds in Light Gases Before a Gas Chromatographic Analysis. J. Chromatog. Sci. 1975; 13: 173-177.
Butles L.D., Burke M.F. Chromatographic Characterization of Porous Polymers for Use as Adsorbents in Sampling Columns. J. Chromatogr. 1976; 14: 117-122.
Novak J. Kolichestvennyj analiz metodom gazovoj hromatografii. M.: Mir. 1978: 92-99. (In Russ.)
Gavrilina L.Ja., Zhejvot V.I., Emel'janov I.D. Opredelenie kojefficienta obogawenija pri gazohromatograficheskom koncentrirovanii mikroprimesej. Izv. SO AN SSSR. 1982; 7: 97-102. (In Russ.)
Khabarov V.B. Sanitarno-himicheskie harakteristiki kompozicionnyh drevesnyh materialov i sinteticheskih smol po dannym gazovoj hromatografii. Sorbtsionnye i Khromatograficheskie Protsessy. 2015; 15(2): 196-215. (In Russ.)
Khabarov V.B., Panina L.I. Osobennosti sanitarno-himicheskoj ocenki ognezawiwjonnoj fanery metodom gazovoj hromatografii. Derevoobrabatyvajuwaja promyshlennost'. 2008; 5: 8-11. (In Russ.)
Khabarov V.B., Kovba I.T., Panina L.I. Ocenka polimernyh stroitel'nyh materialov dlja zhivotnovodcheskih zdanij. Veterinarija. 2008; 1: 35-40. (In Russ.)
Khabarov V.B. Innovacionnyj metod gazovoj hromatografii dlja sanitarno-himicheskoj ocenki teplovoj izoljacii stroitel'nyh konstrukcij. Kontrol' kachestva produkcii. 2023; 11: 51-55. (In Russ.)
Khabarov V.B., Panina L.I., L'vov A.I. Gazohromatograficheskoe opredelenie formal'degida, metanola, fenola i krezolov v podguznikah metodom parofaznogo analiza. Sorbtsionnye i Khromatograficheskie Protsessy. 2018; 18(5): 696-708. (In Russ.)
Khabarov V.B., Panina L.I. Innovacionnyj metod gazovoj hromatografii dlja opredelenija sanitarno-himicheskih harakteristik podguznikov. Kontrol' kachestva produkcii. 2024; 4(1): 40-47. (In Russ.)
Khabarov V.B. Opredelenie udel'nyh vybrosov organicheskih vewestv pri proizvodstve oboev na osnove polivinilhlorida metodom gazovoj hromatografii. Stroitel'nye materialy, oborudovanie, tehnologii 21 veka. 2016; 7-8: 32-39. (In Russ.)
Khhabarov V.B., Lebedev S.N. Primenenie innovacionnogo metoda gazovoj hromatografii dlja sanitarno-imicheskoj ocenki mebel'noj produkcii. Kontrol' kachestva produkcii. 2022; 1(1): 46-56. (In Russ.)
Khabarov V.B., Panina L.I., Lebedev S.N. O nesootvetstvii dejstvujuwej normativnoj bazy dlja ocenki himicheskoj bezopasnosti kompozicionnyh drevesnyh materialov trebovanijam zakonodatel'noj metrologii. Kontrol' kachestva produkcii. 2024; 6(1): 58-64. (In Russ.)
Khabarov V.B., Burjak A.K. Patent № 2764302 RF, 2022. (In Russ.)
Khabarov V.B., Mal'cev V.V. Author's certificate of the USSR no 1728793, 1992. (In Russ.)
Glazunova L.D., Zabel'nikov N.S., Panina L.I., Sakodynskij K.I., Habarov V.B. Author's certificate of the USSR no 993724 SSSR, 1982. (In Russ.)
Khabarov V.B., Panina L.I. Novye termostojkie poristye polimernye sorbenty ̶ polinaftailenbenzimidazoly dlya gazohromatograficheskogo razdeleniya i koncentrirovaniya letuchih veshchestv // Sbornik tezisov ХХII I Mendeleevskogo s"ezda po obshchej i prikladnoj himii, 7-12 oktyabrya, 2024, tom 4, s. 51. ХХII Mendeleevskij s"ezd po obshchej i prikladnoj himii, 7-12 oktyabrya, 2024, Federal'naya territoriya «Sirius», Rossiya. Sbornik tezisov dokladov v 7 tomah. Tom 4. — M.: OOO «Admiral Print», 2024. – 324 p.
Alentiev A.Yu, Syrtsova D.A., Nikiforov R.Yu., Ryzhikh V.E., Belov N.A., Skupov K.M., Volkova Yu.A., Ponomarev I.I. Polynaphthoylenebenzimidazoles as polymer materials for high-temperature membrane gas separation. Polymer. 2024; 308: 1-10.
Khabarov V.B., L'vov A.I., Panina L.I. Mnogofunkcional'nyj gazovyj hromatograf dlya analiza mikroprimesej letuchih veshchestv iz gazovyh sred. Trudy II Mezhdunarodnoj konferencii «Sovremennye tekhnologii nauchnogo priborostroeniya i informacionno-izmeritel'nyh sistem», 21-25. (In Russ.)
Khabarov V.B. Novoe ustrojstvo dlja vvoda prob organicheskih vewestv v metode gazovoj hromatografii. Sorbtsionnye i Khromatograficheskie Protsessy. 2013; 13(6): 947-958. (In Russ.)
Baskin L.Z., Vaulin V.F., Novikov V.A., Kisilyov N.G. Ampuly ftoroplastovye. Tekhnicheskie usloviya 95-766-80. Kirovo-Chepeckij himicheskij kombinat. 1980, 9 р. (In Russ.)
Khabarov V.B. Sozdanie dinamicheskim metodom v potoke azota graduirovochnyh smesej metanola i formal'degida. Sorbtsionnye i Khromatograficheskie Protsessy. 2012; 12(4): 513-522. (In Russ.)
Grob R.L. Hromatograficheskij analiz okruzhayushchej sredy. M.: Himiya, 1979: 95-103. (In Russ.)
MUK 2.1.2.1829-04 «Sanitarno-gigienicheskaja ocenka polimernyh i polimersoderzhawih stroitel'nyh materialov i konstrukcij, prednaznachennyh dlja primenenija v stroitel'stve zhilyh, obwestvennyh i promyshlennyh zdanij», utverzhdeny Glavnym gos. san. vrachom RF 06.01.2004, vvedeny s 01.05.2004. (In Russ.)




