THE DETERMINATION OF PHENOLS COMPOUNDS IN DISINFECTANTS
https://doi.org/10.32362/2410-6593-2017-12-3-5-20
Abstract
The aspects of analytical determination of disinfectants derivatives of the phenol series аrе considered. The possibility of codetermination of five derivatives of this series in different disinfectants using the RP-HPLC method in the isocratic mode (UV detection) is shown. Alternatively, the possibilities of the determination with the use of spectrophotometry and GC methods are considered. This study and previous ones showed that the extraction of phenol derivatives by organic solvents from а wide range of disinfectants is feasible only in some cases, preferably with the use of hexane as an extractant. Further spectrophotometry of hexane extracts does not always enable to correctly compensate for the effect of background impurities and requires an additional separation of the components. The literature data and experimental results suggest that it is more efficient to analyze the whole series of disinfectants in isopropanol (sometimes in water) by chromatographic methods, preferably by HPLC. Sample preparation reduces to the solubilization of batches of ready-made disinfectants in isopropanol/water. It is optimal to carry out the chromatographic study using elution with acetonitrile-based systems (for example, СН3СN:Н2O, 60:40) providing the correct determination (λ = 280 nт) of phenol derivatives. The completeness of extraction (if the extraction method is used), as well as the metrology aspects of all the analytical determination is set directly in а laboratory during the realization of procedures of introduction/validation according to the internal documents of the system quality management for the relevant structural unit.
About the Authors
L. A. Nosikova
Moscow Technological University (Institute of Fine Chemical Technologies)
Russian Federation
Moscow 119571, Russia
Russian Federation
Moscow 119571, Russia
I. O. Melnikov
Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russian Federation
Moscow 119991, Russia
Russian Federation
Moscow 119991, Russia
A. N. Kochetov
JSC «BVT BARIER RUS»
Russian Federation
Balashikha, Moscow region 143900, Russia
Russian Federation
Balashikha, Moscow region 143900, Russia
References
1. Fedorova L.S. Contemporary directions in the field of disinfectants improvements // Dezinfektsionnoe delo (Disinfection Affairs). 2003. № 4. P. 41–43. (in Russ.).
2. Kovalishena О.V. Nosocomal infections pathogens description and resistance to disinfectants // Dezinfektsionnoe delo (Disinfection Affairs). 2005. № 3. P. 33–39. (in Russ.).
3. Shandala M.G. Struggle with virus infections as disinfectology problem // Dezinfektsionnoe delo (Disinfection Affairs). 2006. № 3. P. 23–26. (in Russ.).
4. Suller M.T.E., Russell A.D. Triclosan and antibiotic resistance in Staphylococcus aureus // J. Antimicrob. Chemotherapy. 2000. V. 46. P. 11–18.
5. Rodin V.B., Kobzev E.N., Detusheva E.V., Martynova V.N., Timoshinova E.V., Detushev K.V., Chugunov V.A., Holodenko V.P. Cross-resistance of microorganisms to antibiotics, coupled with resistance to disinfectants // Dezinfektsionnoe delo (Disinfection Affairs). 2011. № 4. P. 20–26. (in Russ.).
6. Schmid M.B., Kaplan N. Reduced triclosan susceptibility in methicillin-resistant Staphylococcus epidermidis // J. Antimicrob. Agents and Chemotherapy. 2004. V. 48. № 4. Р. 1397–1393.
7. Alello A.A., Marshall B., Levy S.B., DellaLatta P., Larson E. Relationship between triclosan and susceptibilities of bacteria isolated from hands in the community // J. Antimicrob. Agents and Chemotherapy. 2004. V. 48. № 8. P. 2973–2979.
8. Pycke B.F.G., Crabbé A., Verstraete W., Leys N. Characterization of triclosan-resistant mutants reveals multiple antimicrobial resistance mechanisms in Rhodospirillum rubrum S1H // Appl. Environm. Microbiology. 2010. V. 76. № 10. Р. 3116–3123.
9. Alello A.A., Marshall B., Levy S.B., Della-Latta P., Lin S.X., Larson E. Antibacterial Cleaning products and drug resistance // Emerging Infections Diseases. 2005. V. 11. № 10. Р. 1565–1570.
10. Zueva L.P., Kolosovskaya E.N., Lyubimova A.V., Aslanov B.I., Goncharov A.E., Svetlichnaya Yu.S. Substantiation of disinfectant sensitivity monitoring of pathogens circulating in hospitals // Dezinfektsionnoe delo (Disinfection Affairs). 2011. № 2. P. 45–48. (in Russ.).
11. Panteleeva L.G. Condition and ways of perfection of arsenal of disinfecting means for struggle with virus infection // Dezinfektsionnoe delo (Disinfection Affairs). 2006. № 4. P. 14–17. (in Russ.).
12. Satellite of Pharmacist / Eds. I.I. Loewenstein, I.А. Oberhard. Moscow-Leningrad: Publishing house of medical literature, 1936. P. 395–396. (in Russ.).
13. Handelsman B.I. Disinfection Affairs. Moscow: Meditsina Publ., 1971. 392 p. (in Russ.).
14. Pkhakadze T.Ya. Antiseptics and disinfectants in the prophylaxis of nosocomial infections // Кlinicheskaya mikrobiologiya i antimikrobnaya chimioterapiya (Clinical Microbiology and antimicrobial chemotherapy). 2002. V. 4. № 1. P. 42–48. (in Russ.).
15. Bidevkina M.V. Methodological approaches to hygienic rating of active fraction desinfectants, possessed of selective irritant action // Dezinfektsionnoe delo (Disinfection Affairs). 2012. № 3. P. 34–38. (in Russ.)
16. Pozdnyakov V.S., Chizhov A.I., Ivanov N.G. o-Phenylphenol // Toksikologicheskiy vestnik (Toxicological Bulletin). 2005. № 5. P. 47–49. (in Russ.).
17. Pozdnyakov V.S., Chizhov A.I., Ivanov N.G. 2-Benzyl-4-chlorophenol // Toksikologicheskiy vestnik (Toxicological Bulletin). 2005. № 5. P. 49–50. (in Russ.).
18. Zhukova O.L., Dargaeva T.D., Markaryan A.A., Abramov A.A. Study of the phenol composition of the Comarum palustre soil-covered organs // Moscow University Chemistry Bulletin. 2006. V. 61. № 5. P. 40–45.
19. Kochetova M.V., Semenistaya E.N., Larionov O.G., Revina A.A. Determination of biologically active phenols and polyphenols in various objects by chromatographic techniques // Russian Chemical Reviews. 2007. V. 76. № 1. P. 79–90.
20. Benetis R., Radusiene J., Jakstas V., Janulis V., Puodziuniene G., Milasius A. Quantitative HPLC determination of phenolic compounds in yarrow // Pharm. Chem. J. 2008. V. 42. № 3. Р. 153–156.
21. Vernikovskaya N.A., Temerdashev Z.A. Identification and chromatographic determination of phenolic compounds in yarrow // Analitika i kontrol' (Analytics and Control). 2012. V. 16. № 2. P. 188–195. (in Russ.).
22. Temerdashev Z.A., Frolova N.A., Kolychev I.A. Determination of phenolic compounds in medicinal herbs by reversed-phase HPLC // Journal of Analytical Chemistry. 2011. V. 66. № 4. P. 407–414.
23. The registry of disinfectants [Electronic resource] Access mode http://dezreestr.ru/ (date of access 09.06.2017).
24. Liu T., Wu D., High-performance liquid chromatographic determination of triclosan and triclocarban in cosmetic products // J. Cosmet. Sci. 2012. V. 34. № 5. Р. 489–494.
25. Achari R.G., Chin D. HPLC analysis of some bacteriostats in deodorant sticks and soap // J. Cosmet. Sci. 1981. V. 32. P. 163-173.
26. Wang L.H., Tso M., Chin C.-Y. Simultaneous determination of chlorinated bacteriostats in cosmetic and pharmaceutical products // J. Cosmet. Sci. 2005. V. 56. P. 183–192.
27. Balakrishna A., Annar S., Reddy M.V.N. [et al.] Synthesis, anti-microbial properties of 3-(3’-сhloro-4’- nitrophenyl)-2-(substituted phenoxy)-3,4-dihydro-2H1,3,2-λ5–benzoxaphosphinin-2-ones // J. Chem. Pharm. Res. 2009. V. 1. P. 250–256.
28. Frecer V., Megnassana E., Miertus S. Design and in silico screening of combinatorial library of antimalarial analogs of triclosan inhibiting Plasmodium falciparum enoyl-acyl carrier protein reductase // Eur. J. Med. Chem. 2009. V. 44. № 7. Р. 3009–3019.
29. Chung D., Papadakis S.E., Yam K.L. Evaluation of a polymer coating containing triclosan as the antimicrobial layer for packaging materials // Int. J. Foоd. Sci. and Tech. 2003. V. 38. № 1. Р. 165–169.
30. Shandala M.G. Condition and perspectives of developing and introduction in practice the new disinfectology technologies // Dezinfektsionnoe delo (Disinfection Affairs). 2005. № 4. P. 17–22. (in Russ.).
31. Sokolova N.F. The contemporary problems of organization and conductance of disinfection means in lpu with intension of preventive treatment of intrahospital infection // Dezinfektsionnoe delo (Disinfection Affairs). 2005. № 4. P. 31–40. (in Russ.).
32. Makhneva T.V., Chepko V.I., Zakharchenko A.V., Chijov A.I., Dubinski D.Yu., Ryabov V.V., Kolomnikov G.I., Kudriavtseva E.E., Iljin I.Yu., Topolyanski B.E., Novikov V.S., Pomogaeva L.S., Kurshin D.A., Suslo M.A., Chuev I.P. Deposit of producers means of disinfection, disinsection and deratization in development of disinfection means of Russian Federation // Dezinfektsionnoe delo (Disinfection Affairs). 2006. № 3. P. 17–22. (in Russ.).
33. Kreyngold S.U. Spectrophotometric determinathion of phenols in disinfection preparations after thin-layer chromatography separation // Dezinfektsionnoe delo (Disinfection Affairs). 2003. № 4. P. 45–46. (in Russ.).
34. Tchizhov A.I. KEMI-SIDE as a new generations disinfectant. The practical conditions trial results // Dezinfektsionnoe delo (Disinfection Affairs). 2005. № 3. P. 62–65. (in Russ.).
35. Kreyngold S.U. A practical guide to chemical analysis disinfection drugs. Moscow: Ekspressprint Publ., 2002. 156 p. (in Russ.).
36. Nosikova L.A., Kochetov A.N. Analytical determination of triclosan and tinosan in disinfectants gels // Tonkie khimicheskie tekhnologii (Fine Chemical Technologies). 2015. V. 10. № 3. P. 56–61. (in Russ.).
37. Ohlemeier A., Gavlick W.K. Liquid chromatographic determination of phenolic compounds in hospital disinfectant products // J. Liquid Chromatogr. 1995. V. 18. № 9. Р. 1833–1849.
38. Kochetova M.V., Larionov O.G., Ulyanova E.V. The investigation of qualytative composition of cognacs by HPLC // Sorbtsionnye i khromatograficheskie protsessy (Sorption and chromatographic processes). 2008. V. 8. № 4. P. 658–667. (in Russ.).
39. Gatidou G., Thomaidis N.S., Stasinakis A.S. [et al.] Simultaneous determination of the endocrine disrupting compounds nonylphenol, nonylphenol ethoxylates, triclosan and bisphenol A in wastewater and sewage sludge by gas chromatography–mass spectrometry // J. Chromatogr. A. 2007. V. 1138. P. 32–41.
40. Cheng C.-Y., Wang Y.-C., Chen H.-C., Ding W.-H. Simplified derivatization method for triclosan determination in personal care products by gas chromatography-mass spectrometry // J. Chin. Chem. Soc. 2011. V. 58. № 1. Р. 49–52.
41. Gavrilin M.V., Popova O.I., Gubanova E.A. Phenolic compounds of the aerial parts of Clary sage (Salvia sclarea L.), cultivated in Stavropol region // Khimiya rastitel’nogo syr’ja (Сhemistry of Vegetable Raw Materials). 2010. № 4. P. 99–104. (in Russ.).
42. Piccoli А., Fiori J., Andrisano V., Orioli M. Determination of triclosan in personal health care products by liquid chromatography (HPLC) // Il Farmaco. 2002. V. 57. P. 369–372.
43. Mezcua M., Gómez M.J., Ferrer I. [et al.] Evidence of 2,7/2,8-dibenzodichloro-p-dioxin as a photodegradation product of triclosan in water and wastewater samples // Anal. Chim. Acta. 2004. V. 524. P. 241–247.
44. Catalina M.I., Dallüge J., Vreuls R.J.J., Brinkman V.A.T. Determination of chlorophenoxy acid herbicides in water by in situ esterification followed by in-vial liquid–liquid extraction combined with largevolume on-column injection and gas chromatography–mass spectrometry // J. Chromatogr. A. 2000. V. 877. P. 153–166.
45. Boehmer W., Ruedel H., Wenzel A., SchroeterKermani C. Retrospective monitoring of triclosan and methyl-triclosan in fish: results from the german environmental specimen bank // J. Organohalogen Comp. 2004. V. 66. P. 1516–1521.
46. Rojas L.B., Quideau S., Pardon P., Charrouf Z. Colorimetric evaluation of phenolic content and GC-MS characterization of phenolic composition of alimentary and cosmetic argan oil and press cake // J. Agric. Food Chem. 2005. V. 53. № 23. P. 9122–9127.
47. Vorob'eva T. V., Terletskaya A.V., Kushchevskaya N. F. Standard and unified methods for the determination of phenols in natural and drinking waters and the main directions of improvement // Khimiya i tekhnologiya vody (Chemistry and Technology of Water). 2007. V. 29. № 4. P. 370–390. (in Russ.).
48. Tsai S.-W., Shih V-W., Pan Y.-P. Determinations and residual characteristics of triclosan in household food detergents of Taiwan // Chemosphere. 2008. V. 72. Р. 1250–1255.
49. Guo J.-H., Li X.-H., Cao X.-L. [et al.] Determinstion of triclosan, triclocarban and methyl-triclosan in aqueous samples by dispersive liquid-liquid microextraction combined with rapid liquid chromatography // J. Chromatogr. A. 2009. V. 1216. P. 3083–3043.
50. Chen X., Nielsen J. L., Furgal K. [et al.] Biodegradation of triclosan and formation of methyltriclosan in activated sludge under aerobic conditions // Chemosphere. 2011. V. 84. P. 452–456.
51. Baranovska I., Wojciechowska I. Development of SPE/HPLC-DAD to determine residues of selected disinfectant agents in surface water // Pol. J. Environ. Stud. 2012. V. 21. № 2. Р. 269– 277.
52. Opeolu B.O., Fatoki O.S., Odendaal J. Development of a solid-phase extraction method followed by HPLC-UV detection for the determination of phenols in water // Int. J. Phys. Sci. 2010. V. 5. № 5. Р. 576–581.
53. Kreingold S.U., Shestakov K.A. Determination of triclosan in liquid toilet antibacterial soap // Dezinfektsionnoe delo (Disinfection Affairs). 2002. № 3. P. 46–47. (in Russ.).
54. Kretova L.G., Lunev M.I. Thin layer chromatography: a methodological guide. Moscow: Agroprogress Publ., 2000. P. 53–56. (in Russ.).
55. Podolina E.A., Groshev E.N., Rudakov O.B. Extraction and instrumental methods for determining of phenols in condensed matter // Kondensirovanne sredy i mezhfaznye granitcy (Condensed Matter and Interphase Boundaries). 2011. V. 13. № 1. P. 72–79. (in Russ.).
56. Belikov V.G. Analysis of pharmaceutical substances photometric methods. Experience local experts // Rossiyskiy Khimicheskiy Zhurnal (Russian Journal of Chemistry). 2002. V. 46. № 4. P. 52–56. (in Russ.).
57. Sukiasyan A.N., Kopylov A.I., Malysheva L.F. Photocolorimetric method for the determination of chlorhexidine gluconate is the antiseptic drugs // Khimiko-Farmatsevticheskii Zhurnal (ChemicalPharmaceutical Journal). 1984. V. 18. № 10. P. 1271–1273. (in Russ.).
58. Nosikova L.A., Shestakov K.A., Kochetov A.N., Kotsur O.I. Determination of the content of the polymeric guanidine derivatives in antiseptics by the method of two-phase titration // Tonkie khimicheskie tekhnologii (Fine Chemical Technologies). 2015. V. 10. № 2. P. 20–24. (in Russ.).
59. Shestakov K.A., Kochetov A.N., Kotsur O.I., Strelnikov I.I. Determination of the content of octenidine in disinfectants // Dezinfektsionnoe delo (Disinfection Affairs). 2009. № 1. P. 39–40. (in Russ.).
60. Shestakov K.A., Kochetov A.N., Kotsur O.I., Strelnikov I.I. The comparative characteristic of two methods of determination of quaternary ammonium compounds in the presence of polyhexamethyleneguanidine in disinfectants // Dezinfektsionnoe delo (Disinfection Affairs). 2007. № 1. P. 64–65. (in Russ.).
61. Shestakov K. A., Kochetov A. N., Kotsur O. I., Method for the determination of quaternary ammonium compounds in antiseptic drugs // Proceedings of the 43-rd All-Russian Scientific Conference "Actual problems of theoretical, experimental, clinical medicine and pharmacy". Tyumen: Pechatnik Publ., 2009. P. 292.
Review
For citations:
Nosikova L.A., Melnikov I.O., Kochetov A.N. THE DETERMINATION OF PHENOLS COMPOUNDS IN DISINFECTANTS. Fine Chemical Technologies. 2017;12(3):5-20. (In Russ.) https://doi.org/10.32362/2410-6593-2017-12-3-5-20
Views: 515
Email this article 
