Biodegradation of diesel fuel by a microbial consortium in the presence of 1-alkoxymethyl-2-methyl-5-hydroxypyridinium chloride homologues

Biodegradation

Volumn 20, Issue 5, 2009, Pages 661-671

  Chrzanowski, Łukasz ^a   Stasiewicz, Monika ^a   Owsianiak, Mikołaj ^b   Szulc, Alicja ^a   Piotrowska Cyplik, Agnieszka ^c   Olejnik Schmidt, Agnieszka K ^c   Wyrwas, Bogdan ^a  

^a POZNAN UNIVERSITY OF TECHNOLOGY   (Poland)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c POZNA UNIVERSITY OF LIFE SCIENCES   (Poland)

Author keywords

Biodegradation; DBAS; Diesel fuel; Hydrocarbons; Ionic liquids; Microbial consortium; Toxicity

Indexed keywords

ACTIVE SUBSTANCE; BACTERIAL CONSORTIUM; BIODEGRADATION EFFICIENCY; DBAS; ENVIRONMENTAL POLLUTIONS; HYDROPHOBIC COMPOUNDS; IN-CELL; MICROBIAL CONSORTIA; MICROBIAL CONSORTIUM; SIDE-CHAIN; TOXIC COMPOUNDS;

BIOCHEMISTRY; BIODEGRADATION; CELL MEMBRANES; CHAIN LENGTH; CHLORINE COMPOUNDS; DEGRADATION; DIESEL FUELS; HYDROCARBONS; HYDROPHOBICITY; IONIZATION OF LIQUIDS; IONS; MICROBIOLOGY; TOXICITY;

IONIC LIQUIDS;

GASOLINE; PYRIDINIUM DERIVATIVE;

BIOAVAILABILITY; BIODEGRADATION; DIESEL; ECOTOXICOLOGY; ENVIRONMENTAL RISK; HYDROPHOBICITY; MICROBIAL ACTIVITY; TOXIN;

ARTICLE; BIOREMEDIATION; DRUG EFFECT; LIQUID CHROMATOGRAPHY; METHODOLOGY; MICROBIOLOGY; SOLUBILITY;

BIODEGRADATION, ENVIRONMENTAL; CHROMATOGRAPHY, LIQUID; GASOLINE; PYRIDINIUM COMPOUNDS; SOIL MICROBIOLOGY; SOLUBILITY;

BACTERIA (MICROORGANISMS);

EID: 70349986213     PISSN: 09239820     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10532-009-9253-3     Document Type: Article

References (64)

1. Arning J, Stolte S, Böschen A, Stock F, Pitner WR, Welz-Biermann U, Jastorff B, Ranke J (2008) Qualitative and quantitative structure activity relationships for the inhibitory effects of cationic head groups, functionalised side chains and anions of ionic liquids on acetylcholinesterase. Green Chem 10:47-58. doi:10.1039/b712109a.
2. Belvèze LS (2004) Modeling and measurements of thermodynamic properties of ionic liquids. MSc thesis, University of Notre Dame, Notre Dame, IN.
3. Bernot RJ, Kennedy EE, Lamberti GA (2005) Effects of ionic liquids on the survival, movement, and feeding behavior of the freshwater snail, Physa acuta. Environ Toxicol Chem 24:1759-1765. doi:10.1897/04-614R.1.
4. Bösmann A, Datsevich L, Jess A, Lauter A, Schmitz C, Wasserscheid W (2001) Deep desulfurization of diesel fuel by extraction with ionic liquids. Chem Commun (Camb) 7:2494-2495. doi:10.1039/b108411a.
5. Bouchez-Naïtali M, Rakatozafy H, Marchal R, Leveau JY, Vandecasteele JP (1999) Diversity of bacterial strains degrading hexadecane in relation to the mode of substrate uptake. J Appl Microbiol 86:421-428. doi:10.1046/j.1365-2672.1999.00678.x.
6. Chrzanowski Ł, Owsianiak M, Wyrwas B, Aurich A, Szulc A, Olszanowski A (2009) Adsorption of sodium dodecyl benzene sulphonate (SDBS) on Candida maltosa EH 15 strain: influence on cell surface hydrophobicity and n-alkanes biodegradation. Water Air Soil Pollut 196:345-353. doi:10.1007/s11270-008-9782-0.
7. Cieniecka-Rosłonkiewicz A, Pernak J, Kubis-Feder J, Ramani A, Robertson AJ, Seddon KR (2005) Synthesis, anti-microbial activities and anti-electrostatic properties of phosphonium-based ionic liquids. Green Chem 7:855-862. doi:10.1039/b508499g.
8. Couling DJ, Bernot RJ, Docherty KM, Dixon JK, Maginn EJ (2006) Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling. Green Chem 8:82-90. doi:10.1039/b511333d.
9. Cross J (1994) Introduction to cationic surfactants. In: Cross J, Singer EJ (eds) Cationic surfactants, analytical and biological evaluation, surfactant science series, vol 53. Marcel Dekker, NY, Chapter 1.
10. Docherty KM, Kulpa CF Jr (2005) Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chem 7:185-189. doi:10.1039/b419172b.
11. Docherty KM, Dixon JK, Kulpa CF Jr (2007) Biodegradability of imidazolium and pyridinium ionic liquids by an activated sludge microbial community. Biodegradation 18:481-493. doi:10.1007/s10532-006-9081-7.
12. Endo S, Schmidt T (2006) Prediction of partitioning between complex organic mixtures and water: application of polyparameter linear free energy relationships. Environ Sci Technol 40:536-545. doi:10.1021/es0515811.
13. Fan H, Li Z, Liang T (2007) Experimental study on using ionic liquids to upgrade heavy oil. J Fuel Chem Technol 35:32-35.
14. Gao H, Luo M, Xing J, Wu Y, Li Y, Li W, Liu Q, Liu H (2008) Desulfurization of fuel by extraction with pyridinium-based ionic liquids. Ind Eng Chem Res 47:8384-8388. doi:10.1021/ie800739w.
15. García MT, Ribosa I, Guindulain T, Sánchez-Leal J, Vives-Rego J (2001) Fate and effect of monoalkyl quaternary ammonium surfactants in the aquatic environment. Environ Pollut 111:169-175. doi:10.1016/S0269-7491(99)00322-X.
16. García MT, Gathergood N, Scammells PJ (2005) Biodegradable ionic liquids Part II. Effect of the anion and toxicology. Green Chem 7:9-14. doi:10.1039/b411922c.
17. Gordon CM (2001) New developments in catalysis using ionic liquids. Appl Catal A 222:101-117. doi:10.1016/S0926-860X(01)00834-1.
18. Hansch C, Leo A (1995) Exploring QSAR: fundamentals and applications in chemistry and biology. American Chemical Society, Washington, DC.
19. Hartmans S, de Bont JAM, Harder W (1989) Microbial metabolism of short-chain unsaturated hydrocarbons. FEMS Microbiol Lett 63:235-264. doi:10.1111/j.1574-6968.1989.tb03399.x.
20. Heipieper HJ, Loffeld B, Keweloh H, de Bont JAM (1995) The cis/trans isomeration of unsaturated fatty acids in Pseudomonas putida S12: an indicator for environmental stress due to organic compounds. Chemosphere 30:1041-1051. doi:10.1016/0045-6535(95)00015-Z.
21. Isken S, de Bont JAM (1998) Bacteria tolerant to organic solvents. Extremophiles 2:229-238. doi:10.1007/s007920050065.
22. ISO 2871-2:1990 (1990) Surface active agents-detergents-determination of cationic-active matter content-part 2: cationic-active matter of low molecular mass (between 200 and 500).
23. Ito H, Hosokawa R, Morikawa M, Okuyama H (2008) A turbine oil-degrading bacterial consortium from soils of oil fields and its characteristics. Int Biodeter Biodegr 61:223-232. doi:10.1016/j.ibiod.2007.08.001.
24. Jastorff B, Mölter K, Behrend P, Bottin-Weber U, Filser J, Heimers A, Ondruschka B, Ranke J, Schaefer M, Schröder H, Stark A, Stepnowski P, Stock F, Störmann R, Stolte S, Welz-Biermann U, Ziegert S, Thöming J (2005) Progress in evaluation of risk potential of ionic liquids-basis for an eco-design of sustainable products. Green Chem 7:362-372. doi:10.1039/b418518h.
25. Kästner M, Breuer-Jammali M, Mahro B (1994) Enumeration and characterization of the soil microflora from hydrocarbon-contaminated soil sites able to mineralize polycyclic aromatic hydrocarbons (PAH). Appl Microbiol Biotechnol 41:267-273. doi:10.1007/BF00186971.
26. Kralisch D, Stark A, Körsten S, Kreisel G, Ondruschka B (2005) Energetic, environmental and economic balances: spice up your ionic liquid research efficiency. Green Chem 7:301-309. doi:10.1039/b417167e.
27. Liu D, Gui J, Song L, Zhang X, Sun Z (2008) Deep desulfurization of diesel fuel by extraction with task-specific ionic liquids. Petrol Sci Tech 26:973-982. doi:10.1080/10916460600695496.
28. Maila MP, Randima P, Drønen K, Cloete TE (2006) Soil microbial communities: influence of geographic location and hydrocarbon pollutants. Soil Biol Biochem 38:303-310.
29. Matzke M, Stolte S, Thiele K, Juffernholz T, Arning J, Ranke J, Welz-Biermann U, Jastorff B (2007) The influence of anion species on the toxicity of 1-alkyl-3-methylimidazolium ionic liquids observed in an (eco)toxicological test battery. Green Chem 9:1198-1207. doi:10.1039/b705795d.
30. Matzke M, Thiele K, Müller A, Filser J (2009) Sorption and desorption of imidazolium based ionic liquids in different soil types. Chemosphere 74:568-574. doi:10.1016/j.chemosphere.2008.09.049.
31. Meylan WM, Howard PH (1995) Atom/fragment contribution method for estimating octanol-water partition coefficients. J Pharm Sci 84:83-92. doi:10.1002/jps.2600840120.
32. Mochizuki Y, Sugawara K (2008) Removal of organic sulfur from hydrocarbon resources using ionic liquids. Energy Fuels 22:3303-3307. doi:10.1021/ef800400k.
33. Modelli A, Sali A, Galletti P, Samorì C (2008) Biodegradation of oxygenated and non-oxygenated imidazolium-based ionic liquids in soil. Chemosphere 73:1322-1327. doi:10.1016/j.chemosphere.2008.07.012.
34. Olivier-Bourbigou H, Magna L (2002) Ionic liquids: perspectives for organic and catalytic reactions. J Mol Catal A 182:419-437. doi:10.1016/S1381-1169(01)00465-4.
35. Pernak J, Branicka M (2003) The properties of 1-alkoxymethyl-3-hydroxypyridinium and 1-alkoxymethyl-3-dimethylaminopyridinium chlorides. J Surfactants Deterg 6:119-123. doi:10.1007/s11743-003-0254-5.
36. Pernak J, Branicka M (2004) Synthesis and aqueous ozonation of some pyridinium salts with alkoxymethyl and alkylthiomethyl hydrophobic groups. Ind Eng Chem Res 43:1966-1974. doi:10.1021/ie030118z.
37. Pernak J, Chwała P (2003) Synthesis and antimicrobial activities of choline-like quaternary ammonium chlorides. Eur J Med Chem 38:11-12. doi:10.1016/j.ejmech.2003.09.004.
38. Pernak J, Kalewska J, Ksycińska H, Cybulski J (2001a) Synthesis and anti-microbial activities of some pyridinium salts with alkoxymethyl hydrophobic group. Eur J Med Chem 36:899-907. doi:10.1016/S0223-5234(01)80005-2.
39. Pernak J, Rogoża J, Mirska I (2001b) Synthesis and antimicrobial activities of new pyridinium and benzimidazolium chlorides. Eur J Med Chem 36:313-320. doi:10.1016/S0223-5234(01)01226-0.
40. Pernak J, Goca I, Mirska I (2004) Anti-microbial activities of protic ionic liquids with lactate anion. Green Chem 6:323-329. doi:10.1039/b404625k.
41. PN-86 C-04573/01 (1986) Polish standard method for gravimetric determination of hydrocarbon. Polski Komitet Normalizacji, Miar i Jakości, UKD 663.6.001.4:628.312:543.3.
42. Potter TL, Simmons KE (1998) Composition of petroleum mixtures. Total petroleum hydrocarbon criteria working group series, vol 2. Amherst Scientific, Amherst.
43. Ranke J, Mölter K, Stock F, Bottin-Weber U, Poczobutt J, Hoffmann J, Ondruschka B, Filser J, Jastrorff B (2004) Biological effects of imidazolium ionic liquids with varying chain lenghts in acute Vibrio fisheri and WST-1 cell viability assays. Ecotoxicol Environ Saf 58:396-404.
44. Roberts DW, Costello J (2003) QSAR and mechanism of action for aquatic toxicity of cationic surfactants. QSAR Comb Sci 22:220-225.
45. Rogers RD, Seddon KR (2002) Ionic liquids: industrial applications for green chemistry. American Chemical Society ACS Ser. 818. Oxford University Press, Washington.
46. Ropel L, Belvèze LS, Aki SNVK, Stadtherr MA, Brennecke JF (2005) Octanol-water partition coefficients of imidazolium-based ionic liquids. Green Chem 7:83-90.
47. Rosenberg M, Gutnick D, Rosenberg E (1980) Adherence of bacteria to hydrocarbons: a simple method for measuring cell-surface hydrophobicity. FEMS Microbiol Lett 9:29-33.
48. Seddon KR (2003) Ionic liquids: a taste of the future. Nat Mater 2:363-365.
49. Shi LJ, Shen BX, Wang GQ (2008) Removal of naphthenic acids from Beijiang crude oil by forming ionic liquids. Energy Fuels 22:4177-4181.
50. Sikkema J, de Bont JA, Poolman B (1995) Mechanisms of membrane toxicity of hydrocarbons. Microbiol Rev 59:201-222.
51. Siskin M, Francisco MA, Billimoria RM (2008) Upgrading of petroleum resid, bitumen or heavy oils by the separation of asphaltenes and/or resins therefrom using ionic liquids. U.S. Patent 2008/0245705 A1. October.
52. Sjögren M, Li H, Rannug U, Westerholm R (1995) A multivariate statistical analysis of chemical composition and physical characteristics of ten diesel fuels. Fuel 74:983-989.
53. Stasiewicz M, Mulkiewicz E, Tomczak-Wandzel R, Kumirska J, Siedlecka EM, Gołebiowski M, Gajdus J, Czerwicka M, Stepnowski P (2008) Assessing toxicity and biodegradation of novel, environmentally benign ionic liquids (1-alkoxymethyl-3-hydroxypyridinium chloride, saccharinate and acesulfamates) on cellular and molecular level. Ecotoxicol Environ Saf 71:157-165.
54. Stepnowski P, Mrozik W, Nichthauser J (2007) Adsorption of alkylimidazolium and alkylpyridinium ionic liquids onto natural soils. Environ Sci Technol 41:511-516.
55. Stock F, Hoffmann J, Ranke J, Störmann R, Ondruschka B, Jastorff B (2004) Effects of ionic liquids on the acetylcholineesterase-a structure-activity relationship consideration. Green Chem 6:286-290.
56. Stolte S, Arning J, Bottin-Weber U, Matzke M, Stock F, Thiele K, Uerdingen M, Welz-Biermann U, Jastorff B, Ranke J (2006) Anion effects on the cytotoxicity of ionic liquids. Green Chem 8:621-629.
57. Stolte S, Arning J, Bottin-Weber U, Pitner WR, Welz-Biermann U, Jastorff B, Ranke J (2007a) Effects of different head groups and modified side chains on the cytotoxicity of ionic liquids. Green Chem 9:760-767.
58. Stolte S, Matzke M, Arning J, Böschen A, Pitner WR, Welz-Biermann U, Jastorff B, Ranke J (2007b) Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids. Green Chem 9:1170-1179.
59. Studzińska S, Sprynskyy M, Buszewski B (2008) Study of sorption kinetics of some ionic liquids on different soil types. Chemosphere 71:2121-2128.
60. Vaher M, Koel M, Kaljurand M (2002) Application of 1-alkyl-3-methylimidazolium-based ionic liquids in non-aqueous capillary electrophoresis. J Chromatogr A 979:27-32.
61. Wasserscheid P, Welton T (2002) Ionic liquids in synthesis. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
62. Waters J, Kupfer W (1976) The determination of cationic surfactants in the presence of anionic surfactant in biodegradation test liquors. Anal Chim Acta 85:241-251.
63. Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99:2071-2083.
64. Zhang Y, Bakshi BR, Demessie ES (2008) Life cycle assessment of an ionic liquid versus molecular solvents and their applications. Environ Sci Technol 42:1724-1730.