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Kinetic analysis of biodesulfurization of model oil containing multiple alkyl dibenzothiophenes

  • Environmental biotechnology
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Abstract

Biodesulfurization is regarded as a promising alternative technology for desulfurization from diesel oil due to its mild operating conditions and its ability to remove sulfur from alky dibenzothiophenes (Cx-DBTs). The diesel oil contains complex mixtures of Cx-DBTs in which individual microbial biodesulfurization may be altered. In this work, interactions among three typical Cx-DBTs such as dibenzothiophenes (DBT), 4-methyldibenzothiophene (4-MDBT), and 4,6-dimethyldibenzothiophene (4,6-DMDBT) were investigated using Mycobacterium sp. ZD-19 in an airlift reactor. The experimental results indicated that the desulfurization rates would decrease in the multiple Cx-DBTs system compared to the single Cx-DBT system. The extent of inhibition depended upon the substrate numbers, concentrations, and affinities of the co-existing substrates. For example, compared to individual desulfurization rate (100 %), DBT desulfurization rate decreased to 75.2 % (DBT + 4,6-DMDBT), 64.8 % (DBT + 4-MDBT), and 54.7 % (DBT + 4,6-DMDBT + 4-MDBT), respectively. This phenomenon was caused by an apparent competitive inhibition of substrates, which was well predicted by a Michaelis–Menten competitive inhibition model.

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References

  • Boltes K, del Aguila RA, Garcia-Calvo E (2007) Biodesulfurization of alkylated forms of dibenzothiophene by Pseudomonas putida CECT5279. J Biotechnol 131:S143–S144

    Article  Google Scholar 

  • Boltes K, Caro A, Leton P, Rodriguez A, Garcia-Calvo E (2008) Gas–liquid mass transfer in oil–water emulsions with an airlift bio-reactor. Chem Eng Process 47:2408–2412

    Article  CAS  Google Scholar 

  • Chen H, Zhang WJ, Chen JM, Cai YB, Li W (2008a) Desulfurization of various organic sulfur compounds and the mixture of DBT + 4,6-DMDBT by Mycobacterium sp. ZD-19. Bioresour Technol 99:3630–3634

    Article  CAS  Google Scholar 

  • Chen H, Zhang WJ, Cai YB, Zhang Y, Li W (2008b) Elucidation of 2-hydroxybiphenyl effect on dibenzothiophene desulfurization by Microbacterium sp. strain ZD-M2. Bioresour Technol 99:6928–6933

    Article  CAS  Google Scholar 

  • Chen H, Cai YB, Zhang WJ, Li W (2009) Methoxylation pathway in biodesulfurization of model organosulfur compounds with Mycobacterium sp. Bioresour Technol 100:2085–2087

    Article  CAS  Google Scholar 

  • Feng JH, Zeng YY, Ma CQ, Cai XF, Zhang Q, Tong MY, Yu B, Xu P (2006) The surfactant tween-80 enhances biodesulfurization. Appl Environ Microbiol 72:7390–7393

    Article  CAS  Google Scholar 

  • Gunam IBW, Yaku Y, Hirano M, Yamamura K, Tomita F, Sone T, Asano K (2006) Biodesulfurization of alkylated forms of dibenzothiophene and benzothiophene by Sphingomonas subarctica T7b. J Biosci Bioeng 101:322–327

    Article  CAS  Google Scholar 

  • Izumi Y, Ohshiro T, Ogino H, Hine Y, Shimao M (1994) Selective desulfurization of dibenzothiophene by Rhodococcus erythropolis D-1. Appl Environ Microbiol 60:223–226

    CAS  Google Scholar 

  • Kirimura K, Furuya T, Nishii Y, Ishii Y, Kino K, Usami S (2001) Biodesulfurization of dibenzothiophene and its derivatives through the selective cleavage of carbon–sulfur bonds by a moderately thermophilic bacterium Bacillus subtilis WU-S2B. J Biosci Bioeng 91:262–266

    CAS  Google Scholar 

  • Kirkwood KM, Andersson JT, Fedorak PM, Foght JM, Gray MR (2007) Sulfur from benzothiophene and alkylbenzothiophenes supports growth of Rhodococcus sp. strain JVH1. Biodegradation 18(5):541–549

    Article  CAS  Google Scholar 

  • Kobayashi M, Horiuchi K, Yoshikawa O, Hirasawa K, Ishii Y, Fujino K, Sugiyama H, Maruhashi K (2001) Kinetic analysis of microbial desulfurization of model and light gas oils containing multiple alkyl debenzothiophenes. Biosci Biotechnol Biochem 65(2):298–304

    Article  CAS  Google Scholar 

  • Konishi J, Onaka T, Ishii Y, Suzuki M (2000) Demonstration of the carbon–sulfur bond targeted desulfurization of benzothiophene by thermophilic Paenibacillus sp. strain A11-2 capable of desulfurizing dibenzothiophene. FEMS Microbiol Lett 187:151–154

    Article  CAS  Google Scholar 

  • Li FL, Xu P, Ma CQ, Luo LL, Wang XS (2003) Deep desulfurization of hydrodesulfurization-treated diesel oil by a facultative thermophilic bacterium Mycobacterium sp. X7B. FEMS Microbiol Lett 223:301–307

    Article  CAS  Google Scholar 

  • Li FL, Xu P, Feng JH, Meng L, Zheng Y, Luo LL, Ma CQ (2005) Microbial desulfurization of gasoline in a Mycobacterium goodii X7B immobilized-cell system. Appl Environ Microbiol 71:276–281

    Article  CAS  Google Scholar 

  • Li W, Wang MD, Chen H, Chen JM, Shi Y (2006) Biodesulfurization of dibenzothiophene by growing cells of Gordonia sp. in batch cultures. Biotechnol Lett 28:1175–1179

    Google Scholar 

  • Li YG, Ma J, Zhang QQ, Wang CS, Chen Q (2007) Sulfur selective desulfurization of dibenzothiophene and diesel oil by newly isolated Rhodococcus erythropolis NCC-1. Chin J Chem 25:400–405

    Article  CAS  Google Scholar 

  • Liang F, Lu MM, Birch ME, Keener MC, Liu ZF (2006) Determination of polycyclic aromatic sulfur heterocycles in diesel particular matter and diesel fuel by gas chromatography with atomic emission detection. J Chromatogr A 1114:145–153

    Article  CAS  Google Scholar 

  • Luo MF, Xing JM, Gou ZX, Li S, Liu HZ, Chen JY (2003) Desulfurization of dibenzothiophene by lyophilized cells of Pseudomonas delafieldii R-8 in the presence of dodecane. Biochem Eng J 13:1–6

    Article  CAS  Google Scholar 

  • Marcelis CLM, van Leeuwen M, Polderman HG, Janssen AJH, Lettinga G (2003) Model description of dibenzothiophene mass transfer in oil/water dispersions with respect to biodesulfurization. Biochem Eng J 16:253–264

    Article  CAS  Google Scholar 

  • Mehrnia MR, Towfighi J, Bonakdarpour B, Akbarnegad MM (2004) Influence of top-section design and draft-tube height on the performance of airlift bioreactors containing water-in-oil microemulsion. J Chem Technol Biotechnol 79:260–267

    Article  CAS  Google Scholar 

  • Naito M, Kawamoto T, Fujino K, Kobayashi M, Maruhashi K, Tanaka A (2001) Long-term repeated biodesulfurization by immobilized Rhodococcus erythropolis KA2-5-1 cells. Appl Microbiol Biotechnol 55:374–378

    Article  CAS  Google Scholar 

  • Nekodzuka S, Nakajima-Kambe T, Nomura N, Lu J, Nakahara T (1997) Specific desulfurization of dibenzothiophene by Mycobacterium sp. strain G3. Biocatal Biotransform 15(1):17–27

    Article  CAS  Google Scholar 

  • Nomura N, Takada M, Okada H, Shinohara Y, Nakajima-Kambe T, Nakahara T, Uchiyama H (2005) Identification and functional analysis of genes required for desulfurization of alkyl dibenzothiophenes of Mycobacterium sp. G3. J Biosci Bioeng 100:398–402

    Article  CAS  Google Scholar 

  • Okada H, Nomura N, Nakahara T, Maruhashi K (2002) Analyses of dibenzothiophene metabolic pathway in Mycobacterium sp. G3. J Biosci Bioeng 93:491–497

    CAS  Google Scholar 

  • Piddington CS, Kovacevich BR, Rambosed J (1995) Sequence and molecular characterization of a DNA region encoding the dibenzothiophene desulfurization operon of Rhodococcus sp. strain IGTS8. Appl Environ Microbiol 61:468–475

    CAS  Google Scholar 

  • Segel IH (1975) Enzyme kinetics. Wiley, New York

    Google Scholar 

  • Shafi R, Hutchings GJ (2000) Hydrodesulfurization of hindered dibenzothiophenes: an overview. Catal Today 59:423–442

    Article  CAS  Google Scholar 

  • Shavandi M, Sadeghizadeh M, Khajeh K, Mohebali G, Zomorodipour A (2010) Genomic structure and promoter analysis of the dsz operon for dibenzothiophene biodesulfurization from Gordonia alkanivorans RIPI90A. Appl Microbiol Biotechnol 87(4):1455–1461

    Article  CAS  Google Scholar 

  • Tanaka Y, Matsui T, Konishi J, Maruhashi K, Kurane R (2002) Biodesulfurization of benzothiophene and dibenzothiophene by a newly isolated Rhodococcus strain. Appl Microbiol Biotechnol 59:325–328

    Article  CAS  Google Scholar 

  • Wang SJ (2006) Sulfur species in diesels and their desulfurization reactivates. Master dissertation (in Chinese)

  • Wang MD, Li W, Shi Y, Wang DH, Feng H (2006) Effects of surfactant on biodesulfurization by Corynebacterium sp. ZD-1 in the presence of organic phase. J Zhejiang Univ Sci A 7:371–375

    Article  Google Scholar 

  • Xu P, Yu B, Li FL, Cai XF, Ma CQ (2006) Microbial degradation of sulfur, nitrogen and oxygen heterocycles. Trends Microbiol 14:398–405

    Article  CAS  Google Scholar 

  • Xu P, Feng J, Yu B, Li F, Ma C (2009) Recent developments in biodesulfurization of fossil fuels. Adv Biochem Eng/Biotechnol 113:255–274

    CAS  Google Scholar 

  • Yin CL, Zhao HJ, Xu YQ, Xin JX, Zhao RY, Liu CG (2007) Study on transformation of sulfides in the process of deep hydrodesulfurization of diesel. J China Univ Petrol 31:134–138 (in Chinese)

    CAS  Google Scholar 

  • Yu B, Xu P, Zhu SS, Cai XF, Wang Y, Li L, Li FL, Liu XY, Ma CQ (2006) Selective biodegradation of S and N heterocycles by a recombinant Rhodococcus erythropolis strain containing carbazole dioxygenase. Appl Environ Microbiol 72:2235–2238

    Article  CAS  Google Scholar 

  • Zhang Q, Tong MY, Li YS, Gao HJ, Fang XC (2007) Extensive desulfurization of diesel by Rhodococcus erythropolis. Biotechnol Lett 29:123–127

    Article  Google Scholar 

Download references

Acknowledgments

This research work was sponsored by the National Natural Science Foundation of China (No. 20276068).

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Correspondence to Wei Li.

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Zhang, SH., Chen, H. & Li, W. Kinetic analysis of biodesulfurization of model oil containing multiple alkyl dibenzothiophenes. Appl Microbiol Biotechnol 97, 2193–2200 (2013). https://doi.org/10.1007/s00253-012-4048-6

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  • DOI: https://doi.org/10.1007/s00253-012-4048-6

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