Effect of Alkyl Side Chain Location and Cyclicity on the Aerobic Biotransformation of Naphthenic Acids

被引:21
|
作者
Misiti, Teresa M. [1 ]
Tezel, Ulas [1 ,2 ]
Pavlostathis, Spyros G. [1 ]
机构
[1] Georgia Inst Technol, Sch Civil & Environm Engn, Atlanta, GA 30332 USA
[2] Bogazici Univ, Inst Environm Sci, TR-34342 Istanbul, Turkey
关键词
RESONANCE MASS-SPECTROMETRY; PROCESS-AFFECTED WATERS; OIL SANDS TAILINGS; ELECTROSPRAY-IONIZATION; WASTE-WATER; AQUATIC ENVIRONMENTS; CARBOXYLIC-ACID; ACUTE TOXICITY; BIODEGRADATION; DEGRADATION;
D O I
10.1021/es501058q
中图分类号
X [环境科学、安全科学];
学科分类号
08 ; 0830 ;
摘要
Aerobic biodegradation of naphthenic acids is of importance to the oil industry for the long-term management and environmental impact of process water and wastewater. The effect of structure, particularly the location of the alkyl side chain as well as cyclicity, on the aerobic biotransformation of 10 model naphthenic acids (NAs) was investigated. Using an aerobic, mixed culture, enriched with a commercial NA mixture (NA sodium salt; TCI Chemicals), batch biotransformation assays were conducted with individual model NAs, including eight 8-carbon isomers. It was shown that NM with a quaternary carbon at the alpha- or beta-position or a tertiary carbon at the beta- and/or beta-position are recalcitrant or have limited biodegradability. In addition, branched NM exhibited lag periods and lower degradation rates than nonbranched or simple cyclic NM. Two NA isomers used in a closed bottle, aerobic biodegradation assay were mineralized, while 21 and 35% of the parent compound carbon was incorporated into the biomass. The NA biodegradation probability estimated by two widely used models (BIOWIN 2 and 6) and a recently developed model (OCHEM) was compared to the biodegradability of the 10 model NM tested in this study as well as other related NM. The biodegradation probability estimated by the OCHEM model agreed best with the experimental data and was best correlated with the measured NA biodegradation rate.
引用
收藏
页码:7909 / 7917
页数:9
相关论文
共 50 条
  • [1] Effects of Alkyl Chain Branching on the Biotransformation of Naphthenic Acids
    Smith, Benjamin E.
    Lewis, C. Anthony
    Belt, Simon T.
    Whitby, Corinne
    Rowland, Steven J.
    [J]. ENVIRONMENTAL SCIENCE & TECHNOLOGY, 2008, 42 (24) : 9323 - 9328
  • [2] Aerobic biotransformation potential of a commercial mixture of naphthenic acids
    Misiti, Teresa M.
    Tezel, Ulas
    Tandukar, Madan
    Pavlostathis, Spyros G.
    [J]. WATER RESEARCH, 2013, 47 (15) : 5520 - 5534
  • [3] Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching
    Richard J Johnson
    Ben E Smith
    Paul A Sutton
    Terry J McGenity
    Steven J Rowland
    Corinne Whitby
    [J]. The ISME Journal, 2011, 5 : 486 - 496
  • [4] Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching
    Johnson, Richard J.
    Smith, Ben E.
    Sutton, Paul A.
    McGenity, Terry J.
    Rowland, Steven J.
    Whitby, Corinne
    [J]. ISME JOURNAL, 2011, 5 (03): : 486 - 496
  • [5] Aerobic biotransformation of alkyl branched aromatic alkanoic naphthenic acids via two different pathways by a new isolate of Mycobacterium
    Johnson, Richard J.
    West, Charles E.
    Swaih, Aisha M.
    Folwell, Ben D.
    Smith, Ben E.
    Rowland, Steven J.
    Whitby, Corinne
    [J]. ENVIRONMENTAL MICROBIOLOGY, 2012, 14 (04) : 872 - 882
  • [6] Characterization of recalcitrant intermediates from biotransformation of the branched alkyl side chain of nonylphenol ethoxylate surfactants
    Di Corcia, A
    Costantino, A
    Crescenzi, C
    Marinoni, E
    Samperi, R
    [J]. ENVIRONMENTAL SCIENCE & TECHNOLOGY, 1998, 32 (16) : 2401 - 2409
  • [7] Biotransformation of linear alkylbenzene sulfonate (LAS) by Phanerochaete chrysosporium : oxidation of alkyl side-chain
    Jagjit S. Yadav
    David L. Lawrence
    Barbara A. Nuck
    Thomas W. Federle
    C. Adinarayana Reddy
    [J]. Biodegradation, 2001, 12 : 443 - 453
  • [8] Biotransformation of linear alkylbenzene sulfonate (LAS) by Phanerochaete chrysosporium:: oxidation of alkyl side-chain
    Yadav, JS
    Lawrence, DL
    Nuck, BA
    Federle, TW
    Adinarayana-Reddy, C
    [J]. BIODEGRADATION, 2001, 12 (06) : 443 - 453
  • [9] Effect of the Alkyl Side Chain on the Helical Conformation of Dialkylpolysilane Copolymers
    Tang Xianhui
    Ji Xingxing
    Qian Kai
    Li Yi
    Yang Yonggang
    [J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2014, 35 (11): : 2481 - 2486
  • [10] Anionic polymerizations of oligo(ethylene glycol) alkyl ether methacrylates:: Effect of side chain length and ω-alkyl group of side chain on cloud point in water
    Ishizone, Takashi
    Seki, Akiko
    Hagiwara, Mamoru
    Han, Seok
    Yokoyama, Hideaki
    Oyane, Ayako
    Deffieux, Alain
    Carlotti, Stephane
    [J]. MACROMOLECULES, 2008, 41 (08) : 2963 - 2967