benzofurans and naphthalene

Comamonas sp. JB was used to investigate the cometabolic degradation of dibenzofuran (DBF) and dibenzothiophene (DBT) with naphthalene as the primary substrate. Dehydrogenase and ATPase activity of the growing system with the presence of DBF and DBT were decreased when compared to only naphthalene in the growing system, indicating that the presence of DBF and DBT inhibited the metabolic activity of strain JB. The pathways and enzymes involved in the cometabolic degradation were tested. Examination of metabolites elucidated that strain JB cometabolically degraded DBF to 1,2-dihydroxydibenzofuran, subsequently to 2-hydroxy-4-(3'-oxo-3'H-benzofuran-2'-yliden)but-2-enoic acid, and finally to catechol. Meanwhile, strain JB cometabolically degraded DBT to 1,2-dihydroxydibenzothiophene and subsequently to the ring cleavage product. A series of naphthalene-degrading enzymes including naphthalene dioxygenase, 1,2-dihydroxynaphthalene dioxygenase, salicylaldehyde dehydrogenase, salicylate hydroxylase, and catechol 2,3-oxygenase have been detected, confirming that naphthalene was the real inducer of expression the degradation enzymes and metabolic pathways were controlled by naphthalene-degrading enzymes.

Topics: Benzofurans; Biotransformation; Catechols; Comamonas; Enzymes; Metabolic Networks and Pathways; Naphthalenes; Thiophenes

Topics: Benzofurans; Biodegradation, Environmental; Chryseobacterium; Environmental Pollutants; Escherichia coli; Hydrocarbons, Aromatic; Naphthalenes; Oxidoreductases; Pseudomonas fluorescens; Quinolones; Thiophenes

A series of treatment experiments were carried out to evaluate the applicability of a high-temperature melting treatment (GeoMelt process) to the destruction of polychlorinated naphthalene (PCN) formulation. We started with 10-kg-scale experiments in which a small melting furnace was used and then scaled up to a 1-t-scale experiment in which a melting furnace that resembled an actual treatment system was used. These runs were evaluated whether destruction efficiency (DE) of total PCNs was more than 99.999% and whether concentrations of PCNs and polychlorinated dibenzo-p-dioxins/dibenzofurans (PCDDs/DFs) in vitrified materials, emission gas, and scrubber water were below the target levels. Because DE values and the target levels of PCNs and PCDDs/DFs in these runs were satisfactory, then we carried out a demonstrative experiment using the actual treatment system and confirmed destruction of PCNs. Based on good results of the demonstrative experiment, stock of PCN formulation was successfully treated continuously.

Topics: Benzofurans; Dibenzofurans, Polychlorinated; Dioxins; Equipment Design; Hot Temperature; Incineration; Naphthalenes; Polychlorinated Biphenyls

A naphthalene-utilizing bacterium, Arthrobacter sp. W1, was used to investigate the cometabolic degradation of carbazole (CA), dibenzofuran (DBF) and dibenzothiophene (DBT) using naphthalene as the primary substrate. Both the growing and washed cells of strain W1 could degrade CA, DBF, DBT, and naphthalene simultaneously and quickly. Inhibition kinetics confirmed that the presence of CA, DBF and DBT in the growing system would inhibit the cells growth and biodegradability of strain W1. The relationship between ln(C/C0) and time, and specific degradation rate and CA, DBF and DBT concentration could be described well by First-order and Michaelis-Menten kinetics. The treatment of real coking wastewater containing high concentration of phenol, naphthalene, CA, DBF, DBT and NH3-N was shown to be highly efficient by naphthalene-grown W1 coupling with activation zeolite. Toxicity assessment indicated the treatment of the coking wastewater by strain W1 coupling with activation led to less toxicity than untreated wastewater.

Topics: Arthrobacter; Benzofurans; Biodegradation, Environmental; Carbazoles; Coke; Kinetics; Naphthalenes; Thiophenes; Time Factors; Toxicity Tests; Vibrio; Wastewater; Water Pollutants, Chemical

Two methods are presented that were designed to circumvent the persistent problem of benzofuran formation and instead yield a spiroketal of the rubromycin family type. First, using an alternative disconnection, a hemiketal conjugate addition to a naphthaquinone electrophile was investigated. Synthesis of the requisite electrophile provided insight into the selective oxidation and functionalization of the naphthalene portion. Second, the electronic features of the isocoumarin ring system were adjusted, and the corresponding reactivity further supports the hypothesis that electron-rich isocoumarins are capable of spiroketalization. Robust, flexible syntheses from simple precursors were developed that allowed multiple reduced isocoumarins to be generated. Combined, the data presented herein give insight into the sensitivities of this family and illuminate other potential methods of spiroketalization. In addition, the convergent assembly of substrates containing different naphthaquinone and isocoumarin subunits highlights the utility of our 1,3-dipolar cycloaddition approach to generate analogs of these structures for SAR, as well as chemical reactivity studies.

Topics: Benzofurans; Electrons; Furans; Isocoumarins; Molecular Structure; Naphthalenes; Naphthoquinones; Spiro Compounds

Congeners are molecules based on the same carbon skeleton but different by the number of substituents and/or a substitution pattern. Various Persistent Organic Pollutants (POPs) exist in the environment as families of halogen substituted congeners and/or their hydroxyl and methoxy substituted derivatives. Numbers of possible congeners resulting from substitution of a parent POP molecule with only one type of chemical group are generally available. At the same time, numbers of mixed-substituent congeners have not been counted and presented yet, although there is an increasing interest in such as is the increasing number of research articles presenting results on already identified Cl-/Br-mixed type congeners and/or their HO-/CH(3)O-mixed metabolites. We have enumerated and counted possible mixed-substituent congeners of common POPs. This article presents the obtained numbers for congener families of benzene, naphthalene, biphenyl, diphenyl ether, dibenzo-p-dioxin, dibenzofuran, anthracene, pyrene and others and obtained by substitution of up to five chemical group types.

Topics: Anthracenes; Benzene; Benzofurans; Carbon; Dioxins; Environmental Monitoring; Environmental Pollutants; Molecular Structure; Naphthalenes; Organic Chemicals; Phenyl Ethers; Pyrenes

An emplaced source of coal tar creosote within the sandy Borden research aquifer has documented the long-term (5140 days) natural attenuation for this complex mixture. Plumes of dissolved chemicals were produced by the essentially horizontal groundwater flowing at about 9 cm/day. Eleven chemicals have been extensively sampled seven times using a monitoring network of approximately 280, 14-point multilevel samplers. A model of source dissolution using Raoult's Law adequately predicted the dissolution of 9 of 11 compounds. Mass transformation has limited the extent of the plumes as groundwater has flowed more than 500 m, yet the plumes are no longer than 50 m. Phenol and xylenes have been removed and naphthalene has attenuated from its maximum extent on day 1357. Some compound plumes have reached an apparent steady state and the plumes of other compounds (dibenzofuran and phenanthrene) are expected to continue to expand due to an increasing mass flux and limited degradation potential. Biotransformation is the major process controlling natural attenuation at the site. The greatest organic mass lost is associated with the high solubility compounds. However, the majority of the mass loss for most compounds has occurred in the source zone. Oxygen is the main electron acceptor, yet the amount of organics lost cannot be accounted for by aerobic mineralization or partial mineralization alone. The complex evolution of these plumes has been well documented but understanding the controlling biotransformation processes is still elusive. This study has shown that anticipating bioattenuation patterns should only be considered at the broadest scale. Generally, the greatest mass loss is associated with those compounds that have a high solubility and low partitioning coefficients.

Topics: Benzofurans; Biotransformation; Coal Tar; Creosote; Electrons; Kinetics; Models, Chemical; Naphthalenes; Oxygen; Phenanthrenes; Phenol; Soil Pollutants; Solubility; Time Factors; Xylenes

Topics: Animals; Behavior, Animal; Benzofurans; Cyclobutanes; Histamine H3 Antagonists; Humans; Male; Molecular Structure; Naphthalenes; Radioligand Assay; Rats; Receptors, Histamine H3; Trans-Activators; Transcriptional Regulator ERG

The reaction of o-alkynylbenzaldehydes 1 with different alcohols, silylated nucleophiles 5, electron-rich arenes 10, and heteroarenes 12 in the presence of the reagent IPy(2)BF(4), at room temperature, gave functionalized 4-iodo-1H-isochromenes 2, 6, 11, and 13 in a regioselective manner. When alkynes 16 and alkenes 19 and 20 were used as nucleophiles, a regioselective benzannulation reaction took place to form 1-iodonaphthalenes 17 and 1-naphthyl ketones 18, respectively. Moreover, the latter process has been adapted to accomplish the synthesis of indole, benzofuran, and benzothiophene derivatives (23, 27, and 28, respectively). The three patterns of reactivity observed for the o-alkynylbenzaldehyde derivatives with IPy(2)BF(4) stem from a common iodinated isobenzopyrylium ion intermediate, A, that evolves in a different way depending on the nucleophile present in the reaction medium. A mechanism is proposed and the different reaction pathways observed as a function of the type of nucleophile are discussed. Furthermore, the reaction of the o-hexynylbenzaldehyde 1 b with styrene was monitored by NMR spectroscopy. Compound III, a resting state for the common intermediate in the absence of acid, has been isolated. Its evolution in acid media has been also tested, thereby providing support to the proposed mechanism.

Topics: Aldehydes; Alkynes; Benzofurans; Benzopyrans; Heterocyclic Compounds; Indoles; Ions; Naphthalenes; Onium Compounds; Pyridines; Thiophenes

The homogeneous, gas-phase oxidative thermal degradation of a 50:50 mixture of 2-bromophenol and 2-chlorophenol was studied in a 1 cm i.d., fused silica flow reactor at a concentration of 88 ppm, with a reaction time of 2.0 s, over a temperature range of 300 to 1000 degrees C. Observed products in order of decreasing yield included the following: dibenzo-p-dioxin (DD), 4-bromo-6-chlorodibenzofuran (4-B,6-CDF), phenol, 4,6-dibromodibenzofuran (4,6-DBDF), 2,6-dibromophenol, 4,6-dichlorodibenzofuran (4,6-DCDF), 2-bromo-4-chlorophenol, 2,4-dibromophenol, 2-chloro-4-bromophenol, 4-monobromodibenzofuran (4-MBDF), 4-monochlorodibenzofuran (4-MCDF), dibenzofuran (DF), 1-monobromodibenzo-p-dioxin (1-MBDD), 1-monochlorodibenzo-p-dioxin (1-MCDD), 2,4,6-tribromophenol, naphthalene, chloronaphthalene, bromonaphthalene, chlorobenzene, bromobenzene, and benzene. The results are compared and contrasted with previous results reported for the oxidations of pure 2-chlorophenol and 2-bromophenol as well as results for the pyrolysis of the mixture of 2-chlorophenol and 2-bromophenol. 4,6-DBDF and 4,6-DCDF were observed in higher yields than under pyrolytic conditions but considerably less than the yields observed for the individual oxidation of 2-chlorophenol and 2-bromophenol. The effect on chlorine and bromine on the concentration of hydroxyl radical is shown to control the dioxin-to-furan ratio.

Topics: Benzofurans; Chlorophenols; Dioxins; Environment; Gases; Hydroxyl Radical; Models, Chemical; Naphthalenes; Oxygen; Phenols; Polychlorinated Dibenzodioxins; Temperature