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At least 19 recordsLinked to original sources
PubMed2005

Structural and ionization effects on the adsorption behaviors of some anilinic compounds from aqueous solution onto high-area carbon-cloth.

The adsorption of anilinic compounds; aniline, p-toluidine, 1-napthylamine and sodium salt of diphenylamine-4-sulfonic acid from solutions in H2O, in 1 M H2SO4 or in 0.1 M NaOH onto activated carbon-cloth was studied by in situ UV spectroscopy. A specially designed adsorption cell was used for this purpose. The adsorption processes were found to follow first-order kinetics and the rate constants were determined. The pH at the point of zero charge of the carbon-cloth surface was measured as 7.4. The highest rates and extents of adsorption were observed from H2O solutions for aniline, p-toluidine and 1-napthylamine and from solution in 1 M H2SO4 for the sodium salt of diphenylamine-4-sulfonic acid. The adsorption behaviors of these four anilinic compounds in the three solutions (in H2O, in 0.1 M NaOH and in 1 M H2SO4) were explained in terms of electrostatic and dispersion interactions between carbon-cloth surface and the anilinic species. The adsorption isotherm data for the anilinic compounds were derived at 30 degrees C and treated according to Langmuir and Freundlich models. The Freundlich model was found to represent the experimental isotherm data better than Langmuir model.

Adsorption↗
PubMed1975

Personal air sampling for vapors of aniline compounds.

A method has been developed for air sampling and laboratory analysis of vapors of seven aniline compounds: aniline, N,N-dimethylaniline, o-toluidine, 2,4-xylidine, panisidine, o-anisidine, and p-nitroaniline. Air is drawn by a personal sampling pump from a worker's breathing zone through a tube containing silica gel to collect any anilines present. In the laboratory each silica gel section is transferred to a glass-stoppered tube and desorbed with ethanol. An aliquot of this is analyzed by gas chromatography to determine the amount of each aniline compound present. The sampling tube can be used for short-term sampling at 1000 cm3/min or for sampling up to eight hours at 200 cm3/min. Maximum interference effects of water vapor have been considered. Results of retention, desorption, storage, accuracy, and precision studies are presented.

Absorption↗
PubMed2005

Equilibrium and kinetic studies on the adsorption of aniline compounds from aqueous phase onto bifunctional polymeric adsorbent with sulfonic groups.

In the present study, a hydrophilic bifunctional polymeric resin (LS-2) with sulfonic groups was synthesized, and the adsorption performance of three aniline compounds, aniline, 4-methylaniline, and 4-nitroaniline onto LS-2 was compared with that on the commercial Amberlite XAD-4. The uptake of the aniline compounds on LS-2 is a procedure of coexistence of physisorption and chemisorption and obeys the pseudo-second order rate equation, while the uptake of the compounds on XAD-4 is merely a physical adsorption and follows the pseudo-first order rate equation. All the isothermal data fit well with the Freundlich model, and the values of K(F) of the compounds adsorbing on LS-2 are much higher than those on XAD-4 suggesting the higher adsorbing capacities on LS-2 than those on XAD-4, which may be attributed to the microporous structure and the polar groups on the network of LS-2 resin. Dynamic adsorption and desorption studies for aniline on LS-2 show that the breakthrough adsorption capacity and the total adsorption capacity are 0.96 and 1.24 mmol per milliliter resin, respectively. Nearly 100% regeneration efficiency for the adsorbent was achieved by 5% hydrochloric acid.

Adsorption↗
PubMed1987

Perspectives on the mechanism of action of the splenic toxicity of aniline and structurally-related compounds.

Aniline and several structurally-related aromatic amines produce spleen tumours in rats given high doses of compound in 2-year bioassay studies. Evaluation of the pathogenesis of the splenic lesions and characterization of the disposition of radiolabelled aniline in animals suggests that the spleen tumours may be a secondary response resulting from chemically-mediated erythrocyte toxicity. It is proposed that compound-derived toxicity to erythrocytes results in scavenging of damaged red blood cells by the spleen, initiating a series of events which may contribute to the development of spleen tumours. These events potentially include (i) specific accumulation of the parent compound or toxic metabolite(s) carried to the spleen by erythrocytes; (ii) deposition of erythrocytic debris, particularly iron, which may catalyse tissue-damaging free-radical reactions; and (iii) induction of splenic hyperplasia resulting from erythrocyte overload. Linkage of the splenic tumorigenicity of these aromatic amines to an initial toxic event in the erythrocyte suggests that the carcinogenicity of such compounds may be determined by a definable threshold dose, i.e. the events leading to the carcinogenicity are not initiated until the capacity of the red blood cell to cope with the toxic insult is exceeded.

Aniline Compounds↗
PubMed1980

[Effect of thiol compounds on aniline toxicity and aniline metabolism].

The authors examined systematically the influence of some thiol compounds on the drug metabolism, investigating the effect of potassium ethylxanthogenate, diethyldithiocarbamata, inithiol and penicilamine on the aniline toxicity, methemoglobin formation and aniline-hydroxylase activity. They found that the examined compounds increased aniline toxicity in white male rats. These compounds inhibited aniline-hydroxilase activity. The connection between the increase of the toxicity of aniline under the influence of the examined compounds and their inhibiting action on the metabolism of aniline was discussed.

Aniline Compounds↗
PubMed1984

Nature of N-nitrosodimethylamine demethylase in hepatic microsomes of rats.

The nature of enzymes involved in demethylation of N-nitrosodimethylamine (NDMA) was investigated in hepatic microsomes of rats. Compared to the other cytochrome P-450-dependent enzymes. NDMA demethylase had anomalous properties as reported in the literature. However, kinetic analysis suggested a qualitative change in NDMA demethylase induced by phenobarbital (PB) and 3-methylcholanthrene (MC) pretreatment. The inhibition of demethylase by alpha-naphthoflavone in MC-treated microsomes also suggested that cytochrome P-450 species induced by MC are active in demethylating NDMA. The enhancement of NDMA demethylase activity by metyrapone in PB-treated microsomes was greater than in non-treated ones, and was not observed in MC-treated ones. The result is almost the same as in acetanilide hydroxylation, depending on cytochrome P-450. Pyrazole, tranylcypromine, and aminoacetonitrile, which are selective inhibitors of NDMA demethylation, interacted with cytochrome P-450 species to produce type-II spectra, and typical type-II compounds (aniline, imidazole, and nicotinamide) were inhibitors of the NDMA demethylation. Tranylcypromine irreversibly inhibited microsomal monoamine oxidase [EC 1.4.3.4], but not NDMA demethylase. Semicarbazide (a copper- and pyridoxal-containing amine oxidase [EC 1.4.3.6] inhibitor) had no effect on demethylation. From these results it is concluded that NDMA demethylation depends only on cytochrome P-450-dependent monooxygenases.

Aminoacetonitrile↗
PubMed2005

Degradation of industrial waste waters on Fe/C-fabrics. Optimization of the solution parameters during reactor operation.

This study addresses the pre-treatment of toxic and recalcitrant compounds found in the waste waters arriving at a treating station for industrial effluents containing chlorinated aromatics and non-aromatic compounds, anilines, phenols, methyl-tert-butyl-ether (MTBE). By reducing the total organic carbon (TOC) of these waste waters the hydraulic load for the further bacterial processing in the secondary biological treatment is decreased. The TOC decrease and discoloration of the waste waters was observed only under light irradiation in the reactor by immobilized Fenton processes on Fe/C-fabrics but not in the dark. The energy of activation for the degradation of the waste waters was of 4.2 kcal/mol. The degradation of the waste waters was studied in the reactor as a function of (a) the amount of oxidant used (H2O2), (b) the recirculation rate, (c) the solution pH and (d) the applied temperature. With these parameters taken as input factors, statistical modeling allows one to estimate the most economic use of the oxidant and electrical energy to degrade these waste waters. The concentration of the most abundant organic pollutants during waste waters degradation was followed by gas chromatography/mass spectrometry (GC-MS). The ratio of the biological oxygen demand to the total organic carbon BOD5/TOC increased significantly due to the Fe/C-fabric catalyzed treatment from an initial value of 2.03 to 2.71 (2 h). The reactor results show that the recirculation rate has no influence on the TOC decrease of the treated waters but affects the BOD increase of these solutions.

Aniline Compounds↗
PubMed2005

Involvement of proton transfer in the reductive repair of DNA guanyl radicals by aniline derivatives.

The most easily oxidized sites in DNA are the guanine bases, and major intermediates produced by the direct effect of ionizing radiation (ionization of the DNA itself) are electron deficient guanine species. By means of a radiation chemical method (gamma-irradiation of aqueous thiocyanate), we are able to produce these guanyl radicals in dilute aqueous solutions of plasmid DNA where the direct effect would otherwise be negligible. Stable modified guanine products are formed from these radicals. They can be detected in the plasmid conversion to strand breaks after a post-irradiation incubation with a DNA base excision endonuclease enzyme. If aniline compounds are also present, the yield of modified guanines is strongly attenuated. The mechanism responsible for this effect is electron donation from the aniline compound to the guanyl radical, and it is possible to derive rate constants for this reaction. Aniline compounds bearing electron withdrawing groups (e.g., 4-CF3) were found to be less reactive than those bearing electron donating groups (e.g., 4-CH3). At physiological pH values, the reduction of a guanyl radical involves the transfer of a proton as well as of an electron. The mild dependence of the rate constant on the driving force suggests that the electron is not transferred before the proton. Although the source of the proton is unclear, our observations emphasize the importance of an accompanying proton transfer in the reductive repair of oxidative damage to guanine bases which are located in a biologically active double stranded plasmid DNA substrate.

Acetophenones↗
PubMed2001

Storage time and deodorization temperature influence the formation of aniline-derived compounds in denatured rapeseed oils.

In 1981 an epidemic, named Toxic Oil Syndrome, occurred in Spain as a result of ingestion of rapeseed oil denatured with 2% aniline, which had been imported for industrial use but was fraudulently diverted and processed for human consumption. Two groups of chemical compounds have been identified in the ingested toxic oil: fatty acid anilides and amino-propanediol derivatives. The objective of this work was to assess the effect of several refining process variables on the formation of 3-(N-phenylamino)-1,2-propanediol (PAP) esters. The amount of PAP esters in aniline-denatured oil increased dramatically when oil was heated from 250 degrees C to 300 degrees C. However, the ones formed when 300 degrees C was reached were lost during processing at that temperature. The level maintained during the operation time at 300 degrees C was higher in denatured samples stored for 3 weeks before refining than in denatured samples stored only for 1 week. Anilides were also analyzed. We found that anilides decreased very little with distillation time. In this paper we discuss the influence of storage time prior to refining and of elevated refining temperature, such as temperatures that might occur in close proximity to a deodorizer coil.

Aniline Compounds↗
PubMed2006

Synthesis and HPLC evaluation of carboxylic acid phases on a hydride surface.

Three organic moieties containing carboxylic acid functional groups are attached to a particulate silica surface through silanization/hydrosilation. Two compounds (undecylenic acid and 10-undecynoic acid) have 11 carbon chains and the other is a five-carbon acid (pentenoic acid). Bonding is confirmed through carbon elemental analysis, diffuse reflectance infrared fourier transform spectroscopy, and carbon-13 and silicon-29 CP-MAS NMR spectroscopy. The bonded phases are tested by HPLC using PTH amino acids, nucleic acids, theophylline-related compounds, anilines, benzoic acid compounds, choline, and tobramycin. The latter two compounds are used to investigate the aqueous normal phase properties of the three bonded materials.

Amino Acids↗
PubMed1985

A quantum mechanical approach to the theory of cancer from polynuclear compounds. Metabolic activation and carcinogenicity of extended anilines and aminoazo compounds.

Calculations have been carried out of the electronic structure and molecular properties in relation to metabolic activation and carcinogenic activities of polycyclic aromatic amines (PAAs). Quantum mechanical molecular orbital method MINDO/3 is employed in the calculations mainly on anilines, extended anilines, and aminoazo and other azo compounds. The calculations, in agreement with findings of Arcos and Argus, indicate that for the highest level of carcinogenic activity obtainable with the dicyclic aromatic amines, the amino substituent must be introduced at the terminal carbon atom of the longest conjugate chain. In the case of monocyclic compounds, in particular, charge distribution of the amino substitution aids in identifying the carcinogenic character of the PAAs. Our results demonstrate that ring hydroxylation leads to detoxification of the compounds. However, the major pathway leading to carcinogenic activity involves transformation to hydroxylamines and subsequently to electrophilic arylnitrenium ions (ANIs). These are in line with findings from experiments. Calculations of certain electronic parameters give expected relative carcinogenic potencies. In all cases the ANIs function as ambient electrophiles which can undergo both electrostatic and covalent binding with nucleophilic centers of proteins and DNA bases.

Aniline Compounds↗
PubMed1989

Charge calculations in molecular mechanics 7: application to polar pi systems incorporating nitro, cyano, amino, C=S and thio substituents.

A previously described method for calculating partial atomic charges in molecules has been applied to a variety of different functional groups with pi electrons. The pi charges have been determined by varying the relevant Hükel coulombic and resonance integrals so as to reproduce the experimental dipole moments of known compounds. These include nitro, cyano, mercapto and thiocarbonyl compounds, anilines and a series of heterocyclic ring compounds involving nitrogen, oxygen and sulphur atoms. The calculated dipole moments are in good agreement with experimental values and are a considerable improvement on other calculated values, while requiring only a fraction of the computational time necessary for more rigorous methods. The resulting pi densities compare favourably with other theoretical (CNDO, MNDO and STO-3G) methods.

Amines↗
PubMedDate not supplied

Acute renal and hepatic effects induced by 3-haloanilines in the Fischer 344 rat.

Haloanilines are commonly used as chemical intermediates in the manufacture of a wide range of products. The purpose of this study was to examine the in vivo nephrotoxic and hepatotoxic potentials of the 3-haloanilines. The in vitro effects of the 3-haloanilines on renal function were also examined. In the in vivo experiments, male Fischer 344 rats (four rats/group) were administered a single intraperitoneal (i.p.) injection of an aniline hydrochloride (1.0 or 1.25 mmol kg-1) or vehicle. Renal and hepatic function were monitored at 24 and/or 48 h post-treatment. None of the 3-haloanilines were potent nephrotoxicants at either dose level. The greatest effects on renal function were observed following administration of 3-chloroaniline at a dose of 1.25 mmol kg-1 (oliguria, glucosuria, hematuria, decreased p-aminohippurate accumulation by renal cortical slices and increased blood urea nitrogen concentration). 3-Chloroaniline also was the only aniline compound to increase plasma ALT/GPT activity at 48 h. In the in vitro experiments, the ability of an aniline (10(-5) - 10(-3) M) to decrease organic ion accumulation in renal cortical slices from untreated rats was examined. The decreasing order of in vitro nephrotoxic potential was 3-iodoaniline > 3-bromoaniline > 3-chloroaniline > aniline > 3-fluoroaniline. These results indicate that the 3-haloanilines are not potent nephrotoxicants or hepatotoxicants at sublethal doses. In addition, the reasons why the 3-haloanilines have different orders of nephrotoxic potential in vivo and in vitro are not clear at this time.

Aniline Compounds↗
PubMedDate not supplied

Nitrification modelling in biofilms under inhibitory conditions.

A biofilm model has been developed for simulating nitrification in biofilms under inhibitory conditions. Nitrification inhibition has been modelled using uncompetitive inhibition kinetics. Inhibition kinetic experiments were performed by varying the bulk concentrations of inhibitory compound, aniline. Two sets of results were obtained with a nitrifying biofilm that was unacclimated to aniline and another which was acclimated to aniline. Fitting of the nitrification inhibition biofilm model to the experimental results yielded the nitrification inhibition constant, Ki, for aniline. Both the experiments yielded a value of about 3mg/L for Ki, which was similar to that obtained during nitrification inhibition experiments with suspended growth process carried out in an earlier study. The nitrification inhibition biofilm model is general and can be applied to nitrification inhibition with other toxic compounds.

Aniline Compounds↗
PubMed1983

The induction of bacterial mutation and hepatocyte unscheduled DNA synthesis by monosubstituted anilines.

A group of 45 monosubstituted aniline compounds was tested for the induction of point mutations in Salmonella typhimurium and Escherichia coli as well as for unscheduled DNA synthesis (UDS) in rat hepatocyte culture. Eleven compounds were bacterial mutagens, and five compounds induced UDS. Among these a correspondence between mutagenicity and UDS occurred for only two compounds (o-phenylenediamine and 4-aminobiphenyl), and these were also reported to be carcinogenic in rodents. Bacterial mutation was observed for one compound (p-phenylenediamine) not carcinogenic in rodents, and six suspect carcinogens were not detected in either test. In addition, eight compounds of unknown carcinogenic potential induced either bacterial mutation or UDS.

Aniline Compounds↗