Chemistry
Benzanthracene
Benzanthracene is a polycyclic aromatic hydrocarbon consisting of three fused benzene rings. It is a yellowish, crystalline compound that is used in research as a model for studying the carcinogenicity of polycyclic aromatic hydrocarbons. Benzanthracene is also a potential environmental pollutant due to its presence in fossil fuels and its release during incomplete combustion processes.
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eBook - ePubBiochemistry
An Organic Chemistry Approach
- Michael B. Smith(Author)
- 2020(Publication Date)
- CRC Press(Publisher)
, 35, 7731–7742. Copyright 1996 American Chemical Society.9.10 Polynuclear Aromatic Hydrocarbons
There are many aromatic compounds that meet the 4n +2 rule, with structures where the π-electrons are not confined to one ring, but rather contained in several rings that are fused together. They are called polynuclear (or polycyclic) aromatic molecules . Three simple examples are shown: naphthalene, anthracene, and phenanthrene. Naphthalene is a bicyclic aromatic compound with the formula C10 H8 . It was the main constituent of “mothballs” for many years, but toxicity led to its replacement with 1,4-dichlorobenzene (characterized as an insecticidal fumigant). Anthracene is a polycyclic aromatic compound (14 π-electrons) with three rings are fused together and the formula C14 H10 . Anthracene is used to prepare other important compounds and is used in wood preservatives and in insecticides. Phenanthrene is an isomer of anthracene in which the point of attachment of the “third ring” on the “middle ring” is different. Like anthracene, phenanthrene is derived from coal tar and is used in the synthesis of dyes, explosives, and drugs.Polynuclear aromatic hydrocarbons (e.g., naphthalene, anthracene, and phenanthrene) undergo electrophilic aromatic substitution reactions in the same manner as benzene. A significant difference is that there are more carbon atoms, more potential sites for substitution, and more resonance structures to consider in the arenium ion intermediates. The reaction of naphthalene with Cl2 /AlCl3 gave 1-chloronaphthalene as the major product, one of only two different positions for substitution, C1 and C2. Chlorination of naphthalene at C1 leads to the arenium ion shown in Figure 9.16
eBook - ePub- James G. Speight(Author)
- 2010(Publication Date)
- Gulf Professional Publishing(Publisher)
Anthracene exposure can cause skin and eye irritation, which can be aggravated by sunlight. Repeated exposure may cause alteration of skin pigments as well as cancerous growth, although there are no carcinogenic data for anthracene. Inhaled anthracene can cause bronchitis-like symptoms. There is limited information on human reproductive implications. Anthracene may cause genetic mutations in cells. Anthracene is not currently considered a toxic substance.Phenanthrene is an isomer of anthracene and, as a result, many of the physical properties of the two are very similar.The major differences between anthracene and phenanthrene lie in the melting point and the properties directly related to solubility (Table 13.2 ). Phenanthrene is purified as brown to white monoclinic crystals, and also has the characteristic faint aromatic smell.Like anthracene, phenanthrene is used in the production of dyes. It is also used in the manufacture of explosives, and is an important starting material for phenanthrene-based drugs. This leads directly to use in biochemical research for the pharmaceutical industry. A mixture of phenanthrene and anthracene tar is used to coat water storage tanks to prevent rust.Phenanthrene is also a skin and eye irritant, with increasing effects in sunlight due to photosensitization. There are currently no data available for human oral and inhalation exposure. It is, however, a suspected carcinogen and, although there are no data for humans, it is best to err on the side of caution and suspect carcinogenic effects will be present (Harvey, 1991 ).Benzo[a]pyrene (3,4-benzpyrene) is the largest of the four compounds, with five rings. It also has the faint aromatic odor. Pure benzo[a]pyrene is pale yellow, and is found as monoclinic or orthorhombic crystals. These can be separated from a mixture of polynuclear aromatic hydrocarbons using various standard separation techniques, and recrystallized from benzene and methanol. Benzo[a]pyrene is one of several compounds that is a known human carcinogen.
eBook - ePubImage and Reality
Kekulé, Kopp, and the Scientific Imagination
- Alan J. Rocke(Author)
- 2010(Publication Date)
- University of Chicago Press(Publisher)
The very next year Hofmann’s student William Perkin discovered mauve, the first coal tar dye. Aromatic compounds thereafter became the object of intense commercial interest, even though the structural details of their molecules were not yet known. Today, the overwhelming majority of the millions of known organic substances contain the benzene nucleus somewhere in their structure and therefore are aromatic in the chemical sense (organic compounds of all kinds comprise about 99 percent of known chemical compounds). Consequently, a satisfying scientific understanding of the constitution of benzene, and thus of all aromatic compounds, was historically of crucial importance to the development of chemistry, both pure and applied.Of course, this judgment is made only with hindsight, and before 1850 it was not obvious that aromatic substances were as important as that, nor even that the relevant substances should be considered as members of a common family. Others besides Liebig and Wöhler studied aromatic substances in the 1830s, including Berzelius, Mitscherlich, Dumas, and Laurent. Laurent called benzene “phène,” from the Greek for illumination, hence the modern name of the “phenyl” radical, C6 H5 (benzene less one hydrogen atom), and “phenol,” C6 H5 OH (phenyl hydroxide, or carbolic acid). It soon became clear that benzoic acid was phenyl carboxylic acid, C6 H5 CO2 H, and that its relatives in the benzoyl series all contained the phenyl radical. In the late 1840s Hofmann and his English students at the Royal College of Chemistry took the lead in these studies. Hofmann himself had carried out the first investigation of the components of coal tar, many of which were aromatic, and his student Charles Mansfield continued this work, focusing especially on benzene, toluene (which is methyl benzene), nitrobenzene, and aniline (aminobenzene).4It was in the late 1850s, simultaneous with the rise of the coal tar dye industry, that aromatic chemistry became a recognized subfield of organic chemistry. In the course of this chapter, we will see that the development of the structural theory of aromatic substances is an outstanding example of the heuristic importance, indeed indispensability, of visual symbols and mental images in the pursuit of chemical science.
eBook - ePubHandbook of Environmental Analysis
Chemical Pollutants in Air, Water, Soil, and Solid Wastes, Third Edition
- Pradyot Patnaik(Author)
- 2017(Publication Date)
- CRC Press(Publisher)
37 Hydrocarbons, Polynuclear AromaticPAHs are aromatic compounds that contain two or more benzene rings that are fused together. These substances may be analyzed by HPLC, GC, GC/MS, and enzyme immunoassay techniques. The latter is a rapid screening method that may be applied for a qualitative or semiquantitative determination. Test kits are commercially available for such screening. The U.S. EPA (1995) has specified a method (Draft Method 4035) that detects a range of PAHs to different degrees and measures the composite of individual responses to determine the total PAHs in the sample.The U.S. EPA has listed 16 PAHs as priority pollutants in wastewater and 24 PAH in the category of soils, sediments, hazardous wastes, and groundwater. Some common PAH compounds including the ones listed by the U.S. EPA as priority pollutants are presented in Table 37.1 . All these analytes, as well as any other compound that has a polyaromatic ring, may be analyzed by similar methods. The analytical steps include extraction of the sample with methylene chloride or an appropriate solvent, concentration of the solvent extract into a small volume, cleanup of the extract using silica gel (for dirty samples), and determination of PAH by HPLC, GC, or GC/MS. The HPLC method is superior to packed column GC analysis that suffers from a coelution problem.Table 37.1 Common PAHsCAS No. Compounds [83-32-9] Acenaphthene [208-96-8] Acenaphthylene [120-12-7] Anthracene [53-96-3] 2-Acetylaminofluorene [56-55-3] Benz(a )anthracene[205-99-2] Benzo(b )fluoranthene[207-08-9] Benzo(k )fluoranthene[191-24-2] Benzo(g ,h ,i )perylene[50-32-8] Benzo(a )pyrene[192-97-2] Benzo(e )pyrene[90-13-1] 1-Chloronaphthalene [91-58-7] 2-Chloronaphthalene [218-01-9] Chrysene [191-07-1] Coronenea[224-42-0] Dibenz(a ,j )acridine[53-70-3] Dibenz(a ,h )anthracene[132-64-9] Dibenzofuran [192-65-4] Dibenzo(a ,e
- Michael J. Kennish(Author)
- 2017(Publication Date)
- CRC Press(Publisher)
Reported values range from approximately 0.01 to greater than 5000 μg/kg dry weight for individual PAH contaminants. Elevated concentrations of PAHs in marine organisms often occur in areas receiving chronic hydrocarbon discharges. 4 CHEMICAL STRUCTURE Polycyclic aromatic hydrocarbons are a group of compounds consisting of hydrogen and carbon arranged in the form of two or more fused aromatic (benzene) rings in linear, angular, or cluster arrangements with unsubstituted groups possibly attached to one or more rings. 7 The compounds range from naphthalene (C 10 H g, two rings) to coronene (C 24 H 12, seven rings). 8 Common PAH compounds include six two-ring compounds (biphenyl, naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, 2,6-dimethylnaphthalene, and acenaphthene); three-ring compounds (flourene, phenanthrene, 1-methylphenanthrene, and anthracene); four-ring compounds (flouran- thene, pyrene, and benz[a]anthracene); and five-ring compounds (chrysene, benzo[a]pyrene, benzo[e]pyrene, perylene, and dibenz[a, h] anthracene). Together, PAHs comprise a homologous series of fused-aromatic ring compounds of increasing environmental concern. 9 The low-molecular-weight PAH (LMWpah) compounds, containing two or three rings, are acutely toxic but noncarcinogenic to a broad spectrum of marine organisms. The high-molecular-weight PAH (HMWpah) compounds, containing four, five, and six rings, are less toxic but have greater carcinogenic potential. 7, 10 Hence, the LMWpah compounds are sometimes classified separately from the HMW-pah varieties. Examples of LMWpah compounds that tend to be toxic are anthracene, fluorene, naphthalene, and phenanthrene
eBook - ePub- Roger O. McClellan(Author)
- 2017(Publication Date)
- CRC Press(Publisher)
J. Chromatogr., 256, 81, 1983.19 . Ciccioli, P., Brancaleoni, E., Cecinato, A., DiPalo, C., Buttini, P., and Liberti, A., Fractionation of polar polynuclear aromatic hydrocarbons present in industrial emissions and atmospheric samples and their determination by gas chromatography-mass spectrometry, J. Chromatogr., 351, 451, 1986.20 . Cautreels, W. and Van Cauwenberghe, K., Determination of organic compounds in airborne particulate matter by gas chromatography mass spectrometry, Atmos. Environ., 10, 447, 1976.21 . Warshawsky, D., unpublished data.22 . Armstrong, E. C. and Bonser, G. M., Squamous carcinoma of the forestomach and other lesions in mice following oral administration of 3,4,5,6-dibenzcarbazole, Br. J. Cancer, 4, 203, 1950.23 . Boyland, E. and Brues, A. M., The carcinogenic action of dibenzcarbazoles, Proc. R. Soc. London, Ser. B, 122, 429, 1937.24 . Strong, L. C., Smith, G. M., and Gardner, W. J., Induction of tumors by 3,4,5,6-dibenzcarbazole in male mice of the CBA strain, which develops spontaneous hepatoma, Yale J. Biol. Med., 10, 335, 1938.25 Kirby, A. H. M. and Peacock, P. R., The influence of methylation on carcinogenic activity. I. N-methyl-3,4,5,6-dibenzcarbazole, Brit. J. Exp. Pathol., 27, 179, 1946.26 . Kirby, A. H. M., The carcinogenic activity of N-ethyl-3,4,5,6-dibenzcarbazole. Bio-chem. J., 1, 42, 1948.27 . Bonser, G. M., Clayson, D. B., Jell, J. W., and Pyrah, L. N., The carcinogenic properties of 2-amino-1-naphthol hydrochloride and its parent amine 2-naphthylamine, Br. J. Cancer, 6, 412, 1954.28 . Buu-Hoi, N. P., New developments in chemical carcinogenesis by polycyclic hydrocarbons and related heterocycles: a review, Cancer Res., 24, 1511, 1964.29 . Lacassagne, A., Buu-Hoi, N., Zajdela, F., and Xuong, N. D., Relations entre la structure moléculaire et l’activite cancerogene dans la serie du carbazole, Bull. Cancer, 42, 1, 1955.30 . Andervont, H. G. and Edwards, J. E., Hepatic changes and subcutaneous and pulmonary tumors induced by subcutaneous injection of 3,4,5,6-dibenzcarbazole, JNCI
eBook - ePub- Debasis Bagchi, Anand Swaroop, Debasis Bagchi, Anand Swaroop(Authors)
- 2016(Publication Date)
- CRC Press(Publisher)
Environ. Res. 32: 104–110.IPCS. 1998. Environmental Health Criteria 202: Selected non-heterocyclic polycyclic aromatic hydrocarbons. International Programme on Chemical Safety, World Health Organization, Lyon, France.Iqbal, J. and M.M. Hussain. 2009. Intestinal lipid absorption. Am. J. Physiol. Endocrinol. Metab. 296:E1183–E1194.Iwegbue, C.M.A. and F.I. Bassey. 2013. Concentrations and health hazards of polycyclic aromatic hydrocarbons in selected commercial brands of milk. Food Measure 7: 177–184.Jedrychowski, W., Perera, FP., Tang, D., Stigter, L., Mroz, E., Flak, E., Spengler, J., Budzyn-Mrozek, D., Kaim, I., and R. Jacek. 2012. Impact of barbecued meat consumed in pregnancy on birth outcomes accounting for personal prenatal exposure to airborne polycyclic aromatic hydrocarbons: Birth cohort study in Poland. Nutrition 28: 372–377.Johnson, L.R. 2001. Gastric secretion. In Gastrointestinal Physiology, 6th edn., ed. L.R. Johnson. St. Louis, MI: Mosby Publishing.Jurjanz, S., Rychen, G., and C. Feidt. 2008. Dairy livestock exposure to persistent organic pollutants and their transfer to milk: A review. In Impact of Pollution on Animal Products, eds. B. Faye and Y. Sinyavskiy, pp. 63–83. Dordrecht, the Netherlands: Springer Science and Business Media.Kawamura, Y., Kamata, E., Ogama, Y. et al. 1988. The effect of various foods on the intestinal absorption of benzo(a)pyrene in rats. J. Food Hyg. Soc. Jpn. 29: 21–25.Kazerouni, N., Sinha, R., Hsu, C.H., Greenberg, A., and N. Rothman. 2001. Analysis of 200 food items for benzo[a]pyrene and estimation of its intake in an epidemiologic study. Food Chem. Toxicol. 39: 423–436.Khan, S., Cao, Q., Lin, A.J., and Y.G. Zhu. 2008. Concentrations and bioaccessibility of polycyclic aromatic hydrocarbons in wastewater-irrigated soil using in vitro gastrointestinal test. Environ. Sci. Pollut. Res. Int. 15: 344–353.Kim, J., Koo, S.I., and S.K. Noh. 2012. Green tea extract markedly lowers the lymphatic absorption and increases the biliary secretion of 14C-benzo[a]pyrene in rats. J. Nutr. Biochem
