Chemistry
Fluoranthene
Fluoranthene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings. It is a yellowish, crystalline compound that is found in coal tar and is produced during the incomplete combustion of organic materials. Fluoranthene is used as a chemical intermediate and is also of interest due to its potential environmental impact and health effects.
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eBook - ePubEnvironmental Carcinogens
Polycyclic Aromatic Hydrocarbons
- G. Grimmer(Author)
- 2018(Publication Date)
- CRC Press(Publisher)
According to Rules 2, 3, and 4, Fluoranthene is oriented, numbered, and lettered as follows:whereas, according to Rule 2, the orientation of BjF and BkF does not have to be changed after the attachment of the benzene ring, the structural formulas of BaF and BbF have to be reoriented:Note: Benzo[a ]Fluoranthene is a synonym of benz[a ]aceanthrylene. The same applies to benzo[b ]Fluoranthene and benz[e ]acephenanthrylene. According to Rule 1 the second designation is to be preferred in both cases, since the base component “Fluoranthene” is given first.Some of the PAH listed in Tables 13 and 14 are available at a purity of 99% (and more) from the Commission of the European Communities, Community Bureau of Reference BCR, Rue de la Loi 200, B-1049 Brussels, Belgium.2.3 Methods of PAH Detection
2.3.1 Introduction
Today there are two methods for assessing the carcinogenic properties of environmental samples:- The chronic toxic testing of these samples, using appropriate experimental animals
- The chemical analysis of the carcinogenic constituents of samples, so far as these are known
The testing of samples, or a suitable extract, in animal experiments for carcinogenic properties is carried out by feeding, topical application, subcutaneous injection, intratracheal application, etc. and, if suitable doses are used, gives clear evidence of tumor-producing properties. The evidence obtained in animal experiments covers all the classes of carcinogenic substances contained in the suspected sample if they exhibit activity in the chosen experimental animal model (e.g., PAH, nitrogen-containing polycyclic aromatic compounds, nitrosamines, aromatic amines, mycotoxins, or carcinogenic inorganic compounds). The disadvantages of this test system are the long duration of the experiments (several months) and the correspondingly high costs.For the chemical analysis, it is necessary that the substances inducing malignant tumors in animal experiments are known. Not all PAH cause cancer. Consequently, all compounds belonging to a class of noxious substances have to be tested in several animal models in order to assess their activity. In the case of the several hundred PAH, such comparative investigations are hardly feasible. Economic reasons demand a restriction to those PAH which occur most frequently and in highest concentrations in the environment.
- 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- Debasis Bagchi, Anand Swaroop, Debasis Bagchi, Anand Swaroop(Authors)
- 2016(Publication Date)
- CRC Press(Publisher)
There has been a burgeoning public awareness about the consumption of healthy, nutritious food and staying fit. Furthermore, there is a mounting concern about food safety from the standpoint of microbial contamination and contamination by a variety of chemicals. These chemicals have been shown to occur as natural toxicants in produce (glycoalkaloids, glucosinolates, saponins, illudane sesquiterpenes, etc.) or those used during pre- and postharvest of agricultural crops, fruits, and vegetables (agrochemicals). Other chemical contaminants include feed supplements for livestock and industrial chemicals (chlorinated hydrocarbons, polycyclic aromatic hydrocarbons [PAHs], heterocyclic amines, phthalates, heavy metals, etc., as reviewed in Creaser and Purchase [1991] and D’Mello [2003]). Therefore, from a food safety and regulatory perspective, monitoring of foodstuffs for chemical residues is warranted. From a human health standpoint, the processes by which these chemicals are absorbed through the gastrointestinal (GI) tract and cause toxicity and/or cancer are also important. Because there are several hundreds of food toxicants belonging to various chemical classes with differing physicochemical properties and environmental loadings, it is beyond the scope of this chapter to deal with each chemical class and address their absorption processes and the factors that influence these processes. Therefore, in this treatise, we will focus on the absorption of PAH family of toxicants. These compounds that are environmental and dietary toxicants are also implicated as causative agents for lung, breast, and colon cancers and cause toxicity to the nervous, reproductive, developmental, and cardiovascular systems (for comprehensive reviews refer to WHO, 2010; Ramesh et al., 2011).FIGURE 5.1 Some representative polycyclic aromatic hydrocarbon compounds.PAHs are a large family of environmental toxicants characterized by two or more fused aromatic rings. These compounds are formed as a result of pyrolytic (incomplete combustion of organic materials during industrial and other human activities such as coal-fired power generation, refuse burning, wild fires, etc.) and petrogenic (drilling for petroleum, crude oil deliveries, etc.) processes. Other sources for PAH contamination of the environment and exposure to humans include industrial and automobile emissions, hazardous waste sites, arson, and warfare (IPCS, 1998; Ramesh et al., 2004; Hood et al., 2009). Being semivolatile, sparingly water-soluble, lipophilic, and high-molecular-weight compounds, these pollutants are pervasive in the environment and depending on their loading may persist in soil and sediments as mixtures (Ramesh et al., 2011). A few representative PAHs that are encountered in the environment are shown in Figure 5.1
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
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.
- Leo M. L. Nollet, Leo M. L. Nollet(Authors)
- 2011(Publication Date)
- Wiley-Blackwell(Publisher)
Chapter 19 Polycyclic Aromatic Hydrocarbons Peter Šimko Polycyclic aromatic hydrocarbonsOne of the most important groups of chemicals that are actually harmful to human health is the group of polycyclic aromatic hydrocarbons (PAHs). They are characterized by two or more condensed aromatic rings in a molecular structure and have a strong lipophilic character. PAHs are formed during the thermal decomposition of organic mass such as fuel, wood, and coal, especially at limited access of oxygen in the range of 500°C–900°C (Bartle 1991). Alternatively, they are also contained in crude oil, and during accidents they enter directly into the environment and become direct sources of pollution. The temperature of smoke formation plays a decisive role because the amounts of PAH contained in smoke increase linearly with the temperature of smoke generation in the interval of 400°C–1000°C (Tóth and Blaas 1972). In the prehistoric past, humans probably hung their catch over the fire to protect it from scavengers, and from this time smoking was widely used not only for production of smoked products with a special organoleptic profile but also for preservation effects by inactivating enzymes and microorganisms. So far, techniques of smoking have gradually improved, and various procedures have been developed in different regions for treating meat, cheese, and fish. Today, the technology is used mainly for enrichment of foods with specific characteristics (taste, odor, and appearance) that are popular in the market (Šimko 2005). However, PAHs are also formed upon direct thermal meat treatments such as roasting, grilling, and frying. Fat is the main source of hydrocarbons, and formation of PAHs during charcoal broiling is directly dependent on the fat content of the meat. Melted fat from heated meat that drips onto the hot coals is thermally decomposed, giving rise to the formation of PAHs, which are then deposited on the meat surface as the smoke rises (Larsson et al. 1983). The seeddrying processes using direct firing for production of hot air can be responsible for major PAH contamination of some vegetable oils, such as coconut and grapeseed oils. Apart form the formation itself, the temperature also affects the structure and number of PAHs. The number of PAHs present in smoked fish can reach 100 compounds (Grimmer and Böhnke 1975) that have different effects on living organisms.
