Polycyclic aromatic hydrocarbon an overview sciencedirect. The air monitoring of polycyclic aromatic compounds pacs and pac transformation products, including nitrated polycyclic aromatic hydrocarbons npahs and oxygenated polycyclic aromatic hydrocarbons opahs was then linked to the potential toxicity of air. Polycyclic aromatic hydrocarbons pahs are a large group of organic compounds with two or more fused aromatic rings. Structure and nomenclature of aromatic compounds chemistry libretexts. This statement was prepared to give you information about polycyclic aromatic hydrocarbons. Mapping indicators of toxicity for polycyclic aromatic.
Lists of polycyclic aromatic hydrocarbons polycyclic. Pdf polycyclic aromatic hydrocarbons formation and occurrence. The chemical group of polycyclic aromatic compounds pac, including the betterknown subgroup of polycyclic aromatic hydrocarbons pah and the heterocyclic aromatic compounds nsopac, heterocycles, comprise several thousand individual compounds. Aug 12, 2019 aromatic compounds contain a benzene ring or have certain benzenelike properties. They also are produced when coal, oil, gas, wood, garbage, and tobacco are burned. Polycyclic aromatic compounds pacs represent a class of molecules consisting of two or more condensed aromatic rings. Polycyclic and heterocyclic aromatic compounds mcataid. Polycyclic aromatic hydrocarbons aromatic compounds can have rings that share a set of carbon atoms fused rings compounds from fused benzene or aromatic heterocyclic rings are themselves aromatic naphthalene. This document contains information for facilities which manufacture, produce, or otherwise use polycyclic aromatic compounds.
Most of the pahs with low vapour pressure in the air are adsorbed on particles. They have a relatively low solubility in water, but are highly lipophilic. By definition, polycyclic aromatic hydrocarbons have multiple cycles, precluding benzene from being considered a pah. Pdf polycyclic aromatic hydrocarbons pahs emerged as an important contaminant group in a gamut of processed food groups like dairy, nuts, herbs. They are a class of organic compounds consisting of two or more fused aromatic rings. Extracts of passive air samples collected from 15 passive sampling network sites across the athabasca oil sands region were used to explore the application of in vitro assays for mutagenicity salmonella mutation assays and cytotoxicity lactate dehydrogenase assay to assess the toxicity of the air mixture. Polycyclic aromatic hydrocarbons pahs are a group of more than 100 chemicals that are also called polynuclear aromatic hydrocarbons. Pdf polycyclic aromatic compounds pahs and oxygenated. Aromaticity in molecules with more than one ring page 2 b underlying question. Polycyclic aromatic hydrocarbons pahs were ranked as the ninth most threatening compounds to human health in 2001 king et al. Additional guidance on who must report, reportable quantities, and how to estimate annual releases can be found in the following sections.
Huckels rule is strictly for monocyclic aromatic compound, its application to polycyclic aromatic compounds is tenuous. Polycyclic aromatic hydrocarbons pahs what are pahs. Polycyclic aromatic compounds pahs and oxygenated pahs and trace metals in fish species from ghana west africa. Another way to consider pahs is molecules made by fusing two or more benzene rings. Polycyclic aromatic hydrocarbons pahs are a class of chemicals that occur naturally in coal, crude oil, and gasoline. For compounds that contain only aromatic carbons, values greater than 3. These rings share one or more sides and contain delocalized electrons. Catalytic condensation for the formation of polycyclic. The green pigment found in plants, more commonly known as chlorophyll, consists of aromatic hydrocarbons and is very important in the process of food production in plants. Heterocyclic and substituted polycyclic aromatic hydrocarbons 267 h.
It is an object of the present invention to provide a novel polycyclic aromatic compound and an organic electroluminescence device using the same. Understanding the reactivity of polycyclic aromatic. Nov 25, 2019 a polynuclear aromatic hydrocarbon is a hydrocarbon made up of fused aromatic ring molecules. Polycyclic aromatic compounds chemistry libretexts. Bahna l, podany v, benesova m, godal a, dufour m, jacquignon p, vachalkova a. This article examines the ecotoxicological effects of polycyclic aromatic hydrocarbons pahs. Method 5506, issue 3, dated 15 january 1998 page 3 of 9 niosh manual of analytical methods nmam, fourth edition sampling. Polycyclic aromatic hydrocarbons problem chemicals. Historically, benzenelike substances were called aromatic hydrocarbons because they had distinctive aromas. The peripheral carbon atoms numbered in all but the last three examples are all bonded to hydrogen atoms. May 31, 2017 what are polycyclic aromatic hydrocarbons pahs.
Includes only the 21 chemicals listed as components of this polycyclic aromatic compounds category, to be reported as the category and not as individual chemical substances. They are currently of great interest as potential semiconducting materials for organic field. By providing new polycyclic aromatic compounds in which multiple aromatic rings are connected by boron atoms and oxygen atoms, etc. The chemical group of polycyclic aromatic compounds pac, including the betterknown subgroup of polycyclic aromatic hydrocarbons pah and the heterocyclic aromatic compounds nsopac. Jan 21, 2015 this statement was prepared to give you information about polycyclic aromatic hydrocarbons pahs and to emphasize the human health effects that may result from exposure to them. Also known as pahs or polynuclear aromatic hydrocarbons. Mapping indicators of toxicity for polycyclic aromatic compounds in the atmosphere of the athabasca oil sands region narumol jariyasopit, tom harner, dongmei wu, andrew williams, sabina halappanavar, and ky su air quality processes research section, environment and climate change canada, toronto, ontario m3h 5t4, canada. Guidance for facilities reporting chemicals from the polycyclic aromatic compounds category under epcra section 3.
Toxicological profile for polycyclic aromatic hydrocarbons. Must i include all p orbitals in the closed loop, even if counting all predicts the molecule is nonaromatic or antiaromatic when counting just some would predict the molecule is aromatic. The term polycyclic aromatic hydrocarbon pah commonly refers to a large. Benzene rings may be joined together fused to give larger polycyclic aromatic compounds. A few examples are drawn below, together with the approved numbering scheme for substituted derivatives. Some of the numerous uses of aromatic hydrocarbons are listed below. Polycyclic aromatic hydrocarbons pahs polycyclic aromatic hydrocarbons pahs are a class of chemicals that occur naturally in coal, crude oil, and gasoline. The first draft of polynuclear aromatic hydrocarbons in drinkingwater, background document for the development of the who guidelines for drinkingwater quality, was prepared by j. An aromatic ring is an organic ring in which the electrons are delocalized. For some people, the primary exposure to pahs occurs in the workplace. These compounds comprise a distinct class, called aromatic hydrocarbons. Today, an aromatic compound is any compound that contains a benzene ring or has certain benzenelike properties but not necessarily a strong aroma. The sorption of aromatic hydrocarbons onto the gel is characterized by pseudofirstorder kinetics and henry isotherm, suggesting a physisorption mechanism. Compounds were not arbitrarily drawn and named simply to enumerate all possibleisomers.
Short for polycyclic aromatic hydrocarbons, pahs describe chemicals that are often found together in groups of two or more. Rockne department of civil and materials engineering mc 246, university of illinois, chicago, 842 west taylor street, chicago, illinois 606077023, usa received 4 october 2002. This public health statement is the summary chapter from the toxicological profile for polycyclic aromatic hydrocarbons pahs. Pdf polycyclic aromatic hydrocarbons pahs are a class of hazardous organic compounds consisting of three or more fused benzene rings. The second is a list of structural formulas ordered according to structural complexity and ratings of carcinogenic activity. The results show that the presence of maleic anhydridecyclodextrin and chitosan into hydrogels leads to an increase in the removal efficiency of the aromatic compounds. Aromatic hydrocarbons are compounds that contain a benzene ring. Total polycyclic aromatic compounds include the polycyclic aromatic hydrocarbons pahs. Despite knowing many polycyclic aromatic sulfur heterocycles pash, condensed ring.
The recent literature describing polycyclic aromatic hydrocarbons pahs in air, water, soil and sediment, waste sludge, biomonitoring, toxicity, are. Sep 27, 2019 polycyclic aromatic compounds pacs represent a class of molecules consisting of two or more condensed aromatic rings. Polycyclic aromatic hydrocarbons pahs fact sheet epa. Pdf overview of polycyclic aromatic compounds pac jan. Polycyclic aromatic hydrocarbons national toxicology program. All journal articles featured in polycyclic aromatic compounds vol 40 issue 1. Next we consider a class of hydrocarbons with molecular formulas like those of unsaturated hydrocarbons, but which, unlike the alkenes, do not readily undergo addition reactions.
Includes emission factors and examples of mixtures. The first is an alphabetical list of polycyclic aromatic hydrocarbons pahs discussed in the report and close chemical relatives, with molecular formulas and cas numbers. Polycyclic aromatic hydrocarbons pahs are sometimes referred to as polynuclear aromatic hydrocarbons pnas, condensed ring aromatics, or fused ring aromatics. Polycyclic aromatic are hydrocarbons that are composed of multiple aromatic rings. Jrcirmm catalogue pdf format or jrcirmm catalogue search engine. The group of pahs includes all compounds that are composed of two to seven rings of carbon and hydro.
Polycyclic aromatic hydrocarbon structure index nist page. A wide range of aromatic compounds has benzene rings located in ortho positions. The simplest such chemicals are naphthalene, having two aromatic rings, and the threering compounds anthracene and phenanthrene. Effect of polycyclic aromatic compounds and phorbol esters. Calibrate each personal sampling pump with a representative sampler in line. Pahs are released from burning coal, oil, gasoline, trash, tobacco, and wood.
Synthesis of aromatic nheterocycles and polycyclic heteroaromatic compounds. Polycyclic arenes and heteroarenes synthesis properties. Mar 15, 2015 the chemical group of polycyclic aromatic compounds pac, including the betterknown subgroup of polycyclic aromatic hydrocarbons pah and the heterocyclic aromatic compounds nsopac, heterocycles, comprise several thousand individual compounds. Where possible, cas numbers aresupplied tofacilitateliterature searches. The intent was to provide a general overview of the relevant ecotoxicological studies for these ubiquitous compounds and to provide basic information on environmental chemistry, sources, basic ecotoxicological methods, and important controlling factors. The environmental protection agency epa has identified 1,408 hazardous waste sites as the most serious in the nation. Other authors consider pahs to start with the tricyclic species phenanthrene and anthracene. Introduction polycyclic aromatic hydrocarbons pahs are a large family of organic compounds that are typically composed of two or more fused aromatic rings. The use of aromatic hydrocarbons is common in both biological and synthetic processes. Most frequently, nonbranded products at affordable prices get negative attention in this respect, but products from renowned companies may contain pahs as well.
The pacs in air during april to may 2014 were elevated near mining activities and. Polycyclic aromatic hydrocarbons pahs epa archives. The primary purpose of this study was to characterize the polycyclic aromatic hydrocarbon concentrations found in soils across new jersey where the population density was 2,000 people per square mile or greater and in areas not known to be directly impacted by a discharge or historic fill. To learn about our use of cookies and how you can manage your cookie settings, please see our cookie policy. This edition supersedes any previously released draft or final profile. The air monitoring of polycyclic aromatic compounds pacs and pac transformation. Mixed contributions from biomass, coal, and petroleum combustion were responsible for the particulate polycyclic aromatic hydrocarbon pollution. You may need a pdf reader to view some of the files on this page. Mapping indicators of toxicity for polycyclic aromatic compounds in the atmosphere of the athabasca oil sands region narumol jariyasopit, tom harner, dongmei wu, andrew williams, sabina halappanavar, and ky su. Examples of pah compounds with attached alkyl groups and aromatic compounds with nitrogen, sulfur, or oxygen,s except for the alkyl groups, hydrogen atoms bonded to carbon atoms are omittedoleum and individual polycyclic aromatic hydrocarbons most pars are formed by a process of thermal decomposition pyrolysis and subsequent.
Uncommon sorption mechanism of aromatic compounds onto. Some pahs are irritants while others are carcinogenic. The work of the following coordinators was crucial in the development of this. Sabljid prediction of distribution properties of substituted mono and polycyclic aromatic compounds 277 ha. Luijk predictive study of the intercalation geometry and dynamics of dnanaphthodifuran complexes 285 p. In general, the term polycyclic includes polycyclic aromatic compounds, including polycyclic aromatic hydrocarbons, as well as heterocyclic aromatic compounds with multiple rings where heteroaromatic compounds are aromatic compounds that contain sulfur, nitrogen, oxygen, or another noncarbon atoms in their rings in addition to carbon. The murine ah locus regulates the induction of the numerous xenobioticmetabolizing enzyme activities in the liver by polycyclic aromatic compounds, such as mc or tcdd 38. Polycyclic aromatic compounds in press paper iii nkansah, m. Polycyclic aromatic hydrocarbons pahs european commission.
Pahs and to emphasize the human health effects that may result. You can recognize the aromatic compounds in this text by the presence of one or more benzene rings in their structure. It is one in a series of public health statements about hazardous substances and their health effects. Hightemperature cooking, such as grilling, will form pahs in meat and other foods. Polycyclic aromatic hydrocarbons pahs are a class of hazardous organic compounds consisting of three or more fused benzene rings in linear, angular, and cluster arrangements. Neat compounds should be weighed out in a glove box. Polycyclic aromatic compounds category guidance document pdf 71 kb, august 2001 strychnine and salts. Pdf polycyclic arenes and heteroarenes synthesis properties and applications uploaded by lewis carroll, each chapter is dedicated to a specific compound class the first eight covering polycyclic arenes including both planar and non planar conjugated molecules while chapters nine to twelve deal with polycylic heteroarenes. Exposure to polycyclic aromatic hydrocarbons usually occurs by breathing air contaminated by wild fires or coal tar, or by eating foods that have. Pahs generated from these sources can bind to or form small particles in the air. Whether in mouse pads, toys, or bathing shoes polycyclic aromatic hydrocarbons pahs are ubiquitous.
By closing this message, you are consenting to our use of cookies. Sources and characteristics of polycyclic aromatic hydrocarbons in. List of toxic chemicals within the polychlorinated alkanes category and guidance for reporting pdf 36 kb, june 1999 polycyclic aromatic compounds. Pahs are found naturally in the environment but they can also be manmade. Aromatic hydrocarbon an overview sciencedirect topics.
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