Polyaromatic Hydrocarbon
Transcript of Polyaromatic Hydrocarbon
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POLYCYCLIC AROMATIC HYDROCARBON (PAH)
Polycyclic aromatic hydrocarbons (PAHs), also known as poly-aromatic
hydrocarbons or polynuclear aromatic hydrocarbon, are potent atmospheric
pollutants that consist of fused aromatic rings and do not contain heteroatoms or
carry substituents. Naphthalene is the simplest example of a PAH. PAHs occur
in oil, coal, and tar deposits, and are produced as byproducts of fuel burning
(whether fossil fuel or biomass). As a pollutant, they are of concern because some
compounds have been identified as carcinogenic, mutagenic, and teratogenic.
PAHs are also found in cooked foods. Studies have shown that high levels of
PAHs are found, for example, in meat cooked at high temperatures such as
grilling or barbecuing, and in smoked fish.
As for the kinds of polyaromatic hydrocarbons:
AcenaphtheneAcenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting
ofnaphthalene with anethylene bridge connecting positions 1 and 8. An
alternative name, 1,2 dihydroacenaphthylena, emphasizes that it is a hydrogenated
form ofacenaphthylene. It is a constituent ofcoal tar.Acenaphthene was prepared
the first time from coal tar by Marcellin Berthelot and after that with Bardy he
synthesized it from -ethyl naphthalene.It is used in preparation of dyes,
pesticides and pharmaceuticals.It does not appear to be carcinogenic.
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Struktur of Acenaphthene
AcenaphthyleneAcenaphthylene is a polycyclic aromatic hydrocarbon consisting
ofnaphthalene with an ethylene bridge connecting positions 1 and 8. It is a
constituent ofcoal tar. Reduction of the ethylene group gives the related
compound acenaphthene.Unlike most polycyclic aromatic hydrocarbons, it has
no fluorescence.
Struktur ofAcenaphthylene
AnthraceneAnthracene is a solid polycyclic aromatic hydrocarbon consisting of three
fused benzene rings. It is a component ofcoal-tar. Anthracene is used in
the production of the red dye alizarin and other dyes. Anthracene is colorless but
exhibits a blue (400-500 nm peak) fluorescence underultraviolet light.
Struktur ofAnthracene
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Benz[a]anthracene
benzo[a]pyreneBenzo[a]pyrene (C20H12) is a five-ring polycyclic aromatic
hydrocarbon whose metabolites aremutagenic and highly carcinogenic.
Benzo[a]pyrene is listed as a Group 1 carcinogen by theIARC. It belongs to a
class of polycyclic aromatic compounds known as benzopyrenes, which consist of
a benzene ring fused to a pyrene molecule. Benzo[a]pyrene is a product of
incompletecombustion at temperatures between 300 and 600C. Benzo[a]pyrene
was determined in 1933 to be the component ofcoal tar responsible for the first
recognized occupation-associated cancers, the sooty warts (cancers of
the scrotum) suffered by chimney sweeps in 18th century England. In the 19th
century, high incidences ofskin cancers were noted among fuel industry workers.
By the early 20th century, the toxicity of benzo[a]pyrene was demonstrated
whenmalignant skin tumors were produced in laboratory animals by repeatedly
painting them withcoal tar.
Struktur of Benzo[a]pyrene
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Benzo[e]pyreneBenzo[e]pyrene is a polycyclic aromatic hydrocarbon with the chemical
formula C20H12. It is listed as a Group 3 carcinogen by the IARC.
Structur ofbenzo[e]pyrene
Benzo[b]fluorantheneStructur ofbenzo[b]fluoranthene
Benzo[ghi]peryleneBenzo[ghi]perylene is a polycyclic aromatic hydrocarbon with the chemical
formula C22H12.
Stucture of Benzo[ghi]perylene
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Benzo[j]fluorantheneBenzo[j]fluoranthene is a polycyclic aromatic hydrocarbon with the chemical
formula C20H12.
Structure of Benzo[j]fluoranthene
Benzo[k]fluorantheneBenzo[k]fluoranthene is a polycyclic aromatic hydrocarbon with the chemical
formula C20H12.
Structure of Benzo[k]fluoranthene
ChryseneChrysene is a polycyclic aromatic hydrocarbon (PAH) with the molecular
formula C18H12 that consists of four fused benzene rings. It is a natural constituent
ofcoal tar, from which it was first isolated and characterized. It is also found
in creosote, a chemical used to preserve wood.
Chrysene is formed in small amounts during the burning or distillation of
coal, crude oil, and plant material.
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The name "chrysene" originates from Greeko(chrysos), meaning
"gold", and is due to the golden-yellow color of the crystals of the hydrocarbon,
thought to be the proper color of the compound at the time of its isolation and
characterization. However, high purity chrysene is colorless, the yellow hue being
due to the traces of its yellow-orange isomer tetracene, which cannot be separated
easily. Related compounds chrysene is Pyrene, Tetracene,Triphenylene
Structure of Chrysene
CoroneneCoronene (also known as superbenzene) is a polycyclic aromatic
hydrocarbon (PAH) comprising six peri-fused benzene rings.[1]
It is a yellow
material that dissolves in such solvents as benzene, toluene, and dichloromethane.
Its solutions emit blue light fluorescence under UV light. Its emission spectrum is
not symmetrical with its excitation spectrum and varies in the number of bands
and their relative intensities depending on the solvent. It has been used as a
solvent probe, similar to pyrene.
It occurs naturally as the mineral carpathite, which is characterized by flakes
of pure coronene embedded in sedimentary rock. This mineral may result from
ancient hydrothermal vent activity.
Coronene is produced in the petroleum refining process of hydrocracking, where
it can dimerize to a fifteen ring PAH, trivially named "dicoronylene" (formally
named benzo[10,11]phenanthro[2',3',4',5',6':4,5,6,7]chryseno[1,2,3-bc]coronene
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or benzo[1,2,3-bc:4,5,6-b'c']dicoronene). Coronene has been seen on the surface
ofTitan (Saturn's moon). It can cause DNA damage in mammals.
The compound is of theoretical interest to organic chemists because of
its aromaticity. It can be described by 20 resonance structures or by a set of three
mobile Clar sextets. In the Clar sextet case the most stable structure for coronene
has only the three isolated outer sextets as fully aromatic
although superaromaticity would still be possible when these sextets are able to
migrate into the next ring.
Structure of Coronene
Dibenz(a,h)anthraceneDibenz(a,h)anthracene is an organic compound with the chemical
formula C22H14.
Stucture ofDibenz(a,h)anthracene
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FluorantheneFluoranthene is a polycyclic aromatic hydrocarbon (PAH) consisting of
a naphthalene and abenzene unit connected by a five-membered ring. It is a
member of the class of PAHs known as non-alternant PAHs because it has rings
other than those with six carbon atoms. It is a structural isomer of the alternant
PAH pyrene. It is not as thermodynamically stable as pyrene because its electrons
cannot resonate throughout the complete structure as the corresponding ones in
pyrene.
Fluoranthene is found in many combustion products, along with other PAHs.
Its presence is an indicator of less efficient or lower-temperature combustion,
since non-alternant PAHs are less preferred in formation than alternant PAHs.
Fluoranthene is one of the U.S. Environmental Protection Agency's 16 priority
pollutant PAHs and is a carcinogen.
Fluoranthene has been isolated from coal tar pitch. Its name is derived from
its fluorescenceunder UV light.
Structure ofFluoranthene
FluoreneFluorene or 9H-fluorene, is a polycyclic aromatic hydrocarbon. It forms white
crystals that exhibit a characteristic, aromatic odor similar to that ofnaphthalene.
It is combustible. It has a violet fluorescence, hence its name. For commercial
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purposes it is obtained from coal tar. It is insoluble in water and soluble
in benzene and ether.
Fluorene is a precursor to other fluorene compounds; the parent species has
few applications. Fluorene-9-carboxylic acid is a precursor to pharmaceuticals. 2-
Aminofluorene, 3,6-bis-(dimethylaminofluorene), and 2,7-diiodofluorene are
precursors to dyes. Oxidation of fluorene gives fluorenone, which is nitrated to
give commercially useful derivatives. 9-Fluorenylmethyl chloroformate (Fmoc
chloride) is used to introduce the 9-fluorenylmethyl carbamate (Fmoc)protecting
group on amines in peptide synthesis.[2]
Polyfluorene polymers (where carbon 7 of one unit is linked to carbon 2 of
the next one, displacing two hydrogens) are electrically
conductive and electroluminescent, and have been much investigated for use as
a luminophore in organic light-emitting diodes.
Structure offluorene
indeno(1,2,3-cd)pyrene
PhenanthrenePhenanthrene is a polycyclic aromatic hydrocarbon composed of three
fused benzene rings. The name phenanthrene is a composite
ofphenyl and anthracene. In its pure form, it is found incigarette smoke and is a
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known irritant, photosensitizing skin to light. Phenanthrene appears as a white
powder having blue fluorescence.
Phenanthrene is nearly insoluble in water but is soluble in most organic
solvents such astoluene, carbon tetrachloride, ether, chloroform, acetic
acid and benzene.
The compound with a phenanthrene skeleton and nitrogens at the 4 and 5
positions is known asphenanthroline.
Structure ofphenanthrene
Pyrene
Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four
fused benzene rings, resulting in a flat aromatic system. This colourless solid is
the smallest peri-fused PAH (one where the rings are fused through more than one
face). Pyrene forms during incomplete combustion of organic compounds.
Related compound pyrene is benzopyrene.
Structure of pyrene
http://en.wikipedia.org/wiki/Irritationhttp://en.wikipedia.org/wiki/Photosensitivity_in_animalshttp://en.wikipedia.org/wiki/Toluenehttp://en.wikipedia.org/wiki/Carbon_tetrachloridehttp://en.wikipedia.org/wiki/Etherhttp://en.wikipedia.org/wiki/Chloroformhttp://en.wikipedia.org/wiki/Acetic_acidhttp://en.wikipedia.org/wiki/Acetic_acidhttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Phenanthrolinehttp://en.wikipedia.org/wiki/Phenanthrenehttp://en.wikipedia.org/wiki/Pyrenehttp://en.wikipedia.org/wiki/Polycyclic_aromatic_hydrocarbonhttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Aromaticityhttp://en.wikipedia.org/wiki/Combustion#Incompletehttp://en.wikipedia.org/wiki/Combustion#Incompletehttp://en.wikipedia.org/wiki/Aromaticityhttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Polycyclic_aromatic_hydrocarbonhttp://en.wikipedia.org/wiki/Pyrenehttp://en.wikipedia.org/wiki/Phenanthrenehttp://en.wikipedia.org/wiki/Phenanthrolinehttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Acetic_acidhttp://en.wikipedia.org/wiki/Acetic_acidhttp://en.wikipedia.org/wiki/Chloroformhttp://en.wikipedia.org/wiki/Etherhttp://en.wikipedia.org/wiki/Carbon_tetrachloridehttp://en.wikipedia.org/wiki/Toluenehttp://en.wikipedia.org/wiki/Photosensitivity_in_animalshttp://en.wikipedia.org/wiki/Irritation -
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Polycyclic Aromatic Hydrocarbon Analysis (PAH)
Polycyclic Aromatic Hydrocarbon (PAH) analysis is a quantitative
technique used for the determination of PAHs (parent compounds and
homologues) in extracts of sediment, water, and tissue. PAH analysis is performed
using gas chromatography / mass spectrometry (GC/MS) in selected ion
monitoring (SIM) mode. Method detection limits for PAHs using this method are
extremely.
The GC is temperature programmed, operated in splitless mode, and carrier
flow is by electronic pressure control. The capillary column is a J&W DB-
5MS
(60 m long by 0.25 mm ID and 0.25 mm film thickness) or equivalent. The
data acquisition system allows continuous acquisition and storage of all data
during analysis and is capable of displaying ion abundance versus time or scan
number.
A sample batch is analyzed as an analytical set including samples along
with the following specified quality control samples: method-blank, matrix-spike,
duplicate, matrix-spike duplicate, and standard reference material.
A calibration curve is established by analyzing each of five calibration
standards (analyte concentrations ranging from 0.02 to 1 mg/mL) and determining
a relative response factor (RRF) for each analyte. Calibration check standards are
interspersed throughout an analytical batch in order to insure the instruments
integrity. A diluted oil standard is used as a retention index solution for
compounds not found in the calibration solution. Analyte concentrations are
determined using the internal standard method and analyte concentrations are
corrected for surrogate recovery.
http://www.tdi-bi.com/analytical_services/mdls.htmlhttp://www.tdi-bi.com/analytical_services/mdls.html -
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Individual Task
Kapita selekta Analitik
The Types of Policyclic Aromatic Hydrocarbon
NAMA : MURNIYATI MUIS
NIM : H311 08 007
JURUSAN KIMIA
FAKULTAS MATEMATIKA DAN ILMU PENGETAHUAN ALAM
UNIVERSITAS HASANUDDIN
MAKASSAR
2011