Dicoronylene

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Dicoronylene
Dicoronylene structure.png
Dicoronylene 3D ball.png
Names
Preferred IUPAC name
Benzo[1,2,3-bc:4,5,6-bc′]dicoronene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C48H20/c1-5-23-9-13-27-17-31-33-19-29-15-11-25-7-3-22-4-8-26-12-16-30-20-34(46(33)48-43(29)39(25)36(22)40(26)44(30)48)32-18-28-14-10-24-6-2-21(1)35-37(23)41(27)47(45(31)32)42(28)38(24)35/h1-20H X mark.svgN
    Key: QOPWDVCEMZLGPK-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C48H20/c1-5-23-9-13-27-17-31-33-19-29-15-11-25-7-3-22-4-8-26-12-16-30-20-34(46(33)48-43(29)39(25)36(22)40(26)44(30)48)32-18-28-14-10-24-6-2-21(1)35-37(23)41(27)47(45(31)32)42(28)38(24)35/h1-20H
    Key: QOPWDVCEMZLGPK-UHFFFAOYAN
  • C1=CC2=C3C4=C1C=CC5=C4C6=C(C=C5)C=C7C8=CC9=C1C4=C(C=CC5=C4C4=C(C=C5)C=CC5=CC(=C8C1=C54)C1=C7C6=C3C(=C1)C=C2)C=C9
Properties
C48H20
Molar mass 596.688 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dicoronylene is the trivial name for a very large polycyclic aromatic hydrocarbon. Its formal name is benzo[10,11]phenanthro[2',3',4',5',6':4,5,6,7]chryseno[1,2,3-bc]coronene (IUPAC name) or benzo[1,2,3-bc:4,5,6-b'c']dicoronene (name sometimes used in Chemical Abstracts). It has 15 rings and is a brick-red solid. Its formula is C
48
H
20
. [1] Dicoronylene sublimes under high vacuum, 0.001 torr, between 250 °C and 300 °C.

Contents

Structure

Due to its large size and limited availability, the organic chemistry of dicoronylene is little known. Dicoronylene does undergo a Diels–Alder reaction with maleic anhydride on one or both of the central bay regions on either side of the bridging ring. The double bond of maleic anhydride forms two carbon–carbon bonds on the ends of the bay region, making a new six-membered ring. Heating removes the anhydride as carbon dioxide gas and gives the corresponding 16-ring and 17-ring PAHs.

Occurrence

Dicoronylene was first observed in the solid residue produced in coal gasification. This residue contained large amounts of coronene and ovalene. After these were extracted and identified, a reddish residue remained, which was sparingly soluble in organic solvents. Elemental analysis indicated that it was most likely the condensed dimer of coronene.

Dicoronylene was later discovered to occur as a by-product of the catalytic hydrocracking used in petroleum processing. It is formed when two coronene molecules fuse. It is estimated that catalytical hydrocracking produces several hundred metric tons of dicoronylene worldwide per year, making it the most prevalent large PAH. In this process, the analogous 18-ring PAH formed from coronene and ovalene (C
56
H
22
) is also formed in 1% to 20% proportions. It is purple in color.

Properties

The formation of dicoronylene in hydrocracking reactors is a serious problem because its low solubility make it precipitate in any cooler part of the reactor flow path. This causes plugging of flow lines that require periodic shutdown and removal of the reddish deposits. Dicoronylene is also a constituent of coke formed on hydrocracking catalysts, which reduces their activity.

Thermal pyrolysis of coronene shows masses of dicoronylene and the condensed trimer, tetramer, and pentamer in the mass spectrum of the black product. These larger coronene condensates are black in color.

Dicoronylene is moderately soluble in 1,2,4-trichlorobenzene and these solutions have a greenish yellow fluorescence. Unlike coronene, dicoronylene has symmetrical fluorescence excitation and emission spectra. It is virtually insoluble in most solvents.

Dicoronylene has been studied as a model for interstellar PAHs. Its large size and planarity have also shown promise as a chromatographic separation material.

Related Research Articles

Aromatic compounds are those chemical compounds that contain one or more rings with pi electrons delocalized all the way around them. In contrast to compounds that exhibit aromaticity, aliphatic compounds lack this delocalization. The term "aromatic" was assigned before the physical mechanism determining aromaticity was discovered, and referred simply to the fact that many such compounds have a sweet or pleasant odour; however, not all aromatic compounds have a sweet odour, and not all compounds with a sweet odour are aromatic. Aromatic hydrocarbons, or arenes, are aromatic organic compounds containing solely carbon and hydrogen atoms. The configuration of six carbon atoms in aromatic compounds is called a "benzene ring", after the simple aromatic compound benzene, or a phenyl group when part of a larger compound.

Pyrolysis Thermal decomposition of materials at elevated temperatures in an inert atmosphere

Pyrolysis is the thermal decomposition of materials at elevated temperatures in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements pyro "fire" and lysis "separating".

Cracking (chemistry)

In petrochemistry, petroleum geology and organic chemistry, cracking is the process whereby complex organic molecules such as kerogens or long-chain hydrocarbons are broken down into simpler molecules such as light hydrocarbons, by the breaking of carbon-carbon bonds in the precursors. The rate of cracking and the end products are strongly dependent on the temperature and presence of catalysts. Cracking is the breakdown of a large alkane into smaller, more useful alkenes. Simply put, hydrocarbon cracking is the process of breaking a long chain of hydrocarbons into short ones. This process requires high temperatures.

Phenanthrene Polycyclic aromatic hydrocarbon composed of three fused benzene rings

Phenanthrene is a likely carcinogenic compound that poses a large toxicity risk to exposed living organisms. However, according to IARC, it is not identified as probable, possible or confirmed human carcinogen. It is a polycyclic aromatic hydrocarbon (PAH)-which are a large group of organic compounds occurring in groups of two or more. Phenanthrene occurs naturally and also is a man-made chemical. Commonly, humans are exposed to phenanthrene through inhalation of cigarette smoke but there are many routes of exposure. Evidence, proven through animal studies, shows that phenanthrene is a potential carcinogen. It appears as a colorless, crystal-like solid but can also look yellow.

Coronene Chemical compound

Coronene is a polycyclic aromatic hydrocarbon (PAH) comprising seven peri-fused benzene rings. Its chemical formula is C
24
H
12
. It is a yellow material that dissolves in common solvents including benzene, toluene, and dichloromethane. Its solutions emit blue light fluorescence under UV light. It has been used as a solvent probe, similar to pyrene.

Polycyclic aromatic hydrocarbon Hydrocarbon composed of multiple aromatic rings

A polycyclic aromatic hydrocarbon (PAH) is a hydrocarbon—a chemical compound containing only carbon and hydrogen—that is composed of multiple aromatic rings. The group is a major subset of the aromatic hydrocarbons. The simplest of such chemicals are naphthalene, having two aromatic rings, and the three-ring compounds anthracene and phenanthrene. The terms polyaromatic hydrocarbon or polynuclear aromatic hydrocarbon are also used for this concept.

Pyrene Chemical compound

Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is C
16
H
10
. This yellow solid is the smallest peri-fused PAH. Pyrene forms during incomplete combustion of organic compounds.

Triphenylene Chemical compound

In chemistry, the organic compound triphenylene is a flat polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings. Triphenylene can be isolated from coal tar. It is also made synthetically by synthesis and trimerization of benzyne. One molecule of triphenylene has delocalized 18-π-electron systems based on a planar structure. It has the molecular formula C
18
H
12
.

Perylene Chemical compound

Perylene or perilene is a polycyclic aromatic hydrocarbon with the chemical formula C20H12, occurring as a brown solid. It or its derivatives may be carcinogenic, and it is considered to be a hazardous pollutant. In cell membrane cytochemistry, perylene is used as a fluorescent lipid probe. It is the parent compound of a class of rylene dyes.

Fluorene Chemical compound

Fluorene, or 9H-fluorene is an organic compound with the formula (C6H4)2CH2. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene. It has a violet fluorescence, hence its name. For commercial purposes it is obtained from coal tar. It is insoluble in water and soluble in many organic solvents. Although sometimes classified as a polycyclic aromatic hydrocarbon, the five-membered ring has no aromatic properties. Fluorene is mildly acidic.

Idrialite

Idrialite is a rare hydrocarbon mineral with approximate chemical formula C22H14.

Fluoranthene Chemical compound

Fluoranthene is a polycyclic aromatic hydrocarbon (PAH). The molecule can be viewed as the fusion of naphthalene and benzene unit connected by a five-membered ring. Although samples are often pale yellow, the compound is colorless. It is soluble in nonpolar organic solvents. 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. Its name is derived from its fluorescence under UV light.

Ovalene Chemical compound

Ovalene is a polycyclic aromatic hydrocarbon with the formula C32H14, which consists of ten peri-fused six-membered rings. It is very similar to coronene.

Chrysene Chemical compound

Chrysene is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula C
18
H
12
that consists of four fused benzene rings. It is a natural constituent of coal tar, from which it was first isolated and characterized. It is also found in creosote at levels of 0.5-6 mg/kg.

Tetraphenylcyclopentadienone Chemical compound

Tetraphenylcyclopentadienone is an organic compound with the formula (C6H5)4C4CO. It is a dark purple to black crystalline solid that is soluble in organic solvents. It is an easily made building block for many organic and organometallic compounds.

Benzopyrene

A benzopyrene is an organic compound with the formula C20H12. Structurally speaking, the colorless isomers of benzopyrene are pentacyclic hydrocarbons and are fusion products of pyrene and a phenylene group. Two isomeric species of benzopyrene are benzo[a]pyrene and the less common benzo[e]pyrene. They belong to the chemical class of polycyclic aromatic hydrocarbons.

Benzo(<i>c</i>)phenanthrene Chemical compound

Benzo[c]phenanthrene is a polycyclic aromatic hydrocarbon with the chemical formula C18H12. It is a white solid that is soluble in nonpolar organic solvents. It is a nonplanar molecule consisting of the fusion of four fused benzene rings. The compound is of mainly theoretical interest but it is environmentally occurring and weakly carcinogenic.

Benzo(<i>j</i>)fluoranthene Chemical compound

Benzo[j]fluoranthene (BjF) is an organic compound with the chemical formula C20H12. Classified as a polycyclic aromatic hydrocarbon (PAH), it is a colourless solid that is poorly soluble in most solvents. Impure samples can appear off white. Closely related isomeric compounds include benzo[a]fluoranthene (BaF), bendo[b]fluoranthene (BbF), benzo[e]fluoranthene (BeF), and benzo[k]fluoranthene (BkF). BjF is present in fossil fuels and is released during incomplete combustion of organic matter. It has been traced in the smoke of cigarettes, exhaust from gasoline engines, emissions from the combustion of various types of coal and emissions from oil heating, as well as an impurity in some oils such as soybean oil.

Benzo(<i>k</i>)fluoranthene Chemical compound

Benzo[k]fluoranthene is an organic compound with the chemical formula C20H12. Classified as a polycyclic aromatic hydrocarbon (PAH), it is a colourless solid that is poorly soluble in most solvents. Impure samples can appear off white. Closely related isomeric compounds include benzo(a)fluoranthene, benzo(b)fluoranthene, benzo(e)fluoranthene, and benzo(j)fluoranthene.

Benzo(<i>c</i>)fluorene Chemical compound

Benzo[c]fluorene is a polycyclic aromatic hydrocarbon (PAH) with mutagenic activity. It is a component of coal tar, cigarette smoke and smog and thought to be a major contributor to its carcinogenic properties. The mutagenicity of benzo[c]fluorene is mainly attributed to formation of metabolites that are reactive and capable of forming DNA adducts. According to the KEGG it is a group 3 carcinogen. Other names for benzo[c]fluorene are 7H-benzo[c]fluorene, 3,4-benzofluorene, and NSC 89264.

References

  1. Fetzer, J. C. (2000). The Chemistry and Analysis of the Large Polycyclic Aromatic Hydrocarbons. New York: Wiley.