Names | |
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Preferred IUPAC name 1,2-Dihydroacenaphthylene | |
Other names 1,8-Ethylenenaphthalene peri-Ethylenenaphthalene Naphthyleneethylene Tricyclo[6.3.1.04,12]dodecapentaene Tricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaene | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.336 |
EC Number |
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KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
UN number | 3077 |
CompTox Dashboard (EPA) | |
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Properties | |
C12H10 | |
Molar mass | 154.212 g·mol−1 |
Appearance | White or pale yellow crystalline powder |
Density | 1.024 g/cm3 |
Melting point | 93.4 °C (200.1 °F; 366.5 K) |
Boiling point | 279 °C (534 °F; 552 K) |
0.4 mg/100 ml | |
Solubility in ethanol | slight |
Solubility in chloroform | slight |
Solubility in benzene | very soluble |
Solubility in acetic acid | soluble |
Vapor pressure | 0.001 to 0.01 mmHg at 68°F ; 5 mmHg at 238.6°F [1] |
-.709·10−6 cm3/g | |
Thermochemistry [2] | |
Heat capacity (C) | 190.4 J mol−1 K−1 |
Std molar entropy (S⦵298) | 188.9 J mol−1 K−1 |
Std enthalpy of formation (ΔfH⦵298) | 70.3 kJ/mol |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 135 °C (275 °F; 408 K) |
>450 °C (842 °F; 723 K) | |
Safety data sheet (SDS) | ICSC 1674 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound. [3]
Acenaphthene was prepared the first time from coal tar by Marcellin Berthelot. [4] Later Berthelot and Bardy synthesized the compound by cyclization of α-ethylnaphthalene. Industrially, it is still obtained from coal tar together with its derivative acenaphthylene (and many other compounds).
Like other arenes, acenaphthene forms complexes with low valent metal centers. One example is (η6-acenaphthene)Mn(CO)3]+. [5]
It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners. [3] Naphthalene dicarboxylic anhydride is the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes. [6] [7]
Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula (CH2)8(CO2H)2. It is a white flake or powdered solid. Sebaceus is Latin for tallow candle, sebum is Latin for tallow, and refers to its use in the manufacture of candles. Sebacic acid is a derivative of castor oil.
Acenaphthylene, a polycyclic aromatic hydrocarbon is an ortho- and peri-fused tricyclic hydrocarbon. The molecule resembles naphthalene with positions 1 and 8 connected by a -CH=CH- unit. It is a yellow solid. Unlike many polycyclic aromatic hydrocarbons, it has no fluorescence.
Acenaphthoquinone is a quinone derived from acenaphthene. It is a water-insoluble yellow solid. It is a precursor to some agrichemicals and dyes.
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.
1,2,4-Trimethylbenzene, also known as pseudocumene, is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid with a strong odor. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum (about 3%). It is one of the three isomers of trimethylbenzene.
1-Octadecene is a long-chain hydrocarbon and an alkene with the molecular formula CH2=CH(CH2)15CH3. It is one of many isomers of octadecene. Classified as an alpha-olefin, 1-octadecene is the longest alkene that is liquid at room temperature.
Durene, or 1,2,4,5-tetramethylbenzene, is an organic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as an alkylbenzene. It is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and isodurene (1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.
Indane or indan is an organic compound with the formula C6H4(CH2)3. It is a colorless liquid hydrocarbon. It is a petrochemical, a bicyclic compound. It occurs at the level of about 0.1% in coal tar. It is usually produced by hydrogenation of indene.
1,2,3-Trimethylbenzene is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum. It is one of the three isomers of trimethylbenzene. It is used in jet fuel, mixed with other hydrocarbons, to prevent the formation of solid particles which might damage the engine.
Prehnitene or 1,2,3,4-tetramethylbenzene is an organic compound with the formula C6H2(CH3)4, classified as an aromatic hydrocarbon. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar. Prehnitene is one of three isomers of tetramethylbenzene, the other two being isodurene (1,2,3,5-tetramethylbenzene) and durene (1,2,4,5-tetramethylbenzene). It is a relatively easily oxidized benzene derivative, with E1/2 of 2.0 V vs NHE.
Isodurene or 1,2,3,5-tetramethylbenzene is an organic compound with the formula C6H2(CH3)4, classified as an aromatic hydrocarbon. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar. Isodurene is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and durene (1,2,4,5-tetramethylbenzene).
1-Dodecene is an alkene with the formula C10H21CH=CH2, consisting of a chain of twelve carbon atoms ending with a double bond. While there are many isomers of dodecene depending on which carbon the double bond is placed, this isomer is of greater commercial importance. It is classified as an alpha-olefin. Alpha-olefins are distinguished by having a double bond at the primary or alpha (α) position. This location of a double bond enhances the reactivity of the compound and makes it useful for a number of applications, especially for the production of detergents.
Phenanthrenedione is a quinone derivative of a polycyclic aromatic hydrocarbon. It is an orange, water-insoluble solid.
Diethylbenzene (DEB) refers to any of three isomers with the formula C6H4(C2H5)2. Each consists of a benzene ring and two ethyl substituents. The meta and para have the greater commercial significance. All are colorless liquids.
4-Ethyltoluene is an organic compound with the formula CH3C6H4C2H5. It is one of three isomers of ethyltoluene, the other two isomers being 3-ethyltoluene and 2-ethyltoluene. All are colorless liquids and all are used for the production of specialty polystyrenes.
1-Hexadecene, also known as 1-cetene, is a long-chain hydrocarbon and an alkene with the molecular formula CH2=CH(CH2)13CH3. It is one of many isomers of hexadecene. Classified as an alpha-olefin, 1-hexadecene is a colorless liquid.
o-Cymene is an organic compound classified as an aromatic hydrocarbon. Its structure consists of a benzene ring ortho-substituted with a methyl group and an isopropyl group. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents.
m-Cymene is an organic compound classified as an aromatic hydrocarbon. Its structure consists of a benzene ring meta-substituted with a methyl group and an isopropyl group. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents.
tert-Butylbenzene is an organic compound classified as an aromatic hydrocarbon. Its structure consists of a benzene ring substituted with a tert-butyl group. It is a flammable colorless liquid which is nearly insoluble in water but miscible with organic solvents.
1,8-Naphthalic anhydride is an organic compound with the formula C10H6(C2O3). It is one of three isomers of naphthalic anhydride, the other two being the 1,2- and the 2,3-derivatives. The 1,8-isomer is prepared by aerobic oxidation of acenaphthene. 2,6-naphthalenedicarboxylic acid can be prepared from this anhydride. 1,8-Naphthalic anhydride is a precursor to the 4-chloro and 4,5-dichloro derivatives. These chloride groups are susceptible to displacement by amines and alkoxides, giving rise, ultimately, to a large family of naphthalimides, which are used as optical brighteners.
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