5385-37-5

Usage

Chemical Class

Polycyclic Aromatic Hydrocarbon (PAH)

Structure

Six fused rings

Physical State

Colorless to light yellow liquid

Odor

Characteristic odor

Uses

Production of dyes, pigments, and plastics

Hazardous Properties

Carcinogenic, mutagenic, respiratory irritant, and skin sensitizer

Regulatory Status

Classified as a hazardous air pollutant and a priority pollutant by the Environmental Protection Agency (EPA)

Exposure

Not widely used in consumer products, mainly handled and manufactured in industrial settings with strict safety measures in place to minimize exposure and environmental release.

InChI:InChI=1/C16H16/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1,3-4,7,9,14H,2,5-6,8,10H2

Upstream product

• 129-00-0 pyrene 
• 6628-98-4 4,5-dihydropyrene 
• 64-17-5 ethanol 
• 123-51-3 i-Amyl alcohol 
• 51744-98-0 [2.2]Metacyclophan 

Downstream Products

• 1732-13-4 1,2,3,6,7,8-hexahydropyrene 
• 129-00-0 pyrene 
• 2435-85-0 perhydropyrene 
• 55775-16-1 1,2,3,3a,4,5,9,10-octahydropyrene 
• 55821-21-1 1,2,3,3a,4,5,9,10,10a,10b-decahydropyrene 
• 93313-08-7 Octahydropyren 

Relevant academic research and scientific papers

Quenched skeletal Ni as the effective catalyst for selective partial hydrogenation of polycyclic aromatic hydrocarbons

Quenched skeletal Ni is an active and selective catalyst for selective partial hydrogenation of polycyclic aromatic hydrocarbons (PAHs). The molecular structure of PAHs significantly dominate the hydrogenation process and furthermore, the distribution of hydrogenated products.

Facile sonochemical synthesis of carbon nanotube-supported bimetallic Pt-Rh nanoparticles for room temperature hydrogenation of arenes

Bimetallic Pt-Rh nanoparticles can be deposited uniformly on surfaces of carboxylate functionalized multi-walled carbon nanotubes (MWNTs) using a simple one-step sonochemical method. The bimetallic nanoparticle catalyst exhibits a strong synergistic effect relative to the individual Pt or Rh metal nanoparticles for catalytic hydrogenation of polycyclic aromatic hydrocarbons (PAHs), neat benzene and alkylbenzenes. Complete ring saturation of PAHs can be achieved using the bimetallic Pt-Rh/MWNTs catalyst at room temperature. This one-step synthesis technique provides a simple and rapid way of making highly active and recyclable CNT-supported monometallic and bimetallic nanocatalysts for low temperature hydrogenation reactions.

Hydrogenation of pyrene using Pd catalysts supported on tungstated metal oxides

A series of Pd catalyst supported on tungstated metal oxides (Pd/W-MOx) were prepared and applied for pyrene hydrogenation, and the role of acid sites of supports was investigated. Among Pd/W-MOx catalysts, Pd/W-TiO2 showed the highest activity which was comparable to those of Pd/BEA, Pd/Y and Pd/SiO2-Al2O3. As for the Pd catalysts supported on metal oxides without tungstate (Pd/MOx), the hydrogenation activity became higher with the increase in the acid amount of supports measured by calorimetric measurement of ammonia adsorption. The important role of acid sites on hydrogenation activity was demonstrated. On the other hand, the hydrogenation activity of Pd/W-MOx catalysts was not correlated to the acid amount of supports measured by ammonia adsorption. On-site generation of protonic acid on tungstated metal oxide supports was estimated from kinetic analysis of reduced W species in the presence of hydrogen by in situ UV-visible measurement. From a good correlation between the kinetic parameters of on-site protonic acid formation and the hydrogenation activity, the important role of protonic acid formation on tungstated metal oxide supports was clarified.

Good sulfur tolerance of a mesoporous Beta zeolite-supported palladium catalyst in the deep hydrogenation of aromatics

The activities of a Pd catalyst supported on mesoporous Beta zeolite (Beta-H) were evaluated for the hydrogenation of naphthalene and pyrene in the absence and presence of 200-ppm sulfur and for the hydrodesulfurization (HDS) of 4,6-dimethyldibenzothiophene (4,6-DMDBT). Compared with Pd/Al-MCM-41, the Pd/Beta-H catalyst exhibited better sulfur tolerance for hydrogenation of naphthalene and pyrene and higher activity for HDS of 4,6-DMDBT. The ratio of the hydrogenation of the second ring naphthalene in the absence and presence of 200-ppm sulfur for Pd/Beta-H was larger than that for Pd/Al-MCM-41 (0.47 vs 0.19). The desulfurization effect of Pd/Beta-H was greater than that of Pd/Al-MCM-41 (51 vs 35%). The difference in sulfur tolerance and HDS ability of the 2 catalysts is attributed to the difference in support acidity. Beta-H exhibited more acidic sites and a higher percentage of strong acidic sites than Al-MCM-41 (552 μmol/g and 43% vs 291 μmol/g and 18%).

Partial Hydrogenation of Polycyclic Aromatic Hydrocarbons by Electroreduction in Protic Solvents

Polycyclic aromatic hydrocarbons (PAH) such as anthracene (1), phenanthrene (5), acenaphthylene (15), pyrene (17), chrysene (22), and fluoranthene (28) are selectively hydrogenated upon electroreduction at a lead cathode in ethanolic solution. The degree of hydrogenation and the structure of the products depend on the reaction conditions, in particular on the applied reduction potential.

Relative Reactivities of Some Polycyclic Aromatic Hydrocarbons in Catalytic Hydrogenation over Raney Nickel

Catalytic hydrogenation of 9H-fluorene (10), phenanthrene (2), 4H-cyclopentaphenanthrene (3), pyrene (4), and fluoranthene (5) was carried out over Raney nickel (W-7) at 323 K under 608 kPa of hydrogen.The order of the reaction rate was 5>4>3>2>1.The adsorption equilibrium constant of the substrates decreased in the order 4 > or = 5 >> 2 > 3 >> 1.

Hydrogenation of Aromatic Hydrocarbons by Al/Ti Reagents

Treatment of anthracene (A) with LiAlH4 (LAH) at 150 deg C under atmospheric pressure gives 9,10-di- and 1,2,3,4-tetrahydroanthracene (2H-A and 4H-A).At 160-200 deg C and under hydrogen pressure (10-90 bar) a number of simple and polycyclic aromatic compounds are converted to fully or partially hydrogenated arenes.Addition of small amounts of TiCl4 or TiCl3 and the choice of solvents (heptane or glymes) have marked effects on the reaction.The pair triethylaluminium/TiCl4 acts also as efficient hydrogenation catalyst.

A Highly Selective Transannular Route to trans-trans-1,2,3,3a,4,5,9,10,10a,10b-Decahydropyrenes from Metacyclophanes

The treatment of metacyclophanes with aluminum chloride gave a variety of hydropyrenes as the results of dehydrogenation, cycloisomerization, and disproportionation reactions.With ethylaluminum dichloride, however, a highly selective reaction occured to give trans-trans-1,2,3,3a,4,5,9,10,10a,10b-decahydropyrene.Revised structures were presented for cis-cis- and trans-trans-decahydropyrenes based on 13C NMR and X-ray crystallographic analyses.

Hydrogenation of Pyrene and Catalytic Interconversion of Hydropyrenes

Reexamination on the hydrogenation of pyrene (1) with Raney nickel catalyst under atmospheric pressure afforded a mixture of 4,5-di- (2), 4,5,9,10-tetra- (3), 1,2,3,6,7,8-hexa- (4), and 1,2,3,3a,4,5-hexahydropyrene (5).The relative amount of each product at the initial reaction stage was determined by time-yield relation of the products.The formation sequence of the products is discussed with reference to the hydrogenations of 2-5: 4 may be formed independent of 2, and 2 is converted to 3.Hydropyrene 5 may be produced from 1 mainly through the same ?-adsorbed species which also leads to 2.The hydrogenation of 1 with palladium and platinum catalysts gave similar results as with nickel.With nickel and palladium catalysts the hydrogenation of 1 was faster than that of 4H-cyclopentaphenanthrene (9).However, with platinum the hydrogenation of 1 was slower than that of 9.Catalytic interconversion of 2-5 was examined at 240 deg C under an argon pressure of 90 kg cm-2.Hydroarene 2 was easily dehydrogenated, and 3 and 5 were interconverted to a fair extent.Therefore, 2,3, and 5 may be good hydrogen donor solvents for coal liquefaction.