208-96-8

Usage

Uses

Used in Chemical Synthesis:
Acenaphthalene is used as a precursor for the synthesis of various organic compounds, contributing to the production of a wide range of chemical products.
Used in Dye Production:
Acenaphthalene is utilized in the production of dyes, playing a crucial role in the creation of colorants for various applications.
Used in Pesticide Production:
In the agricultural industry, acenaphthalene is employed in the manufacturing of pesticides, helping to control pests and protect crops.
Used in Pharmaceutical Production:
Acenaphthalene is used in the development and production of pharmaceuticals, contributing to the creation of medications for various health conditions.
However, due to its carcinogenic and toxic properties, acenaphthalene's use is a subject of environmental and health concern, necessitating careful handling and regulation in industrial applications.

InChI:InChI=1/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H

Synthetic route

1-bromo-1H,3H-naphtho<1,8-cd>thiopyran 2,2-dioxide (51392-61-1) → acenaphthylene (208-96-8)

Conditions	Yield
With sodium methylate In methanol for 16.5h; Ambient temperature;	97%
With sodium methylate In methanol for 16.5h; Product distribution; Ambient temperature; var. of base;	97%

acenaphthene (83-32-9) + 7,7',8,8'-tetracyanoquinodimethane (1518-16-7) → 9-Acenaphthyl<4-(dicyanomethyl)phenyl>dicyanomethane (77074-97-6) + acenaphthylene (208-96-8)

Conditions	Yield
for 0.0833333h; Heating;	A 95.5% B n/a

Carbonic acid acenaphthen-1-yl ester methyl ester (164665-41-2) → acenaphthylene (208-96-8)

Conditions	Yield
With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 60℃; for 48h;	95%

Propynoic acid acenaphthen-1-yl ester (182313-38-8) → acenaphthylene (208-96-8)

Conditions	Yield
at 760℃; under 0.03 Torr;	95%
Multi-step reaction with 2 steps 1: 32 percent / deuterium oxide, triethylamine / tetrahydrofuran / 1.25 h / 35 °C 2: 95 percent / 760 °C / 0.03 Torr View Scheme

1,2-dihydroacenaphthylen-1-yl (3-(2)H)propyonate → acenaphthylene (208-96-8)

Conditions	Yield
at 760℃; under 0.03 Torr;	95%

trans-1,2-dibromo-1,2-dihydroacenaphthylene (25226-58-8) → acenaphthylene (208-96-8)

Conditions	Yield
With acetic acid; zinc	94%
With ethanol; zinc

1,2-dibromoacenaphthene (14209-08-6) → acenaphthylene (208-96-8)

Conditions	Yield
With sodium sulfide; Aliquat 336 In water; benzene for 1h; Ambient temperature;	92%

1-acenaphthenol (6306-07-6) → acenaphthylene (208-96-8)

Conditions	Yield
methyltrioxorhenium(VII) In benzene for 72h;	89%
zirconium(IV) chloride In acetonitrile at 20℃; for 0.666667h;	89%
With pyridine; thionyl chloride

C27H20N2O2 → (E)-1,2-diphenyl-ethene (103-30-0) + acenaphthylene (208-96-8)

Conditions	Yield
at 500℃; under 0.02 Torr; for 0.0833333h;	A 88% B 4%

2-[2-(1-chloro-vinyl)-phenyl]-thiophene → naphtho[1,2-b]thiophene (234-41-3) + acenaphthylene (208-96-8)

Conditions	Yield
at 800℃; under 0.1 Torr; Cyclization; Pyrolysis;	A 81% B 2%

acenaphthene (83-32-9) → acenaphthylene (208-96-8)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 24h; Reflux;	80%
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 120℃; under 9750.98 Torr; for 8h;	77%
With manganese(IV) oxide In benzene for 30h; Heating;	41%

1-acenaphthenol (6306-07-6) → acenaphthene-1-thiol + acenaphthylene (208-96-8)

Conditions	Yield
With Lawessons reagent In toluene for 0.5h; Heating;	A 72% B 13%
With Lawessons reagent In toluene for 0.5h; Heating;	A 72% B 13%

acenaphthene (83-32-9) + chloranil (118-75-2) → 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6) + acenaphthylene (208-96-8)

Conditions	Yield
In benzene for 18h; Irradiation;	A 68% B 19%

(acenaphthylene)chromium tricarbonyl (99414-44-5) + ethyl α-lithioisobutyrate → C36H34O4 + C18H18O2 (106017-42-9) + acenaphthylene (208-96-8)

Conditions

Yield

With N,N,N,N,-tetramethylethylenediamine; iodine In tetrahydrofuran Kinetics; to a soln. of nucleophile in THF was added soln. of complex in THF at -60°C; after 45 min at -60°C I2 in THF was added and soln. allowed to stir overnight while being warmed to room temp.;; soln. was filtered through Celite, evapd., extd. with ether, extract was washed with other solvents, then chromd. on silica column, eluent CHCl3-hexane;;

A 19% B 20% C 68%

C27H37BSi2 → acenaphthylene (208-96-8)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 24h; Schlenk technique; Inert atmosphere; Reflux;	57%

(acenaphthylene)chromium tricarbonyl (99414-44-5) + ethyl α-lithioisobutyrate → C18H18O2 (106017-42-9) + acenaphthylene (208-96-8)

Conditions

Yield

With N,N,N,N,-tetramethylethylenediamine; iodine; trifluoroacetic acid In tetrahydrofuran to a soln. of nucleophile in THF at -60°C soln. of complex was added, after 45 min at -60°C CF3COOH was added followed by I2, and soln. was allowed to stir overnight while being warmed to room temp.;; soln. was filtered through Celite, evapd.; residue was extd. was ether and washed with other solvents; then chromd. on silica column, eluent CH2Cl2-hexane;;

A 47% B 8%

C27H20N2O2 → (E)-1,2-diphenyl-ethene (103-30-0) + acenaphthene (83-32-9) + acenaphthylene (208-96-8)

Conditions	Yield
at 780℃; under 1 Torr; for 0.0833333h;	A 43% B 19% C 37%

dichloromethane (75-09-2) + (naphthalene-1,8-diyl)dilithium (61767-59-7) → naphthalene (91-20-3) + 1,1'-cis-ethene-1,2-diyl-bis-naphthalene (1233-36-9, 3960-21-2, 72597-92-3, 72597-93-4, 85248-67-5, 2633-10-5) + (E)-1,2-bis(1-naphthyl)ethene (1233-36-9) + 1H-Cyclobutanaphthalene (24973-91-9) + 1-Chloromethylnaphthalene (86-52-2) + acenaphthylene (208-96-8)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In diethyl ether at -100 - -60℃; Product distribution; Mechanism; var. of temp., further with CD2Cl2;	A 42% B n/a C n/a D 21% E n/a F n/a

dichloromethane (75-09-2) + (naphthalene-1,8-diyl)dilithium (61767-59-7) → naphthalene (91-20-3) + 1,1'-cis-ethene-1,2-diyl-bis-naphthalene (1233-36-9, 3960-21-2, 72597-92-3, 72597-93-4, 85248-67-5, 2633-10-5) + 1H-Cyclobutanaphthalene (24973-91-9) + acenaphthylene (208-96-8)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In diethyl ether at -100 - -60℃; Further byproducts given;	A 42% B n/a C 21% D n/a

(acenaphthylene)chromium tricarbonyl (99414-44-5) + lithium N,N-diethylisobutyramide → C40H44N2O2 (106017-45-2) + C20H23NO (106017-44-1) + acenaphthylene (208-96-8)

Conditions

Yield

With N,N,N,N,-tetramethylethylenediamine; iodine In tetrahydrofuran to a soln. of nucleophile in THF at -60°C soln. of complex was added, after 45 min at -60°C soln. of I2 in THF was added, and soln. was allowed to stir overnight while being warmed to room temp.;; soln. was filtered through Celite, evapd.; residue was extd. was ether and washed with other solvents; then chromd. on silica column, eluent CH2Cl2-hexane;;

A 16% B 42% C 41%

2-(2-ethynyl-phenyl)-thiophene (221230-46-2) → naphtho[1,2-b]thiophene (234-41-3) + acenaphthylene (208-96-8)

Conditions	Yield
at 1000℃; under 0.1 Torr; Cyclization; rearrangement; Pyrolysis;	A 18% B 41%

acenaphthene quinone (82-86-0) → 1-acenaphthenol (6306-07-6) + acenaphthene (83-32-9) + acenaphthylene (208-96-8)

Conditions	Yield
With samarium diiodide; water In tetrahydrofuran at 20℃; for 0.00277778h;	A 41% B 26% C 23%

C20H15N2O4S(1-)*Li(1+) → acenaphthene (83-32-9) + 9-Hydroxymethyl-1H-naphtho[1,2-c]furan-3-one (182313-44-6) + acenaphthylene (208-96-8)

Conditions	Yield
at 730℃; under 0.03 Torr; for 0.05h;	A 9% B 38% C 12%

1,3-dibromo-1H,3H-naphtho<1,8-cd>thiopyran 2,2-dioxide (83831-93-0, 83831-94-1) → decacyclene (191-48-0) + 1-bromoacenaphthylene (54736-49-1) + acenaphthylene (208-96-8)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 27℃; for 18h; Product distribution; other reagents;	A 5% B 33% C 23%
With potassium tert-butylate In tert-butyl alcohol for 1.5h; Heating;	A 5% B n/a C n/a

acenaphthene quinone (82-86-0) → decacyclene (191-48-0) + 1-acenaphthenol (6306-07-6) + acenaphthene (83-32-9) + acenaphthylene (208-96-8)

Conditions	Yield
bis(η6-biphenyl)titanium(0) In toluene at 110℃; for 2h; Further byproducts given;	A 21% B 10% C 11% D 31%

acenaphthene quinone (82-86-0) → decacyclene (191-48-0) + trans-biacenaphthylidene (24290-66-2) + cis-biacenaphthylidene (24290-65-1) + acenaphthylene (208-96-8)

Conditions	Yield
bis(η6-biphenyl)titanium(0) In toluene at 110℃; for 2h; Yield given. Further byproducts given;	A 21% B n/a C n/a D 31%

1,2-dihydroacenaphthylen-1-yl diazoacetate (182313-50-4) → acenaphthylene (208-96-8)

Conditions	Yield
at 340℃; under 0.02 Torr;	22%

C24H31BSi2 → acenaphthylene (208-96-8)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 24h; Schlenk technique; Inert atmosphere; Reflux;	21%

(acenaphthylene)chromium tricarbonyl (99414-44-5) + lithium isobutyronitrile (55440-70-5) → C16H13N (106017-41-8) + acenaphthylene (208-96-8)

Conditions

Yield

With N,N,N,N,-tetramethylethylenediamine; iodine; trifluoroacetic acid In tetrahydrofuran to a soln. of nucleophile in THF at -60°C soln. of complex was added, after 45 min at -60°C CF3COOH was added followed by I2, and soln. was allowed to stir overnight while being warmed to room temp.;; soln. was filtered through Celite, evapd.; residue was extd. was ether and washed with other solvents; then chromd. on silica column, eluent CH2Cl2-hexane;;

A 20% B 3%

acenaphthylene (208-96-8) → acenaphthene (83-32-9)

Conditions	Yield
With tetraethylammonium bromide In ethanol at 60℃; electrolysis, lead cathode;	100%
With benzenetellurol In ethanol; ethyl acetate for 4h; Product distribution; Heating; other reagent, reaction time;	98%
With iodine; hypophosphorous acid In acetic acid for 24h; Heating;	98%

acenaphthylene (208-96-8) + benzenesulfenyl chloride (931-59-9) → trans-2-phenylthio-1-chloroacenaphthene

Conditions	Yield
In acetic acid	100%

acenaphthylene (208-96-8) → acenaphthylene (14620-98-5)

Conditions	Yield
With 6-per-deoxy-6-per-(2-sulfoethyl)thio-γ-cyclodextrin, sodium salt for 12h; UV-irradiation; stereoselective reaction;	100%
With Rosebengal In methanol Irradiation;	65%
In hexane at 25℃; Irradiation;
With racemic palladium-ruthenium heterometallic cage with 3-{1H-imidazo[4,5-f]1,10-phenanthrolin-2-yl}pyridine In water; dimethyl sulfoxide at 20℃; Kinetics; Catalytic behavior; Reagent/catalyst; Solvent; Irradiation;

acenaphthylene (208-96-8) + tetrachlorothiophenium-NR → 7,8,9,10-Tetrachloro-6b,10a-dihydro-fluoranthene (72541-91-4)

Conditions	Yield
at 20℃; for 1h;	100%

acenaphthylene (208-96-8) → trans-1,2-dibromo-1,2-dihydroacenaphthylene (25226-58-8)

Conditions	Yield
With tri(decyl)(methyl)phosphonium tribromide In Hexadecane for 240h;	100%
With hydrogen bromide; oxygen; sodium nitrite In water; acetonitrile at 22℃; for 8h; diastereoselective reaction;	96%
With pyridinium hydrobromide perbromide In tetrahydrofuran at -78 - 20℃;	93%

methanol (67-56-1) + 4-allylguaiacol (97-53-0) + acenaphthylene (208-96-8) → 8-allyl-11,11-dimethoxy-6b,7,10,10a-tetrahydro-7,10-ethanofluoranthen-12-one

Conditions	Yield
Stage #1: methanol; 4-allylguaiacol With [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate In benzene at 0℃; for 0.166667h; Stage #2: acenaphthylene In benzene at 20℃; for 22h; Diels-Alder reaction; stereoselective reaction;	100%

1,3-diphenyl-2H-cyclopenta<1>phenanthren-2-one (5660-91-3) + acenaphthylene (208-96-8) → C40H26 (1352187-64-4)

Conditions	Yield
In xylene Reflux;	100%

C18H14OS2 (1352187-65-5) + acenaphthylene (208-96-8) → C30H22OS2 (1352187-66-6)

Conditions	Yield
In diethyl ether; dichloromethane; o-xylene at 100 - 140℃; for 2h;	100%

acenaphthylene (208-96-8) → 6b,7a-dihydroacenaphtho [1,2-b]oxirene (22058-69-1)

Conditions	Yield
Stage #1: acenaphthylene With N-Bromosuccinimide In water; dimethyl sulfoxide at 20℃; for 2h; Stage #2: With sodium hydroxide In diethyl ether at 20℃;	99%
With 3,3-dimethyldioxirane In acetone at 20℃; for 1h;	97%
With 2-Nitrobenzenesulfonyl chloride In acetonitrile at -30℃; for 10h; Product distribution; various arenes, solvents + times;	95%

4-methylphenylboronic acid (5720-05-8) + acenaphthylene (208-96-8) → C19H16

Conditions	Yield
With 5,5’-bis(diphenylphosphino)-2,2,2’,2’-tetrafluoro-4,4’-bi-1,3-benzodioxole; [Rh(OH)(cod)]2 In 1,4-dioxane at 60℃; for 6h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique; enantioselective reaction;	99%

acenaphthylene (208-96-8) → 1(2H)-acenaphthylenone (2235-15-6)

Conditions	Yield
With oxygen; isobutyraldehyde In acetonitrile at 60℃; for 3h;	98%
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In fluorobenzene at 100℃; under 7500.6 Torr;	87%
With iodosylbenzene; iron(III) tetraphenylporphyrin In dichloromethane for 1h;	58%
With iodosylbenzene; μ-oxo dimer of iron(III)porphyrinate In methanol at 21.9℃; for 3h; Product distribution; Mechanism; catalysts also Fe(III)porphyrinate, Fe(III)tetraphenylporphyrinate; protic and aprotic solvents; inhibition effect by phenanthrene; by-products;	28%
With dinitrogen monoxide at 300℃; under 367754 Torr;

phenylselenium trichloride (42572-42-9) + acenaphthylene (208-96-8) → C18H13Cl3Se (109391-84-6)

Conditions	Yield
In diethyl ether at 0℃;	98%

N-ethoxycarbonyl-(2,3,4,5-tetrachloro-1-thiophenio)amide (90454-50-5) + acenaphthylene (208-96-8) → (6bS,10aR)-7,8,9,10-Tetrachloro-6b,10a-dihydro-fluoranthene (72541-91-4)

Conditions	Yield
at 20℃; for 0.166667h;	98%

4-trifluoromethylphenylboronic acid (128796-39-4) + acenaphthylene (208-96-8) → C19H13F3

Conditions	Yield
With 5,5’-bis(diphenylphosphino)-2,2,2’,2’-tetrafluoro-4,4’-bi-1,3-benzodioxole; [Rh(OH)(cod)]2 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; Schlenk technique; enantioselective reaction;	98%

p-methylbenzenesulfenyl chloride (933-00-6) + acenaphthylene (208-96-8) → trans-2-p-tolylthio-1-chloroacenaphthene

Conditions	Yield
In acetic acid	97%

tris(3-chlorophenyl)boroxine (7519-92-8) + acenaphthylene (208-96-8) → C18H13Cl

Conditions	Yield
With 5,5’-bis(diphenylphosphino)-2,2,2’,2’-tetrafluoro-4,4’-bi-1,3-benzodioxole; tert-Amyl alcohol; [Rh(OH)(cod)]2 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; Schlenk technique; enantioselective reaction;	97%

N-(ethoxycarbonyl)-(2,3,4,5-tetrachloro-1-thiophenio)amide S-oxide (106550-69-0) + acenaphthylene (208-96-8) → sulfinylcarbamic acid ethyl ester (5659-92-7) + (6bS,10aR)-7,8,9,10-Tetrachloro-6b,10a-dihydro-fluoranthene (72541-91-4)

Conditions	Yield
In dichloromethane for 1h;	A 89% B 96%

acenaphthylene (208-96-8) + 4-chloro-benzenesulfenyl chloride (933-01-7) → trans-2-(4-chlorophenyl)thio-1-chloroacenaphthene

Conditions	Yield
In acetic acid	96%

acenaphthylene (208-96-8) + N-(2-hydroxy-5-isopropylphenylsulfanyl)phthalimide → 6-(1-methylethyl)-2,3-dihydroacenaphthene[1,4]benzoxathiin

Conditions	Yield
With pyridine In chloroform at 70℃; for 24h;	96%

diphenyl acetylene (501-65-5) + acenaphthylene (208-96-8) → 7,8-diphenyl-6b,8a-dihydrobuta[a]acenaphtylene

Conditions	Yield
With Br2Co*C27H26P2; zinc(II) iodide; zinc In dichloromethane at 25℃; for 48h;	95%

bis(pinacol)diborane (73183-34-3) + acenaphthylene (208-96-8) → 2-(1,2-dihydroacenaphthylen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1449296-11-0)

Conditions	Yield
With methanol; (2-mesityl-5-methyl-2,3-dihydroimidazo[1,5-a]pyridin-3-yl)copper(I) chloride; sodium t-butanolate In diethyl ether at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;	95%

1,3-diphenylisobenzofuran (5471-63-6) + acenaphthylene (208-96-8) → 10.13-Diphenyl-10.13-endoxy-11:12-benzo-9.10.13.14-tetrahydrofluoranthen (13093-44-2, 36213-63-5, 36213-64-6)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene Reflux;	94.85%
In benzonitrile at 140℃; for 7h;	60%

acenaphthylene (208-96-8) → 1,2,2a,3,4,5-hexahydro-acenaphthylene (480-72-8)

Conditions	Yield
With Raney Ni-Al In potassium hydroxide; water at 90℃; for 6.5h; Reduction;	94%
With hydrogen; nickel at 250℃;

acenaphthylene (208-96-8) → acenaphthene quinone (82-86-0)

Conditions	Yield
With benzeneseleninic anhydride In chlorobenzene at 120℃; for 2h;	94%
With N-Bromosuccinimide; water; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 60 - 70℃; for 3h;	79%
With sodium dichromate; cerous nitrate In acetic acid for 19h; Ambient temperature;	36%

Upstream product

• 128-08-5 N-Bromosuccinimide 
• 127-08-2 potassium acetate 
• 83-32-9 acenaphthene 
• 64-19-7 acetic acid 
• 94-36-0 dibenzoyl peroxide 
• 13936-05-5 5-ethylacenaphthene 
• 14209-08-6 1,2-dibromoacenaphthene 
• 141-52-6 sodium ethanolate 
• 10047-18-4 5-acetylacenaphthene 
• 6306-07-6 1-acenaphthenol 
• 14966-36-0 1-acetoxyacenaphthene 
• 10183-87-6 1-(1,2,6,7,8,8a-hexahydro-acenaphthylen-5-yl)-ethanone 
• 25226-58-8 trans-1,2-dibromo-1,2-dihydroacenaphthylene 
• 151-50-8 potassium cyanide 

Downstream Products

• 14973-11-6 1:2-Cyclopropanacenaphthen-3'-carbonsaeure 
• 13093-44-2 7,12-diphenyl-(6br,12ac)-6b,7,12,12a-tetrahydro-7ξ,12ξ-epoxido-benzo[k]fluoranthene 
• 16391-62-1 (7,12-diphenyl)benzofluoranthene 
• 58485-91-9 (6brH.10acH)-6b.7.10.10a-tetrahydro-fluoranthene 
• 13238-75-0 7,8,9,10-Tetraphenylfluoranthene 
• 7229-88-1 7,14-diphenylacenaphthol[1,2-k]-fluoranthene 
• 110195-27-2 7-phenyl-6b,7,10,10a-tetrahydro-fluoranthene 
• 81-84-5 1,8-Naphthalic anhydride 
• 191-48-0 decacyclene 
• 14209-08-6 1,2-dibromoacenaphthene 
• 214-63-1 Zethren 
• 65726-91-2 1-chloroacenaphthylene 
• 35468-33-8 trans-1,2-dichloroacenaphthene 
• 2435-82-7 2H,2'H-[1,1']biacenaphthylenylidene 

Relevant academic research and scientific papers

2,3-Dihydro-1H-naphtho[1,8-cd]borinine as a Potent Precursor for Open-Shell Singlet B-Heterocycles

The reaction of naphthalene-1,8-diylbis[(trimethylsilyl)methanide] and dimethyl arylboronates afforded the corresponding 2,3-dihydro-1H-naphtho[1,8-cd]borinine as single diastereomers. Single-electron oxidation of the boron-containing heterocycles provided acenaphthylene through the generation boron-containing cyclic singlet biradicals.

Flash vacuum thermolysis of biphenylene and diphenic anhydride. Formation of 6b,7,10,10a-tetrahydro-as-indaceno[1,8-jkl]fluoranthene. Evidence for the intermediacy of as-indacene on the C12H8 potential energy surface

Flash Vacuum Thermolysis (FVT) of biphenylene (1) and of diphenic anhydride (2) at 900 °C gave acenaphtylene (10), exo- and endo-6b,7,10,10a-tetrahydro-as-indaceno[1,8-jkl]fluoranthene (11) in high yield. The isolation of compound 11 provides evidence for the occurrence of the anti-aromatic as-indacene (8) on the C12H8 potential energy surface.

Effect of potassium hydroxide on PAH formation during toluene incineration

A laboratory-scale liquid-injection incinerator was used to incinerate toluene at 750°C and PAH emission was analyzed. The results indicate that the emission of solid-phase PAHs considerably increased when potassium hydroxide was added into a fuel-lean toluene flame; more potassium hydroxide resulted in more solid-phase PAHs. But this phenomenon was not observed for the fuel-rich toluene flame. The enhanced PAH formation is proposed as by-product of the partial oxidation or incomplete burning of soot in the secondary flame zone of the fuel-lean flame. It is suggested that reducing soot formation via potassium hydroxide addition may increase PAHs.

Direct Evidence on the Mechanism of Methane Conversion under Non-oxidative Conditions over Iron-modified Silica: The Role of Propargyl Radicals Unveiled

Radical-mediated gas-phase reactions play an important role in the conversion of methane under non-oxidative conditions into olefins and aromatics over iron-modified silica catalysts. Herein, we use operando photoelectron photoion coincidence spectroscopy to disentangle the elusive C2+ radical intermediates participating in the complex gas-phase reaction network. Our experiments pinpoint different C2-C5 radical species that allow for a stepwise growth of the hydrocarbon chains. Propargyl radicals (H2C?C≡C?H) are identified as essential precursors for the formation of aromatics, which then contribute to the formation of heavier hydrocarbon products via hydrogen abstraction–acetylene addition routes (HACA mechanism). These results provide comprehensive mechanistic insights that are relevant for the development of methane valorization processes.

Mechanisms of Heptane Degradation and Product Formation in Microwave Discharge

Abstract: A mechanism for the degradation of n-heptane and the formation of the products of its plasma-chemical transformation by microwave discharge treatment has been proposed. Chemical reactions resulting in reactive species, namely free radicals that form lower hydrocarbons and polyaromatic structures are presented. The product composition of the gas, liquid, and solid phases has been studied using gas chromatography–mass spectrometry analysis of the precipitate obtained by evaporation of the liquid phase after the treatment of n-heptane.

RECORDING MATERIAL AND OPTICAL INFORMATION RECORDING MEDIUM

A recording material includes a dye-bonded polymer compound which contains a polymer compound to which a one-photon absorption dye is bonded, and a glass transition temperature of the recording material is higher than 200° C. An optical information recording medium includes a recording layer and an intermediate layer adjacent to the recording layer, and the recording layer contains the above-described recording material.

Synthesis of novel fluoranthene-based conformationally constrained α-amino acid derivatives and polycyclic aromatics via the diels-alder reaction

Conformationally constrained cyclic α-amino acid moieties have been fused to the fluoranthene system. Aminoindanecarboxylic acid (Aic) and 1,2,3,4-tetrahydroisoquinolinecarboxylic acid (Tic) derivatives were synthesized by an alkylation sequence, whereas a aminotetralincarboxylic acid (Atc) derivative was assembled using the Diels-Alder reaction as a key step. These α-amino acid derivatives are considered as constrained analogues of phenylalanine (Phe) and play an important role in the design and synthesis of bioactive peptides and some fluorescence chemosensor molecules. Moreover, this strategy has been extended to polycyclic aromatics via the Diels-Alder reaction and subsequent aromatization with DDQ. Georg Thieme Verlag Stuttgart New York.

Probing mechanisms of aryl-aryl bond cleavages under flash vacuum pyrolysis conditions

Several biaryls have been subjected to flash vacuum pyrolysis (FVP) at 1100°C and 0.8-0.9hPa. Product compositions are reported for the FVP of 9-phenylanthracene (1), 2-bromobiphenyl (5), biphenyl (8), 1,10- diphenylanthracene (12), 9-(2-naphthyl)anthracene (17), and 9,9′- bianthracenyl (20). The experimental results have been used to evaluate four possible mechanistic pathways for the cleavage of aryl-aryl bonds under these conditions: (1) the 'explosion' of substituted phenyl radicals; (2) hydrogen atom attachment to an ipso-carbon atom of the biaryl followed by C-C bond cleavage; (3) direct homolysis; and (4) loss of a fragment as an aryne. None of these mechanisms by itself successfully accommodates all of the experimental facts. The data suggest that aryl-aryl bond cleavages under FVP conditions involve at least two different mechanistic pathways and that the relative contributions of the competing pathways probably vary from one biaryl to the next.

Organocatalytic oxidative dehydrogenation of dihydroarenes by dioxygen using 2,3-dichloro-5,6-dicyano-benzoquinone (DDQ) and NaNO2

The oxidative dehydrogenation of dihydroarenes catalyzed by 2,3-dichloro-5,6-dicyano-benzoquinone(DDQ) and NaNO2 with dioxygen is reported. The combination of DDQ and NaNO2 showed high efficiency and high selectivity, compared with other benzoquinones and anthraquinones, e.g., >99% conversion of 9,10-dihydroanthracene with 99% selectivity for anthracene can be obtained at 120 °C under 1.3 MPa O2 for 8 h. Excellent results were achieved in the oxidative dehydrogenation of variety of dihydroarenes.

Zirconium tetrachloride catalysed synthesis of symmetric and unsymmetric ethers from secondary benzylic alcohols

Secondary benzylic alcohols are coupled in the presence of zirconium tetrachloride to afford the corresponding symmetrical ethers in good yields. Unsymmetric ethers are obtained with good selectivity by condensation of two different secondary benzylic alcohols under the action of the same catalyst.