Oxidation of anthracene in the liquid‐phase

Abstract

Various processes for the oxidation of anthracene in the liquid‐phase have been reviewed with special consideration to the mechanistic pathways involved. The prospect of the processes with crude anthracene/less pure anthracene as feed‐stock has been emphasized.

Intramolecular Phosphacyclization: Polyaromatic Phosphonium P‐Heterocycles with Wide‐Tuning Optical Properties

“…[42] Furthermore,w ee valuated the photostability of compounds 1c-7c in solution.I ng eneral,t he family of polycyclic hydrocarbons including phenanthrene and anthracene is thermally stable in the solid state, but is sensitive to oxidation by molecular O 2 to give non-emissive endoperoxideso rq uinone derivatives. [43] Alternatively,q uaternized phosphonium cations can decompose under the basic conditions. [44] Thus, the stabilityo f dyes 1c-4c and 7c under continuous irradiation was studied in aerated PBS solutions( opticald ensity A = 0.1, pH 7.4), the hydrophobic 5c, 6c were investigatedi na eratedd ichloromethane( A = 0.1), see FiguresS15 and S16i nt he Supporting Information.…”

Visible‐Light‐Triggered Quantitative Oxidation of 9,10‐Dihydroanthracene to Anthraquinone by O2 under Mild Conditions

“…UV/Vis spectra of liquid samples of DHA and AQ in pure acetone solution were measured from 200 to 800 nm on aU V-2450 spectrophotometer (Shimadzu, Japan). 1 Ha nd 13 CNMR spectra of the isolated products were measured on aD RX-400 (Bruker) spectrometer with CDCl 3 and [D 6 ]DMSO as the solvent in the presence of SiMe 4 as an internal standard. Electron paramagnetic resonance (EPR) spectra of the samples were measured in 50 mLq uartz tubes on aB ruker A300-10/12/S instrument at room temperature (spectrometer at 9.8 GHz, modulation frequency 100 kHz, modulation amplitude 3G).…”

“…Each photoreaction in this work was repeated in duplicate, and the obtained data between two parallel experiments differed by less than approximately 1%;t he average of the two experimental data points is used in the charts. The isolated goal products were identified by 1 Ha nd 13 CNMR spectroscopy.…”

“…[9] Intense interesth as been focusedo nt he synthesis of anthraquinone derivatives owing to their potential utility in cancer chemotherapy as antioxidants and antitumor agents. [10,11] AQ is produced commercially through several routes, including the oxidation of anthracene (AN) with chromic acid [12] or nitric acid [13] and the vapor-phase oxidation of AN by air at 390 8Co ver as upported iron vanadate potassium catalyst. [12] In addition, AQ and its derivativesc an be obtained more conveniently through the Diels-Alder condensation reaction of benzene or its derivatives with phthalic anhydride.…”

“…[14] Therefore, it is of great practical importance to developacost-effective and environmentally friendlym ethod for the synthesis of AQ. Recently,aseries of works have been reported to replacet he conventional oxidative systems of AQ synthesis, such as metal (Fe, Cu, Co, Ru, Mn) complexes, [15][16][17][18][19][20][21][22][23][24][25] Ru(tmp)(O) 2 /N 2 O( tmp:5 ,10,15,20-tetramesitylporphyrin), [26] air/oxygen/nitrica cid, [13] H 5 PV 2 Mo 10 O 40 /O 2 , [27] molecular sieve catalysts, [28][29][30] and so on. The use of dinuclear Cu II complexes of pyrrolic Schiff-base macrocycles in combination with FeCl 3 (Cu II -FeCl 3 )a sa ne ffective catalyst for the oxidation of 9,10-dihydroanthracene (DHA) to AQ was reported by Pankhurst et al,g iving ah igherD HA conversion (100 %) and 87.0 %AQyield, but high cost severely restricted its application for the synthesis of AQ.…”