- Production method of solid superacid catalyzed synthesis of anthracene ketone
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The production method comprises the following steps: batching 1, 1 ˊ -binaphthalene -8, 8 ˊ -dicarboxylic acid into a proper amount of solvent, and then adding a solid superacid catalyst. The main reaction: temperature rise to reflux, dehydration. Until the reaction was complete, cooling down. After the product is purified, after the main reaction is finished, the solvent in the filter cake is filtered and removed, and then the filter cake is put into an aqueous sodium hydroxide solution for temperature rising, stirring and dissolution of incomplete 1, 1 ˊ -naphthalene -8, 8 ˊ - dicarboxylic acid and impurities and in the filter cake. The product is filtered and dried to obtain a product. To the invention, solid superacid is used as a catalyst, 1, 1 ˊ -binaphthalene -8 and 8 ˊ - dicarboxylic acid are subjected to catalytic dehydration condensation in an organic solvent to obtain the anthracene ketone with higher yield and purity. The pollution problem of waste sulfuric acid in the traditional process is solved.
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Paragraph 0020-0038
(2021/08/25)
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- Microsomal activation of dibenzo[def,mno]chrysene (anthanthrene), a hexacyclic aromatic hydrocarbon without a bay-region, to mutagenic metabolites
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Metabolically formed dihydrodiol epoxides in the bay-region of polycyclic aromatic hydrocarbons are thought to be responsible for the genotoxic properties of these environmental pollutants. The hexacyclic aromatic hydrocarbon dibenzo[def,mno]chrysene (anthanthrene), although lacking this structural feature, was found to exhibit considerable bacterial mutagenicity in histidine-dependent strains TA97, TA98, TA100, and TA104 of S. typhimurium in the range of 18-40 his+-revertant colonies/nmol after metabolic activation with the hepatic postmitochondrial fraction of Sprague-Dawley rats treated with Aroclor 1254. This mutagenic effect amounted to 44-84% of the values determined with benzo[a]pyrene under the same conditions. The specific mutagenicity of anthanthrene in strain TA100 obtained with the cell fraction of untreated animals was 6 his+-revertant colonies/nmol and increased 2.7-fold after treatment with phenobarbital and 4.5-fold after treatment with 3-methylcholanthrene. To elucidate the metabolic pathways leading to genotoxic metabolites, the microsomal biotransformation of anthanthrene was investigated. A combination of chromatographic, spectroscopic, and biochemical methods allowed the identification of the trans-4,5-dihydrodiol, 4,5-oxide, 4,5-, 1,6-, 3,6-, and 6,12-quinones, and 1- and 3-phenols. Furthermore, two diphenols derived from the 3-phenol, possibly the 3,6 and 3,9 positional isomers, as well as two phenol dihydrodiols were isolated. Three pathways of microsomal biotransformation of anthanthrene could be distinguished: The K-region metabolites are formed via pathway I dominated by monooxygenases of the P450 1B subfamily. On pathway II the polynuclear quinones of anthanthrene are formed. Pathway III is preferentially catalyzed by monooxygenases of the P450 1A subfamily and leads to the mono- and diphenols of anthanthrene. The K-region oxide and the 3-phenol are the only metabolites of anthanthrene with strong intrinsic mutagenicity, qualifying them as ultimate mutagens or their precursors. From the intrinsic mutagenicity of these two metabolites and their metabolic formation, the maximal mutagenic effect was calculated. This demonstrates the dominating role of pathway III in the mutagenicity of anthanthrene under conditions where it exhibits the strongest bacterial mutagenicity. platt@ mail.uni-mainz.de.
- Platt, Karl L.,Degenhardt, Christian,Grupe, Stefanie,Frank, Heinz,Seidel, Albrecht
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p. 332 - 342
(2007/10/03)
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- Acid-Catalyzed Cyclization of o-Aroylbenzoic and Diarylcarboxylic Acids upon Heating in Vacuum
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The cyclization of 1,1′-dinaphthyl-8,8′-dicarboxylic acid, diphenic anhydride, o-benzoylbenzoic acid, and 1-naphthoyl-o-benzoic acid into, respectively, anthanthrone, fluorenone-4-carboxylic acid, anthraquinone, and 1,2-benzanthraquinone occurs upon heating to 150-200°C in vacuum in the presence of catalytic amounts (1-3%) of H2SO4 or P2O5.
- Nefedov
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p. 375 - 377
(2007/10/03)
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- One-Electron Oxidation of Dibenzopyrenes by Manganic Acetate
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The dibenzopyrenes (DBPs) are carcinogenic polycyclic aromatic hydrocarbons (PAH) found as environmental pollutants.DBP is the most potent carcinogenic PAH ever tested.To investigate the bioactivation of DBPs by one-electron oxidation, oxidation of DBP, DBP, DBP, DBP, and anthanthrene with Mn(OAc)3 was conducted and compared to that of benzopyrene (BP).All five DBPs produced monoacetoxy derivatives, and all of them except DBP also produced diacetoxy derivatives.Kinetic studies of the formation of monoacetoxy and diacetoxy derivatives of DBPs were carried out and the results were compared to those of the parent compound BP.DBP was similar to BP.DBP reacted inefficiently to form monoacetoxy and diacetoxy products.The other three DBPs resembled one another.These results provide preliminary essential information for studies of the bioactivation of the very potent carcinogen DBP to form DNA adducts.
- Cremonesi, Paolo,Hietbrink, Bruce,Rogan, Eleanor G.,Cavalieri, Ercole L.
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p. 3309 - 3312
(2007/10/02)
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