84-47-9Relevant articles and documents
Comparison of spin density calculation methods for various alkyl-substituted 9,10-anthraquinone anion radicals in the solution phase
Eloranta, Jussi,Vatanen, Virpi,Groenroos, Antti,Vuolle, Mikko,Maekelae, Reijo,Heikkilae, Hilkka
, p. 898 - 902 (1996)
EPR and ENDOR spectra were recorded for 2-methyl-9,10-anthraquinone (2-methylAQ), 2-ethylAQ, 2-tertbutylAQ and 2,3-dimethylAQ anion radicals in the solution phase. The EPR spectra were simulated with the help of ENDOR data. The experimental isotropic hyperfine coupling constants (IHFCs) were compared with calculated values from semi-empirical INDO, spin-restricted AM1/CI and B3PW91 density-functional methods. The best computational methods for the IHFCs were the semi-empirical AM1/CI method and the B3PW91 density-functional method with a large basis set.
Friedel - gram acylating reaction method based on phthalic anhydride and aromatic alkyl compound
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Paragraph 0085-0087, (2021/09/08)
A part of a substituted alkylbenzene is used as a solvent and a reaction raw material for - gram acylating reaction, a part of a substituted alkylbenzene is dissolved in a reaction raw material phthalic anhydride and a chloroaluminate ionic liquid catalyst, and a residual part of a substituted alkylbenzene is added dropwise - to obtain - (2 - 4' - alkylbenzoyl) benzoic acid intermediate. 2 -position positioning selectivity of the method is higher, and the reaction production cost is low.
Preparation method of anthraquinone and alkyl derivatives thereof
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Page/Page column 0139-0142; 0145-0154, (2020/08/18)
The invention relates to the field of organic matter preparation, and discloses a preparation method of anthraquinone and alkyl derivatives thereof, and the method comprises the following steps: underacidic conditions, carrying out contact reaction on anthracene and alkyl derivatives thereof, an oxidant and a catalyst. The anthraquinone and the alkyl derivative thereof have a structure as shown in a formula (I) which is described in the specification. The catalyst comprises a carrier and metal elements loaded on the carrier, wherein the metal elements comprise molybdenum and tungsten, in theformula (I), R1 and R2 are each independently selected from hydrogen and substituted or unsubstituted C1-C10 hydrocarbon groups. The method provided by the invention has the characteristics of mild operation conditions and high product yield.
Method for synthesizing 2-alkylanthraquinone
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Paragraph 0023; 0025, (2019/10/04)
The invention discloses a method for synthesizing 2-alkylanthraquinone. The method comprises the following steps: preparing a tert-butylanthraquinone intermediate BE acid from phthalic anhydride and alkylbenzene in the presence of a Lewis acid, carrying out dehydration ring closure by adopting a combined dehydrating agent composed of polyphosphoric acid and phosphorus pentoxide, pouring the obtained solution into ice water after the end of the ring closure I order to dilute the polyphosphoric acid to a certain concentration, adding xylene for extraction after water precipitation is finished, washing and concentrating the obtained extract to obtain a brown yellow block solid, and recrystallizing the solid to obtain the 2-alkylanthraquinone. The method of the invention the advantages of avoiding of using of fuming sulfuric acid and production of a large amount of dilute sulfuric acid in the phthalic anhydride method production process of anthraquinone, easily available raw materials, mild reaction conditions, easiness in application in industrial production, realization of continuous using of the byproduct phosphoric acid as the dehydrating agent after addition of phosphorus pentoxide, and good environmental protection meaning.
Method for preparing 2-alkyl anthraquinone by taking solid super acids as catalysts
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Paragraph 0038-0039, (2020/03/28)
The invention provides a method for preparing 2-alkyl anthraquinone by taking solid super acids as catalysts. The 2-alkyl anthraquinone (alkyl is straight or branched alkyl with the number of carbon atoms of 1-6) is obtained by adopting the solid super acids like perfluorinated sulfonic acid resin and heteropoly acid as the catalysts, taking 2-(4'-alkyl benzoyl) benzoic acid as a raw material andperforming acylated dewatering closed loop through Friedel-Crafts reaction. The method provided by the invention is characterized in that traditional smoking sulfuric acid catalysts are replaced by the solid super acids, so that the environment is friendly, and no waste acid is discharged; the operation process is simple, and the solid catalysts are easy to recover; therefore, the method is a green pollution-free new process.
A 2 - alkyl anthraquinone synthetic method (by machine translation)
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, (2017/05/26)
The invention provides a 2 - alkyl anthraquinone synthetic method, the 2 - alkyl anthraquinone synthetic method comprises the following steps: the 2 - (4' - alkyl benzoyl) benzoic acid in the presence of a solvent through the acyl acyl; under the action of the promoter, using anhydrous aluminum ring to carry out the dehydrochlorination; reactant through hydrolysis, liquid separation, pressure reducing desolventizing, drying, to obtain 2 - alkyl anthraquinone. The beneficial effect of the present invention is: not the use of fuming sulfuric acid, mild reaction conditions, acid-free, simple process operation, the product quality is stable, and the yield of the product than the existing production process to improve the 5 - 10%. (by machine translation)
Binuclear iron(III) octakis(perfluorophenyl)tetraazaporphyrin μ-oxodimer: A highly efficient catalyst for biomimetic oxygenation reactions
Yusubov, Mekhman S.,Celik, Cumali,Geraskina, Margarita R.,Yoshimura, Akira,Zhdankin, Viktor V.,Nemykin, Victor N.
supporting information, p. 5687 - 5690 (2014/12/11)
Binuclear iron(III) octakis(perfluorophenyl)tetraazaporphyrin μ-oxodimer complex was prepared by the reaction of bis(perfluorophenyl)maleonitrile and Fe(CO)5and tested in catalytic oxygenation reactions of several hydrocarbons in comparison with the analogous non-fluorinated phthalocyanine complexes. Results of the study demonstrate that this complex is a highly efficient catalyst for the oxygenation of anthracene, 2-tert-butylanthracene, naphthalene, 2-methylnaphthalene, phenanthrene, adamantane, and toluene using iodosylbenzene, oligomeric iodosylbenzene sulfate, or Oxone as stoichiometric oxidants.
Metalloporphyrin/Iodine(III)-Cocatalyzed oxygenation of aromatic hydrocarbons asc.wiley-vch.de
Yoshimura, Akira,Neu, Heather M.,Nemykin, Victor N.,Zhdankin, Viktor V.
experimental part, p. 1455 - 1460 (2010/08/20)
Hypervalent iodine species have a pronounced catalytic effect on the metalloporphyrinmediated oxygenations of aromatic hydrocarbons. In particular, the oxidation of anthracene to anthraquinone with Oxone readily occurs at room temperature in aqueous acetonitrile in the presence of 5-20 mol% of iodobenzene and 5 mol% of a water-soluble iron(III)-porphyrin complex. 2-tert-Butylan- thracene and phenanthrene also can be oxygenated under similar conditions in the presence of 50 mol% of iodobenzene. The oxidation of styrene in the presence of 20 mol% of iodobenzene leads to a mixture of products of epoxidation and cleavage of the double bond. Partially hydrogenated aromatic hydrocarbons (e.g., 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, and 2,3-dihydro-1H- indene) afford under these conditions products of oxidation at the benzylic position in moderate yields. The proposed mechanism for these catalytic oxidations includes two catalytic redox cycles: 1) initial oxidation of iodobenzene with Oxone producing the hydroxy(phenyl)iodonium ion and hydrated iodosylbenzene, and 2) the oxidation of iron(III)-porphyrin to the oxoiron(IV)-porphyrin cation-radical complex by the intermediate iodine(III) species. The oxoiron(IV)-porphyrin cation-radical complex acts as the actual oxygenating agent toward aromatic hydrocarbons.
Binuclear iron(III) phthalocyanine(μ-oxodimer)/tetrabutylammonium oxone: A powerful catalytic system for oxidation of hydrocarbons in organic solution
Neu, Heather M.,Zhdankin, Viktor V.,Nemykin, Victor N.
scheme or table, p. 6545 - 6548 (2011/02/22)
Binuclear iron(III) phthalocyanine-(μ-oxodimer) complex was tested in catalytic oxygenation reactions of several hydrocarbons using tetrabutylammonium oxone as the oxidant in dichloromethane solution at room temperature. Results of the study demonstrate that this is an extremely powerful catalytic system for oxidative conversion of aromatic hydrocarbons (anthracene, 2-tert- butylanthracene, 2-methylnaphthalene, 9, 10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, indane, ethylbenzene, toluene, and benzene) to the respective p-quinones in high yields in 5-30 min. Under these conditions, adamantane is oxidized with 71% conversion after 10 min affording a mixture of 1 -adamantanol, 2-adamantanone, 1-hydroxy-2-adamantanone, and 4-protoadamantanone.
Binuclear iron(III) phthalocyanine(μ-oxodimer)-catalyzed oxygenation of aromatic hydrocarbons with iodosylbenzene sulfate and iodosylbenzene as the oxidants
Neu, Heather M.,Yusubov, Mekhman S.,Zhdankin, Viktor V.,Nemykin, Victor N.
scheme or table, p. 3168 - 3174 (2010/04/28)
Two binuclear iron(III) phthalocyanine-(μ-oxodimer) complexes were tested in catalytic oxygenation reactions of several aromatic hydrocarbons using iodosylbenzene (PhIO)n or oligomeric iodosylbenzene sulfate [(PhIO)3SO3]n as the oxidants. Results of this study demonstrate that [(PhIO)3SO3]n is the most reactive oxygenating reagent that can be used as a safe and convenient alternative to the thermally unstable and potentially explosive iodosylbenzene. The pyridine-containing binuclear μ-oxobis-{iron(III)-pyridino[3,4]-9(10), 16(17),23(24)-tri-tertbutyltribenzoporphyrazine} is significantly more active as compared to the traditional μ-oxobis[iron-(III)-2,9(10),16(17),23(24)-tetra- tert-butylphthalocyanine].