Isolation and identification of by-products of gas phase catalytic oxidation of anthracene to 9,10-anthraquinone

1983 ◽  
Vol 48 (1) ◽  
pp. 112-122 ◽  
Author(s):  
Ivan Chvátal ◽  
Jan Vymětal ◽  
Jaroslav Pecha ◽  
Vilím Šimánek ◽  
Ladislav Dolejš ◽  
...  
Keyword(s):  
Maleic Anhydride ◽  
Catalytic Oxidation ◽  
Gas Phase ◽  
Phthalic Anhydride ◽  
Maleic Acid ◽  
Phthalic Acid ◽  
Diels Alder ◽  
Acid Anhydride ◽  
Isolation And Identification ◽  
By Products

A total of 29 associate components were identified in technical 9,10-anthraquinone. The product contained all the prominent impurities present in the starting anthracene except for 9,10-dihydroanthracene and fluorene. 9-(9'-Anthryl)-carbazole and Diels-Alder type adducts of anthracene with maleic anhydride and with maleinimide were also detected. The isolated and identified by-products of oxidation of anthracene were 1,4-anthraquinone, 4,4'-dioxo-1,1'-bianthrylidene, 4,10'-dioxo-1,9'-bianthrylidene, 1-(4'-oxy-1'-naphthylidene)-4-oxyanthracene, 2,3-naphthalenedicarboxylic acid and anhydride, and 5,7,12,14-tetrahydro-5,14;7,12-di(o-benzeno)pentacene-6,13-dione. Of the compounds formed by oxidation of the anthracene impurities, isolated and identified were dibenzo[b,d]pyrone, xanthone, 1,8-naphthalenedicarboxylic acid anhydride,9-fluorenone, and naphthol[2,3-b]thiophene-4,9-dione. As products of a deeper oxidation of the starting compounds, phthalic anhydride, maleic anhydride, maleinimide, phthalic acid, and maleic acid were found. Four additional components whose structure could not be determined were also isolated. The pathway of the anthracene oxidation is suggested.

Gas phase interaction with catalytic oxidation reactions

1972 ◽  
Vol 326 (1565) ◽  
pp. 215-227 ◽  
Keyword(s):  
Carbon Dioxide ◽  
Maleic Anhydride ◽  
Catalytic Oxidation ◽  
Gas Phase ◽  
Major Part ◽  
Oxidation Reactions ◽  
Mixed Gas ◽  
Kinetics Of ◽  
Oxidation Of Benzene ◽  
Homogeneous Decomposition

Studies of the catalytic oxidation of benzene to maleic anhydride and carbon dioxide over vanadia/molybdena catalysts show that the major part of the reaction involves interacting gas and gas-solid processes. The results are consistent with a mechanism in which a benzeneoxygen adduct is formed catalytically, desorbs and then reacts to give maleic anhydride entirely in the gas phase. On the basis of this proposed mechanism, the kinetics of individual reactions have been investigated in some depth. The over-oxidation of maleic anhydride has been found to be not significant under the conditions of reaction. The kinetic relationships governing the homogeneous decomposition of the adduct and the oxidation of the adduct to maleic anhydride and to carbon dioxide have been established. The results show that essentially all of the anhydride originates from mixed gas-solid/gas reaction while substantial amounts of carbon dioxide are produced entirely catalytically.

Réaction du sulfure de bore avec quelques composés difonctionnels

1972 ◽  
Vol 50 (11) ◽  
pp. 1675-1677 ◽  
Author(s):  
S. Jerumanis ◽  
P. A. Begin ◽  
D. Vu Cong
Keyword(s):  
Salicylic Acid ◽  
Succinic Acid ◽  
Phthalic Anhydride ◽  
Maleic Acid ◽  
Phthalic Acid ◽  
Quantitative Yield

Catechol reacts with boron sulfide to give 2,2′-o-phenylenedioxybis-(1,3,2-benzodioxaborole) (1) while only the hydroxyl function of salicylic acid reacts to give a quantitative yield of tris(o-carboxylphenoxy)borane (3). Phthalic acid is dehydrated to phthalic anhydride, but succinic acid and maleic acid have been found inert to the action of the boron sulfide.

The stereochemistry and regiochemistry of the Diels–Alder reactions of 6-acetoxy-2,6-dimethyl-2,4-cyclohexadienone

1981 ◽  
Vol 59 (16) ◽  
pp. 2510-2517 ◽  
Author(s):  
Hillar Auksi ◽  
Peter Yates
Keyword(s):  
Carboxylic Acid ◽  
Maleic Anhydride ◽  
Dicarboxylic Acid ◽  
Van Der Waals ◽  
Closed Shell ◽  
Diels Alder ◽  
Acid Anhydride ◽  
Propiolic Acid ◽  
High Stereoselectivity

6-Acetoxy-2,6-dimethyl-2,4-cyclohexadienone (1) and maleic anhydride in boiling benzene give a single adduct, exo-5-acetoxy-l,5-dimethyl-6-oxobicyclo[2.2.2]oct-7-ene-endo-2,3-dicarboxylic acid anhydride (2). With propiolic acid 1 gives exo-5-hydroxy-l,5-dimethyl-6-oxobicyclo[2.2.2]octa-2,7-diene-2-carboxylic acid (15). The high stereoselectivity and regioselectivity of these reactions is interpretable in terms of orbital overlap, closed-shell repulsion, steric, and van der Waals – London effects.

ChemInform Abstract: In situ Vinylindole Synthesis. Diels-Alder Reactions with Maleic Anhydride and Maleic Acid to Give Tetrahydrocarbazoles and Carbazoles.

ChemInform ◽  
2010 ◽  
Vol 27 (29) ◽  
pp. no-no
Author(s):  
W. E. NOLAND ◽  
G.-M. XIA ◽  
K. R. GEE ◽  
M. J. KONKEL ◽  
M. J. WAHLSTROM ◽  
...  
Keyword(s):  
Maleic Anhydride ◽  
Maleic Acid ◽  
Diels Alder

In situ vinylindole synthesis. Diels-Alder reactions with maleic anhydride and maleic acid to give tetrahydrocarbazoles and carbazoles

Tetrahedron ◽  
1996 ◽  
Vol 52 (13) ◽  
pp. 4555-4572 ◽  
Author(s):  
Wayland E. Noland ◽  
Guang-Ming Xia ◽  
Kyle R. Gee ◽  
Michael J. Konkel ◽  
Mary J. Wahlstrom ◽  
...  
Keyword(s):  
Maleic Anhydride ◽  
Maleic Acid ◽  
Diels Alder

On the Solvent and Temperature Driven Stereoselectivity of the Diels-Alder Cycloaddition Reactions of Furan with Maleic Anhydride and Maleimide

2019 ◽  
Author(s):  
Veejendra Yadav ◽  
Dasari L V K Prasad ◽  
Arpita Yadav ◽  
Kedar Yadav
Keyword(s):  
Free Energy ◽  
Maleic Anhydride ◽  
Gas Phase ◽  
Quantum Chemical ◽  
Room Temperature ◽  
Experimental Studies ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Endo Isomer ◽  
Equilibrium Process

In quantum chemical calculations, the Diels-Alder cycloaddition reaction of maleic anhydride with furan favors the endo-isomer kinetically in the gas phase. This preference, however, changes in favor of the exo-isomer on inclusion of solvent effects. For example, in acetonitrile, the exo-isomer was calculated to form twice as fast as the endo-isomer at room temperature, an observation that corroborates well with the experiments. The free energy change of the reaction is such that it allows faster reversal of the endo-isomer to the reactants in an equilibrium process and, thus, the predominance of the more stable exo-isomer eventually. The reaction of maleimide with furan is similar to that of maleic anhydride. However, it favors predominantly endo selectivity at temperatures below 320 K which is in excellent agreement with the experimental studies of temperature dependence of this DA reaction. Further, a gedanken calculation of the DA reaction of cyclopropene with furan has been investigated to delineate the effect of the retro-pathway on the stereoselectivity.

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