Anthraquinone

Vogel, A.

doi:10.1002/14356007.a02_347

Cited by 9 publications

(14 citation statements)

References 12 publications

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“…On the other hand, the unselective oxidation of the carbons in the 1-to 4-positions, i.e., carbons in the outer ring, gives ketone (1,4-anthraquinone) and anhydride (2,3-naphthalic anhydride and pyromellitic anhydride) species as by-products [33]. The production of small quantities of phthalic anhydride, maleic anhydride, CO and CO 2 has also been reported [16,33,34]. The higher selectivity of the oxidation reaction can be explained in terms of the Clar formalism [35], noting that in anthracene additional stabilization of the outermost rings can be achieved if the π-electrons on the 9,10-positions are more localized.…”

Section: Anthracene and Phenanthrene Oxidationmentioning

confidence: 99%

“…Vanadium oxide, iron vanadate or vanadic acid doped with alkali or alkaline earth metal ions are suitable catalysts for anthracene oxidation [16,33,34]. Industrially, the reaction has been carried out at temperatures in the range 320-390 °C and using catalysts consisting of V 2 O 5 , K 2 SO 4 and Fe 2 O 3 on pumice; yields of 95-97 wt% of anthraquinone were reported [17].…”

Section: Anthracene and Phenanthrene Oxidationmentioning

confidence: 99%

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Autoxidation of aromatics

Sánchez

Klerk

2018

Appl Petrochem Res

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Autoxidation is a conversion pathway that has the potential to add value to multinuclear aromatic-rich coal liquids, heavy oils and bitumens, which are typically considered low-value liquids. In particular, autoxidation of these heavy materials could lead to products that may have petrochemical values, e.g., lubricity improvers and emulsifiers. Proper assessment of an oxidative transformation to ring-open the multinuclear aromatics present in heavy feeds relies on the understanding of the fundamentals of aromatic oxidation. This work reviews the selective oxidation chemistry of atoms that form part of an aromatic ring structure using oxygen (O 2) as oxidant, i.e., the oxidation of aromatic carbons as well as heteroatoms contained in an aromatic ring. Examples of industrially relevant oxidations of aromatic and heterocyclic aromatic hydrocarbons are provided. The requirements to produce oxygenates involving the selective cleavage of the ring CC bonds, as well as competing non-selective oxidation reactions are discussed. On the other hand, the Clar formalism, i.e., a rule that describes the stability of polycyclic systems, assists the interpretation of the reactivity of multinuclear aromatics towards oxidation. Two aspects are developed. First, since the interaction of oxygen with aromatic hydrocarbons depends on their structure, oxidation chemistries which are fundamentally different are possible, namely, transannular oxygen addition, oxygen addition to a carbon-carbon double bond, or free radical chemistry. Second, hydrogen abstraction is not necessary for the initiation of the oxidation of aromatics compared to that of aliphatics.

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Section: Anthracene and Phenanthrene Oxidationmentioning

confidence: 99%

Section: Anthracene and Phenanthrene Oxidationmentioning

confidence: 99%

Autoxidation of aromatics

Sánchez

Klerk

2018

Appl Petrochem Res

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“…Anthraquinone (a common name for 9,10-anthraquinone) is a three-ring compound resulting from anthracene oxidation (see Figure 1 , compound 1 ). The aromaticity of the middle ring is strongly limited, as usual for quinones, because of the presence of carbonyl functions [ 14 ]. The presence of aromatic skeleton makes this molecule, and its derivatives, rather rigid structurally, which can be important and promising for the design of well-defined larger structures.…”

Section: Introductionmentioning

confidence: 99%

Competition of Intra- and Intermolecular Forces in Anthraquinone and Its Selected Derivatives

et al. 2021

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Intra- and intermolecular forces competition was investigated in the 9,10-anthraquinone (1) and its derivatives both in vacuo and in the crystalline phase. The 1,8-dihydroxy-9,10-anthraquinone (2) and 1,8-dinitro-4,5-dihydroxy-anthraquinone (3) contain Resonance-Assisted Hydrogen Bonds (RAHBs). The intramolecular hydrogen bonds properties were studied in the electronic ground and excited states employing Møller-Plesset second-order perturbation theory (MP2), Density Functional Theory (DFT) method in its classical formulation as well as its time-dependent extension (TD-DFT). The proton potential functions were obtained via scanning the OH distance and the dihedral angle related to the OH group rotation. The topological analysis was carried out on the basis of theories of Atoms in Molecules (AIM—molecular topology, properties of critical points, AIM charges) and Electron Localization Function (ELF—2D maps showing bonding patterns, calculation of electron populations in the hydrogen bonds). The Symmetry-Adapted Perturbation Theory (SAPT) was applied for the energy decomposition in the dimers. Finally, Car–Parrinello molecular dynamics (CPMD) simulations were performed to shed light onto bridge protons dynamics upon environmental influence. The vibrational features of the OH stretching were revealed using Fourier transformation of the autocorrelation function of atomic velocity. It was found that the presence of OH and NO2 substituents influenced the geometric and electronic structure of the anthraquinone moiety. The AIM and ELF analyses showed that the quantitative differences between hydrogen bonds properties could be neglected. The bridged protons are localized on the donor side in the electronic ground state, but the Excited-State Intramolecular Proton Transfer (ESIPT) was noticed as a result of the TD-DFT calculations. The hierarchy of interactions determined by SAPT method indicated that weak hydrogen bonds play modifying role in the organization of these crystal structures, but primary ordering factor is dispersion. The CPMD crystalline phase results indicated bridged proton-sharing in the compound 2.

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“…Industrially, anthraquinone production is based on the vapor-phase oxidation of anthracene with air. The process is performed over supported iron vanadate-potassium catalysts at 320–390 °C with 99% yield to anthraquinone . The process is represented by the direct conversion of anthracene to anthraquinone, and although the minor production of some other oxidation or combustion products is reported, no additional pathways are discussed in the catalytic oxidation literature.…”

Section: Discussionmentioning

confidence: 99%

Effect of Ring-Configuration on Pyrolysis and V₂O₅Catalyzed Oxidation of Polycyclic Aromatic Hydrocarbons

Sánchez

Klerk

2021

Energy Fuels

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Conversion of polycyclic aromatic hydrocarbons (PAHs) through oxidative ring-opening can be used as a potential strategy for upgrading of aromatic-rich fractions of heavy oil and bitumen. At the core of such a process is the oxidation of PAHs to produce quinonoids, further oxidation of quinonoids to form ringopened carboxylic acids, and finally decarboxylation of the carboxylic acids. The fused ring systems in PAHs include linear and angular ring-configurations, which affect pyrolysis and oxidation selectivity. This study evaluated the effect of the ringconfiguration of PAHs on pyrolysis and on oxidation over a metal oxide catalyst (V 2 O 5 ). Pyrolysis takes place in parallel with catalytic oxidation, and so it has an effect on the observed conversion chemistry. Liquid-phase pyrolysis and V 2 O 5 -catalyzed conversion of anthracene, phenanthrene, anthraquinone, and phenanthrenequinone were studied individually. All experimental work was conducted under a nitrogen atmosphere to avoid autoxidation. Results from high-pressure differential scanning calorimetry (HP-DSC) as well as from batch oxidation reactions indicated differences in reactivities due to the ring-configurations of both PAHs and their corresponding quinonoids. The reactivity sequence over V 2 O 5 for PAHs was anthracene > phenanthrene as the increase in π-sextets in anthracene provided additional driving force toward oxidation. On the contrary, the reactivity over V 2 O 5 of the corresponding quinonoids was phenanthrenequinone > anthraquinone. The angular configuration of phenanthrenequinone led to the carbonyl groups to be adjacent and to the carbons participating in that C−C bond to have an aliphatic nature, which increased the reactivity of the bond. The angular ringconfiguration of phenanthrenequinone favored intramolecular ring-closing reactions, while the linear ring-configuration of anthraquinone exhibited higher stability toward oxidation. Conversion of anthraquinone led to products of oxygen removal via anthrone as well as to some ring-opened products. Compared to pyrolysis, V 2 O 5 accelerated the conversion of PAHs and their corresponding quinonoids. Regardless of the ring-configuration, catalytic oxidation of PAHs over V 2 O 5 did not favor production of ring-opened products. The study highlighted the importance of a hydrogen source, possibly water, for a successful ring-opening.

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Anthraquinone

Abstract: The article contains sections titled: 1. Introduction 2. Properties … Show more

Cited by 9 publications

References 12 publications

Autoxidation of aromatics

Autoxidation of aromatics

Competition of Intra- and Intermolecular Forces in Anthraquinone and Its Selected Derivatives

Effect of Ring-Configuration on Pyrolysis and V₂O₅Catalyzed Oxidation of Polycyclic Aromatic Hydrocarbons

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Anthraquinone

Abstract: The article contains sections titled: 1. Introduction 2. Properties … Show more

Cited by 9 publications

References 12 publications

Autoxidation of aromatics

Autoxidation of aromatics

Competition of Intra- and Intermolecular Forces in Anthraquinone and Its Selected Derivatives

Effect of Ring-Configuration on Pyrolysis and V2O5Catalyzed Oxidation of Polycyclic Aromatic Hydrocarbons

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Effect of Ring-Configuration on Pyrolysis and V₂O₅Catalyzed Oxidation of Polycyclic Aromatic Hydrocarbons