Characterization of Soluble Macromolecular Oxidatively Reactive Species (SMORS) from Middle Distillate Diesel Fuels: Their Origin and Role in Instability

Hardy, Dennis R.; Wechter, Margaret A.

doi:10.1021/ef00045a036

Cited by 35 publications

(55 citation statements)

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“…The oxidation of these compounds (i.e., oxidative desulfurization and oxidative denitrogenation) to give chemically modified products with properties that favor their separation or removal has been explored [44,45]. Furthermore, it is known that autoxidation of nitrogen heterocyclic aromatics plays a role in the formation of heavy addition products, e.g., nitrogen-containing compounds seem to be related with the formation of sludge in fuels [46], thereby affecting fuel storage stability.…”

Section: Oxidation Of Heterocyclic Aromaticsmentioning

confidence: 99%

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: Oxidation Of Heterocyclic Aromaticsmentioning

confidence: 99%

Autoxidation of aromatics

Sánchez

Klerk

2018

Appl Petrochem Res

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“…These data show that as the severity of hydrotreatment was increased, the sulfur content dropped from 222 ppm to 86 ppm and the aromatic content, total and basic nitrogen levels also decreased significantly. The data in Table 6 also indicate a considerable reduction in SMORS (soluble macromolecular oxidatively reactive species) precursors [22] measured as the fuel was hydrotreated to reach a sulfur content of 86 ppm.…”

Section: Amoco Petroleum Productsmentioning

confidence: 87%

Potential for Peroxide and Gum Formation in Ultra-Low-Sulfur Diesel Fuels

Willauer¹,

Hardy²,

Morris³

et al. 2007

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“…It is a very useful conceptual framework to rationalize auto-oxidation. Hardy and Wechter (1994) reported that the highest molecular weight fraction of soluble macromolecular oxidatively reactive species (SMORS) can be quantified as an EIP in the diesel fuel containing LCO. Aksoy et al (2009) also made an attempt to correlate EIP mass of oxidatively stressed in tubing bombs of jet fuels with mean thermal oxidative deposition in a flowing reactor.…”

Section: Mechanism Of Degradationmentioning

confidence: 99%