Permanganate

Tojo, Gabriel; Fernández, M.

doi:10.1007/0-387-35432-8_1

Cited by 6 publications

(5 citation statements)

References 43 publications

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“…The presence of a carbonyl functional group proximate to a carboxylic group (oxaloacetic acid; Table 2) significantly enhanced this effect with a permanganate reactivity of 180 mg PoxC·g −1 C. Compounds containing a C=C double bond were also highly reactive with 141–160 mg PoxC·g −1 C (maleic acid, crotonic acid; Table 2). These observations match existing knowledge regarding the mechanisms of permanganate oxidation for varied functional groups, where susceptibility to oxidation is attributed to the presence of C–H bonds weakened by nearby, electron‐withdrawing functional groups (Forsey et al., 2010; Ladbury & Cullis, 1958; Tojo & Fernández, 2007; Waldemer & Tratnyek, 2006).…”

Section: Resultssupporting

confidence: 83%

“…Permanganate is known to oxidize alkenes, ketones, and alcohols through a variety of mechanisms (Dash et al., 2009; Tojo & Fernández, 2007), while carboxylic acids are unreactive with permanganate (Almendros et al., 1989). For the most part, our model compounds behaved as expected; ketones and alkenes were highly reactive, while carboxylic acids were unreactive.…”

Section: Discussionmentioning

confidence: 99%

“…Much evidence suggests that the permanganate ion targets carbon–carbon double bonds and carbon–hydrogen bonds that have been weakened (i.e., elongated) through the electron‐withdrawing capacity of certain neighboring functional groups (Forsey et al., 2010; Ladbury & Cullis, 1958; Tojo & Fernández, 2007; Waldemer & Tratnyek, 2006). Hydrogen atom abstraction is a known mechanism for oxidation of hydrocarbons, alcohols, and aromatic compounds by permanganate (Ladbury & Cullis, 1958; Tojo & Fernández, 2007; Waldemer & Tratnyek, 2006). Further, high permanganate oxidation rate is closely correlated with low hydrogen dissociation energies in aromatic compounds (Forsey et al., 2010).…”

Section: Discussionmentioning

confidence: 99%

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A mechanistic inquiry into the applicability of permanganate oxidizable carbon as a soil health indicator

Christy,

Moore,

Myrold

et al. 2023

Soil Science Soc of Amer J

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We determined the characteristics that render organic matter responsive to dilute permanganate oxidation to find a mechanistic explanation for the frequently observed responsiveness of permanganate oxidizable carbon (PoxC) to changes in soil health. We conclude that PoxC is primarily a measurement of phenolic and polyphenolic structures rather than of compounds traditionally viewed as preferred microbial food. Upon subjecting pure compounds to the PoxC method, we found that the susceptibility of organic molecules to permanganate oxidation was determined by the presence of specific structural features abundant in phenolic compounds, which were highly reactive (3–98 mg PoxC·g−1 C), and in a subset of low‐molecular‐weight organic acids (0–180 mg PoxC·g−1 C). In comparison, proteins were minimally reactive (0–13 mg PoxC·g−1 C) and carbohydrates were unreactive when subjected to the PoxC method. Permanganate reactivity was not found to be a predictor of decomposability in biosolids through the mirroring of C:N ratio. However, permanganate reactivity increased up to 27% throughout the decomposition process. We suggest a reinterpretation of the mechanisms that render PoxC useful as a soil health indicator. Rather than representing a preferred microbial food source, PoxC measures a carbon fraction with unique molecular properties that may be an indicator of plant‐mediated soil processes. Our research corroborates the usefulness of PoxC as a soil health indicator, albeit for entirely different reasons than previously assumed. This opens exciting avenues of further inquiry and sets the stage for intensified investigations into the general role of polyphenolic compounds in soil health.

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Section: Resultssupporting

confidence: 83%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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A mechanistic inquiry into the applicability of permanganate oxidizable carbon as a soil health indicator

Christy,

Moore,

Myrold

et al. 2023

Soil Science Soc of Amer J

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“…For the conversion to carboxylic acid, oxidising agents such as permanganate, bromine, oxone or copper(II) oxide are commonly employed (Haines 1988;Smith and March 2006b). Since these compounds are strong oxidising agents, they are not chemoselective and for example also convert alcohols (Tojo and Fernández 2007). Typically, the addition of organic solvents is suggested, but examples for the preparation in aqueous solution can also be found.…”

Section: Removal By Conversionmentioning

confidence: 99%

Aldehydes as Wort Off-Flavours in Alcohol-Free Beers—Origin and Control

Gernat

Brouwer

Ottens

2019

Food Bioprocess Technol

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Although present in concentrations in microgrammes per litre level, aldehydes, in particular those derived from Strecker degradation, are known to majorly contribute to the undesired wort flavour of alcohol-free beers. In order to improve currently available products, one needs to understand the underlying cause for the over-prevalence and identify leverage points and methods to selectively reduce the aldehydes in alcohol-free beers. This work gives a short overview on relevant flavour-active wort flavours identified in alcohol-free beer and on their involved chemical formation pathways. Consequently, aldehyde removal technologies in general and in brewing industry are presented. Adsorptive removal of off-flavours by aldehydescavenging groups is already widely exploited in the packaging industry and may achieve reduction of these components to near depletion, depending on the process conditions. Its principles are adaptable to recovering off-flavours before filling. Also, supercritical CO 2 extraction has been successfully applied to separate flavours from food matrices. In brewing, the focus has been set to biologic conversion by restricted fermentation steps, but the reduction of key components of more than 70% is not achieved. Newer developments focus on thermal separation techniques that not only include non-specific physical dealcoholisation but also more selective technologies such as pervaporation, where aldehydes are reduced to near depletion. However, for most unit operations, selectivity and capacity are not yet investigated. Future research should explore the shortcomings of current techniques and overcome bottlenecks either by developing more specific methods for aldehyde removal and/ or a clever combination of unit operations to optimise the separation and process integration.

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“…Many carboxylic acids are also versatile precursors to other useful synthetic building blocks . Compared with their traditional synthetic methods, the utilization of CO 2 as the carboxylic acid source is of great interest because of the low toxic, inexpensive, and renewable nature of CO 2 . Among the various types of approaches to converting CO 2 into carboxylic acids, visible light photoredox catalysis has become a sustainable and facile protocol for this purpose .…”

mentioning

confidence: 99%

Visible Light Photoredox-Catalyzed Formyl/Carboxylation of Activated Alkenes with Glyoxylic Acid Acetals and CO₂

Yang,

Yao,

Yang

et al. 2024

Org. Lett.

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A photoredox-catalyzed sequential α-formyl/carboxylation of alkenes with glyoxylic acid acetals and CO2 has been developed to afford a range of masked γ-formyl esters in good yields, which could be readily transformed into diverse compounds, such as γ-formyl ester, hemiacetal, and 1,4-diol. This reaction features mild conditions, readily available starting materials, and operational simplicity.

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Permanganate

Cited by 6 publications

References 43 publications

A mechanistic inquiry into the applicability of permanganate oxidizable carbon as a soil health indicator

A mechanistic inquiry into the applicability of permanganate oxidizable carbon as a soil health indicator

Aldehydes as Wort Off-Flavours in Alcohol-Free Beers—Origin and Control

Visible Light Photoredox-Catalyzed Formyl/Carboxylation of Activated Alkenes with Glyoxylic Acid Acetals and CO₂

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Permanganate

Cited by 6 publications

References 43 publications

A mechanistic inquiry into the applicability of permanganate oxidizable carbon as a soil health indicator

A mechanistic inquiry into the applicability of permanganate oxidizable carbon as a soil health indicator

Aldehydes as Wort Off-Flavours in Alcohol-Free Beers—Origin and Control

Visible Light Photoredox-Catalyzed Formyl/Carboxylation of Activated Alkenes with Glyoxylic Acid Acetals and CO2

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Visible Light Photoredox-Catalyzed Formyl/Carboxylation of Activated Alkenes with Glyoxylic Acid Acetals and CO₂