Ozonization of caffeine in aqueous solution

Kolonko, K. J.; Shapiro, Robert H.; Barkley, Robert M.; Sievers, Robert E.

doi:10.1021/jo01336a007

Cited by 44 publications

(20 citation statements)

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“…An initial attack of Fe(VI) to C 4 =C 5 double bond of CAF results in C1 (nine‐membered ring structure). The intermediacy of C1 has also been suggested for the degradation of CAF by ozone, advanced oxidation, and hypochlorite . Hydrolysis, followed by oxidation and decarboxylation could lead to C2 as suggested for oxidation of CAF by hypochlorite (Figure ) .…”

Section: Resultsmentioning

confidence: 91%

“…OP1, OP2, and OP3 have been identified as products of the degradation of CAF by hypochlorite . OP1 has been also reported as a product of the reaction of CAF with ozone . OP4, a biological metabolite of CAF, has been identified as a product of the degradation of CAF by activated oxone, ozone, electrochemical oxidation, and activated peroxymonosulfate …”

Section: Resultsmentioning

confidence: 99%

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Oxidation of caffeine by acid‐activated ferrate(VI): Effect of ions and natural organic matter

et al. 2017

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Caffeine (CAF) is the most commonly consumed stimulant and frequently detected emerging pollutant in influents and effluents of wastewater treatment plants (WWTP) and surface waters. Acid‐activated ferrate(VI) (FeVI O42−, Fe(VI)) oxidizes CAF in water in seconds to minutes at three times lower molar ratio of Fe(VI) to CAF than oxidative transformation observed in hours by nonactivated Fe(VI) (8.0 vs. 25.0). CAF oxidation by acid‐activated Fe(VI) is not affected by ionic constituents of water. Organic components of natural organic matter (NOM) and secondary effluent wastewater (SE) decrease efficiency of CAF transformation. However, acid‐activated Fe(VI) could mineralize other organics present in both NOM and SE as indicated by the dissolved organic carbon (DOC) removal. Comparatively, no mineralization was seen without activation of Fe(VI). Four oxidized products of CAF were identified by a liquid chromatography high resolution mass spectrometry technique. The reaction pathways of the oxidation of CAF by activated Fe(VI) have been proposed. © 2017 American Institute of Chemical Engineers AIChE J, 2017

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Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Oxidation of caffeine by acid‐activated ferrate(VI): Effect of ions and natural organic matter

et al. 2017

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“…In 1890, Leipen treated an aqueous solution of caffeine with ozone and obtained dimethylparabanic acid (DMPA) (12.1) (Scheme 3), as the major product. At the same time, other authors reported that 12.1 was also the final product obtained by the oxidation of caffeine under numerous experimental conditions [94]. [95].…”

Section: Oxidation Of Caffeine (12)mentioning

confidence: 77%

Mimicking P450 processes and the use of metalloporphyrins

Simões

Neves

Pires

et al. 2013

Pure and Applied Chemistry

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Metalloporphyrins (MPs) are known to catalyze in vitro a broad range of cytochrome P 450 -mediated reactions occurring in vivo. Most of the biomimetic research using MPs in oxidative catalysis has been directed towards the oxidation of organic compounds presenting significant reactivity features in one functional group. Much less effort has been made to imitate the oxidation of more complex molecules, with a range of functionalities, such as drugs or other xenobiotics. By varying the structure of the porphyrin, the metal ion, the oxidant, and the reaction conditions, it is possible to modulate the regioselectivity of the oxidation reactions. Recently, and along with studies on the synthesis and reactivity of porphyrins, chlorins, and phthalocyanines, our group was able to develop an interesting line of research in the field of biomimetic oxidation of organic compounds using environmentally benign hydrogen peroxide as oxidant and Mn(III) or Fe(III) porphyrin complexes as catalysts. The more up to date results obtained in such work are reviewed here.

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“…The ester Ic was synthesised as previously reported in a patent 13. The product IIb 14, 15 was obtained by slowly adding 0.87 mL (10 mmol) of oxalyl chloride to a solution of 0.88 g (10 mmol) of ethylurea in 15 mL of diethyl ether. The mixture was at reflux of diethyl ether during 2 h. After evaporation, 20 mL of water was added, and the reaction mixture was extracted with ethyl acetate.…”

Section: Methodsmentioning

confidence: 99%