“Green” Oxidation Catalysis for Rapid Deactivation of Bacterial Spores

Banerjee, Deboshri; Markley, Andrew L.; Yano, Toshihiro; Ghosh, Anindya; Berget, Peter B.; Minkley, Edwin G.; Khetan, Sushil K.; Collins, Terrence J.

doi:10.1002/ange.200504511

Cited by 12 publications

(32 citation statements)

References 22 publications

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“…[3] ii) CTAB micelles are less efficient at accelerating Fe III -TAML/peroxide process in the pH range, in which the axial aqua ligand of the 1 catalysts was deprotonated. As the overall negative charge of 1 increases, the catalysts become more hydrophilic, their affinity for micelles drops, and the micellar acceleration vanishes.…”

Section: Resultsmentioning

confidence: 98%

“…[3][4][5][6][7][8][9] The catalytic activity of 1 is comparable to that of enzymes that use H 2 O 2 as a source of oxidation equivalents. [4,10] Accordingly, Fe III -TAML activators are promising green oxidation catalysts, [11] which sometimes function in the presence of surfactants.…”

Section: Introductionmentioning

confidence: 97%

“…[3] An illustrative example of enhanced catalysis by the cationic surfactant cetyltri-A C H T U N G T R E N N U N G methylammonium bromide (CTAB) can be found in the Fe III -TAML-based process for killing bacterial spores of the anthrax surrogate Bacillus atrophaeus. [3] The rapid 1-catalyzed bleaching of dyes released from fabrics during laundry washing occurs in detergent-containing media. [1] Detergents are also useful for petroleum desulfurization technologies [7] and for the total oxidative degradation of the commercially formulated insecticide chlorpyrifos.…”

Section: Introductionmentioning

confidence: 99%

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The Impact of Surfactants on Fe^III–TAML‐Catalyzed Oxidations by Peroxides: Accelerations, Decelerations, and Loss of Activity

Banerjee

Apollo

Ryabov

et al. 2009

Chemistry A European J

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Iron(III) complexes of tetraamidato macrocyclic ligands (TAMLs), [Fe{4-XC(6)H(3)-1,2-(NCOCMe(2)NCO)(2)CR(2)}(OH(2))](-), 1 (1 a: X = H, R = Me; 1 b: X = COOH, R = Me); 1 c: X = CONH(CH(2))(2)COOH, R = Me; 1 d: CONH(CH(2))(2)NMe(2), R = Me; 1 e: X = CONH(CH(2))(2)NMe(3) (+), R = Me; 1 f: X = H, R = F), have been tested as catalysts for the oxidative decolorization of Orange II and Sudan III dyes by hydrogen peroxide and tert-butyl hydroperoxide in the presence of micelles that are neutral (Triton X-100), positively charged (cetyltrimethylammonium bromide, CTAB), and negatively charged (sodium dodecyl sulfate, SDS). The previously reported mechanism of catalysis involves the formation of an oxidized intermediate from 1 and ROOH (k(I)) followed by dye bleaching (k(II)). The micellar effects on k(I) and k(II) have been separately studied and analyzed by using the Berezin pseudophase model of micellar catalysis. The largest micellar acceleration in terms of k(I) occurs for the 1 a-tBuOOH-CTAB system. At pH 9.0-10.5 the rate constant k(I) increased by approximately five times with increasing CTAB concentration and then gradually decreased. There was no acceleration at higher pH, presumably owing to the deprotonation of the axial water ligand of 1 a in this pH range. The k(I) value was only slightly affected by SDS (in the oxidation of Orange II), but was strongly decelerated by Triton X-100. No oxidation of the water-insoluble, hydrophobic dye Sudan III was observed in the presence of the SDS micelles. The k(II) value was accelerated by cationic CTAB micelles when the hydrophobic primary oxidant tert-butyl hydroperoxide was used. It is hypothesized that tBuOOH may affect the CTAB micelles and increase the binding of the oxidized catalysts. The tBuOOH-CTAB combination accelerated both of the catalysis steps k(I) and k(II).

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Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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The Impact of Surfactants on Fe^III–TAML‐Catalyzed Oxidations by Peroxides: Accelerations, Decelerations, and Loss of Activity

Banerjee

Apollo

Ryabov

et al. 2009

Chemistry A European J

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“…Fe III -TAML activators [1] of hydrogen peroxide [6,7,26] are valuable catalysts for a variety of environmentally important oxidation processes [27][28][29][30][31]. The general stoichiometric mechanism of catalysis is shown in Scheme 3.7 [31].…”

Section: General Mechanismmentioning

confidence: 99%

Chemistry and Applications of Iron–TAMLCatalysts in Green Oxidation Processes Based on Hydrogen Peroxide

Collins

Khetan

Ryabov

2010

Handbook of Green Chemistry

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Iron–tetraamido macrocyclic ligand (TAML) activators have been designed and developed to provide small‐molecule mimics, the peroxidase enzymes. Fe–TAML activators are proving to be highly active catalysts that function effectively at very low concentrations from nanomolar to low micromolar. Notably, they are capable of performing many thousands of turnovers per minute under ambient conditions, of functioning over a broad pH range from acidic and most notably for iron catalyst to basic and even to highly basic, of presenting a broad range of selectivities and oxidative aggression determined by the conditions of use and the choice of catalyst over the 14 catalysts presented. The catalysts have fulfilled the design criteria and now provide the basis of platform technology for myriad applications. Published kinetics and mechanistic interpretations are reviewed to illustrate the success of the design protocol. Published applications are briefly described. A highly developed field of use involves the use of Fe–TAML–peroxide for the purification of water of persistent pollutants and hardy pathogens.

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“…On the farm, flushing of barns with agricultural "gray" water (recirculated from lagoons) may result in EDC-induced reproductive problems in livestock from exposure to estrogenic hormones in the flush; Fe-B*/H2O2's use could provide a simple remedy. The capacity of Fe-TAML/peroxide to destroy bacterial spores, the hardiest of microbes (29), as well as numerous other chemicals that elude our current wastewater treatment systems, indicates the potential for multipurpose applications in wastewater treatment.…”

Section: Ppm)mentioning

confidence: 99%

Destruction of Estrogens Using Fe-TAML/Peroxide Catalysis

Shappell

Vrabel

Madsen

et al. 2008

Environ. Sci. Technol.

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Endocrine disrupting chemicals (EDCs) impair living organisms by interfering with hormonal processes controlling cellular development. Reduction of EDCs in water by an environmentally benign method is an important green chemistry goal. One EDC, 17R-ethinylestradiol (EE 2 ), the active ingredient in the birth control pill, is excreted by humans to produce a major source of artificial environmental estrogenicity, which is incompletely removed by current technologies used by municipal wastewater treatment plants (MWTPs). Natural estrogens found in animal waste from concentrated animal feeding operations (CAFOs) can also increase estrogenic activity of surface waters. An iron-tetraamidomacrocyclic ligand (Fe-TAML) activator in trace concentrations activates hydrogen peroxide and was shown to rapidly degrade these natural and synthetic reproductive hormones found in agricultural and municipal effluent streams. On the basis of liquid chromatography tandem mass spectrometry, apparent half-lives for 17 R-and 17 β-estradiol, estriol, estrone, and EE 2 in the presence of Fe-TAML and hydrogen peroxide were approximately 5 min and included a concomitant loss of estrogenic activity as established by E-Screen assay.

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“Green” Oxidation Catalysis for Rapid Deactivation of Bacterial Spores

Cited by 12 publications

References 22 publications

The Impact of Surfactants on Fe^III–TAML‐Catalyzed Oxidations by Peroxides: Accelerations, Decelerations, and Loss of Activity

The Impact of Surfactants on Fe^III–TAML‐Catalyzed Oxidations by Peroxides: Accelerations, Decelerations, and Loss of Activity

Chemistry and Applications of Iron–TAMLCatalysts in Green Oxidation Processes Based on Hydrogen Peroxide

Destruction of Estrogens Using Fe-TAML/Peroxide Catalysis

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“Green” Oxidation Catalysis for Rapid Deactivation of Bacterial Spores

Cited by 12 publications

References 22 publications

The Impact of Surfactants on FeIII–TAML‐Catalyzed Oxidations by Peroxides: Accelerations, Decelerations, and Loss of Activity

The Impact of Surfactants on FeIII–TAML‐Catalyzed Oxidations by Peroxides: Accelerations, Decelerations, and Loss of Activity

Chemistry and Applications of Iron–TAMLCatalysts in Green Oxidation Processes Based on Hydrogen Peroxide

Destruction of Estrogens Using Fe-TAML/Peroxide Catalysis

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The Impact of Surfactants on Fe^III–TAML‐Catalyzed Oxidations by Peroxides: Accelerations, Decelerations, and Loss of Activity

The Impact of Surfactants on Fe^III–TAML‐Catalyzed Oxidations by Peroxides: Accelerations, Decelerations, and Loss of Activity