Hydroxylation and carboxylation--two crucial steps of anaerobic benzene J. Synchrotron Radiat. and Y.Z. Y. Li, S. Li and Y. Kong, 94, 42404246 (1990). Catalysis Letters Soc. Accessibility Mater. The dependence of the rate on the square root of the concentration of 1 usually suggests that the catalyst may dissociate into two species, which are in equilibrium with 1, and that the concentration of the two catalytically active species are proportional to the square root of the concentration of 1 when the equilibrium lies to the far left-hand side. The kinetic isotope effect (KIE) values (0.981.07) support the involvement of cobalt-bound oxygen species as a key intermediate. S8 in ESI).53a The much larger BET surface area compared to the external surface suggests that most of the incorporated [Cu(tmpa)]2+ is placed inside the mesopore, which is large enough (diameter 3.5 nm) for incorporation of [Cu(tmpa)]2+ species smaller than 1.2 nm. Federal government websites often end in .gov or .mil. PubMedGoogle Scholar. Nowadays, remarkable progress in the direct hydroxylation of benzene to phenol has been witnessed involving different oxidant such as nitrous oxide, hydrogen peroxide, molecular oxygen, and a mixture of oxygen and hydrogen [ 3, 4, 5, 6, 7 ]. and S.X. Catalytic Mechanisms and Active Species of Benzene Hydroxylation The site is secure. The double integrated first derivative of a stable radical, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical (10 M), was obtained from an EPR spectrum in a mixed solvent benzene/acetone/H2O (1:1:5, v/v/v) similar to the reaction conditions and used as a reference. Activation of C(sp2)-H in aromatic molecules such as benzene is one of the challenging reactions. Transient formation of benzoate during anaerobic degradation of phenol by active cultures of strain RCB using nitrate as the sole electron acceptor. J.W. Benzene hydroxylation is a fundamental process in chem. S7 in ESI) and the amount of incorporated 1 was determined to be 2.50 105 mol g1 by the absorption spectral change of the mother liquid according to the literature (Fig. Commun. Chem. Chem. A typical procedure for catalytic hydroxylation is as follows: 4.75 mL of an acetone solution containing benzene (2.1 M) and 30 wt% aqueous H2O2 (2.1 M) was added to [CuII(tmpa)(CH3CN)](ClO4)2 (0.31 mol) and vigorously stirred at 298 K. The sample solutions for GC-MS measurements were prepared from the reaction solution by dilution with acetonitrile as needed to analyse products. Efficient and selective nitrile hydration reactions in water catalyzed by an unexpected dimethylsulfinyl anion generated in situ from CsOH and DMSO. Sci. Fetching data from CrossRef. A proposed radical chain mechanism4850 of the 1-catalysed hydroxylation of benzene with H2O2, which agrees with the kinetic formulation [eqn (2)], is shown in Scheme 1. Bethesda, MD 20894, Web Policies Ways to favor the formation of dihydroxybenzenes have been explored, hence CuCl in aqueous sulfuric acid medium catalyzes the hydroxylation of benzene to phenol (24%) and hydroquinone (8%) (65). Thus, the intermediate is given in parenthesis in Scheme 1. Catal. , Ewha Womans University provided correct acknowledgement is given. , Graduate School of Engineering If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate. Correspondence to Am. The concentration of hydrogen peroxide was determined using the TiTPyP reagent according to the literature as follows:31 aqueous solutions of 50 M TiTPyP with 50 mM hydrochloric acid and 5 M perchloric acid were prepared. Then, the structural characteristics and research progress of four representative Fe-based enzyme-mimetic materials were reviewed. Under the steady-state conditions (d[HO2]/dt = 0), [HO2] is given from eqn (4) by eqn (6), whereas [([CuIII(OH)(tmpa)]2+HO)] is given by equation as follows: Under the conditions that k2[H2O2] k1, eqn (7) is, reduced to eqn (8). Soc. Anyone you share the following link with will be able to read this content: Sorry, a shareable link is not currently available for this article. A., Roduner E., Talsi E. P., Sorokin A. Green. Fig. Among them, the CuAg@g-C 3 N 4 catalyst gave the best result leading to the selective hydroxylation of benzene in less than 30 min (Table 1, entry 14). https://doi.org/10.1039/D2GC02335K, Iwamoto M, Hirata J, Matsukami K, Kagawa S (1983) J Phys Chem 87:903905, Murai K-I, Tomita K, Tojo S, Moriga T, Nakabayashi I (2006) Intern J Modern Phys B 20:42494254, Tanaka S, Nakagawa K, Kanezaki E, Katoh M, Murai K-i, Moriga T, Nakabayashi I, Sugiyama S, Kidoguchi Y, Miwa K (2005) J Japan Petroleum Institute 48:223228, Tang J-J, Liu B (2016) J Phys Chem C 120:66426650, Jin Y, Sun C, Su S (2015) Phys Chem Chem Phys 17:1627716284. Suita Immediate hydroxylation of arenes to phenols via V-containing all-silica ZSM-22 zeolite triggered non-radical mechanism, https://doi.org/10.1038/s41467-018-05351-w. Get the most important science stories of the day, free in your inbox. The structure and catalytic performance of the high-valent FeO intermediates in metalloenzymes have been well studied for this purpose. As a crucial building block, phenol is extensively employed in the manufacture of resins, fibers, medicines, etc [1]. S3 in ESI). The pore diameter was also determined to be 3.5 nm from the powder XRD pattern. 6-12 The commonly used oxidants are H 2 O 2, O 2 and N 2 O, etc.13-15 Among them, H 2 O 2 shows relatively higher activity. From: Organic Chemistry of Enzyme-Catalyzed Reactions (Second Revised Edition), 2002 View all Topics Add to Mendeley About this page Inorganic/Bioinorganic Reaction Mechanisms Wang J., Schopfer M. P., Puiu S. C., Sarjeant A. The physical . 8600 Rockville Pike The outcome of these studies also suggests that all anaerobic benzene-degrading microorganisms, regardless of their terminal electron acceptor, may use this pathway. The sample solution (50 L) was added to the mixed solution of TiTPyP (250 L) and perchloric acid (250 L), shaken and diluted with H2O (1950 L). 51, 440444 (2012). Enhancement of Catalytic Activity for Benzene Hydroxylation over Novel All the authors discussed the results and commented on the manuscript. GC-MS measurements were performed with a Shimadzu QP-2010 Ultra instrument. When acetone was replaced by strongly coordinating solvents, such as DMF and DMSO, no catalytic hydroxylation of benzene with H2O2 occurred using [CuII(tmpa)(CH3CN)](ClO4)2 (1) as the catalyst (see Fig. Soc. The tungsten trioxide supported Pt nanoparticles (Pt-WO3) exhibited hydroxylation of benzene in the presence of air and H2O under visible-light (420 < < 540 nm) irradiation. & Huang, J. Phase-transfer hydroxylation of benzene with H2O2 catalyzed by a nitrile-functionalized pyridinium phosphovanadomolybdate. Soc. Bethesda, MD 20894, Web Policies Wang, Y., Wang, J., Wei, J. et al. Sodium metavanadate catalyzed direct hydroxylation of benzene to phenol with hydrogen peroxide in acetonitrile medium. The measured potentials were recorded with respect to an Ag/AgNO3 (0.01 M) reference electrode. Spin trapping of the chain carrier radical resulted in the complete inhibition of the catalytic benzene hydroxylation. 12, 537541 (2005). designed the experiments, analyzed most of the data, and wrote the manuscript. Direct Hydroxylation of Benzene to Phenol over TS-1 Catalysts - MDPI , Aichi 468-0073 Ed. The magnitude of modulation was chosen to optimise the resolution and the signal-to-noise (S/N) ratio of the observed spectra. The catalytic efficiencies of cobalt complexes are tuned by ligand architectures via their geometrical configurations and steric properties. The PubMed wordmark and PubMed logo are registered trademarks of the U.S. Department of Health and Human Services (HHS). Here we demonstrate that anaerobic nitrate-dependent benzene degradation by Dechloromonas strain RCB involves an initial hydroxylation, subsequent carboxylation, and loss of the hydroxyl group to form benzoate. . J. If you are the author of this article, you do not need to request permission to reproduce figures article in a third-party commercial publication (excluding your thesis/dissertation for which The chain length of the propagation step in Scheme 1 is evaluated as the ratio of the rate of formation of phenol (1.08 107 M s1 determined at 5 h) to twice of DMPOOOH (9.62 1011 M s1 determined at 6 h), which is 1120, because two HO2 radicals are produced in the initiation step (see Scheme 1).48. Supported catalysts with Keggin type heteropoly acids (H5PMo10V2O40) loaded onto amine-functionalized MCM-41 for the catalytic hydroxylation of benzene to phenol with H2O2 were prepared by a wet impregnation method. Xin H., Koekkoek A., Yang Q., Van Santen R., Li C., Hensen E. J. M. Ge W., Long Z., Cai X., Wang Q., Zhou Y., Xu Y., Wang J. Guo Y., Zhang X., Zou H., Liu H., Wang J., Yeung K. L. Bui T. D., Kimura A., Ikeda S., Matsumura M. Balducci L., Bianchi D., Bortolo R., D'Aloisio R., Ricci M., Tassinari R., Ungarelli R. Yang J., Sun G., Gao Y., Zhao H., Tang P., Tan J., Lu A. H., Ma D. Wang X., Zhang X., Liu H., Qiu J., Han W., Yeung K. L. Khatri P. K., Singh B., Jain S. L., Sain B., Sinha A. K. Xu B., Zhong W., Wei Z., Wang H., Liu J., Wu L., Feng Y., Liu X. Indian J. 1991:9 pp. , Japan Science and Technology (JST) LightInduced Efficient Hydroxylation of Benzene to Phenol by If you are an author contributing to an RSC publication, you do not need to request permission Selective hydroxylation of benzene to phenol via CH Concentrations of phenol and benzoate in samples prepared from filtered and unfiltered culture broths of an active benzene-degrading culture of strain RCB. Zhang T, Tremblay PL, Chaurasia AK, Smith JA, Bain TS, Lovley DR. Front Microbiol. Provided by the Springer Nature SharedIt content-sharing initiative, Over 10 million scientific documents at your fingertips, Not logged in took part in materials syntheses and/or characterization. You do not have JavaScript enabled. . Baltimore Z.M. Aromatic CH Hydroxylation Reactions with Hydrogen Peroxide Catalyzed Effect of the presence and absence of chemical reducing agents on [. to elucidate the mechanisms by which benzene is converted to phenol, benzene oxide, and . If you are the author of this article, you do not need to request permission to reproduce figures 4 (Elsevier, Oxford, 2002). A. 51V solid state NMR studies of vanadia based catalysts. carried out partial syntheses, characterization, and catalysis evaluation. The solution was not coloured after the reaction, suggesting that leaching of the Cu2+ species is not the major reason for the saturation of phenol formation. In: Corma A, Melo FV, Mendioroz S, Fierro JLG (eds) Studies in Surface Science and Catalysis. You can use material from 2003 Sep;41(9):1046-67. The ratio of the reacted H2O2 to phenol was determined to be nearly 3:1, indicating that H2O2 decomposed in competition with the catalytic hydroxylation of benzene to phenol. N.Y. co-supervised the project and co-designed the experiments. Catal. A benzene-degrading nitrate-reducing microbial consortium displays aerobic and anaerobic benzene degradation pathways. The authors declare no competing interests. The feasibility of the chain reactions in Scheme 1 is also supported by DFT calculations (see Fig. Rev. 8600 Rockville Pike Department of Chemistry, North Eastern Hill University, Shillong-793022, India. Chem. the contents by NLM or the National Institutes of Health. These data are comparable to the experimental observations. 2021 Dec;66(6):931-947. doi: 10.1007/s12223-021-00893-x. Benzene hydroxylation reaction Phenol production 1. Seoul 120-750 53a, 5456) (the BrunauerEmmettTeller (BET) surface area: 1200 m2 g1, the external surface area: 32 m2 g1, the pore diameter: 3.5 nm) to prepare [CuII(tmpa)]2+@Al-MCM-41 (see Experimental section).26,53a,58 [CuII(tmpa)]2+@Al-MCM-41 was characterised by a UV-Vis diffuse reflectance spectrum (Fig. Cyclic voltammetry (CV) measurements were performed with an ALS630B electrochemical analyser in deuterated acetonitrile containing 0.1 M Bu4NPF6 (TBAPF6) as a supporting electrolyte at 298 K. The platinum working electrode (BAS, surface i.d. , Meijo University In the direct oxidation of benzene [71-43-2] to phenol, formation of hydroquinone and catechol is observed (64). 21218 The rate of decay of HO2 by the reaction with benzene is the same as the rate of formation of HO2 by the reaction of the HO2 adduct of benzene with H2O2. Jothimani P, Kalaichelvan G, Bhaskaran A, Selvaseelan DA, Ramasamy K. Indian J Exp Biol. Commun. thank the support of Jiangsu National Synergetic Innovation Center for Advanced Materials. 44, 88778903 (2015). See this image and copyright information in PMC. 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FOIA Coates JD, Chakraborty R, Lack JG, O'Connor SM, Cole KA, Bender KS, Achenbach LA. Epub 2011 Mar 30. Generally, the catalysts used in the benzene hydroxylation to phenol were mainly supported catalysts, such as Fe/HZSM-5 [ 4, 5, 11, 12 ], Cu/Beta [ 13 ], Cu/APO-11 [ 14 ], V/g-C 3 N 4 [ 2, 6, 15 ], V/SBA-15 [ 7 ], V/TiO 2 [ 16 ], and V/NC-600 [ 8 ]. Starting from Benzene. Wu, Y. et al. The dependencies of the initial rate of phenol production on the concentrations of 1, H2O2 and benzene were examined to determine a kinetic formulation (Fig. Ding Q, Liu K, Song Z, Sun R, Zhang J, Yin L, Pu Y. Toxins (Basel). Electronic supplementary information (ESI) available: Cyclic voltammogram (Fig. Sci. Chem. Nielsen, U. G., Topse, N. Y., Brorson, M., Skibsted, J. permission is not required) please go to the Copyright Chem. HO2 produced by the reaction of [Cu(tmpa)]2+ with H2O2 acts as a chain carrier for the radical chain reactions for formation of phenol. Department of Chemistry Anyone you share the following link with will be able to read this content: Sorry, a shareable link is not currently available for this article. Epub 2017 Mar 20. The catalytic turnover rate and the total turnover number reached 259 min^-1 The reaction is completed within 30 s, the fastest. A maximum yield of phenol up to 29% and turnover number (TON) of 286 at 60 C, and a yield of 19% and TON of 191 at 25 C are achieved. Immediate hydroxylation of arenes to phenols via V-containing all In summary, when 1 was added to the acetone solution of benzene, H2O2 and DMPO, a strong EPR signal assigned to DMPOOOH was observed. The complexes catalyzed hydroxylation of benzene using H 2 O 2 (30%) and afforded phenol selectively as the major product. Chem. Nat Commun 9, 2931 (2018). Rev. 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The direct hydroxylation of benzene is a green and economical-efficient alternative to the existing cumene process for phenol production. The concentration of DMPOOOH increased with the reaction time, as shown in Fig. J. Mol. Chen, H. et al. Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Chem. - 209.97.141.77. In this work, graphitic carbon nitride (g-C3N4) material was exfoliated, and then applied as a catalyst support to load FeCl3. To request permission to reproduce material from this article, please go to the One-step selective hydroxylation of benzene to phenol with hydrogen Bordiga, S., Groppo, E., Agostini, G., Bokhoven, J.
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