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Cas Database

123-30-8

123-30-8

Identification

  • Product Name:Phenol,4-amino-

  • CAS Number: 123-30-8

  • EINECS:204-616-2

  • Molecular Weight:109.128

  • Molecular Formula: C6H7NO

  • HS Code:2922.29 Oral rat LD50: 375 mg/kg

  • Mol File:123-30-8.mol

Synonyms:Phenol,p-amino- (8CI);1-Amino-4-hydroxybenzene;4-Amino-1-hydroxybenzene;4-Hydroxy-1-aminobenzene;4-Hydroxyaniline;4-Hydroxybenzenamine;4-Hydroxyphenylamine;Activol;Azol;BASF Ursol P Base;Benzofur P;C.I. 76550;C.I. Oxidation Base 6;Certinal;Citol;Durafur Brown RB;Fouramine P;Fourrine84;Fourrine P Base;Furro P base;NSC 1545;Nako Brown R;Paranol;PelagolGrey P Base;Pelagol P Base;Renal AC;Rodinal;Tertral P Base;Unal;Ursol P;Ursol P Base;Zoba Brown P Base;p-Aminophenol;p-Hydroxyaniline;p-Hydroxyphenylamine;p-Amino phenol;4-Aminophenol, para amino phenol;4-Aminophenol;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,DangerousN

  • Hazard Codes:Xn,N

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH332 Harmful if inhaled H341 Suspected of causing genetic defects H410 Very toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. SYMPTOMS: Symptoms of exposure to this chemical may include asthma, irritation of the skin and eyes, dermatitis and methemoglobinemia with cyanosis. ACUTE/CHRONIC HAZARDS: This compound is a skin and eye irritant and an allergen. When heated to decomposition it emits toxic fumes. Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Use dry chemical, carbon dioxide, or alcohol foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position ... The only respirators recommended for fire fighting are self-contained breathing apparatuses that have full facepieces and are operated in a pressure-demand or other positive-pressure mode. /Anisidines/ Flash point data are not available for this chemical. It is probably combustible. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Spill handling: keep dust under control. Use a vacuum or wet method to reduce dust during clean-up. Do not sweep. Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection of your regional office of the federal EPA for specific recommendations. /Aminophenols/

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in tightly closed containers in a cool, well-ventilated area. Aminophenols must be stored to avoid contact with strong oxidizers (such as chlorine, bromine, and fluorine), since violent reactions occur. /Aminophenols/

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Usbiological
  • Product Description:4-Aminophenol
  • Packaging:1g
  • Price:$ 312
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  • Manufacture/Brand:TRC
  • Product Description:4-Aminophenol
  • Packaging:10g
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Aminophenol >98.0%(GC)(T)
  • Packaging:500g
  • Price:$ 73
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Aminophenol >98.0%(GC)(T)
  • Packaging:25g
  • Price:$ 17
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Aminophenol
  • Packaging:25 g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Aminophenol
  • Packaging:100 g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Aminophenol for synthesis. CAS 123-30-8, chemical formula 4-(NH )C H OH., for synthesis
  • Packaging:8004219050
  • Price:$ 1940
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Aminophenol for synthesis
  • Packaging:50 kg
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Aminophenol United States Pharmacopeia (USP) Reference Standard
  • Packaging:100mg
  • Price:$ 373
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Aminophenol for synthesis. CAS 123-30-8, chemical formula 4-(NH )C H OH., for synthesis
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Relevant articles and documentsAll total 387 Articles be found

A New Class of 1-Aryl-5,6-dihydropyrrolo[2,1-a]isoquinoline Derivatives as Reversers of P-Glycoprotein-Mediated Multidrug Resistance in Tumor Cells

Nevskaya, Alisa A.,Matveeva, Maria D.,Borisova, Tatiana N.,Niso, Mauro,Colabufo, Nicola A.,Boccarelli, Angelina,Purgatorio, Rosa,de Candia, Modesto,Cellamare, Saverio,Voskressensky, Leonid G.,Altomare, Cosimo D.

, p. 1588 - 1596 (2018)

A number of aza-heterocyclic compounds, which share the 5,6-dihydropyrrolo[2,1-a]isoquinoline (DHPIQ) scaffold with members of the lamellarin alkaloid family, were synthesized and evaluated for their ability to reverse in vitro multidrug resistance in cancer cells through inhibition of P-glycoprotein (P-gp) and/or multidrug-resistance-associated protein 1. Most of the investigated DHPIQ compounds proved to be selective P-gp modulators, and the most potent modulator, 8,9-diethoxy-1-(3,4-diethoxyphenyl)-3-(furan-2-yl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carbaldehyde, attained sub-micromolar inhibitory potency (IC50: 0.19 μm). Schiff bases prepared by the condensation of some 1-aryl-DHPIQ aldehydes with p-aminophenol also proved to be of some interest, and one of them, 4-((1-(4-fluorophenyl)-5,6-dihydro-8,9-dimethoxypyrrolo[2,1-a]isoquinolin-2-yl)methyleneamino)phenol, had an IC50 value of 1.01 μm. In drug combination assays in multidrug-resistant cells, some DHPIQ compounds, at nontoxic concentrations, significantly increased the cytotoxicity of doxorubicin in a concentration-dependent manner. Studies of structure–activity relationships and investigation of the chemical stability of Schiff bases provided physicochemical information useful for molecular optimization of lamellarin-like cytotoxic drugs active toward chemoresistant tumors as well as nontoxic reversers of P-gp-mediated multidrug resistance in tumor cells.

DIRECT CONVERSION OF ANILINES INTO AMINOPHENOLS

Jacquesy, Jean-Claude,Jouannetaud, Marie-Paule,Morellet, Guy,Vidal, Yves

, p. 1479 - 1482 (1984)

Hydroxylation of anilines by hydrogen peroxide in SbF5-HF yields the three possible aminophenols, the meta isomer being the major product.The reaction implies attack of protonated hydrogen peroxide H3O2(1+) on the N-protonated substrate.

Green synthesis of the Ag/HZSM-5 nanocomposite by using Euphorbia heterophylla leaf extract: A recoverable catalyst for reduction of organic dyes

Tajbakhsh, Mahmood,Alinezhad, Heshmatollah,Nasrollahzadeh, Mahmoud,Kamali, Taghi A.

, p. 258 - 265 (2016)

During this paper, the Ag/HZSM-5 nanocomposite has been successfully synthesized by using an aqueous extract of Euphorbia heterophylla leaves as a stabilizing and reducing agent. The green synthesized Ag/HZSM-5 nanocomposite was characterized by FT-IR (Fourier transform infrared spectroscopy), FESEM (field emission scanning electron microscopy), EDS (energy dispersion X-ray spectroscopy), UV-vis, XRD (X-ray powder diffraction) and elemental mapping. The Ag/HZSM-5 nanocomposite was found to be efficient nanocatalyst for the reduction of organic dyes such as Methylene blue (MB), Congo red (CR), Rhodamine B (RhB) and 4-nitrophenol (4-NP) in water at room temperature. The catalytic activities of the nanocatalyst in reactions were monitored by using UV-vis spectroscopy. Interestingly, the Ag/HZSM-5 catalyst can be easily recovered and reused several times without any significant loss of catalytic efficiency.

Eco-Friendly In Situ Fabrication of Reduced Graphene Oxide Gold Nanocomposites for Catalysis and Dye Degradation

Patil, Pravin O.,Mahale, Sanchita S.,More, Mahesh P.,Bhandari, Pravin V.,Deshmukh, Prashant K.,Bari, Sanjay B.

, p. 2750 - 2756 (2018)

Abstract: The invention represents a development of robust eco-friendly method use for water waste management and polluted water. The inadvertent role of peanut peels extract helps to simultaneously convert and form reduced graphene oxide gold nanocomposite (rGO@AuNCs) in single step. Fabricated nanocomposite was evaluated for its catalytic performance using reduction of 4-nitrophenol to 4-aminophenol as well as elimination of methylene blue (MB) and malachite green (MG) dyes from water. Graphene oxide (GO) and rGO@AuNCs, were synthesized using simplified approaches and preliminary characterization was done using UV–Vis spectrophotometer and Fourier transform infrared spectroscopy. Least concentration of rGO@AuNCs is required to eliminate MB and MG around 77 and 93%, respectively. Furthermore, surface morphology and elemental analysis of rGO@AuNCs confirm successful fabrication methods as well as X?ray diffraction pattern confirms the crystalline behavior of nanocomposite. The study illustrates an environment-friendly and cost effective in situ fabrication rGO@AuNCs from industrial agro waste for an environmental remediation.

Monooxygenase-like activity of methemoglobin with sodium sulfite as an efficient reductant

Song, Yonghong,Yang, Chi-Ming,Kluger, Ronald

, p. 4365 - 4366 (1993)

-

Helichrome: Synthesis and enzymatic activity of a designed hemeprotein

Sasaki,Kaiser

, p. 380 - 381 (1989)

-

Synthesis of a superparamagnetic ultrathin FeCO3 nanorods-enzyme bionanohybrid as a novel heterogeneous catalyst

Benavente, Rocio,Lopez-Tejedor, David,Palomo, Jose M.

, p. 6256 - 6259 (2018)

Herein we report a straightforward synthesis of an ultrathin protein-iron(ii) carbonate nanorods (FeCO3-NRs) heterogeneous bionanohybrid at room temperature and in aqueous media. The enzyme induced the in situ formation of well-dispersed FeCO3 NRs on a protein network. The addition of NaBH4 as a reducing agent allowed us to obtain nanorods (5 × 40 nm) with superparamagnetic properties. This bionanohybrid showed excellent catalytic results in reduction, oxidation and C-C bond reactions.

Direct Hydrogenation of Nitroaromatics at Room Temperature Catalyzed by Magnetically Recoverable Cu@Fe2O3 Nanoparticles

Borah, Biraj Jyoti,Bharali, Pankaj

, (2020)

Metal embedded in metal oxide nanoparticles are active as catalyst in plethora of industrially important reactions. Herein, embedded Cu@Fe2O3 nanoparticles was synthesized via a one step hydrothermal strategy which selectively catalyzes the hydrogenation of diverse nitroaromatics in H2O at room temperature. The remarkable catalytic performance is due to the successful hybridization of metallic Cu and Fe2O3 which in turn allows easy electroflipping between various oxidation states of Cu and Fe. Azo- and azoxy-compounds are not formed during the catalyzed process. This evidently establish that the hydrogenation of nitroaromatics proceeds via direct route with >99percent selectivity to the corresponding anilines.

Green Route for the Preparation of p-Aminophenol from Nitrobenzene by Catalytic Hydrogenation in Pressurized CO2/H2O System

Zhang, Tingting,Jiang, Jingyang,Wang, Yanhua

, p. 2050 - 2054 (2015)

The preparation of p-aminophenol from nitrobenzene by one-pot catalytic hydrogenation and in situ acid-catalyzed Bamberger rearrangement was first realized in a pressurized CO2/H2O system. By employing Pt-Sn/Al2O3 as catalyst, nitrobenzene could be converted to p-aminophenol with selectivity as high as 85% when the reaction was carried out at 140°C under 5.5 MPa CO2 and 0.2 MPa H2. This new protocol is environmentally benign because it is fully rid of the use of mineral acid by the application of self-neutralizable carbonic acid.

Bassett,O'Leary

, p. 2945 (1932)

Nickel nanoparticle/carbon catalysts derived from a novel aqueous-synthesized metal-organic framework for nitroarene reduction

Martín-Jimeno, F. Julian,Martínez-Alonso, Amelia,Paredes, Juan I.,Suárez-García, Fabián,Tascón, Juan M. D.

, (2021)

Carbon-supported, non-noble metal-based catalysts derived from metal-organic frameworks (MOFs) are attractive alternatives to noble metal-based systems, but typical syntheses of the starting MOFs are not desirable from an environmental and practical perspective (e.g., they rely on non-innocuous organic solvents and long reaction times). Here, we report the preparation of a Ni-based MOF in aqueous medium, at moderate temperature (95 °C) and in a short reaction time (2 g?1 depending on the carbonization temperature applied to the MOF, as well as high Ni contents (between ~36 and 57 wt%). Notwithstanding the latter, the metal was homogeneously distributed throughout the carbon matrix in the hybrid and was quite resistant to extensive agglomeration and sintering, even at temperatures as high as 1000 °C. With increasing carbonization temperature, the Ni component was seen to go through different crystal phases, i.e., Ni3C phase → Ni hexagonal close-packed phase → Ni face-centered cubic phase. The results of the catalytic tests suggested the former and latter phases to be the most active towards the reduction of 4-NP, with catalytic activity values as high as 0.039 mol4-NP molNi?1 min?1.

Development of a Quasi-Steady Flow Electrochemical Paper-Based Analytical Device

Adkins, Jaclyn A.,Noviana, Eka,Henry, Charles S.

, p. 10639 - 10647 (2016)

An electrochemical paper-based analytical device (ePAD) was developed for quasi-steady flow detection at microwire electrodes, for the first time. The device implements a fan shaped geometry connected to an analysis channel whereby solution is pulled from an inlet, through a channel, and into the steadily increasing capillary network of the fan. The network counteracts the decrease in solution flow rate associated with increasing viscosity within the channel, generating quasi-steady flow within the analysis channel. Microwire electrodes were embedded between two paper layers within the analysis channel, such that solution flow occurred on both sides of the wire electrodes. The quasi-steady flow ePAD increased the current by 2.5 times and 0.7 times from a saturated channel with no flow and from a single-layer paper device with flow, respectively. Amperometric detection was used for flow injection analysis (FIA) of multiple analytes at both Au and Pt microwire working electrodes, both of which provided similar sensitivity (ca. 0.2 mM-1) when normalized to the same standard. The two-layer paper devices provided a detection limit of 31 μM for p-aminophenol (PAP) using Pt electrodes and was also used to detect enzyme activity for the reaction of β-galactosidase with p-aminophenyl-galactopyranoside (PAPG). Measured enzyme kinetics provided similar Vmax (0.079 mM/min) and Km (0.36 mM) values as those found in the literature. This device shows great promise toward use in enzyme-linked immunosorbent assays or other analytical techniques where flow or washing steps are necessary. The developed sensor provides a simple and inexpensive device capable of performing multiple injection analysis with steady-flow and online detection that would normally require an external pump to perform.

Magnetic rod-based metal-organic framework metal composite as multifunctional nanostirrer with adsorptive, peroxidase-like and catalytic properties

Meteku, Benjamin Edem,Huang, Jiankun,Zeng, Jingbin,Aslam, Sobia,Zhang, Yu,Zhang, Xue,Cui, Bingwen,Wen, Cong-ying,Yan, Zifeng

, p. 3245 - 3251 (2021)

Although magnetic stirring is frequently used to enhance the kinetics for adsorption, chemical and biochemical reactions, the introduction of stirrers inevitably leads to the adsorption of analytes and thus interferes with the efficiency of the chemical process or reaction. In this work, magnetic Fe3O4 nanorods with tunable length-to-diameter ratio were synthesized via a hydrothermal method and used as templates for the in-situ depositing of MIL-100(Fe) and gold nanoparticles. Such nanorod-based material can not only function as an adsorbent, nanozyme, and a heterogeneous catalyst for corresponding applications but also serve as a magnetic nanostirrer to enhance kinetics. As a proof-of-concept, the capture of bacteria pathogen, mimic-peroxidase-based colorimetric detection of hydrogen peroxide, and the catalytic reduction of selected organic pollutants were conducted using the as-synthesized Fe3O4@MIL-100(Fe)-Au nanostirrer with and without magnetic field. The results show that the rates of bacteria capture, mimetic enzyme reaction and catalysis were tremendously expedited. We believe this magnetic field-assisted approach holds great promise for future applications, because, not only does it eliminate the use of external magnetic stirrers and thereby decrease the risk of foreign pollution but also, is adaptable for nanoscale reaction systems where conventional stirring is not applicable due to size limitations.

KINETIC SUBSTITUENT AND ISOTOPE EFFECTS IN THE ACID-CATALYSED REARRANGEMENT OF N-PHENYLHYDROXYLAMINES. ARE NITRENIUM IONS INVOLVED?

Kohnstam, George,Petch, W. Andrew,Williams, D. Lyn H.

, p. 423 - 428 (1984)

Acidity-rate profiles have been established for the rearrangement of N-phenylhydroxylamine and its derivatives in aqueous sulphuric acid and also in D2SO4-D2O.The results, particularly the change in the magnitude of the kinetic solvent isotope effect on increasing the acidity, are consistent only with a reaction mechanism involving unimolecular decomposition of the O-protonated species.N-Ethyl substitution has only a very small effect on the overall rate of reaction, whereas the rate constant was increased by ca. 100 by 4-Me substitution.The substituent effects argue against the involvement of a nitrenium ion intermediate but rather suggest that the intermediate is better represented by an imine structure with the positive charge at the 4-position in the aromatic ring.

-

Matsumura,Sone

, p. 1406 (1931)

-

Aniline-Hydroxylase Activity of Myoglobin by Coupling with a Membrane-Bound Electron Transport System

Hamachi, Itaru,Fujita, Akio,Kunitake, Toyoki

, p. 657 - 658 (1995)

Aniline-hydroxylase activity of myoglobin (Mb) can be induced by a rationally assembled semi-artificial multienzyme system of NADH - FMN - Mb on a synthetic bilayer membrane.

Spectrophotometric determination of paracetamol with microwave assisted alkaline hydrolysis

Xu, Chunli,Li, Baoxin

, p. 1861 - 1864 (2004)

A novel and rapid spectrophotometric method for the determination of paracetamol is proposed in this paper. The proposed method is based on the microwave assisted alkaline hydrolysis of paracetamol to p-aminophenol that reacts with S2- in the presence of Fe3+ as oxidant to produce a methylene blue-like dye having an absorptivity maximum at 540nm. The experiment showed that paracetamol could be hydrolysed quantitatively to p-aminophenol in only 1.5min under radiation power 640W using a microwave in NaOH medium. The system obeys Beer's law in the range of 0-3.0×10 -4moll-1 paracetamol. The molar absorptivity and Sandell's sensitivity were found to be 3.2×103lmol-1cm -1 and 0.047μgcm-2, respectively. The relative standard deviation (n=11) was 1.7% for 8.0×10-5moll-1 paracetamol. The method has been applied successfully to analysis of paracetamol in pharmaceutical preparation.

Fe3O4 – Glutathione stabilized Ag nanoparticles: A new magnetically separable robust and facile catalyst for aqueous phase reduction of nitroarenes

Kumari, Mitlesh,Gupta, Ragini,Jain, Yachana

, (2019)

The heterostructured Ag nanoparticles decorated Fe3O4 Glutathione (Fe3O4-Glu-Ag) nanoparticles (NPs) were synthesized by sonicating glutathione (Glu) with magnetite and further surface immobilization of silver NPs on it. The ensuing magnetic nano catalyst is well characterized by Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), high resolution transmission electron microscopy (HRTEM), powder X-ray diffraction (PXRD), thermogravimetric analysis (TGA). The prepared Fe3O4-Glu-Ag nanoparticles have proved to be an efficient and recyclable nanocatalyst with low catalyst loading for the reduction of nitroarenes and heteronitroarenes to respective amines in the presence of NaBH4 using water as a green solvent which could be easily separated at the end of a reaction using an external magnet and can be recycled up to 5 runs without any significant loss in catalytic activity. Gram scale study for the reduction of 4-NP has also being carried out successfully and it has been observed that this method can serve as an efficient protocol for reduction of nitroarenes on industrial level.

Highly efficient Au/TiO2 catalyst for one-pot conversion of nitrobenzene to p-aminophenol in water media

Zou, Luyao,Cui, Yuanyuan,Dai, Weilin

, p. 257 - 262 (2014)

Au/TiO2 catalyst is firstly reported to be efficient in the hydrogenation of nitrobenzene to produce p-aminophenol with a high PAP selectivity of 81% and overall yield more than 63%. The catalyst is also quite stable and can be reused for at least 4 times with only slight decrease in activity.

A hydroquinone based palladium catalyst for room temperature nitro reduction in water

Kumar, Alok,Purkait, Kallol,Dey, Suman Kr.,Sarkar, Amrita,Mukherjee, Arindam

, p. 35233 - 35237 (2014)

A hydroquinone based palladium complex [Pd(H2L)(Cl)2] (1), acts as an efficient room temperature catalyst for reduction of nitroarenes in water as solvent. 1 also acts as a tandem catalyst for Suzuki-Miyaura cross coupling in ethanol followed by reduction of nitroarenes in one pot with a loading of 0.25 mol% catalyst.

Carbonization of Co-BDC MOF results in magnetic C@Co nanoparticles that catalyze the reduction of methyl orange and 4-nitrophenol in water

Ahsan, Md. Ariful,Fernandez-Delgado, Olivia,Deemer, Eva,Wang, Huiyao,El-Gendy, Ahmed A.,Curry, Michael L.,Noveron, Juan C.

, (2019)

Herein we report a simple, facile and green technique for the preparation of magnetic cobalt nanoparticles (NPs) embedded on porous carbon (C@Co) nanocatalyst using MOFs template and explored for the catalytic reduction of Methyl orange (MO) and 4-Nitroph

Liquid phase hydrogenation of nitrobenzene to para-aminophenol over Pt/ZrO2 Catalyst and SO4 2-/ZrO 2-Al2O3 solid acid

Liu, Pingle,Hu, Yaohua,Ni, Min,You, Kuiyi,Luo, Hean

, p. 65 - 68 (2010)

ZrO2-Al2O3 binary oxide was prepared by homogeneous coprecipitation method. SO4 2-/ZrO2 and SO4 2-/ZrO2-Al2O3 were prepared by impregnation method and were characterized by BET, XRD and TPD. Pt/ZrO2 was prepared by incipient wetness impregnation of ZrO 2 with an aqueous solution of H2PtCl6. Subsequently, hydrogenation of nitrobenzene to para-aminophenol over Pt/ZrO 2 catalyst and SO4 2-/ZrO2-Al 2O3 solid acid using water as solvent was performed. The results indicate that para-aminophenol as well as a small quantity of aniline and ortho-aminophenol are obtained without using any environmentally undesirable liquid acid. The para-aminophenol selectivity reaches to 74.9% with 44.8% of nitrobenzene conversion under the optimal reaction conditions. And the amount of Al2O3 in SO4 2-/ZrO 2-Al2O3 has great influence on the selectivity to para-aminophenol. Graphical Abstract: Hydrogenation of nitrobenzene to para-aminophenol over Pt/ZrO2 catalyst andSO4 2-/ZrO 2-Al2O3 solid acid was developed. The results indicate that para-aminophenol as well as a small quantity of aniline and ortho-aminophenol are obtained without using any environmentally undesirable liquid acid. The para-aminophenol selectivity reaches to 74.9 with 44.8% of nitrobenzene conversion under the optimal reaction conditions. And the amount of Al2O3 in SO4 2-/ZrO 2-Al2O3 has great influence on the selectivity to para-aminophenol.[Figure not available: see fulltext.]

Ir/C and Brφnsted acid functionalized ionic liquids an efficient catalytic system for hydrogenation of nitrobenzene to: P -aminophenol

Wang, Hong,Jiang, Taotao,Ma, Lei,Wang, Hanbing,Xu, Xiaoliang,Lu, Chunshan,Li, Xiaonian

, p. 31663 - 31670 (2017)

In this study, we found that the phenylhydroxylamine intermediate could desorb more easily from an Ir surface than from a Pt surface, which is beneficial for inhibiting the over-hydrogenation of phenylhydroxylamine to aniline. On the other hand, the Brφnsted acid functionalized ionic liquids with sulfonic acid and bisulfate anions were acidic enough to catalyze the Bamberger rearrangement to form p-aminophenol from phenylhydroxylamine. On this basis, a new catalytic system constructed by Ir/C and Brφnsted acid functionalized ionic liquid was applied, for the first time, to the one-pot hydrogenation of nitrobenzene to p-aminophenol. Our results indicate that the PAP selectivity of Ir/C and [SO3H-bmim][HSO4] Brφnsted functionalized ionic liquid was far more than that of the traditional Pt/C and sulfuric acid catalyst system. Furthermore, the dually functionalized ionic liquid ([HSO3-b-N-Bu3][HSO4]) can be used simultaneously as an acid catalyst and also as a surfactant, due to its higher lipophilicity. Therefore, our new catalytic system has unique advantages in the hydrogenation of nitrobenzene to p-aminophenol.

High catalytic efficiency of nanostructured β-CoMoO4 in the reduction of the ortho-, meta- and para-nitrophenol isomers

Al-Wadaani, Fahd,Omer, Ahmed,Abboudi, Mostafa,Hassani, Hicham Oudghiri,Rakass, Souad,Messali, Mouslim,Benaissa, Mohammed

, (2018)

Nanostructured -CoMoO4 catalysts have been prepared via the thermal decomposition of an oxalate precursor. The catalyst was characterized by infrared spectroscopy (FTIR), X-ray diffraction (XRD), Brunauer-Emmett-Teller method (BET), energy dispersive X-ray spectroscopy (EDX), and transmission electron microscopy (TEM). The efficiency of these nanoparticles in the reduction of ortho- and meta-nitrophenol isomers (2-NP, 3-NP, and 4-NP) to their corresponding aminophenols was tested using UV-visible spectroscopy measurements. It was found that, with a -CoMoO4 catalyst, NaBH4 reduces 3-NP instantaneously, whilst the reduction of 2-NP and 4-NP is slower at 8 min. This difference is thought to arise from the lower acidity of 3-NP, where the negative charge of the phenolate could not be delocalized onto the oxygen atoms of the meta-nitro group.

Adsorption driven formate reforming into hydride and tandem hydrogenation of nitrophenol to amine over PdO: Xcatalysts

Zhu, Xiaohui,Liang, Shipan,Chen, Shuang,Liu, Xiangdong,Li, Renhong

, p. 8332 - 8338 (2020)

Due to their high toxicity and non-biodegradability, efficient reduction of nitroarenes to amines is of great practical importance, yet it still remains a significant challenge. Herein, we report PdO/PdO2 nanoparticles uniformly supported on titanate nanotubes (PdOx/TiNTs) for catalyzing the tandem dehydrogenation of sodium formate (SF) and hydrogenation of p-nitrophenol (PNP) to p-aminophenol (PAmP) under mild conditions. Notably, SF adsorption is mainly driven by the hydrogen bonding interactions between the H atom in SF and surface Pd sites, which factually makes the interface of PdOx/TiNT-SF an effective platform for C-H activation. Meanwhile, it is also found that the efficiency of the hydrogenation reaction depends on the reduction rate of the nitro group to nitroso group, and the O atoms adjacent to Pd are considered as the essential sites that facilitate this process. On the basis of the above two effects, the PdOx/TiNT catalyst shows unprecedented catalytic activity (turnover frequency, TOF, is 45.6 h-1) and good selectivity (~100%) during PNP reduction at room temperature. This work deepens our understanding on tandem catalytic (de)hydrogenation systems, and will benefit the design of heterogeneous catalysts for the production of industrially important chemicals.

Hydrogenation of nitrobenzene to 4-aminophenol over supported platinum catalysts

Tanielyan, Setrak K.,Nair, Jayesh J.,Marin, Norman,Alvez, Gabriela,McNair, Robert J.,Wang, Dingjun,Augustine, Robert L.

, p. 681 - 688 (2007)

The conversion of nitrobenzene (NB) to p-aminophenol (PAP) takes place by way of an initial partial hydrogenation to produce phenylhydroxyl amine (PHA) which then undergoes an in situ acid-catalyzed rearrangement to PAP. This reaction is most commonly run using Pt/C catalysts in the presence of aqueous sulfuric acid and a surfactant to assist in dispersing the NB throughout the reaction medium. The yield of PAP is closely related to those reaction parameters which facilitate first the partial hydrogenation step and second the acid-promoted rearrangement before further hydrogenation to aniline can take place. The effect which a number of reaction parameters such as hydrogen pressure, reaction temperature, stirring rate, and the amounts of NB, the catalyst, and the surfactant present in the reaction mixture had on the rate and selectivity of the hydrogenation was examined. Optimization of these parameters led to the formation of PAP at a selectivity (PAP/AN) of 5.4 with a productivity of over 80,000 g PAP/g Pt/h.

Kinetic rotating droplet electrochemistry: A simple and versatile method for reaction progress kinetic analysis in microliter volumes

Challier, Lylian,Miranda-Castro, Rebeca,Marchal, Damien,Noel, Vincent,Mavre, Francois,Limoges, Benoiit

, p. 14215 - 14228 (2013)

Here, we demonstrate a new generic, affordable, simple, versatile, sensitive, and easy-to-implement electrochemical kinetic method for monitoring, in real time, the progress of a chemical or biological reaction in a microdrop of a few tens of microliters, with a kinetic time resolution of ca. 1 s. The methodology is based on a fast injection and mixing of a reactant solution (1-10 μL) in a reaction droplet (15-50 μL) rapidly rotated over the surface of a nonmoving working electrode and on the recording of the ensuing transient faradaic current associated with the transformation of one of the components. Rapid rotation of the droplet was ensured mechanically by a rotating rod brought in contact atop the droplet. This simple setup makes it possible to mix reactants efficiently and rotate the droplet at a high spin rate, hence generating a well-defined hydrodynamic steady-state convection layer at the underlying stationary electrode. The features afforded by this new kinetic method were investigated for three different reaction schemes: (i) the chemical oxidative deprotection of a boronic ester by H2O2, (ii) a biomolecular binding recognition between a small target and an aptamer, and (iii) the inhibition of the redox-mediated catalytic cycle of horseradish peroxidase (HRP) by its substrate H2O2. For the small target/aptamer binding reaction, the kinetic and thermodynamic parameters were recovered from rational analysis of the kinetic plots, whereas for the HRP catalytic/inhibition reaction, the experimental amperometric kinetic plots were reproduced from numerical simulations. From the best fits of simulations to the experimental data, the kinetics rate constants primarily associated with the inactivation/reactivation pathways of the enzyme were retrieved. The ability to perform kinetics in microliter-size samples makes this methodology particularly attractive for reactions involving low-abundance or expensive reagents.

Catalytic reduction of 4-nitrophenol by means of nanostructured polymeric Schiff base complexes

Aghaei, Marjan,Dinari, Mohammad,Kianfar, Ali Hossein

, (2020)

Polymeric Schiff base ligands were synthesized using 2-hydroxybenzaldehyde (L2), 4-hydroxy-3-methoxybenzaldehyde (L4), and 5-aminoisophthalic acid. The nanostructured complexes were then synthesized using Ni2+, Cu2+, and Mn3+. The ligands and complexes thus synthesized were characterized using Fourier-transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis (TGA), and field-emission scanning electron microscopy. The thermal stability of the complexes was confirmed using TGA. The synthesized complexes were used as catalysts in the reduction of 4-nitrophenol (4-NP) to 4-aminophenol in an aqueous phase in the presence of sodium borohydride. In this work, the catalytic reactivity of nanostructured complexes was compared using the rate constant (k) of the reaction. The reaction time for the reduction of 4-NP was 5–14 min for different complexes. The catalytic system based on Ni2+/2-hydroxybenzaldehyde was the most active and displayed reusability in the reduction of 4-NP.

Synthesis of glucose-mediated Ag-γ-Fe2O3 multifunctional nanocomposites in aqueous medium - a kinetic analysis of their catalytic activity for 4-nitrophenol reduction

Kaloti, Mandeep,Kumar, Anil,Navani, Naveen K.

, p. 4786 - 4799 (2015)

This paper reports the synthesis of γ-Fe2O3 supported Ag nanoparticles (NPs) in aqueous medium by following a green approach. The presence of Fe2O3 in the gamma phase and silver in the nanocomposite has been confirmed by Raman spectroscopy, EDAX and XPS analyses. The presence of Ag in the nanocomposite is also indicated by UV spectroscopy. In the process of in situ generation of glucose mediated Ag NPs on the γ-Fe2O3 matrix, the size of γ-Fe2O3 nanoclusters reduced from 11.6 ± 1.6 to 9 ± 1 nm as was estimated from HRTEM analysis. Glucose served as an effective stabilizer for both Ag and γ-Fe2O3 in the nanocomposite. At lower concentrations of Ag (0.15-1.2 μM) the reduction of 4-nitrophenol (4-Nip) follows pseudo-first-order kinetics and the second order rate constant for this process was found to be 5.28 × 103 dm3 mol-1 s-1. Whereas, at higher concentrations (3.2-28.9 μM), it follows zero-order kinetics and occurred with a rate constant of 1 × 10-2 mol dm-3 s-1. The amount of silver in the nanocomposite is found to influence the kinetics of the catalytic reduction in a complex scheme following the Langmuir-Hinshelwood mechanism. The recyclability of the as-synthesized nanocomposite up to 7 cycles and the catalytic effect even at a very low silver concentration (0.15 μM) associated with high surface area and superparamagnetism suggest it to be a cost effective and environmentally friendly potential catalytic system.

An enzyme-copper nanoparticle hybrid catalyst prepared from disassembly of an enzyme-inorganic nanocrystal three-dimensional nanostructure

Li, Zhixian,Ding, Yi,Wu, Xiaoling,Ge, Jun,Ouyang, Pingkai,Liu, Zheng

, p. 20772 - 20776 (2016)

Enzyme-copper phosphate composites with highly porous three-dimentional (3D) structures were first prepared by self-assembly of protein molecules with copper ions in phosphate buffer solution. The self-assembled enzyme-copper phosphate 3D nanostructures w

Magnetic Fe3O4/graphene oxide/copper-based nanocomposite as a reusable catalyst for the reduction of 4-nitrophenol

Zabihzadeh, Mehdi,Shirini, Farhad,Tajik, Hassan,Shokri, Zahra,Karami, Shiva

, p. 121 - 127 (2020)

In the present investigation, Fe3O4/Graphene oxide/Pr–NH2–CuII was reported as a novel magnetically recoverable nanocomposite and characterized using various analytical techniques such as FT-IR spectroscopy, field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray spectroscopy (EDX), vibrating sample magnetometry (VSM), X-ray diffraction (XRD), and inductively coupled plasma (ICP). The catalytic performance of the synthesized catalyst was evaluated in the reduction of 4-nitrophenol to 4-aminophenol by an excess amount of sodium borohydride as the source of hydrogen in aqueous solution. The reaction was monitored by UV-vis spectroscopy at ambient temperature. Magnetic nature of the catalyst led to its simple recovery by a permanent magnet and excellent recyclability without appreciable loss of the catalytic activity.

Interaction of tetrachloroethylene with rat hepatic microsomal P450-dependent monooxygenases

Hanioka,Jinno,Takahashi,Nakano,Yoda,Nishimura,Ando

, p. 151 - 165 (1995)

1. We have studied the effects of tetrachloroethylene (PCE) on the kinetics of the P450-dependent monooxygenases in rat liver microsomes. 2. 7-Pentoxyresorufin O-depentylase (PROD) and 7-benzyloxyresorufin O-debenzylase (BROD) activities in phenobarbital (PB)-treated rat liver microsomes were substantially inhibited by PCE. The inhibition profiles were non-competitive for both enzyme activities; K(i)'s from Eadie-Hofsee plots were 0.16 and 0.29 mM for PROD and BROD respectively. In contrast, the enzyme activities in untreated, β-naphthoflavone (BNF)-, isoniazid (ISN)- and pregnenolone-16α-carbonitrile (PCN)-induced microsomes were not affected by PCE. 3. 7-Ethoxycoumarin O-deethylase (ECOD) activity in PB-induced microsomes was competitively inhibited by PCE, with a K(i) that was lower than those of other microsomes. 4. PCE inhibited 7-ethoxyresorufin O-deethylase (EROD) activities in some microsomes slightly. The K(i) for PCE was the lowest in untreated, followed by ISN-treated microsomes. 5. No effect of PCE upon aniline 4-hydroxylase (AN4H) and testosterone 6β-hydroxylase (TS6BH) activities was evident in any microsomal preparation. 6. These results indicate that PCE inhibits PB-inducible, P450-dependent monooxygenases in vitro non-competitively or competitively, and that the P450 enzymes of the P4502B subfamily may contribute to PCE toxicity.

Gold-Catalyzed Dearomative Spirocyclization of N-Aryl Alkynamides for the Synthesis of Spirolactams

Vacala, Taylor L.,Carlson, Paul R.,Arreola-Hester, Asa,Williams, Chloé G.,Makhoul, Evana W.,Vadola, Paul A.

, p. 1493 - 1501 (2018)

A catalytic redox-neutral method for the synthesis of spirolactams proceeding through the dearomative spirocyclization of N-aryl alkynamides is reported. In contrast to stoichiometric activating agents employed for related transformations, we show that the use of 5 mol % of Au(PPh3)Cl and AgOTf in dichloroethane at 50-80 °C leads to selective spirocyclization, furnishing the products in yields of 35-87%. The substrate scope of the reaction is good, with both electron-donating and electron-withdrawing groups being tolerated around the arene ring, as well as substitution at the amide nitrogen. The identity of the para-alkoxy group on the arene ring is key to achieving selectivity for spirocyclization over alternative mechanistic pathways. While the presence of a para-methoxy group leads to trace amounts of the desired spirolactams, the para-tert-butoxy or para-hydroxy substrate analogues furnish the spirolactams in good yield with high selectivity.

Au(iii)-promoted polyaniline gold nanospheres with electrocatalytic recycling of self-produced reactants for signal amplification

Cui, Yuling,Chen, Huafeng,Tang, Dianping,Yang, Huanghao,Chen, Guonan

, p. 10307 - 10309,3 (2012)

A novel and redox-active nanocatalyst, Au(iii)-promoted polyaniline gold nanosphere (GPANG), was designed as the nanolabel for highly efficient electrochemical immunoassay of human IgG by coupling with electrocatalytic recycling of self-produced reactants.

Preparation of bimetallic metal-organic framework microflowers by spray method

Zhang, Liying,Li, Linlin,Bai, Xiaojue,Xia, Mingjian,Shao, Lei,Wang, Tieqiang,Zhang, Xuemin,Li, Yunong,Qi, Xuan,Fu, Yu

, p. 175 - 177 (2019)

The NiCo-MOF microflowers are fabricated by a rapid spray method, which are assembled by 2D NiCo-MOF nanosheets with uniform crystal morphology and homogeneous dispersion of Ni and Co. Because of their large exposed active sites and nanoscale thickness, the NiCo-MOF microflowers exhibit good catalytic performance for the reduction of 4-nitrophenol.

Hydroxylation of aromatic amines with dioxygen in photooxidation sensitized by substituted phthalocyanines

Fedorova, Tatyana M.,Derkacheva, Valentina M.,Shevchenko, Ekaterina N.,Luk'yanets, Evgeny A.,Bordaev, Eduard B.,Kaliya, Oleg L.

, p. 64 - 66 (2020)

Photooxidation of aniline and its methyl and chloro derivatives with dioxygen sensitized by substituted zinc (PcZn) and palladium (PcPd) phthalocyanines in solution and on the carrier surface upon visible light irradiation affords selectively the corresponding p-aminophenols. Active and the most stable PcPd derivative adsorbed on Amberlite XAD 7HP provides conversion of 2,6-dimethylaniline with selectivity over 90% without the loss of sensitizer activity at least in 8 repeated cycles, the overall turnover number of the sensitizer being greater than 25,000.

Transfer Hydrogenation of Nitroarenes Catalyzed by CoCu Anchored on Nitrogen-doped Porous Carbon

Liu, Xiaotong,Zhang, Longkang,Wang, Junmin,Shang, Ningzhao,Gao, Shutao,Wang, Chun,Gao, Yongjun

, (2020)

The non-precious metal catalysts with high catalytic activity is extremely desirable but still full of challenges. In this paper, CoCu bimetal immobilized on nitrogen-doped porous carbon (CoCu-N-C) was prepared by an effective ligand-stabilized pyrolysis strategy. CoCu-N-C exhibited excellent catalytic efficiency for the transfer hydrogenation of nitroarenes with ammonia borane as hydrogen source, which can be ascribed to the well dispersed metal nanoparticles, the synergetic interaction of CoCu bimetal and nitrogen-doped carbon. The durability and recyclability experiments of the recycled CoCu-N-C catalyst indicated that no obvious change in catalytic performance was observed after five consecutive cycles. To gain insight into the catalytic mechanism of CoCu-N-C for the hydrogenation reaction, density functional theory calculations was also conducted. This work provides an universal approach for constructing highly efficient non-precious metal heterogeneous catalysts and which may find diverse high performance applications.

Wavelength-dependent photochemistry of acetaminophen in aqueous solutions

Pozdnyakov, Ivan P.,Zhang, Xu,Maksimova, Tatiana A.,Yanshole, Vadim V.,Wu, Feng,Grivin, Vjacheslav P.,Plyusnin, Victor F.

, p. 117 - 123 (2014)

The influence of irradiation wavelength and intensity on photochemistry of acetaminophen (APAP) in aqueous solution was investigated by combination of steady-state and laser flash photolysis as well as HPLC and LC-MS. Steady-state irradiation at 254 nm leads to APAP disappearance with the quantum yield 0.0014 and to formation of 1-(2-amino-5-hydroxyphenyl)ethanone (P1) as a main primary photo-Fries product. In opposite the laser excitation at 266 nm leads predominantly to two-photon ionization of APAP with the quantum yield 0.013 (I = 70 mJ/cm2) and to the formation of one main product of phenoxyl radical reactions - N-(3,4-dihydroxyphenyl)acetamide (P5). Steady-state excitation at 282 nm leads to both P1 and P5 products formation indicating competition of photo-Fries and photoionization processes. The wavelength-dependent mechanism of APAP photolysis is proposed and discussed.

Flavhemoglobin: A Semisyntheic Hydroxylase Acting in the Absence of Reductase

Kokubo, Toshio,Sassa, Shigeru,Kaiser, E. T.

, p. 606 - 607 (1987)

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Fabrication of thermally stable and active bimetallic Au-Ag nanoparticles stabilized on inner wall of mesoporous silica shell

Chen, Yu,Wang, Qihua,Wang, Tingmei

, p. 13940 - 13947 (2013)

A general method has been developed for the fabrication of highly dispersed and thermally stable bimetallic Au-Ag nanoparticles (NPs) stabilized on the inner wall of a mesoporous silica shell. In our approach, gold particles were formed in the first step on carbon spheres decorated with Sn2+ cations. Upon Ag+ adsorption and reduction by l-ascorbic acid in the second step, specific nanoparticles with a gold-silver alloy core and a silver nanoshell have been formed. Important evidence of the core-shell configurations of the bimetallic Au-Ag nanoparticles were clearly characterized by UV-vis, TEM and HAADF-STEM observations combined with elemental mapping and line scans. The mesoporous silica outer shell was obtained through the hydrolysis and condensation of the precursors tetraethoxysilane (TEOS) in a basic condition and cetyltrimethylammonium bromide (CTAB) as a structure-directing agent. On this basis, the nanoreactors were fabricated after calcination, which further serves as a nanoreactor for the reduction of p-nitrophenol. Furthermore, such particles have been found to be thermally stable and their sizes remain substantially unchanged even upon calcination in air at 500 °C and a reduction treatment in H2. Potentially, the method can be developed into a general approach to synthesize other highly dispersed and thermally stable bimetallic nanoparticles stabilized on the inner wall of a mesoporous silica shell.

Synthesis of p-aminophenol by catalytic hydrogenation of nitrobenzene

Rode,Vaidya,Chaudhari

, p. 465 - 470 (1999)

The present work describes the preparation of p-aminophenol via single-step catalytic hydrogenation of nitrobenzene in acid medium. A conventional method of synthesis of p-aminophenol is a two-step reaction involving iron-acid reduction of p-nitrophenol. This method causes serious effluent disposal problems due to the stoichiometric use of iron-acid, which leads to the formation of Fe-FeO sludge (?2 kg/kg of product) in the process, which cannot be recycled. The single-step hydrogenation of nitrobenzene was carried out using platinum catalyst, and the process conditions were optimized. Complete conversion of nitrobenzene was achieved with selectivity to p-aminophenol as high as 75% under the best set of conditions. Furthermore, the catalyst can be easily recovered and efficiently recycled giving the TON as high as 1.38 κ' 10.5 This paper presents studies on the effect of various process parameters such as temperature, hydrogen pressure, and substrate and acid concentration on the rate of reaction and selectivity to p-aminophenol.

Gold nanoparticles stabilized by amphiphilic hyperbranched polymers for catalytic reduction of 4-nitrophenol

Dai, Yu,Yu, Peng,Zhang, Xiaojin,Zhuo, Renxi

, p. 65 - 71 (2016)

Amphiphilic hyperbranched polymers (Hx-PEI-PEG) with polyethylene glycol (PEG) chains and low-molecular-weight polyethylenimine (PEI) conjugated to commercial aliphatic hyperbranched polyesters (Boltorn Hx) were used to stabilize gold nanoparticles (AuNPs) at the interlayer between the core and the shell. It was found that low generations of Hx-PEI-PEG such as H20-PEI-PEG and H30-PEI-PEG cannot effectively stabilize AuNPs. However, H40-PEI-PEG was both the reduction agent and the stabilizer for the formation of AuNPs, which was confirmed from the solution color change and UV-vis absorption spectra. Spherical nanosized AuNPs (below 10 nm) with narrow particle size distributions were observed from the TEM images. The H40-PEI-PEG-stabilized AuNPs solution could be shelf-stored at room temperature for more than 1 month. In addition, H40-PEI-PEG-stabilized AuNPs showed high catalytic activity for the reduction of 4-nitrophenol (4-NP) to 4-aminophenol (4-AP).

Contrasting effect of isoflurane on drug metabolism: Decreased type I and increased type II substrate metabolism in guinea pig liver microsomes

Mustafizur Rahman,Fujii, Kohyu,Kawamoto, Masashi,Yuge, Osafumi

, p. 331 - 337 (1996)

Inhalation anaesthetics might affect perioperative drug elimination by altering drug distribution, hepatic blood flow or drug metabolism. The in vitro effects of isoflurane on aniline hydroxylation and aminopyrine N-demethylation were investigated with guinea pig liver microsomes to assess the role of isoflurane on oxidative drug metabolism through the hepatic mixed-function oxidase system, p-Aminophenol and formaldehyde were measured spectrophotometrically as metabolic products of aniline hydroxylation and aminopyrine N-demethylation, respectively, where the reaction mixture consisted of a microsomal suspension, NADPH, aminopyrine or aniline, with or without isoflurane. The rate of cytochrome P-450 reduction by NADPH affected in the presence of isoflurane was investigated by spectrometric measurement of the CO-cytochrome P-450 complex formation at various times. Due to the addition of isoflurane, the V(max) values for aniline hydroxylation evidently increased except in high isoflurane concentration (3.33 mM) and for aminopyrine N-demethylation the value was significantly low only in the presence of a high isoflurane concentration, whereas the K(m) values significantly decreased in aniline hydroxylation and increased in aminopyrine N-demethylation, and isoflurane also accelerated the rate of cytochrome P-450 reduction by NADPH. These results reflect the inhibition of aminopyrine N-demethylation and activation of aniline hydroxylation in the presence of isoflurane as a consequence of isoflurane-accelerated cytochrome P-450 reduction by NADPH and/or drug-enzyme binding properties, and may have implications on the metabolism of perioperatively administered drugs during isoflurane anaesthesia.

Platinum N-heterocyclic carbene nanoparticles as new and effective catalysts for the selective hydrogenation of nitroaromatics

Lara, Patricia,Suarez, Andres,Colliere, Vincent,Philippot, Karine,Chaudret, Bruno

, p. 87 - 90 (2014)

In this communication, we report the first synthesis of Pt NPs stabilized with NHC ligands and their investigation as catalysts in the chemoselective hydrogenation of nitroarenes. The results in catalysis show that by a proper choice of the NHC stabilizer and the adjustment of the NHC/metal ratio, these NHC-capped Pt NPs exhibit high levels of activity and selectivity in the hydrogenation reactions. In particular, Pt NPs stabilized with 2 equiv. of IPr carbene (PtIPr0.2) catalyze the chemoselective reduction of a series of functionalized nitroarenes under mild conditions (1 bar H2, 30 °C). This catalyst tolerates the presence of a range of functional groups including hydroxyl, benzyloxy, carbonyl and olefinic moeities as well as halogens. Copyright

Designed Meso-macroporous Silica Framework Impregnated with Copper Oxide Nanoparticles for Enhanced Catalytic Performance

Kanwar, Rohini,Bhar, Rekha,Mehta, Surinder Kumar

, p. 2087 - 2095 (2018)

The template efficacy of solid lipid nanoparticles for generating porous silica materials with the amalgamation of Cu-functionalized cetylpyridinium chloride (CPC; as a co-emulsifier and as a metal source for generation of CuO oxide nanoparticles) has bee

A Simple but Efficient Catalytic Approach for the Degradation of Pollutants in Aqueous Media through Cicer arietinum Supported Ni Nanoparticles

Khan, Shahid Ali,Rasool, Shagufta,Rahman, Khaliq Ur,Hussain, Shah,Khan, Inamullah,Ismail, Muhammad,Farooq, Aliya,Khan, Sarzamin,Raza, Mian Ahmad,Asiri, Abdullah Muhammad,Khan, Sher Bahadar

, p. 1789 - 1802 (2020)

Plant based materials are considered to have broad applications in the remediation of toxic materials. In this report, we present an environmental friendly and economic Cicer arietinum, named as (CP) supported for the synthesis of Ni nanoparticles (NPs) designated as Ni@CP. The in situ Ni@CP NPs were obtained using aqueous medium in the presence of sodium borohydride (NaBH4) as a reducing agent. The prepared catalysts were applied for the hydrogenation/degradation of p-nitrophenol (PNP), o-nitrophenol (ONP), and 2,4-dinitrophenol (DNP), as well as congo red (CR), methyl orange (MO), methylene blue (MB) and rhodamine B (RB) dyes. The amount of total metal ions adsorbed onto the CP was evaluated by flame atomic absorption spectroscopy. The Ni@CP catalyst was characterized through PXRD, FTIR, FESEM and EDX analyses.

Catalytically Active Bimetallic Nanoparticles Supported on Porous Carbon Capsules Derived from Metal-Organic Framework Composites

Yang, Hui,Bradley, Siobhan J.,Chan, Andrew,Waterhouse, Geoffrey I. N.,Nann, Thomas,Kruger, Paul E.,Telfer, Shane G.

, p. 11872 - 11881 (2016)

We report a new methodology for producing monometallic or bimetallic nanoparticles confined within hollow nitrogen-doped porous carbon capsules. The capsules are derived from metal-organic framework (MOF) crystals that are coated with a shell of a secondary material comprising either a metal-tannic acid coordination polymer or a resorcinol-formaldehyde polymer. Platinum nanoparticles are optionally sandwiched between the MOF core and the shell. Pyrolysis of the MOF-shell composites produces hollow capsules of porous nitrogen-doped carbon that bear either monometallic (Pt, Co, and Ni) or alloyed (PtCo and PtNi) metal nanoparticles. The Co and Ni components of the bimetallic nanoparticles are derived from the shell surrounding the MOF crystals. The hollow capsules prevent sintering and detachment of the nanoparticles, and their porous walls allow for efficient mass transport. Alloyed PtCo nanoparticles embedded in the capsule walls are highly active, selective, and recyclable catalysts for the hydrogenation of nitroarenes to anilines.

Characterization of aniline hydroxylation by a cytochrome P-450 model and a possible hydroxylation mechanism.

Sakurai

, p. 3437 - 3439 (1980)

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High amplification rates from the association of two enzymes confined within a nanometric layer immobilized on an electrode: Modeling and illustrating example

Limoges, Benoit,Marchal, Damien,Mavre, Francois,Saveant, Jean-Michel

, p. 6014 - 6015 (2006)

Electrochemical responses (e.g., chronoamperometric) obtained with an immobilized enzyme that produces an electroactive species may be used to quantitate the amount of enzyme or the concentration of its substrate. It is shown, on theoretical and experimental bases, that product-to-substrate coupling with a second enzyme co-immobilized with the first within one or within a small number of monolayers, allows high amplification rates (higher than 1000), avoids membrane transport limitations, and lends itself to precise kinetic analyses that provide guidelines for optimization of the analytical sensitivity. Very large amplification factors, as large as several thousands, can be reached experimentally, in agreement with appropriately derived theoretical predictions, thus opening the route to the rational design of high-performance substrate sensing or affinity assays applications. Copyright

Simultaneous Voltammetric Determination of Acetaminophen and Isoniazid (Hepatotoxicity-Related Drugs) Utilizing Bismuth Oxide Nanorod Modified Screen-Printed Electrochemical Sensing Platforms

Mahmoud, Bahaa G.,Khairy, Mohamed,Rashwan, Farouk A.,Banks, Craig E.

, p. 2170 - 2178 (2017)

To overcome the recent outbreaks of hepatotoxicity-related drugs, a new analytical tool for the continuously determination of these drugs in human fluids is required. Electrochemical-based analytical methods offer an effective, rapid, and simple tool for on-site determination of various organic and inorganic species. However, the design of a sensitive, selective, stable, and reproducible sensor is still a major challenge. In the present manuscript, a facile, one-pot hydrothermal synthesis of bismuth oxide (Bi2O2.33) nanostructures (nanorods) was developed. These BiO nanorods were cast onto mass disposable graphite screen-printed electrodes (BiO-SPEs), allowing the ultrasensitive determination of acetaminophen (APAP) in the presence of its common interference isoniazid (INH), which are both found in drug samples. The simultaneous electroanalytical sensing using BiO-SPEs exhibited strong electrocatalytic activity toward the sensing of APAP and INH with an enhanced analytical signal (voltammetric peak) over that achievable at unmodified (bare) SPEs. The electroanalytical sensing of APAP and INH are possible with accessible linear ranges from 0.5 to 1250 μM and 5 to 1760 μM with limits of detection (3σ) of 30 nM and 1.85 μM, respectively. The stability, reproducibility, and repeatability of BiO-SPE were also investigated. The BiO-SPEs were evaluated toward the sensing of APAP and INH in human serum, urine, saliva, and tablet samples. The results presented in this paper demonstrate that BiO-SPEs sensing platforms provide a potential candidate for the accurate determination of APAP and INH within human fluids and pharmaceutical formulations.

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter

supporting information, p. 133 - 146 (2021/11/04)

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Polar hydrogen species mediated nitroarenes selective reduction to anilines over an [FeMo]Sx catalyst

Huang, Zhipeng,Li, Siqi,Liu, Huifang,Liu, Meijiang,Wang, Feng,Zhang, Chaofeng

, p. 1553 - 1560 (2022/02/03)

We herein present an efficient approach for the chemoselective synthesis of arylamines from nitroarenes and hydrazine over an iron-molybdenum sulfide catalyst ([FeMo]Sx). The heterogeneous hydrogen transfer reduction can be efficiently carried out at 30 °C and provides anilines with 95–99% selectivities. The in situ gas product analysis demonstrates that [FeMo]Sx can catalyze the decomposition of N2H4 to H* species, not H2. Combining with the kinetic analysis of the aniline generation rates from nitrobenzene and intermediates, the nitro group reduction to the nitroso group is confirmed to be the rate-determining step. The positive slope of Hammett's equation suggests that the critical intermediate in the rate-determining step is in the negative state, which suggests that the active H* should be in polar states (Hδ? and Hδ+). These findings will provide a novel route for the synthesis of substituted anilines and broaden the application of MoSx catalysts under mild conditions.

Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation

Wang, Erfei,Chen, Kaixuan,Chen, Yinan,Zhang, Jiawei,Lin, Xinrong,Chen, Mao

, p. 17 - 21 (2020/11/04)

A porous polymeric ligand (PPL) has been synthesized and complexed with copper to generate a heterogeneous catalyst (Cu@PPL) that has facilitated the efficient C-N coupling with various (hetero)aryl chlorides under mild conditions of visible-light irradiation at 80 °C (58 examples, up to 99% yields). This method could be applied to both aqueous ammonia and substituted amines, and is compatible to a variety of functional groups and heterocycles, as well as allows tandem C-N couplings with conjunctive dihalides. Furthermore, the heterogeneous characteristic of Cu@PPL has enabled a straightforward catalyst separation in multiple times of recycling with negligible catalytic efficiency loss by simple filtration, affording reaction mixtures containing less than 1 ppm of Cu residue. [Figure not available: see fulltext.]

Surface Roughness Effects of Pd-loaded Magnetic Microspheres on Reduction Kinetics of Nitroaromatics

An, Seonghwi,Manivannan, Shanmugam,Viji, Mayavan,Shim, Min Suk,Hwang, Byeong Hee,Kim, Kyuwon

supporting information, p. 894 - 899 (2021/05/06)

Metal nanoparticles decoration on magnetically active semiconductor materials is a common strategy to improve the colloidal stability, catalyst harvesting, and reuse. In this study, a surfactant-free solvothermal method followed by a heat treatment to pre

Process route upstream and downstream products

Process route

p-nitrosophenol
104-91-6

p-nitrosophenol

4-amino-phenol
123-30-8

4-amino-phenol

hydroquinone
123-31-9,8027-02-9

hydroquinone

Conditions
Conditions Yield
With air; titanium(IV) oxide; In water; at 50 ℃; pH=5.8; Kinetics; UV-irradiation;
1-allyloxy-4-nitrobenzene
1568-66-7

1-allyloxy-4-nitrobenzene

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
Conditions Yield
With ammonium formate; palladium on activated charcoal; In methanol; for 0.5h; Heating;
70%
5%
benzyl 4-nitrophenyl ether
1145-76-2

benzyl 4-nitrophenyl ether

p-benzyloxyaniline
6373-46-2

p-benzyloxyaniline

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
Conditions Yield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate; In tetrahydrofuran; at 20 ℃; for 0.5h;
56%
14%
28%
methyl 2-(4-hydroxy-phenylazo)benzoate
1246999-27-8

methyl 2-(4-hydroxy-phenylazo)benzoate

4-amino-phenol
123-30-8

4-amino-phenol

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
Conditions Yield
With sodium dithionite; water; In dimethyl sulfoxide; at 20 ℃; pH=7.4; Concentration; Kinetics; phosphate buffer;
4-(4'-hydroxyphenylazo)nitrobenzene
1435-60-5,81944-71-0

4-(4'-hydroxyphenylazo)nitrobenzene

4-amino-phenol
123-30-8

4-amino-phenol

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

Conditions
Conditions Yield
With sodium dithionite; water; In dimethyl sulfoxide; at 20 ℃; pH=7.4; Kinetics; phosphate buffer;
methyl yellow
60-11-7

methyl yellow

4-amino-phenol
123-30-8

4-amino-phenol

<i>N</i>,<i>N</i>-dimethyl-aniline
121-69-7,77733-26-7

N,N-dimethyl-aniline

aniline
62-53-3

aniline

N,N-Dimethyl-4-nitroaniline
100-23-2

N,N-Dimethyl-4-nitroaniline

3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

recorcinol
108-46-3

recorcinol

Conditions
Conditions Yield
With ferrous(II) sulfate heptahydrate; sulfuric acid; water; dihydrogen peroxide; at 25 ℃; pH=1.8; Kinetics;
4-nitro-thiobenzoic acid S-benzyl ester
63823-56-3

4-nitro-thiobenzoic acid S-benzyl ester

4-amino-phenol
123-30-8

4-amino-phenol

phenylmethanethiol
100-53-8

phenylmethanethiol

Conditions
Conditions Yield
With sodium tetrahydroborate; In tetrahydrofuran; water; at 20 ℃; Green chemistry;
water
7732-18-5

water

4-benzyloxyaniline hydrochloride
51388-20-6

4-benzyloxyaniline hydrochloride

4-amino-phenol
123-30-8

4-amino-phenol

benzyl chloride
100-44-7

benzyl chloride

Conditions
Conditions Yield
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

[1,4]benzoquinone-mono-(<i>O</i>-benzyl oxime )
392248-88-3

[1,4]benzoquinone-mono-(O-benzyl oxime )

4-amino-phenol
123-30-8

4-amino-phenol

benzyl chloride
100-44-7

benzyl chloride

Conditions
Conditions Yield
C,N-diphenylnitrone
201024-81-9

C,N-diphenylnitrone

4-amino-phenol
123-30-8

4-amino-phenol

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield

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