- Lanthanum ion doped nano TiO2 encapsulated in zeozyme and impregnated in a polystyrene film as a photocatalyst for the degradation of diuron in an aquatic ecosystem
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The occurrence of chlorinated herbicide diuron in water bodies is considered serious pollution and a major health hazard to flora, fauna and mankind. In the present investigation, we studied the photocatalytic degradation of diuron in an aquatic ecosystem using lanthanum ion doped nano TiO2 (Lnp) encapsulated in NaY zeolite pores (1 : 10) and impregnated in polystyrene film (ZLT). The hydrophobic nature of the polystyrene support resulted in an efficient and highly recoverable heterogeneous system. Catalyst characterization was carried out by FT-IR, XRD, DRS-UV, fluorescence, BET, SEM-EDAX and XPS. BET results revealed the successful loading of lanthanum ion doped TiO2 (Lnp) inside the NaY zeolite pores via a decrease in surface area for the zeolite encapsulated Lnp (ZLnp) as compared to NaY zeolite alone. DRS UV supported the impregnation of ZLnp in the polystyrene films; the bathochromic shift (Δλ) was 4 nm and the hypochromic shift decreased in intensity 10 fold. The photocatalytic reaction was carried out at a concentration of 20 mg L-1 of diuron, with 0.01 M H2O2 and a catalytic amount of 500 mg L-1 ZLT under unstirred conditions. Degradation of diuron by ZLT reached 40% after 2 hours. Noteworthy features are the good results under optimized conditions and that the same film models were used successfully in the presence of zebra fish (Danio rerio). The present investigation also demonstrated successful re-use of the photocatalytic film six times without any appreciable loss in catalytic activity. From the abovementioned results, it was proven that ZLT is an efficient and ecofriendly catalyst.
- Saranya,Sathiyanarayanan,Maheswari
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p. 110970 - 110975
(2016)
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Read Online
- Kinetics of the chemical degradation of diuron.
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The influence of pH and buffer concentration on the chemical degradation of diuron in water has been analysed over a wide temperature range. The process irreversibly gives 3,4-dichloroaniline as the only product containing the phenyl ring. H+, OH- and phosphate buffer are efficient catalysts of the reaction. The rate constant first increases rapidly at low buffer concentrations and then gradually levels off at higher ones. At 40 degrees C and high phosphate concentration (>0.01 M), or in the extreme pH regions, the half-life is approximately 4 months and the activation energy is 127 +/- 2 kJmol(-1).
- Salvestrini, Stefano,Di Cerbo, Paola,Capasso, Sante
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Read Online
- Catalytic Hydrogenation of Urea Derivatives and Polyureas
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We present herein the catalytic hydrogenation of various urea derivatives to amines and methanol. The reaction is catalyzed by a ruthenium or an iridium Macho pincer complex and produces amine and methanol in very good to excellent yields. Moreover, we also expand this concept to demonstrate the first example of the hydrogenative depolymerization of polyureas to produce diamines and methanol in moderate yields.
- Kumar, Amit,Luk, James
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supporting information
p. 4546 - 4550
(2021/08/30)
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- Indirect reduction of CO2and recycling of polymers by manganese-catalyzed transfer hydrogenation of amides, carbamates, urea derivatives, and polyurethanes
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The reduction of polar bonds, in particular carbonyl groups, is of fundamental importance in organic chemistry and biology. Herein, we report a manganese pincer complex as a versatile catalyst for the transfer hydrogenation of amides, carbamates, urea derivatives, and even polyurethanes leading to the corresponding alcohols, amines, and methanol as products. Since these compound classes can be prepared using CO2as a C1 building block the reported reaction represents an approach to the indirect reduction of CO2. Notably, these are the first examples on the reduction of carbamates and urea derivatives as well as on the C-N bond cleavage in amides by transfer hydrogenation. The general applicability of this methodology is highlighted by the successful reduction of 12 urea derivatives, 26 carbamates and 11 amides. The corresponding amines, alcohols and methanol were obtained in good to excellent yields up to 97%. Furthermore, polyurethanes were successfully converted which represents a viable strategy towards a circular economy. Based on control experiments and the observed intermediates a feasible mechanism is proposed.
- Liu, Xin,Werner, Thomas
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p. 10590 - 10597
(2021/08/20)
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- Minimization of Back-Electron Transfer Enables the Elusive sp3 C?H Functionalization of Secondary Anilines
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Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N-Dialkyl-derivatives enable radical generation α to the N-atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back-electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence of an exogenous alkylamine. This approach synergistically aids aniline SET oxidation and then accelerates the following deprotonation. In this way, the generation of α-anilinoalkyl radicals is now possible and these species can be used in a general sense to achieve divergent sp3 C?H functionalization.
- Zhao, Huaibo,Leonori, Daniele
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supporting information
p. 7669 - 7674
(2021/03/08)
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- Highly efficient hydrogenation reduction of aromatic nitro compounds using MOF derivative Co-N/C catalyst
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The direct hydrogenation reduction of aromatic nitro compounds to aromatic amines with non-noble metals is an attractive area. Herein, the pyrolysis of Co(2-methylimidazole)2 metal-organic framework successfully produces a magnetic Co-N/C nanocomposite, which exhibits a porous structure with a high specific area and uniform Co nanoparticle distribution in nitrogen-doped graphite. In addition, the Co-N/C catalysts possess high cobalt content (23%) with highly active β-Co as the main existing form and high nitrogen content (3%). These interesting characteristics endow the Co-N/C nanocomposite with excellent catalytic activity for the hydrogenation reduction of nitro compounds under mild conditions. In addition, the obtained Co-N/C nanocomposites possess a broad substrate scope and good cycle stability for the reduction of halogen-substituted or carbonyl substituted phenyl nitrates. This journal is
- Dai, Yuyu,Li, Xiaoqing,Wang, Likai,Xu, Xiangsheng
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p. 22908 - 22914
(2021/12/24)
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- Synthesis of CoFe2O4@Pd/Activated carbon nanocomposite as a recoverable catalyst for the reduction of nitroarenes in water
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Efficient reduction of nitro compounds into amines is an important industrial transformation. So, it is a great deal to design new catalysts for efficient reduction of the nitro compounds especially in water. In this work, a new magnetic Pd/activated carbon nanocomposite (CoFe2O4@Pd/AC) was synthesized via metal-impregnation-pyrolysis method. The CoFe2O4@Pd/AC was fully characterized by FT-IR, PXRD, FESEM, TEM, VSM, EDX-mapping and BET techniques. The results showed that CoFe2O4@Pd/AC is a highly reactive and easily recoverable magnetic catalyst for the reduction of the nitro compounds by using NaBH4 in water. For instance, aniline was obtained in high yield (99%) after 75 ?min at 25 ?C by using just 6 ?mg of the catalyst. In addition, CoFe2O4@Pd/AC was recovered by a simple magnetic decantation and it exhibits stable activity and remains intact during the catalytic process with no significant loss in activity (8 cycles).
- Hamadi, Hosein,Kazeminezhad, Iraj,Mohammadian, Sara
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- Novel lipophilic analogues from 2,4-D and Propanil herbicides: Biological activity and kinetic studies
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This work describes the synthesis of new lipophilic amides and esters analogues of classical organochlorides herbicides by incorporation of long-chains from fatty acids and derivatives. The new fatty esters and amides were synthesized in 96–99percent and 80–89percent yields, respectively. In general, all compounds tested showed superior in vitro activity than commercial herbicides against growth L. sativa and A. cepa, in ranges 86–100percent of germinative inhibition. The target compounds showed, significantly more susceptible towards acid hydrolysis than 2,4-dichlorophenoxyacetic acid (2,4-D). The kinetic and NMR studies showed that the incorporation of lipophilic chains resulted in a decrease in half-life time of new herbicides compounds (1.5 h) than 2,4-D (3 h). These findings suggest the synthesis of new lipophilic herbicides as potential alternative to traditional formulations, by incorporation of long fatty alkyl chains in the molecular structure of 2,4-D, resulting in superior in vitro herbicidal activity, best degradation behavior and more hydrophobic derivatives.
- D'Oca, Caroline R. M.,D'Oca, Marcelo G. M.,Nachtigall, Fabiane M.,Orth, Elisa S.,Porciuncula, Larissa M.,Santos, Leonardo S.,Santos, Maria F. C.,Teixeira, Alex R.
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- Synthesis and characterization of go-chit-ni nanocomposite as a recoverable nanocatalyst for reducing nitroarenes in water
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In the present study, nickel nanoparticles (Ni-NPs) immobilized on graphene oxide-chitosan (GO-Chit-Ni) have been synthesized and characterized as a catalyst for reduction of nitroarenes in water. For this purpose, GO has been functionalized with chitosan (GO-Chit). Then, Ni-NPs were immobilized on the surface of GO-Chit using a simple method. The GO-Chi-Ni nanocomposites were characterized using Fourier Transforms Infrared Spectroscopy (FT-IR), Transmission Electron Microscopy (TEM), X-Ray Diffraction Measurements (XRD), and Atomic Adsorption Spectrometry (AAS). The GO-Chi-Ni nanoparticles demonstrated appropriate catalytic activity in reducing nitroarenes to aryl amines in the existence of sodium borohydride (NaBH4) aqueous solution as a hydrogen source at 80oC. This catalytic system applies environmentally benign water as a solvent that is cheap, easily accessible, non-toxic, non-volatile, non-flammable and thermally stable. This type of catalyst can be applied several times with no considerable change in its performance.
- Azadi, Roya,Sarvestani, Mosayeb
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p. 523 - 531
(2020/07/17)
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- Synthesis method of halogenated aniline
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The invention provides a synthesis method of halogenated aniline. The synthesis method comprises the following steps: taking a carbon-coated nickel nano composite material containing alkaline-earth metals as a catalyst, and catalyzing a hydrogenation reduction reaction of halogenated nitrobenzene in a hydrogen atmosphere, wherein the nano composite material contains a core-shell structure with a shell layer and an inner core, the shell layer is a graphitized carbon layer containing alkaline-earth metals and oxygen, and the inner core is nickel nano particles. According to the method, the nanocomposite material is used as a catalyst; a carbon material and the nickel nano particles generate a synergistic effect and a good catalytic effect, the alkaline-earth metals of the shell layer further synergistically improve the catalytic performance of the nano composite material, and the catalyst is used for hydrogenation reduction of halogenated nitrobenzene to synthesize halogenated aniline,has excellent activity, selectivity and safety, and can effectively solve the dehalogenation problem in the reaction process.
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Paragraph 0153-0155
(2020/08/09)
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- Synthesis method of halogenated aniline
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The invention provides a synthesis method of halogenated aniline. The synthesis method comprises the following steps: taking a carbon-coated nickel nano composite material containing alkali metals asa catalyst, and catalyzing a hydrogenation reduction reaction of halogenated nitrobenzene in a hydrogen atmosphere; wherein the nano composite material contains a core-shell structure with a shell layer and an inner core, the shell layer is a graphitized carbon layer containing alkali metals, nitrogen and oxygen, and the inner core is nickel nano particles. According to the method, the nano composite material is used as a catalyst; a carbon material and the nickel nano particles generate a synergistic effect and a good catalytic effect, the alkali metals of the shell layer further synergistically improve the catalytic performance of the nano composite material, and the catalyst is used for hydrogenation reduction of halogenated nitrobenzene to synthesize halogenated aniline, has excellentactivity, selectivity and safety, and can effectively solve the dehalogenation problem in the reaction process.
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Paragraph 0138-0140
(2020/08/09)
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- Synthesis method of halogenated aniline
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The invention provides a synthesis method of halogenated aniline. The synthesis method comprises the following steps: taking a carbon-coated nickel nano composite material containing alkaline-earth metals as a catalyst, and catalyzing a hydrogenation reduction reaction of halogenated nitrobenzene in a hydrogen atmosphere; wherein the nano composite material contains a core-shell structure with a shell layer and an inner core, the shell layer is a graphitized carbon layer containing alkaline-earth metals, nitrogen and oxygen, and the inner core is nickel nano particles. According to the method,the nano composite material is used as a catalyst; a carbon material and the nickel nano particles generate a synergistic effect and a good catalytic effect, the alkaline-earth metals of the shell layer further synergistically improve the catalytic performance of the nano composite material, and the catalyst is used for hydrogenation reduction of halogenated nitrobenzene to synthesize halogenatedaniline, has excellent activity, selectivity and safety, and can effectively solve the dehalogenation problem in the reaction process.
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Paragraph 0103; 0137-0139
(2020/08/09)
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- Ru-Catalyzed Deoxygenative Transfer Hydrogenation of Amides to Amines with Formic Acid/Triethylamine
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A ruthenium(II)-catalyzed deoxygenative transfer hydrogenation of amides to amines using HCO2H/NEt3 as the reducing agent is reported for the first time. The catalyst system consisting of [Ru(2-methylallyl)2(COD)], 1,1,1-tris(diphenylphosphinomethyl) ethane (triphos) and Bis(trifluoromethane sulfonimide) (HNTf2) performed well for deoxygenative reduction of various secondary and tertiary amides into the corresponding amines in high yields with excellent selectivities, and exhibits high tolerance toward functional groups including those that are reduction-sensitive. The choice of hydrogen source and acid co-catalyst is critical for catalysis. Mechanistic studies suggest that the reductive amination of the in situ generated alcohol and amine via borrowing hydrogen is the dominant pathway. (Figure presented.).
- Pan, Yixiao,Luo, Zhenli,Xu, Xin,Zhao, Haoqiang,Han, Jiahong,Xu, Lijin,Fan, Qinghua,Xiao, Jianliang
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supporting information
p. 3800 - 3806
(2019/07/12)
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- AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS
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In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.
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Paragraph 0257
(2018/03/25)
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- Development of a novel protocol for chemoselective deprotection of N/O-benzyloxycarbonyl (Cbz) at ambient temperature
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Abstract: A novel protocol for the deprotection of N-benzyloxycarbonyl and O-benzyloxycarbonyl groups by nickel boride generated in situ from NaBH4 and NiCl2·6H2O in methanol at room temperature has been developed to give the corresponding amines and phenols. This protocol is chemoselective as groups like chloro, bromo, amide, ester, pyridine, and tert-butyloxycarbonyl moiety are unaffected under these conditions. The deprotection has also been validated in gram scale reactions, to establish the wider appropriateness of this protocol. Graphical abstract: [Figure not available: see fulltext.].
- Saroha, Mohit,Aggarwal, Komal,Bartwal, Gaurav,Khurana, Jitender M.
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p. 2231 - 2235
(2018/10/02)
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- Silver nanoparticles supported on ionic-tagged magnetic hydroxyapatite as a highly efficient and reusable nanocatalyst for hydrogenation of nitroarenes in water
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A novel chemically modified magnetic hydroxyapatite (MHAp) was prepared and used as support and stabilizer for the synthesis of silver nanoparticles. First, 1,4-diazabicyclo[2.2.2]octane (DABCO) was successfully grafted onto the surface of MHAp, and then silver nanoparticles were homogeneously loaded on mesoporous MHAp-DABCO (ionic-tagged MHAp) nanocomposite by in situ chemical reduction of silver nitrate using sodium borohydride. The structure and properties of the resulting MHAp-DABCO-Ag nanocomposite were confirmed using various techniques. The catalytic activity of ionic-tagged MHAp-Ag nanocatalyst was investigated for the hydrogenation reaction of nitroarenes in aqueous media. The results reveal that the Ag-containing inorganic–organic nanocomposite is highly efficient for the reduction of a wide range of aromatic nitro compounds under green conditions. The superparamagnetic nature of the nanocatalyst leads to its being readily removed from solution via application of a magnetic field, and it can be easily stored and reused.
- Pashaei, Mokhtar,Mehdipour, Ebrahim
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- Silver Nanoparticles Engineered Β-Cyclodextrin/Γ-Fe2O3@ Hydroxyapatite Composite: Efficient, Green and Magnetically Retrievable Nanocatalyst for the Aqueous Reduction of Nitroarenes
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Abstract: Ag nanoparticles incorporated β-cyclodextrin conjugated magnetic hydroxyapatite, γ-Fe2O3@HAp-CD.Ag was conveniently synthesized via the grafting of β-cyclodextrin moieties on the hydroxyapatite surface, followed by reacting of the nanocomposite, γ-Fe2O3, with silver nitrate and then its reduction with sodium borohydride. The cavity of β-cyclodextrin units as host material can stabilize the Ag nanoparticles (particles size: 12–14 nm) effectively and prevent their aggregation and separation from the surface. The nanocomposite obtained appears to have an organized structure, with a magnetic γ-Fe2O3 core surrounded by a layer-structured coating shell. The structure and composition of the nanocomposite were confirmed by FT-IR, FE-SEM, TEM, TGA, XRD, EDS, BET, and VSM. This catalytic system selectively reduces the nitro group even in the presence of other sensitive functional groups in good to excellent yields (85–98%).The organometallic nanocatalyst was easily removed from solution using an external magnet and was successfully examined for five runs, with a slight loss of catalytic activity.
- Azaroon, Maedeh,Kiasat, Ali Reza
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p. 745 - 756
(2017/12/26)
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- Method for synthesizing 3,4-dichloroaniline by using micro-channel reactor
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The invention provides a method for synthesizing 3,4-dichloroaniline by using a micro-channel reactor. The micro-channel reactor is used for nitration and catalytic hydrogenation. The method comprisesthe following steps: nitration: preheating o-dichlorobenzene, mixing and preheating concentrated nitric acid and concentrated sulfuric acid, allowing the preheated materials to enter a reaction module group for a reaction and carrying out refining so as to obtain an intermediate 3,4-dichloronitrobenzene; and catalytic hydrogenation: dissolving 3,4-dichloronitrobenzene in a solvent, adding a Pd-loaded active carbon catalyst, adding a dechlorination inhibitor, then carrying out preheating, allowing a preheated product and hydrogen to enter a reaction module group for a reaction and carrying outpost-treatment so as to obtain 3,4-dichloroaniline. The method provided by the invention is good in material mixing effect, accurate in material proportion control, capable of improving reaction yield and product purity, safe and stable in reactions, short in synthesis time and free of amplification effect, and has good application prospects in industrial production.
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Paragraph 0027; 0041-0042; 0047; 0053-0055; 0061; 0063
(2018/05/16)
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- Catalytic hydrogenation process of chlorine-containing nitro aromatic compound
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The invention discloses a catalytic hydrogenation process of a chlorine-containing nitro aromatic compound. The specific process comprises the following steps: adding a chlorine-containing nitrobenzene, water and an anti-dechlorination agent into a reactor, carrying out mixing by stirring, then adding a catalyst and a self-prepared cocatalyst, introducing nitrogen into the reactor for 5-10 min toreplace air in the reactor, then introducing hydrogen until the pressure is 18-26 kg, carrying out a reaction at 55-75 DEG C for 1-3 hours, carrying out cooling to room temperature after the reactionis finished, and detecting the content of the target product in the obtained product. The process conditions are mild, the effect of the reaction substrate on the catalyst is small, the catalytic activity is high, and the yield of the product is high.
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Paragraph 0040; 0041; 0042; 0043
(2018/11/27)
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- Direct Hydrogenation of a Broad Range of Amides under Base-free Conditions using an Efficient and Selective Ruthenium(II) Pincer Catalyst
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The ruthenium(II) complex, [fac-PNHN]RuH(η1-BH4)(CO) (B; PNHN=8-(2-diphenylphosphinoethyl)aminotrihydroquinoline), is a highly versatile and effective catalyst (loadings of 0.1–1 mol %) for the hydrogenation of a multitude of amides, which include primary, secondary, and tertiary amides, to give their corresponding alcohols and amines in high yields under base-free conditions. All products were confirmed by using GC and GC–MS.
- Wang, Zheng,Li, Yong,Liu, Qing-Bin,Solan, Gregory A.,Ma, Yanping,Sun, Wen-Hua
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p. 4275 - 4281
(2017/12/02)
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- Non-deprotonative primary and secondary amination of (hetero)arylmetals
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Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl-as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or Erecting groups. This one-pot transformation allows unprecedented functional group tolerance and it is wellsuited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper (l) salt is required.
- Zhou, Zhe,Ma, Zhiwei,Behnke, Nicole Erin,Gao, Hongyin,Kürti, László
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supporting information
p. 115 - 118
(2017/05/16)
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- ZnAl-Hydrotalcite-Supported Au25Nanoclusters as Precatalysts for Chemoselective Hydrogenation of 3-Nitrostyrene
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Chemoselective hydrogenation of 3-nitrostyrene to 3-vinylaniline is quite challenging because of competitive activation of the vinyl group and the nitro group over most supported precious-metal catalysts. A precatalyst comprised of thiolated Au25nanoclusters supported on ZnAl-hydrotalcite yielded gold catalysts of a well-controlled size (ca. 2.0 nm)—even after calcination at 500 °C. The catalyst showed excellent selectivity (>98 %) with respect to 3-vinylaniline, and complete conversion of 3-nitrostyrene over broad reaction duration and temperature windows. This result is unprecedented for gold catalysts. In contrast to traditional catalysts, the gold catalyst is inert with respect to the vinyl group and is only active with regard to the nitro group, as demonstrated by the results of the control experiments and attenuated total reflection infrared spectra. The findings may extend to design of gold catalysts with excellent chemoselectivity for use in the synthesis of fine chemicals.
- Tan, Yuan,Liu, Xiao Yan,Zhang, Leilei,Wang, Aiqin,Li, Lin,Pan, Xiaoli,Miao, Shu,Haruta, Masatake,Wei, Haisheng,Wang, Hua,Wang, Fangjun,Wang, Xiaodong,Zhang, Tao
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supporting information
p. 2709 - 2713
(2017/02/26)
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- Diethylenetriamine-Mediated Direct Cleavage of Unactivated Carbamates and Ureas
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Diethylenetriamine is effective for the direct cleavage of unactivated carbamates and ureas without additional reagents and catalysts. Various carbamates and ureas were cleaved to afford products in good yield, and the reactions were not affected by air or moisture. Unique chemoselective cleavage of carbamate and urea in the presence of amides was also achieved.
- Noshita, Megumi,Shimizu, Yuhei,Morimoto, Hiroyuki,Ohshima, Takashi
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supporting information
p. 6062 - 6065
(2016/12/09)
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- A production method for producing 3,4-dichloroaniline to aminochlorobenzene process and (by machine translation)
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The invention relates to a process for producing 3, 4-dichloroaniline and parachloroaniline based on a combined production method. The process comprises the following steps: chloridizing parachloronitrobenzene, and directly hydrotreating in a hydrogenated kettle in the absence of solvents at the temperature of 80+/-5 DEG C and the pressure of 0.5-0.6 Mpa to generate a mixed solution of parachloroaniline accounting for 20-35 percent of the mixed solution and 3, 4-dichloroaniline, then carrying out continuous rectification to produce parachloroaniline from the top of the tower and a mixed solution containing no parachloroaniline from the bottom of the tower, and rectifying the mixed solution to obtain 3, 4-dichloroaniline. The process for producing 3, 4-dichloroaniline and parachloroaniline based on a combined production method is suitable for production of large-output products, especially for temperature-sensitive chemical reaction, is labor-saving, easily and automatically controlled and simply and safely operated, has good stability, and is suitable for wide popularization and application.
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Paragraph 0020-0022
(2017/03/25)
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- A Metal and Base-Free Chemoselective Primary Amination of Boronic Acids Using Cyanamidyl/Arylcyanamidyl Radical as Aminating Species: Synthesis and Mechanistic Studies by Density Functional Theory
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An efficient, metal and base-free, chemoselective synthesis of aryl-, heteroaryl-, and alkyl primary amines from the corresponding boronic acids has been achieved at ambient temperature mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) and N-bromosuccinimide (NBS) using cyanamidyl/arylcyanamidyl radicals as the aminating species. The primary amine compounds were initially obtained as their corresponding ammonium trifluoroacetate salts which, on treatment with aq NaOH, provide the free amines. Finally, the primary amines were isolated through column chromatography over silica-gel using hexane-EtOAc solvent system as the eluent. The reactions are sufficiently fast, completing within 1 h. Quantum chemical calculations in combination with experimental observations validate that the ipso amination of substituted boronic acids involves the formation of cyanamidyl/arylcyanamidyl radical, followed by regiospecific interaction of its nitrile-N center with boron atom of the boronic acids, leading to chemoselective primary amination.
- Chatterjee, Nachiketa,Arfeen, Minhajul,Bharatam, Prasad V.,Goswami, Avijit
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p. 5120 - 5127
(2016/07/06)
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- Liquid-phase catalytic hydrogenation of 3,4-dichloronitrobenzene over Pt/C catalyst under gradient-free flow conditions in the presence of pyridine
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Experimental data on nitro compound uptake, the intermediate product accumulation, and the corresponding amine compound generation were obtained on hydrogenating 3,4-dichloronitrobenzene over Pt/C catalyst in the gradient-free flow regime in the presence and absence of pyridine. In addition, a side reaction of dehalogenation was investigated. The role of pyridine admixture on every step of the process was analyzed and the rate of hydrogenation of the nitro compound was determined both in the presence and in the absence of inhibitor.
- Dorokhov,Dorokhova,Savchenko
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p. 2040 - 2045
(2017/04/03)
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- Multifunctional Fe3O4@: N SiO2@ m SiO2/Pr-Imi-NH2·Ag core-shell microspheres as highly efficient catalysts in the aqueous reduction of nitroarenes: Improved catalytic activity and facile catalyst recovery
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Core@shell nanoparticles with a superparamagnetic iron oxide core, a middle nonporous silica shell, and an outer organo functionalized mesoporous silica shell were synthesized and evaluated for immobilizing Ag nanoparticles. The iron oxide nanoparticles cores were synthesized via improved chemical coprecipitation method and they were silica-coated by surface silylation via a Stober sol-gel process. Afterward, magnetic core-shell structured mesoporous silica microspheres, Fe3O4@nSiO2@mSiO2, were synthesized by silylation of Fe3O4@nSiO2 surface using tetraethyl orthosilicate through surfactant directed self-assembly on the surface, followed by etching of the surfactant molecules. Further modification of the surface by grafting of 3-chloropropyl triethoxysilane, nucleophilic substitution reaction of the chloride with imidazole and then quaternization with 2-bromo ethylamine hydrobromide produced the 2-amino ethyl-3-propyl imidazolium bromide functionalized magnetic core-shell structured mesoporous silica microspheres, Fe3O4@nSiO2@mSiO2/Pr-Im-NH2. Finally, the target nanocomposite, Fe3O4@nSiO2@mSiO2/Pr-Im-NH2·Ag was formed by embedding the silver nanoparticles into the mesoporous nanocomposite. The organic-inorganic nanocomposite was characterized by FT-IR spectroscopy, transmission electron microscopy (TEM), elemental analysis (CHN), vibrating sample magnetometer (VAM), thermogravimetric analysis (TGA) and differential thermal analysis (DTA), X-ray diffraction (XRD) and Brunauer-Emmett-Teller (BET). The catalytic activity test with the nitroarene reduction in an aqueous medium by using NaBH4 reveals that this Ag-supported nanocomposite is highly active for a wide range of substrates, suggesting highly promising application potentials of the magnetic core-shell-structured mesoporous organosilica. This method has the advantages of high yields, a cleaner reaction, simple methodology, short reaction times, easy workup, and greener conditions. In addition to the facility of this methodology, it also enhances product purity and promises economic as well as environmental benefits.
- Nasab, Mina Jafari,Kiasat, Ali Reza
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p. 41871 - 41877
(2016/05/24)
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- Diuron-intermediate production waste residue treatment technology
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A provided diuron-intermediate production waste residue treatment technology comprises the following steps: firstly crushing a catalyst anhydrous ferric chloride into a micro powder, and transferring into a reaction kettle; dropwise adding p-chloronitrobenzene in a fusion state into the above mentioned reaction kettle, and introducing chlorine into the reaction kettle at the same time; then introducing nitrogen into the above mentioned reaction kettle for first gas expelling; then transferring the above mentioned material subjected to gas expelling into a reduction kettle, and dropwise adding formic acid into the reduction kettle; then adding iron powder and water into the above mentioned reduction kettle, and slowly stirring; performing nitrogen secondary gas expelling on the above mentioned material; and cooling the material subjected to secondary gas expelling. By employing the above mentioned production technology, solid byproducts can be thoroughly filtered and separated, the purity of 3,4-dichloroaniline is guaranteed, and also resource waste is avoided, and also reaction efficiency is improved, reaction time is reduced, and the recovery yield is relatively high.
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Paragraph 0032; 0033; 0034; 0035; 0036; 0037
(2016/11/28)
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- Under the conditions of a solvent-free method of hydrogenation to synthesize haloarylamine
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The invention provides a method for synthesising halogenated aromatic amine through hydrogenation in a solvent-free condition. The method comprises the following step of: carrying out a liquid-phase hydrogenation reaction on the halogenated aromatic nitro compound shown in formula (I) under the action of hydrogen, in the absence of a solvent and a dehalogenation inhibitor under the action of a carbon-supported large-particle-size precious metal catalyst to prepare the halogenated aromatic amine shown in formula (II). The method provided by the invention is capable of achieving the effect of inhibiting a hydrogenation dehalogenation side reaction in the case of not adding a dehalogenation inhibitor, is high in target product selectivity, and is capable of remarkably increasing the reaction speed.
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Paragraph 0055-0058
(2017/03/21)
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- Metal and base free synthesis of primary amines via ipso amination of organoboronic acids mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA)
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A metal and base free synthesis of primary amines has been developed at ambient temperature through ipso amination of diversely functionalized organoboronic acids, employing a combination of [bis(trifluoroacetoxy)iodo]benzene (PIFA)-N-bromosuccinimide (NBS) and methoxyamine hydrochloride as the aminating reagent. The amines were primarily obtained as their trifluoroacetate salts which on subsequent aqueous alkaline work up provided the corresponding free amines. The combination of PIFA-NBS is found to be the mildest choice compared to the commonly used strong bases (e.g. n-BuLi, Cs2CO3) for activating the aminating agent. The reaction is expected to proceed via activation of the aminating reagent followed by B-N 1,2-aryl migration.
- Chatterjee, Nachiketa,Goswami, Avijit
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supporting information
p. 7940 - 7945
(2015/07/27)
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- ACTIVATORS OF MYOSIN II FOR MODULATING CELL MECHANICS
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The present invention discloses small molecule compounds as activators of myosin II by promoting its assembly and recruitment to contractile structures in the cell and methods of using such compounds. These compounds are useful to modulate cell and tissue mechanics. This class of molecules, which affect cell mechanics either by activating the contractile system of the cell or modulating cytokinesis, will be used for therapeutic and tissue engineering applications.
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Paragraph 00160
(2015/07/07)
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- Chemoselective Transfer Hydrogenation of Nitroarenes Catalyzed by Highly Dispersed, Supported Nickel Nanoparticles
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A recyclable highly dispersed Ni/SiO2 catalyst was prepared by atomic layer deposition. Chemoselective reduction of nitroarenes was studied using the prepared Ni/SiO2 as the catalyst and hydrazine hydrate as a hydrogen donor. Different kinds of nitroarenes were converted to the corresponding anilines with high yields. The high activity of the catalysts could be a result of the highly dispersed Ni nanoparticles. (Chemical Presented).
- Jiang, Chengjun,Shang, Zeyu,Liang, Xinhua
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p. 4814 - 4818
(2015/08/18)
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- Kinetics of the liquid-phase catalytic hydrogenation of chlorine-containing aromatic nitro compounds in the presence of pyridine
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We have analyzed experimental kinetic data for nitro compound consumption, for the formation of the corresponding amino product, and for the accumulation of intermediate products and by-products in the hydrogenation of chlorine-containing aromatic nitro compounds. The reaction has been carried out under static conditions over a platinum catalyst on a porous support in the presence of pyridine. The effect of the admixture on different hydrogenation steps of a chlorine-containing aromatic nitro compound has been quantitatively interpreted.
- Dorokhov,Savchenko
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p. 446 - 455
(2014/12/09)
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- Immobilized iron oxide nanoparticles as stable and reusable catalysts for hydrazine-mediated nitro reductions in continuous flow
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An experimentally easy to perform method for the generation of alumina-supported Fe3O4 nanoparticles [(6±1)nm size, 0.67 wt%]and the use of this material in hydrazine-mediated heterogeneously catalyzed reductions of nitroarenes to anilines under batch and continuous-flow conditions is presented. The bench-stable, reusable nano-Fe3O4@Al2O3 catalyst can selectively reduce functionalized nitroarenes at 1 mol% catalyst loading by using a 20 mol% excess of hydrazine hydrate in an elevated temperature regime (150°C, reaction time 2-6 min in batch). For continuous-flow processing, the catalyst material is packed into dedicated cartridges and used in a commercially available high-temperature/-pressure flow device. In continuous mode, reaction times can be reduced to less than 1 min at 150°C (30 bar back pressure) in a highly intensified process. The nano-Fe3O4@Al2O3 catalyst demonstrated stable reduction of nitrobenzene (0.5 m in MeOH) for more than 10 h on stream at a productivity of 30mmolh-1 (0.72 mol per day). Importantly, virtually no leaching of the catalytically active material could be observed by inductively coupled plasma MS monitoring.
- Moghaddam, Mojtaba Mirhosseini,Pieber, Bartholom?us,Glasnov, Toma,Kappe, C. Oliver
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p. 3122 - 3131
(2015/09/28)
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- Rapid, efficient and selective reduction of aromatic nitro compounds with hydrazine hydrate in the presence of the plain and supported platinum nanoparticles as catalysts
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The current study aimed at application of the plain and supported platinum nanoparticles as a heterogenous catalyst for the reduction of aromatic nitro compounds. Monodispersed platinum nanoparticles were synthesized by reduction of H2PtCl6 by ethanol in the presence of polyvinyl pyrrolidone as a stabilizer, and then were immobilized on four types of zeolites. The obtained catalyst granules were characterized by X-ray diffractometry and transmission electron microscopy. The study then focused on elaboration of the catalytic activity of the nano catalysts under different operational conditions. It was found that reaction is adequately rapid at ambient temperature, and by utilizing a sufficient amount of catalyst, can be completed in nearly 30 min. Among the utilized zeolitic supports, zeolite 4A had the highest performance, but the mechanism of its synergetic effect on the activity of platinum nano catalyst was not found and requires more investigation.
- Mehdizadeh, Soofia,Ahmadi, Seyed Javad,Sadjadi, Sodeh,Outokesh, Mohammad
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p. 1587 - 1592
(2015/01/09)
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- Highly efficient rhodium-catalyzed transfer hydrogenation of nitroarenes into amines and formanilides
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An efficient and selective rhodium-catalyzed transfer hydrogenation of nitroarenes with formic acid as the hydrogen source to give amines or formanilides has been developed. The addition of iodide ion accelerates the reaction, which can take place at room temperature. Georg Thieme Verlag Stuttgart New York.
- Wei, Yawen,Wu, Jianjun,Xue, Dong,Wang, Chao,Liu, Zhaotie,Zhang, Zhuozhuo,Chen, Guangfu,Xiao, Jianliang
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p. 1295 - 1298
(2014/06/10)
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- Hydrazine-mediated reduction of nitro and azide functionalities catalyzed by highly active and reusable magnetic iron oxide nanocrystals
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Iron oxide (Fe3O4) nanocrystals generated in situ from an inexpensive and readily available iron source catalyze the reduction of nitroarenes to anilines with unparalleled efficiency. The procedure is chemoselective, avoids the use of precious metals, and can be applied under mild reflux conditions (65 or 80 C) or using sealed vessel microwave heating in an elevated temperature regime (150 C). Utilizing microwave conditions, a variety of functionalized anilines have been prepared in nearly quantitative yields within 2-8 min at 150 C, in a procedure also successfully applied to the reduction of aliphatic nitro compounds and azides. The iron oxide nanoparticles are generated in a colloidal form, resulting in homogeneous solutions suitable for continuous flow processing. Selected examples of anilines of industrial importance have been prepared in a continuous regime using this protocol.
- Cantillo, David,Moghaddam, Mojtaba Mirhosseini,Kappe, C. Oliver
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p. 4530 - 4542
(2013/06/05)
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- Dialkylimidazole inhibitors of Trypanosoma cruzi sterol 14α-demethylase as anti-Chagas disease agents
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New dialkylimidazole based sterol 14α-demethylase inhibitors were prepared and tested as potential anti-Trypanosoma cruzi agents. Previous studies had identified compound 2 as the most potent and selective inhibitor against parasite cultures. In addition, animal studies had demonstrated that compound 2 is highly efficacious in the acute model of the disease. However, compound 2 has a high molecular weight and high hydrophobicity, issues addressed here. Systematic modifications were carried out at four positions on the scaffold and several inhibitors were identified which are highly potent (EC50 1 nM) against T. cruzi in culture. The halogenated derivatives 36j, 36k, and 36p, display excellent activity against T. cruzi amastigotes, with reduced molecular weight and lipophilicity, and exhibit suitable physicochemical properties for an oral drug candidate.
- Suryadevara, Praveen Kumar,Racherla, Kishore Kumar,Olepu, Srinivas,Norcross, Neil R.,Tatipaka, Hari Babu,Arif, Jennifer A.,Planer, Joseph D.,Lepesheva, Galina I.,Verlinde, Christophe L.M.J.,Buckner, Frederick S.,Gelb, Michael H.
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supporting information
p. 6492 - 6499
(2013/11/19)
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- Sunlight photocatalytic degradation of propanil in aqueous solution and determination of degraded products with UV-and HPLC
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The solar photocatalytic of an aqueous propanil were carried out under natural weathering conditions. Photocatalytic of 20 μg/mL propanil solution degraded 95 % of the solution after 3 h of solar irradiation, by using 10 mg of zinc oxide as a catalyst. The effect of various parameters such as amount of catalyst and illumination time on the degradation of propanil has been studied. The degradation percentages were investigated by monitoring the propanil mineralization spectrophotometrically. The mineralization rate of propanil is calculated.
- Dhahir, Saadiyah A.
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p. 5490 - 5492
(2013/01/15)
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- Enhanced mineralization of diuron using a cyclodextrin-based bioremediation technology
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The phenylurea herbicide diuron [N-(3,4-dichlorophenyl)-N,N-dimethylurea] is widely used in a broad range of herbicide formulations and, consequently, it is frequently detected as a major soil and water contaminant in areas where there is extensive use. Diuron has the unfortunate combination of being strongly adsorbed by soil organic matter particles and, hence, slowly degraded in the environment due to its reduced bioavailability. N-Phenylurea herbicides seem to be biodegraded in soil, but it must be kept in mind that this biotic or abiotic degradation could lead to accumulation of very toxic derived compounds, such as 3,4-dichloroaniline. Research was conducted to find procedures that might result in an increase in the bioavailability of diuron in contaminated soils, through solubility enhancement. For this purpose a double system composed of hydroxypropyl-β-cyclodextrin (HPBCD), which is capable of forming inclusion complexes in solution, and a two-member bacterial consortium formed by the diuron-degrading Arthrobacter sulfonivorans (Arthrobacter sp. N2) and the linuron-degrading Variovorax soli (Variovorax sp. SRS16) was used. This consortium can achieve a complete biodegradation of diuron to CO2 with regard to that observed in the absence of the CD solution, where only a 45% biodegradation was observed. The cyclodextrin-based bioremediation technology here described shows for the first time an almost complete mineralization of diuron in a soil system, in contrast to previous incomplete mineralization based on single or consortium bacterial degradation.
- Villaverde, Jaime,Posada-Baquero, Rosa,Rubio-Bellido, Marina,Laiz, Leonila,Saiz-Jimenez, Cesareo,Sanchez-Trujillo, Maria A.,Morillo, Esmeralda
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p. 9941 - 9947,7
(2020/09/15)
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- In situ generated iron oxide nanocrystals as efficient and selective catalysts for the reduction of nitroarenes using a continuous flow method
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The best of both worlds: The benefits of homogeneous and heterogeneous nanocatalysis are combined, whereby highly reactive colloidal Fe 3O4 nanocrystals are generated in situ that remain in solution long enough to allow the efficient and selective reduction of nitroarenes to anilines in continuous-flow mode (see scheme). After completion of the reaction, the nanoparticles aggregate and can be recovered by a magnet. Copyright
- Cantillo, David,Baghbanzadeh, Mostafa,Kappe, C. Oliver
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p. 10190 - 10193
(2012/11/07)
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- Highly selective hydrogenation of halonitroaromatics to aromatic haloamines by ligand modified Ni-based catalysts
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Ligand modification of Ni-based catalysts by coordination of dicyandiamide to Ni metal leads to enhanced selectivity for the selective hydrogenation of halonitroaromatics. The selectivity of above 99.9% to aromatic haloamines can be achieved at the conversion of 100%. The results of H2-TPD and FT-IR experiments show that Ni-H+ species possessing the properties of Lewis acid site on the surface of Raney Ni could be responsible for the hydrodehalogenation. When Raney Ni was treated by dicyandiamide, Ni -H+ species interacted with N atom from the dicyandiamide. This interaction was stable even at reaction temperature, which reduced the possibility to form the intermediate state of ArCl?H+Ni -. And then CCl bond could not be polarized and activated. The hydrodechlorination process was suppressed effectively.
- Lu, Chun Shan,Lv, Jing Hui,Ma, Lei,Zhang, Qun Feng,Feng, Feng,Li, Xiao Nian
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experimental part
p. 545 - 548
(2012/06/16)
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- An efficient method for aryl nitro reduction and cleavage of azo compounds using iron powder/calcium chloride
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A novel, efficient Fe/CaCl2 system is revealed for the reduction of nitroarenes and reductive cleavage of azo compounds by catalytic transfer hydrogenation (CTH). The selective reduction of nitro compounds in the presence of sensitive functional groups including halides, carbonyl, hydroxyl, aldehyde, methyl, methoxy, acetyl, nitrile, and ester substituents with an excellent yields is reported. The simple experimental procedure and easy purification make the protocol advantageous
- Chandrappa,Vinaya,Ramakrishnappa,Rangappa
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experimental part
p. 3019 - 3022
(2011/03/17)
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- Hydrous zirconia supported iridium nanoparticles: An excellent catalyst for the hydrogenation of haloaromatic nitro compounds
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Ir/ZrO2·xH2O was prepared by co-precipitation and characterized by TEM, XRD, and XPS. It showed an excellent catalytic performance for the hydrogenation of haloaromatic nitro compounds to the corresponding amines in the mixture solvent of ethanol and water. The catalyst gave both conversion and selectivity to be over 99.9% for the hydrogenation of p-chloronitrobenzene to p-chloroaniline. Besides the intrinsic characterization of iridium in the hydrogenation of haloaromatic nitro compounds, the high activity and selectivity of Ir/ZrO2·xH2O is probably attributed to the formation of hydrogen bond between substrate and the hydroxyl groups on the surface of the hydrous catalyst or solvent water to activate the N{double bond, long}O bond in nitro group. The activated N{double bond, long}O bond is easy to be attacked by the activated hydrogen, so the hydrogenation is promoted.
- Fan, Guang-Yin,Zhang, Lei,Fu, Hai-Yan,Yuan, Mao-Lin,Li, Rui-Xiang,Chen, Hua,Li, Xian-Jun
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scheme or table
p. 451 - 455
(2010/11/21)
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- Immobilized silver nanoparticles on silica gel as an efficient catalyst in nitroarene reduction
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Nanoparticles have properties that can be fine-tuned by their size as well as shape. Hence, there is significant current interest in preparing nano-materials of small size dispersity and to arrange them in close-packed aggregates. This letter describes a way of synthesising silver nanoparticles and their protection to aggregate by silica gel. The combination of catalytic quantities of immobilized silver nanoparticles with reductive ability of NaBH4 efficiently reduces aromatic nitroarenes to the corresponding amines in aqueous medium. Noteworthy is that highly chemoselective reactions were achieved in the presence of other functional groups such as halogen and carboxylic acid groups. The silver particles immobilized on silica gel are stable in the presence of oxygen for several months.
- Kiasat, Ali Reza,Mirzajani, Roya,Ataeian, Fakhri,Fallah-Mehrjardi, Mehdi
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experimental part
p. 1015 - 1019
(2011/10/05)
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- Efficient reduction of nitroarenes over nickel-iron mixed oxide catalyst prepared from a nickel-iron hydrotalcite precursor
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Nickel-iron mixed oxide prepared from a nickel-iron hydrotalcite precursor was found to be a highly efficient catalyst for the chemoselective reduction of nitroarenes under mild reaction conditions.
- Shi, Qixun,Lu, Rongwen,Lu, Lianhai,Fu, Xinmei,Zhao, Defeng
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p. 1877 - 1881
(2008/09/17)
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- Ag/SiO2: A novel catalyst with high activity and selectivity for hydrogenation of chloronitrobenzenes
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Ag/SiO2 prepared by an in situ reduction method are found, for the first time, to be highly effective and recyclable catalysts for the selective hydrogenation of a range of chloronitrobenzes to their corresponding chloroanilines, which are of great potential as industrially viable and cheap novel catalysts for the production of chloroanilines. The Royal Society of Chemistry 2005.
- Chen, Yangying,Wang, Chuang,Liu, Hongyang,Qiu, Jieshan,Bao, Xinhe
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p. 5298 - 5300
(2007/10/03)
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- Selective reduction of azoarenes into arylamine(s) by aluminium/NH 4Br under sonic conditions
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Azoarenes, both symmetrical and unsymmetrical are cleaved into arylamine/s by aluminium metal and ammonium bromide in refluxing methanol with high yields. The rate of the reaction is greatly accelerated by irradiating at 35 kHz in a sonic bath maintained at 25 °C.
- Pasha,Jayashankara
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p. 282 - 283
(2007/10/03)
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- Synthesis of oxazines and N-arylpyrroles by reaction of unfunctionalized dienes with nitroarenes and carbon monoxide, catalyzed by palladium-phenanthroline complexes
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The reaction between an unfunctionalized conjugated diene and a nitroarene under CO pressure and at 100 °C, catalyzed by [Pd(Phen)2][BF4]2 (Phen = 1,10-phenanthroline), affords the corresponding hetero-Diels -Alder adduct (oxazine) in up to 91% yields in one pot. If the reaction mixture is then heated to 200 °C, the oxazines are converted into the corresponding N-arylpyrroles in good yields. Pressures as low as 5 bar can be employed, and 0.08% catalyst is sufficient to effect the transformation. The reaction can be equally run by employing the nitroarene or the diene as limiting agent and works well for nitroarenes bearing either electron-withdrawing or mildly electron-donating substituents. A moderate steric hindrance on the nitroarene (o-methyl) is well tolerated, but 1,4-disubstituted-1,3-dienes are not suitable substrates.
- Ragaini, Fabio,Cenini, Sergio,Brignoli, Daniela,Gasperini, Michela,Gallo, Emma
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p. 460 - 466
(2007/10/03)
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- Biotransformation of phenylurea herbicides by a soil bacterial strain, Arthrobacter sp. N2: Structure, ecotoxicity and fate of diuron metabolite with soil fungi
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In order to assess the influence of the aromatic substitution on the ability of a soil bacterial strain, Arthrobacter sp. N2, to degrade phenylurea herbicides, biotransformation assays were performed in mineral medium with resting cells of this soil bacterial strain on three phenylurea herbicides (diuron, chlorotoluron and isoproturon). Each herbicide considered, led to the formation of only one metabolite detected by HPLC analysis. After isolation, the metabolites were identified by NMR and MS, as the corresponding substituted anilines. According to the Microtox test (realized on the bacterium Vibrio fischeri), these metabolites presented non-target toxicity far more important (up to 600 times higher for 4-isopropylaniline) than the parent molecule. For isoproturon and chlorotoluron, the amount of substituted anilines obtained at the end of the biotransformation was very low, whereas the biotransformation of diuron into 3,4-dichloroaniline was almost quantitative. In this last case, the degradation product accumulated in the medium. In soil, other microorganisms are present that might degrade it. So the biotransformation of 3,4-dichloroaniline was then tested with four fungal strains: Aspergillus niger, Beauveria bassiana, Cunninghamella echinulata var. elegans and Mortierella isabellina. The aniline was further transformed with all the microorganisms tested. Only one metabolite was detected by HPLC analysis and after isolation, it was identified to be 3,4-dichloroacetanilide. This acetylated compound led to biological effects less important on V. fischeri than 3,4-dichloroaniline. These results stress the importance of identifying the degradation products to assess the impact of a polluting agent. Indeed, the pollutant may undergo transformation yielding compounds more toxic than the parent molecule.
- Tixier,Sancelme,Ait-Aissa,Widehem,Bonnemoy,Cuer,Truffaut,Veschambre
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p. 519 - 526
(2007/10/03)
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