2085-88-3Relevant articles and documents
A graphene oxide immobilized Cu(ii) complex of 1,2-bis(4-aminophenylthio)ethane: An efficient catalyst for epoxidation of olefins with tert-butyl hydroperoxide
Zarnegaryan, Ali,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammdpoor-Baltork, Iraj
, p. 2280 - 2286 (2016)
In this work, a new, recoverable and heterogeneous catalyst was prepared by covalent attachment of the Cu(ii) complex of 1,2-bis(4-aminophenylthio)ethane onto graphene oxide via the amide linkages. The structural and chemical nature of the catalyst was characterized by a variety of techniques such as Fourier transform infrared and diffuse reflectance UV-visible spectroscopies, X-ray diffraction, thermogravimetric analysis, transmission electron microscopy, field emission scanning electron microscopy and inductively coupled plasma atomic emission spectroscopy. The catalytic activity of this catalyst was investigated in the epoxidation of olefins with tert-butyl hydroperoxide. The catalyst has great reusability and stability in the epoxidation reactions.
m-Chloroperoxybenzoic Acid-Potassium Fluoride System: Study of Its Stability and Reaction with α-Methylstyrene
Camps, F.,Coll, J.,Messeguer, A.,Pujol, F.
, p. 5402 - 5404 (1982)
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Molybdenum Schiff base-polyoxometalate hybrid compound: A heterogeneous catalyst for alkene epoxidation with tert-BuOOH
Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Javadi, Maedeh Moshref
, p. 648 - 654 (2010)
The hybrid compound consisting of molybdenum(salen) [salen = N,N′-bis(salicylidene)ethylnediamine] complex covalently linked to a lacunary Keggin-type polyoxometalate, K8[SiW11O39] (POM), was synthesized and characterized by elemental analysis, FT-IR, 1H NMR and diffuse reflectance UV-Vis spectroscopic methods and BET analysis. The complex, [Mo(O)2(salen)-POM], was studied, for the first time, in the epoxidation of various alkenes with tert-BuOOH and in 1,2-dichloroethane as solvent. This catalyst can catalyze epoxidation of various olefins including non-activated terminal olefins. The effect of the other parameters such as solvent, oxidant and temperature on the epoxidation of cyclooctene was also investigated. The interesting characteristic of this catalyst is that, in addition to being a heterogeneous catalyst, it gives higher yields towards epoxidation of olefins in comparison to the corresponding homogeneous [Mo(O)2(salen)] complex.
Cleavage of the Carbon-Carbon Double Bond over Zeolites using Hydrogen eroxide
Reddy, J. Sudhakar,Khire, Uday R.,Ratnasamy, P.,Mitra, Rajat B.
, p. 1234 - 1235 (1992)
Zeolite molecular sieves catalyse the cleavage of carbon-carbon double bonds of various alkenes in the presence of aqueous hydrogen peroxide as an oxidant; titanium silicate molecular sieves, TS-1 and TS-2 exhibit very high activity in the conversion of α-methylstyrene into acetophenone.
Dialkyl peroxides decomposition in the presence of quaternary ammonium halides
Maksyuta,Suprun,Opeida,Turovskii
, p. 814 - 818 (2001)
Decomposition of dicumyl peroxide and cumyl tert-butyl peroxide was studied in the presence of tetraethylammonium halides in acetonitrile, dimethylformamide, 2-propanol, and acetic acid. The tetraethylammonium halides accelerate the decomposition of dialkyl peroxides in 2-propanol and acetic acid, but do not affect the reaction velocity in dimethylformamide and acetonitrile. The decomposition products character depends on the solvent nature.
Enhancement of the photoinduced oxidation activity of a ruthenium(II) complex anchored on silica-coated silver nanoparticles by localized surface plasmon resonance
Mori, Kohsuke,Kawashima, Masayoshi,Che, Michel,Yamashita, Hiromi
, p. 8598 - 8601 (2010)
Plasmonic photocatalyst: Anchoring the dye [Ru(bpy)3] 2+ (bpy=2,2-bipyridine) on the surface of Ag nanoparticles coated with a thin SiO2 layer (see picture) afforded a photocatalyst whose phosphorescence emission and photoinduced oxidation activity in the selective liquid-phase oxidation of styrene are efficiently enhanced through interaction with the localized surface plasmon resonance of the core Ag nanoparticles.
Photoinduced electron transfer oxidation of α-methylstyrene with molecular oxygen sensitized by dimethoxybenzenes: A non-singlet-oxygen mechanism
Mori, Tadashi,Takamoto, Makoto,Tate, Yoshimasa,Shinkuma, Junya,Wada, Takehiko,Inoue, Yoshihisa
, p. 2505 - 2508 (2001)
α-Methylstyrene (1) was photooxidized with oxygen in the presence of a series of alkylated dimethoxybenzenes as a sensitizer in acetonitrile, affording the cleaved ketone (2), epoxide (3) as well as a small amount of the ene product (4) in ca. 1:1:0.04 ratio. A non-singlet-oxygen mechanism is proposed, in which an excited sensitizer is quenched by oxygen to produce a sensitizer radical cation and a superoxide ion (O2·-), the former of which oxidizes 1, while O2·- reacts with the resulting 1·+ to give the major oxidation products.
An efficient biomimetic Fe-catalyzed epoxidation of olefins using hydrogen peroxide
Anilkumar, Gopinathan,Bitterlich, Bianca,Gelalcha, Feyissa Gadissa,Tse, Man Kin,Beller, Matthias
, p. 289 - 291 (2007)
A new, environmentally benign and practical epoxidation method was developed using inexpensive and efficient Fe catalysts. FeCl3· 6H2O in combination with commercially available pyridine-2,6- dicarboxylic acid and amines showed excellent reactivity and selectivity towards aromatic olefins and moderate reactivity towards 1,3-cyclooctadiene utilizing H2O2 as the terminal oxidant. The Royal Society of Chemistry.
The in situ generation and use of iodomethyllithium for the one-carbon homologation of boronic esters and epoxide formation from carbonyl compounds
Wallace,Battle
, p. 127 - 133 (1995)
Iodomethyllithium is shown to be an effective reagent for the one-carbon homologation of oxygenated boronic esters. The use of iodomethyllithium for the preparation of pinacol iodomethaneboronate and for the synthesis of epoxides from carbonyl compounds is also discussed.
Synthesis of a new schiff base oxovanadium complex with melamine and 2-hydroxynaphtaldehyde on modified magnetic nanoparticles as catalyst for allyl alcohols and olefins epoxidation
Farzaneh, Faezeh,Asgharpour, Zeinab
, (2019)
A new magnetically recoverable nanocatalyst designated as Fe3O4@SiO2@PTMS@Mel-Naph-VOcomplex was synthesize by covalent binding of a Schiff base ligand derived from melamine and 2-hydroxy1naphtaldehyde on the surface of silica coated iron oxide magnetic nanoparticles followed by complexation with VO (acac)2. Characterization of the prepared nanocatalyst was accomplished with FT-IR, XRD, SEM, HRTEM, VSM and atomic absorption techniques. It was found that the epoxidation of geraniol, trans-2-hexen-1-ol, 1-octen-3-ol, norbornene, and cyclooctene is highly selective, affording quantitative yields of the corresponding epoxides with tert-butyl hydroperoxide (TBHP) using Fe3O4@SiO2@Mel-Naph-VOcomplex as catalyst. High reaction yields, short reaction times, simple experimental and work up procedure, catalyst stability and excellent reusability even after five-cycles of usage in the case of geraniol are some advantages of this research.
Substituted perhydrofuropyrans: Easy preparation from 2-chloromethyl-3- (2-methoxyethoxy)propene through 3-methylene-1,6-diols
Lorenzo, Emilio,Alonso, Francisco,Yus, Miguel
, p. 1661 - 1665 (2000)
The reaction of 2-chloromethyl-3-(2-methoxyethoxy)prop-1-ene (1) with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E1=R1R2CO) in THF at -78 to 0°C, followed by treatment with an epoxide [E2=R3R4C(O)CHR5] at 0 to 20°C leads, after hydrolysis, to the expected unsaturated diols 2. When some compounds 2 (2e-h) are successively hydroborated (BH3 · THF) and oxidised (33% H2O2 and then PCC), the expected perhydrofuropyrans 3e-h are isolated directly. (C) 2000 Elsevier Science Ltd.
Photoinduced electron-transfer oxidation of olefins with molecular oxygen sensitized by tetrasubstituted dimethoxybenzenes: A non-singlet-oxygen mechanism
Mori, Tadashi,Takamoto, Makolo,Wada, Takehiko,Inoue, Yoshihisa
, p. 2693 - 2707 (2001)
α-Methylstyrene (1) was photo-oxidized in the presence of a series of alkylated dimethoxybenzenes as sensitizers in an oxygen-saturated MeCN solution to afford the cleaved ketone 2, epoxide 3, as well as a small amount of the ene product 4 in ca. 1:1:0.04 ratio. The relative rate of conversion was well-correlated with the fluorescence quantum yield of sensitizers. Thus, a non-singlet-oxygen mechanism is proposed, in which an excited sensitizer is quenched by (ground-state) molecular oxygen to produce a sensitizer radical cation and a superoxide ion (O2-·), the former of which oxidizes the substrate, while the latter reacts with the resulting olefin radical cation (1-·) to give the major oxidation products. Photodurability of such electron-donating sensitizers is dramatically improved by substituting four aromatic H-atoms in 1,4-dimethoxybenzene with Me or fused alkyl groups, which provides us with an environmentally friendly, clean method of photochemical functionalization with molecular oxygen, alternative to the ene reaction via singlet oxygenation.
Epoxidation of alkenes with NaIO4 catalyzed by an efficient and reusable natural polymer-supported ruthenium(III) salophen catalyst
Hatefi Ardakani,Moghadam,Saeednia,Pakdin-Parizi
, p. 631 - 636 (2016)
In the present study, preparation, characterization, and catalytic activity of Ru(salophen)Cl supported on chitosan were investigated. The prepared heterogeneous catalyst was characterized by diffuse reflectance UV-vis and FT-IR spectroscopic techniques, scanning electron microscopy, and neutron activation analysis. In this catalytic system, the effects of different solvents were studied in the epoxidation of cis-cyclooctene and CH3CN/H2O was found to be a better solvent. Also, the effects of oxygen donors such as NaIO4, H2O2, H2O2/urea(UHP), tert-BuOOH, NaClO, and Bu4NIO4 were studied in the epoxidation of cis-cyclooctene and NaIO4 was selected as an oxidant. The catalytic activity of this new heterogeneous catalyst in the epoxidation of cyclic and linear alkenes using NaIO4 as an oxidant in CH3CN/H2O at room temperature was studied. The obtained results led us to conclude that [Ru(salophen)Cl@ chitosan] is an efficient catalyst for the epoxidation of alkenes with NaIO4. The catalyst can be readily recovered simply by filtration and reused several times without any significant loss in its catalytic activity.
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Niki,Kamiya
, p. 583,584 (1967)
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Catalytic activity of carbon nanotube supported iron(III) and manganese(III) porphyrins in oxidation of olefins with tert-butyl hydroperoxide: Higher activity of the iron(III) porphyrin
Rayati, Saeed,Jafarzadeh, Parisa,Zakavi, Saeed
, p. 40 - 44 (2013)
Oxidation of olefins with tert-butyl hydroperoxide (TBHP) catalyzed by carbon nanotube supported iron(III) and manganese(III) complexes of meso-tetrakis(4-hydroxyphenyl)porphyrin is reported. The results show higher catalytic activity of the Fe(III) complex compared to the Mn(III) one. With the exception of cyclooctene which gives cyclooctene oxide as the sole product, oxidation of styrene, α-methyl styrene and cyclohexene leads to the formation of benzaldehyde, acetophenone and cyclohexene-1-one as the major product, respectively. In this study, acetonitrile has been found to be the best solvent for reaction performed in the presence of the manganese and iron porphyrin. In comparison of the two metalloporphyrins, catalytic activity of the manganese porphyrin is more sensitive to the type of solvent than the iron one. In spite of the crucial role of imidazole (ImH) on catalytic performance of the manganese porphyrin, the presence of ImH has a negative effect on the activity of the iron porphyrin. The nano-tube supported iron porphyrin may be recovered and reused at least four times without significant loss of the catalytic activity.
Nickel complexes with N2O donor ligands: Syntheses, structures, catalysis and magnetic studies
Chakraborty, Jishnunil,Nandi, Mahasweta,Mayer-Figge, Heike,Sheldrick, William S.,Sorace, Lorenzo,Bhaumik, Asim,Banerjee, Pradyot
, p. 5033 - 5044 (2007)
Two new terephthalato-bridged tetranuclear polymeric NiII complexes, namely [Ni4L41(μ-tp- κ4-O)(H2O)2(μ-tp-κ2- O)]· 2C2H5OH·CH3OH·3H 2O (1) and [Ni4L42(μ-tp- κ4-O)(H2O)2(μ-tp-κ2- O)]·3H2O (2) [L1 = N-(3-aminopropyl)-5- bromosalicylaldimine and L2 = N-(3-aminopropyl)salicylaldimine], are reported along with the syntheses and structures of the dicyanoargentate-bridged polymeric complexes [Ni(L1)(H2O)-{Ag(CN) 2}]α (3) and [Ni(L3)(MeOH){Ag(CN) 2}]α (4) [L3 = N-(3-amino-2,2-dimethylpropyl)-5- bromosalicylaldimine]. All four complexes are found to be effective heterogeneous catalysts for the epoxidation of alkenes such as styrene, α-methylstyrene and cyclohexene in the presence of tert-butyl hydroperoxide. The variable-temperature magnetic susceptibility measurements (300-2 K) of complex 1 show a fair degree of antiferromagnetic coupling between the NiII centers. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Chiral porous poly(ionic liquid)s: Facile one-pot, one-step synthesis and efficient heterogeneous catalysts for asymmetric epoxidation of olefins
Tian, Yabing,Wang, Jixia,Zhang, Shiguo,Zhang, Yan
, (2022/01/26)
Ionic liquids are potential media/solvents for asymmetric synthesis when combined with chiral catalysts, while most reported catalysts are homogenous, making them difficult to separate from the reaction systems. Herein, chiral porous poly(ionic liquid)s (
Aerobic epoxidation of styrene over Zr-based metal-organic framework encapsulated transition metal substituted phosphomolybdic acid
Hu, Dianwen,Song, Xiaojing,Zhang, Hao,Chang, Xinyu,Zhao, Chen,Jia, Mingjun
, (2021/04/19)
Catalytic epoxidation of styrene with molecular oxygen is regarded as an eco-friendly alternative to producing industrially important chemical of styrene oxide (STO). Recent efforts have been focused on developing highly active and stable heterogeneous catalysts with high STO selectivity for the aerobic epoxidation of styrene. Herein, a series of transition metal monosubstituted heteropolyacid compounds (TM-HPAs), such as Fe, Co, Ni or Cu-monosubstituted HPA, were encapsulated in UiO-66 frameworks (denoted as TM-HPA@UiO-66) by direct solvothermal method, and their catalytic properties were investigated for the aerobic epoxidation of styrene with aldehydes as co-reductants. Among them, Co-HPA@UiO-66 showed relatively high catalytic activity, stability and epoxidation selectivity at very mild conditions (313 K, ambient pressure), that can achieve 82 % selectivity to STO under a styrene conversion of 96 % with air as oxidant and pivalaldehyde (PIA) as co-reductant. In addition, the hybrid composite catalyst can also efficiently catalyze the aerobic epoxidation of a variety of styrene derivatives. The monosubstituted Co atoms in Co-HPA@UiO-66 are the main active sites for the aerobic epoxidation of styrene with O2/PIA, which can efficiently converting styrene to the corresponding epoxide through the activation of the in-situ generated acylperoxy radical intermediate.
