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1195-92-2 Usage

Chemical Properties

clear colorless liquid

Definition

ChEBI: An epoxide resulting from the formal epoxidation of the cyclic double bond of limonene.

Check Digit Verification of cas no

The CAS Registry Mumber 1195-92-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,9 and 5 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1195-92:
(6*1)+(5*1)+(4*9)+(3*5)+(2*9)+(1*2)=82
82 % 10 = 2
So 1195-92-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1

1195-92-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name limonene 1,2-epoxide

1.2 Other means of identification

Product number -
Other names 1,2-Epoxylimonene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1195-92-2 SDS

1195-92-2Relevant articles and documents

Highly selective and recyclable MoO3 nanoparticles in epoxidation catalysis

Fernandes, Cristina I.,Capelli, Silvia C.,Vaz, Pedro D.,Nunes, Carla D.

, p. 344 - 350 (2015)

Molybdenum trioxide (MoO3) nanoparticles with an average size below 100 nm were prepared by solvothermal synthesis of nano-crystalline molybdenum dioxide (MoO2) and subsequent thermal oxidative annealing. The successful preparation of this type of nanoparticles was confirmed by evidence obtained from characterization by powder X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM) analysis and Fourier transform infrared spectroscopy (FTIR). The MoO3 nanoparticles were tested as catalytic precursor in the epoxidation of cis-cyclooctene, styrene, R-(+)-limonene and trans-hex-2-en-1-ol, using tert-butylhydroperoxide (tbhp) as oxygen source under different reaction conditions, namely, various solvents and temperatures. The catalytic studies show that the MoO3 nanoparticles perform selective epoxidation of the tested substrates with very high yield, especially at high temperature and using toluene as solvent. Furthermore, the catalyst remains active across several reaction cycles with virtually no loss of activity.

Hydrogen-peroxide epoxidation of natural olefins catalyzed by a dinuclear manganese complex

Mandelli,Voitiski,Schuchardt,Shul'pin

, p. 243 - 245 (2002)

The complex of Mn(IV) with the macrocyclic N-containing ligand 1,4,7-trimethyl-1,4,7-triazacyclononane (L) [L2Mn2O 3](PF6)2 catalyzes epoxidation of (+)-limonene in CH3CN solution at room temperature. Adding CH3COOH accelerates the reaction. The products are isomers of limonene epoxide with predominance of that with an epoxified ring double bond. Epoxidation of α- and β-pinene by this system is less effective, apparently due to extensive steric shielding of the double bonds in the pinenes.

Fluorinated alcohols: Effective solvents for uncatalysed epoxidations with aqueous hydrogen peroxide

Van Vliet,Arends,Sheldon

, p. 248 - 250 (2001)

Buffered aqueous hydrogen peroxide in combination with fluorinated alcohols (trifluoroethanol at reflux temperature or hexafluoro-2-propanol at room temperature) oxidises a variety of alkenes to the corresponding epoxides in high rates and fairly high yields, without the need for any catalyst.

Vanadyl cationic complexes as catalysts in olefin oxidation

Nunes, Carla D.,Vaz, Pedro D.,Félix, Vítor,Veiros, Luis F.,Moniz, Tania,Rangel, Maria,Realista, Sara,Mourato, Ana C.,Calhorda, Maria José

, p. 5125 - 5138 (2015)

Three new mononuclear oxovanadium(iv) complexes [VO(acac)(R-BIAN)]Cl (BIAN = 1,2-bis{(R-phenyl)imino}acenaphthene, R = H, 1; CH3, 2; Cl, 3) were prepared and characterized. They promoted the catalytic oxidation of olefins such as cyclohexene, cis-cyclooctene, and styrene with both tbhp (tert-butylhydroperoxide) and H2O2, and of enantiopure olefins (S(-)- and R(+)-pinene, and S(-)- and R(+)-limonene) selectively to their epoxides, with tbhp as the oxidant. The TOFs for styrene epoxidation promoted by complex 3 with H2O2 (290 mol mol-1V h-1) and for cis-cyclooctene epoxidation by 2 with tbhp (248 mol mol-1V h-1) are particularly good. Conversions reached 90% for several systems with tbhp, and were lower with H2O2. A preference for the internal CC bond, rather than the terminal one, was found for limonene. Kinetic data indicate an associative process as the first step of the reaction and complex [VO(acac)(H-BIAN)]+ (1+) was isolated in an FTICR cell after adding tbhp to 1. EPR studies provide evidence for the presence of a V(iv) species in solution, until at least 48 hours after the addition of tbhp and cis-cyclooctene, and cyclic voltammetry studies revealed an oxidation potential above 1 V for complex 1. DFT calculations suggest that a [VO(H-BIAN)(MeOO)]+ complex is the likely active V(iv) species in the catalytic cycle from which two competitive mechanisms for the reaction proceed, an outer sphere path with an external attack of the olefin at the coordinated peroxide, and an inner sphere mechanism starting with a complex with the olefin coordinated to vanadium. This journal is

Continuous flow photooxygenation of monoterpenes

Park, Chan Yi,Kim, Young Joon,Lim, Hyo Jin,Park, Jeong Hyeon,Kim, Mi Jin,Seo, Seung Woo,Park, Chan Pil

, p. 4233 - 4237 (2015)

Photooxygenation of monoterpenes was conducted in two continuous flow reactors. The first, suitable for lab-scale research, had a maximum yield of 99.9%, and the second, focused on industrial applications, showed a daily output that was 270.0-fold higher than that in batch systems. The use of sunlight instead of an LED lamp gave 68.28% conversion.

Remarkable axial ligand effect on regioselectivity towards terminal alkenes in epoxidation of dienes by a robust manganese porphyrin

Lai, Tat-Shing,Lee, Stephen K. S.,Yeung, Lam-Lung,Liu, Hai-Yang,Williams, Ian D.,Chang, Chi K.

, p. 620 - 621 (2003)

With a highly encumbered manganese porphyrin as catalyst, significant improvements in regioselectivity towards less substituted C-C double bond in diene epoxidation were attained by simply adding organic bases as axial ligand.

Lipase-mediated epoxidation of the cyclic monoterpene limonene to limonene oxide and limonene dioxide

Wiemann, Lars O.,Faltl, Christina,Sieber, Volker

, p. 1056 - 1060,5 (2012)

Limonene is an industrially interesting monoterpene that accumulates in bulk quantities as byproduct of the fruit juice industry. The corresponding epoxides are versatile synthetic intermediates and additives for the chemical industry. Due to a number of disadvantages of classical chemical epoxidation including serious safety issues and unwanted side-reactions, we here used a mild lipasecatalyzed chemo-enzymatic epoxidation system, with either free or different immobilized forms of Candida antarctica lipase B. Full limonene conversion (° 98%) was easily achieved at 40°C within less than 24 h. The enzymatic activities in the formation of limonene monoxide significantly varied from either 1-3.4 U/mgbiocatalyst at r.t. or from 1.7-4.9 U/mgbiocatalyst at 40°C. For the first time we showed that it is possible to generate high amounts of limonene dioxide (~ 30% with CalB on carrier 350 at 40°C) using this mild lipase-mediated epoxidation method. Enzyme activities and limonene dioxide yields strongly depend on the nature of the selected enzyme carrier, the immobilization method and the reaction temperature.

Efficient and selective epoxidation of alkenes with sodium periodate using supported manganese porphyrins under ultrasonic irradiation

Tangestaninejad, Shahram,Mirkhani, Valiollah

, p. 1265 - 1266 (1998)

Epoxides are readily obtained in high yields and good selectivities by ultrasonic irradiation of alkenes and sodium periodate in the presence of catalytic amounts of manganese porphyrins supported on polyvinylpyridine and IRA-900 ion-exchange resin.

Viable route and DFT study for the synthesis of optically active limonaketone: A barely available natural feedstock in Cedrus atlantica

Mekkaoui, Ayoub Abdelkader,Ben El Ayouchia, Hicham,Anane, Hafid,Chahboun, Rachid,El Firdoussi, Larbi,El Houssame, Soufiane

, (2021)

Herein, we report a novel, easy and efficient synthesis pathway of optically active limonaketone, a high added value monoterpene, starting from limonene, natural and low-cost feedstock. The strategy was developed in an excellent three-step total synthesis of limonaketone, potentially important intermediate in limonene ozonolysis and barely available in Cedrus atlantica essential oil (0.1% yield). The first step was the epoxidation of limonene which proceed in 91% yield. The ozonolysis of the prepared limonene oxide leads to the formation of the characteristic ketone function of limonaketone in 92% yield. The last step was performed by a deoxygenation in the presence of Zn and gave limonaketone in quantitative yield. The optically pure limonaketone has been efficiently synthesized from limonene and the overall yield was 84%. A molecular electron density theory (MEDT) analysis was carried out by using density functional theory (DFT) calculations at the M06–2X/6–311G(d,p) (LANL2DZ for Zn) level to understand the observed chemoselectivity in the Zn-deoxygenation reaction as well as its corresponding mechanistic pathway.

5-Hydroperoxycarbonylphthalimide: A new reagent for epoxidation

James, Alun P.,Johnstone, Robert A.W.,McCarron, Moya,Sankey, J. Phillip,Trenbirth, Brian

, p. 429 - 430 (1998)

Peroxycarboxylic acids, widely used for epoxidation in industry and general research, have various drawbacks, such as difficulty of preparation in a pure state, cost and the possibly ring-opening of the product epoxides due to acid-catalysed reactions; a new reagent, 5-hydroperoxycarbonylphthalimide, overcomes these problems.

A High Activity Molybdenum containing Epoxidation Catalyst and its Use in Regioselective Epoxidation of Polybutadiene

Gahagan, Michael,Iraqi, Ahmed,Cupertino, Domenico C.,Mackie, Raymond K.,Cole-Hamilton, David J.

, p. 1688 - 1690 (1989)

MoO2Cl2 is a highly active catalyst for the epoxidation of alkenes by ButOOH; for polybutadiene containing cis-1,4-, trans-1,4-, and 1,2-polymerised units, very high selectivity to the backbone double bonds is observed.

Heterogeneous catalysis with an organic-inorganic hybrid based on MoO3chains decorated with 2,2′-biimidazole ligands

Amarante, Tatiana R.,Neves, Patrícia,Almeida Paz, Filipe A.,Gomes, Ana C.,Pillinger, Martyn,Valente, Anabela A.,Gon?alves, Isabel S.

, p. 2214 - 2228 (2021)

The discovery of selective heterogeneous catalytic systems for industrial oxidation processes remains a challenge. Molybdenum oxide-based polymeric hybrid materials have been shown to be oxidation catalysts under mild reaction conditions, although difficulties remain with catalyst recovery/reuse since most perform as homogeneous catalysts or possess low activity. The present study shows that the hybrid material [MoO3(2,2′-biimidazole)]·H2O (1) is a superior catalyst regarding these issues. The structure of1was confirmed (by single crystal and synchrotron X-ray powder diffraction) to comprise one-dimensional chains of corner-sharing {MoO4N2} octahedra. Strong MoO?H-N hydrogen bonds separate adjacent chains to afford parallel channels that are occupied by disordered water molecules. Hybrid1was additionally characterised by FT-IR spectroscopy,1H and13C MAS NMR, scanning electron microscopy and thermogravimetric analysis. The catalytic studies highlighted the versatility of1for oxidation reactions withtert-butylhydroperoxide as oxidant. By complementing with characterisation studies, it was verified that the reaction occurs in the heterogeneous phase, the catalyst has good stability and is recoverableviasimple procedures. The chemical reaction scope covered epoxidation and sulfoxidation, and the substrate scope included biomass-deriveddl-limonene and fatty acid methyl esters to give renewable bio-products, as well as thiophene and thioanisole substrates.

Anchoring of a terpyridine-based Mo(VI) complex on manganese ferrite as a recoverable catalyst for epoxidation of olefins under solvent-free conditions

Fadaei Sarabi, Mahsa,Bezaatpour, Abolfazl,Mahmoudi, Ali

, p. 1597 - 1612 (2021)

A magnetically separable heterogeneous nanocatalyst was obtained by anchoring a terpyridine-based Mo(VI) complex on modified MnFe2O4 nanoparticles and characterized by Fourier transform infrared (FT-IR), X-ray diffraction (XRD) and diffuse reflectance spectroscopies (DRS), transmission electron microscopy (TEM), scanning electron microscopy (SEM), vibrating sample magnetometry (VSM), X-ray photoelectron spectroscopy (XPS) and Brunauer-Emmett-Teller (BET) analysis. The catalytic activity of the supported molybdenum based catalyst was evaluated in the selective epoxidation of various olefins (cyclooctene, limonene, 1-dodecane, 1-heptene, styrene, 1-indene, α-pinene, cyclohexene) with tert-butyl hydroperoxide (TBHP) as an oxidant under solvent-free conditions. This nanocatalyst was easily separated by using an external magnetic field and reused consecutively at least five times with no significant loss in selectivity and catalytic activity. The short reaction time, simple preparation, high conversion, good physicochemical stability and magnetic recycling of the catalysts are beneficial.

Selective epoxidation of (+)-limonene employing methyltrioxorhenium as catalyst

Michel, Typhne,Cokoja, Mirza,Sieber, Volker,Kühn, Fritz E.

, p. 159 - 165 (2012)

This report presents a study of the epoxidation of limonene employing methyltrioxorhenium (MTO) as catalyst. The influence of base ligands, namely t-butylpyridine, 4,4′-dimethyl-2,2′-bipyridine and pyrazole on the catalytic activity was investigated. The choice of the oxidant (H 2O2 in water or H2O2 stabilized by urea) was also examined. The effect of the solvent has been studied in order to determine optimal conditions for the epoxidation of (+)-limonene. The best result was obtained when a molar ratio (+)-limonene:MTO:H2O 2:t-butylpyridine of 100:0.5:10:150 was used at 25 °C in dichloromethane. 1,2-Limonene oxide was formed with 77% yield and 96% selectivity after 1 h with a TOF of ca. 900 h-1.

-

Kropf,Yazdanbakhch

, p. 711 (1977)

-

Evaluation of antiparasitic activity of mentha crispa essential oil, its major constituent rotundifolone and analogues against trypanosoma brucei

De Sousa, Dami?o Pergentino,Lima, Tamires Cardoso,Steverding, Dietmar

, p. 1346 - 1350 (2016)

Considering the pressing need for new drugs to treat sleeping sickness and Nagana disease, Mentha crispa essential oil, its principal constituent rotundifolone, and four related p-menthane-Type monoterpenes (two stereoisomers of limonene epoxide, perillyl alcohol, and perillyl aldehyde) were investigated for their activity against bloodstream forms of Trypanosoma brucei. The general cytotoxicity of the compounds was determined with human myeloid HL-60 cells. The effect of the M. crispa essential oil and the monoterpenes on the growth of parasite and human cells was evaluated in cell cultures with the resazurin viability assay. Of all of the compounds tested, M. crispa essential oil, rotundifolone, and perillyl aldehyde showed the highest trypanocidal activities with 50% growth inhibition (GI50) and minimum inhibitory concentration values of 0.3 μg/ mL and 1 μg/mL, respectively. In contrast, HL-60 cells were considerably less sensitive to the compounds with minimum inhibitory concentration values of 100 μg/mL and GI50 values ranging between 3.4 to 13.8 μg/mL. As a consequence of this, GI50 and minimum inhibitory concentration ratios of cytotoxic to trypanocidal activity (selectivity index) of these three compounds were promising with values of 11-45 and 100, respectively. These results indicate that the p-menthane-Type monoterpenes rotundifolone and perillyl aldehyde are interesting lead candidates for further rational antitrypanosomal drug development.

New poly(organophosphazene) - Supported cobalt or copper (II) catalysts for the oxidation of alkenes

Blaz,Pielichowski

, p. 345/[711]-355/[721] (2008)

Polymer-supported heterogeneous catalysts in form of complexes of poly[bis(pyridine-2-oxy)phosphazene] with cobalt(II) or copper(II) acetate were synthesized. The catalysts were prepared by a three-step reaction procedure. First, poly(dichlorophosphazene) was synthesized by thermal polymerization of cyclic trimer of hexachlorocyclotriphosphazene. In the second stage, the poly(dichlorophosphazene) structure was converted into the 2-hydroxypyridine by a nucleophilic substitution reaction. The last stage of the catalyst synthesis was the reaction of poly[bis(pyridine-2-oxy)phosphazene] with cobalt acetate or copper acetate. FTIR, 31P NMR, AAS, BET, SEM, SEM-EDS and TG were employed for characterization of the obtained catalysts. The complexes were applied as heterogeneous catalysts in oxidation of dodecene, indene, limonene in the presence of molecular oxygen in acetonitrile (as solvent) at 60C, using isobutyraldehyde as an oxygen transfer agent. Oxidation reactions of aliphatic and aromatic hydrocarbons let to formation of epoxides or ketones with good yield and high selectivity.

Solvent-free chromium catalyzed aerobic oxidation of biomass-based alkenes as a route to valuable fragrance compounds

Robles-Dutenhefner, Patricia A.,Brand?o, Bruno B.N.S.,De Sousa, Líniker F.,Gusevskaya, Elena V.

, p. 172 - 178 (2011)

Chromium containing mesoporous molecular sieves MCM-41 were shown to be an efficient heterogeneous catalyst for the liquid-phase aerobic oxidation of various monoterpenic alkenes under mild solvent-free conditions. The material was prepared through a direct hydrothermal method and characterized by ICP-AES, N2 adsorption-desorption, TEM, XRD, SAXS, and H2-TPR techniques. Characterizations suggest that chromium introduced in MCM-41 is essentially incorporated in the silica framework, with no extraframework chromium oxides being detected. Various oxygenated monoterpenoids important for the flavor and fragrance industry were obtained with high combined selectivities (75-92%) at 30-40% substrate conversions. The oxidation of β-pinene led almost exclusively to allylic mono-oxygenated derivatives, whereas limonene and α-pinene gave both epoxides and allylic oxidation products. The catalyst undergoes no metal leaching and can be easily recovered and re-used. A silica-included chromium catalyst prepared through a conventional sol-gel method showed activity comparable with that of Cr-MCM-41; however, selectivity was much lower.

New catalysts for the aerobic selective oxidation of hydrocarbons: Mn(III)- and Co(III)-containing molecular sieves for the epoxidation of alkenes

Raja, Robert,Sankar, Gopinathan,Thomas, John Meurig

, p. 829 - 830 (1999)

Co(III) or Mn(III) ions that replace some 4 atom% of Al(III) sites in microporous aluminophosphate number 36 (AlPO-36) function as catalytically active centres for the production from benzaldehyde of acylperoxy radicals: these, in turn, in dry air (30 bar) convert cyclohexene, pinene, limonene and styrene to their corresponding epoxides and diols.

Olefin epoxidation with tert-BuOOH catalyzed by vanadium polyoxometalate immobilized on ionic liquid-modified MCM-41

Hajian, Robabeh,Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Khosropour, Ahmad Reza

, p. 4134 - 4144 (2011)

Preparation and characterization of vanadium-containing polyphosphomolybdates supported on ionic liquid-modified MCM-41, MCM-41-Im, are reported. The catalyst, [PVMo@MCM- 41-Im], was characterized by elemental analysis, X-ray diffraction, scanning electron microscopy and also FT-IR, and UV-Vis spectroscopic methods. This heterogeneous catalytic system was applied for efficient epoxidation of various olefins in the presence of tert-BuOOH in 1,2-dichloroethane under reflux. The catalyst can be reused several times without apparent loss of its catalytic performance.

Limonene oxyfunctionalization over Cu-modified silicates employing hydrogen peroxide and t-Butyl hydroperoxide: Reaction pathway analysis

Vaschetti, Virginia M.,Cánepa, Analía L.,Barrera, Deicy,Sapag, Karim,Eimer, Griselda A.,Casuscelli, Sandra G.

, (2020)

Limonene oxidation over Cu-nanostructured mesoporous materials was studied. Three solids with different copper content were synthesized employing the template-ion exchange method, and physically-chemically analyzed by a multi-technical characterization. The performance of the molecular sieves as catalysts in the liquid phase oxyfunctionalization of limonene, employing hydrogen peroxide (H2O2) or t-butyl hydroperoxide (TBHP) as oxidants was evaluated. All synthesized Cu-MCM materials were active in the reaction. The obtained results showed that the used oxidant had an important influence on the products distribution under the employed conditions. With H2O2, compounds of high added value such as limonene oxide, carveol and carvone were mainly obtained. Meanwhile, with TBHP, limonene hydroperoxide turned out to be the major product. Finally, a reaction mechanism was proposed for each oxidant.

Catalytic β-bromohydroxylation of natural terpenes: Useful intermediates for the synthesis of terpenic epoxides

Oubaassine, Saadia,K?ckritz, Angela,Eckelt, Reinhard,Martin, Andreas,Ait Ali, Mustapha,El Firdoussi, Larbi

, (2019)

In a one-step procedure, various β-bromoalcohols were synthesized from natural terpenes in good to excellent yields. Using different catalysts, the reaction was carried out at room temperature, with H2O as nucleophile and N-bromosuccinimide as a bromine source under mild reaction conditions. The synthesized β-bromoalcohols were subsequently converted in situ to the corresponding epoxides in good yields.

Oxidation reactions catalyzed by polyoxomolybdate salts

Zhang, Bo,Li, Su,Poethig, Alexander,Cokoja, Mirza,Zang, Shu-Liang,Herrmann, Wolfgang A.,Kuehn, Fritz E.

, p. 587 - 597 (2013)

Ionic compounds containing the polyoxomolybdate anion [Mo6O 19]2- and [(n-C4H9) 4P]+ (tetra-butylphosphonium), [(n-C4H 9)3P(n-C14H29)]+ (tributyl (tetradecyl)phosphonium), [Bmim]+ (1-butyl-3- methylimidazolium) and [Dbmim]+ (1,2-dimethyl-3-butylimidazolium) cations were prepared and characterized, including the determination of three of the solid state structures by singlecrystal X-ray diffraction. These compounds were applied as catalysts for the epoxidation of olefins with urea hydrogen peroxide (UHP) as oxidant in the ionic liquid [Bmim]PF6. Additionally, the oxidation of sulfides to sulfoxides with hydrogen peroxide (H2O2) in several solvents was investigated. The polyoxomolybdate catalysts showed a good performance for epoxidation of olefins as well as for oxidation of sulfides. Furthermore, the catalysts can be recycled several times in oxidation reactions. We present this methodology for the oxidation reaction in a simple, economically, technically, and environmentally benign manner.

New Mo(II) complexes in MCM-41 and silica: Synthesis and catalysis

Saraiva, Marta S.,Fernandes, Cristina I.,Nunes, Teresa G.,Nunes, Carla D.,Calhorda, Maria José

, p. 443 - 452 (2014)

The new complexes [MoI2(CO)3(L1)] (1) and [MoI2(CO)3(L2)] (2) were prepared from reaction of [MoI2(CO)3(NCMe)2] with the ligands 2-(2′-hydroxyphenyl)imidazoline (L1), and 2-(2′- hydroxyphenyl) benzimidazole (L2). These complexes were immobilized in MCM-41 and in silica gel, by grafting (3- chloropropyl)trimethylsilane on the surface of the materials and allowing it to react with [MoI2(-CO) 3(L1)] (1) or [MoI2(CO)3(L 2)] (2). All the molybdenum derivatives were characterized by NMR and FTIR spectroscopies, which showed coordination of L1 and L 2 in neutral form. The structure of the MCM materials was analyzed by powder X-ray diffraction and nitrogen adsorption isotherms. The catalytic activity of the complexes and materials was tested in several substrates (cis-cyclooctene, styrene, 1- octene, R-(+)limonene, geraniol, cis-hex-3-en-1-ol and trans-hex-2-en-1-ol), using tert-butylhydroperoxide (TBHP) as oxidant. Complexes 1 and 2 were in general the more active catalysts and 100% selective towards the epoxide of cis-cyclooctene. Complex 1 immobilized in silica (Si-Pr-1) was the best material, showing higher conversion than 1 in the oxidation of R-(+)limonene, with comparable selectivity towards the ring epoxide.

Synthesis and catalytic properties in olefin epoxidation of octahedral dichloridodioxidomolybdenum(VI) complexes bearing N,N-dialkylamide ligands: Crystal structure of [Mo2o4(μ2-o)CI2(dmf) 4]

Gago, Sandra,Neves, Patricia,Monteiro, Bernardo,Pessego, Marcia,Lopes, Andre D.,Valente, Anabela A.,Almeida Paz, Filipe A.,Pillinger, Martyn,Moreira, Jose,Silva, Carlos M.,Goncalves, Isabel S.

, p. 4528 - 4537 (2009)

The catalytic performance of the complexes [MoO2Cl 2(L)2] [L = N,N-dimethylformamide (dmf), N,N-dimethylacetamide (dma), N,N-dimethylpropionamide (dmpa), N,N-diethylformamide (def) and N,N-diphenylformamide (dpf)] was examined in the epoxidation of cis-cyclooctene with ieri-butyl hydroperoxide (tbhp) at 55 °C and in the absence of a cosolvent. The complexes showed high turnover frequencies in the range of 561-577 molmolMo-1h -1r giving the epoxide as the only product in 298 % yield after 6 h. The reaction rates decreased significantly in consecutive runs carried out by recharging the reactors with olefin and oxidant. On the basis of the IR spectroscopic characterisation of the solids recovered at the end of the catalytic reactions, the decrease in activity is attributed to the formation of dioxido(n-oxido)-molybdenum(VI) dimers. Accordingly, the treatment of [Mo0 2Cl2(dmf)2] with an excess amount of tbhp led to the isolation of [Mo204(μ2-0)Cl 2(dmf)4], which was characterised by single-crystal X-ray diffraction and found to exhibit a catalytic performance very similar to that found in the second runs for the mononuclear complexes. The kinetics of the reaction of [Mo02Cl2(dmf)2] with tbhp was further examined by UV/Vis spectroscopy, allowing rate constants and activation parameters to be determined. For the dpf adduct, the effect of different solvents on cyclooctene epoxidation and the epoxidation of other olefins, namely, (R)-(+)-limonene,αpinene and norbornene, were investigated. Wiley-VCH Verlag GmbH & Co. KGaA.

Oxygen Atom Transfer Mechanism for Vanadium-Oxo Porphyrin Complexes Mediated Aerobic Olefin Epoxidation

Han, Qi,Huang, Jia-Ying,Ji, Hong-Bing,Liu, Xiao-Hui,Tao, Lei-Ming,Xue, Can,Yu, Hai-Yang,Zhou, Xian-Tai,Zou, Wen

supporting information, p. 115 - 122 (2021/12/04)

The development of catalytic aerobic epoxidation by numerous metal complexes in the presence of aldehyde as a sacrificial reductant (Mukaiyama epoxidation) has been reported, however, comprehensive examination of oxygen atom transfer mechanism involving free radical and highly reactive intermediates has yet to be presented. Herein, meso-tetrakis(pentafluorophenyl) porphyrinatooxidovanadium(IV) (VOTPFPP) was prepared and proved to be efficient toward aerobic olefin epoxidation in the presence of isobutyraldehyde. In situ electron paramagnetic resonance spectroscopy (in situ EPR) showed the generation, transfer pathways and ascription of free radicals in the epoxidation. According to the spectral and computational studies, the side-on vanadium-peroxo complexes are considered as the active intermediate species in the reaction process. In the cyclohexene epoxidation catalyzed by VOTPFPP, the kinetic isotope effect value of 1.0 was obtained, indicating that epoxidation occurred via oxygen atom transfer mechanism. The mechanism was further elucidated using isotopically labeled dioxygen experiments and density functional theory (DFT) calculations.

A sustainable approach towards solventless organic oxidations catalyzed by polymer immobilized Nb(V)-peroxido compounds with H2O2 as oxidant

Ahmed, Kabirun,Gogoi, Sandhya Rani,Islam, Nashreen S.,Saikia, Gangutri,Sultana, Sazida Yasmin,Talukdar, Hiya

, (2021/11/16)

New heterogeneous catalysts comprising of peroxidoniobium(V) complexes immobilized on amino acid grafted cross-linked poly(styrene-divinylbenzene) resin has been developed. Results of FTIR, Raman, NMR, XPS, XRD, EDX, SEM, BET, TGA, and elemental analysis confirmed the successful anchoring of triperoxidoniobium(V), [Nb(O2)3]? species to the host polymer via the pendant amino acid groups. The supported catalysts exhibited excellent performance in epoxidation of styrene and a range of cyclic and terpenic compounds under environmentally acceptable solvent-free condition, with aqueous H2O2 as oxidant. The catalytic protocols provided excellent conversion to the desired epoxide (up to 100%) with selectivity > 99%, TON as high as 1000, and high H2O2 utilization efficiency (92–97%). Moreover, the catalysts efficiently facilitated chemoselective solvent-free oxidation of a variety of thioethers to sulfones at room temperature. Simple operational strategy, easy recyclability for multiple reaction cycles with the consistent activity-selectivity profile are the additional significant attributes of the developed catalytic processes.

Catalytic efficacy of 2,2′-bipyridine cobalt(II) complex: Hydrothermal synthesis, x-ray structure and aerobic epoxidation of alkenes

Bera, Rajesh

, p. 10 - 14 (2021/01/06)

A mononuclear cobalt(II) complex, [Co(bpy)2(NO3)](NO3)·3H2O (1) (bpy = 2,2′-bipyridine) has been synthesized hydrothermally and the crystal structure was characterized by X-ray crystallography. Complex 1 is capable of activating aerobic oxygen at atmospheric pressure. [Co(bpy)2(NO3)](NO3)·3H2O (1) was used as an active catalyst for the aerobic epoxidaion of various alkenes with isobutyraldehyde as co-reductant in acetonitrile medium. Complex 1 catalyzes the epoxidaion reaction efficiently, which reflected in high yield of products with desired selectivity.

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