62875-10-9

Basic information

• Product Name: Oxiranemethanol, 3-[2-(3,3-dimethyloxiranyl)ethyl]-3-methyl-
• CAS NO: 62875-10-9
• Molecular Formula: C10H18O3
• Molecular Weight: 186.251
• Mol File: 62875-10-9.mol

Chemical Properties

• CAS DataBase Reference: Oxiranemethanol, 3-[2-(3,3-dimethyloxiranyl)ethyl]-3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranemethanol, 3-[2-(3,3-dimethyloxiranyl)ethyl]-3-methyl-(62875-10-9)
• EPA Substance Registry System: Oxiranemethanol, 3-[2-(3,3-dimethyloxiranyl)ethyl]-3-methyl-(62875-10-9)

Safety Data

• Hazardous Substances Data: 62875-10-9(Hazardous Substances Data)

Upstream product

• 106-24-1 Geraniol 
• 106-25-2 Nerol 
• 624-15-7 geraniol 

Relevant articles and documents

Can Br?nsted acids catalyze the epoxidation of allylic alcohols with H2O2? With a little help from the proton, the H3PMo12O40 acid did it and well

In this work, we have explored the catalytic activity of typical Br?nsted acid in epoxidation reactions of terpene alcohols with hydrogen peroxide. Keggin heteropolyacids (HPAs) (i.e., H3PW12O40, H3PMo12O40, and H4SiW12O40) were compared to the common Br?nsted acids (i.e., sulfuric, and p-toluenesulfonic acids) in epoxidation reactions of nerol, the model molecule selected. The effects of the main reaction variable, such as temperature, time, load and sort of acid catalyst were evaluated. Among the catalysts investigated, H3PMo12O40 was the most active and selective catalyst toward epoxide nerol, the goal product. The highest conversion obtained was 99%, with a selectivity of 97% towards nerol epoxide. A discussion of the reaction mechanism was performed as the basis of experimental results and acidity properties of the catalysts. A comparison with a non-protic catalyst (i.e., Na3PMo12O40) allowed demonstrate that both Molybdenum and protons present in the H3PMo12O40 are the main active sites in this epoxidation reaction.

Dysprosium-doped zinc tungstate nanospheres as highly efficient heterogeneous catalysts in green oxidation of terpenic alcohols with hydrogen peroxide

A green route to oxidize terpenic alcohols (nerol and geraniol) with H2O2over a solid catalyst was developed. The Dy-doped ZnWO4catalyst was synthesized by coprecipitation and microwave-assisted hydrothermal heating, containing different dysprosium loads. All the catalysts were characterized through infrared spectroscopy, powder X-ray diffraction, surface area and porosimetry, transmission electronic microscopy image, andn-butylamine potentiometric titration analyses. The influence of main reaction parameters such as temperature, the stoichiometry of reactants, loads, and catalyst nature was assessed. ZnWO42.0 mol% Dy was the most active catalyst achieving the highest conversion (98%) and epoxide selectivity (78%) in nerol oxidation. The reaction scope was extended to other terpenic alcohols (i.e., geraniol, borneol, and α-terpineol). The highest activity of ZnWO42.0 mol% Dy was assigned to the lower crystallite size, higher surface area and pore volume, higher acidity strength and the greatest dysprosium load.

Unraveling the role of the lacunar Na7PW11O39 catalyst in the oxidation of terpene alcohols with hydrogen peroxide at room temperature

In this work, we have assessed the activity of various Keggin heteropolyacid (HPA) salts in a new one-pot synthesis route of valuable products, which were obtained from the oxidation of terpenic alcohols (i.e., aldehyde, epoxide, and diepoxide), using a green oxidant (i.e., hydrogen peroxide) at mild conditions (i.e., room temperature). Lacunar Keggin HPA sodium salts were the goal catalysts investigated in this reaction. Starting from the HPAs (H3PW12O40, H3PMo12O40, and H4SiW12O40), we synthesized lacunar sodium salts (Na7PW11O39, Na7PW11O39 and Na8SiW11O39) and a saturated salt (Na3PW12O40). All of them were investigated in oxidation reactions in a homogeneous phase with nerol as a model molecule. Na7PW11O39 was the most active and selective towards the oxidation products. All the catalysts were characterized by FT-IR, TG/DSC, BET, XRD, and SEM-EDS analyses and potentiometric titration. The main reaction parameters were assessed. Geraniol, α-terpineol, β-citronellol and borneol were also successfully oxidized. Special attention was dedicated to correlating the composition and properties of the catalysts with their activity.

An immobilized imidazolyl manganese porphyrin for the oxidation of olefins

A new catalytic system based on an immobilized imidazolyl manganese porphyrin for the oxidation of olefins is presented. Merrifield resin (MR) and functionalized silica gel (SG) were chosen as supports. The results indicate that the MR system shows high reaction rates, high efficiency with hydrogen peroxide as oxidant and good recyclability up to four times, without a dramatic loss in the catalytic efficiency. The catalytic behavior seems to be strongly influenced by the immobilization reaction conditions. The oxidation reactions performed for cis-cyclooctene, styrene, cyclohexene and geraniol give the corresponding epoxides, with very high selectivity, when the MR system is used. Some considerations concerning the high efficiency of the MR system are put forward.

Mo(II) complexes of 8-aminoquinoline and their immobilization in MCM-41

Two new Mo(II) complexes [MoBr(η3-C3H 5)(CO)2(8-aq)] (1) and [MoI2(CO) 3(8-aq)] (2) containing the bidentate 8-aminoquinoline ligand (8-aq) were synthesized and characterized. They were immobilized in MCM-41. A 3-iodopropyltrimethoxysilane spacer reacted both with the surface, through the silane, and through the other end, with the coordinated 8-aq of complexes 1 and 2, leading to an immobilized form of the complex (MCM-Pr-1,2). In an alternative route, 8-aq reacted with 3-iodopropyltrimethoxysilane to form a new ligand L1, which could be supported in the MCM-41 and then react with the metal precursors to afford (MCM-L1-1,2). The complexes and the materials were characterized using FTIR and NMR spectroscopies, and the structure of the materials was checked with powder X-ray diffraction and nitrogen adsorption isotherms. The first synthetic procedure was less efficient in terms of metal load inside the channels of the materials. The complexes and the new materials were tested as catalytic precursors in the epoxidation of cis-cycloctene, styrene, 1-octene, R-(+)limonene, geraniol, cis-3-hexene-1-ol and trans-2-hexene-1-ol, using tert-butylhydroperoxide (TBHP) as oxidant. Although almost all the catalysts were 100% selective toward the epoxide, the conversions were in general poor. The best catalyst was complex 1, but the conversions dropped after immobilization. Conversions could be a bit improved by a careful choice of reaction conditions, the most effective being the absence of added solvent (the substrate acted as solvent).

Mono-substituted silicotungstates as active catalysts for sustainable oxidations: Homo- and heterogeneous performance

A series of tetrabutylammonium (TBA) salts of the transition metal mono-substituted silicotungstates [SiW11M(H2O)O 39]n-, M = CoII, FeIII, Mn III, (SiW11M) were explored as homogeneous catalysts for the oxidation of geraniol and styrene with H2O2. The most active homogeneous catalysts (SiW11Co and SiW11Fe) were immobilized onto an amine-functionalized SBA-15 (aptesSBA-15) and the resulting composites were characterized using several techniques (FT-IR, FT-Raman, UV-Vis/DRS, elemental analysis, powder XRD, SEM and N2 adsorption-desorption isotherms). The catalytic performance of the new composites SiW11Co@aptesSBA-15 and SiW11Fe@aptesSBA-15 was investigated under similar experimental conditions to those used for homogeneous counterparts. 2,3-Epoxygeraniol and benzaldehyde were the main products obtained from geraniol and styrene oxidation, respectively, for all the catalysts. SiW11Co and SiW11Co@aptesSBA-15 showed to be the most active catalysts for the oxidation of geraniol and styrene. The recyclability of the composite SiW11Co@aptesSBA-15 was investigated for three reaction cycles. The stability of the composites was confirmed using several techniques after catalytic cycles.

Peroxometalates immobilized on magnetically recoverable catalysts for epoxidation

Magnetically separable catalysts were prepared and employed for the epoxidation of olefins with hydrogen peroxide. In all cases the magnetic core was firstly covered with a silica layer to prevent iron ion-initiated decomposition of hydrogen peroxide. The catalytic active species, an ionic liquid-type peroxotungstate, was then immobilized either by hydrogen bonding (catalyst 1) or by covalent SiO linkage (catalyst 2). In addition to a thorough characterization by FT-IR, XRD, NMR, DRIFT, XPS, and TEM, the catalytic potential was evaluated in the epoxidation of a variety of olefins as well as allylic alcohols. Both catalysts showed essentially a constant activity after at least ten consecutive cycles. On the basis of the research above, a new type of magnetically separable catalyst was constructed by immobilization of lacunary-type phosphotungstate by hydrogen bonding between the sulfonate anion and silanol group on the surface of the core-shell magnetic nanoparticles. After the detailed characterization, the catalyst was used in the epoxidation of a variety of olefins and allylic alcohols and was found to possess high activity, selectivity towards epoxides, and a constant activity after at least ten catalytic recycles without solvent.

Iron(III)-substituted polyoxotungstates immobilized on silica nanoparticles: Novel oxidative heterogeneous catalysts

Silica nanoparticles supporting polyoxometalates (POMs), namely an iron(III) mono-substituted Keggin-type polyoxotungstate of formula α-[PW11FeIII(H2O)O39] 4- and a sandwich-type tungstophosphate with the formula B-α-[(PW9O34)2FeIII 4(H2O)2]6- were synthesized. The POM/SiO2 nanocomposites were obtained by alkaline hydrolysis of tetraethoxysilane using a reverse micelle and sol-gel technique. The spectroscopic studies suggest that the POMs were successfully immobilized on the silica nanoparticles. The catalytic activity of POM/SiO2 nanomaterials was tested in the epoxidation of geraniol using H 2O2 as oxygen donor. The α-[PW11Fe III(H2O)O39]4-/SiO2 nanocomposite was the most efficient catalyst with high geraniol conversion and good regioselectivity for 2,3-epoxygeraniol.

Synthesis of epoxides catalyzed by a halide-free reaction-controlled phase-transfer catalytic system: [(CH3(CH2) 17)2N(CH3)2]3[PW 4O32]/H2O2/Dioxan/Olefin

The epoxidation of alkenes was successfully catalyzed by a recyclable catalytic system: [(CH3(CH2)17) 2N(CH3)2]3[PW4O 32]/H2O2/dioxan/olefin. This new catalytic system is not only capable of catalyzing homogeneous epoxidation of alkenes with a unique reaction-controlled phase-transfer character, but also avoids the use of chlorinated solvents. The reactions were conducted in a biphasic mixture of aqueous H2O2/dioxan, and many kinds of alkenes could be efficiently converted to the corresponding epoxides in high yields. Both new and used [(CH3(CH2)17)2N(CH 3)2]3[PW4O32] catalyst was characterized by 31P magic angle spin NMR, and IR. CSIRO 2009.

Oxidation of geraniol and other substituted olefins with hydrogen peroxide using mesoporous, sol-gel-made tungsten oxide-silica mixed oxide catalysts

The preparation of a series of mesoporous tungsten oxide-silica mixed oxides by sol-gel methods under basic conditions is reported. Surface modification with methyl and 3-chloropropyl groups is possible in an amount between 10 and 40 mol% with respect to the silane precursor. The amount of polar organic functional groups controls the surface area, the porosity, and the catalytic activity of the solids in the oxidation of different substrates with hydrogen peroxide. The oxidation of geraniol is studied in detail. The catalysts are active and produce epoxides in good yields. The latter are influenced by the presence of polar organic groups. The preparation method allows the preparation of catalysts that are resistant to leaching and can be recycled several times without appreciable loss of activity.