2979-30-8

Usage

InChI:InChI=1/C9H18O2/c1-7(2)11-9-6-4-3-5-8(9)10/h7-10H,3-6H2,1-2H3

Upstream product

• 64672-72-6 2-(dimethoxymethylidene)propanedinitrile 
• 286-20-4 cyclohexane-1,2-epoxide 
• 67-63-0 isopropyl alcohol 
• 110-83-8 cyclohexene 
• 24796-87-0 2-bromo-cyclohexanol 
• 286-20-4 cyclohexene oxide 

Downstream Products

• 134108-70-6 (1R,2R)-2-Isopropoxy-cyclohexanol 
• 134108-80-8 Butyric acid (1S,2S)-2-isopropoxy-cyclohexyl ester 
• 134070-89-6 Butyric acid (1S,2S)-2-isopropoxy-cyclohexyl ester 

Relevant academic research and scientific papers

Cross-linked poly(N-vinylpyrrolidone)-titanium tetrachloride complex: A novel stable solid TiCl4 equivalent as a recyclable polymeric Lewis acid catalyst for regioselective ring-opening alcoholysis of epoxides

Cross-linked poly(N-vinylpyrrolidone) resin beads were prepared as macromolecular ligand precursors by suspension copolymerization of N-vinyl-2-pyrrolidone and N,N′-methylenebisacrylamide (MBA) as a crosslinking agent in water. Subsequently, the resulting polymer carrier precursor was readily combined with titanium tetrachloride to form a stable polymeric coordination complex (PNVP/TiCl4), and this novel stable TiCl4 equivalent evaluated as a heterogeneous and reusable solid Lewis acid catalyst for the regio-and stereoselective nucleophilic ring opening of various epoxides with various alcohols to prepare β-alkoxy alcohols in excellent yields without generating any waste. The MBA-cross-linked PNVP and resultant catalyst were characterized by Fourier transform infrared spectroscopy (FT–IR), field-emission scanning electron microscope (FE–SEM), energy dispersive X-ray (EDX), inductively coupled plasma (ICP), and thermogravimetric analysis (TGA) techniques. Moreover, the catalyst is very stable, easily separated, and reused at least five times without significant loss of activity. In terms of scope, yields, the amount of catalyst used, and reaction time, the PNVP-TiCl4 complex catalyst is an improvement over previously reported heterogeneous catalysts for ring opening of epoxides methods. Further, the experimental outcome revealed that using the copolymer beads as carriers with a high percentage of crosslinking and the high mesh size leads had an adverse effect on the reaction rate.

MBA-cross-linked poly(N-vinyl-2-pyrrolidone)/ferric chloride macromolecular coordination complex as a novel and recyclable Lewis acid catalyst: Synthesis, characterization, and performance toward for regioselective ring-opening alcoholysis of epoxides

A novel macromolecular-metal coordination complex, MBA-cross-linked PNVP/FeCl3 material was fabricated by immobilization of water intolerant ferric chloride onto the porous cross-linked poly(N-vinyl-2-pyrrolidone) carrier beads as a macromolecular ligand or carrier which was prepared by suspension free-radical copolymerization of N-vinyl-2-pyrrolidone (NVP) and N,N′-methylene bis-acrylamide (MBA) as a crosslinking agent in water. The obtained PNVP/FeCl3 was characterized by UV/vis and FT-IR spectroscopies, TGA, FE-SEM, EDX, and ICP techniques. This heterogenized version of ferric chloride is a convenient and safe alternative to highly water intolerant ferric chloride. The catalytic performance of (PNVP/FeCl3) as an efficient and recyclable polymeric Lewis acid catalyst was appropriately probed in the regio-and stereoselective nucleophilic ring opening of various epoxides with various alcohols in excellent yields with TOF up to 182.48 h?1 without generating any waste. The activity data indicate that this heterogeneous catalyst is very active and could be easily recovered, and reused at least six times without appreciable loss of activity indicating its stability under experimental conditions.

Lead-Free Cs3Bi2Br9 Perovskite as Photocatalyst for Ring-Opening Reactions of Epoxides

Herein, an innovative approach was developed by using stable, lead-free halide perovskite for solar-driven organic synthesis. The ring-opening reaction of epoxides was chosen as a model system for the synthesis of value-added β-alkoxy alcohols, which require energy-intensive process conditions and corrosive, strong acids for conventional synthesis. The developed concept included the in situ preparation of Cs3Bi2Br9 and its simultaneous application as photocatalyst for epoxide alcoholysis under visible-light irradiation in air at 293 K, with exceptional high activity and selectivity ≥86 % for β-alkoxy alcohols and thia-compounds. The Cs3Bi2Br9 photocatalyst exhibited good stability and recyclability. In contrast, the lead-based perovskite showed a conversion rate of only 1 %. The origin of the unexpected catalytic behavior was attributed to the combination of the photocatalytic process and the presence of suitable Lewis-acidic centers on the surface of the bismuth halide perovskite photocatalyst.

Synthesis and structure of an air-stable bis(pentamethylcyclopentadienyl) zirconium pentafluorbezenesulfonate and its application in catalytic epoxide ring-opening reactions

An air-stable mononuclear complex of bis(pentamethylcyclopentadienyl) zirconium pentafluorbezenesulfonate was successfully synthesized by treating C6F5SO3Ag with [(CH3)5Cp]2ZrCl2, which showed the cationic uninuclear structure of [{(CH3)5Cp}2Zr(CH3CN)2(H2O)][OSO2C6F5]2·CH3CN (1) confirmed by the X-ray analysis. Complex 1 was also characterized by other techniques and found to have the good nature of air-stability, water tolerance, thermally-stability and strong Lewis-acidity. Moreover, the complex showed high catalytic activity and recyclability in catalytic epoxide ring-opening reactions by amines or alcohols. This catalytic system affords a simple and efficient approach for synthesis of β-amino alcohols or β-alkoxy alcohols.

Zirconium triflate grafted on SBA-15 as a highly efficient solid acid catalyst for ring opening of epoxides by amines and alcohols

Metal (Al, Ti, Zr) triflate grafted mesoporous SBA-15 (AlTf/S, TiTf/S, ZrTf/S) samples were synthesized as inexpensive solid acid materials by a simple one-pot-two-step synthesis methodology. These materials were characterized by X-ray diffraction, N2-sorption, thermogravimetric analysis, Fourier transform infrared spectroscopy (FT-IR), in-situ pyridine FT-IR spectroscopy, and elemental analysis. ZrTf/S was found to be a highly efficient and reusable solid acid catalyst for ring opening of epoxides with amines and alcohols and produced β-amino alcohols and β-alkoxy alcohols respectively under ambient reaction conditions. The ZrTf/S catalyst showed the highest activity, which was attributed to its high acidity compared with that of the Ti and Al containing samples.

A highly efficient protocol for regioselective ring-opening of epoxides with alcohols, water, acetic acid, and acetic anhydride catalyzed by SbF3

SbF3as an efficient catalyst has been used for regioselective alcoholysis, acetolysis and hydrolysis of epoxides to the corresponding β-alkoxy, β-acetoxy alcohols, and 1,2-diols in high to excellent yields. This study also represents a convenient synthesis of vic-diacetates from ring-opening of epoxides with acetic anhydride.

Enhanced metal loading in SBA-15-type catalysts facilitated by salt addition: Synthesis, characterization and catalytic epoxide alcoholysis activity of molybdenum incorporated porous silica

We report a novel method to increase the metal loading in SBA-15 silica matrix via direct synthesis. It was demonstrated through the synthesis and characterization of a series of molybdenum containing SBA-15 mesoporous silica catalysts prepared with and without diammonium hydrogen phosphate (DHP) as an additive. Catalysts prepared with DHP show a 2-3 times increase in incorporation of molybdenum in the silica matrix and pore size enlargement. The synthesized catalysts were characterized using nitrogen sorption, X-ray diffraction (XRD), Raman spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma-optical emission spectroscopy (ICP-OES). The catalytic activity of catalysts prepared with DHP for alcoholysis of epoxides was superior than the catalyst prepared without DHP. Alcoholysis of epoxides was demonstrated for a range of alcohols and epoxides under ambient conditions in as little as 30 min with high selectivity.

Molybdenum-catalysed oxidation of cyclohexene with hydrogen peroxide in the presence of alcohols and X-ray structures of octamolybdate [C 4mim]4[Mo8O26] and tetraperoxodimolybdate [Htmpy]2[{MoO(O2)2} 2(μ-O)] complexes

The direct formation of a β-alcoxyalcohol from the corresponding olefin was investigated through the study of the oxidation of cyclohexene with hydrogen peroxide, as test reaction, catalysed by commercially available MoO3 in the presence of alcohols. The formation of the corresponding β-alcoxycyclohexanol was favourable in the order Me > Et > iPr > tBu, reaching approximately no yield for tBuOH. In this reaction, the lack of selectivity was due to the simultaneous formation of cyclohexane-1,2-diol by epoxide hydrolysis, a reaction that it is competitive with respect to the epoxide ring-opening reaction by the alcohol. In order to decrease the cyclohexane-1,2-diol yield, by preventing the hydrolysis reaction, several strategies were analysed and discussed. In particular, 2-methoxycyclohexanol was obtained with high yields and 99% selectivity by using as catalyst the [C4mim]4[Mo 8O26] complex (C4mim = 1-butyl-3- methylimidazolium). The structure of the latter octamolybdate and also that of the tetraperoxodimolybdate [Htmpy]2[{MoO(O2) 2}2(μ-O)] (tmpy = 2,4,6-trimethylpyridine) complex were determined by X-ray crystallography. The latter complex shows a μ2-oxygen bridging atom and two μ2- κ2-κ1-peroxo bridging ligands. This overall coordination assembly is unprecedented for binuclear molybdenum complexes.

CuO/SiO2: A simple and efficient solid acid catalyst for epoxide ring opening

A cheap, non toxic, easy to prepare and easy to use supported CuO material has shown to be a very effective catalyst for the alcoholysis of epoxides giving β-alkoxyalcohols in very good yield without generating any waste. The catalyst is heterogeneous in nature and can be reused without any reactivation treatment. The Royal Society of Chemistry.

Mild organic ammonium tribromide-mediated regioselective ring opening of epoxides with alcohols, water, acetic anhydride, and amines under solvent-free reaction conditions

Organic ammonium tribromide (OATB), N-methylpyrrolidine-2-one hydrotribromide (MPHT) was found to be an efficient catalyst for the regioselective ring opening of epoxides with various nucleophiles under solvent free conditions. This procedure occurs under neutral and mild reaction conditions with out adding any additive and afforded high yields of products.