6387-89-9

Usage

Uses

Used in Paint Industry:
2-Oxiranemethanol,2-acetate is used as a reactive diluent for high viscosity epoxy resins in the formulation of paints. Its role is to reduce the viscosity of the epoxy resins, making them easier to apply and work with, while also maintaining the desired properties of the final paint product.
Used in Ink Industry:
In the ink industry, 2-Oxiranemethanol,2-acetate is used as a reactive diluent for epoxy resins in ink formulations. This helps in achieving the right consistency and flow properties for the ink, ensuring a smooth application and improved print quality.
Used in Adhesive Industry:
2-Oxiranemethanol,2-acetate is used as a reactive diluent in the formulation of adhesives, particularly epoxy-based adhesives. Its addition helps in reducing the viscosity of the adhesive, allowing for easier application and improved bonding properties.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-Oxiranemethanol,2-acetate is utilized in the synthesis of various chemical compounds and pharmaceutical products. Its reactivity and unique properties make it a valuable intermediate in the production of certain drugs and medicinal compounds.
Used in Coating Systems:
2-Oxiranemethanol,2-acetate is employed in the development of coating systems, where it serves as a reactive component that can improve the adhesion, durability, and overall performance of the coating. Its presence in the coating formulation can lead to enhanced protection and longer-lasting coatings.

InChI:InChI=1/C5H8O3/c1-4(6)7-2-5-3-8-5/h5H,2-3H2,1H3

Upstream product

• 79-21-0 peracetic acid 
• 591-87-7 Allyl acetate 
• 463-51-4 Ketene 
• 556-52-5 oxiranyl-methanol 
• 127-08-2 potassium acetate 
• 106-89-8 epichlorohydrin 
• 24573-30-6 3-chloro-2-hydroxy-1-propyl acetate 
• 75-36-5 acetyl chloride 
• 64-19-7 acetic acid 
• 127-09-3 sodium acetate 
• 141-52-6 sodium ethanolate 
• 108-24-7 acetic anhydride 
• 108-05-4 vinyl acetate 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 22741-52-2 1-tert-butylamino-2,3-dihydroxypropane 
• 121485-48-1 4-acetoxymethyl-3-phenyl-oxazolidin-2-one 
• 4152-39-0 1-O-acetyl-3-O-benzylpropane-1,2,3-triol 
• 556-52-5 oxiranyl-methanol 
• 19405-98-2 (S)-β-acetoxy-γ-butyrolactone 
• 592-20-1 Acetol acetate 
• 1260495-17-7 2-hydroxy-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propyl acetate 
• 1351288-29-3 CF₃O₃S^(1-)*C₂₄H₃₁N₂O₂⁽¹⁺⁾ 
• 105-70-4 2-hydroxypropane-1,3-diyl diacetate 
• 102-62-5 diacetin 
• 57044-25-4 (R)-oxiranemethanol 
• 60456-23-7 (S)-oxiranemethanol 
• 70445-33-9 1-O-(2-ethylhexyl)glycerin 

Relevant academic research and scientific papers

3-(Acyloxy)propanolamines: agents with β-adrenergic blocking activity

A series of totally aliphatic 3-(acyloxy)propanolamine derivatives were prepared and their pA2-values were determined employing the guinea-pig atrium.Compounds, with an acetyl or methyl succinoyl half ester moiety showed a pronounced β1-adrenergic blocking activity.Keywords: 3-(acyloxy)propanolamines / β1-adrenergic blocking activity

Highly selective and efficient olefin epoxidation with pure inorganic-ligand supported iron catalysts

Over the past two decades, there have been major developments in the transition iron-catalyzed selective oxidation of alkenes to epoxides; a common structure found in drug, isolated natural products, and fine chemicals. Many of these approaches have enabled highly efficient and selective epoxidation of alkenes via the design of specialized ligands, which facilitates to control the activity and selectivity of the reactions catalyzed by iron atom. Herein, we report the development of the olefin epoxidation with inorganic-ligand supported iron-catalysts using 30% H2O2 as an oxidant, and the mechanism is similar to iron-porphyrin type. With the catalyst 1, (NH4)3[FeMo6O18(OH)6], various aromatic and aliphatic alkenes were successfully transformed into the corresponding epoxides with excellent yields as well as chemo- and stereo-selectivity. This catalytic system possesses the advantages of being able to avoid the use of expensive, toxic, air/moisture sensitive and commercially unavailable organic ligands. The generality of this methodology is simple to operate and exhibits high catalytic activity as well as excellent stability, which gives it the potential to be used on an industrial scale, and maybe opens a way for the catalytic oxidation reaction via inorganic-ligand coordinated iron catalysis.

Poly(Alkyl Glycidate Carbonate)s as Degradable Pressure-Sensitive Adhesives

Insertion of CO2 into the polyacrylate backbone, forming poly(carbonate) analogues, provides an environmentally friendly and biocompatible alternative. The synthesis of five poly(carbonate) analogues of poly(methyl acrylate), poly(ethyl acrylate), and poly(butyl acrylate) is described. The polymers are prepared using the salen cobalt(III) complex catalyzed copolymerization of CO2 and a derivatized oxirane. All the carbonate analogues possess higher glass-transition temperatures (Tg=32 to ?5 °C) than alkyl acrylates (Tg=10 to ?50 °C), however, the carbonate analogues (Td≈230 °C) undergo thermal decomposition at lower temperatures than their acrylate counterparts (Td≈380 °C). The poly(alkyl carbonates) exhibit compositional-dependent adhesivity. The poly(carbonate) analogues degrade into glycerol, alcohol, and CO2 in a time- and pH-dependent manner with the rate of degradation accelerated at higher pH conditions, in contrast to poly(acrylate)s.

Continuous-Flow Synthesis of (R)-Propylene Carbonate: An Important Intermediate in the Synthesis of Tenofovir

(R)-Propylene carbonate is an important intermediate in the synthesis of tenofovir pro-drugs such as tenofovir alafenamide fumarate (TAF) and tenofovir diisoproyl fumarate (TDF). Independent of the pro-drug type, tenofovir presents a chiral secondary hydroxy derivative, which can be obtained directly from (R)-propylene carbonate. Herein, we report our chemo-enzymatic continuous-flow strategy towards (R)-propylene carbonate starting from a very cheap and renewable raw material, glycerol. We were able to synthesize (R)-propylene carbonate in seven continuous-flow steps, starting from glycerol, in good-to-excellent yields (66–93 %) and excellent selectivity (E > 200).

Synthesis and enzymatic resolution of racemic 2,3-epoxy propyl esters obtained from glycerol

A method is described for the synthesis of (±)-2,3-epoxy propyl esters from glycerol, involving reaction of epichlorohydrin with sodium or potassium salts of carboxylic acids in the presence of TBAB as catalyst, with moderate to excellent yields. Kinetic resolution of glycidyl butyrate by lipase of Thermomyces lanuginosa has been achieved with remarkable enantiomeric excess (ee >99%) using 1,4-dioxane as a co-solvent in pure buffer solution (30 and 50 °C, pH = 7.0).

Composites of [γ-H2PV2W10O40]3- and [α-SiW12O40]4- supported on Fe2O3 as heterogeneous catalysts for selective oxidation with aqueous hydrogen peroxide

Composites of [γ-H2PV2W10O40]3- and [α-SiW12O40]4- supported on Fe2O3 (PV2-SiW12/Fe2O3, in particular, the molar ratio of PV2/SiW12 = 1/1) could act as effective and reusable heterogeneous catalysts for selective oxidation with aqueous hydrogen peroxide. In the presence of PV2-SiW12/Fe2O3, various kinds of organic substrates such as alkenes, sulfides, arenes, and alkanes could selectively be converted into the corresponding oxygenated products in moderate to high yields. The observed catalyses for the present oxidations were intrinsically heterogeneous, and PV2-SiW12/Fe2O3 could be reused at least three times for each oxidation (epoxidation, sulfoxidation, and arene hydroxylation) without appreciable losses of the high catalytic performance.

A basic germanodecatungstate with a - 7 charge: Efficient chemoselective acylation of primary alcohols

The synthesis of highly negatively charged polyoxometalates with electrically and structurally controlled uniform basic sites can lead to the unique base catalysis. In this work, a γ-Keggin germanodecatungstate, [γ-HGeW10O36]7- (A), having a -7 charge was, for the first time, successfully synthesized by the reaction of [γ-H2GeW10O36]6- with one equivalent of [(n-C4H9)4N]OH under non-aqueous conditions. The activities of germanodecatungstates for base-catalyzed reactions dramatically increased with increase in the number negative charges from -6 to -7. In the presence of A, various combinations of acylating agents and primary alcohols including those with acid-sensitive functional groups chemoselectively gave the desired acylated products in high yields even under the stoichiometric conditions.

Oxidative functional group transformations with hydrogen peroxide catalyzed by a divanadium-substituted phosphotungstate

A divanadium-substituted phosphotungstate TBA4[γ-PW 10O38V2(μ-OH)(μ-O)] (I, TBA = tetra-n-butylammonium) reacts with one equivalent H+ to form a bis-μ-hydroxo species [γ-PW10O38V 2(μ-OH)2]3- (I′) in organic media. The strong electrophilic oxidants such as [γ-PW10O 38V2(μ-OH)(μ-OOH)]3- (II) and [γ-PW10O38V2(μ-η2: η2-O2)]3- (III) are formed by the reaction of the bis-μ-hydroxo species with H2O2. In the presence of I and H+, H2O2-based oxidations such as (i) epoxidation of alkenes (17 examples including electron-deficient ones), (ii) hydroxylation of alkanes (11 examples), and (iii) oxidative bromination of alkenes, alkynes, and aromatics with Br- as a bromo source (12 examples including chlorination) chemo-, diastereo-, and regioselectively proceed to give the corresponding oxidized products in moderate to high yields with high efficiencies of H2O2 utilization.

Efficient epoxidation of electron-deficient alkenes with hydrogen peroxide catalyzed by [γ-PW10O38V2(μ-OH) 2]3-

A divanadium-substituted phosphotungstate, [γ-PW10O 38V2(μ-OH)2]3- (I), showed the highest catalytic activity for the H2O2-based epoxidation of allyl acetate among vanadium and tungsten complexes with a turnover number of 210. In the presence of I, various kinds of electron-deficient alkenes with acetate, ether, carbonyl, and chloro groups at the allylic positions could chemoselectively be oxidized to the corresponding epoxides in high yields with only an equimolar amount of H2O2 with respect to the substrates. Even acrylonitrile and methacrylonitrile could be epoxidized without formation of the corresponding amides. In addition, I could rapidly (min) catalyze epoxidation of various kinds of terminal, internal, and cyclic alkenes with H;bsubesubbsubesub& under the stoichiometric conditions. The mechanistic, spectroscopic, and kinetic studies showed that the I-catalyzed epoxidation consists of the following three steps: 1) The reaction of I with H;bsubesubbsubesub& leads to reversible formation of a hydroperoxo species [I;circbsubesubbsubesubbsubesubcirccircbsupesup& (II), 2) the successive dehydration of II forms an active oxygen species with a peroxo group [ 2:2-O2)]3- (III), and 3) III reacts with alkene to form the corresponding epoxide. The kinetic studies showed that the present epoxidation proceeds via III. Catalytic activities of divanadium-substituted polyoxotungstates for epoxidation with H 2O2 were dependent on the different kinds of the heteroatoms (i.e., Si or P) in the catalyst and I was more active than [γ-SiW10O38V2(μ-OH)2] 4-. On the basis of the kinetic, spectroscopic, and computational results, including those of [γ-SiW10O38V 2(μ-OH)2]4-, the acidity of the hydroperoxo species in II would play an important role in the dehydration reactivity (i.e., k3). The largest k3 value of I leads to a significant increase in the catalytic activity of I under the more concentrated conditions. Copyright

MANUFACTURE OF AN EPOXYETHYL CARBOXYLATE OR GLYCIDYL CARBOXYLATE

The invention relates to a process for the manufacture of an epoxyethyl carboxylate or glycidyl carboxylate, including reacting a vinyl carboxylate or an allyl carboxylate using an oxidant and a water-soluble manganese complex in an aqueous reaction medium, and the water-soluble manganese complex comprises an oxidation catalyst, characterized in that the water-soluble manganese complex is a mononuclear species of the general formula (I): [LMnX3]Y, or a binuclear species of the general formula (II): [LMn(μ-X)3MnL]Yn, wherein Mn is a manganese; L is a ligand and each L is independently a polydentate ligand, each X is independently a coordinating species and each μ-X is independently a bridging coordinating species, Y is a non-coordinating counter ion, and wherein the epoxidation is carried out at a pH in the range of from 1.0 to 7.0.