2238-07-5

Usage

Uses

Used in Epoxy Resin Industry:
Diglycidyl ether is used as a reactive diluent for epoxy resins to reduce their viscosity, making them easier to process and apply. This improves the flow and wetting properties of the resin, allowing for better adhesion and coverage.
Used in Chemical Intermediates:
Diglycidyl ether serves as a chemical intermediate in the synthesis of various compounds, including epoxy resins and other polymers. Its reactive nature allows it to be used in the production of a wide range of products.
Used in Stabilization of Chlorinated Organic Compounds:
Diglycidyl ether is used as a stabilizer for chlorinated organic compounds, such as chlorinated solvents and pesticides. It helps to prevent the degradation and decomposition of these compounds, extending their shelf life and performance.
Used in Textile Industry:
Diglycidyl ether is used as a textile-treating agent, where it can improve the properties of fabrics, such as their strength, durability, and resistance to chemicals. It can also be used in the production of specialty fibers and coatings for textiles.

Air & Water Reactions

Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164].

Reactivity Profile

Epoxides, such as DIGLYCIDYL ETHER, are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Health Hazard

DIGLYCIDYL ETHER can cause death or permanent injury via oral and inhalation routes during exposure that comes from normal use. It is incapacitating and poisonous and requires special handling. It can cause considerable discomfort by the dermal route.

Fire Hazard

(Non-Specific -- Poison, Flammable Liquid, n.o.s.) May be ignited by heat, sparks, or flames. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Avoid strong oxidizers.

Safety Profile

Suspected carcinogen with experimental tumorigenic data. Poison by ingestion, inhalation, and intravenous routes. Moderately toxic by skin contact. A severe eye and skin irritant. Mutation data reported. Chronic exposure can cause bone marrow depression. When heated to decomposition it emits acrid smoke and fumes. See also ETHERS.

Carcinogenicity

In mice, diglycidyl ether has been shown to produce epithelioma following repeated skin application. A total dose of 100 mg produced these tumors in 4 of 20 animals; a dose of 33 mg produced only 1/20 .

InChI:InChI=1/C6H10O3/c1(5-3-8-5)7-2-6-4-9-6/h5-6H,1-4H2/t5-,6-/m1/s1

Upstream product

• 2855-13-2 3-aminomethyl-3,5,5-trimethylcyclohexylamine 
• 96-23-1 1,3-Dichloro-2-propanol 
• 67-63-0 isopropyl alcohol 
• 106-89-8 epichlorohydrin 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 56-37-1 N-benzyl-N,N,N-triethylammonium chloride 
• 80-05-7 BPA 
• 67-48-1 choline chloride 
• 3722-51-8 3-hydroxyxanthen-9-one 
• 67843-74-7 (S)-epichlorohydrin 
• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 7646-78-8 tin(IV) chloride 
• 557-40-4 Allyl ether 
• 616-45-5 2-pyrrolidinon 

Downstream Products

• 627-82-7 diglycerol 
• 20600-96-8 diglycerol tetranitrate 
• 338459-04-4 2,6-di-O-benzyl-4-oxaheptane-1,2,6,7-tetraol 
• 338459-03-3 6,10-di-O-benzyl-4,8,12-trioxapentadecane-1,14-diene-6,10-diol 
• 338459-09-9 3,7,11-tri-O-benzyl-1,5,9-trioxacyclododecane-3,7,11-triol 
• 338459-08-8 2,6-di-O-benzyl-1,7-di-O-trifluoromethanesulfonyl-4-oxaheptane-1,2,6,7-tetraol 
• 338459-13-5 3,7,11,15,19-penta-O-benzyl-1,5,9,13,17-pentaoxacycloicosane-3,7,11,15,19-pentaol 
• 106-89-8 epichlorohydrin 
• 931-40-8 4-hydroxymethyl-1,3-dioxolan-2-one 

Relevant academic research and scientific papers

Structure-property relationships in metallosurfactants

The morphology of micelles formed by three sub-classes of metallosurfactants - those with macrocyclic, linear and gemini head groups - has been studied by small-angle neutron scattering (SANS) for a series of metal- and counter-ions. All the data may be described by a model that invokes a globular micelle morphology in which the dimensions of the micelle are consistent with the known chemical structure of the constituent groups within the metallosurfactant. For two macrocyclic head group metallosurfactants, viz. 1-(2-hydroxy-tetradecyl)-1,4,7-triazacyclonane that forms predominantly spherical micelles and 1-(2-hydroxy-tetradecyl)-1,4,7,10-tetraazacyclononane that forms disc-like micelles, the metal ion and its counter-ion have a negligible effect on the morphology of the micelle. Binary mixtures of surfactants with these two macrocyclic head groups (with homo- or hetero-metal ions/counter-ions) form mixed micelles whose morphology is an average of the two single component micelles. Further, as found for the single surfactant solutions, the metal and counter-ion had no effect on the morphology of the mixed surfactant micelle. Lastly, the micelle morphology of two gemini surfactants was also shown to be insensitive to the number and nature of the metal and counter-ions present, but sensitive to the structure of the head group. These observations considerably extend our understanding of the relationship between chemical structure and micelle morphology for these interesting molecules.

Absorbent solution based on beta-hydroxylated tertiary diamines and method of removing acid compounds from a gaseous effluent

An absorbent solution is provided for removing acid compounds contained in a gaseous effluent and a method of removing acid compounds contained in a gaseous effluent contacts the gaseous effluent with the absorbent solution. The absorbent solution includes at least one of the following two nitrogen compounds belonging to the family of tertiary diamines: 1-dimethylamino-3-(2-dimethylaminoethoxy)-2-propanol 1,1′-oxybis[3-(dimethylamino)-2-propanol] and water.

PRODUCTION METHOD OF GLYCIDYL ETHERS

PROBLEM TO BE SOLVED: To provide a method capable of producing simply and efficiently without requiring a special catalyst or a complicated process, glycidyl ethers having a small content of halogen especially chlorine, which is useful in a field avoiding halogen. SOLUTION: There is provided a production method of glycidyl ethers in which alcohols and epihalohydrin are reacted together in the presence of an alkali catalyst. In the production method of glycidyl ethers having a small chlorine content, after charging alcohols and epihalohydrin, the reaction is progressed by adding the alkali catalyst in multistep. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

DIGLYCIDYL ETHERS OF 2-PHENYL-1,3-PROPANEDIOL DERIVATIVES AND OLIGOMERS THEREOF AS CURABLE EPOXY RESINS

Cured epoxy resins are widespread on account of their outstanding mechanical and chemical properties. It is common to use epoxy resins based on bisphenol A diglycidyl ether or bisphenol F diglycidyl ether, but for many sectors these are problematic because of their endocrine effect. The present invention relates to 2-phenyl-1,3-propanediol diglycidyl ether derivates and to curable epoxy resin compositions based thereon, as alternatives to the bisphenol A or bisphenol F diglycidyl ethers and to the epoxy resin compositions based thereon.

Continuous dehydrochlorination of 1,3-dichloropropan-2-ol to epichlorohydrin: Process parameters and by-products formation

The influence of pre-reactor and reactor temperatures on the conversion of 1,3-dichloropropan-2-ol and the selectivity of its transformation to epichlorohydrin in continuous dehydrochlorination for two modes of the reaction product collection was studied. The dehydrochlorination process and mechanism of diglycidyl ether formation are described.

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

Nonamphiphilic assembly in water: Polymorphic nature, thread structure, and thermodynamic incompatibility

Self-assembly of large quantities of entirely water-soluble molecules isentropically challenging. In this work, we describe the design and synt hesis of water-soluble aromatic (dichromonyl) molecules that can form nonamphiphilic assemblies and the so-called chromonic liquid crystal phasein water. We discover a new molecule, 5′DSCG-diviol, that exhibit s a large birefringent phase, and we show that the formation of this unique class of nonamphiphilic lyotropic liquid crystal shares enormous similarity to the polymorphism observed for crystal formation. Small-angle neutron scattering (SANS) revealed a concentration-independent rod-shaped assembly at concentrations below and above the formation of liquid crystal phase. Adding a small percentage of monoanionic aromatic molecules to the liquid crystal resulted in the elimination of the liquid crystal phase, but addition of dianionic aromatic molecules retained the liquid crystal phase. Together, these results suggest a new assembly structure for nonamphiphilic molecules in water, which is comprised of long threads of small molecules connected by salt bridges stacked over aromatic groups, with the molecular threads heavily hydrated with solvent water. Furthermore, mixing molecules with different structures can result in new liquid crystalline materials, or in segregation of the molecules into different solvation volumes, each of which contains only one type of molecule. The unusual thermodynamic incompatibility of entirely water-soluble molecules also supports the model of molecular threads, in which two polymer-like assemblies do not mix.

Methods for Obtaining Optically Active Glycidyl Ethers and Optically Active Vicinal Diols from Racemic Substrates

The invention provides yeast strains, and polypeptides encoded by genes of such yeast strains, that have enantiospecific glycidyl ether hydrolase activity. The invention also features nucleic acid molecules encoding such polypeptides, vectors containing such nucleic acid molecules, and cells containing such vectors. Also embraced by the invention are methods for obtaining optically active glycidyl ethers and associated optically active vicinal diols.

A novel titanosilicate with MWW structure Catalytic properties in selective epoxidation of diallyl ether with hydrogen peroxide

The catalytic activity and selectivity of Ti-MWW in the epoxidation of diallyl ether (DAE) with hydrogen peroxide to allyl glycidyl ether (AGE) and diglycidyl ether (DGE) have been studied by a comparison with those of TS-1, and the issues concerning the consecutive reaction and the selective production of AGE have been considered. Ti-MWW catalyzed the DAE epoxidation in the presence of aprotic solvents such as acetonitrile or acetone, and produced only minor levels of solvolysis products. Ti-MWW proved to be a reusable catalyst standing up to the Ti leaching and maintaining the catalytic activity and the product selectivity in the reaction-regeneration cycles. Studies with different solvents, Ti contents, reaction times, temperature, and catalyst amounts confirmed that the DAE epoxidation was a typical consecutive reaction with AGE as an intermediate product and DGE as a secondary one. The reaction rate for AGE formation was much faster than that for DGE, making the selective production of AGE possible by controlling the reaction up to a DAE conversion level of ca. 30%.