28347-88-8

Usage

Physical state

1,4-dioxane is a clear, colorless, and flammable liquid.

Industrial use

It is primarily used as a solvent in various industrial and commercial applications.

Byproduct

It is often found as a byproduct in the manufacturing of other chemicals, such as certain plastics and detergents.

Additional use

It is also used as a stabilizer in some cosmetic and personal care products.

Health hazard

1,4-dioxane is classified as a likely human carcinogen.

Health effects

Exposure to it has been linked to adverse health effects on the liver, kidneys, and respiratory system.

Environmental impact

It is known to contaminate water sources.

Regulatory scrutiny

It has been the subject of regulatory scrutiny and remediation efforts.

Regulations and monitoring

Its use and presence in consumer products and industrial processes are subject to strict regulations and monitoring.

Upstream product

• 75-21-8 oxirane 
• 368-39-8 triethyloxonium fluoroborate 
• 64-17-5 ethanol 
• 75-04-7 ethylamine 
• 88-73-3 2-Chloronitrobenzene 
• 107-21-1 ethylene glycol 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 106-93-4 ethylene dibromide 
• 628-89-7 2-(2-Chloroethoxy)ethanol 
• 50-00-0 formaldehyd 
• 10160-87-9 Propiolaldehyde diethyl acetal 
• 109-89-7 diethylamine 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 111-46-6 diethylene glycol 

Downstream Products

• 22248-49-3 Erythroaphin-tb 
• 6937-90-2 9-methoxy-2-methyl-benzo[f]chromen-3-one 
• 29959-86-2 1-(phenylsulphenyl)piperidylamide 
• 4610-99-5 tris-methanesulfonyl-methane 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 855180-66-4 N'-(2-hydroxy-phenyl)-N-methyl-N-phenyl-urea 
• 20442-31-3 O,O,S-triisopropyl phosphorodithioate 
• 7336-15-4 hexahydro-1-(2'-cyanoethyl)-2H-azepin-2-one 
• 853920-96-4 cyclohex-2-enyl-[2]thienyl-acetonitrile 
• 94963-68-5 benzoylamino-diphenyl-acetonitrile 
• 1745-77-3 2-benzylquinoline 
• 101722-95-6 2-(phenyl)-β-hydroxyethyl 2-napthyl sulfide 
• 4249-72-3 2-phenoxy-1-phenylethanol 
• 53574-80-4 AB_0000810 

Relevant academic research and scientific papers

Catalysis, kinetic and mechanistical studies for the transformation of ethylene glycol by alumina and silica gel under autogenous pressure and solvent-free conditions

A kinetic and mechanistical studies of the new pathway for competitive transformation of ethylene glycol by alumina and silica gel have been described. Commercial alumina (Al com), synthetic alumina (Al syn), commercial silica gel (Si com) and synthetic silica gel (Si syn) were used for the transformation of ethylene glycol to a mixture of diethylene glycol, 1,4-dioxane and 2-methyl-1,3-dioxolane via acetaldehyde by heating at 150 °C under autogenous pressure without solvent. The results show that the yield of these three products strongly depends on the nature of the used catalyst and the reaction time.

Transition metal triflate catalyzed conversion of alcohols, ethers and esters to olefins

Herein, we report an efficient transition metal triflate catalyzed approach to convert biomass-based compounds, such as monoterpene alcohols, sugar alcohols, octyl acetate and tea tree oil, to their corresponding olefins in high yields. The reaction proceeds through C-O bond cleavage under solvent-free conditions, where the catalytic activity is determined by the oxophilicity and the Lewis acidity of the metal catalyst. In addition, we demonstrate how the oxygen containing functionality affects the formation of the olefins. Furthermore, the robustness of the used metal triflate catalysts, Fe(OTf)3 and Hf(OTf)4, is highlighted by their ability to convert an over 2400-fold excess of 2-octanol to octenes in high isolated yields.

Synthesis of dioxolanes and oxazolidines by silica gel catalysis

Abstract: Ethylene glycol condensed with carbonyl compounds in the presence of silica gel or alumina, without solvent and under pressure, affords 1,3-dioxolanes. 2-Amino-2-methylpropanol also condensed with carbonyl compounds in the presence of silica gel or an acid-activated clay, without solvent and under pressure, produces oxazolidines. To explain these results, we propose that the glycol and the aminopropanol react with Br?nsted (H+) and Lewis acid sites (Si and Al) located on the surface of the catalysts, leading to the products via various ionic intermediates.

Iron-Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers

Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring-closing reactions. Herein, we report an iron-catalyzed ring-closing metathesis of aliphatic ethers for the synthesis of substituted tetrahydropyrans and tetrahydrofurans, as well as morpholines and polycyclic ethers. This transformation is enabled by a simple iron catalyst and likely proceeds via cyclic oxonium intermediates.

Synthesis of cyclic ethers from diols in the presence of copper catalysts

A number of cyclic ethers, namely tetrahydrofuran, 2,5-dimethyltetrahydrofuran, tetrahydropyran, 1,4-dioxane, oxepane, oxocane, and 1,4-oxathiane, have been synthesized in high yields by intramolecular dehydration of diols in the presence of copper-based catalysts.

Thermal and hydrolytic decomposition mechanisms of organosilicon electrolytes with enhanced thermal stability for lithium-ion batteries

The high flammability and thermal instability of conventional carbonate electrolytes limit the safety and performance of lithiumion batteries (LIBs) and other electrochemical energy storage devices. Organosilicon solvents have shown promise due to their reduced flammability and greater chemical stability at high temperatures. A series of organosilicon electrolytes with different functional substituents were studied to understand the structural origins of this enhanced stability. The thermal and hydrolytic stability of organosilicon and carbonate solvents with LiPF6 was probed by storage at high temperatures and with added water. Quantitative monitoring of organosilicon and carbonate electrolyte decomposition products over time using NMR spectroscopy revealed mechanisms of degradation and led to the discovery of a key PF5-complex that forms in organosilicon electrolytes to inhibit further salt breakdown. Increased knowledge of specific structural contributions to electrolyte stability informs the development of future electrolyte solvents to enable the safer operation of high-performing lithium-ion batteries.

METHOD FOR PREPARING DOUBLE-SEALED-END GLYCOL ETHER

Disclosed is a method for preparing a double end capped glycol ether, the method comprising: introducing into a reactor a raw material comprising a glycol monoether and a monohydric alcohol ether, and enabling the raw material to contact and react with an acidic molecular sieve catalyst to generate a double end capped glycol ether, a reaction temperature being 50-300° C., a reaction pressure being 0.1-15 MPa, a WHSV of the glycol monoether in the raw material being 0.01-15.0 h?1, and a mole ratio of the monohydric alcohol ether to the glycol monoether in the raw material being 1-100:1. The method of the present invention enables a long single-pass lifespan of the catalyst and repeated regeneration, has a high yield and selectivity of a target product, low energy consumption during separation of the product, a high economic value of a by-product, and is flexible in production scale and application.

Selective synthesis of dimethoxyethane via directly catalytic etherification of crude ethylene glycol

Etherification of ethylene glycol with methanol provides a sustainable route for the production of widely used dimethoxyethane; dimethoxyethane is a green solvent and reagent that is applied in batteries and used as a potential diesel fuel additive. SAPO-34 zeolite was found to be an efficient and highly selective catalyst for this etherification via a continuous flow experiment. It achieved up to 79.4% selectivity for dimethoxyethane with around 96.7% of conversion. The relationship of the catalyst's structure and the dimethoxyethane selectivity was established via control experiments. The results indicated that the pore structure of SAPO-34 effectively limited the formation of 1,4-dioxane from activated ethylene glycol, enhanced the reaction of the activated methanol with ethylene glycol in priority, and thus resulted in high selectivity for the desired products. The continuous flow technology used in the study could efficiently promote the complete etherification of EG with methanol to maintain high selectivity for dimethoxyethane.

Manufacturing method and composition of alkylene ether of bisphenol compd. dioxyethylene

PROBLEM TO BE SOLVED: To provide a method for efficiently producing a dioxyalkylene ether of a bisphenol compound containing little amount of by-products and having high purity in industrialization in the method for producing a dioxyalkylene ether of a bisphenol compound from a bisphenol compound.SOLUTION: The method for producing a dioxyalkylene ether (B) of a bisphenol compound (A) by adding a 2-4C alkylene oxide to a bisphenol compound includes a step (I) of carrying out the reaction in the presence of a catalyst (C) in a mixed solvent (S) of water and the following solvent (S1) at a reaction temperature of 30-80°C. The solvent (S1): a solvent capable of dissolving ≥1 g of the dioxyalkylene ether (B) of the bisphenol compound in 100 g of the solvent.

Production of aldehydes from 1,2-alkanediols over silica-supported WO3 catalyst

Vapor-phase dehydration of several 1,2-alkanediols, such as 1,2-ethanediol, 1,2-propanediol, 1,2-butanediol and 1,2-pentanediol, to produce corresponding aldehydes was investigated over silica-supported WO3 catalyst, which was prepared by impregnation method and then calcined at 320?°C. Higher than 90% yield of aldehydes could be achieved over WO3/SiO2 catalyst at 250?°C with a feed of 20% aqueous 1,2-alkanediol solution. Both Br?nsted and Lewis acid sites exist on WO3/SiO2 catalyst, while Br?nsted acid sites are proposed to be the active species for the formation of aldehyde. High concentrations of H2O were effective for inhibiting the intermolecular reaction and improving the selectivity to aldehydes. The dehydration of different 1,2-alkanediols was compared under different reaction conditions. The reactivity of 1,2-ethanediol was low and the product distribution was several comparing with those of the other 1,2-alkanediols. Cyclic acetal, which was generated by the cyclodehydration of the produced aldehyde with another 1,2-alkanediol, was a main by-product, and the formation of acetal was affected by both the temperature and the carbon-chain length of the 1,2-alkanediols.