1,4-DIOXANE
1,4-dioxane is primarily used as a solvent in the chemical industry, particularly for dissolving resins, plastics, and oils, as well as for extracting essential oils and other organic substances.
Despite its utility, 1,4-dioxane is considered a hazardous substance and is classified as a potential human carcinogen by multiple health and safety organizations.
The global market for 1,4-dioxane is characterized by its diverse applications across several industries, including pharmaceuticals, chemicals, cosmetics, and manufacturing.
CAS Number: 123-91-1
EC Number: 204-661-8
Chemical Formula: C4H8O2
Molecular Weight: 88.11 g/mol
Synonyms: Diethylene oxide, Dioxane, Dioxane , p-Dioxane , Glycolethylether, 1,4-Diethylene dioxide , 1,4-Dioxacyclohexane, 1,4-DIOXANE, Dioxane, 123-91-1, p-Dioxane, 1,4-Diethylene dioxide, Dioxan, Diethylene ether, 1,4-Dioxacyclohexane, Tetrahydro-p-dioxin, Di(ethylene oxide), Tetrahydro-1,4-dioxin, Dioxane-1,4, Dioxanne, Diethylene dioxide, Glycol ethylene ether, 1,4-Dioxan, Dioxan-1,4, Dioksan, p-Dioxan, Tetrahydro-para-dioxin, Dioxyethylene ether, Diokan, para-Dioxane, Diossano-1,4, Dioxaan-1,4, p-Dioxin, tetrahydro-, RCRA waste number U108, 1,4-Dioxanne, NCI-C03689, 1, 4-dioxane, NSC 8728, UNII-J8A3S10O7S, NE 220, 1.4-dioxane, 1-4 Dioxane, MFCD00006571, 1,4-Dioxin, tetrahydro-, UN 1165, J8A3S10O7S, CHEBI:47032, 1, 4-Diethylene dioxide, Glycolethylenether, Dioksan, Dioxane anhydrous, HPLC Grade, Dioxanne, p-Dioxan , 1,4-Diethyleneoxide, [1,4]dioxane, Dioxane, technical grade, Dioxaan-1,4 , Dioxan-1,4, 1,4-Dioxanne, Diossano-1,4, HSDB 81, CCRIS 269, Dioxane anhydrous, ACS reagent, >=99.0%, 1,4-Diethylenedioxide, EINECS 204-661-8, UN1165, RCRA waste no. U108, BRN 0102551, paradioxane, AI3-01055, P-Doxane, 1,4dioxane, Dioxane anhydrous solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), NMR tube size 5 mm x 8 in., 1,4dioxan, 1,4 dioxane, 1-4-dioxane, 1,4 dioxan, Dioxane 1.4, 1 ,4-dioxane, 1, 4 dioxane, 1,-4-dioxane, 1,4 -dioxane, 1,4,-dioxane, 1,4- dioxane, 1,4-di-oxane, 1 ,4-dioxan, 1,4 -dioxan, [1,4]-dioxane, Glycol ethylene ether 8, Dioxane anhydrous, anhydrous, DSSTox_CID_533, WLN: T6O DOTJ, Dioxane anhydrous, homopolymer, EC 204-661-8, Dioxane anhydrous, for HPLC, Dioxane anhydrous, ACS Grade, DSSTox_RID_75644, DSSTox_GSID_20533, 5-19-01-00016, BIDD:ER0341, CHEMBL453716, Dioxane anhydrous, SAJ first grade, DTXSID4020533, 9042Af, NSC8728, Dioxane anhydrous, analytical standard, Dioxane anhydrous, p.a., 99, Dioxane anhydrous, LR, >=99%, AMY33329, BCP16201, NSC-8728, ZINC1648204, Dioxane anhydrous, anhydrous, 99.8%, Tox21_200971, STL264191, AKOS000120203, Dioxane anhydrous, AR, >=99.5%, Dioxane anhydrous, HPLC grade, 99.9%, DB03316, MCULE-5088019198, Dioxane, NCGC00248888-01, NCGC00258524-01, Dioxane anhydrous, for HPLC, >=99.5%, Dioxane anhydrous, for HPLC, >=99.7%, Dioxane anhydrous, ReagentPlus(R), >=99%, CAS-123-91-1, Dioxane anhydrous 1000 microg/mL in Methanol, Dioxane anhydrous, AldraSORB(TM), 99.8%, Dioxane anhydrous, histological grade, >=99%, DB-025338, D0860, FT-0606896, FT-0606897, Dioxane anhydrous 1000 microg/mL in Acetonitrile, Dioxane anhydrous, JIS special grade, >=99.0%, Dioxane anhydrous, spectrophotometric grade, >=99%, Dioxane anhydrous, UV HPLC spectroscopic, 99.9%, Dioxane anhydrous, anhydrous, ZerO2(TM), 99.8%, Q161532, J-004995, J-523874, BRD-K42978307-001-01-0, Dioxane anhydrous, >=99.5%, for titration in non-aqueous medium, Dioxane anhydrous, puriss. p.a., dried, >=99.5% (GC), <=0.005% water, Dioxane anhydrous, Pharmaceutical Secondary Standard; Certified Reference Material, Dioxane anhydrous, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., >=99.5% (GC), Dioxane anhydrous, puriss., absolute, over molecular sieve (H2O <=0.01%), >=99.5% (GC), Dioxane anhydrous solution, certified reference material, 2000 mug/mL in methanol, ampule of 1 mL, Dioxane anhydrous solution, NMR reference standard, 0.1 mM in D2O ("100%", 99.96 atom % D), NMR tube size 5 mm x 7 in., Dioxane anhydrous solution, NMR reference standard, 1 mM in D2O ("100", 99.96 atom % D), NMR tube size 5 mm x 7 in., Dioxane anhydrous solution, NMR reference standard, 10 mM in chloroform-d (99.8 atom % D), NMR tube size 5 mm x 8 in., Dioxane anhydrous solution, NMR reference standard, 10 mM in D2O ("100%", 99.96 atom % D), NMR tube size 5 mm x 7 in., Dioxane anhydrous solution, NMR reference standard, 10 mM in methanol-d4 (99.8 atom % D), NMR tube size 5 mm x 8 in., Dioxane anhydrous solution, NMR reference standard, 10% in benzene-d6 (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 5 mm x 8 in., Dioxane anhydrous solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 3 mm x 8 in., Dioxane anhydrous solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 5 mm x 8 in., Dioxane anhydrous solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 6.5 mm x 8 in., Dioxane anhydrous solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), NMR tube size 10 mm x 8 in., Dioxane anhydrous solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), NMR tube size 3 mm x 8 in., Dioxane anhydrous solution, NMR reference standard, 5 mM in benzene-d6 (99.6 atom % D), NMR tube size 3 mm x 8 in., Dioxane anhydrous solution, NMR reference standard, 5 mM in chloroform-d (99.8 atom % D), NMR tube size 3 mm x 8 in., 28552-22-9, 39449-24-6, 54841-74-6, Dioxane anhydrous, 1,4-Dioxan, Dioxane anhydrous ZerO2(R), 1,4-Dioxanne, 102551 , 123-91-1 , 212-378-6, 212-742-4, 232-148-9 , 241-628-7 , Degassed and low oxygen 1,4-dioxane, diethylene oxide, Diossano-1,4, Dioxan-1,4, dioxane , Dioxane, 1,4-, MFCD00006571, p-Dioxan, p-dioxane, Residual Solvent Class 2 - Dioxane anhydrous, 1,4 Dioxane, 1,4-DIETHYLENE DIOXIDE, 1,4-Diethylenedioxide, 1,4-Diethyleneoxide, 1,4-dioxacyclohexane, 1,4-Dioxan, GlenDry, anhydrous, Dioxane anhydrous, 1, Dioxane anhydrous, anhydrous, 1,4-DIOXANE-D8, Dioxane anhydrousmissing, 1,4-Dioxin, tetrahydro-, 1.4-Dioxane, 2-(2-Methoxyethoxy)ethanol , 205391-01-1, 4-[(3-nitrophenyl)methyl]morpholine, 4598-47-4, 5-19-01-00016, 5-19-01-00016, 927819-64-5, Di (ethylene oxide), di(ethylene oxide), Diethylene dioxide, diethylene ether, diokan, Dioksan, Diossano-1,4, Dioxaan-1,4, DIOXAN, Dioxan-1,4, DIOXANE 1,4, dioxane-1,4, Dioxanne, Dioxyethylene ether, dry, ethylene glycol ethylene ether, glycol ethylene ether, Glycol ethylene ether 8, Glycolethylenether, Glycolethylether, 1,4-Diethylene dioxide, 1,4-Dioxacyclohexane, para-Dioxane, p-Dioxin, tetrahydro-, PG0, T6O DOTJ, TETRAHYDRO-1,4-DIOXIN, tetrahydro-para-dioxin, tetrahydro-p-dioxin, WLN: T6O DOTJ
1,4-dioxane is an organic compound with the chemical formula C4H8O2.
1,4-dioxane is a colorless, flammable liquid with a slightly sweet odor and is commonly used as a solvent in a variety of industrial and chemical applications.
1,4-dioxane is primarily used as a solvent in the chemical industry, particularly for dissolving resins, plastics, and oils, as well as for extracting essential oils and other organic substances.
1,4-dioxane also finds use as a stabilizer in certain chemical reactions, including the stabilization of hydrogen peroxide solutions.
1,4-dioxane is highly miscible with water and many organic solvents, making it a versatile solvent for a wide range of reactions and formulations.
In addition to its solvent properties, 1,4-dioxane plays a role in the synthesis of various chemical compounds.
1,4-dioxane is used in the preparation of polymerization reactions, particularly in the production of synthetic fibers, resins, and coatings.
1,4-dioxane is also utilized in the manufacture of pharmaceuticals, where it is used as a medium for dissolving active ingredients during drug formulation processes.
Due to its chemical stability and ability to dissolve a broad range of substances, 1,4-dioxane has been widely adopted in laboratories for research and testing purposes.
Despite its utility, 1,4-dioxane is considered a hazardous substance.
1,4-dioxane is classified as a potential human carcinogen by multiple health and safety organizations, including the U.S. Environmental Protection Agency (EPA), due to its ability to cause cancer in laboratory animals and its potential to cause liver and kidney damage.
As such, 1,4-dioxane must be handled with care in controlled environments, and protective measures should be taken to limit exposure to vapors and skin contact.
Furthermore, due to its environmental impact, 1,4-dioxane has been a subject of concern in wastewater and groundwater contamination.
Regulations have been implemented in several countries to minimize its release into the environment, and industries using 1,4-dioxane are required to adhere to specific safety protocols to ensure proper disposal and containment.
Overall, 1,4-dioxane is a valuable industrial solvent with diverse applications in chemical synthesis, manufacturing, and research.
However, 1,4-dioxane's toxicological profile underscores the importance of careful handling, proper storage, and adherence to environmental and safety regulations to mitigate potential risks.
1,4-dioxane, is used as a solvent as well as a stabilizer for the solvent trichloroethane.
Anhydrous, dry, without water, is used when performing certain reactions where the presence of water can prevent a chemical reaction from happening, or form undesirable products.
1,4-dioxane is used as a solvent for a variety of practical applications as well as in the laboratory, and also as a stabilizer for the transport of chlorinated hydrocarbons in aluminum containers.
1,4-dioxane is a hexahydroxy heterocyclic compound containing two oxygen heteroatoms.
1,4-dioxane Vapor can easily form explosive peroxides by absorbing oxygen in the air.
1,4-dioxane can form azeotrope with water (water content 18.6%) and the boiling point is 87.8 ℃.
1,4-dioxane turns bright yellow when reacting with tetranitromethane.
As a good organic solvent, 1,4-dioxane has a wide application such as the solvent for cellulose acetate and lots of resins.
1,4-dioxane is mainly used in the pharmaceutical industry as extraction agent, as a stabilizer in the production of 1,1,1 – trichloroethane as a volatile solvent in the production of polyurethane in place of dimethylformamide and tetrahydrofuran, as stripping agent in the crafts of coating and painting, as a solvent and dispersant in the dye industry, as a stabilizer in printing ink, and also as treatment agent for metal surface.
In addition, 1,4-dioxane can also be used in cosmetics, spices manufacture, electroplating, etc.
1,4-dioxane is a highly versatile and widely used solvent in industrial, laboratory, and pharmaceutical applications.
With a molecular structure composed of two oxygen atoms and four carbon atoms in a cyclic ether configuration, 1,4-dioxane serves as an effective solvent for polar and nonpolar substances alike, making it invaluable in many chemical processes.
1,4-dioxane's unique solvency power enables it to dissolve a wide variety of compounds, including resins, oils, fats, and waxes, as well as organic compounds like aromatic hydrocarbons and esters.
The ability of 1,4-dioxane to dissolve such a broad spectrum of chemicals makes it indispensable in industries like coatings, adhesives, and plastics manufacturing, where specific solvent properties are crucial.
1,4-dioxane is particularly favored in laboratory settings as a solvent for chemical reactions due to its stability and ability to dissolve a broad range of substances without reacting with them.
1,4-dioxane is frequently used in synthetic organic chemistry, including reactions such as nucleophilic substitutions, Grignard reactions, and in the synthesis of various organic compounds such as heterocycles and pharmaceuticals.
In particular, 1,4-dioxane is involved in the production of drugs, agrochemicals, and dyes, often aiding in the dissolution of active ingredients or in the preparation of reaction mixtures.
One of the notable uses of 1,4-dioxane is in the polymerization industry.
As a co-solvent or stabilizer, 1,4-dioxane aids in the production of polymers like polyethylene and polystyrene, and is used in the manufacture of synthetic fibers such as acrylic and nylon.
In these applications, 1,4-dioxane helps ensure smooth polymerization reactions by maintaining a stable environment and preventing unwanted side reactions.
1,4-dioxane also serves as an extraction solvent, especially in the food, fragrance, and essential oil industries, where its solvent properties make it useful for extracting flavor and fragrance compounds from plant material.
Additionally, in the formulation of certain consumer products, 1,4-dioxane is employed in the creation of emulsions and mixtures that require stable and consistent homogeneity, such as in cosmetics and personal care products.
Beyond its beneficial industrial and chemical uses, 1,4-dioxane has raised health and environmental concerns due to its toxicity.
Prolonged exposure to 1,4-dioxane can lead to health issues, such as liver and kidney damage, central nervous system depression, and skin irritation.
1,4-dioxane is easily absorbed through the skin and can accumulate in tissues, which increases the potential for harmful long-term effects.
As a suspected carcinogen, there have been numerous studies investigating 1,4-dioxane's potential effects on human health, particularly with respect to its role in causing cancer.
In animals, 1,4-dioxane has been shown to induce tumors in organs such as the liver and kidneys, prompting significant regulatory action regarding its use in consumer products and manufacturing processes.
In terms of environmental impact, 1,4-dioxane is considered a pollutant of concern due to its solubility in water and persistence in the environment.
1,4-dioxane is not easily biodegradable, and its presence in wastewater or groundwater can lead to long-term contamination.
1,4-dioxane contamination is a known issue in areas where industrial facilities use or dispose of dioxane-containing products.
As a result, water treatment plants often struggle to remove 1,4-dioxane from contaminated water sources, making it a persistent environmental contaminant.
Various regulatory bodies, including the U.S. Environmental Protection Agency (EPA) and the European Union, have set stringent limits on 1,4-dioxane concentrations in drinking water and wastewater discharges to minimize its environmental footprint.
To mitigate the risks associated with 1,4-dioxane exposure and environmental contamination, industries are required to implement rigorous safety protocols, including proper storage, handling, and disposal procedures.
Advances in technology have also led to the development of more effective methods for removing 1,4-dioxane from contaminated sites and wastewater.
These technologies include advanced oxidation processes and bioremediation techniques, which offer potential for breaking down 1,4-dioxane in polluted environments.
In summary, while 1,4-dioxane remains an essential tool in many industrial, pharmaceutical, and research applications due to its excellent solvency properties and chemical stability, its toxicity and environmental persistence pose significant risks that require careful management and regulation.
As industries continue to rely on 1,4-dioxane for a variety of chemical processes, ongoing research into safer alternatives and methods for minimizing its impact on human health and the environment is crucial.
Market Overview of 1,4-dioxane:
The global market for 1,4-dioxane is characterized by its diverse applications across several industries, including pharmaceuticals, chemicals, cosmetics, and manufacturing.
As a versatile solvent and intermediate, 1,4-dioxane plays a critical role in organic synthesis, polymer production, and as a co-solvent in various chemical reactions.
The demand for 1,4-dioxane is primarily driven by its use in the production of pharmaceuticals, where it aids in drug formulation and synthesis, as well as in the extraction of essential oils and fragrances for the cosmetic and fragrance industries.
The increasing need for high-quality solvents in research and development, particularly in the pharmaceutical sector, is boosting market growth.
Additionally, the growth of industries such as personal care, plastics, and chemicals continues to fuel the demand for 1,4-dioxane.
1,4-dioxane's use in the extraction of plant-based compounds, including essential oils and bioactive ingredients, has also contributed to its importance in the natural products market.
However, the market is facing challenges related to the toxicity and environmental concerns associated with 1,4-dioxane.
Stricter environmental regulations and the growing emphasis on sustainability have led to an increased interest in safer alternatives to 1,4-dioxane.
This has prompted ongoing research into green solvents and innovations aimed at minimizing 1,4-dioxane’s environmental footprint.
Geographically, North America and Europe dominate the market due to the high concentration of chemical and pharmaceutical industries in these regions.
However, with the expansion of industrialization in emerging economies such as China and India, the demand for 1,4-dioxane is expected to rise in the Asia Pacific region as well.
Overall, while 1,4-dioxane remains a key compound in various industrial processes, its future market growth will be influenced by regulatory pressures, technological advancements, and the shift toward more sustainable and eco-friendly alternatives.
Uses of 1,4-dioxane:
1,4-dioxane is a versatile solvent widely utilized in various industrial and commercial applications due to its ability to dissolve a broad range of substances.
In organic chemistry, 1,4-dioxane serves as a solvent for reactions such as nucleophilic substitutions and Grignard reactions, aiding in the synthesis of complex compounds.
1,4-dioxane is also integral to the polymerization processes in the plastics industry, where it acts as a co-solvent or stabilizer for the production of materials like polyethylene and polystyrene.
In the pharmaceutical sector, 1,4-dioxane is used to dissolve active ingredients, facilitating the synthesis of various drugs.
Additionally, 1,4-dioxane finds application in the extraction of essential oils and fragrances, where its solvent properties help in isolating aromatic compounds from plant materials.
In the cosmetics industry, 1,4-dioxane is used to create stable formulations in products like shampoos, lotions, and creams by aiding in ingredient dissolution and emulsification.
1,4-dioxane also plays a role in the manufacture of lubricants, greases, dyes, and pigments, ensuring smooth production processes.
Despite its widespread use, the toxicity of 1,4-dioxane has led to stricter regulations and research into safer alternatives, particularly in applications involving human exposure or environmental impact.
1,4-dioxane is used as a solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, some dyes, and other organic and inorganic compounds.
1,4-dioxane is used as a solvent for cellulose esters, ethers, and other organic chemicals.
1,4-dioxane is used as a solvent in resins, polymers, oils, waxes, dyes, wood pulping, adhesives, varnishes lacquers, paints, and cosmetics.
The largest single use of 1,4-dioxane is the stabilization of 1,1,1-trichloroethane against chemical attack by aluminum.
Historically, 1,4-dioxane has been used as a stabilizer for the solvent 1,1,1-trichloroethane.
1,4-dioxane is used as a solvent in the formulation of inks, coatings, and adhesives, and as solvent for extracting animal and vegetable oils.
As a chemical intermediate, 1,4-dioxane reaction products are useful as insecticides, herbicides, plasticizers, and monomers.
The oxonium complexes of 1,4-dioxane with salts, mineral acids, halogens, and sulfur trioxide are used as catalysts and as reagents for anhydrous acid reactions, brominations, and sulfonations.
In the laboratory, 1,4-dioxane is useful as a cryoscopic solvent for molecular mass determinations and as a stable reaction medium for diverse reactions.
1,4-dioxane has a wide range of uses in various industrial, laboratory, and commercial applications.
Some of the key uses include:
Solvent in Chemical Synthesis:
1,4-dioxane is commonly used as a solvent in organic chemistry, particularly in reactions involving polar and nonpolar compounds.
1,4-dioxane is employed in synthetic organic chemistry for reactions such as nucleophilic substitutions, Grignard reactions, and polymerizations.
1,4-dioxane dissolves a broad range of chemicals, making it an essential solvent in chemical labs.
Polymerization and Plastics Industry:
1,4-dioxane serves as a co-solvent or stabilizer in the polymerization of various plastics, including polyethylene, polystyrene, acrylics, and nylon.
1,4-dioxane helps maintain stability during the polymerization process, ensuring smooth and controlled reactions.
Pharmaceutical Manufacturing:
1,4-dioxane is used in the pharmaceutical industry to dissolve active ingredients and facilitate the synthesis of various drugs, including pharmaceutical compounds and agrochemicals.
1,4-dioxane aids in the formulation of drugs by dissolving and homogenizing complex ingredients.
Extraction Solvent:
1,4-dioxane is used as an extraction solvent in the food and fragrance industries to extract essential oils, flavors, and fragrances from plant material.
1,4-dioxane's ability to dissolve both polar and nonpolar compounds makes it ideal for extracting a wide range of natural products.
Cosmetics and Personal Care Products:
1,4-dioxane is employed in the formulation of cosmetics, shampoos, lotions, creams, and other personal care products.
1,4-dioxane is used to dissolve and mix ingredients, ensuring smooth and stable formulations.
1,4-dioxane's ability to act as an emulsifier also helps in creating stable oil-water mixtures in cosmetic products.
Lubricants and Greases:
1,4-dioxane is used as a component in lubricants and greases, where its solvent properties aid in maintaining the consistency and performance of these products.
1,4-dioxane helps in the formulation of high-performance lubricants used in various industrial and automotive applications.
Manufacturing of Dyes and Pigments:
1,4-dioxane is used as a solvent in the manufacturing of dyes and pigments.
1,4-dioxane helps dissolve and mix the components of dyes, ensuring even distribution and uniformity in the final products.
Cleaning and Degreasing:
1,4-dioxane is used as a cleaning solvent for degreasing metal parts, electronic components, and machinery in various industrial processes.
1,4-dioxane effectively removes oils, fats, and grease from surfaces.
Water Treatment and Environmental Applications:
While 1,4-dioxane itself is a contaminant in water, it has been used in environmental applications to help break down or remove other contaminants.
In some cases, advanced oxidation processes (AOPs) that involve 1,4-dioxane may be used for treating contaminated water.
Due to its widespread use, 1,4-dioxane has many commercial and industrial applications, but the toxicity and environmental impact of 1,4-dioxane have led to increased regulation and a focus on finding safer alternatives in some sectors.
Trichloroethane transport:
In the 1980s, most of the 1,4-dioxane produced was used as a stabilizer for 1,1,1-trichloroethane for storage and transport in aluminium containers.
Normally aluminium is protected by a passivating oxide layer, but when these layers are disturbed, the metallic aluminium reacts with trichloroethane to give aluminium trichloride, which in turn catalyses the dehydrohalogenation of the remaining trichloroethane to vinylidene chloride and hydrogen chloride.
1,4-dioxane "poisons" this catalysis reaction by forming an adduct with aluminum trichloride.
As a solvent:
1,4-dioxane is used in a variety of applications as a versatile aprotic solvent, e. g. for inks, adhesives, and cellulose esters.
1,4-dioxane is substituted for tetrahydrofuran (THF) in some processes, because of its lower toxicity and higher boiling point (101 °C, versus 66 °C for THF).
While diethyl ether is rather insoluble in water, 1,4-dioxane is miscible and in fact is hygroscopic.
At standard pressure, the mixture of water and 1,4-dioxane in the ratio 17.9:82.1 by mass is a positive azeotrope that boils at 87.6 C.
The oxygen atoms are Lewis-basic, and so 1,4-dioxane is able to solvate many inorganic compounds and serves as a chelating diether ligand.
1,4-dioxane forms 1:1 adducts with a variety of Lewis acids such as I2, phenols, alcohols, and bis(hexafloroacetylacetonato)copper(II).
1,4-dioxane is classified as a hard base and its base parameters in the ECW model are EB =1.86 and CB = 1.29.
1,4-dioxane reacts with Grignard reagents to precipitate the magnesium dihalide.
In this way, 1,4-dioxane is used to drive the Schlenk equilibrium.
Dimethylmagnesium is prepared in this manner:
2 CH3MgBr + (C2H4O)2 → MgBr2(C2H4O)2 + (CH3)2Mg
Spectroscopy:
1,4-dioxane is used as an internal standard for nuclear magnetic resonance spectroscopy in deuterium oxide.
Industry Uses:
Functional fluids (closed systems)
Laboratory chemicals
Processing aids, not otherwise listed
Consumer Uses:
Golf and Sports Turf
Production of 1,4-dioxane:
The production of 1,4-dioxane typically involves the dehydration of its (a cyclic ether) or the reaction of ethylene glycol with formaldehyde in the presence of a catalyst.
The primary methods of manufacturing 1,4-dioxane include chemical synthesis and distillation processes.
Synthesis from Ethylene Glycol and Formaldehyde: One common method for the production of 1,4-dioxane involves the reaction of ethylene glycol (a simple diol) with formaldehyde (a widely used carbonyl compound) under controlled conditions.
This reaction forms 1,4-dioxane, which is then dehydrated to remove any residual water and obtain 1,4-dioxane.
Cyclization of Diethylene Glycol:
Another method involves the cyclization of diethylene glycol, a compound that contains two ethoxy groups.
This cyclization reaction forms 1,4-dioxane, which can be purified through distillation and other processes to remove moisture and yield 1,4-dioxane.
Separation and Purification:
Once 1,4-dioxane is synthesized, it often contains trace amounts of water.
To obtain 1,4-dioxane, this water must be removed through various drying techniques, such as the use of molecular sieves or anhydrous drying agents.
The drying process helps in ensuring that the final product is water-free, making it suitable for industrial applications that require anhydrous conditions.
Fractional Distillation:
The production of high-purity 1,4-dioxane can also be achieved through fractional distillation.
In this process, 1,4-dioxane is separated from other volatile components by selectively heating the mixture, exploiting differences in boiling points.
This process helps to remove any residual water or byproducts, leading to 1,4-dioxane.
The production of 1,4-dioxane is generally carried out in large-scale chemical manufacturing facilities that are equipped to handle the synthesis, purification, and packaging of this highly versatile solvent.
With the increasing demand for 1,4-dioxane in various industries, manufacturers focus on optimizing production processes to increase efficiency while adhering to safety and environmental regulations.
Given the concerns related to the environmental impact and health risks of 1,4-dioxane, some manufacturers are exploring green chemistry alternatives to reduce its production and use in certain applications, which has also driven research into more sustainable production methods.
Synthesis of 1,4-dioxane:
1,4-dioxane is produced by the acid-catalysed dehydration of diethylene glycol, which in turn is obtained from the hydrolysis of ethylene oxide.
In 1985, the global production capacity for 1,4-dioxane was between 11,000 and 14,000 tons.
In 1990, the total U.S. production volume of 1,4-dioxane was between 5,250 and 9,150 tons.
Structure of 1,4-dioxane:
The 1,4-dioxane molecule is centrosymmetric, meaning that 1,4-dioxane adopts a chair conformation, typical of relatives of cyclohexane.
However, the molecule is conformationally flexible, and the boat conformation is easily adopted, e.g. in the chelation of metal cations.
1,4-dioxane resembles a smaller crown ether with only two ethyleneoxyl units.
History of 1,4-dioxane:
The history of 1,4-dioxane dates back to the early 20th century, when its chemical structure and properties were first explored.
Here is an overview of the significant milestones in 1,4-dioxane's development:
Discovery and Early Research (1920s-1930s):
1,4-dioxane was first synthesized in the early 1920s.
1,4-dioxane was discovered by the German chemist Max J. J. Knop in 1927.
He achieved this by cyclizing diethylene glycol under acidic conditions, leading to the formation of the 1,4-dioxane ring structure.
Early research into 1,4-dioxane focused primarily on understanding its molecular structure and chemical properties, including its high solubility in water and its behavior as a solvent.
Industrial Use and Growth (1940s-1960s):
As the chemical and manufacturing industries grew in the mid-20th century, 1,4-dioxane began to be used more widely, primarily as a solvent for industrial applications.
During this period, 1,4-dioxane gained attention for its ability to dissolve various organic compounds, including oils, resins, and polymers.
In addition to its use in solvent applications, 1,4-dioxane was also explored as a stabilizer for some chlorinated compounds, including trichloroethylene, which further increased its demand in industrial settings.
Expansion in Chemical Industries (1970s-1980s):
In the 1970s and 1980s, the demand for 1,4-dioxane continued to grow, particularly as a solvent in the formulation of chemical products such as paints, varnishes, adhesives, and coatings.
1,4-dioxane also became more widely used in the pharmaceutical and cosmetic industries, where it was included in formulations due to its ability to dissolve a variety of compounds.
Additionally, research continued into 1,4-dioxane's use in the synthesis of other chemicals, further expanding its commercial applications.
Environmental and Health Concerns (1980s-Present):
By the 1980s, concerns about the environmental and health impacts of 1,4-dioxane began to emerge.
As a persistent environmental contaminant, 1,4-dioxane was found to be a potential carcinogen and a significant contaminant in water sources.
Regulatory agencies, including the Environmental Protection Agency (EPA) in the United States, began to investigate and monitor 1,4-dioxane's presence in water and industrial effluents.
Studies linked exposure to 1,4-dioxane with risks of cancer and organ toxicity, which led to restrictions on its use in consumer products and the implementation of safety guidelines in industrial settings.
Regulatory Measures and Research into Alternatives (2000s-Present):
In recent years, increasing awareness about the environmental impact of 1,4-dioxane, especially in wastewater and groundwater, has led to heightened regulation.
Efforts have been made to reduce 1,4-dioxane's use in various consumer products, including cosmetics and pharmaceuticals.
Additionally, research has focused on finding safer alternatives to 1,4-dioxane, such as greener solvents, to reduce its harmful effects on human health and the environment.
1,4-dioxane is now often considered a byproduct or contaminant in industrial processes, and efforts are being made to reduce its concentration in manufacturing processes and to develop more sustainable production methods.
Overall, while 1,4-dioxane has a long history of use in various industries, its potential health risks and environmental concerns have driven significant changes in its regulation and production methods.
As a result, 1,4-dioxane's use has been re-evaluated, with growing emphasis on developing safer and more eco-friendly alternatives in the industries that once relied heavily on this solvent.
Handling and Storage of 1,4-dioxane:
Handling:
Always handle 1,4-dioxane in well-ventilated areas to minimize inhalation exposure.
Avoid contact with skin and eyes.
Use appropriate gloves and protective clothing.
Ensure proper storage to prevent leaks and spills, as dioxane can be harmful if 1,4-dioxane comes into contact with water sources.
Avoid generating vapors or mist, as inhalation can be harmful.
Use appropriate containment to avoid contact with incompatible materials.
Storage:
Store in tightly closed containers in a cool, dry, and well-ventilated area.
Keep away from heat, sparks, open flames, and sources of ignition.
Store away from reactive chemicals such as strong acids, strong bases, and strong oxidizing agents.
Ensure containers are clearly labeled and free from damage to avoid leaks.
Containers should be equipped with secondary containment measures to prevent spills in case of breakage.
Stability and Reactivity of 1,4-dioxane:
Stability:
1,4-dioxane is relatively stable under normal conditions of use and storage, but it should be protected from light and sources of heat.
Conditions to Avoid:
Avoid exposure to excessive heat, open flames, or sparks, which could cause decomposition.
Prolonged exposure to air or sunlight may lead to degradation.
Incompatible Materials:
Strong oxidizing agents such as peroxides, hydrogen peroxide, potassium permanganate, and chlorine.
Strong acids and bases may cause harmful reactions.
Hazardous Decomposition Products:
In the event of a fire or thermal decomposition, 1,4-dioxane may produce harmful gases such as carbon monoxide, carbon dioxide, and smoke.
First Aid Measures of 1,4-dioxane:
Inhalation:
Move the affected person to fresh air immediately.
If breathing is difficult, administer oxygen.
Seek medical attention if symptoms persist.
Skin Contact:
Immediately wash affected skin with soap and water for at least 15 minutes.
Remove contaminated clothing and footwear.
Seek medical attention if irritation persists or if there is significant exposure.
Eye Contact:
Rinse eyes with water or saline solution for at least 15 minutes while holding the eyelids open.
Seek medical attention immediately if irritation or injury occurs.
Ingestion:
Do not induce vomiting unless directed by medical personnel.
If the person is conscious, have them drink water or milk to dilute the substance.
Seek medical attention immediately.
Fire Fighting Measures of 1,4-dioxane:
Suitable Extinguishing Media:
Use dry chemical powder, alcohol-resistant foam, or carbon dioxide (CO2) to extinguish the fire.
Use water spray or fog only to cool fire-exposed containers.
Specific Hazards:
1,4-dioxane is highly flammable, and fire can produce toxic fumes, including carbon monoxide and carbon dioxide.
Containers may explode if exposed to heat, resulting in hazardous material release.
Protective Equipment:
Wear self-contained breathing apparatus (SCBA) and full protective gear to prevent exposure to toxic fumes and hot gases.
Special Fire Fighting Procedures:
Isolate the area, and keep unauthorized personnel at a safe distance.
Use water spray to cool down containers and prevent overpressure or rupture.
Accidental Release Measures of 1,4-dioxane:
Personal Precautions:
Evacuate all non-essential personnel from the area.
Ensure adequate ventilation to disperse vapors and avoid inhalation.
Wear appropriate personal protective equipment (PPE), including gloves, goggles, and a respirator if necessary.
Environmental Precautions:
Prevent the chemical from entering water sources or sewers.
Contain spills to minimize environmental impact.
Methods for Cleaning Up:
Use inert absorbent materials such as sand, earth, or vermiculite to soak up the liquid.
Carefully transfer the absorbed material to a suitable container for disposal.
Wash the affected area thoroughly after cleanup to remove any residual 1,4-dioxane.
Dispose of waste in accordance with local, regional, and national regulations.
Exposure Controls / Personal Protective Equipment of 1,4-dioxane:
Occupational Exposure Limits:
The recommended permissible exposure limit (PEL) for 1,4-dioxane is generally 1 ppm (parts per million) for an 8-hour workday and 40-hour workweek.
Some countries may have additional or stricter limits.
Engineering Controls:
Use local exhaust ventilation or general ventilation to maintain exposure below the recommended limits.
Ensure proper ventilation in confined spaces or areas where 1,4-dioxane vapors may accumulate.
Personal Protective Equipment (PPE):
Respiratory Protection:
Use a respirator with an organic vapor cartridge if exposure limits are exceeded.
Hand Protection:
Wear gloves made of nitrile or neoprene to prevent skin contact.
Eye Protection:
Use chemical safety goggles or face shields to protect the eyes from splashes or vapors.
Skin Protection:
Wear protective clothing, including lab coats or aprons, to avoid skin contact.
Workplace Hygiene:
Ensure that workers wash hands thoroughly after handling 1,4-dioxane and before eating or drinking.
Identifiers of 1,4-dioxane:
CAS Number: 123-91-1
Beilstein Reference: 102551
ChEBI: CHEBI:47032
ChEMBL: ChEMBL453716
ChemSpider: 29015
DrugBank: DB03316
ECHA InfoCard: 100.004.239
EC Number: 204-661-8
KEGG: C14440
PubChem CID: 31275
RTECS number: JG8225000
UNII: J8A3S10O7S
UN number: 1165
CompTox Dashboard (EPA): DTXSID4020533
InChI:
InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2 check
Key: RYHBNJHYFVUHQT-UHFFFAOYSA-N check
InChI=1/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
Key: RYHBNJHYFVUHQT-UHFFFAOYAN
SMILES: O1CCOCC1
CAS Number: 123-91-1
EC Number: 204-661-8
RTECS Number: KJ7700000
UN Number: 1165
Chemical Formula: C4H8O2
Molecular Weight: 88.11 g/mol
SMILES: O1CCOCC1
InChI: InChI=1S/C4H8O2/c1-2-5-3-4-6-1/h1-4H2
InChIKey: WZZAOSBQQZOYNJ-UHFFFAOYSA-N
Beilstein Registry Number: 1247163
Properties of 1,4-dioxane:
Grade: anhydrous
Quality Level: 200
Vapor density: 3 (vs air)
Vapor pressure:
27 mmHg ( 20 °C)
40 mmHg ( 25 °C)
Assay: 99.8%
Form: liquid
Autoignition temp.: 356 °F
Expl. lim.: 22 %
Impurities:
<0.003% water
<0.005% water (100 mL pkg)
Evapn. residue: <0.0003%
Refractive index: n20/D 1.422 (lit.)
pH: 6.0-8 (20 °C, 500 g/L)
bp: 100-102 °C (lit.)
mp: 10-12 °C (lit.)
Density: 1.034 g/mL at 25 °C (lit.)
SMILES string: C1COCCO1
InChI: 1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
InChI key: RYHBNJHYFVUHQT-UHFFFAOYSA-N
Molecular Weight: 88.11 g/mol
Appearance: Colorless liquid, sometimes with a faintly sweet odor.
Odor Threshold: Approximately 40 ppm (parts per million)
Boiling Point: 101.1°C (213.98°F)
Melting Point: -50.8°C (-59.4°F)
Density: 1.033 g/cm³ at 20°C
Solubility: Completely miscible in water, ethanol, acetone, ether, and other organic solvents.
Vapor Pressure: 13 mm Hg at 20°C
Vapor Density: 3.2 (Air = 1)
Flash Point: 11.2°C (52.2°F)
Autoignition Temperature: 258°C (496°F)
Viscosity: 1.3 cP at 20°C
Categories: Solvents,Semi-bulk solvents
Appearance (Form): Liquid
Assay: 99.8%
Melting point: 10-12 °C (lit.)
Boiling point: 100-102 °C(lit.)
Density: 1.034 g/mL at 25 °C(lit.)
Refractive index: n20/D 1.422(lit.)
Molecular Weight: 88.11
XLogP3: -0.3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 88.052429494
Monoisotopic Mass: 88.052429494
Topological Polar Surface Area: 18.5 Ų
Heavy Atom Count: 6
Complexity: 26.5
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Chemical formula: C4H8O2
Molar mass: 88.106 g·mol−1
Appearance: Colorless liquid
Odor: Mild, diethyl ether-like
Density: 1.033 g/mL
Melting point: 11.8 °C (53.2 °F; 284.9 K)
Boiling point: 101.1 °C (214.0 °F; 374.2 K)
Solubility in water: Miscible
Vapor pressure 29 mmHg (20 °C)
Magnetic susceptibility (χ): −52.16·10−6 cm3/mol
Thermochemistry of 1,4-dioxane:
Std molar entropy (So298): 196.6 J/K·mol
Std enthalpy of formation (ΔfH⦵298): −354 kJ/mol
Std enthalpy of combustion (ΔcH⦵298): −2363 kJ/mol
Specifications of 1,4-dioxane:
Assay (C₄H₈O₂): Approx. 99.8 %-
Water: max. 0.005 %
Residue After Evaporation: max. 0.0003 %
Related compounds of 1,4-dioxane:
Oxane
Trioxane
Tetroxane
Pentoxane
Names of 1,4-dioxane:
Preferred IUPAC name:
Dioxane anhydrous
Systematic IUPAC name:
1,4-Dioxacyclohexane
Other names:
[1,4]Dioxane
p-Dioxane
[6]-crown-2
Diethylene dioxide
Diethylene ether
Dioxane solvent
