1,4-dioxane solution, mainly composed of 1,4-dioxane, is an organic compound with a molecular formula of C4H8O2, CAS 123-91-1, and a molecular weight of 88.11. It is a colorless and transparent liquid with a slight ether like odor or subtle sweetness. Can mix with water and most organic solvents to form an azeotropic mixture. The azeotropic ratio is 81.6% for dioxane, and the azeotropic temperature is 87.8 ℃. In addition, the product stored for a long time may contain peroxides and diethanol formaldehyde. It is a flammable liquid that needs to be stored and used under specific conditions to prevent the occurrence of fire and explosion accidents. Mainly used as a solvent for nitrocellulose, celluloid, cellulose resin, vegetable oil, mineral oil, and oil soluble dyes, it can be used as a dispersant for dyes, a dispersant for wood coloring agents, and a solvent for oil soluble dyes. It is also used to manufacture paints, varnishes, plasticizers, wetting agents, polishing agents, paint removers, perfume, preservatives, fumigants, disinfectants, deodorants and medical supplies. It can also form coordination compounds with sulfur trioxide and be used as a sulfating agent in the synthesis of many compounds; It can also be used as a high-purity metal surface treatment agent, etc.
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Chemical Formula |
C4H8O2 |
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Exact Mass |
88 |
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Molecular Weight |
88 |
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m/z |
88 (100.0%), 89 (4.3%) |
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Elemental Analysis |
C, 54.53; H, 9.15; O, 36.32 |
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Synthesis of 1,4-dioxane solution:
1. It is mainly produced by dehydration of ethylene glycol under acid catalysis or direct dimerization of ethylene oxide in the presence of acid catalyst. The synthesized crude product is added with alkali to remove acidic substances and water, filtered by suction, and then the filtrate is pumped into the distillation kettle to obtain 1,4-dioxane pure product. The raw materials ethylene oxide and ethylene glycol used in these two processes have high prices and low yields; The acid catalyst is used for both of them. The post-treatment is complicated and the pollution is heavy. In addition, ethylene oxide is a flammable and explosive hazardous chemical, which is not convenient for transportation and use.
2. 1,4-dioxane was synthesized from chloroethoxyethanol. 1,4-dioxane was synthesized from chloroethoxyethanol and dilute aqueous solution of strong alkali (such as alkali metal or alkaline earth metal hydroxide). The raw material alkali price of this method is low, and chloroethoxyethanol is a by-product of chloroethanol production, and the cost is low; The reaction device is simple and easy to industrialize; The product has high yield and purity, which is of great significance for improving economic benefits.
Reaction principle: 1,4-dioxane is synthesized by reacting chloroethoxyethanol with dilute aqueous solution of inorganic strong base (such as alkali metal or alkaline earth metal hydroxide) under normal pressure or pressure. The main reaction equation is as follows:
3. In the process of producing ethylene glycol, there are many by-products of diethylene glycol (also known as diethylene glycol), which can be used to synthesize advanced solvent 1,4-dioxane.
Reaction equation:
1,4-dioxane solution is a colorless and transparent liquid organic compound that has a wide range of applications in the chemical industry due to its good solubility and chemical stability.
Application as a solvent
Basic solvent
It is an excellent solvent that can dissolve various organic compounds, including cellulose acetate, resin, vegetable oil, mineral oil, etc. This solubility makes 1,4-dioxane widely used in industries such as paint, coatings, and inks. It can be used as a solvent for these products, helping to regulate the viscosity, fluidity, and drying speed of the products, thereby improving their quality and performance.
Dyes and pigment solvents
In the dye and pigment industry, it can be used as a dispersant and solvent. It can help dyes and pigments disperse better in the medium, improving the uniformity and quality of dyeing and coloring. At the same time, it can also serve as a solvent for oil soluble dyes, helping them dissolve in oil for better application.
Manufacturing of special chemicals
When manufacturing certain special chemicals, they are often used as solvents or reaction media. For example, in the extraction process of pharmaceuticals and pesticides, it can serve as a solvent to assist in the extraction of active ingredients. In addition, it can also be used to prepare certain specific compounds, such as by forming coordination compounds with sulfur trioxide and participating in the synthesis of compounds as a sulfating agent.
Application in synthetic materials
Polyurethane synthetic leather
In the production process of polyurethane synthetic leather, it can be used as a reaction solvent. It can help polyurethane raw materials mix and react better, thereby improving the quality and performance of synthetic leather. In addition, it can also be used as a foaming agent of polyurethane foam to help foam expand and solidify better.
Other synthetic materials
In addition to polyurethane synthetic leather, it can also be used in the manufacturing process of other synthetic materials. For example, it can serve as a reaction solvent for amino acid synthetic leather, helping amino acid raw materials react and solidify better. In addition, it can also be used to prepare certain specific polymers or resin materials.
Application in Laboratory and Scientific Research
Catalyst carrier
In laboratories and scientific research, it can be used as a carrier for catalysts. It can help the catalyst disperse better in the reaction system, thereby improving the efficiency and selectivity of the catalytic reaction. For example, in the iridium catalyzed olefin transfer hydrogenation process using this substance as a hydrogen source, serving as a carrier can promote the reaction and improve the purity of the product.
Reaction medium and solvent
It can also be used as a reaction medium or solvent for certain chemical reactions in the laboratory. Its chemical stability and solubility make it suitable for various types of chemical reactions, including oxidation, reduction, addition, substitution, etc. In the laboratory, researchers can utilize these characteristics to design and optimize chemical reaction conditions, thereby preparing the desired compounds or materials.
Other applications
Safe transportation of chlorinated hydrocarbons in aluminum containers
It can also be used as a stabilizer to assist in the safe transportation of chlorinated hydrocarbons in aluminum containers. It can prevent dangerous situations such as leakage or explosion of chlorinated hydrocarbons during transportation, thereby ensuring the safety and reliability of the transportation process.
Emulsifiers and detergents
Has a certain emulsifying effect and can be used as an emulsifier. It can help two immiscible liquids mix better together to form a stable emulsion. In addition, it can also be used as a descaling agent to help remove various dirt and grease.
Physicochemical Properties in Aqueous Solutions
► Basic Properties
1,4-Dioxane is a polar aprotic solvent with a boiling point of 101.1°C and a density of 1.033 g/mL at 25°C. Its solubility in water is effectively unlimited, forming homogeneous mixtures even at high concentrations. This miscibility arises from hydrogen bonding between water molecules and the ether oxygen atoms in 1,4-dioxane, though molecular dynamics simulations reveal that 1,4-dioxane disrupts water's hydrogen-bond network, reducing the number of water-water hydrogen bonds and altering solution viscosity.
► Partitioning Behavior
The compound's low octanol-water partition coefficient (log Kow = -0.27) indicates hydrophilicity, limiting its adsorption to soils and sediments. Its organic carbon partition coefficient (log Koc = 1.23) further suggests minimal sorption to organic matter, enhancing its mobility in groundwater. These properties complicate containment efforts, as 1,4-dioxane can migrate rapidly through aquifers.
► Stability and Reactivity
1,4-Dioxane is resistant to hydrolysis, photolysis, and biodegradation under ambient conditions. Advanced oxidation processes (AOPs) using hydroxyl radicals (·OH) are required for its degradation, though efficiency depends on reaction kinetics and matrix interference. For example, in aqueous solutions, ·OH radicals react with 1,4-dioxane at a rate constant of 1.2 × 10⁹ M⁻¹s⁻¹, but competing reactions with background organics can reduce treatment efficacy.
Industrial Applications and Historical Use
► Solvent Stabilizer
From the 1950s to the 1990s, 1,4-dioxane was added to chlorinated solvents like TCA to prevent decomposition into corrosive hydrochloric acid. An estimated 90% of produced 1,4-dioxane was consumed for this purpose. After TCA's phase-out, residual 1,4-dioxane from solvent disposal remains a primary contamination source at industrial sites.
► Pharmaceuticals and Cosmetics
1,4-Dioxane is a trace byproduct in the synthesis of polyethylene glycol (PEG) and ethoxylated surfactants, which are used in shampoos, detergents, and pharmaceuticals. Regulatory efforts, such as the FDA's guidance on cosmetic impurities, have reduced its presence in consumer products, though historical contamination persists in wastewater effluents.
► Laboratories and Specialty Chemicals
As a versatile solvent, 1,4-dioxane is used in research laboratories for reactions requiring anhydrous conditions. It also serves as a reaction medium in polymerization and as a stabilizer in adhesives and sealants.
1,4-Dioxane solutions play a pivotal role in industrial processes but pose significant environmental and health risks. While regulatory efforts have curbed its use in consumer products, groundwater contamination remains a persistent challenge. Advanced remediation technologies and safer alternatives are critical for mitigating exposure. As industries transition to sustainable practices, the future of 1,4-dioxane hinges on balancing its utility with responsible management to protect public health and ecosystems.
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