1,4-Dioxane

Description

1,4-dioxane is a clear liquid with ether-like odour. It is highly flammable and forms explosive peroxides in storage (rate of formation increased by heating, evaporation, or exposure to light). 1,4-Dioxane is incompatible with oxidising agents, oxygen, halogens, reducing agents, and moisture. Industrial applications of 1,4-dioxane are extensive, for instance, as solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, and some dyes; as a solvent for paper, cotton, and textile processing; and for various organic and inorganic compounds and products. It is also used in automotive coolant liquid and in shampoos and other cosmetics as a degreasing agent and as a component of paint and varnish. Human exposures to 1,4-dioxane have been traced to multiple occupations and breathing of contaminated workplace air and drinking polluted water. Industrial uses of 1,4-dioxane are very many. For instance, it is used as solvent for celluloses, resins, lacquers, synthetic rubbers, adhesives, sealants, fats, oils, dyes, and protective coatings; as a stabiliser for chlorinated solvents and printing inks; and as a wetting and dispersing agent in textile processing agrochemicals and pharmaceuticals, in different processing of solvent-extraction processes, and in the preparation and manufacture of detergents.

Description

March of this year was “Solvent Month” for Molecule of the Week. Another commonly used solvent is 1,4-dioxane, usually referred to simply as dioxane.1 It is a cyclic diether that has an odor similar to that of its more volatile cousin, diethyl ether.
In 1928, IG Farbenindustrie (precursor to BASF) patented a manufacturing process for dioxane in which diethylene glycol is heated with a small amount of sulfuric acid. Today, it is still produced in much the same way. It is used industrially as a solvent for cellulose esters and ethers, adhesives, inks, and many other materials.
Dioxane, however, is coming under regulatory pressure because of health and environmental concerns:
1. Structural isomers 1,2- and 1,3-dioxane have been prepared, but they are not commercial products.

Description

Dioxane is a common aprotic solvent in organic chemistry. It is an ethereal solvent which is miscible with water. Dioxane can sometimes be a useful alternative to THF when a higher boiling point is desired. Commercially available 4M HCl in dioxane is one of the most frequently encountered applications of dioxane as a solvent. The use of 4M HCl in dioxane is common for boc deprotections.

The Uses of 1,4-Dioxane

The Iodo compound (308 mg, 0.513 mmol), the boronic ester (194 mg, 0.641 mmol), K3PO4 (327 mg, 1.539 mmol), XPhos (14.67 mg, 0.031 mmol), and Pd2(dba)3 (14.09 mg, 0.015 mmol) were combined in a microwave vial. The vial was purged with argon, after which time was added dioxane (3 mL) and H2O (0.5 mL) The reaction was irradiated in a microwave reactor at 120 C for 10 min. Additional boronic ester (50 mg) was added and the mixture was irradiated at 120 C for another 10 min. The mixture was then treated with aq 1N NaOH and extracted with EtOAc (50 mL). The org layer was dried (MgSO4), concentrated, and purified by flash chromatography (20% MeOH/DCM) to provide the product as a dark yellow solid. [177 mg, 53%]

The Uses of 1,4-Dioxane

1,4-Dioxane, the six-member cyclic diether, is used as an aluminum inhibitor in chlorinated solvents like 1,1,1-trichloroethane and as a solvent for certain resins and polymers.

What are the applications of Application

1,4-Dioxane is a compound also known as Diethylene oxide