Diethyl sulfide ( British English: diethyl sulphide) is an

organosulfur compound Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfu ...

with the chemical formula . It is a colorless, malodorous liquid. Although a common thioether, it has few applications.

Preparation

Diethyl sulfide is a by-product of the commercial production of ethanethiol, which is prepared by the reaction of

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...

with

hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is poisonous, corrosive, and flammable, with trace amounts in ambient atmosphere having a characteristic foul odor of rotten eggs. The unde ...

over an alumina-based catalyst. The amount of diethyl sulfide produced can be controlled by varying the ratio of hydrogen sulfide to ethylene.

Occurrence

Diethyl sulfide has been found to be a constituent of the odor of

durian The durian (, ) is the edible fruit of several tree species belonging to the genus ''Durio''. There are 30 recognised ''Durio'' species, at least nine of which produce edible fruit. ''Durio zibethinus'', native to Borneo and Sumatra, is the onl ...

fruit and as a constituent found in volatiles from potatoes.

Reactions

Diethyl sulfide is a Lewis base, classified as a soft ligand (see also ECW model).Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots. With bromine, it forms the bromosulfonium salt: : A typical coordination complex is ''cis''-PtCl₂(SEt₂)₂. CIKXIE

References

{{reflist, 1 Thioethers Solvents Foul-smelling chemicals