Phosphorus pentasulfide is the

inorganic compound In chemistry, an inorganic compound is typically a chemical compound that lacks carbon–hydrogen bonds, that is, a compound that is not an organic compound. The study of inorganic compounds is a subfield of chemistry known as '' inorganic chemis ...

with the formula (

monomer In chemistry, a monomer ( ; '' mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization. Classification ...

) or (

dimer Dimer may refer to: * Dimer (chemistry), a chemical structure formed from two similar sub-units ** Protein dimer, a protein quaternary structure ** d-dimer * Dimer model, an item in statistical mechanics, based on ''domino tiling'' * Julius Dimer ( ...

). This yellow solid is the one of two

phosphorus sulfide Phosphorus sulfides comprise a family of inorganic compounds containing only phosphorus and sulfur. These compounds have the formula with ''n'' ≤ 10. Two are of commercial significance, phosphorus pentasulfide (), which is made on a kiloton scal ...

s of commercial value. Samples often appear greenish-gray due to impurities. It is soluble in

carbon disulfide Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical n ...

but reacts with many other

solvents A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

such as

alcohols In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is ...

, DMSO, and DMF.

Structure and synthesis

Its

tetrahedral In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all the ...

molecular structure is similar to that of

adamantane Adamantane is an organic compound with a formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the ...

and almost identical to the structure of

phosphorus pentoxide Phosphorus pentoxide is a chemical compound with molecular formula P4 O10 (with its common name derived from its empirical formula, P2O5). This white crystalline solid is the anhydride of phosphoric acid. It is a powerful desiccant and dehydra ...

. Phosphorus pentasulfide is obtained by the reaction of liquid white phosphorus () with

sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formul ...

above 300 °C. The first synthesis of by Berzelius in 1843 was by this method. Alternatively, can be formed by reacting elemental sulfur or

pyrite The mineral pyrite (), or iron pyrite, also known as fool's gold, is an iron sulfide with the chemical formula Iron, FeSulfur, S2 (iron (II) disulfide). Pyrite is the most abundant sulfide mineral. Pyrite's metallic Luster (mineralogy), lust ...

, , with ferrophosphorus, a crude form of (a byproduct of white phosphorus () production from

phosphate rock Phosphorite, phosphate rock or rock phosphate is a non-detrital sedimentary rock that contains high amounts of phosphate minerals. The phosphate content of phosphorite (or grade of phosphate rock) varies greatly, from 4% to 20% phosphorus pento ...

): : :

Applications

Approximately 150,000 tons of are produced annually. The compound is mainly converted to other derivatives for use as lubrication additives such as

zinc dithiophosphate Zinc dialkyldithiophosphates (often referred to as ZDDP) are a family of coordination compounds developed in the 1940s that feature zinc bound to the anion of a dialkyldithiophosphoric salt (e.g., ammonium diethyl dithiophosphate). These uncharge ...

s. It is widely used in the production of

sodium dithiophosphate Sodium dithiophosphate is the salt with the formula Na3PS2O2. It is usually supplied as the hydrated solid or as an aqueous solution together with other thiophosphates such as sodium monothiophosphate and sodium trithiophosphate. It is a colo ...

for applications as a flotation agent in the concentration of

molybdenite Molybdenite is a mineral of molybdenum disulfide, Mo S2. Similar in appearance and feel to graphite, molybdenite has a lubricating effect that is a consequence of its layered structure. The atomic structure consists of a sheet of molybdenum ato ...

minerals. It is also used in the production of pesticides such as

Parathion Parathion, also called parathion-ethyl or diethyl parathion and locally known as "Folidol", is an organophosphate insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms, inclu ...

and

Malathion Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion. Pesticide use Malathion is a pe ...

. It is also a component of some amorphous solid

electrolyte An electrolyte is a medium containing ions that is electrically conducting through the movement of those ions, but not conducting electrons. This includes most soluble salts, acids, and bases dissolved in a polar solvent, such as water. Upon ...

s (e.g. -) for some types of

lithium batteries Lithium battery may refer to: * Lithium metal battery, a non-rechargeable battery with lithium as an anode ** Rechargeable lithium metal battery, a rechargeable counterpart to the lithium metal battery * Lithium-ion battery, a rechargeable batte ...

. Phosphorus pentasulfide is a

dual-use In politics, diplomacy and export control, dual-use items refers to goods, software and technology that can be used for both civilian and military applications.

material, for the production of early insecticides such as Amiton and also for the manufacture of the related VX

nerve agent Nerve agents, sometimes also called nerve gases, are a class of organic chemicals that disrupt the mechanisms by which nerves transfer messages to organs. The disruption is caused by the blocking of acetylcholinesterase (AChE), an enzyme that ...

Reactivity

Due to hydrolysis by atmospheric moisture, evolves

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 under ...

, thus is associated with a rotten egg odour. Aside from ,

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...

of eventually gives

phosphoric acid Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, w ...

: : Other mild

nucleophiles In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...

react with , including

and

amines In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such ...

. Aromatic compounds such as

anisole Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound i ...

ferrocene Ferrocene is an organometallic compound with the formula . The molecule is a complex consisting of two cyclopentadienyl rings bound to a central iron atom. It is an orange solid with a camphor-like odor, that sublimes above room temperature, ...

and 1-methoxynaphthalene react to form

1,3,2,4-dithiadiphosphetane 2,4-disulfides 1,3,2,4-Dithiadiphosphetane 2,4-disulfides are a class of four-membered ring compounds which contain a PS ring, many of these compounds are able to act as sources of the dithiophosphine ylides. The most well known example of this class of compoun ...

such as Lawesson's reagent. is used as a thionation reagent. Reactions of this type require refluxing solvents such as

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...

, dioxane, or

acetonitrile Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile ( hydrogen cyanide is a simpler nitrile, but the cyanide anion is not clas ...

with dissociating into . Some

ketones In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double b ...

esters In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

, and

imides In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis. In terms of commercial applications, ...

are converted to the corresponding

thiocarbonyl In organic chemistry, thioketones (; also known as thiones or thiocarbonyls) are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of , thioketones have the structu ...

Amides In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...

give

thioamide A thioamide (rarely, thionamide, but also known as thiourylenes) is a functional group with the general structure R–CS–NR′R″, where R, R′, and R″ are organic groups. They are analogous to amides but they exhibit greater multiple bond ch ...

s. With 1,4-diketones the reagent forms

thiophene Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reacti ...

s. It is also used to deoxygenate sulfoxides. The use of has been displaced by the aforementioned Lawesson's reagent. reacts with

pyridine Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid w ...

to form the complex .

References

{{Phosphorus compounds Inorganic phosphorus compounds Sulfides Adamantane-like molecules