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Organophosphate

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Organophosphate

In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid. Organophosphates are best known for their use as pesticides.

Like most functional groups, organophosphates occur in a diverse range of forms, with important examples including key biomolecules such as DNA, RNA and ATP, as well as many insecticides, herbicides, nerve agents and flame retardants. OPEs have been widely used in various products as flame retardants, plasticizers, and performance additives to engine oil. The low cost of production and compatibility to diverse polymers made OPEs to be widely used in industry including textile, furniture, electronics as plasticizers and flame retardants. These compounds are added to the final product physically rather than by chemical bond. Due to this, OPEs leak into the environment more readily through volatilization, leaching, and abrasion. OPEs have been detected in diverse environmental compartments such as air, dust, water, sediment, soil and biota samples at higher frequency and concentration.

The popularity of OPEs as flame retardants came as a substitution for the highly regulated brominated flame retardants.

Organophosphates are a class of compounds encompassing a number of distinct but closely related function groups. These are primarily the esters of phosphoric acid and can be mono‑esters, di‑esters or tri‑esters depending on the number of attached organic groups (abbreviated as 'R' in the image below). In general man‑made organophosphates are most often triesters, while biological organophosphates are usually mono- or di-esters. The hydrolysis of triesters can form diesters and monoesters.

In the context of pesticides, derivatives of organophosphates such as organothiophosphates (P=S) or phosphorodiamidates (P-N) are included as being organophosphates. The reason is that these compound are converted into organophosphates biologically.

In biology the esters of diphosphoric acid and triphosphoric acid are generally included as organophosphates. The reason is again a practical one, as many cellular processes involve the mono-, di- and tri- phosphates of the same compound. For instance, the phosphates of adenosine (AMP, ADP, ATP) play a key role in many metabolic processes.

Phosphorus oxychloride reacts readily with alcohols to give organophosphates. This is the dominant industrial route and is responsible for almost all organophosphate production. Aluminum trichloride or magnesium chloride are often employed as catalysts.

When aliphatic alcohols are used the HCl by-product can react with the phosphate esters to give organochlorides and a lower ester.

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