Organophosphate

This article is about the organic derivatives of the phosphate ion. For the inorganic ion, see phosphate. For all organic compound incorporating phosphorus, see organophosphorus chemistry.
General chemical structure of the organophosphate functional group

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.[1] 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,[2] 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.[3] Due to this, OPEs leak into the environment more readily through volatilization, leaching, and abrasion.[4] OPEs have been detected in diverse environmental compartments such as air, dust, water, sediment, soil and biota samples at higher frequency and concentration.[1][4]

The popularity of OPEs as flame retardants came as a substitution for the highly regulated brominated flame retardants.[5]

  1. ^ a b Greaves, Alana K.; Letcher, Robert J.; Chen, Da; McGoldrick, Daryl J.; Gauthier, Lewis T.; Backus, Sean M. (2016-10-01). "Retrospective analysis of organophosphate flame retardants in herring gull eggs and relation to the aquatic food web in the Laurentian Great Lakes of North America". Environmental Research. 150: 255–263. Bibcode:2016ER....150..255G. doi:10.1016/j.envres.2016.06.006. ISSN 0013-9351. PMID 27322497.
  2. ^ Ung, Sosthène P.-M.; Li, Chao-Jun (2023). "From rocks to bioactive compounds: a journey through the global P( v ) organophosphorus industry and its sustainability". RSC Sustainability. 1 (1): 11–37. doi:10.1039/D2SU00015F.
  3. ^ Wang, Xiaolei; Zhong, Wenjue; Xiao, Bowen; Liu, Qing; Yang, Liping; Covaci, Adrian; Zhu, Lingyan (2019-04-01). "Bioavailability and biomagnification of organophosphate esters in the food web of Taihu Lake, China: Impacts of chemical properties and metabolism". Environment International. 125: 25–32. doi:10.1016/j.envint.2019.01.018. hdl:10067/1585250151162165141. ISSN 0160-4120. PMID 30690428.
  4. ^ a b Wei, Gao-Ling; Li, Ding-Qiang; Zhuo, Mu-Ning; Liao, Yi-Shan; Xie, Zhen-Yue; Guo, Tai-Long; Li, Jun-Jie; Zhang, Si-Yi; Liang, Zhi-Quan (January 2015). "Organophosphorus flame retardants and plasticizers: Sources, occurrence, toxicity and human exposure". Environmental Pollution. 196: 29–46. doi:10.1016/j.envpol.2014.09.012. PMID 25290907.
  5. ^ Veen, Ike van der; Boer, Jacob de (2012). "Phosphorus flame retardants: Properties, production, environmental occurrence, toxicity and analysis". Chemosphere. 88 (10): 1119–1153. Bibcode:2012Chmsp..88.1119V. doi:10.1016/j.chemosphere.2012.03.067. PMID 22537891.