Diethyl dithiophosphoric acid, sometimes mistakenly called diethyl dithiophosphate, is the organophosphorus compound with the formula (C2H5O)2PS2H. It is the processor for production of the organophosphate insecticide Terbufos. Although samples can appear dark, it is a colorless liquid.[1]
It is prepared by treating phosphorus pentasulfide with ethanol:[2]
- P2S5 + 4 C2H5OH → 2 (C2H5O)2PS2H + H2S
Reactions
Diethyl- and dimethyl dithiophosphoric acids react with bases. The results of this neutralization reaction are salts, e.g., ammonium diethyl dithiophosphate.[3]
Diethyl dithiophosphoric acid reacts with zinc oxide to give zinc dithiophosphate, which is used as an oil additive:[4]
- ZnO + 2 (C2H5O)2PS2H → [(C2H5O)2PS2]2Zn + H2O
Oxidation of dialkoxydithiophosphoric acids with iodine gives the disulfides:[5]
- 2 (RO)2PS2H + I2 → (RO)2P(S)S−SP(S)(OR)2 + 2 HI
See also
References
- ^ J. Svara, N. Weferling, T. Hofmann "Phosphorus Compounds, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a19_545.pub2
- ^ Lefferts, J. L.; Molloy, K. C.; Zuckerman, J. J.; Haiduc, I.; Guta, C.; Ruse, D. (1980). "Oxy and thio phosphorus acid derivatives of tin. 1. Triorganotin(IV) dithiophosphate esters". Inorganic Chemistry. 19 (6): 1662–1670. doi:10.1021/ic50208a046.
- ^ Okuniewski, Andrzej; Becker, Barbara (2011). "Ammonium O,O′-diethyl dithiophosphate". Acta Crystallogr. E. 67 (7): o1749 – o1750. Bibcode:2011AcCrE..67o1749O. doi:10.1107/S1600536811022811. PMC 3151957. PMID 21837134.
- ^ H. Spikes "The history and mechanisms of ZDDP" Tribology Letters, Vol. 17, No. 3, October 2004. doi:10.1023/B:TRIL.0000044495.26882.b5.
- ^ Perlikowska, Wieslawa; Gouygou, Maryse; Mikolajczyk, Marian; Daran, Jean-Claude (2004). "Enantiomerically Pure Disulfides: Key Compounds in the Kinetic Resolution of Chiral PIII-Derivatives with Stereogenic Phosphorus". Tetrahedron: Asymmetry. 15 (22): 3519–3529. doi:10.1016/j.tetasy.2004.09.014.
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