Diethyl dithiophosphoric acid

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Diethyl dithiophosphoric acid
Diethyl-dithiophosphoric-acid-from-AHRLS-2011-2D.png
Diethyl-dithiophosphoric-acid-from-AHRLS-2011-3D-balls.png
Names
Preferred IUPAC name
O,O-Diethyl hydrogen phosphorodithioate
Other names
O,O-Diethyl dithiophosphoric acid; Diethyl dithiophosphate; Diethyl phosphorodithioate; Diethyl ester of phosphorodithioic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.506 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-055-9
PubChem CID
RTECS number
  • TD7350000
UNII
  • InChI=1S/C4H11O2PS2/c1-3-5-7(8,9)6-4-2/h3-4H2,1-2H3,(H,8,9)
    Key: IRDLUHRVLVEUHA-UHFFFAOYSA-N
  • InChI=1/C4H11O2PS2/c1-3-5-7(8,9)6-4-2/h3-4H2,1-2H3,(H,8,9)
    Key: IRDLUHRVLVEUHA-UHFFFAOYAW
  • CCOP(=S)(OCC)S
Properties
C4H11O2PS2
Molar mass 186.22 g·mol−1
Appearancecolorless liquid
Melting point <0 °C (32 °F; 273 K)
Boiling point 66 °C (151 °F; 339 K) at 1 mmHg
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg
Danger
H301, H311, H314, H330
P260, P264, P270, P271, P280, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P361, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
2
1
Flash point 82 °C (180 °F; 355 K)
538 °C (1,000 °F; 811 K)
Lethal dose or concentration (LD, LC):
500 mg/kg (rabbit, dermal)
4510 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

Contents

It is prepared by treating phosphorus pentasulfide with ethanol: [2]

P2S5 + 4 C2H5OH → 2 (C2H5O)2PS2H + H2S

Reactions

Structure of a typical zinc bis(dithiophosphate) complex (L = ligand). Zn(S2P(OR)2)2L.svg
Structure of a typical zinc bis(dithiophosphate) complex (L = ligand).

Diethyl- and dimethyl dithiophosphoric acids react with bases. The results of this neutralization reaction are salts, e.g., ammonium diethyl dithiophosphate. [4]

Diethyl dithiophosphoric acid reacts with zinc oxide to give zinc dithiophosphate, which is used as an oil additive: [5]

ZnO + 2 (C2H5O)2PS2H → [(C2H5O)2PS2]2Zn + H2O

Oxidation of dialkoxydithiophosphoric acids with iodine gives the disulfides: [6]

2 (RO)2PS2H + I2 → (RO)2P(S)S−SP(S)(OR)2 + 2 HI

See also

References

  1. ↑ 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
  2. ↑ 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.
  3. ↑ Ellis, Carol A.; Ng, Seik Weng; Tiekink, Edward R. T. (2007). "μ-1,4-Diazabicyclo[2.2.2]octane-κ2N: N ′-bis[bis( O , O ′-diisopropyl dithiophosphato-κ2S , S ′)zinc(II)]". Acta Crystallographica Section e Structure Reports Online. 63: m108 –m110. doi:10.1107/S1600536806052007.
  4. ↑ 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.
  5. ↑ H. Spikes "The History and Mechanisms of ZDDP" Tribology Letters, Vol. 17, No. 3, October 2004. doi : 10.1023/B:TRIL.0000044495.26882.b5.
  6. ↑ 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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