Vinylphosphonic acid

Vinylphosphonic acid
Names
	IUPAC name Ethenylphosphonic acid
Identifiers
CAS Number	1746-03-8;
3D model (JSmol)	Interactive image;
ChemSpider	147591;
ECHA InfoCard	100.015.567
PubChem CID	168725;
CompTox Dashboard (EPA)	DTXSID40862745 ;
	InChI InChI=1S/C2H5O3P/c1-2-6(3,4)5/h2H,1H2,(H2,3,4,5) Key: ZTWTYVWXUKTLCP-UHFFFAOYSA-N; InChI=1/C2H5O3P/c1-2-6(3,4)5/h2H,1H2,(H2,3,4,5) Key: ZTWTYVWXUKTLCP-UHFFFAOYAX;
	SMILES C=CP(=O)(O)O;
Properties
Chemical formula	C2H5O3P
Molar mass	108.033 g·mol−1
Appearance	colourless solid
Density	1.37 g/mL at 20 °C[1]
Melting point	36 °C (97 °F; 309 K)[1]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Vinylphosphonic acid is an organophosphorus compound with the formula C₂H₃PO₃H₂.[2] It is a colorless, low-melting solid although commercial samples are often yellowish viscous liquids. It is used to prepare adhesives. As in other phosphonic acids, the phosphorus center is tetrahedral, being bonded to an organic group (vinyl in this case), two OH groups, and an oxygen.

Preparation

Vinylphosphonic acid can be prepared in several ways but the most common involves addition of PCl₃ to acetaldehyde:[3]

PCl₃ + CH₃CHO → CH₃CH(O⁻)PCl₃⁺

This adduct reacts with acetic acid:

CH₃CH(O⁻)PCl₃⁺ + 2 CH₃CO₂H → CH₃CH(Cl)PO(OH)₂ + 2 CH₃COCl

This chloride undergoes dehydrochlorination to afford the target:

CH₃CH(Cl)PO(OH)₂ → CH₂=CHPO(OH)₂ + HCl

Applications

Polymerization of vinylphosphonic acid gives polyvinylphosphonic acid, which is best known for promoting adhesion between organic and inorganic phases. Such interfaces exist between coatings and the substrates to which they are applied. Both vinylphosphonic acid homopolymer and its copolymers are the basis of many products which have found applications in scale and corrosion treatment. Polyvinylphosphonic acid is an essential component for the polymer electrolyte membranes used in fuel cell development, in the medical field as dental cements, hydrogels for drug delivery, and components in biomimetic mineralization.[3]

References

"Vinylphosphonic acid". Sigma-Aldrich.
Svara, J.; Weferling, N.; Hofmann, T. "Phosphorus Compounds, Organic," In 'Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2008. doi:10.1002/14356007.a19_545.pub2.
Lavinia, M.; Gheorghe, I. (2010). "Poly(vinylphosphonic acid) and its derivatives". Progress in Polymer Science. 35 (8): 1078–1092. doi:10.1016/j.progpolymsci.2010.04.001.

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[Aldrich-1] "Vinylphosphonic acid". Sigma-Aldrich.

[Svara-2] Svara, J.; Weferling, N.; Hofmann, T. "Phosphorus Compounds, Organic," In 'Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2008. doi:10.1002/14356007.a19_545.pub2.

[Lavinia-3] Lavinia, M.; Gheorghe, I. (2010). "Poly(vinylphosphonic acid) and its derivatives". Progress in Polymer Science. 35 (8): 1078–1092. doi:10.1016/j.progpolymsci.2010.04.001.