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.
This chloride undergoes dehydrochlorination to afford the target:
CH3CH(Cl)PO(OH)2 → CH2=CHPO(OH)2 + HCl
Applicationsedit
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]
^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.
^ abLavinia, 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.
April 14, 2024
vinylphosphonic, acid, organophosphorus, compound, with, formula, c2h3po3h2, colorless, melting, solid, although, commercial, samples, often, yellowish, viscous, liquids, used, prepare, adhesives, other, phosphonic, acids, phosphorus, center, tetrahedral, bein. 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 Vinylphosphonic acid NamesPreferred IUPAC name Ethenylphosphonic acidIdentifiersCAS Number 1746 03 83D model JSmol Interactive imageChemSpider 147591ECHA InfoCard 100 015 567PubChem CID 168725CompTox Dashboard EPA DTXSID40862745InChI InChI 1S C2H5O3P c1 2 6 3 4 5 h2H 1H2 H2 3 4 5 Key ZTWTYVWXUKTLCP UHFFFAOYSA NSMILES C CP O O OPropertiesChemical formula C 2H 5O 3PMolar mass 108 033 g mol 1Appearance colourless solidDensity 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 referencesPreparation editVinylphosphonic acid can be prepared in several ways but the most common involves the 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 CH3COClThis chloride undergoes dehydrochlorination to afford the target CH3CH Cl PO OH 2 CH2 CHPO OH 2 HClApplications editPolymerization 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 edit a b 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 a b 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 Retrieved from https en wikipedia org w index php title Vinylphosphonic acid amp oldid 1129453883, wikipedia, wiki, book, books, library,
