Vinylphosphonic acid

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Vinylphosphonic acid
Vinylphosphonic acid.svg
Names
Preferred IUPAC name
Ethenylphosphonic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.567 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=1S/C2H5O3P/c1-2-6(3,4)5/h2H,1H2,(H2,3,4,5)
    Key: ZTWTYVWXUKTLCP-UHFFFAOYSA-N
  • C=CP(=O)(O)O
Properties
C2H5O3P
Molar mass 108.033 g·mol−1
Appearancecolourless 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).

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.

Contents

Preparation

Vinylphosphonic 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 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]

Related Research Articles

<span class="mw-page-title-main">Phosphorus</span> Chemical element, symbol P and atomic number 15

Phosphorus is a chemical element with the symbol P and atomic number 15. Elemental phosphorus exists in two major forms, white phosphorus and red phosphorus, but because it is highly reactive, phosphorus is never found as a free element on Earth. It has a concentration in the Earth's crust of about one gram per kilogram. In minerals, phosphorus generally occurs as phosphate.

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class provides common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.

In polyatomic cations with the chemical formula PR+
4
. These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.

<span class="mw-page-title-main">Phosphorus pentachloride</span> Chemical compound

Phosphorus pentachloride is the chemical compound with the formula PCl5. It is one of the most important phosphorus chlorides, others being PCl3 and POCl3. PCl5 finds use as a chlorinating reagent. It is a colourless, water-sensitive and moisture-sensitive solid, although commercial samples can be yellowish and contaminated with hydrogen chloride.

<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

<span class="mw-page-title-main">Triphenylphosphine</span> Chemical compound

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

Phosphorous acid (or phosphonic acid (singular)) is the compound described by the formula H3PO3. This acid is diprotic (readily ionizes two protons), not triprotic as might be suggested by this formula. Phosphorous acid is an intermediate in the preparation of other phosphorus compounds. Organic derivatives of phosphorous acid, compounds with the formula RPO3H2, are called phosphonic acids.

<span class="mw-page-title-main">Phosphorus pentoxide</span> Chemical compound

Phosphorus pentoxide is a chemical compound with molecular formula P4O10 (with its common name derived from its empirical formula, P2O5). This white crystalline solid is the anhydride of phosphoric acid. It is a powerful desiccant and dehydrating agent.

<span class="mw-page-title-main">Phosphoryl chloride</span> Chemical compound

Phosphoryl chloride is a colourless liquid with the formula POCl3. It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide. It is mainly used to make phosphate esters such as tricresyl phosphate.

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In organic chemistry, phosphonates or phosphonic acids are organophosphorus compounds containing C−PO(OR)2 groups. Phosphonic acids, typically handled as salts, are generally nonvolatile solids that are poorly soluble in organic solvents, but soluble in water and common alcohols.

<span class="mw-page-title-main">Phosphite ester</span> Organic compound with the formula P(OR)3

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<span class="mw-page-title-main">Phosphine oxide</span> Class of chemical compounds

Phosphine oxides are phosphorus compounds with the formula OPX3. When X = alkyl or aryl, these are organophosphine oxides. Triphenylphosphine oxide is an example. An inorganic phosphine oxide is phosphoryl chloride (POCl3).

<span class="mw-page-title-main">Hexachlorophosphazene</span> Chemical compound

Hexachlorophosphazene is an inorganic compound with the formula (NPCl2)3. The molecule has a cyclic, unsaturated backbone consisting of alternating phosphorus and nitrogen centers, and can be viewed as a trimer of the hypothetical compound N≡PCl2. Its classification as a phosphazene highlights its relationship to benzene. There is large academic interest in the compound relating to the phosphorus-nitrogen bonding and phosphorus reactivity.

<span class="mw-page-title-main">Thiophosphoryl chloride</span> Chemical compound

Thiophosphoryl chloride is an inorganic compound with the formula PSCl3. It is a colorless pungent smelling liquid that fumes in air. It is synthesized from phosphorus chloride and used to thiophosphorylate organic compounds, such as to produce insecticides.

<span class="mw-page-title-main">Triethyl phosphite</span> Chemical compound

Triethyl phosphite is an organophosphorus compound with the formula P(OCH2CH3)3, often abbreviated P(OEt)3. It is a colorless, malodorous liquid. It is used as a ligand in organometallic chemistry and as a reagent in organic synthesis

<span class="mw-page-title-main">Tetrakis(hydroxymethyl)phosphonium chloride</span> Chemical compound

Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH2OH)4]Cl. The cation P(CH2OH)4+ is four-coordinate, as is typical for phosphonium salts. THPC has applications as a precursor to fire-retardant materials, as well as a microbiocide in commercial and industrial water systems.

<span class="mw-page-title-main">Methylphosphonic acid</span> Chemical compound

Methylphosphonic acid is an organophosphorus compound with the chemical formula CH3P(O)(OH)2. The phosphorus center is tetrahedral and is bonded to a methyl group, two OH groups and an oxygen. Methylphosphonic acid is a white, non-volatile solid that is poorly soluble in organic solvent but soluble in water and common alcohols.

References

  1. 1 2 "Vinylphosphonic acid". Sigma-Aldrich.
  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.
  3. 1 2 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.