Vinylphosphonic acid

Vinylphosphonic acid Basic information
Product Name:Vinylphosphonic acid
Synonyms:ethenephosphonicacid;ethenyl-phosphonicaci;ethenylphosphonicacid;ethylenephosphonicacid;vinyl-phosphonicaci;VINYLPHOSPHONIC ACID;VINYLPHOSPHONIC ACID 90 %, PURE;VINYLPHOSPHONIC ACID 65 %, TECHNICAL
CAS:1746-03-8
MF:C2H5O3P
MW:108.03
EINECS:217-123-2
Product Categories:Organic Building Blocks;Phosphonic/Phosphinic Acids;Monomers;Polymer Science;Vinyl Halides, Amines, Amides, and Other Vinyl Monomers;Phosphorus Compounds
Mol File:1746-03-8.mol
Vinylphosphonic acid Structure
Vinylphosphonic acid Chemical Properties
Melting point 41-45 °C(lit.)
Boiling point 97-98 °C(Press: 2 Torr)
density 1.389 g/mL at 25 °C(lit.)
vapor pressure 0Pa at 20℃
refractive index n20/D 1.473
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Soluble in water
pka2.11±0.10(Predicted)
form liquid
color colorless to pale-yellow
PH1.5 (50g/l, H2O, 30℃)
Water Solubility 100g/L at 20℃
BRN 1741622
LogP-1.69 at 20℃
CAS DataBase Reference1746-03-8(CAS DataBase Reference)
EPA Substance Registry SystemPhosphonic acid, ethenyl- (1746-03-8)
Safety Information
Hazard Codes C
Risk Statements 34-35-22
Safety Statements 26-36/37/39-45
RIDADR UN 3261 8/PG 2
WGK Germany 1
RTECS SZ7903500
HazardClass 8
PackingGroup III
HS Code 2931499090
MSDS Information
ProviderLanguage
SigmaAldrich English
Vinylphosphonic acid Usage And Synthesis
UsesVPA based homopolymers and copolymers find usage in corrosion treatment, fuel cells, dental cement, drug delivery, and bio-mimicry.
UsesVinylphosphonic acid (VPA) can be used as a monomer unit for the synthesis of poly(vinylphosphonic acid) via free radical polymerization. It is also used to develop copolymers of VPA with acrylonitrile, N-isopropylacrylamide, styrene, vinylpyrrolidone, and acrylic and methacrylic acid. These copolymers find potential application in hydrogels, drug delivery, biomimetic mineralization, and polymer electrolyte membranes in fuel cells.
It can also be used as an organic building block to prepare (E)-styryl phosphonic acid derivatives by reacting with various aryl halides via Pd-catalyzed Heck coupling reaction.
General DescriptionVinylphosphonic acid (VPA) is an organophosphorus compound that is used in the surface treatment of metal substrates. It can be used in the preparation of poly(VPA) by radical polymerization in the presence of initiator systems and chain transfer agents. PVPA tends to have an electrolytic nature, which is useful for a variety of energy based applications.
Flammability and ExplosibilityNotclassified
Purification MethodsThis fireproofing agent, and ingredient for making polymers, is obtained as a syrup on hydrolyzing vinylphosphonyl dichloride with cold H2O and solidifies on prolonged drying over P2O5/KOH. When distilled at 235-240o/0.0006mm, it gives the anhydride (d 1.304, n 1.5874) [Kabachnik & Medvedi Izvest Akad Nauk SSSR, Ser Khim 868 1953, Chem Abstr 54 10834 1960]. It is best kept as the sodium salt (m 350o) which precipitates when a solution of EtOH containing NaOEt (from 2g of Na) is added to vinylphosphonic acid (3.2g), and is recrystallised from EtOH (5.1g, quantitative). The p-anisidinium salt forms mauve prisms m 250o (from EtOH/Et2O). The dimethyl ester, M 136.1, d4 1.1405, nD 1.4330, has b 72.5o/10mm and 197-202o/760mm. [Kabachnik et al. J Gen Chem USSR (Engl Trans) 33 375 1963, Beilstein 4 IV 3568.]
Vinylphosphonic acid Preparation Products And Raw materials
Preparation ProductsDIETHYL VINYLPHOSPHONATE-->3-PHOSPHONOPROPIONIC ACID
BIS(CHLOROPROPYL)PROPENYL-2-PHOSPHONATE TETRAISOPROPYL VINYLIDENE DIPHOSPHONATE Triethoxyvinylsilane (4-AMINO-3-PHENYL-2-THIOXO-2,3-DIHYDRO-THIAZOL-5-YL)-PHOSPHONIC ACID DIETHYL ESTER DIETHYL CYCLOHEXYLAMINOVINYL PHOSPHATE VINYLPHOSPHONIC ACID O,O-DIMETHYL ESTER Ethyl 2-(Chlorosulfonyl)acetate Ascoric Acid N-Vinyl-2-pyrrolidone AURORA KA-1472 Stearic acid Vinyl ester resin VINYL PROPIONATE DIETHYL ALLYLPHOSPHONATE METHYLPHOSPHONIC ACID Vinyl resin Vinylphosphonic acid AURORA KA-1441

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