Names | |
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Preferred IUPAC name 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid | |
Other names 2-Acrylamido-2-methylpropane sulfonic acid; 2-Acrylamido-2-methylpropanesulfonic acid; 2-Acrylamido-2-methyl-1-propane sulfonic acid | |
Identifiers | |
3D model (JSmol) | |
Abbreviations | AMPS |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.035.683 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C7H13NO4S | |
Molar mass | 207.24 g·mol−1 |
Appearance | White crystalline powder or granular particles |
Density | 1.1 g/cm3 (15.6 °C) |
Melting point | 195 °C (383 °F; 468 K) |
Hazards | |
NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2-Acrylamido-2-methylpropane sulfonic acid (AMPS [1] ) was a Trademark name by The Lubrizol Corporation. It is a reactive, hydrophilic, sulfonic acid acrylic monomer used to alter the chemical properties of wide variety of anionic polymers. In the 1970s, the earliest patents using this monomer were filed for acrylic fiber manufacturing. Today, there are over several thousands patents and publications involving use of AMPS in many areas including water treatment, oil field, construction chemicals, hydrogels for medical applications, personal care products, emulsion coatings, adhesives, and rheology modifiers. Lubrizol discontinued the production of this monomer in 2017 due to copy-cat production from China and India destroying the profitability of this product.
AMPS is made by the Ritter reaction of acrylonitrile and isobutylene in the presence of sulfuric acid and water. [2] The recent patent literature [3] describes batch and continuous processes that produce AMPS in high purity (to 99.7%) and improved yield (up to 89%, based on isobutene) with the addition of liquid isobutene to an acrylonitrile / sulfuric acid / phosphoric acid mixture at 40°C.
Solvent | Solubility (gAMPS/100 g solvent) |
---|---|
Water | 150 |
Dimethylformamide | >100 |
N-Methyl-2-pyrrolidone | 80 |
Methanol | 8.7 |
Na-AMPS | 0.01N | 0.05N | 0.1N | 0.5N | 1.0N | 5.0N |
---|---|---|---|---|---|---|
K x 105 | 0.67 | 1.47 | 1.67 | 1.32 | 3.34 | 5.01 |
ν | 1.02 | 0.91 | 0.88 | 0.86 | 0.77 | 0.72 |
M1 | r1 | r2 | Remark |
---|---|---|---|
Acrylonitrile | 1.2 | 0.7 | DMF |
Acrylic acid | 0.74 | 0.19 | Water, pH=7.0 |
Acrylic acid | 1.58 | 0.11 | Water, pH=2~4 |
Itaconic acid | 0.46 | 0.04 | DMF, 70 °C, Benzoyl Peroxide |
Acrylamide | 0.98 | 0.49 † | Water, K2S2O8 |
Styrene | 1.13 | 0.31 | DMF, 60 °C, AIBN |
Vinyl Acetate | 0.05 | 11.60 † | Methanol, 60 °C, |
N-Vinylpyrrolidone | 0.13 | 0.66 † | 60 °C, AIBN |
2-hydroxyethyl methacrylate | 0.86 | 0.90 | Water, 60 °C, AIBN |
2-Hydroxypropyl methacrylate | 6.30 | 0.04 | Water, 80 °C, (NH4)2S2O8 |
N,N-Dimethylacrylamide | 1.26 | 0.68 † | Water, 30 °C, K2S2O8 |
N-Vinylformamide | 0.32 | 0.39 † | VA-044 |
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