2-Acrylamido-2-methylpropane sulfonic acid

Last updated
2-Acrylamido-2-methylpropane sulfonic acid
2-Acrylamido-2-methylpropane sulfonic acid.png
AMPS-3D-spacefill.png
Names
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)
AbbreviationsAMPS
ChEMBL
ChemSpider
ECHA InfoCard 100.035.683 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 925-482-8
PubChem CID
UNII
  • InChI=1S/C7H13NO4S/c1-4-6(9)8-7(2,3)5-13(10,11)12/h4H,1,5H2,2-3H3,(H,8,9)(H,10,11,12) Yes check.svgY
    Key: XHZPRMZZQOIPDS-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H13NO4S/c1-4-6(9)8-7(2,3)5-13(10,11)12/h4H,1,5H2,2-3H3,(H,8,9)(H,10,11,12)
    Key: XHZPRMZZQOIPDS-UHFFFAOYAO
  • O=C(NC(CS(=O)(=O)O)(C)C)C=C
Properties
C7H13NO4S
Molar mass 207.24 g·mol−1
AppearanceWhite 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)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
0
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Acrylamido-2-methylpropane sulfonic acid (AMPS) 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.

Contents

Production

AMPS is made by the Ritter reaction of acrylonitrile and isobutylene in the presence of sulfuric acid and water. [1] The recent patent literature [2] 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.

Properties

SolventSolubility (gAMPS/100 g solvent)
Water150
Dimethylformamide >100
N-Methyl-2-pyrrolidone 80
Methanol 8.7
Na-AMPS0.01N0.05N0.1N0.5N1.0N5.0N
K x 1050.671.471.671.323.345.01
ν1.020.910.880.860.770.72
M1r1r2Remark
Acrylonitrile 1.20.7 DMF
Acrylic acid 0.740.19Water, pH=7.0
Acrylic acid 1.580.11Water, pH=2~4
Itaconic acid 0.460.04 DMF, 70 °C, Benzoyl Peroxide
Acrylamide 0.980.49 Water, K2S2O8
Styrene 1.130.31 DMF, 60 °C, AIBN
Vinyl Acetate 0.0511.60 Methanol, 60 °C,
N-Vinylpyrrolidone 0.130.66 60 °C, AIBN
2-hydroxyethyl methacrylate 0.860.90Water, 60 °C, AIBN
2-Hydroxypropyl methacrylate 6.300.04Water, 80 °C, (NH4)2S2O8
N,N-Dimethylacrylamide 1.260.68 Water, 30 °C, K2S2O8
N-Vinylformamide 0.320.39 VA-044

Applications

See also

Related Research Articles

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