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 [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.

Contents

Production

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.

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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<span class="mw-page-title-main">Copolymer</span> Polymer derived from more than one species of monomer

In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are sometimes called bipolymers. Those obtained from three and four monomers are called terpolymers and quaterpolymers, respectively. Copolymers can be characterized by a variety of techniques such as NMR spectroscopy and size-exclusion chromatography to determine the molecular size, weight, properties, and composition of the material.

<span class="mw-page-title-main">Nafion</span> Brand name for a chemical product

Nafion is a brand name for a sulfonated tetrafluoroethylene based fluoropolymer-copolymer synthesized in 1962 by Dr. Donald J. Connolly at the DuPont Experimental Station in Wilmington Delaware. Additional work on the polymer family was performed in the late 1960s by Dr. Walther Grot of DuPont. Nafion is a brand of the Chemours company. It is the first of a class of synthetic polymers with ionic properties that are called ionomers. Nafion's unique ionic properties are a result of incorporating perfluorovinyl ether groups terminated with sulfonate groups onto a tetrafluoroethylene (PTFE) backbone. Nafion has received a considerable amount of attention as a proton conductor for proton exchange membrane (PEM) fuel cells because of its excellent chemical and mechanical stability in the harsh conditions of this application.


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<span class="mw-page-title-main">Sodium polyacrylate</span> Anionic polyelectrolyte polymer

Sodium polyacrylate (ACR, ASAP, or PAAS), also known as waterlock, is a sodium salt of polyacrylic acid with the chemical formula [−CH2−CH(CO2Na)−]n and has broad applications in consumer products. This super-absorbent polymer (SAP) has the ability to absorb 100 to 1000 times its mass in water. Sodium polyacrylate is an anionic polyelectrolyte with negatively charged carboxylic groups in the main chain. It is a polymer made up of chains of acrylate compounds. It contains sodium, which gives it the ability to absorb large amounts of water. When dissolved in water, it forms a thick and transparent solution due to the ionic interactions of the molecules. Sodium polyacrylate has many favorable mechanical properties. Some of these advantages include good mechanical stability, high heat resistance, and strong hydration.

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<span class="mw-page-title-main">Acrylate polymer</span> Group of polymers prepared from acrylate monomers

An acrylate polymer is any of a group of polymers prepared from acrylate monomers. These plastics are noted for their transparency, resistance to breakage, and elasticity.

<span class="mw-page-title-main">Superabsorbent polymer</span> Polymers that absorb and retain extremely large amounts of liquid

A superabsorbent polymer (SAP) (also called slush powder) is a water-absorbing hydrophilic homopolymers or copolymers that can absorb and retain extremely large amounts of a liquid relative to its own mass.

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In polymer chemistry, gradient copolymers are copolymers in which the change in monomer composition is gradual from predominantly one species to predominantly the other, unlike with block copolymers, which have an abrupt change in composition, and random copolymers, which have no continuous change in composition . In the gradient copolymer, as a result of the gradual compositional change along the length of the polymer chain less intrachain and interchain repulsion are observed.

<span class="mw-page-title-main">Polyacrylic acid</span> Anionic polyelectrolyte polymer

Poly(acrylic acid) (PAA; trade name Carbomer) is a polymer with the formula (CH2-CHCO2H)n. It is a derivative of acrylic acid (CH2=CHCO2H). In addition to the homopolymers, a variety of copolymers and crosslinked polymers, and partially deprotonated derivatives thereof are known and of commercial value. In a water solution at neutral pH, PAA is an anionic polymer, i.e., many of the side chains of PAA lose their protons and acquire a negative charge. Partially or wholly deprotonated PAAs are polyelectrolytes, with the ability to absorb and retain water and swell to many times their original volume. These properties – acid-base and water-attracting – are the bases of many applications.

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

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<span class="mw-page-title-main">Bovine submaxillary mucin coatings</span> Surface treatment for biomaterials

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<span class="mw-page-title-main">Graft polymer</span> Polymer with a backbone of one composite and random branches of another composite

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<span class="mw-page-title-main">Hydroxyethyl acrylate</span> Organic chemical-monomer

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