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2-METHYL-2-(PROP-2-ENAMIDO)PROPANE-1-SULFONIC ACID

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid belongs to the class of organic compounds known as organosulfonic acids.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid copolymer is a moderately basic compound (based on its pKa).

CAS Number: 15214-89-8
Molecular Formula: C7H13NO4S
Molecular Weight: 207.25
EINECS Number: 239-268-0

Synonyms: 15214-89-8, 2-Acrylamido-2-methyl-1-propanesulfonic acid, 2-Acrylamido-2-methylpropanesulfonic acid, 2-Acrylamide-2-methylpropanesulfonic acid, 27119-07-9, 2-acrylamido-2-methylpropane-1-sulfonic acid, 1-Propanesulfonic acid, 2-methyl-2-[(1-oxo-2-propenyl)amino]-, 2-Acrylamido-2-methylpropanesulfonate, 2-Acrylamido-2-methylpropanesulphonic acid, AtBS, acryloyldimethyltaurine, DTXSID5027770, LUBRIZOL AMPS, 2-methyl-2-(prop-2-enoylamino)propane-1-sulfonic acid, TBAS-Q, 1-Propanesulfonic acid, 2-acrylamido-2-methyl-, 490HQE5KI5, DTXCID207770, tert-butylacrylamidosulfonic acid, 2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid, acrylamide tert-butylsulfonic acid, acrylamidomethylpropanesulfonic acid, 2-acrylamido-2-methylpropylsulfonic acid, 1-Propanesulfonic acid, 2-methyl-2-((1-oxo-2-propenyl)amino)-, 2-(acryloylamino)-2-methylpropane-1-sulfonic acid, 2-ACRYLAMIDO-2,2-DIMETHYLETHANESULFONIC ACID, 1-Propanesulfonic acid, 2-methyl-2-((1-oxo-2-propen-1-yl)amino)-, CAS-15214-89-8, EINECS 239-268-0, 2-ACRYLAMIDO-2-METHYLPROPANE SULFONIC ACID, UNII-490HQE5KI5, EC 239-268-0, 2-Acrylamido-2-methylpropanesulfonic acid (AMPS), SCHEMBL19490, 2-Acryloylamido-2-methylpropanesulfonic acid monomer, CHEMBL1907040, CHEBI:166476, Tox21_201781, Tox21_303523, MFCD00007522, AKOS015898709, CS-W015266, 5165-97-9 (mono-hydrochloride salt), NCGC00163969-01, NCGC00163969-02, NCGC00257492-01, NCGC00259330-01, 2-acrylamido-2-methyl propanesulfonic acid, 2-acrylamido-2-methyl propyl sulfonic acid, 2-acrylamido-2-methyl-propane sulfonic acid, 2-Acrylamido-2-methyl-1-propanesulfonicacid, 2-Acryloylamido-2-methylpropanesulfonic acid, A0926, NS00005061, 2-ACRYLAMIDO-2-METHYLPROPIONESULFONATE, E76045, Q209301, 2-Acrylamido-2-methyl-1-propanesulfonic acid, 8CI, 2-Acrylamido-2-methyl-1-propanesulfonic acid, 99%, 2-methyl-2-(prop-2-enamido)propane-1-sulfonic acid, J-200043, 2-(Acryloylamino)-2-methyl-1-propanesulfonic acid #, 2-methyl-2-(prop-2-enoylamino)propane-1-sulonic acid, 82989-71-7, 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

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is a white crystals.
The melting point is 195°C (decomposition).
Soluble in water, the solution is acidic.

Soluble in 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid, partially soluble in methanol, ethanol, insoluble in acetone.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is an organosulfonic acid.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid 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 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid 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.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is made by the Ritter reaction of acrylonitrile and isobutylene in the presence of sulfuric acid and water.
The recent patent literature describes batch and continuous processes that produce 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid 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.

The geminal dimethyl group and the sulfomethyl group combine to sterically hinder the amide functionality and provide both hydrolytic and thermal stabilities to 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid-containing polymers.
The sulfonate group gives the monomer a high degree of hydrophilicity and anionic character at wide range of pH.
In addition, 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is absorbing water readily and also imparts enhanced water absorption and transport characteristics to polymers.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is very soluble in water and dimethylformamide (DMF) and also shows limited solubility in most polar organic solvents.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is a chemical compound with the molecular formula C6H11NO4S.
It is also known as MAPS (Methacrylamidopropanesulfonic acid).

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is characterized by the presence of a sulfonic acid group (-SO3H) and an amide group (-CONHCH=CH2) attached to a propane chain.
Sulfonic acid in 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is a very strong ionic group and ionizes completely in aqueous solutions.
In applications where the precipitation of mineral salts is undesirable, the incorporation of a polymer containing even a small quantity of 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid can significantly inhibit the precipitation of divalent cations.

The result is a significant reduction in the precipitation of a wide variety of mineral salts, including calcium, magnesium, iron, aluminium, zinc, barium and chromium.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid has good complexion, adsorption, biological activity, surface activity, hydrolysis stability and thermal stability.
It can be used in oil chemical, water treatment, synthetic fiber, printing and dyeing, plastics, water absorbing coatings, paper, bio-medical, magnetic materials and cosmetics industries.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid has good complexion, adsorption, biological activity, surface activity, hydrolysis stability and thermal stability.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid can be used in oil chemical, water treatment, synthetic fiber, printing and dyeing, plastics, water absorbing coatings, paper, bio-medical, magnetic materials and cosmetics industries.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid, belongs to the class of organic compounds known as organosulfonic acids.
Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
Based on a literature review very few articles have been published on 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is an organosulfonic acid.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is a reactive, hydrophilic, sulfonic acid acrylic monomer
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is 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.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is used in many areas including water treatment, oil field, construction chemicals, hydrogels
for medical applications, personal care products, emulsion coatings, adhesives, and rheology modifiers.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is primarily used as a monomer in the synthesis of polymers and copolymers due to its ability to provide sulfonic acid functionality, which can impart specific properties such as ion exchange capabilities, water solubility, and chemical stability.
It is commonly employed in industries related to water treatment, membranes, coatings, adhesives, and various specialty chemicals where these properties are beneficial.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid consists of a propane backbone with an amide group (-CONH-) and a sulfonic acid group (-SO3H) attached to it.

The "2-methyl" prefix indicates a methyl group (-CH3) attached to the carbon adjacent to the amide group.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid can be synthesized through various methods involving the reaction of suitable starting materials.
One common approach involves the reaction of 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid, followed by sulfonation to introduce the sulfonic acid group.

Melting point: 195 °C (dec.) (lit.)
Density: 1.45
vapor pressure: <0.0000004 hPa (25 °C)
refractive index: 1.6370 (estimate)
Flash point: 160 °C
storage temp.: Store below +30°C.
solubility: >500g/l soluble
pka: 1.67±0.50(Predicted)
form: solution
color: White
Water Solubility: 1500 g/L (20 ºC)
Sensitive: Hygroscopic
BRN: 1946464
Stability: Light Sensitive
InChIKey: HNKOEEKIRDEWRG-UHFFFAOYSA-N
LogP: -3.7 at 20℃ and pH1-7
Surface tension: 70.5mN/m at 1g/L and 20℃
Dissociation constant: 2.4 at 20℃

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid can be synthesized by one step and two steps.
The one-step method is to react the raw materials acrylonitrile, isobutylene and oleum together.
The two-step method is to sulfonate isobutylene in the presence of a reaction solvent to obtain a sulfonated intermediate, and then react with acrylonitrile in the presence of sulfuric acid.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is an important monomer.
Its copolymers or homopolymers with different molecular weight can be widely used in textile, oil drilling, water treatment, papermaking, dying, coating, cosmetics, electronics, etc. because of its unique formular structure—containing sulfonic acid group and unsaturated radical, thus showing excellent properties in many aspects.
A number of enhanced performance characteristics are imparted to acrylic, modified-acrylic, polypropylene and polyvinylidene fluoride fibers: dye receptivity, moisture absorbency, and static resistance.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is sulfonic acid group gives the monomers ionic character over a wide range of pH.
Anionic charges from AMPS fixed on polymer particles enhance the chemical and shear stabilities of polymer emulsion and also reduce the amount of surfactants leaching out of paint film.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid improves the thermal and mechanical properties of adhesives, and increases the adhesive strength of pressure-sensitive adhesive formulations.

Enhances the washing performance of surfactants by binding multivalent cations and reducing dirt attachment.
Strong polar and hydrophilic properties introduced to a high molecular weight 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid homopolymer are exploited as a very efficient lubricant characteristic for skin care.
High water-absorbing and swelling capacity when 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is introduced to a hydrogel are keys to medical applications.

Hydrogel with 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid showed uniform conductivity, low electrical impedance, cohesive strength, appropriate skin adhesion, and biocompatible and capable of repeated use and have been used to electrocardiograph (ECG) electrodes, defibrillation electrode, electrosurgical grounding pads, and iontophoretic drug delivery electrodes.
In addition, polymers derived from 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid are used as the absorbing hydrogel and the tackifier component of wound dressings.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is used due to its high water absorption and retention capability as a monomer in superabsorbents e. g. for baby diapers.
Oil field applications: Polymers in oil field applications have to stand hostile environments and require thermal and hydrolytic stability and the resistance to hard water containing metal ions.
For example, in drilling operations where conditions of high salinity, high temperature and high pressure are present, 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid copolymers can inhibit fluid loss and be used in oil field environments as scale inhibitors, friction reducers and water-control polymers, and in polymer flooding applications.

The cation stability of the 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid-containing polymers are very useful for water treatment processes.
Such polymers with low molecular weights cannot only inhibit calcium, magnesium, and silica scale in cooling towers and boilers, but also help corrosion control by dispersing iron oxide.
When high molecular weight polymers are used, they can be used to precipitate solids in the treatment of industrial effluent stream.

Increases in dissolved and nanoparticulate polymer formulations bioavailability of pesticides in aqueous-organic formulations.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid increases water flow, retention and fouling resistance of asymmetric ultrafiltration and microfiltration membranes and is being studied as an anionic component in polymer fuel cell membranes.
Superplasticizers with AMPS are used to reduce water in concrete formulations.

Benefits of these additives include improved strength, improved workability, improved durability of cement mixtures.
Redispersible polymer powder, when 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is introduced, in cement mixtures control air pore content and prevent agglomeration of powders during the spray-drying process from the powder manufacturing and storage.
Coating formulations with 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid-containing polymers prevent calcium ions from being formed as lime on concrete surface and improve the appearance and durability of coating.

Increases in dissolved and nanoparticulate polymer formulations bioavailability of pesticides in aqueous-organic formulations.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid increases water flow, retention and fouling resistance of asymmetric ultrafiltration and microfiltration membranes and is being studied as an anionic component in polymer fuel cell membranes.
Superplasticizers with Acrylamido-2-Methylpropane Sulfonic Acid are used to reduce water in concrete formulations.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is white powder.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid has good complexion, adsorption
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid has biological activity, surface activity, hydrolysis stability and thermal stability.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid can be used in oil chemical, water treatment, synthetic fiber, printing and dyeing, plastics, water absorbing coatings, paper, bio-medical, magnetic materials and cosmetics industries.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is an important monomer.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid's copolymers or homopolymers with different molecular weight can be widely used in textile, oil drilling, water treatment, papermaking, dying, coating, cosmetics, electronics, etc. because of its unique formular structure— containing sulfonic acid group and unsaturated radical, thus showing excellent properties in many aspects.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid has good complexion, adsorption, biological activity, surface activity, hydrolysis stability and thermal stability.

Uses Of 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid:
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid has good complexion, adsorption, biological activity, surface activity, hydrolysis stability and thermal stability.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid can be used in oil chemical, water treatment, synthetic fiber, printing and dyeing, plastics, water absorbing coatings, paper, bio-medical, magnetic materials and cosmetics industries.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is an important monomer.
Its copolymers or homopolymers with different molecular weight can be widely used in textile, oil drilling, water treatment, papermaking, dying, coating, cosmetics, electronics, etc. because of its unique formular structure ontaining sulfonic acid group and unsaturated radical, thus showing excellent properties in many aspects.
Polymers derived from 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid can exchange ions, making them useful in ion exchange resins used for water softening and purification processes.

The presence of the sulfonic acid group enhances water solubility, which is advantageous in applications requiring water-soluble polymers.
Due to its ion exchange capabilities and water solubility, MAPS is extensively used in water treatment applications:
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is employed in the production of ion exchange resins that can selectively remove ions from water, improving water quality by reducing hardness and removing contaminants.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid-based polymers are used in membrane technologies for applications such as desalination and wastewater treatment.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is incorporated into formulations for coatings and adhesives:
Its chemical stability under various conditions makes MAPS suitable for use in coatings where durability and chemical resistance are required.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid can enhance the adhesive properties of formulations, improving bonding strength in adhesive applications.
In the field of energy storage and electrochemical devices, 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is utilized in the formulation of electrolytes:
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid contributes to the ion conductivity of electrolyte solutions, crucial for the performance of batteries and supercapacitors.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid has potential applications in biomedical research and pharmaceuticals:
Its biocompatibility and ability to interact with biological molecules make 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid suitable for use in drug delivery systems.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid-based polymers can be developed into biomaterials for various medical applications, including tissue engineering and controlled release systems.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid may also find uses in other industrial applications where its properties, such as solubility, stability, and ion exchange capabilities, are beneficial.
These can include specialty chemicals, catalysis, and materials science.
Its ion exchange properties make MAPS effective in formulations designed to remove scales and deposits from surfaces, equipment, and industrial systems.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is employed in the textile industry for:
Its water-soluble nature and chemical stability make 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid useful in dyeing processes and textile finishing treatments.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid-based polymers can be used as antistatic agents in textiles to reduce static electricity buildup.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is incorporated into formulations to prevent the formation of scales in drilling fluids and production equipment.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid-based polymers can be used in enhanced oil recovery processes to modify the rheological properties of fluids.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is used as a retention aid in papermaking processes to improve the retention of fillers and fibers, thereby enhancing paper strength and quality.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid-based polymers can act as charge control agents in paper coatings to improve printability and paper surface properties.
Its ability to modify viscosity makes MAPS suitable as a thickening agent in lotions, creams, and other personal care formulations.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid can stabilize emulsions and suspensions in cosmetic products, improving their shelf life and consistency.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid may be included in the formulation of photographic developers to enhance their performance in image processing.
In controlled and approved applications, 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid could potentially serve as a food additive, depending on regional regulations and safety assessments.

Safety Profile Of 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid:
As with handling any chemical substance, proper precautions should be taken during its synthesis, handling, and storage.
It is important to consult safety data sheets (SDS) and follow recommended practices to minimize exposure and risks associated with handling sulfonic acids and related chemicals.
2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid may cause irritation to the eyes upon direct contact.

In case of contact, immediate rinsing with plenty of water is recommended.
Prolonged or repeated contact with 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid may lead to skin irritation.
It is advisable to wear appropriate protective gloves and clothing when handling MAPS to minimize skin exposure.

There is a potential for respiratory sensitization upon inhalation of 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid dust or vapors.
Adequate ventilation should be provided in areas where 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is handled to minimize inhalation exposure.

2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid is generally considered to be biodegradable and unlikely to persist in the environment.
However, 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid should be handled and disposed of in accordance with local regulations to prevent environmental contamination.