15214-89-8

Basic information

• Product Name: 2-Acrylamide-2-methylpropanesulfonic acid
• Synonyms: 1-Propanesulfonicacid,2-methyl-2-[(1-oxo-2-propenyl)amino]-;2-Acrylamido-2-methyl-1-propane;2-acrylamido-2-methylpropanesulfonate;2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonicaci;TBAS;ACRYLAMIDO BUFFER;AMPS;AMPS MONOMER
• CAS NO: 15214-89-8
• Molecular Formula: C₇H₁₃NO₄S
• Molecular Weight: 207.25
• EINECS: 239-268-0
• Product Categories: Industrial/Fine Chemicals;monomer;Organic Chemicals;Acrylamide and Methacrylamide;Acrylic Monomers;Monomers
• Mol File: 15214-89-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 195-200 °C (dec.)(lit.)
• Boiling Point: 412oC
• Flash Point: 160 °C
• Appearance: White/solution
• Density: 1.45
• Vapor Pressure: <0.0000004 hPa (25 °C)
• Refractive Index: 1.6370 (estimate)
• Storage Temp.: 2-8°C
• Solubility: >500g/l soluble
• PKA: 1.67±0.50(Predicted)
• Water Solubility: 1500 g/L (20 ºC)
• Sensitive: Hygroscopic
• Stability: Light Sensitive
• BRN: 1946464
• CAS DataBase Reference: 2-Acrylamide-2-methylpropanesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acrylamide-2-methylpropanesulfonic acid(15214-89-8)
• EPA Substance Registry System: 2-Acrylamide-2-methylpropanesulfonic acid(15214-89-8)

Safety Data

• Hazard Codes: C,Xn
• Statements: 34-21/22-41-37-20/22
• Safety Statements: 26-36/37/39-45-22
• RIDADR: UN 2585 8/PG 3
• WGK Germany: 1
• RTECS: TZ6658000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 15214-89-8(Hazardous Substances Data)

Usage

Chemical Properties

2-Acrylamide-2-methylpropanesulfonic acid is a white crystals. The melting point is 195°C (decomposition). Soluble in water, the solution is acidic. Soluble in dimethylformamide, partially soluble in methanol, ethanol, insoluble in acetone. Slightly sour.

Uses

2-Acrylamide-2-methylpropanesulfonic 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.

Preparation

2-Acrylamido-2-methylpropanesulfonic acid(AMPS) 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. One-step method is more economical. Raw material consumption quota: isobutylene 300kg/t, acrylonitrile 290kg/t, oleum 560kg/t.

Application

2-Acrylamide-2-methylpropanesulfonic 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.

InChI: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)/p-1

Synthetic route

acrylonitrile (107-13-1) + isobutene (115-11-7) → 2-acrylamido-2-methylpropanesulfonic acid (15214-89-8)

Conditions	Yield
With sulfur trioxide at 8 - 35℃; Temperature;	92.2%
Stage #1: acrylonitrile With sulfuric acid In water at -10 - -7℃; for 2h; Stage #2: isobutene With acetic acid at 10 - 70℃; for 1.5h; Temperature;	92.09%
With methanesulfonic acid; sulfuric acid at 0 - 45℃; under 760.051 Torr; for 1h; Reagent/catalyst; Temperature;	82.3%

acrylonitrile (107-13-1) + isobutene (115-11-7) → N-tert-Butylacrylamide (107-58-4) + 2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenamide (79-06-1)

Conditions	Yield
With sulfuric acid at 20℃; for 2h;	A n/a B 87% C n/a

1-vinylimidazole (1072-63-5) + 2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) → C7H13NO4S*C5H6N2 (942205-52-9)

Conditions	Yield
In methanol at 20℃; for 4h;	100%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → 2-acrylamido-2-methylpropane sulfonic acid tetrabutylammonium salt (181208-67-3)

Conditions	Yield
In methanol at 200℃;	100%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenamide (79-06-1) → polymer, Mw 61 kDa, sulfur content 6.97%, 2-acrylamido-2-methylpropanesulfonic acid units content 22.0 mol%; monomer(s): acrylamide; 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 50℃; for 24h;	99.8%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenamide (79-06-1) → polymer, Mw 36 kDa, sulfur content 6.16%, 2-acrylamido-2-methylpropanesulfonic acid units content 18.5 mol%; monomer(s): acrylamide; 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 50℃; for 24h;	99.8%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenamide (79-06-1) → polymer, Mw 19 kDa, sulfur content 6.18%, 2-acrylamido-2-methylpropanesulfonic acid units content 19.1 mol%; monomer(s): acrylamide; 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In isopropyl alcohol at 50℃; for 24h;	99.8%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenamide (79-06-1) → polymer, sulfur content 9.42%, 2-acrylamido-2-methylpropanesulfonic acid units content 37.6 mol%; monomer(s): acrylamide; 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 50℃; for 24h;	99.7%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenamide (79-06-1) → polymer, Mw 16 kDa, sulfur content 5.86%, 2-acrylamido-2-methylpropanesulfonic acid units content 17.3 mol%; monomer(s): acrylamide; 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 50℃; for 24h;	99.6%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenamide (79-06-1) → polymer, Mw 28 kDa, sulfur content 7.16%, 2-acrylamido-2-methylpropanesulfonic acid units content 22.8 mol%; monomer(s): acrylamide; 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 50℃; for 24h;	99.2%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + Tris(3,6-dioxaheptyl)amine (70384-51-9) → tris-[2-(2-methoxy-ethoxy)-ethyl]-amine; compound with 2-acryloylamino-2-methyl-propane-1-sulfonic acid

Conditions	Yield
at 25℃; for 8h;	99%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenamide (79-06-1) → polymer, Mw 23 kDa, sulfur content 6.07%, 2-acrylamido-2-methylpropanesulfonic acid units content 18.2 mol%; monomer(s): acrylamide; 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In isopropyl alcohol at 50℃; for 24h;	98.8%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + trimethylamine (75-50-3) → 2-Methyl-2-(3-trimethylammoniopropionamido)propanesulfonate

Conditions	Yield
With hydroquinone In water at 25℃; for 24h;	95%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenamide (79-06-1) → polymer, sulfur content 9.13%, 2-acrylamido-2-methylpropanesulfonic acid units content 33.1 mol%; monomer(s): acrylamide; 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 50℃; for 24h;	95%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenamide (79-06-1) → polymer, Mw 14 kDa, sulfur content 7.21%, 2-acrylamido-2-methylpropanesulfonic acid units content 23.0 mol%; monomer(s): acrylamide; 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 50℃; for 24h;	94.8%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) → poly(2-acrylamido-2-methylpropanesulfonic acid) sodium salt; monomer(s): 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With sodium hydroxide In water at 50℃; for 5h; Kinetics; Activation energy; Further Variations:; Temperatures; Reagents;	85%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-(1H,1H,2H,2H-perfluorooctylthio)-1-methylimidazole → 2-(1H,1H,2H,2H-perfluorooctylthio)-1-methylimidazolium 2-acrylamido-2-methylpropanesulfonate

Conditions	Yield
In methanol at 20℃; for 0.25h;	84%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) → 2-[3-(1-Azonia-4-azabicyclo[2.2.2]oct-1-yl)propionamido]-2-methylpropanesulfonate

Conditions	Yield
With hydroquinone In water at 20℃; for 24h;	82%
In water at 20℃; for 24h; Addition;	81.7%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2,7-dibromo-9H-fluorene (16433-88-8) → 9,9-bis(3-propylamide-2-methylpropyl sulfonic acid)fluorene

Conditions	Yield
Stage #1: 2,7-dibromo-9H-fluorene With tetrabutylammomium bromide; potassium hydroxide In water; dimethyl sulfoxide at 4℃; for 1h; Stage #2: 2-acrylamido-2-methylpropanesulfonic acid In water; dimethyl sulfoxide for 10h; Michael Addition;	79%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 3-(diphenylphosphino)propionic acid (2848-01-3) → 2-[3-(2-carboxyethyl)diphenylphosphonio]propanamido-2-methylpropane-1-sulfonate

Conditions	Yield
In acetonitrile at 20℃; for 48h;	79%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + benzyltri(n-butyl)ammonium chloride (23616-79-7) → benzyltributylammonium 2-acrylamido-2-methyl-1-propanesulfonate (1161027-41-3)

Conditions	Yield
In water at 20℃; for 0.0833333h;	73%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → N,N-dimethyl-N-(3-methacrylamidopropyl)-N-[N'-(1,1-dimethyl-2-sulfonatoethyl)propionamido]betaine

Conditions	Yield
With hydroquinone In water at 20℃; for 72h; Addition;	71%
With hydroquinone In water at 70℃; Kinetics; Concentration;

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + tetraethylammonium hydroxide (77-98-5) + diphenylphosphane (829-85-6) → 2-(3-Diphenylphosphanyl-propionylamino)-2-methyl-propane-1-sulfonatetetraethyl-ammonium;

Conditions	Yield
With ditertbutylphenol In water; acetonitrile for 4h; Ambient temperature;	70%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + (11-Methacryloyl-amino)undecansaeure (59178-93-7) → 11-methacrylamidoundecanoic acid/2-acrylamido-2-methylpropanesulfonic acid copolymer

Conditions	Yield
With sodium hydroxide In methanol at 60℃; for 21h; Product distribution / selectivity;	69.2%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 12-(methacrylolamino)dodecanoic acid (62839-65-0) → 12-methacrylamidododecanoic acid/2-acrylamido-2-methylpropanesulfonic acid copolymer

Conditions	Yield
With sodium hydroxide; 2,2'-azobis(isobutyronitrile) In methanol at 60℃; for 21h; Product distribution / selectivity;	67.5%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) → polymer, Mw 40 kDa, sulfur content 15.8%; monomer(s): 2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 50℃; for 24h;	59.7%

1,4,8,11-Tetraazacyclotetradecane (295-37-4) + 2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) → 2-<3-(1,4,8,11-Tetraazacyclotetradecan-1-yl)propionylamino>-2-methylpropane-1-sulfonic acid

Conditions	Yield
With 2,4-di-tert-Butylphenol In chloroform for 336h; Ambient temperature;	59%

sodium 11-methacrylamidoundecanoate + 2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) → sodium 11-methacrylamidoundecanoic acid/2-acrylamido-2-methylpropanesulfonic acid

Conditions	Yield
With sodium hydroxide; 2,2'-azobis(isobutyronitrile) In methanol; water at 60℃; for 12.5h;	53.71%

2-(acrylamidomethyl)-18-crown-6 + 2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) → poly{(2-acrylamido-2-methyl-1-propanesulfonic acid)-co-[2-(acrylamidomethyl)-18-crown-6]}, Mn 47000 g/mol, PDI 1.68; monomer(s): 2-acrylamido-2-methyl-1-propanesulfonic acid, 80 mol percent; 2-(acrylamidomethyl)-18-crown-6, 20 mol percent

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In tert-butyl alcohol for 19h;	47%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) → poly(2-acrylamido-2-methylpropanesulfonic acid), radical polymerization

Conditions	Yield
With sodium disulfite; potassium peroxomonosulphate; sorbitan monostearate In hexane; water at 60℃; for 1h; pH=9; Kinetics; Product distribution; Polymerization;	41%

Upstream product

• 107-13-1 acrylonitrile 
• 115-11-7 isobutene 

Downstream Products

• 58374-69-9 ammonium acryloyldimethyltaurate 
• 107-58-4 N-tert-Butylacrylamide 
• 5165-97-9 sodium 2-acrylamido-2-methylpropane-1-sulfonate 
• 1161027-41-3 benzyltributylammonium 2-acrylamido-2-methyl-1-propanesulfonate 

Relevant articles and documents

NEW METHOD FOR PRODUCING 2-ACRYLAMIDO-2-METHYLPROPANE SULPHONIC ACID

The present invention relates to a production process for 2-acrylamido-2-methylpropane sulfonic acid including at least the following successive steps: 1) mixing of acrylonitrile with at least one compound contributing SO3 at a temperature included between ?80 and 30° C.;2) placing in contact and mixing isobutylene and the sulfonating mixture with a molar ratio of SO3 to isobutylene included between 0.2:1 and 2:1 and a molar ratio of acrylonitrile to isobutylene included between 3:1 and 60:1 at a temperature included between ?40 and 100° C.;3) solid/liquid separation of the reaction mixture and isolation of the solid particles in the form of a composition 1;4) mixing composition 1 at the end of step 3) with an aqueous solution A included at a temperature comprised between ?20 and 70° C. in order to obtain a suspension 1 of 2-acrylamido-2-methylpropane sulfonic acid crystals;5) solid/liquid separation of the suspension 1 and isolation of the crystals in form of composition 2.

A 2 - acrylamide - 2 - methyl (alkanes) sulfonic acid

The invention relates to a preparation method of 2-acrylamido-2-methylpropane sulfonic acid, and belongs to the field of organic synthesis and preparation. The preparation method comprises the steps of (1) adding acrylonitrile in a liquid-preparing kettle, cooling, and adding fuming sulfuric acid to obtain a mixed solution of acrylonitrile and sulfuric acid; (2) transferring partial mixed solution into a feed tank with a constant temperature for use, adding the residual mixed solution into a reaction kettle, adding an organic acid, heating, introducing isobutene, adding the standby mixed solution of acrylonitrile and sulfuric acid and controlling a temperature, a feed time and speed; (3) when isobutene is completely introduced, stirring while keeping the temperature, cooling, centrifuging or filtering to separate coarse crystals of a generated product and pumping a filtrate into a storage tank; (4) mixing the coarse crystals of the product with acrylonitrile under stirring, separating by centrifugation, drying in vacuum to obtain a product of 2-acrylamido-2-methylpropane sulfonic acid and pumping the filtrate into the storage tank; and (5) merging the filtrates, contacting the mixed filtrate with quicklime, and distilling to recycle acrylonitrile. The product provided by the invention has high purity and high polymerization activity and is liable to obtain a polymer with relatively high molecular weight.

Process for reducing sulfate ions in synthesis process of 2-acrylamido-2-methylpropanesulfonic acid

The invention discloses a process for reducing sulfate ions in the synthesis process of 2-acrylamido-2-methylpropanesulfonic acid. The process comprises the following steps: (1) firstly, adding certain parts of acrylonitrile and a dehydrant into a reaction kettle, and supplying cooling water to cool to minus 30 DEG C to 0 DEG C; (2) introducing gasified isobutene into the reaction kettle at minus 30 DEG C to 0 DEG C, introducing a certain amount of the component, and continuously introducing isobutene and dropping fuming sulfuric acid at the same time; (3) after the fuming sulfuric acid is completely added, continuously introducing a certain amount of an isobutene gas; (4) after the material is completely added, performing heat-preservation reaction at 10-40 DEG C; and (5) performing cooling crystallization on a generated paste product, and performing separation drying, thereby obtaining a 2-acrylamido-2-methylpropanesulfonic acid synthesized product. The synthesized product disclosed by the invention is high in purity, low in cost, convenient in industrial production and relatively low in sulfate radical residue without refining.