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Methacrylic Acid, Methlacrylic Acid, MAA, 79-41-4 

Methacrylic Acid, Methlacrylic Acid, MAA, 79-41-4

METHACRYLIC ACID (MAA)

Methacrylic Acid / Methylacrylic Acid / 2-Methylacrylic Acid / α-Methylacrylic Acid / 2-Methylpropenoic Acid
CAS Number: 79-41-4
EC Number: 201-204-4

1. IDENTIFICATION INFORMATION

Property Information
Chemical Name Methacrylic Acid
Other Names Methylacrylic Acid, 2-Methylacrylic Acid, α-Methylacrylic Acid, 2-Methylpropenoic Acid, 2-Methyl-2-propenoic acid
Chemical Formula C₄H₆O₂
Molecular Weight 86.09 g/mol
CAS Number 79-41-4
EC Number (EINECS) 201-204-4
Appearance Colorless clear liquid
Odor Repulsive, acrid
Physical State Liquid (at room temperature)
Stabilizer MEHQ (Hydroquinone methyl ether, ca. 250 ppm) or hydroquinone

2. PHYSICAL PROPERTIES

Property Value
Physical State (20°C) Liquid
Appearance Colorless clear liquid
Odor Repulsive, acrid, sharp
Chemical Formula C₄H₆O₂
Molecular Weight 86.09 g/mol
Density (25°C) 1.015 g/mL
Melting Point 12-16°C (14°C typical)
Boiling Point 163°C (lit.)
Boiling Point Range 159-163°C
Flash Point 77°C (170°F) (closed cup)
Autoignition Temperature 752°F (400°C)
Vapor Pressure (20°C) 1 mmHg
Vapor Density (air=1) >3
Water Solubility (20°C) 9.7 g/100 mL (moderately soluble)
Solubility in Organic Solvents Soluble in ethanol and most organic solvents
Viscosity (20°C) 1.3 mPa·s
Refractive Index (n20/D) 1.431
pKa (25°C) 4.66
pH (100 g/L aqueous solution, 20°C) 2.0 - 2.2
Explosive Limit 1.6 - 8.7% (V)
LogP (22°C) 0.93

3. CHEMICAL PROPERTIES

Property Information
Chemical Formula C₄H₆O₂
Molecular Weight 86.09 g/mol
Chemical Class Unsaturated carboxylic acid
Functional Groups Carboxylic acid (-COOH) and vinyl double bond (C=C)
Structure CH₂=C(CH₃)-COOH
Stability May polymerize readily in the absence of a stabilizer
Stabilizer MEHQ (250 ppm) or hydroquinone
Polymerization Undergoes free radical polymerization
Esterification Forms methacrylate esters (e.g., methyl methacrylate)
Reaction with Alcohols Forms esters (methacrylates)
Reaction with Bases Forms methacrylate salts
Reaction with Water Moderately soluble; acidic solution
Incompatible Materials Strong oxidizing agents, strong bases, amines, peroxides, polymerization initiators

Polymerization Reaction:

n CH₂=C(CH₃)-COOH → [CH₂-C(CH₃)(COOH)]n (Polymethacrylic acid)

Esterification Reaction (Methyl Methacrylate Production):

CH₂=C(CH₃)-COOH + CH₃OH → CH₂=C(CH₃)-COOCH₃ + H₂O

4. PRODUCTION PROCESS

Method Description
Acetone Cyanohydrin Method (Traditional) Acetone + HCN → Acetone cyanohydrin → Methacrylamide sulfate → Methacrylic acid
Isobutylene Oxidation (Most Common) Isobutylene + O₂ → Methacrolein + O₂ → Methacrylic acid (two-step oxidation)
tert-Butanol Oxidation tert-Butanol can be used instead of isobutylene
Methacrylonitrile Hydrolysis Isobutylene → Methacrylonitrile → Hydrolysis → Methacrylic acid
Isobutane Oxidation Isobutane → Methacrolein → Oxidation → Methacrylic acid

Reaction Equations:

Acetone Cyanohydrin Method:

(CH₃)₂CO + HCN → (CH₃)₂C(OH)CN
(CH₃)₂C(OH)CN + H₂SO₄ → CH₂=C(CH₃)-CONH₂·H₂SO₄
CH₂=C(CH₃)-CONH₂·H₂SO₄ + H₂O → CH₂=C(CH₃)-COOH + (NH₄)₂SO₄

Isobutylene Oxidation (Most Common):

(CH₃)₂C=CH₂ + O₂  —[Catalyst]—> CH₂=C(CH₃)-CHO (Methacrolein) + H₂O
CH₂=C(CH₃)-CHO + 0.5 O₂ —[Catalyst]—> CH₂=C(CH₃)-COOH

5. AVAILABLE FORMS AND SPECIFICATIONS

Form Stabilizer Purity Applications
Stabilized Liquid MEHQ 250 ppm ≥99.0% General industrial use, polymerization
Extra Pure MEHQ 250 ppm ≥99.5% Laboratory, specialty synthesis
Inhibited Hydroquinone ≥99.0% Storage and transport

Typical Specifications (Stabilized Grade):

Parameter Specification Test Method
Assay (C₄H₆O₂) ≥99.0% GC
Appearance Colorless clear liquid Visual
Color (APHA) ≤10 Colorimetric
Density (25°C) 1.013 - 1.017 g/mL Hydrometer
Refractive Index (n20/D) 1.430 - 1.432 Refractometer
Water Content ≤0.3% Karl Fischer
MEHQ Content 200 - 300 ppm HPLC
Freezing Point 12-16°C DSC
Acidity (as Methacrylic acid) ≥99.0% Titration
Dimer Content ≤0.1% GC
Inhibitor (MEHQ) 250 ± 50 ppm HPLC

6. APPLICATIONS

6.1. Methyl Methacrylate (MMA) Production – Largest Use (~60%)

Application Function
Methyl Methacrylate (MMA) Esterification with methanol
Organic Glass (Plexiglas) Aircraft windows, civil building windows
Cast Acrylic Sheets Signs, displays, aquariums, glazing
Molding Powders Injection molding, extrusion
Buttons Processed from MMA polymer
Solar Filters UV protection
Automotive Light Lenses Headlight covers, taillight lenses

6.2. Methacrylate Esters Production

Application Function
Ethyl Methacrylate Polymer production
Butyl Methacrylate Coatings, adhesives
Hydroxyethyl Methacrylate (HEMA) Contact lenses, hydrogels
Hydroxypropyl Methacrylate (HPMA) Biomedical applications
Glycidyl Methacrylate (GMA) Epoxy functional polymers

6.3. Coatings and Paints

Application Function
Acrylic Coatings Superior suspension, rheology, and durability
Waterborne Coatings Emulsion polymers
Automotive Coatings High-performance topcoats
Industrial Coatings Corrosion protection
Powder Coatings Crosslinking agent
Textile Coatings Fabric finishing

6.4. Adhesives and Binders

Application Function
Metal Adhesion Binding metal surfaces
Leather Adhesives Bonding leather materials
Plastic Adhesives Plastic bonding
Construction Adhesives Building materials adhesion
Dental Adhesives Dental cements and composites
Medical Adhesives Surgical adhesives

6.5. Polymer Emulsions and Textile Finishing

Application Function
Fabric Finishing Agents Improves fabric properties
Antistatic Agents Reduces static electricity
Paper Coatings Improves paper quality
Leather Finishing Leather treatment
Carpet Backing Binder for carpet fibers

6.6. Synthetic Rubber

Application Function
Methacrylate-Butadiene Rubber Synthetic rubber production
Impact Modifiers Improves impact resistance of plastics
Acrylic Rubber Heat and oil resistant elastomers
Tire Additives Improves tire properties

6.7. Ion Exchange Resins

Application Function
Cation Exchange Resins Water treatment
Water Softening Hardness removal
Demineralization Pure water production
Specialty Resins Metal recovery, pharmaceutical separation

6.8. Polymer Additives and Functional Materials

Application Function
Thickeners Viscosity modification
Dispersants Pigment dispersion
Superabsorbent Polymers Diapers, hygiene products
Hydrogels Contact lenses, drug delivery, wound dressings
Dental Materials Fillings, crowns, adhesives
Orthopedic Bone Cements Bone fixation

6.9. Insulating Materials

Application Function
Electrical Insulation Wire and cable coatings
Electronic Encapsulants Circuit board protection
Transformer Insulation Dielectric materials

6.10. Other Applications

Application Function
Organic Reagent Laboratory synthesis
Polymer Intermediate Production of high-molecular polymers
Resin Production Thermoset and thermoplastic resins
Plastic Production Specialty plastics
Pharmaceutical Intermediates Drug synthesis
Agricultural Chemicals Pesticide intermediates

7. DERIVATIVES AND DOWNSTREAM PRODUCTS

Derivative Application
Methyl Methacrylate (MMA) Organic glass (Plexiglas), molding powders, coatings
Ethyl Methacrylate Polymers, coatings
Butyl Methacrylate Adhesives, coatings
Hydroxyethyl Methacrylate (HEMA) Contact lenses, hydrogels, biomedical
Hydroxypropyl Methacrylate (HPMA) Biomedical applications
Glycidyl Methacrylate (GMA) Epoxy resins, crosslinkers
Methacrylamide Polymer production
Poly(methacrylic acid) Thickeners, dispersants, superabsorbents
Methacrylate Salts Water treatment, detergents

8. QUALITY SPECIFICATIONS (Industrial Grade)

Parameter Specification Test Method
Assay (C₄H₆O₂) ≥99.0% GC
Appearance Colorless clear liquid Visual
Color (APHA) ≤10 ASTM D1209
Density (25°C) 1.013 - 1.017 g/mL ASTM D4052
Refractive Index (n20/D) 1.430 - 1.432 ASTM D1218
Water Content ≤0.3% Karl Fischer
MEHQ (Stabilizer) 200 - 300 ppm HPLC
Freezing Point 12 - 16°C DSC
Acidity (as MAA) ≥99.0% Titration
Dimer Content ≤0.1% GC
Iron (Fe) ≤1 ppm ICP

9. STORAGE AND HANDLING

Parameter Information
Storage Temperature +15°C to +25°C
Storage Conditions Store at room temperature (15-25°C); avoid freezing
Container Requirements Polyethylene-lined aluminum, glass, or stainless steel containers
Protect from Moisture, light, heat, polymerization initiators, strong oxidizers
Stabilizer MEHQ (250 ppm) or hydroquinone required
Shelf Life ~3 months (unopened, proper storage)
Freezing Note Solidifies below 12-16°C; thaw at room temperature (~25°C)
Incompatible Materials Strong oxidizing agents, strong bases, amines, peroxides, polymerization initiators
Packaging Options 200 kg drum (lined or stainless steel), IBC, bulk tanker

Handling Notes:

  • Must contain stabilizer (MEHQ or hydroquinone) to prevent polymerization

  • In the absence of stabilizer, will readily polymerize (exothermic, potentially explosive)

  • Solidifies below 12-16°C; thaw at room temperature (approx. 25°C) – do not overheat

  • Use only stainless steel or glass equipment; avoid copper, brass, or iron

  • Keep away from heat, sparks, and open flames

  • Use explosion-proof electrical equipment

  • Ensure good ventilation

  • Use with adequate personal protective equipment

10. SAFETY AND HEALTH INFORMATION (GHS CLASSIFICATION)

Hazard Class Category
Corrosive Category 1B (H314)
Acute Toxicity (Oral) Category 4 (H302)
Acute Toxicity (Dermal) Category 4 (H312)
Acute Toxicity (Inhalation) Category 4 (H332)
Skin Corrosion Category 1B (H314)
Serious Eye Damage Category 1 (H318)
Respiratory Irritation Category 3 (H335)
Flammable Liquid Category 4 (H227)

11. HAZARD STATEMENTS (H-CODES)

Code Statement
H227 Combustible liquid
H302 Harmful if swallowed
H312 Harmful in contact with skin
H314 Causes severe skin burns and eye damage
H318 Causes serious eye damage
H332 Harmful if inhaled
H335 May cause respiratory irritation

12. SAFETY STATEMENTS (P-CODES)

Code Statement
P210 Keep away from heat, hot surfaces, sparks, open flames, and other ignition sources. No smoking
P261 Avoid breathing dust/fumes/vapor
P280 Wear protective gloves, protective clothing, eye protection, face protection
P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
P302+P352 IF ON SKIN: Wash with plenty of water
P303+P361+P353 IF ON SKIN (or hair): Remove immediately all contaminated clothing. Rinse skin with water
P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing
P310 Immediately call a POISON CENTER or doctor
P363 Wash contaminated clothing before reuse

13. TOXICOLOGICAL INFORMATION

Parameter Value
Oral LD50 (rat) 1,060 - 1,320 mg/kg
Oral LD50 (mouse) 1,250 mg/kg
Dermal LD50 (rabbit) 500 - 1,000 mg/kg
Inhalation LC50 (rat) >3.8 mg/L (4 hours)
Skin Corrosion Causes severe burns
Eye Damage Causes serious eye damage
Skin Sensitization May cause sensitization
Carcinogenicity No carcinogenic effects found
Mutagenicity Negative

Health Effects:

Exposure Effect
Acute (Inhalation) Respiratory tract irritation, coughing, shortness of breath
Acute (Skin Contact) Severe burns, blistering, dermatitis
Acute (Eye Contact) Severe burns, corneal damage, potential blindness
Acute (Ingestion) Severe gastrointestinal burns, nausea, vomiting
Chronic Possible skin sensitization

Occupational Exposure Limits:

Agency Limit
ACGIH TLV TWA 20 ppm (~70 mg/m³)
Workplace Limit 100 ppm (temporary working area)

14. FIRST AID MEASURES

Exposure Route Action
Inhalation Remove to fresh air. Give oxygen if breathing difficulty. Seek immediate medical attention.
Skin Contact Remove contaminated clothing. Wash with soap and plenty of water for at least 15 minutes. Seek immediate medical attention.
Eye Contact Rinse immediately with plenty of water for at least 15 minutes. Remove contact lenses. Seek immediate medical attention.
Ingestion Do NOT induce vomiting. Rinse mouth. Do not give anything by mouth. Seek immediate medical attention.

15. FIRE FIGHTING MEASURES

Parameter Information
Fire Hazard Combustible liquid (flash point 77°C)
Explosion Hazard Can form explosive mixtures with air; explosive limit 1.6-8.7%(V)
Extinguishing Media Water mist, CO₂, dry chemical powder, alcohol-resistant foam
Special Hazards May polymerize and explode if heated in container; toxic gases (CO, CO₂)
Protective Equipment Self-contained breathing apparatus (SCBA), full protective clothing

16. ENVIRONMENTAL INFORMATION

Parameter Information
Aquatic Toxicity Toxic to aquatic organisms
Biodegradability Readily biodegradable
Bioaccumulation Low potential
Mobility in Soil Moderate
Waste Disposal Dispose according to local regulations. Controlled incineration recommended.

17. TRANSPORT INFORMATION

Parameter Information
UN Number 2531
Hazard Class 8 (Corrosive substance)
Packing Group II
Proper Shipping Name METHACRYLIC ACID, STABILIZED
Marine Pollutant No
ADR/RID Label 8
EMS F-A, S-B

18. REGULATORY INFORMATION

Region Status
EU REACH registered; industrial use approved
USA (TSCA) Listed
Canada (DSL) Listed
Australia (AICS) Listed
Japan (ENCS) Listed
Korea (KECL) Listed
China (IECSC) Listed

EINECS: 201-204-4

RTECS: OZ2975000

HS Code: 2916 13 00

19. OTHER NAMES AND SYNONYMS

Name
Methacrylic Acid
Methylacrylic Acid
2-Methylacrylic Acid
α-Methylacrylic Acid
2-Methylpropenoic Acid
2-Methyl-2-propenoic acid
alpha-Methylacrylic acid
Methacrylic acid, stabilized
Methacrylic acid, extra pure
2-Methylprop-2-enoic acid

Database Identifiers:

Database Identifier
CAS 79-41-4
EC 201-204-4
MDL MFCD00002651
PubChem CID 4093
RTECS OZ2975000
UN 2531
Beilstein 1719937
Merck 14,5941

20. SUMMARY AND IMPORTANT WARNINGS

SUMMARY:

Methacrylic acid (MAA, C₄H₆O₂, CAS 79-41-4) is a colorless clear liquid with a repulsive, acrid odor. It contains both a carboxylic acid group and a vinyl double bond, making it a versatile monomer and chemical intermediate. It has a melting point of 12-16°C and boiling point of 163°C. Methacrylic acid is stabilized with MEHQ (250 ppm) or hydroquinone to prevent premature polymerization. The largest application (~60%) is the production of methyl methacrylate (MMA) for organic glass (Plexiglas). Other applications include methacrylate esters, coatings, adhesives, polymer emulsions, synthetic rubber, ion exchange resins, and functional polymers.

Key Properties:

Property Value
Appearance Colorless clear liquid
Chemical Formula C₄H₆O₂
Molecular Weight 86.09 g/mol
Melting Point 12-16°C (14°C typical)
Boiling Point 159-163°C
Density 1.015 g/mL (25°C)
Flash Point 77°C (170°F)
Water Solubility 9.7 g/100 mL (20°C)
pKa 4.66 (25°C)
Stabilizer MEHQ (250 ppm) or hydroquinone
Primary Use Methyl methacrylate (MMA) production

Main Application Areas:

Industry Applications
MMA Production Organic glass (Plexiglas), acrylic sheets, molding powders
Methacrylate Esters Ethyl, butyl, HEMA, HPMA, GMA
Coatings Acrylic coatings, automotive, industrial, powder coatings
Adhesives Metal, leather, plastic, construction, dental, medical
Polymer Emulsions Fabric finishing, antistatic agents, paper coatings
Synthetic Rubber Impact modifiers, acrylic rubber, tire additives
Ion Exchange Resins Water treatment, demineralization
Functional Polymers Superabsorbents, hydrogels, dental materials

Key Safety Points:

  • CORROSIVE: Causes severe skin burns and eye damage (H314, H318)

  • HARMFUL: Harmful if swallowed, in contact with skin, or if inhaled (H302, H312, H332)

  • POLYMERIZATION HAZARD: Readily polymerizes without stabilizer; can be explosive

  • COMBUSTIBLE: Flash point 77°C; can form explosive mixtures with air (1.6-8.7%)

  • USE STABILIZER: Do not use without MEHQ or hydroquinone

  • USE PPE: Chemical goggles, face shield, acid-resistant gloves (neoprene, nitrile), protective clothing

  • USE VENTILATION: Work in fume hood or well-ventilated area

  • STORAGE: 15-25°C; do not freeze (solidifies below 12-16°C)

IMPORTANT WARNINGS:

Polymerization Hazard: Methacrylic acid readily polymerizes in the absence of a stabilizer. Polymerization is exothermic and can become explosive, especially in closed containers. MUST contain MEHQ (250 ppm) or hydroquinone as stabilizer. Never use unstabilized methacrylic acid. High temperatures, light, peroxides, and polymerization initiators can trigger polymerization.

Corrosive Properties: Methacrylic acid is corrosive and causes severe skin burns and eye damage. Use appropriate personal protective equipment including chemical goggles, face shield, acid-resistant gloves, and protective clothing.

Solidification: Methacrylic acid solidifies below 12-16°C. If frozen, thaw at room temperature (approx. 25°C). Do not overheat; do not use direct flame or steam to thaw.

Storage: Store at room temperature (15-25°C). DO NOT FREEZE. Store away from heat, light, strong oxidizing agents, strong bases, amines, peroxides, and polymerization initiators. Store in polyethylene-lined aluminum, glass, or stainless steel containers. Avoid copper, brass, or iron equipment.

Combustible Liquid: Flash point 77°C. Can form explosive mixtures with air (explosive limit 1.6-8.7%). Use explosion-proof electrical equipment. Keep away from heat, sparks, and open flames.

Methyl Methacrylate (MMA): The most important derivative of methacrylic acid is methyl methacrylate (MMA), which is used to produce organic glass (Plexiglas). MMA polymer is known for its optical clarity, weather resistance, and durability, making it suitable for aircraft windows, automotive light lenses, solar filters, and buttons.

Coatings: Methacrylic acid-based coatings have superior suspension properties, rheology control, and durability. They are used in automotive topcoats, industrial coatings, and waterborne paints.

Ion Exchange Resins: Methacrylic acid is used in the production of cation exchange resins for water softening and demineralization.

Biomedical Applications: Methacrylate derivatives such as HEMA (hydroxyethyl methacrylate) are used in contact lenses, hydrogels, drug delivery systems, and bone cements.

Flammable Limits: Lower explosive limit 1.6%, upper explosive limit 8.7%. Vapors are heavier than air and may travel along the ground to ignition sources.

Important Disclaimer: This Technical Data Sheet (TDS) is for informational purposes only. For complete safety, handling, storage, and regulatory compliance information, always refer to the official Safety Data Sheet (SDS) provided by the manufacturer/supplier. Methacrylic acid MUST be stored and handled with a stabilizer (MEHQ or hydroquinone). Never use unstabilized material. In case of polymerization, evacuate area immediately.

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