Quick Search
Methacrylic acid isobutyl ester is an organic compound that is an ester derived from methacrylic acid and isobutanol.
Methacrylic acid isobutyl ester is a colorless liquid with a characteristic ester odor, commonly used as a monomer in the production of polymers and copolymers, especially in coatings, adhesives, and plastics industries.
Methacrylic acid isobutyl ester provides desirable properties such as flexibility, toughness, and chemical resistance in polymer products.
CAS Number:
97-85-8
Synonyms:
Isobutyl Methacrylate,Methacrylic Acid, Isobutyl Ester,2-Methylpropyl Methacrylate
Isobutyl 2-methylpropenoate,2-Methylpropyl 2-methylpropenoate,Isobutyl 2-methylacrylate
Abstract
Methacrylic Acid Isobutyl Ester, or Isobutyl Methacrylate (IBMA), is a key monomer in the family of alkyl methacrylates with extensive applications in polymer science and industrial manufacturing.
This article provides a comprehensive review of IBMA’s chemical structure, physical and chemical properties, synthetic methods, polymerization behavior, and the material properties of its derived polymers.
Furthermore, industrial applications such as coatings, adhesives, sealants, and specialty plastics are discussed in detail.
Environmental and safety aspects of IBMA are also critically evaluated, alongside analytical techniques for its identification and quantification.
Recent research trends and challenges in IBMA utilization, including sustainability and green chemistry approaches, are explored.
This review aims to provide scientists, engineers, and industrial practitioners with an in-depth understanding of IBMA’s role in modern polymer technology and its future development potential.
Introduction
Methacrylic Acid Isobutyl Ester (IBMA), systematically known as 2-methylpropyl 2-methylpropenoate, belongs to the class of alkyl methacrylates, esters derived from methacrylic acid and various alcohols.
IBMA is distinguished by its isobutyl alkyl group, which affects the physical and chemical behavior of both the monomer and its resultant polymers.
Methacrylic esters, since their commercial introduction in the mid-20th century, have revolutionized the polymer industry.
Methacrylate-based polymers offer a wide spectrum of mechanical, optical, and chemical properties that can be finely tuned by selecting appropriate ester groups and copolymer compositions.
IBMA, with its branched isobutyl group, imparts increased flexibility, toughness, and hydrophobicity compared to simpler methacrylates like methyl or ethyl methacrylate.
IBMA's unique structure translates into versatile polymer characteristics, making it an essential monomer in applications ranging from high-performance coatings and adhesives to impact modifiers and specialty plastics.
The balance of hydrophobicity and flexibility supports its use in environments requiring resistance to moisture, chemicals, and mechanical stress.
This article comprehensively reviews the current state of knowledge on IBMA, focusing on its chemical and physical properties, synthesis, polymerization, applications, safety, and environmental impact.
The review also addresses the analytical methods utilized for IBMA detection and quantification, which are crucial for quality control and regulatory compliance.
Chemical Structure and Properties
Molecular Formula and Weight
Methacrylic Acid Isobutyl Ester has the molecular formula C8H14O2 and a molecular weight of approximately 142.20 g/mol.
It is a colorless, volatile liquid with moderate solubility in organic solvents and negligible solubility in water.
Chemical Structure and Stereochemistry
IBMA is an ester formed by the condensation of methacrylic acid and isobutanol.
The methacrylic moiety contains a vinyl group adjacent to a carbonyl, which is responsible for the monomer’s high reactivity in radical polymerization.
The isobutyl ester group is branched, consisting of a tertiary carbon, which influences the steric environment around the polymerizable double bond.
Physical Properties
Boiling Point: Approximately 170–175 °C at atmospheric pressure
Melting Point: Typically below -60 °C, indicating a liquid state at room temperature
Density: Around 0.87 g/cm³ at 20 °C
Refractive Index: Approximately 1.41
Vapor Pressure: Moderate volatility at room temperature
Spectroscopic Characteristics
NMR: Proton NMR spectra exhibit characteristic signals corresponding to the vinyl protons, methyl groups on the isobutyl chain, and methylene groups.
Carbon-13 NMR confirms the ester carbonyl and alkyl carbons.
IR: Strong absorption bands near 1720 cm⁻¹ for ester C=O stretching; C=C stretching observed around 1635 cm⁻¹; methyl and methylene C-H stretching around 2950–2850 cm⁻¹.
Mass Spectrometry: Molecular ion peak at m/z 142 with fragmentation patterns consistent with loss of isobutyl groups and vinyl fragments.
Synthesis Methods
Industrial Production Routes
IBMA is primarily produced industrially via esterification of methacrylic acid with isobutanol in the presence of acid catalysts such as sulfuric acid, para-toluenesulfonic acid, or solid acid resins.
The reaction is typically conducted under reflux with continuous removal of water to drive equilibrium toward ester formation.
Laboratory Synthesis
In laboratory settings, IBMA can be synthesized using Fischer esterification with methacrylic acid and isobutanol under acidic conditions, or via transesterification of methyl methacrylate with isobutanol catalyzed by metal alkoxides.
Catalysts and Reaction Conditions
Strong acid catalysts accelerate the esterification process, with typical temperatures ranging from 80 °C to 130 °C.
Removal of water by azeotropic distillation or use of molecular sieves enhances yield.
Solid acid catalysts offer advantages in terms of easier separation and recyclability.
Purification Techniques
Purification of IBMA involves fractional distillation under reduced pressure to separate it from unreacted alcohol, acid, and side products.
Additional purification by washing with sodium bicarbonate solution neutralizes residual acid catalysts.
SAFETY INFORMATION ABOUT METHACRYLIC ACID ISOBUTYL ESTER
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
