Methyl Methacrylate
Methyl methacrylate (MMA) is a flammable liquid that can be used for paint, coatings, adhesives and medical applications. Lightweight, stress-resistant, and able to withstand years of UV and weather exposure, PMMA is a common replacement for glass. It is also used for flat screen televisions, liquid crystal displays (LCDs), and optical fibres.
- CAS Number: 80-62-6
- Assay (GC, area%): ≥ 99.0 % (a/a)
- Density (d 20 °C/ 4 °C): 0.942 – 0.944
- Molar Mass: 100.12 g/mol
- Chemical Formula: CH₂=C(CH₃)COOCH₃
- Hill Formula: C₅H₈O₂
- Synonyms: Methyl 2-methylpropenoate, Methacrylic acid methyl ester, MMA
- Identity (IR): passes test
Description
Methyl methacrylate (MMA) refers to an organic compound that contains a methyl ester of methacrylic acid. Its chemical formula is C5H8O2. Methyl methacrylate is a reactive resin and its polymerized form has useful applications, such as:
- Adhesives and sealants
- Protective coating
- Industrial paints
- Plastic additives
- Polymethyl methacrylate acrylic plastics
- Synthetic marble
- Bonding cement
Methyl methacrylate provides the following benefits to the finished product:
- Stability and durability
- Hardness and impact
- Scratch resistance and brilliance
Methyl methacrylate (MMA) is a polymerized form of resins or organic materials principally used in the production of polymethyl methacrylate acrylic plastics (PMMA) and methyl methacrylate-butadiene-styrene (MBS). It was also later used as a PVC modifier. MMA is a volatile, flammable and colorless liquid, and is soluble in warm water. It has an acrid odor.
Depending on the original monomer from which the polymer was built, acrylics come in two categories: acrylates and methacrylates. In MMA, a methyl group is attached to the carbon-carbon chain of the polymer molecule of a methacrylate, whereas a hydrogen atom is found in the carbon-carbon chain in the acrylate.
The copolymerization of MMA, such as poly(methyl methacrylate), is resistant to saponification, or alkali breakdown. As a result, it is a highly desirable polymer for coating zinc substrates or any surfaces where alkali conditions may arise. To make a suitable paint from MMA, there needs to be some modification of the copolymer. Note that the elongation of pure methyl methacrylate is very low for both solvent-borne and waterborne coatings. Therefore, in waterborne formulations of methyl methacrylate emulsion polymers, one needs to mix large quantities of plasticizers, coalescing solvents, or both to form films at room temperature. On the other hand, acrylic emulsion polymers must be copolymerized with acrylate monomers for paint formulations.
A reactive acrylic adhesive is manufactured from methyl methacrylate, which cures quickly at room temperature and builds strength rapidly. Due to its excellent resistance to shear, peel, impact stresses and quick cure, it is widely used in the structural bonding of advanced materials in the aerospace, automotive and composites industries.
Methyl methacrylate is used as a monomer in the manufacturing of poly(methyl methacrylate) (PMMA). It is also used in the manufacturing of the co-polymer methyl methacrylate-butadiene-styrene (MBS), which is a modifier for polyvinyl chloride. It plays an important role as the cement used in total hip replacements as well as total knee replacements. It is also involved in the preparation of other methacrylates viz. ethyl methacrylate (EMA), butyl methacrylate (BMA) and 2-ethyl hexyl methacrylate (2-EHMA) and methacrylic acid (MAA), which finds application as an intermediate in the manufacture of coating polymers and textile applications.This Thermo Scientific brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific.
Methyl methacrylate is used as a monomer in the manufacturing of poly(methyl methacrylate) (PMMA). It is also used in the manufacturing of the co-polymer methyl methacrylate-butadiene-styrene (MBS), which is a modifier for polyvinyl chloride. It plays an important role as the cement used in total hip replacements as well as total knee replacements. It is also involved in the preparation of other methacrylates viz. ethyl methacrylate (EMA), butyl methacrylate (BMA) and 2-ethyl hexyl methacrylate (2-EHMA) and methacrylic acid (MAA), which finds application as an intermediate in the manufacture of coating polymers and textile applications.
Solubility
Slightly miscible with water.
Notes
Incompatible with oxidizing agents, peroxides, amines, bases, acids, reducing agents and halogens.
Methyl methacrylate – Names and Identifiers
Name | Methyl methacrylate |
Synonyms | MMA METHYL METACRYLATE Methyl methacrylate Methyl Methyl Acrylate Methacrylic acid methyl ester 2-Methylacrylic acid methyl ester |
CAS | 80-62-6 |
EINECS | 201-297-1 |
InChI | InChI=1/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3 |
Methyl methacrylate – Physico-chemical Properties
Molecular Formula | C5H8O2 |
Molar Mass | 100.12 |
Density | 0.943 |
Melting Point | -48℃ |
Boling Point | 100℃ |
Flash Point | 8℃ |
Water Solubility | 15.9 g/L (20℃) |
Refractive Index | 1.413 |
Physical and Chemical Properties | Characteristics of colorless liquid, volatile. melting point -48 ℃ boiling point 100~101 ℃ relative density 0.9440 refractive index 1.4142 flash point 10 ℃ solubility, ether, acetone and other organic solvents. Slightly soluble in ethylene glycol and water. |
Use | It is mainly used as a monomer of organic glass, and is also used to make other plastics, coatings, etc. |
Methyl methacrylate – Risk and Safety
Hazard Symbols | F – Flammable Xi – Irritant |
Risk Codes | R11 – Highly Flammable R37/38 – Irritating to respiratory system and skin. R43 – May cause sensitization by skin contact |
Safety Description | S24 – Avoid contact with skin. S37 – Wear suitable gloves. S46 – If swallowed, seek medical advice immediately and show this container or label. |
UN IDs | UN 1247 |
Methyl methacrylate – Upstream Downstream Industry
Raw Materials | Acetone cyanohydrin Methyl alcohol Methyl alcohol Sulfuric acid Sulfuric acid Sodium cyanide Sodium cyanide |
Methyl methacrylate – Nature
colorless liquid, volatile, flammable. The relative density was 0.9440. Melting Point -48 °c. Boiling point 100~101 deg C. Flash point (Open Cup) 10 °c. Refractive index 4142. Vapor pressure (25.5 C) 5.33kPa. Soluble in ethanol, ether, acetone and other organic solvents. Slightly soluble in ethylene glycol and water. Polymerization is facilitated in the presence of light, heat, ionizing radiation and catalysts.
Methyl methacrylate – Preparation Method
- acetone cyanohydrin route acetone cyanohydrin reacts with sulfuric acid to generate methacrylamide sulfate, which is hydrolyzed and then esterified with methanol to obtain methyl methacrylate crude product, which is then subjected to salting-out, crude distillation and rectification to obtain finished product. Acetone cyanohydrin is usually prepared from sodium cyanide.
- isobutylene route isobutylene is two-stage oxidized with air in the presence of a molybdenum catalyst. Isobutene is first oxidized to methacrolein and then further oxidized to methacrylic acid. Methyl methacrylate was obtained by esterification of methacrylic acid with methanol. Recently, a one-step oxidation process has been developed. Isobutene was directly oxidized to methacrylic acid with N2 04 as oxidant and K2 C03 or Mr102 as catalyst. This was then esterified with methanol.
- propylene route propylene, carbon monoxide and methanol are subjected to carbonylation reaction to generate 2 methoxy isobutyric acid methyl ester, and then decomposed into methyl methacrylate and methanol by hydrolysis reaction.
- one-step oxidation of isobutyraldehyde using Heteropoly acid and its salts as catalyst, one-step oxidation of isobutyraldehyde to produce methacrylic acid, methacrylic acid and methanol esterification into methyl methacrylate.
Methyl methacrylate – Use
The monomer of organic glass is also used in the manufacture of other resins, plastics, coatings, adhesives, lubricants, Wood wetting agents, motor coil penetration agents, paper glazing agents, printing and dyeing aids and insulation infusion materials.
Methyl methacrylate – Safety
- This product is less toxic. The oral LD50 in rats was 9400mg/kg. The inhalation lethal concentration is lc5015.33 g/m3, and the maximum allowable concentration is 410mg/m3. But its olfactory threshold is 130 ~ 250mg/m3, when its concentration has not yet reached before the production of toxicity, its strong odor has been intolerable. Human skin contact with methyl methacrylate, only a very small number of people will appear red rash. As the raw material of methyl methacrylate and the intermediate hydrogen cyanide are highly toxic, the production unit must strictly ensure that the equipment is sealed and well ventilated. The operator should be strictly Protection Measure and equipped with necessary protective equipment. Found that the phenomenon of poisoning should be immediately moved to fresh air and timely rescue.
- zinc-coated iron drum or aluminum drum packaging. Size 16 0kg. Store in a cool and ventilated special warehouse, away from fire and heat source, and avoid direct sunlight.
- Other Names
-
- 2-(Methoxycarbonyl)-1-propene
- 2-Methyl-2-propenoic acid methyl ester
- 2-Methylacrylic acid, methyl ester
- 2-Methylacrylic, methyl ester
- 2-Propenoic acid, 2-methyl-, methyl ester
- 2-methylpropenoic acid, methyl ester
- Acryester M
- Acrylic acid, 2-methyl-, methyl ester
- CH2=C(CH3)COOCH3
- Diakon
- MMA
- Metakrylan metylu
- Methacrylate de methyle
- Methacrylic acid methyl ester
- Methacrylsaeuremethyl ester
- Methyl 2-methyl-2-propenoate
- Methyl 2-methylpropenoate
- Methyl ester of 2-methyl-2-propenoic acid
- Methyl methacrylate monomer
- Methyl methylacrylate
- Methyl «alpha»-methylacrylate
- Methyl «alpha»-methylacrylate
- Methyl-methacrylat
- Methyl-«alpha»-methacrylate
- Methyl-«alpha»-methacrylate
- Methylester kyseliny methakrylove
- Methylmethacrylaat
- Metil metacrilato
- Monocite methacrylate monomer
- NCI-C50680
- NSC 4769
- Paladon
- Pegalan
- Rcra waste number U162
- TEB 3K
- methacrylic acid, methyl ester
- PAff : Proton affinity (kJ/mol).
- BasG : Gas basicity (kJ/mol).
- ΔcH°liquid: Standard liquid enthalpy of combustion (kJ/mol).
- Cp,gas: Ideal gas heat capacity (J/mol×K).
- Cp,liquid: Liquid phase heat capacity (J/mol×K).
- Cp,solid: Solid phase heat capacity (J/mol×K).
- η : Dynamic viscosity (Pa×s).
- ΔfG° : Standard Gibbs free energy of formation (kJ/mol).
- ΔfH°gas: Enthalpy of formation at standard conditions (kJ/mol).
- ΔfH°liquid: Liquid phase enthalpy of formation at standard conditions (kJ/mol).
- ΔfusH° : Enthalpy of fusion at standard conditions (kJ/mol).
- ΔfusH : Enthalpy of fusion at a given temperature (kJ/mol).
- ΔsubH : Enthalpy of sublimation at a given temperature (kJ/mol).
- ΔvapH° : Enthalpy of vaporization at standard conditions (kJ/mol).
- ΔvapH : Enthalpy of vaporization at a given temperature (kJ/mol).
- IE : Ionization energy (eV).
- log10WS : Log10 of Water solubility in mol/l.
- logPoct/wat: Octanol/Water partition coefficient.
- McVol : McGowan’s characteristic volume (ml/mol).
- Pc: Critical Pressure (kPa).
- Pvap: Vapor pressure (kPa).
- ρl: Liquid Density (kg/m3).
- Inp: Non-polar retention indices.
- I : Polar retention indices.
- ΔfusS : Entropy of fusion at a given temperature (J/mol×K).
- S°liquid: Liquid phase molar entropy at standard conditions (J/mol×K).
- csound,fluid: Speed of sound in fluid (m/s).
- Tboil: Normal Boiling Point Temperature (K).
- Tc: Critical Temperature (K).
- Tfus: Normal melting (fusion) point (K).
- Ttriple: Triple Point Temperature (K).
- Vc: Critical Volume (m3/kmol).
Synonyms
Methyl methacrylate, 99%, stab.
Chemical Properties
Applications
Methyl methacrylate is used as a monomer in the manufacturing of poly(methyl methacrylate) (PMMA). It is also used in the manufacturing of the co-polymer methyl methacrylate-butadiene-styrene (MBS), which is a modifier for polyvinyl chloride. It plays an important role as the cement used in total hip replacements as well as total knee replacements. It is also involved in the preparation of other methacrylates viz. ethyl methacrylate (EMA), butyl methacrylate (BMA) and 2-ethyl hexyl methacrylate (2-EHMA) and methacrylic acid (MAA), which finds application as an intermediate in the manufacture of coating polymers and textile applications.
Notes
GHS Hazard and Precautionary Statements
Hazard Statements: H225-H315-H317-H319-H335
Highly flammable liquid and vapour. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: 33784-86698-P210-P233-P235-P240-P241-P242-P243-P264b-P271-P272-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P333+P313-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. – No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant.
Other References
Product Specification
Form: Liquid
Assay (GC): ≥98.5% min
Identification (FTIR): Conforms
Refractive Index: 1.4135-1.4165 @ 20°C
Solution Test: 10% in Diethyl ether: Clear
Solution Test: 10% in Methanol: Clear
UN Number (DOT-AIR) | UN1247 |
Class (DOT-AIR) | 3 |
Packing Group (TCI-A) | II |
HS Number | 2916.14.2020 |
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