Methyl Methacrylate's uses, from the production of transparent, durable plastics and coatings to its function in adhesives and medical applications.
Methyl Methacrylate is used to make plastics.
Methyl Methacrylate is used as a bone cement.
CAS Number: 80-62-6
EC Number: 201-297-1
Molecular Formula: C5H8O2 / CH2C(CH3)COOCH3
Molecular Weight: 100.12 g/mol
SYNONYMS:
methacrylate monomer, methyl ester of methacrylic acid, methyl methacrylate monomer, uninhibited, methyl-2-methyl-2-propenoate, MMA, 2-(methoxycarbonyl)-1-propene, 2-Propenoic acid, 2-methyl-, methyl ester, Methacrylic acid methyl ester, Diakon, Methyl 2-methyl-2-propenoate, Methyl 2-methylpropenoate, MMA, Pegalan, CH2=C(CH3)COOCH3, Methyl-α-methacrylate, Monocite methacrylate monomer, Metakrylan metylu, Methacrylate de methyle, Methacrylsaeuremethyl ester, Methyl α-methylacrylate, Methyl methylacrylate, Methyl-methacrylat, Methylmethacrylaat, Metil metacrilato, NCI-C50680, Paladon, 2-Methylacrylic acid, methyl ester, Acrylic acid, 2-methyl-, methyl ester, Methylester kyseliny methakrylove, Methyl methacrylate monomer, 2-Methyl-2-propenoic acid methyl ester, Rcra waste number U162, Methyl ester of 2-methyl-2-propenoic acid, 2-(Methoxycarbonyl)-1-propene, Acryester M, NSC 4769, TEB 3K, 2-Methylacrylic, methyl ester, Methacrylic Acid, Methyl 2-Methyl-2-Propenate, MME, MMA, 2-methylacrylic acid methyl ester, methyl methylacrylate, methyl alpha-methylacrylate, methyl 2-methylpropenoate, METHYL METHACRYLATE, 80-62-6, methyl 2-methylprop-2-enoate, Methylmethacrylate, Methyl methylacrylate, Methyl 2-methylpropenoate, Methacrylic acid methyl ester, Pegalan, Methyl-methacrylat, Diakon, Methyl 2-methyl-2-propenoate, Acryester M, Methacrylate de methyle, Methyl 2-methylacrylate, 2-Propenoic acid, 2-methyl-, methyl ester, Metakrylan metylu, Metil metacrilato, Methacrylsaeuremethyl ester, Methylmethacrylaat, 2-(Methoxycarbonyl)-1-propene, 2-Methyl-2-propenoic acid methyl ester, Rcra waste number U162, Methyl alpha-methylacrylate, Methyl methacrylate monomer, NCI-C50680, Methacrylic acid, methyl ester, Acrylic acid, 2-methyl-, methyl ester, Monocite methacrylate monomer, Methylester kyseliny methakrylove, CHEBI:34840, 2-methylacrylic acid methyl ester, DTXSID2020844, NSC-4769, DTXCID80844, 196OC77688, NSC4769, Cranioplasts, Kallocryls, Metaplices, Sintices, Methacrylate Methyl Monomer, Methacrylate monomer, Zimmer Bone Cements, Bone Cement, Zimmer, Cement, Zimmer Bone, Bone Cements, Zimmer, Cements, Zimmer Bone, Methylmethacrylate Methyl Monomer, Methacrylate Methyl Monomers, Methyl Monomer, Methacrylate, Monomer, Methacrylate Methyl, Methyl Monomers, Methacrylate, methyl-2-methyl-2-propenoate, Monomers, Methacrylate Methyl, Methyl ester of methacrylic acid, Methylmethacrylate Methyl Monomers, Methyl Monomer, Methylmethacrylate, Monomer, Methylmethacrylate Methyl, Methyl Monomers, Methylmethacrylate, Monomers, Methylmethacrylate Methyl, 2-methylmethacrylate, 2-(Methoxycarbonyl)propene, 2-Methyl Acrylic Acid Methyl Ester, 2-Propenoic acid, 2-methyl-methyl ester, 201-297-1, TEB 3K, 2-Methylacrylic acid, methyl ester, 2-Methyl-acrylic acid methyl ester, NSC 4769, MFCD00008587, Methacrylic acid-methyl ester, Methyl .alpha.-methylacrylate, 51391-19-6, Cranioplast, Metaplex, Kallocryl A, Simplex P, Methyl methacrylate monomer, inhibited, 143476-91-9, Methyl ester of 2-methyl-2-propenoic acid, 114512-63-9, 9065-11-6, Methyl Methacrylate (stabilized with 6-tert-Butyl-2,4-xylenol), Methylmethacrylaat [Dutch], Metakrylan metylu [Polish], Methyl-methacrylat [German], Metil metacrilato [Italian], CCRIS 1364, HSDB 195, Methacrylate de methyle [French], Methacrylsaeuremethyl ester [German], EINECS 201-297-1, UN1247, RCRA waste no. U162, BRN 0605459, Plexiglass, Eudragit, Methylester kyseliny methakrylove [Czech], AI3-24946, methoxymethacrolein, UNII-196OC77688, MMA (stabilized), J69, Acrylic resins (PMMA), METHYL METHACTRYLATE, Epitope ID:131321, Methyl 2-methylacrylate #, Methyl methacrylate (MMA), EC 201-297-1, Methyl-.alpha.-methacrylate, SCHEMBL1849, CH2=C(CH3)COOCH3, 4-02-00-01519 (Beilstein Handbook Reference), NA 1247 (Salt/Mix), UN 1247 (Salt/Mix), BIDD:ER0634, CHEMBL49996, Methyl methacrylate, 99.5%, SCHEMBL217190, SCHEMBL295831, SCHEMBL865215, WLN: 1UY1&VO1, Methyl methacrylate, stabilized, 'monocite' Methacrylate monomer, SCHEMBL3893737, SCHEMBL9375987, SCHEMBL10636466, Methyl methacrylate, CP,98.0%, METHYL METHACRYLATE [HSDB], METHYL METHACRYLATE [IARC], METHYLMETHACRYLATE [MART.], METHYL METHACRYLATE [VANDF], METHYLMETHACRYLATE [WHO-DD], Tox21_200367, MSK002111, SBB060556, STL283952, AKOS000120216, Methyl methacrylate, 99%, stabilized, FM34647, CAS-80-62-6, NCGC00091089-01, NCGC00091089-02, NCGC00257921-01, Methacrylic Acid Methyl Ester (stabilized), METHACRYLIC ACID METHYL ESTER [MI], DB-013559, CS-0503657, M0087, METHYL 2-METHYL-2-PROPENOATE [FHFI], NS00009302, ST51046719, EN300-19210, C19504, Methyl methacrylate 1000 microg/mL in Methanol, Methyl methacrylate, SAJ first grade, >=99.0%, A839957, Q382897, F0001-2087, InChI=1/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H, Methacrylic acid-methyl ester 100 microg/mL in Cyclohexane, Methyl Methacrylate, (stabilized with 6-tert-Butyl-2,4-xylenol), Methyl methacrylate, contains <=30 ppm MEHQ as inhibitor, 99%, Methyl methacrylate, European Pharmacopoeia (EP) Reference Standard, Methyl methacrylate (MMA), 99.5%(GC), contains 30ppm MEHQ as stabilizer, Methyl methacrylate (MMA), AR, 99.0%, contains 30ppm MEHQ as stabilizer, Methyl methacrylate monomer, inhibited [UN1247] [Flammable liquid], PROPENOIC ACID,2-METHYL,METHYLESTER (METHACRYLATE METHYLESTER), 97555-82-3, Methyl 2-methylprop-2-enoate, Methyl 2-methylpropenoate, methyl methacrylate, MMA, 2-(methoxycarbonyl)-1-propene, MMA, MME, Methacrylic acid, 2-Propenoic acid, 2-methyl-, methyl ester, 2-Propenoic Acid, 2-Methyl, Methyl Ester
Methyl Methacrylate, also known as MMA, Methacrylic acid methyl ester, or Methyl 2-methylprop-2-enoate, is an organic compound with the formula C4H8O.
Methyl Methacrylate is a clear, colorless, volatile liquid with a characteristic odor.
Methyl Methacrylate is slightly soluble in water and miscible with most organic solvents.
Methyl Methacrylate is a highly efficient and versatile solvent for thinners, cleaning agents, coatings, adhesives, plastics, construction, reactive resins, and textile treatment.
Methyl Methacrylate is inhibited with 40-50 ppm Methyl Ethyl Hydroquinone (MEHQ) to prevent polymerization.
Methyl Methacrylate is a raw material for other methacrylates, including EMA, BMA, and 2-EHMA.
Methyl methacrylate monomer appears as a clear colorless liquid.
Methyl Methacrylate is slightly soluble in water and floats on water.
Methyl Methacrylate's vapors are heavier than air.
Containers must be heavily insulated or shipped under refrigeration.
Methyl Methacrylate is an inhibitor such as hydroquinone, hydroquinone methyl ester and dimethyl t-butylphenol is added to keep the chemical from initiating polymerization.
Methyl Methacrylate may polymerize exothermically if heated or contaminated with strong acid or base.
If the polymerization takes place inside a container, the container may rupture violently.
Methyl methacrylate is an enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component.
Methyl Methacrylate has a role as an allergen and a polymerisation monomer.
Methyl Methacrylate is an enoate ester and a methyl ester.
Methyl Methacrylate is functionally related to a methacrylic acid.
Methyl methacrylate has been reported in Nicotiana tabacum and Mangifera indica with data available.
Methyl Methacrylate is a methyl ester of methacrylic acid.
Methyl methacrylate is a reactive resin, and the polymerized form is used as cement in dentistry, orthopaedic surgery and ophthalmology.
The monomer form of Methyl Methacrylate has relaxation effect on smooth muscle systemically, which might be a result of nitric oxide-mediated response.
Methyl Methacrylate is the methyl ester of methacrylic acid.
Methyl Methacrylate polymerizes easily to form POLYMETHYL METHACRYLATE.
Methyl Methacrylate is an organic compound with the formula CH2=C(CH3)COOCH3.
This colorless liquid, the methyl ester of methacrylic acid (MAA), Methyl Methacrylate, is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).
Methyl Methacrylate is a versatile chemical compound with wide-ranging applications across numerous industries.
Methyl Methacrylate has various types including: adhesives, resins, and copolymers.
Properties like: hydrophobicity, hardness, and weatherability make Methyl Methacrylate valuable in modern manufacturing and engineering.
Methyl Methacrylate, also known as methacrylic acid methyl ester, is an organic compound with the chemical formula C5H8O2.
Methyl Methacrylate is a colorless liquid with a pungent, fruity odor.
Methyl Methacrylate features a polymerizable methacrylate group and a reactive ester group, making it highly versatile for polymerization and copolymerization.
Methyl Methacrylate is slightly miscible with water, soluble in most organic solvents, and has relatively low volatility.
Methyl Methacrylate is used primarily to produce polymethyl methacrylate (PMMA), a plastic known for its clarity, durability, resistance to UV light and weathering, and its versatility as a building block in polymer chemistry.
USES and APPLICATIONS of METHYL METHACRYLATE:
Methyl Methacrylate's uses, from the production of transparent, durable plastics and coatings to its function in adhesives and medical applications.
Methyl Methacrylate is used to make plastics.
Methyl methacrylate is used in the manufacture of resins and plastics.
Methyl Methacrylate is used as a bone cement.
Methyl Methacrylate readily polymerizes to form high molecular weight homopolymers (where a polymer is created from many copies of a single monomer) and copolymers.
The principal use for Methyl Methacrylate is to form polymethyl methacrylate (PMMA) homopolymer for the production of cast and extruded acrylic sheets.
These cast PMMA sheeting products exhibit good optical clarity, high transparency, and UV stability.
Methyl Methacrylate products and applications include: Shatterproof glass replacements, Safety glazing, Panels and lighting displays, Outdoor lighting fixtures, Plumbing fixtures and components.
Outside of glazing and sheet applications, the largest use for Methyl Methacrylate is as a comonomer in paints and coatings, such as exterior paints and paper coatings.
Polymers and copolymers of methyl methacrylate are used in: Metal and foil coatings, Industrial finishes, Floor polishes, Textile finishes, Adhesives, Sealants, Construction materials, PVC impact modifiers,Packaging, and Inks.
These polymers are produced as waterborne, solvent, and dispersion resins for these applications.
Additionally, Methyl Methacrylate is used in making various coatings, adhesives, paints, and medical devices, due to its ability to impart properties such as: impact strength, weather resistance, and chemical resistance to the polymers it forms.
Methyl Methacrylate's ability to cure quickly also makes it valuable in the production of surgical cements and dental prostheses, for which rapid setting is required.
Methyl methacrylate-butadiene-styrene (MBS) resins are used as impact modifiers for clear, rigid PVC, such as bottles.
In addition, Methyl Methacrylate can partially replace styrene monomer in unsaturated polyester resins to give better weather resistance and longer outdoor life.
For products such as signage, displays, bath enclosures, spas, tabletop surfaces, automotive lights, and light fixtures, Methyl Methacrylate polymerization can be cast into a solid form.
Applications of Methyl Methacrylate also include engineering adhesives.
These are liquid, reactive, durable adhesives for bonding a variety of substrates, consisting of Methyl Methacrylate monomer with PMMA.
Low-viscosity, rapidly curing Methyl Methacrylate reactive resin systems are highly effective for sealing and filling cracks and pores in concrete surfaces and structures.
These adhesives are desired due to their ability to bond differing surfaces together, high fatigue resistance, and higher peel rate.
Methyl Methacrylate adhesives can cure at room temperature while being more temperature resistant.
Other Methyl Methacrylate applications include: Mining flocculants, Soil stabilization polymers, Waterproofing agents, and Oil field drilling fluids.
While Methyl Methacrylate can cause safety concerns when in direct contact with the skin, eyes, or respiratory system, PMMA is compatible with human tissue.
Methyl Methacrylate is used in several medical technologies such as acrylic bone cement and intraocular lenses for the eyes.
Methyl Methacrylate was once commonly used for nail enhancements.
Methyl methacrylate is used as a monomer in the manufacturing of poly(methyl methacrylate) (PMMA).
Methyl Methacrylate is also used in the manufacturing of the co-polymer methyl methacrylate-butadiene-styrene (MBS), used as a modifier for PVC.
Methyl Methacrylate plays an important role as the cement used in total hip replacements as well as total knee replacements.
Methyl Methacrylate is involved in the preparation of other methacrylates such as EMA, BMA, 2-EHMA, and MAA, which are used as intermediates in coating polymers, construction chemicals, and textile applications.
Methyl methacrylate is used as a monomer in the manufacturing of poly(methyl methacrylate) (PMMA).
Methyl Methacrylate is also used in the manufacturing of the co-polymer methyl methacrylate-butadiene-styrene (MBS), which is a modifier for polyvinyl chloride (PVC).
Methyl Methacrylate plays an important role as the cement used in total hip replacements as well as total knee replacements.
Methyl Methacrylate is involved in the preparation of other methacrylates, including ethyl methacrylate (EMA), butyl methacrylate (BMA), 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.
The principal application, consuming approximately 75% of Methyl Methacrylate, is the manufacture of polymethyl methacrylate acrylic plastics (PMMA).
Methyl Methacrylate is also used for the production of MBS, used as a modifier for PVC.
Another application of Methyl Methacrylate is as bone cement in total hip and knee replacements.
Used as the “grout” by orthopedic surgeons to secure implants into bone, Methyl Methacrylate reduces post-operative pain but has a finite lifespan, typically around 20 years before revision surgery is required.
Cemented implants are generally used in elderly populations for immediate short-term replacement, while younger patients often receive cementless implants for longer-lasting results.
Methyl Methacrylate is also used in fracture repair in small exotic animals using internal fixation.
Methyl Methacrylate is used as a chemical intermediate in the manufacture of coating polymers, construction chemicals, and textile applications.
Wood can be impregnated with Methyl Methacrylate and polymerized in situ to produce a stabilized product.
The principal application, consuming approximately 75% of the Methyl Methacrylate, is the manufacture of polymethyl methacrylate acrylic plastics (PMMA).
Methyl methacrylate is also used for the production of the co-polymer methyl methacrylate-butadiene-styrene (MBS), used as a modifier for PVC.
Another application of Methyl Methacrylate is as cement used in total hip replacements as well as total knee replacements.
Methyl Methacrylate is used as the "grout" by orthopedic surgeons to make the bone inserts fix into bone, it greatly reduces post-operative pain from the insertions but has a finite lifespan.
Typically the lifespan of methylmethacrylate as bone cement is 20 years before revision surgery is required.
Cemented implants are usually only done in elderly populations that require more immediate short term replacements.
In younger populations, cementless implants are used because their lifespan is considerably longer.
Methyl Methacrylate is also used in fracture repair in small exotic animal species using internal fixation.
Methyl Methacrylate is a raw material for the manufacture of other methacrylates.
These derivatives include ethyl methacrylate (EMA), butyl methacrylate (BMA) and 2-ethyl hexyl methacrylate (2-EHMA).
Methacrylic acid (MAA) is used as a chemical intermediate as well as in the manufacture of coating polymers, construction chemicals and textile applications.
Wood can be impregnated with MMA and polymerized in situ to produce stabilized wood.
Uses of Methyl Methacrylate: Acrylic Sheet, Paints & Coatings, Plastic Additives, and Adhesives.
Methyl Methacrylate is used for waterborne coatings, such as latex house paint.
Methyl Methacrylate is also used in adhesive formulations.
A modern application of Methyl Methacrylate is the use in plates that keep light spread evenly across LCD computer and TV screens.
Methyl methacrylate is also used to prepare corrosion casts of anatomical organs, such as coronary arteries of the heart.
Use of Methyl Methacrylate: ANTICAKING, OPACIFYING
The primary use of methyl methacrylate is the production of acrylic plastics and resins (trade names are Lucite, Plexiglas and Perspex) for sheeting and molding compounds.
These are used in construction, automotive, consumer products and in making signs.
It (methyl methacrylate-butadiene-styrene, MBS) is used as an impact modifier in PVC for bottles.
Methyl Methacrylate is also used in exterior latex housepaint, and impregnating pulp paper and wood.
Methyl Methacrylate is mainly used in the production polymethyl methacrylate acrylic plastics (PMMA).
Methyl Methacrylate is an unsaturated ester that has several uses in polymer manufacturing.
Methyl Methacrylate is a clear liquid with a characteristic ester odor.
There are several synthetic routes to Methyl Methacrylate.
The most widely used are a three-step sequence that begins with acetone and HCN and proceeds through acetone cyanohydrin; and a two-step process that begins with the reaction of ethylene and methanol to produce methyl propionate.
By far the greatest volume of Methyl Methacrylate is polymerized to the homopolymer poly(methyl methacrylate) (PMMA).
The polymer is a clear plastic that is known by the familiar trade names Lucite and Plexiglas.
Methyl Methacrylate is also copolymerized with styrene and butadiene to make an additive to poly(vinyl chloride) (PVC) that improves its properties.
Methyl Methacrylate is also transesterified to make specialty methacrylate monomers.
Methyl Methacrylate is a monomer that’s also known as methacrylic acid, methyl ester.
A key building block for acrylic-based polymers, Methyl Methacrylate has applications that include safety glazing, exterior paints, vinyl impact modifiers, adhesives, illuminated light displays, and more.
There are several synthetic ways to make the Methyl Methacrylate chemical as the one most widely used is the three-step process of adding acetone to hydrogen cyanide (HCN) and moves to acetone cyanohydrin.
Applications of Methyl Methacrylate: Manufacturing of plates, rods, and pipe, Molding material, Paint, Dental material, Adhesive, Fiber processing agent, and Leather treatment.
WHAT IS METHYL METHACRYLATE USED FOR?
The uses of Methyl Methacrylate include:
*PMMA Production:
Methyl Methacrylate is used for the production of PMMA, also known as acrylic or acrylic glass.
PMMA is used in a variety of applications, including: transparent windows, skylights, aircraft canopies, and outdoor signage due to its excellent clarity and weather resistance.
*Surface Coatings:
Methyl Methacrylate is used in the formulation of various paints and coatings that require quick drying times, durability, and UV resistance.
These coatings are applied to automotive parts, marine vessels, and flooring.
*Adhesives and Sealants:
Methyl Methacrylate is a key component in the manufacturing of adhesives and sealants used in the construction and automotive industries.
*Dental and Medical Applications:
Methyl Methacrylate iss used in the medical field for manufacturing dental prostheses and bone cement.
Its biocompatibility and quick-curing properties make Methyl Methacrylate suitable for these sensitive applications.
*Electronic Devices:
Methyl Methacrylate's electrical insulating properties make it useful in the production of electronic components, such as LED screens and light guide panels.
HOW IS METHYL METHACRYLATE MADE?
Methyl Methacrylate is predominantly produced through the acetone cyanohydrin (ACH) process, which starts with reacting acetone with hydrogen cyanide (HCN) in the presence of a basic catalyst to form acetone cyanohydrin.
Methyl Methacrylate is then converted to methacrylamide sulfate through a reaction with sulfuric acid, followed by methacrylamide's reaction with methanol, yielding MMA and ammonium sulfate byproduct.
Another method, the ethylene method, involves oxidizing ethylene to produce acetic acid, which is then reacted with formaldehyde and hydrocyanic acid to form ethylene cyanohydrin.
This is catalytically converted into MMA.
Additionally, the C3/C4 oxidation process represents a newer approach, in which isobutene or tert-butanol is oxidized to methacrylic acid, which is subsequently esterified with methanol to produce MMA.
The “BASF process” is another way to produce Methyl Methacrylate, which involves four steps, beginning with the conversion of ethylene into propionaldehyde (PA) via the hydroformylation process.
Following this, PA undergoes a reaction with formaldehyde, resulting in the creation of methacrolein (MA).
The next phase involves the oxidation of MA into methacrylic acid (MAA).
The final step in this sequence is the esterification of MAA, which leads to the production of Methyl Methacrylate.
There's also a method involving the direct esterification of methacrylic acid with methanol.
The choice among these processes depends on factors like raw material availability, cost-effectiveness, and environmental considerations, each offering distinct advantages and challenges in the production of Methyl Methacrylate.
CHEMICAL PROPERTIES OF METHYL METHACRYLATE:
Methyl methacrylate is a flammable liquid.
Methyl Methacrylate is slightly soluble in water and is soluble in some organic solvents.
Methyl Methacrylate (MMA) is an ester of Methacrylic Acid and is used as a raw material in the synthesis of polymers.
Methyl Methacrylate is a monofunctional monomer containing a characteristic highly reactive Methacrylate group and a cyclic hydrophobic group.
Methyl Methacrylate can form homopolymers and copolymers with (meth)acrylic acids and salts, amides, esters, (meth)acrylates, acrylonitrile, maleic acid esters, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene, and other monomers.
PROPERTIES OF METHYL METHACRYLATE:
*Hydrophobicity
*Hardness
*Adhesion
*Weather resistance
APPLICATION AREAS OF METHYL METHACRYLATE:
Methyl Methacrylate is used in the production of organic glass, coatings, lubricant additives, plastics, adhesives, wood impregnating agents, electrical coil impregnation, ion exchange resins, paper glossing agents, textile auxiliaries, leather processing materials, paint additives, and insulation filling materials.
IT IS APPLIED IN THE PRODUCTION OF METHYL METHACRYLATE
*Acrylic resins
*Coating resins
*Molding materials
*Latex paints
*Adhesives and sealants
*Emulsions
*Modifiers
*Impregnation agents
BENEFITS OF METHYL METHACRYLATE
*Impact strength
*Weather resistance
*Crosslinking sites, ester group reacts readily with isocyanate, anhydrides and epoxy resins
*Corrosion, fogging, and abrasion resistance, as well as contribute to low odor, color, and volatility
WHAT ARE THE CHEMICAL PROPERTIES OF METHYL METHACRYLATE?
The main chemical properties of Methyl Methacrylate include:
Methyl Methacrylate has the molecular formula C5H8O2, featuring a methacrylate group with a double bond between the carbon atoms, making it highly reactive and suitable for polymerization.
At room temperature, Methyl Methacrylate is a colorless, clear liquid with a characteristic, sharp, fruity odor.
Methyl Methacrylate has a boiling point of around 100–101 °C and a freezing point of about -48 °C, indicating its volatility and the care needed in its storage and handling.
Methyl Methacrylate is soluble in most organic solvents, such as: ethanol, acetone, and benzene, but it is only slightly soluble in water.
The double bond in the methacrylate group is highly reactive, which makes Methyl Methacrylate a monomer that readily forms polymers and copolymers.
Methyl Methacrylate has moderate thermal stability.
Methyl Methacrylate is considered a volatile organic compound (VOC) with potential health risks, necessitating proper safety measures during handling and use.
Methyl Methacrylate vapor can irritate the eyes, skin, and respiratory system.
WHAT IS THE COMMON NAME FOR METHYL METHACRYLATE?
The common name for methyl methacrylate, or MMA, is the same as its chemical name, "methyl methacrylate."
This monomer also goes by the name methacrylic acid methyl ester.
However, MMA is best known as the main ingredient in the production of polymethyl methacrylate (PMMA) acrylic plastics, which are often referred to by brand names such as Plexiglas, Lucite, and Perspex.
WHAT ARE THE ADVANTAGES OF METHYL METHACRYLATE?
Methyl Methacrylate offers several advantages that make it a valuable material in various industrial and commercial applications:
Methyl Methacrylate can be easily polymerized into polymethyl methacrylate (PMMA) and other copolymers, allowing for a wide range of applications, from transparent plastics and coatings to adhesives and sealants.
The polymers formed from Methyl Methacrylate, such as PMMA, are known for their excellent optical clarity and light transmission, comparable to glass but with greater impact resistance and less weight.
Methyl Methacrylate-based products like PMMA are durable, resistant to UV light, and maintain their properties over a wide range of temperatures.
Polymers derived from Methyl Methacrylate exhibit good resistance to many chemicals, making them useful in environments in which corrosion could be an issue, such as in chemical-processing equipment and medical devices.
Methyl Methacrylate is used in medical and dental applications because the materials derived from it are biocompatible, making them suitable for contact with body tissues and fluids in implants and dental prostheses.
Methyl Methacrylate and its polymers can be easily processed and formed into various shapes, allowing for the production of complex components and designs in industries ranging from automotive to fashion.
Compared to glass and some other plastics, PMMA offers a lightweight option without compromising on strength or clarity.
Is recyclable, which is important in today’s environmentally conscious market.
This allows for the sustainable use of materials and reduces waste.
HISTORY OF METHYL METHACRYLATE:
The history of the formulation of methyl methacrylate monomer began during a time when acrylic acids were first being synthesized in the early 1800s.
German chemists took roughly 85 years to develop acrylic acid in 1843.
Then it took another 22 years for them to make methacrylic acid, and then from that step methanol was added to form the chemical reaction of methyl methacrylate, which would become known as acrylic polymer.
Yet still in that time, the possibilities of using methacrylic acid to make was still not readily understood.
It wasn't until roughly the 1930s when acrylic polymers appeared with the polymerization of metal acrylate.
We provide a general overview of this important monomer, covering everything from its polymerization to important safety and handling considerations.
THE BASICS OF METHYL METHACRYLATE:
As previously mentioned, Methyl Methacrylate is foundational for many acrylate polymers and is an essential comonomer in paint, coatings, and adhesives resin formulations.
A comonomer consists of one monomer that is added to another monomer to become a copolymer.
In free radical initiated copolymers, Methyl Methacrylate chemical structure elevates the Tg (glass transition) and contributes durability, strength, transparency, and UV and abrasion resistance.
SOLUBILITY OF METHYL METHACRYLATE:
Methyl Methacrylate is slightly miscible with water.
NOTES OF METHYL METHACRYLATE:
Methyl Methacrylate is incompatible with oxidizing agents, peroxides, amines, bases, acids, reducing agents, and halogens.
SYNTHESIS OF METHYL METHACRYLATE
According to the previous work, Methyl methacrylate can be synthesized by the following steps: A solution of 375 g of aluminum nitrate nonahydrate, 256 g of magnesium nitrate hexahydrate and 54 g of 60% nitric acid in 500 mL water were added dropwise at 15 °C to 2 kg of silica sol solution with 10-20 nm particle size (Nissan Chemical Industries, Snowdex N-30, 30 wt% SiO2).
The mixture was stirred for 24 hours at 50 °C, cooled to room temperature, spray-dried (130 °C) and calcined (300-600 °C, a total of 10 hours).
30 g of the SiO2-Al2O3-carrier was suspended in 100 mL of water and heated at 90 °C.
This suspension was added in 15 min at 90 °C to a solution of 1.64 g of nickel nitrate hexahydrate and 530 mg acid (HAuCl4) in 100 mL of water.
After another 30 min of stirring at 90 °C, cooled and the solid was separated, then stirred three times with 100 mL of fresh water for 5 minutes each at 20 °C and filtered.
The catalyst was dried at 105 °C within 10 hours and calcined at 450 °C for 5 hours in air.
The violet powder obtained by ICP analysis contained 1.1% Ni and 0.9% Au.
The average particle size of gold nanoparticles (TEM) was less than 5 nm.
A mixture of 0.67 g of methacrolein (from Example 1), 5.65 g of methanol and 504 mg Au catalyst 1 were stirred in an autoclave under 11 bar of O2/N2 gas mixture (7 Vol-% O2) at 80 °C over 2 hours, then cooled, filtered and analyzed by GC.
Space-time yield 9.3 Methyl Methacrylate mol/kg cat-hr.
Conversion of MAL was 98.4%, Yield at Methyl methacrylate 94.8%.
WHERE IS METHYL METHACRYLATE FOUND?
Methyl methacrylate is used in the manufacture of plastics with an acrylic resin base.
Methyl Methacrylate may be used in the automotive industry coatings and sealants, in leather, paper and textile surface treatments, in acrylate adhesives, and in latex paints, lacquers, and enamel resins.
Methyl Methacrylate is also used in healthcare as bone cement, and in dental materials such as crowns, veneers and fillings.
Methyl Methacrylate is also used in artificial fingernail adhesive.
THE POLYMERIZATION OF METHYL METHACRYLATE:
Polymerization involves bonding smaller monomers so that they become a polymer.
When it comes to polymerization, the range of acrylic copolymers that can be used with Methyl Methacrylateis extensive.
Monomer feeds can include:
*Butyl acrylate
*2-Ethylhexyl acrylate
*Methyl methacrylate and other methacrylate esters
*Acrylic acid and methacrylic acid
*Styrene
*Butadiene
The monomer composition selected for copolymers is driven by the desired Tg of the resin, ranging from -30˚C to > 30˚C.
The free-radical reactivity ratios for Methyl Methacrylate copolymer systems have been well studied and are available in the literature.
THE COMPOSITION OF A METHYL METHACRYLATE:
To provide an example of a methyl methacrylate application, a typical paint formulation using MMA monomer in a copolymer is used in coatings and paints to enhance durability, clarity, and adhesion.
IS METHYL METHACRYLATE A PLASTIC?
No.
Methyl Methacrylate itself is not a plastic; it is a monomeric liquid compound that serves as a building block for making plastics.
When Methyl Methacrylate undergoes polymerization, it forms polymethyl methacrylate (PMMA), which is a type of plastic known for its clear, glass-like appearance and excellent durability, weatherability, and resistance to UV light.
So, while Methyl Methacrylate is the precursor to a widely used plastic, it is not a plastic in its monomeric form.
TYPES OF METHYL METHACRYLATE:
Methyl Methacrylate serves as a foundation for a wide array of products across various industries.
Listed below are the different types of Methyl Methacrylate-based products:
*Methyl Methacrylate Adhesives
These are high-performance adhesives known for their strong bonding capabilities, rapid curing times, and durability.
Methyl Methacrylate adhesives are widely used in the automotive, construction, and marine industries for joining materials that are difficult to bond, such as: metals, plastics, and composites.
*Polymerized Methyl Methacrylate
This is the polymer form of Methyl Methacrylate, commonly known as acrylic or acrylic glass (with trade names like: Plexiglas, Lucite, and Perspex).
PMMA’s characteristic traits are its clarity, strength, and resistance to UV light and weathering.
This is why it is so suitable for use in windows, lenses, and as a glass substitute in various applications.
*Monomeric Methyl Methacrylate
In its monomeric form, Methyl Methacrylate is a clear, colorless liquid used as a building block for polymerization into PMMA and other copolymers.
It’s also utilized as a solvent and an intermediate in organic synthesis.
*Dental-grade Methyl Methacrylate
Specifically formulated for dental applications, dental-grade methyl methacrylate is used in the production of dental prostheses and as a component in dental cement.
Its biocompatibility and ease of polymerization make it ideal for these purposes.
*Methyl Methacrylate Resins
Methyl Methacrylate resins find applications in coatings, inks, and adhesives, providing excellent hardness, flexibility, and resistance to abrasion and chemicals.
They are often used in automotive finishes and industrial coatings.
*Methyl Methacrylate-based Copolymers
Methyl Methacrylate is copolymerized with other monomers to produce materials with tailored properties for specific uses.
These copolymers can offer improved impact resistance, flexibility, or compatibility with other materials, expanding the range of applications for Methyl Methacrylate-derived products.
*Modified Methyl Methacrylate Polymers
These are PMMA polymers that have been chemically modified to enhance certain properties, such as impact resistance or elasticity.
Modified Methyl Methacrylate polymers are used in applications in which standard PMMA's properties need to be fine-tuned for specific performance requirements.
HOW DOES POLYMERIZATION AFFECT METHYL METHACRYLATE'S MAIN INDUSTRIAL USES?
Polymerization significantly enhances the industrial utility of Methyl Methacrylate by transforming it from a monomeric liquid into polymers and copolymers with diverse and valuable properties.
Through polymerization, Methyl Methacrylate becomes the foundation for producing PMMA, a clear, durable plastic known for its excellent optical clarity, resistance to UV light, and weatherability.
This transformation allows Methyl Methacrylate to be used in a wide range of applications, including the manufacture of shatterproof glass substitutes, lenses, and various optical devices.
Furthermore, the ability of Methyl Methacrylate to copolymerize with other monomers expands its applications into sectors such as: coatings, adhesives, paints, and sealants, in which properties like: adhesion, hardness, and resistance to chemicals are critical.
The polymerization process, therefore, not only broadens the scope of Methyl Methacrylate’s applications but also significantly contributes to the material's performance in its various end uses, making it a key material in industries ranging from construction and automotive to healthcare and electronics.
IS METHYL METHACRYLATE ESSENTIAL IN CREATING POLYMETHYL METHACRYLATE?
Yes, Methyl Methacrylate is essential in creating polymethyl methacrylate, or PMMA.
Methyl Methacrylate is the monomer that undergoes polymerization to form PMMA.
This process involves the linking of numerous Methyl Methacrylate molecules together in chains through a reaction catalyzed by heat, light, or chemical initiators.
The resulting PMMA, also commonly known as acrylic, acrylic glass, Plexiglas, Lucite, or Perspex, is widely used in applications ranging from optical lenses and aquariums to aircraft windows and skylights.
OTHER ROUTES TO METHYL METHACRYLATE
*Via propionaldehyde
Ethylene is first hydroformylated to give propanal, which is then condensed with formaldehyde to produce methacrolein.
The condensation is catalyzed by a secondary amine.
Air oxidation of methacrolein to methacrylic acid completes the synthesis of the acid:
CH3CH2CHO + HCHO → CH2=C(CH3)CHO + H2O
CH2=C(CH3)CHO + ½ O2 → CH2=C(CH3)CO2H
*From isobutyric acid
As developed by Atochem and Röhm, isobutyric acid is produced by hydrocarboxylation of propene, using HF as a catalyst:
CH2=CHCH3 + CO + H2O → (CH3)2CHCO2H
Oxidative dehydrogenation of the isobutyric acid yields methacrylic acid.
Metal oxides catalyse this process:
(CH3)2CHCO2H + O → CH2=C(CH3)CO2H + H2O
*Methyl acetylene (propyne) process
Using Reppe chemistry, methyl acetylene is converted to MMA.
As developed by Shell, this process produces Methyl Methacrylate in one step reaction with 99% yield with a catalyst derived from palladium acetate, phosphine ligands, and Bronsted acids as catalyst:
CH≡CCH3 + CO + CH3OH → CH2=C(CH3)CO2CH3
*Isobutylene routes
The reactions by the direct oxidation method consist of two-step oxidation of isobutylene or TBA with air to produce methacrylic acid and esterification by methanol to produce Methyl Methacrylate:
CH2=C(CH3)2 or (CH3)3C−OH + O2 → CH2=C(CH3)−CHO + H2O
CH2=C(CH3)CHO + ½ O2 → CH2=C(CH3)CO2H
CH2=C(CH3)CO2H + CH3OH → CH2=C(CH3)CO2CH3 + H2O
A process using isobutylene as a raw material has been commercialized by Escambia Co.
Isobutylene is oxidized to provide α-hydroxy isobutyric acid.
The conversion uses N2O4 and nitric acid at 5–10 °C in the liquid phase.
After esterification and dehydration Methyl Methacrylate is obtained.
Challenges with this route, aside from yield, involve the handling of large amounts of nitric acid and NOx.
This method was discontinued in 1965 after an explosion at an operation plant.
*Methacrylonitrile (MAN) process
MAN can be produced by ammoxidation from isobutylene:
(CH3)2C=CH2 + NH3 + 3/2 O2 → CH2=C(CH3)CN + 3 H2O
This step is analogous to the industrial route to acrylonitrile, a related commodity chemical.
MAN can be hydrated by sulfuric acid to methacrylamide:
CH2=C(CH3)CN + H2SO4 + H2O → CH2=C(CH3)−CONH2·H2SO4
CH2=C(CH3)−CONH2·H2SO4 + CH3OH → CH2=C(CH3)COOCH3 + NH4HSO4
Mitsubishi Gas Chemicals proposed that MAN can be hydrated to methacrylamide without using sulfuric acid and is then esterified to obtain Methyl Methacrylate by methylformate:
CH2=C(CH3)CN + H2O → CH2=C(CH3)−CONH2
CH2=C(CH3)−CONH2 + HCOOCH3 → CH2=C(CH3)COOCH3 + HCONH2
HCONH2 → NH3 + CO
*Esterification of methacrolein
Asahi Chemical developed a process based on direct oxidative esterification of methacrolein, which does not produce by-products such as ammonium bisulfate.
The raw material is tert-butanol, as in the direct oxidation method.
In the first step, methacrolein is produced in the same way as in the direct oxidation process by gas phase catalytic oxidation, is simultaneously oxidized and is esterified in liquid methanol to get Methyl Methacrylate directly:
CH2=C(CH3)−CHO + CH3OH + ½ O2 → CH2=C(CH3)−COOCH3 + H2O
HISTORY OF METHYL METHACRYLATE:
Methyl Methacrylate was discovered by Bernhard Tollens and his student W. A. Caspary in 1873, who noticed and described its tendency to change into a clear, hard, transparent substance especially in sunlight.
Studies on acrylic esters slowly developed until the Staudinger's theory of macromolecules and his research into the nature of polyacrylates allowed control over polymerization.
Company Rohm and Haas, founded by German chemist Otto Röhm, who investigated the topic for three decades, was finally able to start its industrial production in 1931.
PRODUCTION AND PROPERTIES OF METHYL METHACRYLATE:
Given the scale of production, many methods have been developed starting from diverse two- to four-carbon precursors.
Two principal routes appear to be commonly practiced.
*CYANOHYDRIN ROUTE
The principal route begins with the condensation of acetone and hydrogen cyanide:
(CH3)2CO + HCN → (CH3)2C(OH)CN
Sulfuric acid then hydrolyzes acetone cyanohydrin (ACH) to a sulfate ester-adduct, which is cracked to the ester:
(CH3)2C(OH)CN + 2H2SO4 → ((CH3)2C(OSO3H)C(O)NH2·H2SO4 → (CH3)2C(OSO3H)C(O)NH2 + H2SO4
Methanolysis gives ammonium bisulfate and Methyl Methacrylate:
(CH3)2C(OSO3H)C(O)NH2 + CH3OH → CH2=C(CH3)C(O)OCH3 + NH4HSO4
Laboratory scale procedures are available for some of these steps.
This technology affords more than 3 billion kilograms per year, and the economics have been optimized.
Nevertheless, the ACH route coproduces substantial amounts of ammonium sulfate: roughly 1.1 kg/(kg Methyl Methacrylate).
The ammonium sulfate can be converted to diammonium sulfate, which is a common fertilizer.
Also Methyl Methacrylate can be combusted to give sulfuric acid.
METHYL PROPIONATE ROUTES
The first stage involves carboalkoxylation of ethylene to produce methyl propionate (MeP):
C2H4 + CO + CH3OH → CH3CH2CO2CH3
The MeP synthesis is conducted in a continuous-stirred tank reactor at moderate temperature and pressure using proprietary agitation and gas-liquid mixing arrangement.
In a second set of reactions, MeP is condensed with formaldehyde in a single heterogeneous reaction step to form Methyl Methacrylate:
CH3CH2CO2CH3 + CH2O → CH3(CH2)CCO2CH3 + H2O
The reaction of MeP and formaldehyde takes place over a fixed bed of catalyst.
This catalyst, caesium oxide on silica, achieves good selectivity to Methyl Methacrylate from MeP.
The formation of a small amount of heavy, relatively involatile compounds poisons the catalyst.
The coke is easily removed and catalyst activity and selectivity restored by controlled, in-situ regeneration.
The reactor product stream is separated in a primary distillation so that a crude Methyl Methacrylate product stream, free from water, MeP and formaldehyde, is produced.
Unreacted MeP and water are recycled via the formaldehyde dehydration process.
Methyl Methacrylate (>99.9%) is purified by vacuum distillations.
The separated streams are returned to the process; there being only a small heavy ester purge stream, which is disposed of in a thermal oxidizer with heat recovered for use in the process.
In 2008, Lucite International commissioned an Alpha Methyl Methacrylate plant on Jurong Island in Singapore.
This process plant was cheaper to build and run than conventional systems, produces virtually no waste and the feedstocks can even be made from biomass.
PHYSICAL and CHEMICAL PROPERTIES of METHYL METHACRYLATE:
Molecular Weight: 100.12 g/mol
XLogP3: 1.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 2
Exact Mass: 100.052429494 Da
Monoisotopic Mass: 100.052429494 Da
Topological Polar Surface Area: 26.3 Ų
Heavy Atom Count: 7
Formal Charge: 0
Complexity: 94.3
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Chemical Formula: C5H8O2
Molar Mass: 100.117 g·mol−1
Appearance: Colorless liquid
Odor: Acrid, fruity
Density: 0.94 g/cm³
Melting Point: −48 °C (−54 °F; 225 K)
Boiling Point: 100 °C (214 °F; 374 K)
Solubility in Water: 1.5 g/100 mL
log P: 1.35
Vapor Pressure: 29 mmHg (20 °C)
Magnetic Susceptibility (χ): −57.3·10−6 cm³/mol
Viscosity: 0.6 cP at 20 °C
Dipole Moment: 1.6–1.97 D
CAS Number: 80-62-6
EC Number: 201-297-1
Density: 0.940
Slightly Soluble: in water
Color, APHA: 10 Max
Water Content: 0.1% Max
Methacrylic Acid: 0.005% Max
Inhibitor (MEHQ): 8–15 ppm
Specific Gravity: 0.942–0.946
Refractive Index: 1.4110
Assay: 99.8% Min
Formula Weight: 100.12
Freezing Point: -48 °C
Specific Heat: 1.89 J/(g·°C)
Viscosity at 20°C: 0.56 mPa.s
Vapor Pressure: 40 mmHg (25.5 °C)
Odor: Sharp fruity odor
Color: Colorless volatile liquid
Molecular Weight: 100.1 g/mol
Flash Point: 8–13 °C
Solubility: MEK, THF, esters, aromatic and chlorinated hydrocarbons
Boiling Point: 99–100 °C
Vapour Density: 3.45
Specific Gravity: 0.943
Physical Description: Colorless liquid with an acrid, fruity odor
Boiling Point: 214 °F
Freezing Point/Melting Point: -54 °F
Vapor Pressure: 29 mmHg
Flash Point: 50 °F (open cup)
Vapor Density: 3.45
Specific Gravity: 0.94
Ionization Potential: 9.70 eV
Lower Explosive Limit (LEL): 1.7%
Upper Explosive Limit (UEL): 8.2%
NFPA Health Rating: 2
NFPA Fire Rating: 3
NFPA Reactivity Rating: 2
Physical State: Liquid
Color: Colorless
Odor: Pungent
Melting Point/Freezing Point: -48 °C - lit.
Initial Boiling Point and Boiling Range: 100.36 °C at ca. 1.01325 hPa
Flammability (Solid, Gas): No data available
Upper/Lower Flammability
Explosive Limits: Upper 12.5 % (V), Lower 2.1 % (V)
Flash Point: 10 °C - closed cup - DIN 51755 Part 1
Autoignition Temperature: 435 °C at 1.01325 hPa
Decomposition Temperature: No data available
pH: No data available
Viscosity, Kinematic: 0.56 mm²/s at 20 °C
Viscosity, Dynamic: 0.53 mPa.s at 20 °C
Water Solubility: 15.3 g/L at 20 °C
Partition Coefficient (n-octanol/water): log Pow 1.38 at 20 °C
Bioaccumulation: Not expected
Vapor Pressure: 37 hPa at 20 °C
Density: 0.936 g/cm³ at 25 °C
Relative Density: 0.94 at 20 °C
Relative Vapor Density: ca. 3.5 at 20 °C
Particle Characteristics: No data available
Explosive Properties: No data available
Oxidizing Properties: None
Other Safety Information: Surface tension 61 mN/m - OECD Test Guideline 115
Relative Vapor Density: ca. 3.5 at 20 °C
FIRST AID MEASURES of METHYL METHACRYLATE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of METHYL METHACRYLATE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of METHYL METHACRYLATE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of METHYL METHACRYLATE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of METHYL METHACRYLATE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of METHYL METHACRYLATE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available