Methyl Methacrylate

HCID 6658CAS 80-62-6

Basic information

Standard SMILES
C=C(C)C(=O)OC
InChIKey
VVQNEPGJFQJSBK-UHFFFAOYSA-N
Molecular formula
C5H8O2
Average molar mass
100.12 g/mol
Monoisotopic mass
100.05242949

Names & identifiers

Preferred name
Methyl Methacrylate
IUPAC
methyl 2-methylprop-2-enoate
English name
Methyl methacrylate
Molecular formula
C5H8O2
Molecular weight
100.12

Names & synonyms

METHYL METHACRYLATE80-62-6methyl 2-methylprop-2-enoateMethylmethacrylatePegalanMethacrylic acid methyl esterMethyl methylacrylateMethyl 2-methylpropenoateAcryester MDiakonMethyl-methacrylatMethyl 2-methyl-2-propenoate
Show more names
MMAMmeMethylmetacrylateMETHYL METACRYLAT
2-Propenoic acid, 2-methyl-, methyl esterMetakrylan metyluMetil metacrilatoMethylmethacrylaat2-(Methoxycarbonyl)-1-propene2-Methyl-2-propenoic acid methyl esterMethacrylate de methyleMethyl 2-methylacrylate

Database identifiers

CAS
80-62-6
PubChem CID
6658
DTXSID
DTXSID2020844
ChEMBL
CHEMBL49996
ChEBI
CHEBI:34840
UNII
196OC77688
EC Number
201-297-1
Nikkaji
J3.532G

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
7

Physicochemical properties

Melting point
-48 °C · -48 °C (lit.)
Boiling point
100 °C · 100 °C (lit.)
Density
0.936 g/mL · 0.936 g/mL at 25 °C (lit.)
vapor density
3.5 · 3.5 (vs air)
vapor pressure
29 mm · 29 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.414(lit.)

Safety & regulation

Safety data

OEB
A
OEL
TWA: 100 ppm (410 mg/m3)
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
IDLA
1,000 ppm
tsca
TSCA listed

Chemistry & industry

Applications · 5 items

DescriptionMethyl methacrylate is an organic compound with the formula CH2=C(CH3)COOCH3. This colourless liquid, the methyl ester of methacrylic acid (MAA) is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).

UsesMethyl methacrylatec is used in acrylic bone cements used in orthopedic surgery; in the production of acrylic polymers, polymethylmethacrylate and copolymers used in acrylic surface coatings; in the manufaeture of emulsion polymers; in the modification of unsaturated polyester resins; in the production of higher methacrylate, acrylic fibers, acrylic film, inks, radiation-polymerized impregnants for wood, and solvent-based adhesives and binders; as an impact modifier of PVC; in medicinal spray adhesives; in nonirritant bandage solvents; in dental technology as ceramic filler or cement; to coat corneal contact lenses; in intraocular lenses, artificial nails, and hearing aids; as a monomer for polymethaerylate resins; in the impregnation of concretc.

UsesMethyl methacrylate is a volatile synthetic chemical that is used principally in the production of cast acrylic sheet, acrylic emulsions, and moulding and extrusion resins. In the manufacture of methacrylate resins and plastics. Methyl methacrylate is transesterified into higher methacrylates such as n-butyl methacrylate or 2-ethylhexyl methacrylate. methyl methacrylate monomer is used in the production of methylmethacrylate polymers and copolymers, polymers and copolymers are also used in waterborne, solvent, and undissolved surface coatings, adhesives, sealants, leather and paper coatings, inks, floor polishes, textile finishes, dental prostheses, surgical bone cements, and leaded acrylic radiation shields and in the preparation of synthetic fingernails and orthotic shoe inserts. Methyl methacrylate is also used as a starting material to manufacture other esters of methacrylic acid. Granules for injection and extrusion blow moulding which for their outstanding optical clarity, weathering and scratch resistance are used in lighting, office equipment and electronics (cell phone displays and hi-fi equipment), building and construction (glazing and window frames), contemporary design (furniture, jewellery and tableware), cars and transportation (lights and instrument panels), health and safety (jars and test tubes) and household appliances (microwave oven doors and mixer bowls). Impact modifiers for clear rigid polyvinyl chloride.

UsesThe principal application, consuming approximately 80% of the MMA, is the manufacture of poly methyl 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 is as cement used in total hip replacements as well as total knee replacements. 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 methyl methacrylate 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. Also used in fracture repair in small exotic animal species using internal fixation.

General DescriptionA clear colorless liquid. Slightly soluble in water and floats on water. Vapors heavier than air. Vapors irritate the eyes and respiratory system. Containers must be heavily insulated or shipped under refrigeration. An inhibitor such as hydroquinone, hydroquinone methyl ester and dimethyl t-butylphenol is added to keep the chemical from initiating polymerization. The chemical 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. Used to make plastics.

Preparation methods

PreparationPrepared by the esterification of methacrylamide sulfate with methanol.

Additional notes · 1 item

DefinitionChEBI: Methyl methacrylate is an enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component. It has a role as an allergen and a polymerisation monomer. It is an enoate ester and a methyl ester. It is functionally related to a methacrylic acid.

Related reactions

586 records

Linked notes

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