Methyl methacrylate

Base Information

• Chemical Name: Methyl methacrylate
• CAS No.: 80-62-6
• Deprecated CAS: 162221-54-7,220713-32-6,874217-13-7,1196968-39-4,1227277-87-3,1451188-71-8,1453489-95-6,211862-43-0,1196968-39-4,1227277-87-3,220713-32-6,874217-13-7
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 29161410
• European Community (EC) Number: 201-297-1,618-466-4,924-135-8,686-139-3
• ICSC Number: 0300
• NSC Number: 4769
• UN Number: 1247
• UNII: 196OC77688
• DSSTox Substance ID: DTXSID2020844
• Nikkaji Number: J3.532G
• Wikipedia: Poly(methyl_methacrylate),Methyl_methacrylate
• Wikidata: Q382897
• NCI Thesaurus Code: C47615
• RXCUI: 29897
• Metabolomics Workbench ID: 45475
• ChEMBL ID: CHEMBL49996
• Mol file: 80-62-6.mol

Synonyms:METHYL METHACRYLATE;80-62-6;methyl 2-methylprop-2-enoate;Methylmethacrylate;Methyl methylacrylate;Methyl 2-methylpropenoate;Methacrylic acid methyl ester;Pegalan;Methyl-methacrylat;Methyl 2-methyl-2-propenoate;Diakon;Acryester M;2-Propenoic acid, 2-methyl-, methyl ester;Methacrylate de methyle;Methyl 2-methylacrylate;Cranioplast;Metaplex;2-Methyl-2-propenoic acid methyl ester;Methacrylsaeuremethyl ester;2-(Methoxycarbonyl)-1-propene;Kallocryl A;Metakrylan metylu;Methylmethacrylaat;Metil metacrilato;Simplex P;Rcra waste number U162;Methyl alpha-methylacrylate;Methyl methacrylate monomer;TEB 3K;NCI-C50680;2-Methylacrylic acid, methyl ester;Methacrylic acid, methyl ester;9011-14-7;Acrylic acid, 2-methyl-, methyl ester;Methylmethacrylaat [Dutch];2-Methyl-acrylic acid methyl ester;Metakrylan metylu [Polish];NSC 4769;Methyl-methacrylat [German];Metil metacrilato [Italian];Monocite methacrylate monomer;CCRIS 1364;HSDB 195;Methylester kyseliny methakrylove;CHEBI:34840;Methacrylate de methyle [French];2-methylacrylic acid methyl ester;Methyl meth-d3-acrylate;Methacrylsaeuremethyl ester [German];EINECS 201-297-1;UN1247;RCRA waste no. U162;BRN 0605459;Methylester kyseliny methakrylove [Czech];Methyl .alpha.-methylacrylate;monocite" Methacrylate monomer;AI3-24946;DTXSID2020844;UNII-196OC77688;NSC-4769;Methyl methacrylate monomer, inhibited;143476-91-9;Methyl ester of 2-methyl-2-propenoic acid;196OC77688;EC 201-297-1;114512-63-9;4-02-00-01519 (Beilstein Handbook Reference);51391-19-6;Plexiglass;Kallocryl;Sintex;Zimmer Bone Cement;55063-97-3;Methacrylate Methyl Monomer;Metylmetakrylat;Eudragit;Methylmethacrylate Methyl Monomer;methoxymethacrolein;MMA (stabilized);J69;Methacrylate monomer;Methacrylate, methyl-;MMM (CHRIS Code);2-Propenoic acid, 2-methyl- methyl ester;Acrylic resins (PMMA);METHYL METHACTRYLATE;Epitope ID:131321;Methyl 2-methylacrylate #;Methyl methacrylate (MMA);Methyl-.alpha.-methacrylate;SCHEMBL1849;CH2=C(CH3)COOCH3;Methacrylic acid-methyl ester;methyl-2-methyl-2-propenoate;NA 1247 (Salt/Mix);UN 1247 (Salt/Mix);BIDD:ER0634;CHEMBL49996;DTXCID80844;Methyl methacrylate, 99.5%;WLN: 1UY1&VO1;Methyl methacrylate, stabilized;Methyl ester of methacrylic acid;Methyl methacrylate, CP,98.0%;NSC4769;METHYL METHACRYLATE [HSDB];METHYL METHACRYLATE [IARC];METHYL METHACRYLATE [INCI];METHYLMETHACRYLATE [MART.];METHYL METHACRYLATE [VANDF];METHYLMETHACRYLATE [WHO-DD];Tox21_200367;MFCD00008587;NA1247;STL283952;AKOS000120216;Methyl methacrylate, 99%, stabilized;LS-1799;CAS-80-62-6;NCGC00091089-01;NCGC00091089-02;NCGC00257921-01;9065-11-6;Methacrylic Acid Methyl Ester (stabilized;METHACRYLIC ACID METHYL ESTER [MI];M0087;METHYL 2-METHYL-2-PROPENOATE [FHFI];EN300-19210;C19504;Methyl methacrylate 1000 microg/mL in Methanol;Methyl methacrylate, SAJ first grade, >=99.0%;A839957;Q382897;J-522614;F0001-2087;Methacrylic acid-methyl ester 100 microg/mL in Cyclohexane;Methyl Methacrylate (stabilized with 6-tert-Butyl-2,4-xylenol);Methyl methacrylate monomer, inhibited [UN1247] [Flammable liquid];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);80209-57-0;97555-82-3

Chemical Property of Methyl methacrylate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 29 mm Hg ( 20 °C)
• Melting Point: -48 °C
• Refractive Index: n20/D 1.414(lit.)
• Boiling Point: 100.3 °C at 760 mmHg
• Flash Point: 10 °C
• PSA: 26.30000
• Density: 0.914 g/cm³
• LogP: 0.73550
• Storage Temp.: Refrigerator
• Solubility.: 15g/l
• Water Solubility.: 15.9 g/L (20 ºC)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 94.3
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

MME ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi,T
• Hazard Codes: F,Xi,T
• Statements: 11-37/38-43-39/23/24/25-23/24/25
• Safety Statements: 24-37-46-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> (Meth)acrylates
• Canonical SMILES: CC(=C)C(=O)OC
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the peripheral nervous system.
• Description: Methyl 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).
• Physical properties: Clear, colorless liquid with a penetrating, fruity odor. An experimentally determined odor threshold concentration of 210 ppbv was reported by Leonardos et al. (1969). Experimentally determined detection and recognition odor threshold concentrations were 200 μg/m3 (49 ppbv) and 1.4 mg/m3 (340 ppbv), respectively (Hellman and Small, 1974).
• Uses: Methyl 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. The 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. Methyl 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.

Technology Process of Methyl methacrylate

There total 180 articles about Methyl methacrylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

poly(methacrylic acid) (79-41-4,25087-26-7,50867-57-7) + methyl salicylate (119-36-8,8024-54-2) → methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7) + salicylic acid (69-72-7,25496-36-0,8052-31-1)

Guidance literature:

poly(methacrylic acid); With potassium carbonate; In N,N-dimethyl acetamide; at 110 ℃; for 0.5h;

methyl salicylate; at 110 ℃; for 24h;

DOI:10.1055/s-0033-1340285

Reference yield: 48.7%

cellulose (9004-34-6) → methyl lactate (547-64-8,2155-30-8) + methyl 2-hydroxybutyrate (29674-47-3) + methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7)

Guidance literature:

With ortho-tungstic acid; In methanol; for 2h; Solvent; Reagent/catalyst; Autoclave;

Reference yield: 48.7%

cellulose (9004-34-6) → methyl lactate (547-64-8,2155-30-8) + levulinic acid methyl ester (624-45-3) + methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7)

Guidance literature:

With ortho-tungstic acid; In ethanol; for 2h; Time; Autoclave;

upstream raw materials:

quinoline

methyl 3-chloro-2-methylpropionate

hydroquinone

methyl 2-chloroisobutyrate

Downstream raw materials:

(2-methyl-3-morpholin-4-yl)propionic acid methyl ester

2-N-morpholinoethyl methacrylate

furan-2-ylmethyl methacrylate

2-methyl-N-p-tolylacrylamide

Refernces

• 1、 Li, Xiaopei,Kato, Tatsuhisa,Nakamura, Yasuyuki,Yamago, Shigeru. "The effect of viscosity on the coupling and hydrogen-abstraction reaction between transient and persistent radicals". . p. 966 - 972. Retrieved 2021/04/29.
• 2、 -. "Gold-based catalyst for oxidative esterification of aldehydes to carboxylic acid esters". Page/Page column 15. . Retrieved 2021/02/03.