Glycidyl methacrylate

Base Information

• Chemical Name: Glycidyl methacrylate
• CAS No.: 106-91-2
• Deprecated CAS: 117955-24-5,122785-80-2,126872-19-3,169957-95-3,201732-55-0,203300-26-9,210093-72-4,55279-88-4,89678-75-1,96778-02-8,98104-93-9,865699-83-8,202149-12-0,1451188-70-7,55279-89-5,329764-00-3,149212-20-4,345339-73-3,871813-55-7,1006609-21-7,1007600-88-5,1204187-60-9,1225228-65-8,1225228-67-0,79956-57-3,1415720-11-4,1982383-94-7,2100270-24-2,2127419-61-6,1978310-36-9,2442502-05-6,2609606-12-2,122785-80-2,126872-19-3,169957-95-3,201732-55-0,202149-12-0,203300-26-9,210093-72-4,865699-83-8,89678-75-1,96778-02-8,98104-93-9
• Molecular Formula: C7H10O3
• Molecular Weight: 142.155
• Hs Code.: 29161490
• European Community (EC) Number: 203-441-9,621-900-5
• ICSC Number: 1679
• NSC Number: 67195,24156
• UN Number: 2810
• UNII: R8WN29J8VF
• DSSTox Substance ID: DTXSID0025361
• Nikkaji Number: J38.145D
• Wikipedia: Glycidyl_methacrylate
• Wikidata: Q2013175
• Metabolomics Workbench ID: 123330
• ChEMBL ID: CHEMBL1333073
• Mol file: 106-91-2.mol

Synonyms:2-Propenoicacid, 2-methyl-, oxiranylmethyl ester (9CI);Methacrylic acid, 2,3-epoxypropylester (6CI,7CI,8CI);2,3-Epoxypropyl methacrylate;2-Methylacrylicacid oxiranylmethyl ester;2-[(Methacryloyloxy)methyl]oxirane;3-Methacryloyloxy-1,2-epoxypropane;Acryester G;Blemmer G;Blemmer GH-LC;Blemmer GMA;Blemmer GP;Blemmer GS;Epoxypropyl methacrylate;Glycidolmethacrylate;Glycidyl a-methylacrylate;Light Ester G;Methacryloyloxymethyloxirane;NSC 24156;NSC 67195;SR 379;SY-Monomer G;Sartomer 379;Sartomer SR 379;

Chemical Property of Glycidyl methacrylate

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 0.582mmHg at 25°C
• Melting Point: -52 °C
• Refractive Index: n20/D 1.449(lit.)
• Boiling Point: 188.999 °C at 760 mmHg
• Flash Point: 76.111 °C
• PSA: 38.83000
• Density: 1.042 g/cm³
• LogP: 0.50450
• Storage Temp.: Refrigerator
• Water Solubility.: 0.5-1.0 g/100 mL at 20 ºC
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 142.062994177
• Heavy Atom Count: 10
• Complexity: 162
• Transport DOT Label: Poison

Purity/Quality:

99% , ^*data from raw suppliers

Glycidyl methacrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T,T+
• Statements: 20/21/22-36/38-43-60-45-68-39/26-34
• Safety Statements: 26-28-28A-45-36/37-53-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Plastics & Rubber -> (Meth)acrylates
• Canonical SMILES: CC(=C)C(=O)OCC1CO1
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Uses: Glycidyl methacrylate (GMA) is a common monomer used in the creation of epoxy resins. It is used to provide epoxy functionalization to polyolefins and other acrylate resins. Glycidyl methacrylate is used in the production of polymer coatings and finishes, adhesives, plastics and elastomers. Glycidyl methacrylate dextran has been reported to be used as a biocompatible hydrogel. In situ polymerization of GMA with trimethylolpropane trimethacrylate to form macroporous sorbents has also been reported. GMA may also be grafted onto polypropylene. Glycidyl methacrylate is commonly used as a monomer for the preparation of epoxy resins. It is also used to provide epoxy functionalization to polyolefins and other acrylate resins. Further, it is also useful as an epoxy resin additive for paint coating formulations and adhesive applications. Glycidyl methacrylate dextran (GMA) has been reported to be used as a biocompatible hydrogel. In situ polymerization of GMA with trimethylolpropane trimethacrylate to form macroporous sorbents has also been reported. GMA may also be grafted onto polypropylene.

Technology Process of Glycidyl methacrylate

There total 21 articles about Glycidyl 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: 98.5%

→ 2,3-Epoxypropyl methacrylate (106-91-2,25067-05-4,98104-93-9)

Guidance literature:

Reference yield: 93.0%

oxiranyl-methanol (556-52-5) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 2,3-Epoxypropyl methacrylate (106-91-2,25067-05-4,98104-93-9)

Guidance literature:

With chlorine;

Reference yield: 90.0%

epoxychloropropane (66794-22-7) + poly(methacrylic acid) (79-41-4,25087-26-7,50867-57-7) → 2,3-Epoxypropyl methacrylate (106-91-2,25067-05-4,98104-93-9)

Guidance literature:

epoxychloropropane; With 10H-phenothiazine; sodium carbonate; In dichloromethane; at 70 ℃; for 1h; Large scale;

poly(methacrylic acid); With tetrabutyl ammonium fluoride; In dichloromethane; water; at 102 ℃; for 3.5h; Large scale;

upstream raw materials:

oxiranyl-methanol

Methacryloyl chloride

poly(methacrylic acid)

epichlorohydrin

Downstream raw materials:

3-dimethylamino-2-hydroxypropyl (meth)acrylate

2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

(2S)-2,3-dihydroxypropyl methacrylate

(S)-glycidyl methacrylate

Refernces

• 1、 Büttner, Hendrik,Kohrt, Christina,Wulf, Christoph,Sch?ffner, Benjamin,Groenke, Karsten,Hu, Yuya,Kruse, Daniela,Werner, Thomas. "Life Cycle Assessment for the Organocatalytic Synthesis of Glycerol Carbonate Methacrylate". . p. 2701 - 2707. Retrieved 2019.
• 2、 Donaire, Antonio,Garcia-Verdugo, Eduardo,Lozano, Pedro,Luis, Santiago V.,Nieto, Susana,Porcar, Raul,Villa, Rocio. "Sustainable chemo-enzymatic synthesis of glycerol carbonate (meth)acrylate from glycidol and carbon dioxide enabled by ionic liquid technologies". . p. 4191 - 4200. Retrieved 2021/06/17.
• 3、 Vanbiervliet, Elise,Fouquay, Stéphane,Michaud, Guillaume,Simon, Frédéric,Carpentier, Jean-Fran?ois,Guillaume, Sophie M.. "From epoxide to cyclodithiocarbonate Telechelic polycyclooctene through chain-transfer ring-opening metathesis polymerization (ROMP): Precursors to non-isocyanate polyurethanes (NIPUS)". . p. 69 - 82. Retrieved 2017/04/03.