106-91-2

Basic information

• Product Name: Glycidyl methacrylate
• Synonyms: Glycidyl Methacrylate Glycidyl Methacrylate, stabilized, 97% 100GR;Glycidyl Methacrylate, stabilized, 97% 500GR;2-Methyl-2-oxiranyl-2-propenoic acid Methyl ester;Glycidyl Methacrylat;GMA(glycidyl Methacrylate);Glycidyl Methacrylate OR Methacrylic acid 2,3-epoxypropyl ester;Glycidyl Methacrylate >=97.0% (GC)
• CAS NO: 106-91-2
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.15
• EINECS: 203-441-9
• Product Categories: Acrylic Monomers;Building Blocks;Chemical Synthesis;Epoxides;Materials Science;Methacrylate;Monomers;Organic Building Blocks;Oxygen Compounds;Polymer Science;Oxiranes;Simple 3-Membered Ring Compounds
• Mol File: 106-91-2.mol
• Article Data: 26

Chemical Properties

• Melting Point: -52°C
• Boiling Point: 189 °C(lit.)
• Flash Point: 169 °F
• Appearance: Clear/Liquid
• Density: 1.075 g/mL at 20 °C
• Vapor Pressure: 0.582mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: Refrigerator
• Water Solubility: 0.5-1.0 g/100 mL at 20 ºC
• Stability: Unstable. Light sensitive. May be stabilized with around 100ppm MEHQ. Refrigerate.
• BRN: 2506
• CAS DataBase Reference: Glycidyl methacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Glycidyl methacrylate(106-91-2)
• EPA Substance Registry System: Glycidyl methacrylate(106-91-2)

Safety Data

• 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
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 2
• RTECS: OZ4375000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 106-91-2(Hazardous Substances Data)

Usage

Uses

Used in Coatings and Adhesives Industry:
Glycidyl methacrylate is used as a monomer for the preparation of epoxy resins, providing epoxy functionalization to polyolefins and other acrylate resins. It is utilized in the production of polymer coatings and finishes, adhesives, plastics, and elastomers.
Used in Biocompatible Hydrogels:
Glycidyl methacrylate dextran has been reported to be used as a biocompatible hydrogel, offering potential applications in the medical and pharmaceutical fields.
Used in Sorbent Production:
In situ polymerization of GMA with trimethylolpropane trimethacrylate is employed to form macroporous sorbents, which can be used in various industrial and environmental applications for the absorption and separation of different substances.
Used in Polymer Modification:
GMA may be grafted onto polypropylene, enhancing its properties and expanding its range of applications in the plastics industry.

Preparation

Glycidyl methacrylate is produced from methacrylic acid and glycidol. Glycidol contain both epoxide and alcohol functional groups.It is an enoate ester and an epoxide. It derives from a methacrylic acid and a glycidol.

Reactions

Glycidyl methacrylate (GMA) is a kind of functional monomer. Its active vinyl and epoxy groups could be grafted with polyolefin and reacted with the polar groups such as amine, hydroxyl and carboxyl group, respectively. It can also undergo polymerization to form poly (glycidyl methacrylate).

Synthesis Reference(s)

Tetrahedron, 48, p. 5099, 1992 DOI: 10.1016/S0040-4020(01)90120-6Synthesis, p. 1019, 1986 DOI: 10.1055/s-1986-31856

Air & Water Reactions

Flammable. Slightly water soluble.

Reactivity Profile

Epoxides, such as Glycidyl methacrylate, are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Health Hazard

The liquid irritates eyes about as much as soap. Prolonged contact with skin produces irritation and dermatitis.

Fire Hazard

Special Hazards of Combustion Products: Irritating vapors are generated when heated

Flammability and Explosibility

Flammable

InChI:InChI=1/C7H10O3/c1-5(2)7(8)10-4-6-3-9-6/h6H,1,3-4H2,2H3/t6-/m1/s1

Synthetic route

oxiranyl-methanol (556-52-5) + epichlorohydrin (106-89-8) → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
With chlorine	93%
With chlorine	91.3%

epoxychloropropane (66794-22-7) + poly(methacrylic acid) (79-41-4) → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
Stage #1: epoxychloropropane With 10H-phenothiazine; sodium carbonate In dichloromethane at 70℃; for 1h; Large scale; Stage #2: poly(methacrylic acid) With tetrabutyl ammonium fluoride In dichloromethane; water at 102℃; for 3.5h; Large scale;	90%

sodium carbonate anhydride + poly(methacrylic acid) (79-41-4) + 4-methoxy-phenol (150-76-5) + epichlorohydrin (106-89-8) → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
tetramethlyammonium chloride In water	87.8%

poly(methacrylic acid) (79-41-4) + epichlorohydrin (106-89-8) → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
Stage #1: poly(methacrylic acid) With sodium hydroxide In methanol at 20℃; for 0.5h; Stage #2: epichlorohydrin In methanol at 35℃;	60%
With N-phenyl-1-naphthylamine; benzyltrimethylammonium chloride
With 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane; sodium carbonate; tetrabutyl-ammonium chloride for 1.83333h; Product distribution / selectivity; Heating / reflux;

allyl methacrylate (96-05-9) → 2,3-Epoxypropyl methacrylate (106-91-2) + 2-Methyl-oxirane-2-carboxylic acid allyl ester (140914-83-6)

Conditions	Yield
With sodium hydroxide; sodium tungstate; dihydrogen peroxide; Aliquat 336 In dichloromethane; phosphoric acid at 25℃; for 208h; Yields of byproduct given;	A 50% B n/a
With sodium hydroxide; sodium tungstate; dihydrogen peroxide; Aliquat 336 In dichloromethane; phosphoric acid at 40℃; for 30h; Product distribution; variation in reaction conditions;	A 50% B 4%
With sodium hydroxide; sodium tungstate; dihydrogen peroxide; Aliquat 336 In dichloromethane; phosphoric acid at 25℃; for 160h;	A 46.5% B 4%

oxiranyl-methanol (556-52-5) + Methacryloyl chloride (920-46-7) → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox;	35%
With pyridine; benzene

oxiranyl-methanol (556-52-5) + methacrylic acid methyl ester (80-62-6) → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
With potassium cyanide; 2,4-dimethyl-6-tert-butylphenol at 70 - 80℃; for 2h; Green chemistry;	25.3%

(2-oxo-1,3-dioxolane-4-yl)methyl methacrylate (13818-44-5) → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
1-methyl-3-(n-butyl)imidazolium iodide Product distribution / selectivity;	8.6%

poly(methacrylic acid) (79-41-4) + epichlorohydrin (106-89-8) → 2,3-Epoxypropyl methacrylate (106-91-2) + 2-Methyl-acrylic acid 2-chloro-1-hydroxymethyl-ethyl ester (109573-57-1)

Conditions	Yield
With potassium carbonate; 1.) Sn-P 1.) benzene, reflux, 20 h; 2.) acetone, reflux, 6 h; Yield given. Multistep reaction;

sodium t-butanolate (865-48-5) + (+-)-methacrylic acid-<3-chloro-2-hydroxy-propyl ester> → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
With diethyl ether; tert-butyl alcohol

epichlorohydrin (106-89-8) + potassium methacrylate → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
With hydroquinone
With N,N'-di(2-naphthyl)-p-phenylenediamine; tetramethlyammonium chloride

epichlorohydrin (106-89-8) + sodium methacrylate → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
With sodium hydroxide
With water; copper(l) chloride

potassium methacrylate (6900-35-2) → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
With tetraethylammonium chloride

sodium carbonate anhydride + 10H-phenothiazine (92-84-2) + poly(methacrylic acid) (79-41-4) + epichlorohydrin (106-89-8) → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
With tetramethlyammonium chloride In water

2-methylpropenal (78-85-3) + oxiranyl-methanol (556-52-5) → 2,3-Epoxypropyl methacrylate (106-91-2)

Conditions	Yield
Stage #1: 2-methylpropenal With tert-butylhypochlorite In tetrachloromethane at 20 - 50℃; for 5.5 - 6.5h; Stage #2: oxiranyl-methanol In tetrachloromethane at 0 - 20℃; for 2.5h;

allyl methacrylate (96-05-9) → 2,3-Epoxypropyl methacrylate (106-91-2) + 2-Methyl-oxirane-2-carboxylic acid oxiranylmethyl ester (140914-84-7)

Conditions	Yield
With dihydrogen peroxide; [(tmtacn)MnIV(μ-O)3MnIV(tmtacn)](CH3COO)2 In water at 5℃; for 2h; pH=3.6; Aqueous oxalate buffer;

2,3-Epoxypropyl methacrylate (106-91-2) → Glycidyl isobutyrate (3669-66-7)

Conditions	Yield
With hydrogen In 1,4-dioxane at 20℃; under 760.051 Torr; for 9h; Reagent/catalyst; chemoselective reaction;	100%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 6h;	100%
With hydrogen; 5percent Pd/C(en) In tetrahydrofuran at 20℃; for 3h; Catalytic hydrogenation;	94%
With hydrogen In methanol at 25℃; for 24h; Reagent/catalyst; chemoselective reaction;	93%
With hydrogen In methanol at 25℃; for 24h; Reagent/catalyst; chemoselective reaction;	79%

2,3-Epoxypropyl methacrylate (106-91-2) + benzoic acid (65-85-0) → 2-hydroxy-3-[(2-methylacryloyl)oxy]propyl benzoate

Conditions	Yield
Stage #1: 2,3-Epoxypropyl methacrylate; benzoic acid With triphenylantimony at 100℃; for 2h; Stage #2: With triphenylphosphine at 100℃;	100%
With tetrabutylammomium bromide In acetonitrile for 5h; Heating;	98%

[2-(dimethoxy-phosphoryl)-ethylsulfanyl]-acetic acid + 2,3-Epoxypropyl methacrylate (106-91-2) → 2-Methyl-acrylic acid 3-{2-[2-(dimethoxy-phosphoryl)-ethylsulfanyl]-acetoxy}-2-hydroxy-propyl ester

Conditions	Yield
With chromium diisopropylsalicylate In toluene at 70℃; for 15h;	100%

2,3-Epoxypropyl methacrylate (106-91-2) + 4-chloro-aniline (106-47-8) → C13H16ClNO3 (82178-52-7)

Conditions	Yield
In neat (no solvent) at 60℃; for 18h; regioselective reaction;	100%

2,3-Epoxypropyl methacrylate (106-91-2) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → 2-hydroxy-3-(phenyl(3-(trimethoxysilyl)propyl)amino)propyl methacrylate

Conditions	Yield
With dmap; dibutyltin dilaurate at 20℃;	100%

carbon dioxide (124-38-9) + 2,3-Epoxypropyl methacrylate (106-91-2) → (2-oxo-1,3-dioxolane-4-yl)methyl methacrylate (13818-44-5)

Conditions	Yield
With 1-methyl-1-N-propylpyrrolidinium bromide; triflate salt of a tricarbonyl rhenium(I) bipyridine complex at 80℃; under 11251.1 Torr; for 1h;	99%
With methyl-triphenylphosphonium iodide at 25℃; under 760.051 Torr; for 36h; Time;	99%
With tri-n-butyl-(2-hydroxyethyl)phosphonium iodide In neat (no solvent) at 90℃; under 7500.75 Torr; for 3h;	99%

mono-(6-deoxy-6-(1-piperazinyl))-β-cyclodextrin (131991-62-3) + 2,3-Epoxypropyl methacrylate (106-91-2) → MCD (1636146-18-3)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 24.5h; Inert atmosphere;	99%

2,3-Epoxypropyl methacrylate (106-91-2) + C14H20O4S → C28H40O10S

Conditions	Yield
In ethanol; acetic acid butyl ester at 60℃; for 18h;	99%

Adipic acid (124-04-9) + 2,3-Epoxypropyl methacrylate (106-91-2) → 1,6-bis[2-hydroxy-3-methacryloyloxypropyl] hexanedioate

Conditions	Yield
With triphenylphosphine at 90℃; for 3h;	99%
With methoxyhydroquinone; triphenylphosphine at 90℃; for 3h;	99%
With triphenylphosphine at 90℃; for 3h;	99%

undecanedioic acid (1852-04-6) + 2,3-Epoxypropyl methacrylate (106-91-2) → 1,11-bis({2-hydroxy-3-[(2-methylprop-2-enoyl)oxy]propyl})undecanedioate

Conditions	Yield
With triphenylphosphine at 90℃; for 3h;	99%
With methoxyhydroquinone; triphenylphosphine at 90℃; for 3h;	99%
With triphenylphosphine at 90℃; for 3h; Concentration;	99%

brassylic acid (505-52-2) + 2,3-Epoxypropyl methacrylate (106-91-2) → bis[methacryloyloxy-2-hydroxy-propyl] tridecanedioate

Conditions	Yield
With triphenylphosphine at 90℃; for 3h;	99%

4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE (36768-62-4) + 2,3-Epoxypropyl methacrylate (106-91-2) → C16H30N2O3

Conditions	Yield
In acetonitrile at 20℃; for 24h;	99%

2,3-Epoxypropyl methacrylate (106-91-2) + C16H35N3O → C23H45N3O4

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h;	99%

2,3-Epoxypropyl methacrylate (106-91-2) + C28H60N3O(1+)*Br(1-) → C35H70N3O4(1+)*Br(1-)

Conditions	Yield
In neat (no solvent) at 130℃; for 5h;	99%

2,3-Epoxypropyl methacrylate (106-91-2) → 3-methacrylatopropyl-1,2-episulfide (3139-91-1)

Conditions	Yield
With sodium thiocyanide In neat (no solvent) at 20℃; for 1.5h; Green chemistry;	98%
With silica gel; thiourea In dichloromethane at 20℃; for 0.5h;	97%
With thiourea on CaCO3 at 60 - 70℃; for 0.116667h; neat (no solvent);	97%

2,3-Epoxypropyl methacrylate (106-91-2) → 2-methylacrylic acid 3-hydroxypropyl ester (2761-09-3)

Conditions	Yield
With chloroaluminium tetrahydroborate on poly(4-vinylpyridine) In ethanol for 7h; Heating;	98%

α,β-poly(N-2-hydroxyethyl)-D,L-aspartamide + 2,3-Epoxypropyl methacrylate (106-91-2) → copolymer PHG containing vinyl groups

Conditions	Yield
With dmap In N,N-dimethyl acetamide at 25℃; for 48h;	98%

2,3-Epoxypropyl methacrylate (106-91-2) + acetic anhydride (108-24-7) → (2,3-diacetoxypropyl) methacrylate (29601-68-1)

Conditions	Yield
With sodium tetrahydroborate for 2h; Reflux;	98%
With phosphomolybdic acid supported on silica gel at 20℃; for 0.0833333h;	96%
With boric acid for 2h; Reflux;	96%
(TBA)4PFeW11O39*3H2O at 100℃; for 2.3h;	93%

1,12-dodecanedioic acid (693-23-2) + 2,3-Epoxypropyl methacrylate (106-91-2) → 1,12-bis[2-hydroxy-3-methacryloyloxypropyl] dodecanedioate

Conditions	Yield
With triphenylphosphine at 90℃; for 3h;	98%

phosgene (75-44-5) + 2,3-Epoxypropyl methacrylate (106-91-2) → C8H10Cl2O4

Conditions	Yield
With tetrabutyl-ammonium chloride at -30 - 25℃; for 0.1h;	98%

carbon disulfide (75-15-0) + 2,3-Epoxypropyl methacrylate (106-91-2) → 5-(methacryloyloxy)methyl-1,3-oxathiolane-2-thione

Conditions	Yield
With triethylamine In nitromethane at 25℃; for 6h;	97%
lithium bromide In tetrahydrofuran for 17h; Ambient temperature;	93%
With lithium tert-butoxide In neat (no solvent) at 20℃; for 5h; stereoselective reaction;	89%
With lithium tert-butoxide In neat (no solvent) at 25℃; for 5h; Sealed tube; regioselective reaction;	89%

2,3-Epoxypropyl methacrylate (106-91-2) + [3-(4-hydroxy-3-methoxy-phenyl)-propylsulfanyl]-acetic acid → C26H36O10S

Conditions	Yield
In ethanol; acetic acid butyl ester at 50℃; for 20h;	97%

2,3-Epoxypropyl methacrylate (106-91-2) + acetic anhydride (108-24-7) → C9H13ClO4

Conditions	Yield
With nickel(II) chloride hexahydrate In ethanol at 20℃; for 0.5h; regioselective reaction;	97%

2,3-Epoxypropyl methacrylate (106-91-2) → 2-hydroxy-3-iodopropyl 2-methylpropenoate

Conditions	Yield
With Silphos; iodine at 20℃; for 0.25h;	96%
With samarium(III) chloride; sodium iodide In acetonitrile at 20℃; for 0.25h;	92%
With quaternary ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; water In acetonitrile for 0.5h; Heating;	90%
With N-iodosaccharine; triphenylphosphine In water; acetonitrile at 20℃; for 0.05h;	86%
With [(PhNH)P2(NPh)2]2NPh; water; iodine In acetonitrile at 20℃; for 0.133333h;	86%

2,3-Epoxypropyl methacrylate (106-91-2) → 3-chloro-2-hydroxypropyl methacrylate (13159-52-9)

Conditions	Yield
With quaternary ammonium chloride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; water In acetonitrile for 0.5h; Heating;	96%
With N-chloro-succinimide; triphenylphosphine In water; acetonitrile at 20℃; for 0.05h;	95%
With N-chloro-succinimide; Silphos at 20℃; for 0.0833333h;	94%

2,3-Epoxypropyl methacrylate (106-91-2) + C15H22O4S → C29H42O10S

Conditions	Yield
In ethanol; acetic acid butyl ester at 90℃; for 10h;	96%

2,3-Epoxypropyl methacrylate (106-91-2) → 2-methylacrylic acid 3-azido-2-hydroxypropyl ester

Conditions	Yield
With sodium azide; poly[N-(2-aminoethyl)acrylamido]trimethylammonium chloride In water at 20℃; for 12h;	95%
With sodium azide; 1-(4-sulfonic acid)butyl-3-methylimidazolium chloride In neat (no solvent) at 80℃; for 0.416667h; Reagent/catalyst; Ionic liquid; Green chemistry; regioselective reaction;	95%
With 1‑(1‑carboxymethyl)‑3‑methylimidazolium tetrafluoroborate; sodium azide In neat (no solvent) at 60℃; for 0.45h; Reagent/catalyst; Green chemistry; regioselective reaction;	94%

2,3-Epoxypropyl methacrylate (106-91-2) + ammonium thiocyanate (1147550-11-5) → 2-hydroxy-3-thiocyanatopropyl methacrylate

Conditions	Yield
In acetonitrile for 2.5h; Reflux; regioselective reaction;	95%
With melamine-N2,N4,N6-trisulfonic acid; silica gel at 20℃; for 0.0333333h; Neat (no solvent); Grinding; regioselective reaction;	95%
With SiO2 supported Al(HSO4)3 at 20℃; for 0.0833333h; Grinding; neat (no solvent); regioselective reaction;	95%

2,3-Epoxypropyl methacrylate (106-91-2) + (14-methacryloyloxy-2-oxatetradecyl)-15-crown-5 (503003-38-1) → Polymer, radical copolymerization, ether-insoluble, Mn (GPC): 9800, Mw/Mn (GPC): 2.68; Monomer(s): glycidyl methacrylate, 91 mol percent; (14-methacryloyloxy-2-oxatetradecyl)-15-crown-5, 9 mol percent

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 20h;	95%

Upstream product

• 79-41-4 poly(methacrylic acid) 
• 106-89-8 epichlorohydrin 
• 78-85-3 2-methylpropenal 
• 556-52-5 oxiranyl-methanol 
• 66794-22-7 epoxychloropropane 
• 4245-37-8 vinyl methacrylate 
• 80-62-6 methacrylic acid methyl ester 
• 96-05-9 allyl methacrylate 
• 13818-44-5 (2-oxo-1,3-dioxolane-4-yl)methyl methacrylate 
• 92-84-2 10H-phenothiazine 
• 6900-35-2 potassium methacrylate 
• 150-76-5 4-methoxy-phenol 
• 865-48-5 sodium t-butanolate 
• 920-46-7 Methacryloyl chloride 

Downstream Products

• 37817-81-5 3-dimethylamino-2-hydroxypropyl (meth)acrylate 
• 55526-86-8 2-Hydroxy-3-(β-naphthoxy)-propyl methacrylate 
• 16926-87-7 2-hydroxy-3-phenoxypropyl methacrylate 
• 13159-52-9 3-chloro-2-hydroxypropyl methacrylate 
• 3066-70-4 2,3-dibromopropyl 2-methylpropenoate 
• 1709-71-3 1-(acryloyloxy)-3-(methacryloyloxy)-2-propanol 
• 97-90-5 EDMA 
• 186495-09-0 Pt(P(C₆H₅)3)2(CH₂C(CH₃)COOCH₂CHCH₂O) 
• 1286215-76-6 C₅₆H₁₀₀N₂O₁₈P₂ 
• 101927-31-5 3-(4-formylphenoxy)-2-hydroxypropyl methacrylate 
• 1374787-10-6 2-(acetyloxy)-3-(benzylsulfanyl)propyl 2-methylacrylate 
• 905707-85-9 2-hydroxy-3-(2-(4-isobutylphenyl)propanoyloxy)propyl methacrylate 
• 1565-94-2 (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate 
• 101525-90-0 glycerine dimethacrylate 

Relevant articles and documents

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The invention relates to the field of organic synthesis and discloses an (methyl) acrylic acid ether hydroxyl alkane ester synthesis method. The method includes steps: subjecting methyl acrylic acid and epoxy chloropropane to reaction to generate acrylic ester with an epoxy group; subjecting the epoxy group to positioning and ring opening to enable a hydroxyl at 2-site carbon and a sterically hindered ether bond at a 3 site; subjecting to reaction with a primary alcohol compound to generate a target product. The method has advantages that side reactions in a synthesizing process are less, polymer crystallinity can be changed, mechanical performances such as tensile strength of a polymer are enhanced, and the hydrophilic performance can be changed.

From epoxide to cyclodithiocarbonate Telechelic polycyclooctene through chain-transfer ring-opening metathesis polymerization (ROMP): Precursors to non-isocyanate polyurethanes (NIPUS)

Telechelic polycyclooctenes (PCOEs) have been successfully synthesized by ring-opening metathesis polymerization (ROMP)/cross-metathesis (CM) of cyclooctene (COE) using Grubbs' second-generation catalyst (G2) in the presence of epoxide-functionalized chain-transfer agents (CTAs). The monofunctional epoxide oxiran-2-ylmethyl acrylate CTA (1) afforded the isomerized α-(glycidyl alkenoate),ω-propenyl functional (IMF) PCOEs. The use of 1,4-benzoquinone (BZQ) as additive completely inhibited the C=C isomerization process, thereby leading selectively to α-(glycidyl alkenoate),ω-vinyl telechelic (MF) PCOE. On the other hand, difunctional epoxide CTAs, bis(oxiran-2-ylmethyl) fumarate (3), bis(oxiran-2-ylmethyl) maleate (4), bis(oxiran-2-ylmethyl) (E)-hex-3-enedioate (5), and (Z)-1,4-bis(oxiran-2-ylmethoxy)but-2-ene (6), selectively afforded the corresponding α,ω-di(glycidyl alkenoate) telechelic PCOEs (DF) along with minor amounts of cyclic nonfunctional (CNF) PCOE. In the presence of these difunctional symmetric CTAs, the mechanism is proposed to proceed through a tandem one-pot CM/ROMP/ring-closing metathesis (RCM) approach. CM was more effective with Z-than E-configurated CTAs (4 > 6 ? 3 ? 5), regardless of the presence of a methylene group in-between the C=C double bond and the glycidyl moiety. Subsequent dithiocarbonatation of the α,ω-diepoxide telechelic PCOEs upon reaction with CS2 in the presence of LiBr quantitatively afforded the first examples of bis(cyclodithiocarbonate) end-functional PCOEs. Ensuing aminolysis of the bis(cyclodithiocarbonate) telechelic PCOEs with the polyether (triethylene glycol) diamine JEFFAMINE EDR-148 quantitatively afforded, at room temperature without any added catalyst, the desired poly(mercaptothiourethane)s NIPUs, as evidenced from FTIR spectroscopy, TGA, and DSC analyses.

Production method of glycidyl methacrylate

The invention relates to a production method of glycidyl methacrylate. The method comprises a reaction process and a post-treatment process. The reaction process is characterized in a one-step synthesis method. According to the reaction process, methacrylic acid and sodium carbonate are subjected to a neutralization reaction in excessive epichlorohydrin, such that sodium salt is prepared; without solid-liquid separation, system water content is removed with an azeotropic solvent; under the catalysis effect of a phase transfer catalyst, the glycidyl methacrylate is prepared. The post-treatment process comprises the following steps: a reaction finished liquid is washed; liquid separation is carried out, such that an organic phase is obtained; solvent recovery is carried out with a film evaporation device; and finished product distillation is carried out with a molecular distillation device. With the production method provided by the invention, production process and industrial equipment can be simplified, and operation is convenient. During the post-treatment process, phenomena of poor product polymerization rate and yield caused by high temperature, poor heat transfer effect, low distillation efficiency and the like of a conventional kettle distillation method can be avoided. With the method provided by the invention, product quality and yield can be effectively ensured. The obtained product has a purity higher than 98% and a yield of 85-90%.

Glycidyl methacrylate or glycidyl acrylate manufacturing method

The invention relates to a manufacturing method of glycidyl methacrylate or glycidyl acrylate. The invention provides glycidyl (meth)acrylate with low impurity content. The manufacturing method of glycidyl (meth)acrylate comprises a step of reacting epichlorohydrin and (meth)acrylic acid alkali metal salt or (meth)acrylic acid in the presence of catalyst and a step of washing the reaction liquid obtained through the reaction at the temperature ranging from minus 13 DEG C to 20 DEG C.

Manufacturing method of glycidyl methacrylate

PROBLEM TO BE SOLVED: To provide a method for producing glycidyl methacrylate from an alkali metal salt of methacrylic acid and epichlorohydrin, which method suppresses generation of a polymer to improve productivity.SOLUTION: There is provided a method for producing glycidyl methacrylate from an alkali metal salt of methacrylic acid and epichlorohydrin, wherein the productivity can be improved by suppressing generation of a polymer and preventing the blockage trouble of pipes and the like by maintaining a concentration of a bisphenol-based polymerization inhibitor at 100 ppm or more.

Preparation of glycidyl methacrylate

PROBLEM TO BE SOLVED: To provide a method for producing glycidyl methacrylate from alkali metal salt of methacrylic acid and epichlorohydrin, in which the deterioration of interfacial properties during removal of the by-produced alkali metal hydrochloride by water washing is prevented.SOLUTION: In a process for obtaining an alkali metal salt of methacrylic acid from methacrylic acid and alkali metal carbonate, an alkali metal carbonate in which water-insoluble matter is removed beforehand, is used. By using an alkali metal carbonate in which water-insoluble matter has been removed, insoluble solids near the interface at the time of water-washing operation for removing the alkali metal hydrochloride which is by-produced during the reaction of alkali metal salt of methacrylic acid and epichlorohydrin to obtain glycidyl methacrylate, no longer occurs and a clear interface can be obtained, and the loss of the oil layer discharged together with the water layer can be suppressed.

PROCESS FOR PRODUCING GLYCIDYL (METH)ACRYLATE

Provided is glycidyl(meth)acrylate which is reduced in the content of impurities including chlorine. This process comprises reacting epichlorohydrin with an alkali metal (meth)acrylate in the presence of a catalyst to produce glycidyl(meth)acrylate, the process including a step in which the reaction is conducted while making a Bronsted acid present in the reaction system in an amount of 0.0001-0.08 mol per mol of the alkali metal (meth)acrylate.