760-93-0

Basic information

• Product Name: Methacrylic anhydride
• Synonyms: 1-Methylacrylic anhydride;2-methyl-2-propenoicacianhydride;2-Propenoic acid, 2-methyl-, anhydride;2-Propenoicacid,2-methyl-,anhydride;Methacrylic acid anhydride;methacrylicacidanhydride;Methacryloyl anhydride;methacryloylanhydride
• CAS NO: 760-93-0
• Molecular Formula: C₈H₁₀O₃
• Molecular Weight: 154.16
• EINECS: 212-084-8
• Product Categories: Organic acids;Carbonyl Compounds;Carboxylic Acid Anhydrides;Organic Building Blocks;Anhydride Monomers;Monomers;Polymer Science
• Mol File: 760-93-0.mol
• Article Data: 33

Chemical Properties

• Melting Point: -20°C
• Boiling Point: 87 °C13 mm Hg(lit.)
• Flash Point: 184 °F
• Appearance: liquid
• Density: 1.04 g/mL at 20 °C
• Vapor Pressure: 0.294mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Miscible with ethanol and ether.
• Water Solubility: 98g/L at 20℃
• Sensitive: Moisture Sensitive
• Stability: Stable. Flammable. Moisture-sensitive.
• BRN: 1761982
• CAS DataBase Reference: Methacrylic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Methacrylic anhydride(760-93-0)
• EPA Substance Registry System: Methacrylic anhydride(760-93-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20-37/38-41
• Safety Statements: 26-39
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 1
• RTECS: OZ5700000
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 760-93-0(Hazardous Substances Data)

Usage

Chemical Properties

liquid

Uses

Methacrylic anhydride is a reactive monomer used for the preparation of different type of monomers under mild reaction conditions. It finds applications in light-curing coatings, cross-linked materials like synthetic resin. It acts as an intermediate for the preparation of fibers and resins.

General Description

Liquid.

Air & Water Reactions

Reacts exothermically with water to form methacrylic acid.

Reactivity Profile

Methacrylic anhydride reacts exothermically with water. The reactions are sometimes slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.

Fire Hazard

(Non-Specific -- Methacrylic Acid) Methacrylic anhydride may burn but may not ignite readily. Flammable/ poisonous gases may accumulate in tanks and hopper cars. Some of these materials may ignite combustibles (wood, paper, oil, etc.).

Purification Methods

Distil the anhydride at 2mm pressure, immediately before use, in the presence of hydroquinone. [Beilstein 2 IV 1537.]

InChI:InChI=1/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3

Synthetic route

poly(methacrylic acid) (79-41-4) → methacryloyl anhydride (760-93-0)

Conditions	Yield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 0.5h;	99%
With magnesium dimethacrylate; di-tert-butyl dicarbonate at 25℃; for 4h; Reagent/catalyst;	99%
With 10H-phenothiazine; trifluorormethanesulfonic acid; acetic anhydride at 95℃; Reagent/catalyst; Temperature;	95%

Methacryloyl chloride (920-46-7) → methacryloyl anhydride (760-93-0)

Conditions	Yield
With pyridine; 1,1,1-trichloro-3,3,3-trifluoro-propan-2-one; water In toluene for 0.5h; Ambient temperature;	93%
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at -10℃; for 3h;	80%
With sodium hydroxide; tetrabutyl-ammonium chloride In toluene at -10℃; for 3h;	7%

poly(methacrylic acid) (79-41-4) + Methacryloyl chloride (920-46-7) → methacryloyl anhydride (760-93-0)

Conditions	Yield
With triethylamine In benzene at 70℃;	92%
Stage #1: Methacryloyl chloride With pyridine; hydroquinone In toluene Stage #2: poly(methacrylic acid) In toluene at 50 - 65℃;	83%
With triethylamine In benzene
With sodium hydroxide In water
With sodium hydroxide In water

sodium methacrylate (5536-61-8) + chloroformic acid ethyl ester (541-41-3) → methacryloyl anhydride (760-93-0) + carboethoxymethacrylic anhydride (21982-91-2)

Conditions	Yield
With 4-methoxy-phenol; tetrabutylammomium bromide In H2O (water) < 309.3g; toluene 192g at 15℃; for 4h;	A n/a B 87.5%
With 4-methoxy-phenol In water at 5 - 35℃; for 7 - 30h;
tributylphenylphosphonium chloride at 10℃; for 3h;

sodium methacrylate (5536-61-8) + chloroformic acid ethyl ester (541-41-3) → methacryloyl anhydride (760-93-0) + carboethoxymethacrylic anhydride (21982-91-2) + Diethyl carbonate (105-58-8)

Conditions	Yield
With 4-methoxy-phenol; tetrabutylammomium bromide In water at 20℃; for 3h;	A n/a B 80% C n/a
tetrabutyl phosphonium bromide at 10℃; for 4.5h;
methyl(tri-n-octyl)ammonium bromide at 10℃; for 1.5h;

2-methyladamantan-2-ol (702-98-7) → 2-methyl-2-adamantyl methacrylate (177080-67-0) + methacryloyl anhydride (760-93-0)

Conditions	Yield
	A 40% B n/a

isobutene (115-11-7) → poly(methacrylic acid) (79-41-4) + methacryloyl anhydride (760-93-0)

Conditions	Yield
With oxygen; silica gel; Te/Pd-containing-silica-supported catalyst In water; tert-butyl alcohol at 75℃; under 18001.8 - 36003.6 Torr; for 0.75h; Product distribution / selectivity; Autoclave;	A 34.2% B 17.5%

4-methyleneoxetan-2-one (674-82-8) + poly(methacrylic acid) (79-41-4) → methacryloyl anhydride (760-93-0)

Conditions	Yield
With copper (I) acetate

poly(methacrylic acid) (79-41-4) + benzoyl chloride (98-88-4) → methacryloyl anhydride (760-93-0) + benzoyl (meth)acrylate (46318-87-0) + benzoic acid anhydride (93-97-0)

Conditions	Yield
With P4-VP In dichloromethane at 0℃; for 1h; Yield given. Yields of byproduct given;

potassium methacrylate → methacryloyl anhydride (760-93-0)

Conditions	Yield
With thionyl chloride; Petroleum ether

Methacryloyl chloride (920-46-7) + sodium methacrylate → methacryloyl anhydride (760-93-0)

chloroformic acid ethyl ester (541-41-3) + potassium methacrylate (6900-35-2) → methacryloyl anhydride (760-93-0) + carboethoxymethacrylic anhydride (21982-91-2) + Diethyl carbonate (105-58-8)

Conditions	Yield
at 10℃;

sodium methacrylate (5536-61-8) + chloroformic acid ethyl ester (541-41-3) → methacryloyl anhydride (760-93-0) + diethyl dicarbonate (1609-47-8) + carboethoxymethacrylic anhydride (21982-91-2) + Diethyl carbonate (105-58-8)

tempol (2226-96-2) + poly(methacrylic acid) (79-41-4) → methacryloyl anhydride (760-93-0)

Conditions	Yield
With phosphoric acid; acetic anhydride; sodium hydrogencarbonate In hexane; water

HO-TEMPO + poly(methacrylic acid) (79-41-4) → methacryloyl anhydride (760-93-0)

Conditions	Yield
With sodium hydroxide; phosphoric acid; acetic anhydride In hexane; water
With sodium hydroxide; phosphoric acid; acetic anhydride In hexane; water

isobutene (115-11-7) → 2-methylpropenal (78-85-3) + poly(methacrylic acid) (79-41-4) + methacryloyl anhydride (760-93-0)

Conditions	Yield
With oxygen; 4-methoxy-phenol; palladium matal-containing silica-supported catalyst In water; tert-butyl alcohol at 90℃; for 6h; Product distribution / selectivity;
With oxygen at 110℃; under 36003.6 Torr; Gas phase;	A 27.8 %Chromat. B 53 %Chromat. C 7.4 %Chromat.

poly(methacrylic acid) (79-41-4) + acetic anhydride (108-24-7) → methacryloyl anhydride (760-93-0)

Conditions	Yield
With TEMPOL; 2,6-di-tert-butyl-4-methyl-phenol; 2,4-dimethyl-6-tert-butylphenol at 93℃; under 18 - 140 Torr; Product distribution / selectivity; Air atmosphere;
With 10H-phenothiazine at 80 - 90℃; under 760.051 Torr;
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 10H-phenothiazine at 100 - 105℃; for 2h;	135.5 g

poly(methacrylic acid) (79-41-4) + acetic anhydride (108-24-7) → methacryloyl anhydride (760-93-0) + methacrylic acid acetate (76392-13-7) + acetic acid (64-19-7)

Conditions	Yield
acidic ion exchanger Lewatit K2431 at 76℃; Polymerization inhibitior;

poly(methacrylic acid) (79-41-4) + methacrylic acid acetate (76392-13-7) + acetic anhydride (108-24-7) → methacryloyl anhydride (760-93-0) + acetic acid (64-19-7)

Conditions	Yield
acidic ion exchanger Lewatit K2431 at 76℃; Polymerization inhibitior;

methanol (67-56-1) + 2-methylpropenal (78-85-3) → 1,1-dimethoxy-2-methylprop-1-ene (5634-54-8) + propene (187737-37-7) + poly(methacrylic acid) (79-41-4) + Methyl isobutyrate (547-63-7) + Isobutyl methacrylate (97-86-9) + methacryloyl anhydride (760-93-0) + isobutyraldehyde (78-84-2) + methacrylic acid methyl ester (80-62-6) + 3-hydroxy-2-methyl-1-propene (513-42-8)

Conditions	Yield
With magnesium hydroxide; oxygen at 80℃; under 2250.23 Torr; for 2h; Reagent/catalyst;

...Expand

methacryloyl anhydride (760-93-0) + 5-hydroxy-6-methyluracil (7417-28-9) → 6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl methacrylate

Conditions	Yield
With pyridine; hydroquinone at 20℃;	100%

methacryloyl anhydride (760-93-0) + 1-amino-4-hydroxy-2-[2'-[4'-(2'-hydroxyethoxy)phenoxy]ethoxy]anthraquinone (17728-11-9) → C28H25NO8

Conditions	Yield
Stage #1: methacryloyl anhydride; 1-amino-4-hydroxy-2-[2'-[4'-(2'-hydroxyethoxy)phenoxy]ethoxy]anthraquinone With triethylamine; dmap; hydroquinone In DMF (N,N-dimethyl-formamide) at 20℃; for 24h; Stage #2: Heating / reflux;	100%

THPE PO (434329-65-4) + methacryloyl anhydride (760-93-0) → THPE PO MA

Conditions	Yield
With pyridine at 80℃; for 6.5h;	100%

methacryloyl anhydride (760-93-0) + 4-Phenylphenol (92-69-3) → [1,1'-biphenyl]-4-ylmethacrylate (46904-74-9)

Conditions	Yield
With dmap; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 80℃; for 40h;	100%

dimethyl 2-hydroxyethylphosphonate (54731-72-5) + methacryloyl anhydride (760-93-0) → dimethyl (2-methacryloyloxyethyl)phosphonate (22432-83-3)

Conditions	Yield
With 1-methyl-1H-imidazole In butanone at 60℃; for 6h; Inert atmosphere;	100%

methacryloyl anhydride (760-93-0) + dimethyl (γ-hydroxypropyl)phosphonate (54731-74-7) → dimethyl (3-methacryloyloxypropyl)phosphonate (252210-28-9)

Conditions	Yield
With 1-methyl-1H-imidazole In butanone at 60℃; for 6h; Inert atmosphere;	100%

methacryloyl anhydride (760-93-0) + 6A-(6-aminohexylamino)-6A-deoxy-β-cyclodextrin (131991-61-2) → (1-methacrylamidohexyl)amino-6-deoxy-β-cyclodextrin (1080030-24-5)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	100%

hexa-1,5-diene-3,4-diol (19700-96-0, 19700-97-1, 58208-04-1, 112571-38-7, 144829-86-7, 1069-23-4) + methacryloyl anhydride (760-93-0) → 4-[(2-methylprop-2-enoyl)oxy]hexa-1,5-dien-3-yl 2-methylprop-2-enoate (1361054-19-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 1.5h;	100%

methacryloyl anhydride (760-93-0) + β-naphthol (135-19-3) → β-naphthyl methacrylic ester (10475-46-4)

Conditions	Yield
With triphenyl phosphite; 2,6-di-tert-butyl-4-methyl-phenol; magnesium oxide In toluene at 80℃; for 3h; Reagent/catalyst;	100%
With magnesium oxide In toluene at 80℃; for 3h; Catalytic behavior; Concentration; Reagent/catalyst; Temperature;	100%

methacryloyl anhydride (760-93-0) + 4-Hydroxybenzophenone (1137-42-4) → 4-hydroxybenzophenone ester of metacrylic acid (56467-43-7)

Conditions	Yield
With 2,4-dimethyl-6-tert-butylphenol; sulfuric acid; 4-methoxy-phenol at 90℃; for 6h; Air introduction;	99.4%
With sulfuric acid In methanol at 90℃; for 2h; Temperature; Large scale;	99.7%
With tempol; 2,4-dimethyl-6-tert-butylphenol; 4-methoxy-phenol; magnesium bromide at 90℃; for 6h; Reagent/catalyst;

methacryloyl anhydride (760-93-0) + phenol (108-95-2) → phenyl methacrylate (2177-70-0)

Conditions	Yield
With sulfuric acid at 80℃; for 8h; Product distribution / selectivity;	99.1%
at 25℃; for 24h;	90%
With sulfuric acid at 80℃; for 8h; Product distribution / selectivity; Industry scale;
at 120℃; for 5h; Product distribution / selectivity;
With magnesium monohydroxide; di-tert-butyl dicarbonate; lithium chloride at 25℃; under 760.051 Torr; for 24h; Time;

succinic acid anhydride (108-30-5) + inulin, MW: ca. 5000 Da, isolated from Dahlia Tubers + methacryloyl anhydride (760-93-0) → methacrylated/succinilated inulin, MW: 9000 Da

Conditions	Yield
Stage #1: inulin, MW: ca. 5000 Da, isolated from Dahlia Tubers; methacryloyl anhydride; triethylamine In N,N-dimethyl-formamide at 25℃; for 24h; Stage #2: succinic acid anhydride; triethylamine In N,N-dimethyl-formamide at 25℃; for 24h; Further stages.;	99%

methacryloyl anhydride (760-93-0) + N-(2-aminoethyl)benzeneamine (1664-40-0) → N-phenylethylenediamine methacrylamide (1149340-19-1)

Conditions	Yield
In methanol at 0℃; for 3h;	99%

methacryloyl anhydride (760-93-0) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → N-methacryloyl-N-methyl-1-amino-1-deoxy-D-glucitol

Conditions	Yield
In methanol at 15 - 25℃; for 2h; Solvent;	99%

1,4-Dihydroxynaphthalene (571-60-8) + methacryloyl anhydride (760-93-0) → 1,4-dimethacryloyloxynaphthalene

Conditions	Yield
With dmap In dichloromethane at 35℃; Flow reactor;	99%

methacryloyl anhydride (760-93-0) + Isosorbide (652-67-5) → isosorbide bis-methacrylate (108646-62-4)

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃; for 18h;	98.2%
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere; Cooling with ice;	90.8%

α,β-poly(N-2-hydroxyethyl)-D,L-aspartamide + methacryloyl anhydride (760-93-0) → copolymer PHM containing vinyl groups

Conditions	Yield
With triethylamine In N,N-dimethyl acetamide at 40℃; for 48h;	98%

methacryloyl anhydride (760-93-0) + 1,4-bis-[(2-hydroxy-ethylsulfanyl)-methyl]-benzene (7321-13-3) → 1,4-bis(2-methacryloyloxyethylthio)xylylene (112503-98-7)

Conditions	Yield
Stage #1: methacryloyl anhydride; 1,4-bis-[(2-hydroxy-ethylsulfanyl)-methyl]-benzene With triethylamine In dichloromethane at 20℃; for 48h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water for 0.5h;	98%

methacryloyl anhydride (760-93-0) + 1,2-bis(hydroxyethylthiomethyl)benzene (117420-69-6) → 1,2-bis(methacryloyloxyethylthiomethyl)benzene (154865-01-7)

Conditions	Yield
Stage #1: methacryloyl anhydride; 1,2-bis(hydroxyethylthiomethyl)benzene With triethylamine In dichloromethane at 20℃; for 48h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water for 0.5h;	98%

methacryloyl anhydride (760-93-0) + C21H41NO2 → C25H45NO3

Conditions	Yield
With dmap at 60℃;	98%

methacryloyl anhydride (760-93-0) + α-naphthol (90-15-3) → 1-naphthyl methacrylate (19102-44-4)

Conditions	Yield
With lithium carbonate at 80℃; for 2h; Reagent/catalyst;	98%

methacryloyl anhydride (760-93-0) + 1,3,6-trimethyl-isobarbituric acid (135304-82-4) → 1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl methacrylate

Conditions	Yield
With pyridine; hydroquinone at 20℃; for 1h;	97%

poly(methacrylic acid) (79-41-4) + methacryloyl anhydride (760-93-0) + hydroquinone (123-31-9) → hex-1-ene-2,5-dicarboxylic acid (5363-70-2) + 4-hydroxyphenyl methacrylate (31480-93-0)

Conditions	Yield
at 120℃; for 4h; Product distribution / selectivity;	A 1% B 97%

2-Adamantanone (700-58-3) + methacryloyl anhydride (760-93-0) + methyllithium (917-54-4) → 2-methyl-2-adamantyl methacrylate (177080-67-0)

Conditions	Yield
Stage #1: 2-Adamantanone; methyllithium In tetrahydrofuran; diethyl ether at -25 - -20℃; for 1h; Stage #2: methacryloyl anhydride With triethylamine In tetrahydrofuran; diethyl ether at 25℃; for 1.5h;	97%
Stage #1: 2-Adamantanone; methyllithium In tetrahydrofuran; diethyl ether at -25 - -20℃; for 1h; Stage #2: methacryloyl anhydride In tetrahydrofuran; diethyl ether at 55℃; for 3h;	90%

methacryloyl anhydride (760-93-0) + bis(O,S-triphenylsilyl)-2-mercaptoethanol (491878-98-9) → C24H24O2SSi (1113062-54-6)

Conditions	Yield
In dichloromethane at 20℃; for 3h;	97%

methacryloyl anhydride (760-93-0) + (2R)-bornane-10,2-sultam (94594-90-8) → (3aS,6R,7aR)-1-[(2E)-but-2-enoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide (116195-15-4)

Conditions	Yield
Stage #1: (2R)-bornane-10,2-sultam With triethylamine; lithium chloride In tetrahydrofuran at -20℃; for 0.166667h; Stage #2: methacryloyl anhydride In tetrahydrofuran at -20 - -10℃; for 0.0833333h; Product distribution / selectivity;	96%
With triethylamine; lithium chloride In tetrahydrofuran for 4h; Ambient temperature;	95%

HO-[G3]-PGLSA-PEG-OMe + methacryloyl anhydride (760-93-0) → MA-[G3]-PGLSA-PEG-OMe

Conditions	Yield
With dmap In dichloromethane at 20℃;	96%
With dmap In dichloromethane at 20℃;	96%

methacryloyl anhydride (760-93-0) + C5H10O5S2 → C9H14O6S2

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 12h;	96%

methacryloyl anhydride (760-93-0) + C21H41NO2 → C26H47NO3

Conditions	Yield
With dmap at 60℃;	96%

Upstream product

• 115-11-7 isobutene 
• 67-56-1 methanol 
• 78-85-3 2-methylpropenal 
• 6900-35-2 potassium methacrylate 
• 79-41-4 poly(methacrylic acid) 
• 76392-13-7 methacrylic acid acetate 
• 108-24-7 acetic anhydride 
• 702-98-7 2-methyladamantan-2-ol 
• 2226-96-2 tempol 
• 5536-61-8 sodium methacrylate 
• 541-41-3 chloroformic acid ethyl ester 
• 920-46-7 Methacryloyl chloride 
• 98-88-4 benzoyl chloride 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 4245-38-9 Ethylene glycol dimethacrylate 
• 112889-27-7 N-ε-methacryloyl lysine 
• 28854-39-9 (+/-)-isobornyl methacrylate 
• 22414-62-6 tributylsilyl methacrylate 
• 80-62-6 methacrylic acid methyl ester 
• 136775-83-2 4-(N-hydroxybutyl-N-methylamino)benzaldehyde, methacrylate ester 
• 136775-86-5 4-(N-6-hydroxyhexyl-N-ethylamino)benzaldehyde, methacrylate ester 
• 59447-77-7 N-Hexadecylmethacrylamid 
• 79-41-4 poly(methacrylic acid) 
• 56467-43-7 4-hydroxybenzophenone ester of metacrylic acid 

Relevant articles and documents

Synthesis of 2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl methacrylates

2,4-Dioxo-1,2,3,4-tetrahydropyrimidin-5yl methacrylates were synthesized for the first time by reaction of 5-hydroxyuracil derivatives with methacrylic anhydride. 5-Hydroxyuracil derivatives are involved in this reaction in the dioxo form. 2005 Pleiades Publishing, Inc.

Multicatalytic Transformation of (Meth)acrylic Acids: a One-Pot Approach to Biobased Poly(meth)acrylates

Shifting from petrochemical feedstocks to renewable resources can address some of the environmental issues associated with petrochemical extraction and make plastics production sustainable. Therefore, there is a growing interest in selective methods for transforming abundant renewable feedstocks into monomers suitable for polymer production. Reported herein are one-pot catalytic systems, that are active, productive, and selective under mild conditions for the synthesis of copolymers from renewable materials. Each system allows for anhydride formation, alcohol acylation and/or acid esterification, as well as polymerization of the formed (meth)acrylates, providing direct access to a new library of unique poly(meth)acrylates.

Method for preparing N-hydroxyethylmethacrylamide

The invention discloses a method for preparing N-hydroxyethylmethacrylamide. Methacrylic anhydride moderately reacts with aminoethanol under low temperature. A generated byproduct methacrylic acid can be separated from a product through a distillation manner, and a production process is simple and feasible. The N-hydroxyethylmethacrylamide obtained by the method disclosed by the invention has high purity and high yield.