Methacrylic anhydride

HCID 12974CAS 760-93-0

Basic information

Standard SMILES
C=C(C)C(=O)OC(=O)C(=C)C
InChIKey
DCUFMVPCXCSVNP-UHFFFAOYSA-N
Molecular formula
C8H10O3
Average molar mass
154.16 g/mol
Monoisotopic mass
154.06299418

Overview

Methacrylic anhydride is a liquid. (EPA, 1998)

Names & identifiers

Preferred name
Methacrylic anhydride
IUPAC
2-methylprop-2-enoyl 2-methylprop-2-enoate
English name
Methacrylic anhydride
Molecular formula
C8H10O3
Molecular weight
154.17

Names & synonyms

METHACRYLIC ANHYDRIDEMethacrylic acid anhydrideMethacryloyl anhydride2-Methyl-2-propenoic acid anhydride2-Propenoic acid, 2-methyl-, anhydrideHSDB 6407EINECS 212-084-8NSC 24159UNII-N2RJR03340BRN 1761982N2RJR03340NSC-24159
Show more names
1-Methylacrylic anhydrideMETHACRYLIC ANHTDRIDEmethacrylicacidanhydride2-methyl-2-propenoicacianhydride276685-500MLmethacryloylanhydride
DTXSID608624042-Propenoic acid, 2-methyl-, 1,1'-anhydrideEC 212-084-84-02-00-01537 (Beilstein Handbook Reference)METHACRYLIC ANHYDRIDE [HSDB]BIS(METHACRYLIC ACID) ANHYDRIDERefChem:1568412Methyl2propenoic acid anhydride

Database identifiers

CAS
760-93-0
PubChem CID
12974
DTXSID
DTXSID60862404
UNII
N2RJR03340
EC Number
212-084-8
Nikkaji
J38.879C

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
43.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Acid Anhydrides, Other
SpringerMaterials PropertiesOptical coefficient
Density · 2 items

Specific gravity: 1.035

1.035 @25 °C

Viscosity3 mPa
Solubility · 2 items

> 10% in ether

> 10% in ethanol

Boiling Point · 3 items

192 °F at 5 mmHg (EPA, 1998)

89 °C at 5 mm Hg

240 °C @760 [mm Hg]

Physicochemical properties

Melting point
-20 °C · -20°C
Boiling point
87 °C13 · 87 °C13 mm Hg(lit.)
Density
1.04 g/mL · 1.04 g/mL at 20 °C
vapor pressure
90 Pa · 90Pa at 20℃
refractive index
20 · n20/D 1.453(lit.)
Flash point
184 °F · 184 °F

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 2.7% (5 of 184) of reports.

Danger

H302+H332 (57.6%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 184 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

2-Propenoic acid, 2-methyl-, 1,1'-anhydride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 1,1'-anhydride are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 28-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/5277

2-Propenoic acid, 2-methyl-, anhydride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelCorrosive
Fire Hazards(Non-Specific -- Methacrylic Acid) This material 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.). (EPA, 1998)
Health HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Hazards SummaryReacts with water exothermically producing methacrylic acid; [CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; May cause skin sensitization; [MSDSonline]
Reactive GroupHydrocarbons, Aliphatic Unsaturated

Safety & protection

Fire Fighting(Non-Specific -- Methacrylic Acid) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing.
First AidNote: No information on specific clinical effects of exposure was available.
Storage Conditions · 1 item

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/

Nonfire Spill Response · 1 item

(Non-Specific -- Methacrylic Acid) Do not touch spilled material; stop leak if you can do so without risk. For small spills, absorb with sand or other noncombustible absorbent material and place into containers for later disposal. For large spills, dike far ahead of spill for later disposal. (EPA, 1998)

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 3 items

... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Antidote and Emergency Treatment · 2 items

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at lO to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

Toxicity DataLC50 (mice) = 450 mg/m3/2h
Non-Human Toxicity ValuesLC50 Mouse ihl 450 mg/cu m/2 hr

Regulatory information

CERCLA Reportable Quantities · 1 item

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Methacrylic anhydride is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Safety data

F
10-21
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
OZ5700000
ridadr
UN 3265 8/PG 2

Chemistry & industry

Uses & manufacturing

U.S. Production2023: <75,000 lb
Industry UsesIntermediate
General Manufacturing Information · 3 items

Plastics Material and Resin Manufacturing

2-Propenoic acid, 2-methyl-, 1,1'-anhydride: ACTIVE

METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/

Applications · 3 items

DescriptionMethacrylic anhydride is a reactive monomer used primarily as a monomer in the preparation of polymers, particularly poly(methacrylic acid) and its copolymers. The reaction mechanism involves the formation of covalent bonds between methacrylic acid and acetic anhydride molecules, resulting in the formation of a novel compound. The newly formed compound then undergoes a series of reactions including hydrolysis and polymerisation. Methacrylic anhydride produces polymers with good chemical and thermal stability, which are used in a wide range of applications in various industries such as bio-renewable resins, pH-sensitive hydrogels, thermoset plastics, coatings, adhesives and plastics.

UsesMethacrylic 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 DescriptionLiquid.

Preparation methods · 1 item

PreparationTo synthesize Methacrylic anhydride, sodium methacrylate (1 mol), propionyl chloride (3 mol), and a polymerization inhibitor (0.1 mol) were added to a reaction kettle. The mixture was heated to 90-100 ℃ and refluxed for 8 hours. Methacrylic anhydride was then obtained by distilling and collecting fractions at 100-105 ℃. The yield of the product was 98.33%.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京科朗科技有限公司025-58748998 18951874644 · [email protected]

Related reactions

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Linked notes

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