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Merck
CN

276685

Methacrylic anhydride

contains 2,000 ppm topanol A as inhibitor, ≥98%

Synonym(s):

Methacrylic acid anhydride

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About This Item

Linear Formula:
[H2C=C(CH3)CO]2O
CAS Number:
760-93-0
Molecular Weight:
154.16
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
24856712
MDL number:
MFCD00008586
Beilstein/REAXYS Number:
1761982

Key Documents

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Product Name

Methacrylic anhydride, contains 2,000 ppm topanol A as inhibitor, ≥98%

InChI

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

SMILES string

CC(=C)C(=O)OC(=O)C(C)=C

InChI key

DCUFMVPCXCSVNP-UHFFFAOYSA-N

assay

≥98%

form

liquid

contains

2,000 ppm topanol A as inhibitor

refractive index

n20/D 1.453 (lit.)

bp

87 °C/13 mmHg (lit.)

density

1.035 g/mL at 25 °C (lit.)

Quality Level

200

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Application

Methacrylic anhydride can be used as a starting material to synthesize:
  • Methacrylated chondroitin sulfate pH-sensitive hydrogels by copolymerization reaction. These hydrogels can be used in drug delivery systems.
  • High-performance lignin-based thermosets.
  • Gel polymer electrolyte, which is then integrated with the cathode to form high-performance lithium-ion batteries.
Methacrylic anhydride can be also used as a precursor to synthesize bio-renewable resins for composite applications. For example, it can be used to prepare soybean oil and a eugenol-based resin system. This resin possesses high thermal stability, and good mechanical properties, which makes it a suitable matrix for the pultrusion process.

General description

Methacrylic anhydride is an organic compound derived from methacrylic acid, which belongs to the class of acrylic acids. It is primarily employed as a monomer in the production of polymers, particularly poly(methacrylic acid) and its copolymers. These polymers find applications in a wide range of industries, including bio-renewable resins, pH-sensitive hydrogels, thermosets, coatings, adhesives, and plastics, due to their excellent chemical and thermal stability. In the polymerization of methacrylic anhydride, the most common inhibitor used is Topanol A. It is typically added in small quantities (2,000 ppm) to hinder undesirable side reactions during the polymerization, ensuring controlled and high-quality polymer formation.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

183.2 °F - closed cup

flash_point_c

84 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB4745
SDBB0992
STBL0281
STBL0280
STBK9909

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Notes-Acrylic and Methacrylic Anhydrides.
Brotherton T, et al.
The Journal of Organic Chemistry, 26(4), 1283-1284 (1961)
A I Van Den Bulcke et al.
Biomacromolecules, 1(1), 31-38 (2001-11-17)
Dynamic shear oscillation measurements at small strain were used to characterize the viscoelastic properties and related differences in the molecular structure of hydrogels based on gelatin methacrylamide. Gelatin was derivatized with methacrylamide side groups and was subsequently cross-linked by radical
G Bahcecioglu et al.
Biomaterials, 218, 119361-119361 (2019-07-25)
A PCL/hydrogel construct that would mimic the structural organization, biochemistry and anatomy of meniscus was engineered. The compressive (380 ± 40 kPa) and tensile modulus (18.2 ± 0.9 MPa) of the PCL scaffolds were increased significantly when constructs were printed with a shifted design and circumferential
Kunyu Zhang et al.
Materials science & engineering. C, Materials for biological applications, 103, 109835-109835 (2019-07-28)
Hydrogels are promising soft materials for the delivery of therapeutic cells and cargo molecules. Inspired by mussel adhesion chemistry, hydrogels based on catechol (Cat)-modified polysaccharides have been developed to enhance hydrogel-tissue interactions. However, due to the inevitable side reactions such
Cyclopolymerization. IV. Structure of polymethacrylic anhydride and kinetics of polymerization of methacrylic anhydride.
Smets G, et al.
Journal of Polymer Science: Part A, General Papers, 2(11), 4825-4834 (1964)
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