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Sigma-Aldrich

Methacrylic anhydride

contains 2,000 ppm topanol A as inhibitor, ≥94%

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Synonym(s):
Methacrylic acid anhydride
Linear Formula:
[H2C=C(CH3)CO]2O
CAS Number:
Molecular Weight:
154.16
Beilstein:
1761982
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

Quality Level

Assay

≥94%

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.)

SMILES string

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

InChI

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

InChI key

DCUFMVPCXCSVNP-UHFFFAOYSA-N

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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.

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.

Pictograms

CorrosionExclamation mark

Signal Word

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

WGK

WGK 2

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Notes-Acrylic and Methacrylic Anhydrides.
Brotherton T, et al.
The Journal of Organic Chemistry, 26(4), 1283-1284 (1961)
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The aim of this study was to design a dermal substitute containing adipose derived stem cells (ADSC) that can be used to improve the regeneration of skin on difficult wound beds by stimulating rapid neovascularization. This was achieved by first
Avathamsa Athirasala et al.
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The requirement for immediate vascularization of engineered dental pulp poses a major hurdle towards successful implementation of pulp regeneration as an effective therapeutic strategy for root canal therapy, especially in adult teeth. Here, we demonstrate a novel strategy to engineer
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)
Tian-Tian Yao et al.
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In the "post-antibiotic era", healthcare-associated infection has become a global problem that threatens public health and causes huge economic losses. The development of antibacterial coatings based on non-antibiotic strategies is particularly important as drug-resistant bacteria continue to evolve. Photodynamic coatings

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