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Merck

276685

Methacrylic anhydride

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

Sinônimo(s):

Methacrylic acid anhydride

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Sobre este item

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

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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

Quality Level

200

bp

87 °C/13 mmHg (lit.)

density

1.035 g/mL at 25 °C (lit.)

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1 of 4

Este Item
1557218.00578125733
Methacrylic anhydride contains 2,000 ppm topanol A as inhibitor, ≥98%

Sigma-Aldrich

276685

Methacrylic anhydride

Methacrylic acid contains 250 ppm MEHQ as inhibitor, 99%

Sigma-Aldrich

155721

Methacrylic acid

Methacrylic acid (stabilised with hydroquinone monomethyl ether) for synthesis

Sigma-Aldrich

8.00578

Methacrylic acid

Phthalic anhydride ReagentPlus®, 99%

Sigma-Aldrich

125733

Phthalic anhydride

assay

≥98%

assay

99%

assay

≥99% (GC)

assay

99%

density

1.035 g/mL at 25 °C (lit.)

density

1.015 g/mL at 25 °C (lit.)

density

1.015 g/cm3 at 20 °C

density

-

contains

2,000 ppm topanol A as inhibitor

contains

250 ppm MEHQ as inhibitor

contains

-

contains

-

refractive index

n20/D 1.453 (lit.)

refractive index

n20/D 1.431 (lit.)

refractive index

-

refractive index

-

bp

87 °C/13 mmHg (lit.)

bp

163 °C (lit.)

bp

161 °C/1013 hPa

bp

284 °C (lit.)

form

liquid

form

liquid

form

liquid

form

flakes

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
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

Classe de armazenamento

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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Certificados de análise (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)
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)
Avathamsa Athirasala et al.
Scientific reports, 7(1), 3323-3323 (2017-06-14)
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
Tian-Tian Yao et al.
Journal of materials chemistry. B, 7(33), 5089-5095 (2019-08-23)
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
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
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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