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M188

Sigma-Aldrich

Maleic anhydride

99%

Synonym(s):

2,5-Furandione

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About This Item

Empirical Formula (Hill Notation):
C4H2O3
CAS Number:
108-31-6
Molecular Weight:
98.06
Beilstein/REAXYS Number:
106909
EC Number:
203-571-6
MDL number:
MFCD00005518
UNSPSC Code:
12162002
PubChem Substance ID:
24896701
NACRES:
NA.23

vapor density

3.4 (vs air)

vapor pressure

0.16 mmHg ( 20 °C)

assay

99%

autoignition temp.

870 °F

expl. lim.

7.1 %

bp

200 °C (lit.)

mp

51-56 °C (lit.)

SMILES string

O=C1OC(=O)C=C1

InChI

1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H

InChI key

FPYJFEHAWHCUMM-UHFFFAOYSA-N

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General description

Maleic anhydride (MA) belongs to the class of monomers known as cyclic dicarboxylic anhydrides. It is commonly used in polymerization reactions to produce various types of polymers such as poly(maleic anhydride) (PMA), maleic anhydride-based resins, and maleic anhydride-butadiene copolymers (MABS), etc. These MA-based polymers find applications in various fields including, polymer blends and coatings, epoxy resins, semiconductor devices, secondary batteries, lithium-ion batteries, resin films, glass fiber, coatings, packaging, water treatment, and drug delivery systems. Additionally, MA can be grafted onto other polymers, to enhance their performance and compatibility with other materials. Grafted polymers find applications in the automotive, packaging, and construction industries. Maleic anhydride is also used as an electron-acceptor monomer in the development of various antimicrobial polymers due to their reactive double bonds and reactive anhydride groups.

The structure of maleic acid consists of four carbon molecules along with carboxylate groups on either ends, with a double bond between the central carbon atoms. The anhydride of maleic acid has five atoms in its cyclic molecule, the unsaturated bond undergoes free radical polymerization in the presence of an initiator.

Application

Maleic anhydride can be used as a monomer:
  • In the grafting process of high-density polyethylene (HDPE) by the monomer microencapsulation technique, which enables the introduction of enhanced functionality and improved properties to the polymer for functional coatings, membranes, or surface treatments, adhesives, and coatings.
  • In the functionalization of polylactic acid (PLA) and acts as a coupling agent in natural fiber biocomposites. The functionalization improves the compatibility and interfacial adhesion between PLA and natural fibers, leading to enhanced mechanical properties and expanded applications of the resulting biocomposite materials.
  • Maleic anhydride may be used in the synthesis of unsaturated polyester resins and as a reactant in synthesizing important products such as agricultural chemicals, lubricant additives, and food acidulatents.

Physical form

briquettes

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1A - STOT RE 1 Inhalation

target_organs

Respiratory system

supp_hazards

EUH071

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 1

flash_point_f

217.4 °F - closed cup

flash_point_c

103 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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João F A Silva et al.
Polymers, 12(6) (2020-06-18)
Titanium dioxide is considered the most efficient white pigment for opacification of thermoplastics. However, its high cost, combined with strong price oscillations due to production bottlenecks, has been driving the industry towards alternatives that might allow reducing the titanium dioxide
Veronika Bátori et al.
Polymers, 11(3) (2019-04-10)
This study was conducted to improve the properties of thin films prepared from orange waste by the solution casting method. The main focus was the elimination of holes in the film structure by establishing better cohesion between the major cellulosic
Sylwia Członka et al.
Materials (Basel, Switzerland), 13(7) (2020-04-16)
In this work, rigid polyurethane (PUR) foams were prepared by incorporating 2 wt% of eucalyptus fibers. The eucalyptus fibers were surface-modified by maleic anhydride, alkali, and silane (triphenylsilanol) treatment. The impact of the modified eucalyptus fibers on the mechanical, thermal
Eunice Cunha et al.
Nanomaterials (Basel, Switzerland), 8(9) (2018-09-12)
The search for graphene or few-layer graphene production methods that are simple, allow mass production, and yield good quality material continues to provoke intense investigation. The present work contributes to this investigation through the study of the aqueous exfoliation of
Frita Yuliati et al.
Polymers, 12(8) (2020-08-06)
Low cross-link density thermally reversible networks were successfully synthesized from jatropha and sunflower oils. The oils were epoxidized and subsequently reacted with furfurylamine to attach furan groups onto the triglycerides, preferably at the epoxide sites rather than at the ester
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