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912735

Sigma-Aldrich

Maleic acid

electronic grade, ≥99.97% trace metals basis, water <=350 ppm

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Synonym(s):
(2Z)-2-Butenedioic acid, (2Z)-But-2-enedioic acid, Maleinic acid, cis-Butenedioic acid, Toxilic acid
Linear Formula:
HO2CCH=CHCO2H
CAS Number:
Molecular Weight:
116.07
Beilstein/REAXYS Number:
605762
MDL number:

grade

electronic grade

Quality Level

assay

≥99.97% trace metals basis

form

powder

color

white to off-white

mp

130-135 °C (lit.)

density

1.59 g/mL at 25 °C (lit.)

SMILES string

OC(=O)\C=C/C(O)=O

InChI

1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-

InChI key

VZCYOOQTPOCHFL-UPHRSURJSA-N

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1 of 4

This Item
PHR1272MX0100PHL80142
vibrant-m

912735

Maleic acid

vibrant-m

PHR1272

Maleic acid

vibrant-m

MX0100

Maleic acid

vibrant-m

PHL80142

Maleic acid

Quality Level

100

Quality Level

300

Quality Level

100

Quality Level

-

grade

electronic grade

grade

certified reference material, pharmaceutical secondary standard

grade

-

grade

primary reference standard

form

powder

form

-

form

crystalline powder

form

powder

mp

130-135 °C (lit.)

mp

130-135 °C (lit.)

mp

130-135 °C (lit.)

mp

130-135 °C (lit.)

density

1.59 g/mL at 25 °C (lit.)

density

1.59 g/mL at 25 °C (lit.)

density

1.59 g/mL at 25 °C (lit.)

density

1.59 g/mL at 25 °C (lit.)

General description

Maleic acid is the cis-isomer of butenedioic acid, an unsaturated organic dibasic acid. Maleic acid shows reactions typical of both olefins and carboxylic acids. Commercially important reactions of the acid groups include esterification with glycols to polyesters and dehydration to the anhydride. The double bond is involved in conversions to fumaric acid, to sulfosuccinic acid, and to Malathion.

Application

Maleic acid has been adopted as a high performance organic anode material for lithium ion batteries. In one study, it showed an ultrahigh reversible capacity of ca. 1500 mAhg–1 at 46.2 mAg–1 current density, and a relatively high capacity of 570.8 mAhg–1 at current density of 46.2 Ag–1. When cycled at high current density of 2.31 Ag–1, a capacity retention of 98.1% was obtained after 500 cycles.
Maleic acid has been used in constructing polymeric solid electrolytes for battery and fuel cell. In one study, it was showen that maleic acid based polymer blend helps increasing the ionic conductivity of PEO basd polymer solid electrolytes by suppressing its crystallization.
Maleic acid has also been used to make superswelling acrylamide (AAm)/maleic acid (MA) hydrogels by free radical polymerization in aqueous solution of AAm with MA as comonomer with some multifunctional crosslinkers such as trimethylolpropane triacrylate and 1,4-butanediol dimethacrylate. When the uptake of cationic dye was studied, it was shown that the binding ratio of hydrogel/dye systems was gradually increased with the increase of MA content in the AAm/MA hydrogels.

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 1


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Ultrahigh-Capacity Organic Anode with High-Rate Capability and Long Cycle Life for Lithium-Ion Batteries
Wang Y, et al.
ACS Energy Letters, 2(9), 2140-2148 (2017)
A polymeric solid electrolyte based on a binary blend of poly(ethylene oxide), poly(methyl vinyl ether-maleic acid) and LiClO4
Rocco A M, et al.
Polymer, 43(13), 3601-3609 (2002)
Swelling equilibria and dye adsorption studies of chemically crosslinked superabsorbent acrylamide/maleic acid hydrogels
Karadag E, et al.
European Polymer Journal, 38(11), 2133-2141 (2002)

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