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913243

Sigma-Aldrich

Maleic acid

≥99.5% (HPLC), <=0.5% water

Synonym(s):

(2Z)-2-Butenedioic acid, (2Z)-But-2-enedioic acid, Maleinic acid, cis-Butenedioic acid, Toxilic acid

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About This Item

Linear Formula:
HO2CCH=CHCO2H
CAS Number:
Molecular Weight:
116.07
Beilstein:
605762
MDL number:
UNSPSC Code:
12352106
NACRES:
NA.23

Quality Level

description

Residue on Ignition: <= 0.1%

Assay

≥99.5% (HPLC)
≥99.5% anhydrous basis (HPLC)

form

powder

color

white to off-white

mp

130-135 °C (lit.)
137-140 °C (lit)

density

1.59 g/mL at 20 °C (lit.)
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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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 has been reported to have 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 research. Maleic acid based polymer blend were reported to increase the ionic conductivity of PEO basd polymer solid electrolytes by suppressing 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. In this hydrogel system, the uptake of cationic dye increased with an increase of MA content in the AAm/MA hydrogels.

Pictograms

CorrosionExclamation mark

Signal Word

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

WGK

WGK 1


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ultrahigh-Capacity Organic Anode with High-Rate Capability and Long Cycle Life for Lithium-Ion Batteries
Yan W, et al.
ACS Energy Letters, 2(9), 2140-2148 (2017)
Ultrahigh-Capacity Organic Anode with High-Rate Capability and Long Cycle Life for Lithium-Ion Batteries.
Yan W, et al.
ACS Energy Letters, 2(9), 2140-2148 (2017)
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)
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)
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)

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