Merck
All Photos(4)

M0375

Sigma-Aldrich

Maleic acid

ReagentPlus®, ≥99% (HPLC)

Synonym(s):
Toxilic acid, cis-Butenedioic acid
Linear Formula:
HO2CCH=CHCO2H
Molecular Weight:
116.07
Beilstein:
605762
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

product line

ReagentPlus®

assay

≥99% (HPLC)

form

powder

impurities

≤2.0% water

ign. residue

≤0.1%

pKa (25 °C)

(1) 1.97, (2) 6.24

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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General description

Maleic acid (MA) is a dicarboxylic acid that undergoes esterification with ethanol in the presence of cation-exchange resin catalysts to form diethyl maleate. Its crystalline structure has been analyzed. Reaction kinetics and mechanism of the isomerization of maleic acid to fumaric acid in the presence of ceric and bromide ions has been investigated. The reaction mechanism and reactivity ratios for the radical copolymerization of maleic acid with styrene have been determined.

Application

Maleic acid has been used in the preparation of tris-maleate buffer and sodium maleate buffer. It has also been used for the pretreatment of poplar tracheid cell walls for the spectroscopic analysis of lignin. It may be used to synthesize superswelling acrylamide/maleic acid hydrogels.

Packaging

25 kg in poly drum
1 kg in poly bottle
100, 500 g in poly bottle

Quality

Repurified

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 1

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Esterification of maleic acid with ethanol over cation-exchange resin catalysts.
Yadav GD and Thathagar MB.
Reactive functional Polymers, 52(2), 99-110 (2002)
Swelling equilibria and dye adsorption studies of chemically crosslinked superabsorbent acrylamide/maleic acid hydrogels.
Karadag E, et al.
Eur. Polymer J., 38(11), 2133-2141 (2002)
Determination of total dietary fibre and available carbohydrates: A rapid integrated procedure that simulates in vivo digestion.
McCleary BV, et al.
Starch, 67(9-10), 860-883 (2015)
Bromine-Catalyzed Isomerization of Maleic Acid to Fumaric Acid.
Jwo JJ.
J. Chin. Chem. Soc., 28(1), 34-41 (1981)
A refinement of the crystal structure of maleic acid.
James MNG and Williams GJB.
Acta Crystallographica Section B, Structural Science, 30(5), 1249-1257 (1974)

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