| Identification | More | [Name]
Maleic acid | [CAS]
110-16-7 | [Synonyms]
ACIDUM MALEICUM
AKOS BBS-00003804
BUFFER, MALEIC ACID, PH 2.35
BUTENEDIOIC ACID
CIS-1,2-ETHYLENEDICARBOXYLIC ACID
CIS-2-BUTENEDIOIC ACID
CIS-BUTENEDIODIC ACID
CIS-BUTENEDIOIC ACID
MA
MALEIC ACID
TOXILIC ACID
Z-BUTENEDIOIC ACID
(2Z)-2-Butenedioic acid
(z)-1,2-ethylenedicarboxylicacid
(Z)-2-Butenedioic acid
(z)-2-butenedioicaci
(z)-2-butenedioicacid
(z)-butenedioicaci
1,2-Ethylenedicarboxylic acid, (Z)
1,2-ethylenedicarboxylicacid,(z) | [EINECS(EC#)]
203-742-5 | [Molecular Formula]
C4H4O4 | [MDL Number]
MFCD00063177 | [Molecular Weight]
116.07 | [MOL File]
110-16-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Maleic acid is a white crystalline solid. Faint,
acid like odor. | [Melting point ]
130-135 °C (lit.) | [Boiling point ]
275°C | [density ]
1.59 g/mL at 25 °C(lit.)
| [vapor pressure ]
0.001Pa at 20℃ | [refractive index ]
1.5260 (estimate) | [Fp ]
127 °C
| [storage temp. ]
Store at RT. | [solubility ]
478.8g/l | [form ]
Powder/Solid | [pka]
1.83(at 25℃) | [color ]
White | [Specific Gravity]
1.59 | [PH]
1.3 (100g/l, H2O, 20℃) | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents, bases. | [Water Solubility ]
790 g/L (25 ºC) | [Merck ]
14,5703 | [BRN ]
605762 | [InChIKey]
VZCYOOQTPOCHFL-OWOJBTEDSA-N | [LogP]
-1.3 at 20℃ | [Uses]
Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis.
Maleic acid may be used to form acid addition salts with drugs to make them more stable, such as indacaterol maleate. | [CAS DataBase Reference]
110-16-7(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Butenedioic acid (Z)-(110-16-7) | [EPA Substance Registry System]
Maleic acid (110-16-7) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S37:Wear suitable gloves . | [RIDADR ]
3261 | [WGK Germany ]
1
| [RTECS ]
OM9625000
| [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29171900 | [Safety Profile]
Moderately toxic by
ingestion and skin contact. Passes through
intact skin. A skin and severe eye irritant and
a corrosive. Believed to be more toxic than
its isomer, fumeric acid. Combustible when
exposed to heat or flame. When heated to
decomposition it emits acrid smoke and
irritating fumes. | [Hazardous Substances Data]
110-16-7(Hazardous Substances Data) |
| Hazard Information | Back Directory | [General Description]
MALEIC ACID(110-16-7) is a colorless crystalline solid having a faint odor. MALEIC ACID(110-16-7) is combustible though MALEIC ACID(110-16-7) may take some effort to ignite. MALEIC ACID(110-16-7) is soluble in water. MALEIC ACID(110-16-7) is used to make other chemicals and for dyeing and finishing naturally occurring fibers. | [Reactivity Profile]
MALEIC ACID is a colorless to white crystalline solid. Moderately toxic. When heated to decomposition MALEIC ACID emits irritating fumes and acrid smoke [Lewis, 3rd ed., 1993, p. 790]. | [Air & Water Reactions]
Soluble in water. | [Hazard]
Toxic by ingestion. | [Health Hazard]
Inhalation causes irritation of nose and throat. Contact with eyes or skin causes irritation. | [Potential Exposure]
Maleic acid is used to make artificial
resins, antihistamines, and to preserve (retard rancidity) of
fats and oils | [Fire Hazard]
Special Hazards of Combustion Products: Irritating smoke containing maleic anhydride may form in fire. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
30 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get
medical attention. If victim is conscious, administer water
or milk. Do not induce vomiting. Medical observation is
recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for
pulmonary edema, a doctor or authorized paramedic may
consider administering a drug or other inhalation therapy. | [Shipping]
UN2215 Maleic acid, Hazard class: 8; Labels:
8-Corrosive material. | [Incompatibilities]
Dust may form explosive mixture with
air, Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine,
fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases, amines,
reducing agents; alkali metals | [Description]
Maleic acid (cas: 110-16-7) is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCHCHCO2H. Maleic acid is the cis-isomer of butenedioic acid, where as fumaric acid is the trans-isomer. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few applications.
| [Chemical Properties]
Maleic acid is a white crystalline solid. Faint,
acid like odor. | [Chemical Properties]
Maleic acid occurs as a white crystalline (monoclinic) powder and
possesses a faint acidulous odor and an astringent taste.
Fumaric acid and maleic acid are the simplest unsaturated
carboxylic diacids. These acids experience two-step dissociation in
aqueous solutions.They have the same structural formula but
different spatial configurations. Fumaric acid is the trans and maleic
acid the cis isomer. The physical properties of maleic acid and
fumaric acid are very different. The cis isomer is less stable. Maleic
acid is used in the preparation of fumaric acid by catalytic
isomerization. | [Chemical Properties]
Maleic acid, HOOCCH:CHCOOH, also known as maleinic acid and toxilic acid,is a colorless crystalline dibasic acid. It is soluble in water and alcohol. Maleic acid is used in manufacturing synthetic resins, in textile processing, and in preserving oils and fats.
| [Waste Disposal]
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed. Liquid: incinerate after mixing with a flammable
solvent. Use afterburner for complete combustion. Solid:
dissolve in a flammable solvent or package in paper and
burn. See above | [Physical properties]
Maleic acid is a less stable molecule than fumaric acid. The difference in heat of combustion is 22.7 kJ·mol?1. The heat of combustion is -1355 kJ / mole. Maleic acid is more soluble in water than fumaric acid. The melting point of maleic acid (135 °C) is also much lower than that of fumaric acid (287 °C). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place in maleic acid at the expense of intermolecular interactions, and that are not possible in fumaric acid for geometric reasons. | [Application]
Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. It may be used to form acid addition salts with drugs to make them more stable, such as indacaterol maleate. Maleic acid is also used in manufacturing synthetic resins; in textile processing; in preserving oils and fats; to retard rancidity of fats and oils in 1:10,000 (these are said to keep 3 times longer than those without the acid); dyeing and finishing wool, cotton, and silk; preparing the maleate salts of antihistamines and similar drugs. | [Definition]
ChEBI: A butenedioic acid in which the double bond has cis- (Z)-configuration. | [Production Methods]
Maleic anhydride is the main source of maleic acid produced by
hydration. Maleic anhydride is prepared commercially by the
oxidation of benzene or by the reaction of butane with oxygen in the
presence of a vanadium catalyst. | [Reactions]
Although not practised commercially, maleic acid can be converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation (ethanol / palladium on carbon). It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid, being electrophilic, participates as a dienophile in many Diels - Alder reactions. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 86, p. 4603, 1964 DOI: 10.1021/ja01075a017
The Journal of Organic Chemistry, 60, p. 6676, 1995 DOI: 10.1021/jo00126a013
Organic Syntheses, Coll. Vol. 2, p. 302, 1943 | [Flammability and Explosibility]
Nonflammable | [Pharmaceutical Applications]
Maleic acid is used in the pharmaceutical industry as a pH modifier
and a buffering agent.It is also used to prevent rancidity of oils
and fats; a ratio of 1 : 10 000 is usually sufficient to retard rancidity.
Maleic acid is commonly used as a pharmaceutical intermediate to
form the maleate salts of several categories of therapeutic agents,
such as salts of antihistamines and other drug substances. | [Safety]
Maleic acid is generally regarded as a nontoxic and nonirritant
material when used at low levels as an excipient. Maleic acid is used
in oral, topical, and parenteral pharmaceutical formulations in
addition to food products.
LD50 (mouse, oral): 2.40g/kg(7)
LD50 (rabbit, skin): 1.56g/kg
LD50 (rat, oral): 0.708g/kg | [Carcinogenicity]
In chronic feeding studies, 12
Osborne–Mendel rats per group were fed 0.5, 1.0, or 1.5%
maleic acid in their diets for 2 years. Concentrations of 1.0
and 1.5% maleic acid retarded the growth rate of rats, and
all concentrations of maleic acid increased mortality rate;
no tumorigenesis was reported. Toxicological differences
from controls were not marked, and the pathology was
nonspecific. | [storage]
Maleic acid converts into the much higher-melting fumaric acid
(mp: 287°C) when heated to a temperature slightly above its melting
point.
Maleic acid is combustible when exposed to heat or flame. The
bulk material should be stored in airtight glass containers and
protected from light. It is recommended not to store it above 25°C. | [Purification Methods]
Crystallise the acid from acetone/pet ether (b 60-80o) or hot water. Dry it at 100o. [Beilstein 2 H 748, 2 I 303, 2 II 641, 2 III 1911, 2 IV 2199.] | [Regulatory Status]
Included in the FDA Inactive Ingredients Database (IM and IV
injections; oral tablets and capsules; topical applications). Included
in nonparenteral and parenteral medicines licensed in the UK. |
|
|