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Maleic acid

CAS No.
110-16-7
Chemical Name:
Maleic acid
Synonyms
Maleinic acid;(2Z)-But-2-enedioic acid;TOXILIC ACID;DL-Maleic acid;(z)-butenedioicaci;Kyselina maleinova;NA 2215;eic acid;Maleicaci;malenicacid
CBNumber:
CB2852803
Molecular Formula:
C4H4O4
Lewis structure
maleic_acid lewis structure
Molecular Weight:
116.07
MDL Number:
MFCD00063177
MOL File:
110-16-7.mol
Last updated:2024-03-14 15:18:26

Maleic acid Properties

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)
Flash point 127 °C
storage temp. Store below +30°C.
solubility 478.8g/l
pka 1.83(at 25℃)
form Powder/Solid
Specific Gravity 1.59
color White
PH 3.05(1 mM solution);2.21(10 mM solution);1.54(100 mM solution);
Water Solubility 790 g/L (25 ºC)
Merck 14,5703
BRN 605762
Stability Stable. Combustible. Incompatible with strong oxidizing agents, bases.
InChIKey VZCYOOQTPOCHFL-OWOJBTEDSA-N
LogP -1.3 at 20℃
Indirect Additives used in Food Contact Substances MALEIC ACID
FDA 21 CFR 175.105; 177.1200
CAS DataBase Reference 110-16-7(CAS DataBase Reference)
EWG's Food Scores 1-3
FDA UNII 91XW058U2C
NIST Chemistry Reference 2-Butenedioic acid (Z)-(110-16-7)
EPA Substance Registry System Maleic acid (110-16-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07
Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07
Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07
Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07
Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07
Signal word  Danger
Signal word  Danger
Signal word  Danger
Signal word  Danger
Signal word  Danger
Hazard statements  H302+H312-H315-H317-H318-H335
Hazard statements  H302+H312-H315-H317-H318-H335
Hazard statements  H302+H312-H315-H317-H318-H335
Hazard statements  H302+H312-H315-H317-H318-H335
Hazard statements  H302+H312-H315-H317-H318-H335
Precautionary statements  P261-P264-P280-P301+P312-P302+P352+P312-P305+P351+P338
Precautionary statements  P261-P264-P280-P301+P312-P302+P352+P312-P305+P351+P338
Precautionary statements  P261-P264-P280-P301+P312-P302+P352+P312-P305+P351+P338
Precautionary statements  P261-P264-P280-P301+P312-P302+P352+P312-P305+P351+P338
Precautionary statements  P261-P264-P280-P301+P312-P302+P352+P312-P305+P351+P338
Hazard Codes  Xn
Risk Statements  22-36/37/38-43
Safety Statements  26-28-37-28A-46-24
RIDADR  3261
WGK Germany  1
RTECS  OM9625000
TSCA  Yes
HazardClass  8
PackingGroup  III
HS Code  29173990
NFPA 704
1
2 1

Maleic acid price More Price(44)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHL80142 Maleic acid phyproof? Reference Substance 110-16-7 100mg $262 2024-03-01 Buy
Sigma-Aldrich MX0100 Maleic acid 110-16-7 50kg $2720 2024-03-01 Buy
Sigma-Aldrich 8.00380 Maleic acid for synthesis 110-16-7 100g $41.6 2024-03-01 Buy
Sigma-Aldrich 8.00380 Maleic acid for synthesis 110-16-7 500g $45.4 2024-03-01 Buy
Sigma-Aldrich 92816 Maleic acid Standard for quantitative NMR, TraceCERT 110-16-7 1g $208 2024-03-01 Buy
Product number Packaging Price Buy
PHL80142 100mg $262 Buy
MX0100 50kg $2720 Buy
8.00380 100g $41.6 Buy
8.00380 500g $45.4 Buy
92816 1g $208 Buy

Maleic acid Chemical Properties,Uses,Production

Description

Maleic acid 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, also known as maleinic acid and toxilic acid, is a white crystalline (monoclinic) powder and possesses a faint acidulous odor and an astringent taste. It is soluble in water and alcohol. Maleic acid and fumaric 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.

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.

Uses

Maleic acid is used as a precursor to fumaric acid, dimethyl maleate and glyoxalic acid. It is an electrophile and acts as dienophine in Diels-Alder reactions. It reacts with drugs to form more stable addition salts like indacaterol maleate, carfenazine, chlorpheniramine, pyrilamine, methylergonovine and thiethylperazine. Its maleate ion is useful in biochemistry as an inhibitor of transaminase reactions.

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.

Definition

ChEBI: Maleic acid is a butenedioic acid in which the double bond has cis- (Z)-configuration. It has a role as a plant metabolite, an algal metabolite and a mouse metabolite. It is a conjugate acid of a maleate(1-) and a maleate.

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.

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

General Description

Maleic acid is a colorless crystalline solid having a faint odor. Maleic acid is combustible though Maleic acid may take some effort to ignite. Maleic acid is soluble in water. Maleic acid is used to make other chemicals and for dyeing and finishing naturally occurring fibers.

Air & Water Reactions

Soluble in water.

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].

Hazard

Toxic by ingestion.

Health Hazard

Inhalation causes irritation of nose and throat. Contact with eyes or skin causes irritation.

Fire Hazard

Special Hazards of Combustion Products: Irritating smoke containing maleic anhydride may form in fire.

Flammability and Explosibility

Non flammable

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 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.

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

Potential Exposure

Maleic acid is used to make artificial resins, antihistamines, and to preserve (retard rancidity) of fats and oils

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least30 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. If victim is conscious, administer water ormilk. Do not induce vomiting. Medical observation isrecommended for 24°48 h after breathing overexposure, aspulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consideradministering a corticosteroid spray.

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.

Shipping

UN2215 Maleic acid, Hazard class: 8; Labels: 8-Corrosive material.

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.]

Incompatibilities

Maleic acid can react with oxidizing materials. Aqueous solutions are corrosive to carbon steels.

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

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

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.

142-45-0
110-16-7
Synthesis of Maleic acid from Acetylenedicarboxylic acid
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View Lastest Price from Maleic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Maleic acid pictures 2024-03-28 Maleic acid
110-16-7
US $2.00 / KG 1KG 99% 1000mt/year Jinan Finer Chemical Co., Ltd
Maleic acid pictures 2023-12-29 Maleic acid
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US $0.00 / kg 1kg 99% 1000000 Hebei Jingbo New Material Technology Co., Ltd
Maleic acid pictures 2023-12-24 Maleic acid
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US $50.00-1.00 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
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  • Maleic acid
    110-16-7
  • US $2.00 / KG
  • 99%
  • Jinan Finer Chemical Co., Ltd
  • Maleic acid pictures
  • Maleic acid
    110-16-7
  • US $0.00 / kg
  • 99%
  • Hebei Jingbo New Material Technology Co., Ltd
  • Maleic acid pictures
  • Maleic acid
    110-16-7
  • US $50.00-1.00 / KG
  • 99%
  • Henan Fengda Chemical Co., Ltd
1,2-Ethylenedicarboxylic acid, (Z) 1,2-ethylenedicarboxylicacid,(z) 2-Butenedioicacid(Z)- acidemaleique Butenedioic acid,(Z)- cis-Ethylene-1,2-dicar-boxylicacid kyselinamaleinova maleinicacid Malenic acid malenicacid NA 2215 (z)-2-butenedioicaci (z)-2-butenedioicacid MALEIC ACID FOOD GRADE TIMOLOL MALEATE ACID MALEIC ACID 500MG NEAT MALEIC ACID, PH EUR MALEIC ACID, REAGENTPLUS(R) MALEIC ACID, EP STANDARD MALEIC ACID, EXTRA PURE BP USP 99+% MALEIC ACID, 99+% MALEIC ACID, GR 99.5+% MALEIC ACID, USP STANDARD MaleicAcidGr MaleicAcidBp MaleicAcidForSynthesis 2-Butenedioic acid (2Z)- MALEIC ACID(RG) [[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate Maleic acid, 98+% DL-MALIC ACID pure MALEIC ACID extrapure AR cis-Butenedioic acid, Acidum maleicum, Toxilic acid 1-(2-azabicyclo[5.4.0]undeca-8,10,12-trien-10-yl)-3-(1-benzyl-4-piperidyl)propan-1-one (Z)-but-2-enedioic acid Maleic acid, extra pure, Ph Eur, BP Maleic Acid (300 mg) MALEIC ACID, WHITE (2Z)-But-2-ene-1,4-dioic acid Maleic acid, 99% 100GR Maleic acid, 99% 1KG Maleicaci Maleic acid 0 Maleic acid ReagentPlus(R), >=99.0% (HPLC) Maleic acid Vetec(TM) reagent grade, 98% Z-BUTENEDIOIC ACID (2Z)-2-Butenedioic acid (z)-1,2-ethylenedicarboxylicacid (Z)-2-Butenedioic acid AKOS BBS-00003804 ACIDUM MALEICUM BUFFER, MALEIC ACID, PH 2.35 CIS-1,2-ETHYLENEDICARBOXYLIC ACID CIS-2-BUTENEDIOIC ACID CIS-BUTENEDIODIC ACID CIS-BUTENEDIOIC ACID MALEIC ACID eic acid