Maleinsäure

Bezeichnung:Maleinsäure

CAS-Nr110-16-7

Englisch Name:Maleic acid

CBNumberCB2852803

SummenformelC4H4O4

Molgewicht116.07

MOL-Datei110-16-7.mol

Synonyma

Maleinsaeure

Maleinsäure

(Z)-Butendis?ure

Maleinsäure physikalisch-chemischer Eigenschaften

Schmelzpunkt	130-135 °C (lit.)
Siedepunkt	275°C
Dichte	1.59 g/mL at 25 °C (lit.)
Dampfdruck	0.001Pa at 20℃
Brechungsindex	1.5260 (estimate)
Flammpunkt	127 °C
storage temp.	Store below +30°C.
Löslichkeit	478.8g/l
pka	1.83(at 25℃)
Aggregatzustand	Powder/Solid
Wichte	1.59
Farbe	White
PH	3.05(1 mM solution);2.21(10 mM solution);1.54(100 mM solution);
Wasserlöslichkeit	790 g/L (25 ºC)
Merck	14,5703
BRN	605762
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents, bases.
InChIKey	VZCYOOQTPOCHFL-OWOJBTEDSA-N
LogP	-1.3 at 20℃
CAS Datenbank	110-16-7(CAS DataBase Reference)
NIST chemische Informationen	2-Butenedioic acid (Z)-(110-16-7)
EPA chemische Informationen	Maleic acid (110-16-7)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38-43
S-Sätze:	26-28-37-28A-46-24
RIDADR	3261
WGK Germany	1
RTECS-Nr.	OM9625000
TSCA	Yes
HazardClass	8
PackingGroup	III
HS Code	29173990
Giftige Stoffe Daten	110-16-7(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Maleic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
WEISSE KRISTALLE.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen und Verbrennen unter Bildung stark reizender Rauche mit Maleinanhydrid. Mittelstarke Säure in wässriger Lösung.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation und durch Verschlucken.
INHALATIONSGEFAHREN
Verdampfung bei 20°C vernachlässigbar; eine gesundheitsschädliche Partikelkonzentration in der Luft kann jedoch beim Dispergieren schnell erreicht werden, vor allem als Pulver.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt stark die Augen, die Haut und die Atemwege.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann Dermatitis hervorrufen. Möglich sind Auswirkungen auf die Nieren.
LECKAGE
NICHT in die Kanalisation spülen. Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste mit viel Wasser wegspülen. Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S37:Geeignete Schutzhandschuhe tragen.
Aussehen Eigenschaften
C4H4O4; cis-Butendisäure. Farbloser, feinkristalliner Feststoff mit säuerlichem Geruch.
Gefahren für Mensch und Umwelt
Gesundheitsschädlich beim Verschlucken. Reizt die Atmungswege, Augen und die Haut.

LD₅₀ (oral, Ratte): 708 mg/kg
Schutzmaßnahmen und Verhaltensregeln
Geeignete Schutzhandschuhe als kurzzeitiger Staubschutz.
Verhalten im Gefahrfall
Trocken aufnehmen. Der Entsorgung zuführen.
Kohlendioxid, Wasser, Pulver.
Brennbar.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft. Arzt hinzuziehen.
Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminerte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Gelöst in z.B. Ethanol als halogenfreie, organische Lösemittelabfälle.
Beschreibung
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.
Chemische Eigenschaften
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.
Physikalische Eigenschaften
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.
Verwenden
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.
Vorbereitung Methode
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.
Reaktionen
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
Allgemeine Beschreibung
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 Reaktionen
Soluble in water.
Reaktivität anzeigen
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.
Brandgefahr
Special Hazards of Combustion Products: Irritating smoke containing maleic anhydride may form in fire.
Flammability and Explosibility
Non flammable
Pharmazeutische Anwendungen
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.
Sicherheitsprofil
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.
Sicherheit(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
mögliche Exposition
Maleic acid is used to make artificial resins, antihistamines, and to preserve (retard rancidity) of fats and oils
Erste Hilfe
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.
Lager
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.
Versand/Shipping
UN2215 Maleic acid, Hazard class: 8; Labels: 8-Corrosive material.
läuterung methode
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.]
Inkompatibilitäten
Maleic acid can react with oxidizing materials. Aqueous solutions are corrosive to carbon steels.
Inkompatibilitäten
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.

Maleic acid Upstream-Materialien And Downstream Produkte

Maleinsäure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

110-16-7, Maleic acid Verwandte Suche:

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