Maleinsäureanhydrid Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSEODER WEISSE KRISTALLE MIT STECHENDEM GERUCH.
CHEMISCHE GEFAHREN
Mittelstarke Säure in wässriger Lösung. Reagiert mit starken Basen und starken Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV: 0.1 ppm (als TWA); Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); Sensibilisierung; (ACGIH 2005).
MAK: 0.1 ppm, 0.41 mg/m? Sensibilisierung der Atemwege und der Haut; Spitzenbegrenzung: überschreitungsfaktor I(1); Schwangerschaft: Gruppe C; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation des Aerosols, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C kann schnell eine gesundheitsschädliche Kontamination der Luft eintreten.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz reizt stark die Augen, die Haut und die Atemwege. Inhalation der Substanz kann zu asthmaähnlichen Reaktionen führen.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Kontakt kann zu Hautsensibilisierung führen. Wiederholte oder andauernde Inhalation kann asthmatische Beschwerden hervorrufen.
LECKAGE
Persönliche Schutzausrüstung: Atemschutzgerät, P3-Filter für giftige Partikel. Chemikalienschutzanzug. Gesichtsschutz benutzen. Hitzeisolierende Schutzhandschuhe (s. Anm.). Verschüttetes Material in abgedeckten Behältern sammeln.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R34:Verursacht Verätzungen.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Aussehen Eigenschaften
C4H2O3; (cis-Butendicarbonsäureanhydrid, cis-Ethylendicarbonsäureanhydrid, Dioxox-2,5-dihydrofuran, 2,5-Dihydrofurandion, 2,5-Furandion, MSA). Farblose bis weiße Nadeln oder Schuppen mit durchdringend scharfem Geruch.
Gefahren für Mensch und Umwelt
Mit Wasser regiert Maleinsäureanhydrid unter Bildung der ätzend wirkenden Maleinsäure. Staubexplosion, auch als Folge elektrostatischer Aufladung, ist möglich. Maleinsäure ist brennbar.
Starke Reizungen nach Augen- und Hautkontakt. Schleimhautreizungen,Husten und Atemnot nach Einatmen. Sensibilisierung mit allergischen Manifestationen bei empfindlichen Personen. Nach Aufnahme größerer Mengen: Toxische Wirkung auf Lunge und Nieren. Weitere gefährliche Reaktionen können nicht ausgeschlossen werden.
Schwach wassergefährdender Stoff (WGK 1).
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe nur als kurzfristiger Staub- und Spritzschutz.
Verhalten im Gefahrfall
Substanz trocken aufnehmen. Mit viel Wasser nachwaschen.
Wassernebel, Kohlendioxid Löschpulver, Schaum.
Erste Hilfe
Nach Hautkontakt: Mit viel Wasser abwaschen.
Nach Augenkontakt: Mit viel Wasser bei geöffnetem Lidspalt mindestens 10 Min. spülen. Augenarzt konsultieren.
Nach Einatmen: Frischluft.
Nach Verschlucken: Viel Wasser trinken lassen. Kein Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort ausziehen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als Sondermüll entsorgen.
Beschreibung
Maleic Anhydride (MAN) is an organic compound with the chemical formula C4H203. It is the acid anhydride of maleic acid and in its pure state it is a colourless or white solid with an acrid odour. Maleic anhydride is truly a remarkable molecule in that it possesses two types of chemical functionality making it uniquely useful in chemical synthesis and applications.
Maleic Anhydride is a multifunctional chemical intermediate with applications in several fields of chemical industry. Its major end use is as feedstock in the production of unsaturated polyester resins (UPR).
These resins are used both in glass-reinforced and in unreinforced applications. The UPR end uses includes a wide range of applications in construction, marine and automobile industries.
In addition, Maleic Anhydride can also be used as raw material in the production of 1,4-butanediol (BDO), gamma- butyrolactone and tetrahydrofuran (THF). It is important to highlight that BDO is one of the world's fastest growing chemicals in the last years.
Chemische Eigenschaften
Maleic anhydride is colorless needles, white lumps, or pellets. Irritating, choking odor. Dissolves in water to produce maleic acid. Dissolves in ethanol and produces esters.
Physikalische Eigenschaften
White, hydroscopic crystals (usually shipped as briquettes). Odor threshold concentration is 0.32
ppm (quoted, Amoore and Hautala, 1983).
Verwenden
Maleic Anhydride is heterocyclic compound used in the manufacture of unsaturated polyester resins. Maleic Anhydride has a wide range of other applications; it is used in synthetic tensides, insecticides, herbicides and fungicides.
Definition
ChEBI: Maleic anhydride is a cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid. It has a role as an allergen. It is a cyclic dicarboxylic anhydride and a member of furans.
synthetische
To a flask equipped with a Dean-Stark trap, condenser, and mechanical stirrer is added 116 gm (1.0 mole) of maleic acid and 120 ml of tetrachloroethane. The contents are heated, the water (18 ml, 1.0 mole) distilled off as the azeotrope, and the residue distilled under reduced pressure to afford 87.7 gm (89.5%) of the anhydride, b.p. 82-84°C (15 mm), m.p. 53°C. The residue remaining in the flask consists of about 10 gm of fumaric acid, m.p. 287°C.
Fumaric and maleic acids both give maleic anhydride on heating. Fumaric acid must first be heated to a higher temperature to effect its conversion to maleic acid prior to its dehydration.
Vorbereitung Methode
Maleic anhydride was traditionally manufactured by the oxidation of benzene or other aromatic compounds. As of 2006, only a few smaller plants continue to use benzene; due to rising benzene prices, most maleic anhydride plants now use n-butane as a feedstock.
In both cases, benzene and butane are fed into a stream of hot air, and the mixture is passed through a catalyst bed at high temperature. The ratio of air to hydrocarbon is controlled to prevent the mixture from catching on fire. Vanadium pentoxide and molybdenum trioxide are the catalysts used for the benzene route, whereas vanadium and phosphorus oxides are used for the butane route.
2 CH
3CH
2CH
2CH
3 + 7 O
2 → 2 C
2H
2(CO)
2O + 8 H
2O.
Reaktionen
The chemistry of maleic anhydride is very rich, reflecting its ready availability and bifunctional reactivity. It hydrolyzes, producing maleic acid, cis-HOOC–CH=CH–COOH. With alcohols, the halfester is generated, e.g., cis-HOOC–CH=CH–COOCH
3.
Maleic anhydride is a potent dienophile in Diels-Alder reactions. It is also a ligand for low-valent metal complexes, examples being Pt(PPh
3)
2(MA) and Fe(CO)
4(MA).
Maleic anhydride dimerizes in a photochemical reaction to form cyclo butane tetra carboxylic dianhydride (CBTA). This compound is used in the production of polyimides and as an alignment film for liquid crystal displays.
Allgemeine Beschreibung
Colorless crystalline needles, flakes, pellets, rods, briquettes, lumps or a fused mass. Melts at 113°F. Shipped both as a solid and in the molten state. Vapors, fumes and dusts strong irritate the eyes, skin and mucous membranes. Flash point 218°F. Autoignition temperature 890°F. Used to make paints and plastics and other chemicals.
Air & Water Reaktionen
Soluble in water. Reacts slowly with water to form maleic acid and heat.
Reaktivität anzeigen
Maleic anhydride react vigorously on contact with oxidizing materials. Reacts exothermically with water or steam. Undergoes violent exothermic decomposition reactions, producing carbon dioxide, in the presence of strong bases (sodium hydroxide, potassium hydroxide, calcium hydroxide), alkali metals (lithium, sodium, potassium), aliphatic amines (dimethylamine, trimethylamine), aromatic amines (pyridine, quinoline) at temperatures above 150° C [Vogler, C. A. et al., J. Chem. Eng. Data, 1963, 8, p. 620]. A 0.1% solution of pyridine (or other tertiary amine) in Maleic anhydride at 185°C gives an exothermic decomposition with rapid evolution of gas [Chem Eng. News 42(8); 41 1964]. Maleic anhydride is known as an excellent dienophile in the Diels-Alder reaction to produce phthalate ester derivatives. These reactions can be extremely violent, as in the case of 1-methylsilacyclopentadiene [J. Organomet., Chem., 1979, 179, c19]. Maleic anhydride undergoes a potentially explosive exothermic Diels-Alder reaction with 1-methylsilacyclopenta-2,4-diene at 150C [Barton, T. J., J. Organomet. Chem., 1979, 179, C19], and is considered an excellent dieneophile for Diels-alder reactions [Felthouse, Timothy R. et al. "Maleic anhydride , Maleic Acid, and Fumaric Acid." Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 2005].
Hazard
Irritant to tissue. Dermal and respiratory
sensitization. Questionable carcinogen.
Health Hazard
Inhalation causes coughing, sneezing, throat irritation. Skin contact causes irritation and redness. Vapors cause severe eye irritation; photophobia and double vision may occur.
Brandgefahr
Behavior in Fire: When heated above 300°F in the presence of various materials may generate heat and carbon dioxide. Will explode if confined.
Sicherheitsprofil
Poison by ingestion and
intraperitoneal routes. Moderately toxic by
skin contact. A corrosive irritant to eyes,
skin, and mucous membranes. Can cause
pulmonary edema. Questionable carcinogen
with experimental tumorigenic data.
Mutation data reported. A pesticide.
Combustible when exposed to heat or
flame; can react vigorously on contact with
oxidizing materials. Explosive in the form of
vapor when exposed to heat or flame.
Reacts with water or steam to produce heat.
Violent reaction with bases (e.g., sodmm
hydroxide, potassium hydroxide, calcium
hydroxide), dkah metals (e.g., sodium,
potassium), amines (e.g., dimethylamine,
triethylamine), lithium, pyridine. To fight
fire, use alcohol foam. Incompatible with
cations. When heated to decomposition
(above 150℃) it emits acrid smoke and
irritating fumes. See also ANHYDRIDES.
mögliche Exposition
Maleic anhydride is used in unsaturated polyester resins; Agricultural chemical, and lubricating additives; in the manufacture of unsaturated polyester
resins; in the manufacture of fumaric acid; in alkyd resin manufacture; in the manufacture of pesticides e.g., malathion, maleic hydrazide, and captan).
Versand/Shipping
UN2215 Maleic anhydride, Hazard class: 8; Labels: 8-Corrosive material.
Maleic Anhydride is commercialized and transported in the solid and molten forms. The molten Maleic Anhydride is transported at temperatures ranging from 60 to 80°C in well-insulated tank containers or road tankers provided with heating devices. In the solid form, it can be transported as pastilles, which are usually packed in polyethylene bags of 25 kg and transported either by rail tanker or by truck.
läuterung methode
Crystallise it from *benzene, CHCl3, CH2Cl2 or CCl4. Sublime it under reduced pressure. [Skell et al. J Am Chem Soc 108 6300 1986, Beilstein 17 III/IV 5897, 17/11 V 55.]
Inkompatibilitäten
Reacts slowly with water (hydrolyzes) to
form maleic acid, a medium-strong acid. Dust may form
explosive mixture with air. Reacts with strong oxidizers,
oil, water, alkali metals; strong acids; strong bases. Violent
reaction with alkali metals and amines above 66C.
Dangerous reaction with oxidizers, amines, alkali metals,
and hydroxides. Compounds of the carboxyl group react
with all bases, both inorganic and organic (i.e., amines)
releasing substantial heat, water and a salt that may be
harmful. Incompatible with arsenic compounds (releases
hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides
(releasing heat, toxic, and possibly flammable gases),
thiosulfates and dithionites (releasing hydrogen sulfate
and oxides of sulfur)
Waste disposal
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform to EPA regulations governing
storage, transportation, treatment, and waste disposal.
Controlled incineration: care must be taken that complete
oxidation to nontoxic products occurs.
Maleinsäureanhydrid Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
emulsion waterproof agent
Fumaronitril
tou-ming oil
1,2-Dihydro-1-phenylpyridazin-3,6-dion
Disodium succinate hexahydrate
Water-soluble resin
maleic acid-vinyl acetate copolymer
synthetic tanning agent DLT-14
endo-3,6-Methylen-1,2,3,6-tetrahydrophthalsureanhydrid
Pyridaphention
EXO-3,6-EPOXY-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE
1,1'-(Methylendi-p-phenylen)bismaleimid
Maleinsäure-diallylestcr
Dodecenylbernsteinsureanhydrid
Acipimox
Dispersing rosin latex
Water soluble epoxy resin
D,L-Asparaginmonohydrat
PR-I retanning agent
DL-Apfelsure
Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione
Dioctylmaleat
N-Ethylmaleimid
Di-(2-Ethylhexyl)4,5-Epoxytetrahydrophthalate
antistatic finish agent for synthetic fiber
Dibutylzinnmaleat
Sulfachlorpyridazin
Sizing agent for paper making
4-MALEIMIDOBUTYRIC ACID
maleic anhydride-benzylethylene sulfonated acid copolyer
neutral size-ASA
maleic anhydride-arcylic acid copolymer
3-Benzoylacrylsure
Dinatrium-4-[2-[(1-oxoundec-10-enyl)amino]ethyl]-2-sulfonatosuccinat
Dioctylzinnmaleat
PYRIDAZINE-3,6-DIOL
synthetic tanning agent KS-1
Methyl tetrahydrophthalic anhydride
Dibutylmaleat
Chrysen
