Adipinsure Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
GERUCHLOSES, FARBLOSES, KRISTALLINES PULVER.
PHYSIKALISCHE GEFAHREN
Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft m?glich. Die trockene Substanz kann durch Verwirbeln, Druckluft, Flie?en usw. elektrostatisch aufgeladen werden.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen unter Bildung giftiger und ?tzender Rauche (Valerians?ure und andere Substanzen). Schwache S?ure. Reagiert mit oxidierenden Stoffen.
ARBEITSPLATZGRENZWERTE
TLV: 5 mg/m?(als TWA); (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den K?rper durch Inhalation des Aerosols.
INHALATIONSGEFAHREN
Verdampfung bei 20°C vernachl?ssigbar; eine gesundheitssch?dliche Partikelkonzentration in der Luft kann jedoch beim Dispergieren schnell erreicht werden.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz reizt die Augen und die Atemwege. Inhalation des Aerosols dieser Substanz kann zu asthma?hnlichen Reaktionen führen.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Kontakt kann zu Hautsensibilisierung führen. Wiederholte oder andauernde Inhalation kann asthmatische Beschwerden hervorrufen.
Synthese
10 g Cyclohexanon werden in einem Erlenmeyerkolben mit einer L?sung aus 30.5 g Kaliumpermanganat in 500 ml Wasser versetzt. 10 ml einer 10%-igen Natronlauge werden zugegeben. Es wird durchgerührt und über Nacht stehen gelassen. Am n?chsten Tag wird erhitzt, um die Oxidation zu beenden und das entstandene Mangandioxid zusammenzuballen. Ein Tropfen der L?sung wird auf ein Stück Filtrierpapier gebracht. Bei Anwesenheit von überschüssigem Permanganat ist der dunkle Fleck von einem violetten Ring umgeben. In diesem Fall gibt man tropfenweise Natriumhydrogensulfitl?sung zu, bis alles Permanganat reduziert ist. Man saugt ab und w?scht gründlich mit Wasser aus. Das Filtrat muss farblos sein. Es wird auf 70 ml eingedampft. Sollte die L?sung nicht klar und farblos sein, wird sie mit etwas Aktivkohle geschüttelt und dann filtriert. Die hei?e L?sung wird mit konzentrierter Salzs?ure bis zum pH 1-2 anges?uert, dann werden noch 10 ml konzentrierte Salzs?ure zugegeben. Man l?sst auskristallisieren und erh?lt Adipins?ure mit einem von Schmelzpunkt 152-153 °C. Ausbeute betr?gt 6.9 g.
LECKAGE
Verschüttetes Material in Kunststoffbeh?ltern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste mit viel Wasser wegspülen.
R-S?tze Betriebsanweisung:
R36:Reizt die Augen.
S-S?tze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Aussehen Eigenschaften
C6H10O4; Butandicarbonsäure-(1,4); Hexandisäure.
Gefahren für Mensch und Umwelt
Reizt die Augen. Mit Basen, Oxidations- und Reduktionsmitteln sind gefährliche Reaktionen möglich.
Schutzma?nahmen und Verhaltensregeln
Bei Staubentwicklung im Abzug arbeiten.
Latex- oder Neopren-Schutzhandschuhe (nur als kurzzeitiger Spritz- und Staubschutz).
Verhalten im Gefahrfall
Bei Verschütten mechanisch aufnehmen. Beschmutzte Gegenstände gründlich mit Wasser reinigen.
In gut verschliessbaren Behältern der Entsorgung zuführen.
Wasser, Schaum-, Kohlendioxid- oder Pulverlöscher.
Erste Hilfe
Nach Hautkontakt: Sofort mit viel Wasser abwaschen.
Nach Augenkontakt: Mindestens 15 Minuten mit viel Wasser spülen. Augenarzt konsultieren.
Nach Verschlucken: Viel Wasser trinken lassen.
Den Betroffenen nur bei vollem Bewußtsein selbsttätig erbrechen lassen.
Sofort Arzt hinzuziehen.
Nach Kleidungskontakt: Beschmutzte Kleidung sofort ausziehen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als Sondermüll (organischer Feststoffabfall) entsorgen.
Beschreibung
Adipic acid is a crystalline powder with practically no odor. It has the lowest acidity of any of the acids commonly used in foods and has excellent buffering capacity in the range of pH 2.5 to 3.0. Like succinic and fumaric acid, adipic acid is practically nonhygroscopic. Its addition to foods imparts a smooth, tart taste. In grape-flavored products, it adds a lingering supplementary flavor and gives an excellent set to food powders containing gelatin. As a result, adipic acid has found a wide number of uses as an accidulant in dry powdered food mixtures, especially in those products having delicate flavors and where addition of tang to the flavor is undesirable.
Its aqueous solutions have the lowest acidity of any of the common food acids. For concentrations from 0.5 to 2.4 g/100 mL, the pH of its solution varies less than half a unit. Hence, it can be used as a buffering agent to maintain acidities within the range of 2.5 to 3.0. This is highly desirable in certain foods, yet the pH is low enough to inhibit the browning of most fruits and other foodstuffs.
Chemische Eigenschaften
Adipic acid is the organic compound with the formula (CH
2)
4(COOH)
2. From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon. Adipic acid otherwise rarely occurs in nature.
Physikalische Eigenschaften
Adipic acid is a straight-chain dicarboxylic acid that exists as a white crystalline compound at standard temperature and pressure. Adipic acid is one of the most important industrial chemicals and typically ranks in the top 10 in terms of volume used annually by the chemical industry.
Occurrence
Reported found as a minor constituent in butter, and has been found in other fats as a product of oxidative
rancidity. It also occurs in beet juice, pork fat, guava fruit (Psidium guajava L.), papaya (Carica papaya L.) and raspberry (Rubus
idaeus L.).
Verwenden
Adipic Acid is primarily used in the synthesis of nylon. It has been used as a reagent in the solid-state polymerization of nylon analogs.
synthetische
Adipic acid is produced from a mixture of cyclohexanol and cyclohexanone called "KA oil", the abbreviation of "ketone-alcohol oil." The KA oil is oxidized with nitric acid to give adipic acid, via a multistep pathway. Early in the reaction the cyclohexanol is converted to the ketone, releasing nitrous acid:
HOC
6H
11 + HNO
3 → OC
6H
10 + HNO
2 + H
2O
Among its many reactions, the cyclohexanone is nitrosated, setting the stage for the scission of the C- C bond:
HNO
2 + HNO
3 → NO+NO
3- + H
2O
OC
6H
10 + NO
+→ OC
6H
9-2 - NO + H
+ Side products of the method include glutaric and succinic acids.
Related processes start from cyclohexanol, which is obtained from the hydrogenation of phenol.
Definition
ChEBI: An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.
Vorbereitung Methode
Adipic acid is prepared by nitric acid oxidation of cyclohexanol or
cyclohexanone or a mixture of the two compounds. Recently,
oxidation of cyclohexene with 30% aqueous hydrogen peroxide
under organic solvent- and halide-free conditions has been
proposed as an environmentally friendly alternative for obtaining
colorless crystalline adipic acid.
Reaktionen
Adipic acid is a dibasic acid (can be deprotonated twice). Its pKa's are 4.41 and 5.41.
With the carboxylate groups separated by four methylene groups, adipic acid is suited for intramolecular condensation reactions. Upon treatment with barium hydroxide at elevated temperatures, it undergoes ketonization to give cyclopentanone.
Allgemeine Beschreibung
Adipic acid is a white crystalline solid. Adipic acid is insoluble in water. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Adipic acid is used to make plastics and foams and for other uses.
Air & Water Reaktionen
Dust may form explosive mixture with air [USCG, 1999]. Insoluble in water.
Health Hazard
Exposures to adipic acid cause pain, redness of the skin and eyes, tearing or lacrimation.
Adipic acid has been reported as a non-toxic chemical. Excessive concentrations of adipic
acid dust are known to cause moderate eye irritation, irritation to the skin, and dermatitis.It may be harmful if swallowed or inhaled. It causes respiratory tract irritation with symptoms
of coughing, sneezing, and blood-tinged mucous.
Pharmazeutische Anwendungen
Adipic acid is used as an acidifying and buffering agent in
intramuscular, intravenous and vaginal formulations. It is also
used in food products as a leavening, pH-controlling, or flavoring
agent.
Adipic acid has been incorporated into controlled-release
formulation matrix tablets to obtain pH-independent release for
both weakly basicand weakly acidic drugs.It has also been
incorporated into the polymeric coating of hydrophilic monolithic
systems to modulate the intragel pH, resulting in zero-order release
of a hydrophilic drug.The disintegration at intestinal pH of the
enteric polymer shellac has been reported to improve when adipic
acid was used as a pore-forming agent without affecting release in
the acidic media.Other controlled-release formulations have
included adipic acid with the intention of obtaining a late-burst
release profile.
Sicherheitsprofil
Poison by intraperitoneal route. Moderately toxic by other routes. A severe eye irritant. Combustible when exposed to heat or flame; can react with oxidzing materials. When heated to decomposition it emits acrid smoke and fumes.
Sicherheit(Safety)
Adipic acid is used in pharmaceutical formulations and food
products. The pure form of adipic acid is toxic by the IP route, and
moderately toxic by other routes. It is a severe eye irritant, and may
cause occupational asthma.
LD
50 (mouse, IP): 0.28 g/kg
LD
50 (mouse, IV): 0.68 g/kg
LD
50 (mouse, oral): 1.9 g/kg
LD
50 (rat, IP): 0.28 g/kg
LD
50 (rat, oral): >11 g/kg
m?gliche Exposition
Workers in manufacture of nylon, plasticizers, urethanes, adhesives, and food additives
Lager
Adipic acid is normally stable but decomposes above boiling point.
It should be stored in a tightly closed container in a cool, dry place,
and should be kept away from heat, sparks, and open flame.
Versand/Shipping
UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
l?uterung methode
For use as a volumetric standard, adipic acid is crystallised once from hot water with the addition of a little animal charcoal, dried at 120o for 2hours, then recrystallised from acetone and again dried at 120o for 2hours. Other purification procedures include crystallisation from ethyl acetate and from acetone/petroleum ether, fusion followed by filtration and crystallisation from the melt, and preliminary distillation under vacuum. [Beilstein 2 IV 1956.]
Inkompatibilit?ten
Adipic acid is incompatible with strong oxidizing agents as well as
strong bases and reducing agents. Contact with alcohols, glycols,
aldehydes, epoxides, or other polymerizing compounds can result in
violent reactions.
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
Vorsichtsma?nahmen
Occupational workers should avoid contact of the adipic acid with the eyes, avoid breathing
dust, and keep the container closed. Workers should use adipic acid only with adequate
ventilation. Workers should wash thoroughly after handling adipic acid and keep
away from heat, sparks, and flame. Also, workers should use rubber gloves and laboratory
coats, aprons, or coveralls, and avoid creating a dust cloud when handling, transferring,
and cleaning up.
Regulatory Status
GRAS listed. Included in the FDA Inactive Ingredients Database
(IM, IV, and vaginal preparations). Accepted for use as a food
additive in Europe. Included in an oral pastille formulation
available in the UK. Included in the Canadian List of Acceptable
Non-medicinal Ingredients.
Adipinsure Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
