Adipinsure

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H318：Verursacht schwere Augenschäden.

• Sicherheit

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Adipic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

• ERSCHEINUNGSBILD

  GERUCHLOSES, FARBLOSES, KRISTALLINES PULVER.

• PHYSIKALISCHE GEFAHREN

  Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft möglich. Die trockene Substanz kann durch Verwirbeln, Druckluft, Fließen usw. elektrostatisch aufgeladen werden.

• CHEMISCHE GEFAHREN

  Zersetzung beim Erhitzen unter Bildung giftiger und ätzender Rauche (Valeriansäure und andere Substanzen). Schwache Säure. Reagiert mit oxidierenden Stoffen.

• ARBEITSPLATZGRENZWERTE

  TLV: 5 mg/m?(als TWA); (ACGIH 2005).
  MAK nicht festgelegt (DFG 2005).
  

• AUFNAHMEWEGE

  Aufnahme in den Körper durch Inhalation des Aerosols.

• INHALATIONSGEFAHREN

  Verdampfung bei 20°C vernachlässigbar; eine gesundheitsschädliche 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 asthmaähnlichen 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 Lösung 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 nächsten Tag wird erhitzt, um die Oxidation zu beenden und das entstandene Mangandioxid zusammenzuballen. Ein Tropfen der Lösung 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 Natriumhydrogensulfitlösung zu, bis alles Permanganat reduziert ist. Man saugt ab und wäscht gründlich mit Wasser aus. Das Filtrat muss farblos sein. Es wird auf 70 ml eingedampft. Sollte die Lösung nicht klar und farblos sein, wird sie mit etwas Aktivkohle geschüttelt und dann filtriert. Die heiße Lösung wird mit konzentrierter Salzsäure bis zum pH 1-2 angesäuert, dann werden noch 10 ml konzentrierte Salzsäure zugegeben. Man lässt auskristallisieren und erhält Adipinsäure mit einem von Schmelzpunkt 152-153 °C. Ausbeute beträgt 6.9 g.
  

• LECKAGE

  Verschüttetes Material in Kunststoffbehältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste mit viel Wasser wegspülen.

• R-Sätze Betriebsanweisung:

  R36:Reizt die Augen.

• S-Sätze 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.

• Schutzmaßnahmen 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 (CH₂)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’s main use is in the production of 6,6 nylon. It is also used in resins, plasticizers, lubricants, polyurethanes, and food additives.

• Verwenden

  Adipic Acid is an acidulant and flavoring agent. it is characterized as stable, nonhygroscopic, and slightly soluble, with a water solubility of 1.9 g/100 ml at 20°c. it has a ph of 2.86 at 0.6% usage level at 25°c. it is used in powdered drinks, beverages, gelatin desserts, loz- enges, and canned vegetables. it is also used as a leavening acidulant in baking powder. it can be used as a buffering agent to maintain acidities within a range of ph 2.5–3.0. it is occasionally used in edi- ble oils to prevent rancidity.

• 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:
  HOC₆H₁₁ + HNO₃ → OC₆H₁₀ + HNO₂ + H₂O
  Among its many reactions, the cyclohexanone is nitrosated, setting the stage for the scission of the C- C bond:
  HNO₂ + HNO₃ → NO+NO₃^- + H₂O
  OC₆H₁₀ + NO⁺→ OC₆H₉^-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.

• Vorbereitung Methode

  Adipic acid can be manufactured using several methods, but the traditional and main route of preparation is by the two-step oxidation of cyclohexane (C₆H₁₂). In the first step, cyclohexane is oxidized to cyclohexanone and cyclohexanol with oxygen or air. This occurs at a temperature of approximately 150°C in the presence of cobalt or manganese catalysts. The second oxidation is done with nitric acid and air using copper or vanadium catalysts. In this step, the ring structure is opened and adipic acid and nitrous oxide are formed. Other feedstocks such as benzene and phenol may be use to synthesize adipic acid. Adipic acid production used to be a large emitter of nitrous oxide, a greenhouse gas, but these have been controlled in recent years using pollution abatement technology.

• 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.

• Biotechnologische Produktion

  Adipic acid is industrially produced by chemical synthesis. However, there are new efforts to develop an adipic acid production process using biorenewable sources. A direct biosynthesis route has not yet been reported. The possible precursors Z,Z-muconic acid and glucaric acid can be produced biotechnologically by fermentation. Z,Z-muconic acid can be made from benzoate with concentrations up to 130 mM with a yield of close to 100 % (mol/mol) by Pseudomonas putida KT2440-JD1 grown on glucose. Alternatively, it can be produced by engineered E. coli directly from glucose at up to 260 mM with a yield of 0.2 mol Z,Zmuconic acid per mole glucose .
  The production of the second possible precursor, glucaric acid, by engineered E. coli growing on glucose has been reported. However, the product titers were low (e.g. 4.8 and 12 mM. To overcome the problem of low product concentrations, an alternative synthetic pathway has been suggested but not yet demonstrated .
  In a hydrogenation process, Z,Z-muconic acid and glucaric acid could be converted chemically into adipic acid. Therefore, bimetallic nanoparticles or platinum on activated carbon as catalysts have been studied . In particular, nanoparticles of Ru10Pt2 anchored within pores of mesoporous silica showed high selectivity and conversion rates, greater than 0.90 mol adipic acid per mole Z,Zmuconicacid. With platinum on activated carbon, conversion rates of 0.97 mol.mol-1 of Z,Z-muconic acid into adipic acid have been shown. Another possibility would be the production of adipic acid from glucose via the a–aminoadipate pathway ]. Finally, the production of adipic acid from longchain carbon substrates has been suggested. The conversion of fatty acids into dicarboxylic acids by engineered yeast strains has been reported.

• 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.

• Reaktivität anzeigen

  Adipic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Adipic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. Behavior in Fire: Melts and may decompose to give volatile acidic vapors of valeric acid and other substances.

• 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.

• Flammability and Explosibility

  Non flammable

• 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.
  LD₅₀ (mouse, IP): 0.28 g/kg
  LD₅₀ (mouse, IV): 0.68 g/kg
  LD₅₀ (mouse, oral): 1.9 g/kg
  LD₅₀ (rat, IP): 0.28 g/kg
  LD₅₀ (rat, oral): >11 g/kg

• Synthese

  By oxidation of cyclohexanol with concentrated nitric acid; by catalytic oxidation of cyclohexanone with air.

• mögliche 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

• läuterung 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.]

• Inkompatibilitäten

  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.

• Filter für giftige stoffe

  The initial threshold screening level (ITSL) for adipic acid is 50 μg/m3 based on an 8 hour averaging time.

• 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

• Vorsichtsmaßnahmen

  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.

Adipic acid Upstream-Materialien And Downstream Produkte

Adipinsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(1229)Suppliers

124-04-9, Adipic acid Verwandte Suche: