Cyclohexylamin Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSE BIS GELBE FLüSSIGKEIT MIT STECHENDEM GERUCH.
CHEMISCHE GEFAHREN
Zersetzung beim Verbrennen unter Bildung giftiger und ?tzender Rauche mit Stickstoffoxiden. Starke Base. Reagiert sehr heftig mit S?uren. ?tzend. Reagiert sehr heftig mit starken Oxidationsmitteln unter Feuergefahr. Greift Aluminium, Kupfer Zink an.
ARBEITSPLATZGRENZWERTE
TLV: 10 ppm (als TWA); Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
MAK: 2 ppm, 8.2 mg/m? Spitzenbegrenzung: überschreitungsfaktor I(2); Schwangerschaft: Gruppe C; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den K?rper durch Inhalation, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C kann schnell eine gesundheitssch?dliche Kontamination der Luft eintreten.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz ver?tzt die Augen, die Haut und die Atemwege. ?tzend beim Verschlucken. M?glich sind Auswirkungen auf das Zentralnervensystem.
LECKAGE
Gefahrenbereich verlassen! Ausgelaufene Flüssigkeit in abdichtbaren Beh?ltern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. Pers?nliche Schutzausrüstung: Umgebungsluftunabh?ngiges Atemschutzger?t.
R-S?tze Betriebsanweisung:
R10:Entzündlich.
R21/22:Gesundheitssch?dlich bei Berührung mit der Haut und beim Verschlucken.
R34:Verursacht Ver?tzungen.
S-S?tze Betriebsanweisung:
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S1/2:Unter Verschluss und für Kinder unzug?nglich aufbewahren.
Aussehen Eigenschaften
C6H13N; Aminocyclohexan, Cyclohexanamin. Farblose Flüssigkeit mit aminartigem Geruch.
Gefahren für Mensch und Umwelt
Gesundheitsschädlich bei Berührung mit der Haut und beim Verschlucken. Verursacht Verätzungen.
Kann zu Lungenödemen führen.
Nicht mit starken Oxidationsmitteln und Säuren in Berührung bringen. Entzündlich.
LD
50 (oral, Ratte): 156 mg/kg
Schutzma?nahmen und Verhaltensregeln
Geeignete Schutzhandschuhe als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Dämpfe nicht einatmen.
Mit flüssigkeitsbindendem Material, z.B. Rench Rapid aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Wasser, Pulver.
Brennbar. Mit Luft Bildung explosionsfähiger Gemische möglich.
Erste Hilfe
Nach Hautkontakt: Mit viel Wasser abwaschen. Abtupfen mit Polyethylenglycol 400.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft. Arzt hinzuziehen.
Nach Verschlucken: Zitronensaft oder Speiseessig, dann viel Wasser trinken lassen. Erbrechen wegen Perforationsgefahr vermeiden. Sofort Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als halogenfreie, organische Lösemittelabfälle.
Chemische Eigenschaften
Cyclohexylamine is a colorless to yellow liquid (amines, primary aromatic). It has an unpleasant fishy odor. Flammable. It is infinitely miscible with water and conventional organic solvents. With water it forms an azeotrope that contains 44.2 % cyclohexylamine and boils at 96.4℃. Cyclohexylamine can be volatilized with water vapor. It can absorb carbon dioxide in the air and form a white crystalline carbonate. Aqueous solution is alkaline. 0.01% concentration of aqueous solution pH = 10.5. Its vapor and air to form an explosive mixture.
Verwenden
Cyclohexylamine is used in the manufacture of a number of products, including plasticizers, drycleaning soaps, insecticides, and emulsifying agents. It is also used as a corrosion inhibitor and in organic synthesis.
Definition
ChEBI: Cyclohexylamine is a primary aliphatic amine consisting of cyclohexane carrying an amino substituent. It has a role as a human xenobiotic metabolite and a mouse metabolite. It is a conjugate base of a cyclohexylammonium.
Vorbereitung Methode
Cyclohexylamine is produced by the reaction of ammonia and cyclohexanol at
elevated temperature and pressure in the presence of a silica-alumina catalyst
(SRI 1985). It is also prepared by a similar process of catalytic hydrogenation of
aniline at elevated temperature and pressure. Fractionation of the product of this
reaction yields CHA, aniline, and a high-boiling residue containing n-phenylcyclohexylamine
and dicyclohexylamine (Carswell and Morrill 1937). In 1982,
U.S. production was 4.54 metric tons and 739.3 metric tons were imported into the
U.S. (SRI 1985).
Allgemeine Beschreibung
Cyclohexylamine appears as a clear colorless to yellow liquid with an odor of ammonia. Flash point 90 °F. Irritates the eyes and respiratory system. Skin contact may cause burns. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.
Air & Water Reaktionen
Highly flammable. Sensitive to air and light. Soluble in water.
Reaktivit?t anzeigen
Cyclohexylamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Health Hazard
Cyclohexylamine is a severe irritant to theeyes, skin, and respiratory passage. Skincontact can produce burns and sensitization;contact of the pure liquid or its concentratedsolutions with the eyes may cause loss ofvision.
The acute oral and dermal toxicity ofcyclohexylamine was moderate in test sub jects. The toxic effects include nausea, vom iting, and degenerative changes in the brain,liver, and kidney. Inhalation of its vaporsat high concentrations may cause a narcoticeffect.
LD50 value, oral (rats): 156 mg/kg
LD50 value, skin (rabbits): 277 mg/klg
Cyclohexylamine may be mutagenic, thetest for which has so far given inconclusiveresults. Administration of this compoundin animals produced a reproductive effect,including embryotoxicity and a reductionin male fertility. Intraperitoneal injectionof the amine in rats caused a dose dependent increase in chromosomal breaks.Roberts and coworkers (1989) studied themetabolism and testicular toxicity of cyclohexylamine (a metabolite of cyclamate)in rats and mice. Chronic dietary administration of 400 mg/kg/day for 13 weeksshowed decrease in organ weigh, histological changes, and testicular atrophy in boththe Wistar and dark agouti DA rats, but to awidely varying extent, while mice exhibitedno evidence of testicular damage.
There is no evidence of carcinogenicityin animals or humans caused by cyclohexy lamine.
Brandgefahr
When heated to decomposition, Cyclohexylamine emits highly toxic fumes. Vapor may travel a considerable distance to source of ignition and flash back. Toxic oxides of nitrogen are produced during combustion. Nitric acid; reacts vigorously with oxiding materials. Stable, avoid physical damage, storage with oxidizing material.
Industrielle Verwendung
The primary use of cyclohexylamine is as a corrosion inhibitor in boiler water
treatment and in oil field applications (HSDB 1989). It is also a chemical
intermediate for rubber processing chemicals, dyes (acid blue 62, former use),
cyclamate artificial sweeteners and herbicides and a processing agent for nylon
fiber production (SRI 1985). Windholz et al (1983) reports its use in the manufacture
of insecticides, plasticizers, emulsifying agents, dry-cleaning soaps, and acid
gas absorbents.
Sicherheitsprofil
A poison by ingestion,
skin contact, and intraperitoneal routes.
Experimental teratogenic and reproductive
effects. A severe human skin irritant. Can
cause dermatitis and convulsions. Human
mutation data reported. Questionable
carcinogen. Flammable liquid. Dangerous
fire hazard when exposed to heat, flame, or
oxidizers. To fight fire, use alcohol foam,
CO2, dry chemical. When heated to
decomposition it emits toxic fumes of NOx.
Synthese
Prepared by catalytic hydrogenation of aniline at elevated temp and pressures. Fractionation of crude reaction product yields cyclohexylamine, unchanged aniline, and high-boiling residue containing n-phenylcyclohexylamine (cyclohexylaniline) and dicyclohexylamine.
m?gliche Exposition
CHA is used in making dyes, chemi-
cals, dry cleaning chemicals; insecticides, plasticizers, rub-
ber chemicals; and as a chemical intermediate in the
production of cyclamate sweeteners. Used in water treat-
ment and as a boiler feedwater additive. It is also used in
rubber production to retard degradation.
Carcinogenicity
According to the International Agency for Research of Cancer (IARC) working group, there is no evidence that cyclohexylamine is teratogenic or carcinogenic.
Lager
Cyclohexylamine can be stored and shipped in iron tanks. Nonferrous metals, particularly copper-containing materials, are attacked and are therefore unsuitable. The amine discolors on contact with air and therefore must be kept under nitrogen.
Versand/Shipping
UN2357 Cyclohexylamine, Hazard class: 8;
Labels: 8-Corrosive material, 3-Flammable liquid.
l?uterung methode
Dry the amine with CaCl2 or LiAlH4, then distil it from BaO, KOH or Na, under N2. Also purify it by conversion to the hydrochloride (which is crystallised several times from water), then liberation of the amine with alkali and fractional distillation under N2. The hydrochloride has m 205-207o (dioxane/EtOH). [Lycan et al. Org Synth Coll Vol II 319 1943, Beilstein 12 III 10, 12 IV 8.]
Inkompatibilit?ten
May form explosive mixture with air.
Cyclohexylamine is a strong base: it reacts violently with
acid. Contact with strong oxidizers may cause fire and
explosion hazard. Incompatible with organic anhydrides;
isocyanates, vinyl acetate; acrylates, substituted allyls;
alkylene oxides; epichlorohydrin, ketones, aldehydes, alco-
hols, glycols, phenols, cresols, caprolactum solution; lead.
Corrosive to copper alloys, zinc, or galvanized steel.
Waste disposal
Incineration; incinerator
equipped with a scrubber or thermal unit to reduce nitrogen
oxides emissions.
Cyclohexylamin Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Cross-linking agent
N,N'-DICYCLOHEXYLUREA
1-CYCLOHEXYLURACIL
Cyclohexylammoniumbromid
6-(Cyclohexylamino)-3-methyl-3H-dibenz[f,ij]isochinolin-2,7-dion
Nitrocyclohexan
1-(2-Chlorethyl)-3-cyclohexyl-1-nitrosoharnstoff
Resin curing agent
Captopril
1-Cyclohexyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile ,97%
Cyclohexyl(methyl)amin
(DHQ)2PYR
(DHQD)2PYR
Transparent Red CHA
N-Cyclohexylsulfamidsure
Natrium-1-amino-4-(cyclohexylamino)-9,10-dihydro-9,10-dioxoanthracen-2-sulfonat
Hexythiazox
Cyclohexylisocyanat
Natriumcyclamat
Melassen
N-Cyclohexylbenzothiazol-2-sulfenamid
Dicyclohexylcarbodiimid
