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Dibutylamine

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Dibutylamine Basic information
Dibutylamine Chemical Properties
  • Melting point:−62 °C(lit.)
  • Boiling point:159 °C(lit.)
  • Density 0.767 g/mL at 25 °C(lit.)
  • vapor density 4.46 (vs air)
  • vapor pressure 1.9 mm Hg ( 20 °C)
  • refractive index n20/D 1.417(lit.)
  • Flash point:106 °F
  • storage temp. Flammables area
  • solubility water: soluble3.8g/L at 20°C
  • form Liquid
  • pka11.25(at 21℃)
  • color White
  • OdorWeak ammonia.
  • PH11.1 (1g/l, H2O, 20℃)
  • explosive limit0.6-6.8%(V)
  • Water Solubility 4.05 g/L (25 ºC)
  • Merck 14,3032
  • BRN 506001
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents, most common metals, strong acids. Vapours may flow over surfaces to a distant source of ignition. Can form explosive mixtures with air.
  • InChIKeyJQVDAXLFBXTEQA-UHFFFAOYSA-N
  • CAS DataBase Reference111-92-2(CAS DataBase Reference)
  • NIST Chemistry Reference1-Butanamine, N-butyl-(111-92-2)
  • EPA Substance Registry SystemDibutylamine (111-92-2)
Safety Information
MSDS
Dibutylamine Usage And Synthesis
  • Chemical Propertiescolourless liquid with an amine odour
  • Chemical PropertiesDibutylamine is a colorless liquid with an odor of ammonia.
  • Chemical Propertiesn-Dibutylamine is a strong base and undergoes reactions with acids. It reacts with carbon disulfide and carbon dioxide to form alkyl ammonium salts of dithiocarbamic acid and carbamic acid, respectively.
    n-Dibutylamine is nitrosated by nitrite at low pHs to form the mutagenic and carcinogenic product, N-nitrosodibutylamine (Sithole and Guy 1986).
  • UsesAnimal studies have demonstrated that dibutylamine is severely irritating to the eyes. An acute oral rat LD50 value of 550 mg/kg has been reported. The 4 h LC50 in rats is 1150 mg/m3. The 1 h LC50 in rats is >557 ppm.
    In a 90 day exposure of rats to 0, 50, 150, or 450 mg/m3, resulted in nasal metaplasia as well as a form of mucous cell hyperplasia.
  • Production Methodsn-Dibutylamine is prepared by two major methods. The first involves passing ammonia and butanol over an alumina or silica catalyst at a temperature of 300-500°C and under pressure. The second method employs passing ammonia, butanol, and hydrogen over a dehydrogenation catalyst. In each instance the resulting mixtures are separated by continuous distillation and extraction (Schweizer et al 1978). n-Dibutylamine can also be prepared from butyl bromide and ammonia or by reaction of butyl chloride and ammonia (HSDB 1989). The amine also is naturally present in food (Neurath et al 1977) and its emissions are produced in soil and sewage. The amine is also found in the expired air of normal, healthy, nonsmoking adults (Krotoszynski et al 1979).
    N-Nitrosamines and their precursors including n-dibutylamine are present in rubber products in which the accelerators and stabilizers used in the vulcanization process were derived from dialkylamines. Analysis of a single extraction of rubber nipples and baby pacifiers with artificial saliva (containing sodium nitrite) showed n-dibutylamine levels up to 3890 p.p.b. and N-nitrosodibutylamine concentrations as high as 427 p.p.b. (Thompson et al 1984).
  • General DescriptionA yellow-colored liquid with a amine-like odor. Denser than water. Very corrosive, may burn skin, eyes, and mucous membranes. Flash point 125°F. Combustible. Produce toxic oxides of nitrogen when burned. Used to make other chemicals.
  • Air & Water ReactionsFlammable. Soluble in water.
  • Reactivity ProfileDibutylamine 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 HazardInhalation causes irritation of nose, throat, and lungs; coughing; nausea; headache. Ingestion causes irritation of mouth and stomach. Contact with eyes causes irritation. Contact with skin causes irritation and dermatitis.
  • Health Hazardn-Dibutylamine is a severe irritant to skin and mucous membranes of the nose, eyes, and respiratory tract. Exposure to this amine may result in some activation of the sympathetic branch of the autonomic nervous system as manifested by elevated blood pressure, eye pupil dilation and flushing of the skin.
  • Fire HazardSpecial Hazards of Combustion Products: Toxic oxides of nitrogen may form in fires.
  • Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: May corrode some metals and attack some forms of plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
  • Industrial usesPrimary industrial uses of n-dibutylamine include flotation reagents, dyestuffs, rubber vulcanization accelerators, and corrosion inhibitors (HSDB 1989). In 1985 US production totalled approximately 2000 tons.
  • Safety ProfilePoison by ingestion and subcutaneous routes. Moderately toxic by skin contact and inhalation. Corrosive. A severe skin and eye irritant. Mutation data reported. Flammable liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam, foam, CO2, dry chemical. Exothermic reaction with cellulose nitrate does not proceed to ignition. When heated to decomposition it emits toxic fumes of NOx.
  • Potential ExposureUsed as a corrosion inhibitor; and intermediate for emulsifiers, rubber products, dyes; and insecticides.
  • MetabolismThere is little information available on the absorption, distribution and metabolism of ra-dibutylamine. Aliphatic amines such as dibutylamine are well absorbed from the gut. Both monoamine oxidase and diamine oxidase, which are present in most tissues, are capable of metabolizing many exogenous amines. Although the metabolism of primary amines is more rapid than secondary, the rate of oxidation by the enzyme increases with chain length of the amine, reaching a maximum of five carbon atoms (Beard and Noe 1981). Therefore, n-dibutylamine may be metabolized by these enzyme systems although definitive evidence is lacking.
    The highly carcinogenic and mutagenic N-nitrosodibutylamine is formed by reaction of nitrite with n-dibutylamine, the highest rates of nitrosation occurring at low pH (Sithole and Guy 1986). The n-dibutylamine present in ingested foods is nitrosated in the stomach by endogenous nitrite from saliva, etc. together with the sodium nitrite present in some preserved foods to form the highly toxic Nnitrosamine (Airoldi et al 1987). Food additives such as butylated hydroxyanisole inhibited in vitro the nitrosation of n-dibutylamine but this inhibition was not seen in vivo in rats that were given both n-dibutylamine and sodium nitrite.
    The endogenous formation of N-nitrosodibutylamine was studied in rats after administration of sodium nitrite or sodium nitrate and n-dibutylamine (Airoldi et al 1984). Urinary excretion of N-nitrosodibutylamine and its metabolites N-butyl- N-(4-hydroxybutyl)-nitrosamine (BBN) and N-butyl-N-(3-carboxypropyl)nitrosamine (BCPN) than was determined. Rats were supplied with 0.2% sodium nitrite or 0.5% sodium nitrate in drinking water and given n-dibutylamine by gavage at 3 doses of 50 mg/kg, 8 h apart. Analysis of the 24 h urine by GC equipped with a thermal energy analyzer failed to detect N-nitrosodibutylamine or its metabolite BBN. However, BCPN was found in the urine of both the sodium nitrite and sodium nitrate groups, indicating that in vivo nitrosation of n-dibutylamine had occurred.
  • ShippingUN2248 Di-n-butylamine, Hazard class: 8; Labels: 8-Corrosive material, 3-Flammable liquid.
  • Purification MethodsDry this strong base with LiAlH4, CaH2 or KOH pellets, filter and distil it from BaO or CaH2. [Beilstein 4 IV 550.]
  • IncompatibilitiesMay form explosive mixture with air. Aqueous solution is a strong base. Incompatible with acids, acid chlorides; acid anhydrides; halogens, isocyanates, vinyl acetate; acrylates, substituted allyls; alkylene oxides, epichlorohydrin, ketones, aldehydes, alcohols, gly- cols, phenols, cresols, caprolactum solution; strong oxidi- zers; reactive organic compounds. Attacks copper alloys, zinc, tin, tin alloys; galvanized steel. Also, carbon dioxide is listed as incompatible by the state of New Jersey.
  • Waste DisposalDissolve 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.
Dibutylamine Preparation Products And Raw materials
Dibutylamine (111-92-2)Related Product Information
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