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Butylamine

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Butylamine Basic information
Butylamine Chemical Properties
  • Melting point:−49 °C(lit.)
  • Boiling point:78 °C(lit.)
  • Density 0.74 g/mL at 25 °C(lit.)
  • vapor density 2.5 (vs air)
  • vapor pressure 68 mm Hg ( 20 °C)
  • refractive index n20/D 1.401(lit.)
  • FEMA 3130 | BUTYLAMINE
  • Flash point:30 °F
  • storage temp. 2-8°C
  • solubility water: miscible
  • pka10.77(at 20℃)
  • form Liquid
  • color Clear
  • OdorFish-like; ammonia-like.
  • PH12.6 (100g/l, H2O, 20℃)
  • Odor Threshold0.17ppm
  • explosive limit1.5-9.8%(V)
  • Water Solubility MISCIBLE
  • Sensitive Air Sensitive
  • Merck 14,1543
  • JECFA Number1582
  • BRN 605269
  • Henry's Law Constant1.76 (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
  • Exposure limitsCeiling 5 ppm (~15 mg/m3) (ACGIH, MSHA, and OSHA); IDLH 2000 ppm (NIOSH).
  • Stability:Stable. Incompatible with oxidizing agents, aluminium, copper, copper alloys, acids. Highly flammable.
  • InChIKeyHQABUPZFAYXKJW-UHFFFAOYSA-N
  • CAS DataBase Reference109-73-9(CAS DataBase Reference)
  • NIST Chemistry Reference1-Butanamine(109-73-9)
  • EPA Substance Registry SystemButylamine (109-73-9)
Safety Information
MSDS
Butylamine Usage And Synthesis
  • Descriptionn-Butylamine is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine, and isobutylamine. It is a colourless to yellow liquid and is highly flammable. It is stable and incompatible with oxidising agents, aluminium, copper, copper alloys, and acids. n-Butylamine finds its uses in the manufacture of pesticides (such as thiocarbazides), pharmaceuticals, and emulsifiers. It is also a precursor for the manufacture of N,N′-dibutylthiourea, a rubber vulcanisation accelerator, and n-butylbenzenesulphonamide, a plasticiser of nylon.
  • Chemical Propertiesn-Butylamine is a derivative of ammonia in which one of the hydrogen atoms is replaced with an alkyl group of four carbons. As such, it reacts with water and acids to form bases and salts, respectively. Acting as a very weak acid, it can react with acyl halides, anhydrides, and esters. With carbon disulfide and carbon dioxide, it forms the butyl ammonium salt of dithiocarbamic and carbamic acids, respectively. With isocyanic acid and alkyl or aryl isocyanates, it forms substituted ureas. When reacted with nitrous acid, rc-butylamine forms butyl alcohol with the release of nitrogen (Schweizer et al 1978).
    In the presence of water, rc-butylamine may corrode some metals (General Electric Co 1986) and attack glass (Schweizer et al 1978). Liquid n-butylamine also will attack some forms of plastics, rubber, and coatings (NIOSH 1981).
  • Physical properties

    Butylamine has an ammoniacal odor (fishy, pungent). Clear, colorless liquid with a strong or pungent, ammonia-like odor. Slowly becomes pale yellow on prolonged storage. Experimentally determined detection and recognition odor threshold concentrations were 240 μg/m3 (80 ppbv) and 720 μmg/m3 (240 ppbv), respectively (Hellman and Small, 1974).

  • OccurrenceReported found in mulberry leaves, kale, tomato, tilsit cheese, cheddar and other cheeses, caviar, fish, cooked chicken, cooked beef, beer, sherry and red wine.
  • Usesn-Butylamine is used as an intermediatefor various products, including dyestuffs,pharmaceuticals, rubber chemical, synthetictanning agents, and emulsifying agents. It isused for making isocyanates for coatings.
  • UsesIntermediate for pharmaceuticals, dyestuffs, rubber chemicals, emulsifying agents, insecticides, synthetic tanning agents.
  • DefinitionChEBI: A primary aliphatic amine that is butane substituted by an amino group at position 1.
  • Production Methodsn-Butylamine is usually manufactured by the catalytic alkylation of ammonia with butyl alcohol, or similarly from butyraldehyde and ammonia in the presence of Raney nickel. U.S. production in 1982 was approximately 1109 metric tons (SRI 1985). Some n-butylamine is also produced as a result of fertilizer manufacture, fish processing, rendering plant operations, and sewage treatment and has been reported to be a component of animal waste (Graedel 1978).
  • PreparationCatalytic alkylation of ammonia with butyl alcohol.
  • Aroma threshold valuesDetection: 50 ppm
  • General DescriptionA clear colorless liquid with an ammonia-like odor. Flash point 10°F. Less dense (6.2 lb / gal) than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.
  • Air & Water ReactionsHighly flammable. Dissolves in water with evolution of heat. The resulting solutions are basic.
  • Reactivity ProfileN-BUTYL AMINE reacts violently with strong oxidizing agents and acids. Attacks copper and copper compounds [Handling Chemicals Safely 1980 p. 123]. Reacts with hypochlorites to give N-chloroamines which may be explosive when isolated [Bretherick 1979 p. 108].
  • HazardSkin irritant. Flammable, dangerous fire risk. Eye and upper respiratory tract irritant.
  • Health Hazardn-Butylamine is a severe irritant to the eyes,skin, and respiratory tract. Contact of theliquid with the skin and eyes can producesevere burns. Irritation effect on rabbits’ eyeswas as severe as that produced by ethylamine(ACGIH 1986). Exposure can cause irritationof the nose and throat, and at high concen trations, pulmonary edema. Scherberger andassociates (1960) have reported erythema ofthe face and neck occurring within 3 hoursafter exposure to n-butylamine, along with aburning and itching sensation.
    n-Butylamine is more toxic than is eithern-propylamine or ethylamine. A 4-hourexposure to 3000-ppm concentration in airwas lethal to rats. Toxic symptoms in animalsfrom ingestion include increased pulse rate,labored breathing, and convulsions. Cyanosisand coma can occur at near-lethal dose.
    LD50 value, oral (rats): 366 mg/kg
    LD50 value, skin (guinea pigs): 366 mg/kg.
  • Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: May corrode some metals in presence of water; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
  • Industrial usesn-Butylamine is an important intermediate in the production of pharmaceuticals, dyestuffs, synthetic tanning agents, insecticides, emulsifying agents, rubber accelerators, vulcanizing agents, and antioxidants (HSDB 1988). A flavor ingredient in seafood and chocolate, n-butylamine is also reported to be used in alcoholic beverages, ice cream, candy, baked goods, gelatins, and puddings all at a concentration of 0.1 p.p.m. (Fenaroli 1975). It is estimated that 50% of the n-butylamine produced is used for rubber processing chemicals and 50% as an intermediate in pesticide production (SRI 1982).
  • Potential ExposureAlert: (n-isomer): Possible risk of forming tumors, suspected of causing genetic defects, suspected reprotoxic hazard, Primary irritant (w/o allergic reaction), (sec-isomer): Drug. n-Butylamine is used in pharmaceuticals; dyestuffs, rubber, chemicals, emulsifying agents; photography, desizing agents for textiles; pesticides, and synthetic agents. sec-Butylamine is used as a fungistate. tert-Butylamine is used as a chemical intermediate in the production of tert-Butylaminoethyl methacrylate (a lube oil additive); as an intermediate in the production of rubber and in rust preventatives and emulsion deterrents in petroleum products. It is used in the manufacture of several drugs
  • Environmental FatePhotolytic. Low et al. (1991) reported that the photooxidation of aqueous primary amine solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium and nitrate ions.
    Chemical/Physical. Reacts with mineral acids forming water-soluble salts.
    At an influent concentration of 1.0 g/L, treatment with GAC resulted in effluent concentration of 480 mg/L. The adsorbability of the carbon used was 103 mg/g carbon (Guisti et al., 1974).
  • MetabolismConsidering the industrial importance of this amine, it is surprising that no thorough studies of its metabolism have been completed. Aliphatic amines, in general, are well-absorbed from the gut and respiratory tract and readily metabolised (Beard and Noe 1981; Magos and Manson 1983). After oral administration of n-butylamine hydrochloride to humans, little n-butylamine was recovered in the urine (Rechenberger 1940) suggesting that extensive metabolism occurs. Deamination of n-butylamine has been shown to occur in slices of rat liver and brain cortex (Pugh and Quastel 1937). It is assumed that monoamine oxidase plays a role in the detoxication process by catalyzing the deamination of n-butylamine to ammonia, hydrogen peroxide, and butyraldehyde. The ammonia produced is then converted to urea and the hydrogen peroxide is reduced by catalase. The aldehyde is probably converted to the corresponding carboxylic acid by aldehyde oxidase (Beard and Noe, 1981).
  • storagen-Butylamine should be protected against physical damage. Store in a cool, dry, wellventilated location, away from any area where the fi re hazard may be acute. Outside or detached storage is preferred. Separate from incompatibles. Containers should be bonded and grounded for transfer to avoid static sparks.
  • ShippingUN1125 n-Butylamine, Hazard Class: 3; Labels: 3—Flammable liquid, 8—Corrosive material. UN2014 Isobutylamine, Hazard Class: 3; Labels: 3—Flammable liquid, 8—Corrosive material
  • Purification MethodsDry it with solid KOH, K2CO3, LiAlH4, CaH2 or MgSO4, then reflux it with, and fractionally distil it from P2O5, CaH2, CaO or BaO. Further purification is by precipitation as the hydrochloride, m 213-213.5o, from ethereal solution by bubbling HCl gas into it. This is re-precipitated three times from EtOH by adding ether, followed by liberation of the free amine using excess strong base. The amine is extracted into ether, which is separated, dried with solid KOH, the ether removed by evaporation and then the amine is distilled. It is stored in a desiccator over solid NaOH [Bunnett & Davis J Am Chem Soc 82 665 1960, Lycan et al. Org Synth Coll Vol II 319 1943]. [Beilstein 4 IV 540.] SKIN IRRITANT.
  • IncompatibilitiesMay form explosive mixture with air. May accumulate static electrical charges, and may causeignition of its vapors. n-Butylamine is a weak base; reacts with strong oxidizers and acids, causing fire and explosion hazard. Incompatible with organic anhydrides; isocyanates, vinyl acetate; acrylates, substituted allyls; alkylene oxides; epichlorohydrin, ketones, aldehydes, alcohols, glycols, phenols, cresols, caprolactum solution. Attacks some metals in presence of moisture. The tert-isomer will attack some forms of plastics
  • Waste DisposalUse a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner andscrubber. All federal, state, and local environmental regulations must be observed.
Butylamine Preparation Products And Raw materials
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