Description
n-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 Properties
n-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).
Occurrence
Reported found in mulberry leaves, kale, tomato, tilsit cheese, cheddar and other cheeses, caviar, fish, cooked
chicken, cooked beef, beer, sherry and red wine.
Uses
n-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.
Uses
Intermediate for pharmaceuticals, dyestuffs, rubber chemicals, emulsifying agents, insecticides, synthetic tanning agents.
Definition
ChEBI: A primary aliphatic amine that is butane substituted by an amino group at position 1.
Production Methods
n-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).
Preparation
Catalytic alkylation of ammonia with butyl alcohol.
Aroma threshold values
Detection: 50 ppm
General Description
A 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 Reactions
Highly flammable. Dissolves in water with evolution of heat. The resulting solutions are basic.
Reactivity Profile
N-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].
Hazard
Skin irritant. Flammable, dangerous fire
risk. Eye and upper respiratory tract irritant.
Health Hazard
n-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.
Flammability and Explosibility
Flammable
Chemical Reactivity
Reactivity 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 uses
n-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 Exposure
Alert: (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
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Rinse out mouth and do not induce vomiting.Medical observation is recommended for 2448 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray.
Carcinogenicity
The concentrated liquid produced severe
eye damage and skin burns in animals.
Environmental Fate
Photolytic. 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).
Metabolism
Considering 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).
Solubility in water
Butylamine can dissolve in water by forming hydrogen bonds with water. Oxygen atoms in water hydrogen-bond to hydrogen atoms on the amine group.
storage
n-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.
Shipping
UN1125 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 Methods
Dry 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.
Incompatibilities
May 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 Disposal
Use 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.
