Chemical Properties
n-Butylamine is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine, and isobutylamine. It is a highly flammable, colorless to yellow
liquid. It is stable and/but incompatible with oxidizing agents, aluminium, copper, copper
alloys, and acids. n-Butylamine is used in the manufacture of pesticides (such as thiocarbazides), pharmaceuticals, and emulsifi ers. It is also a precursor for the manufacture of
N,N’-dibutylthiourea, a rubber vulcanization accelerator, and n-butylbenzenesulfonamide,
a plasticizer of nylon.
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.
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].
Air & Water Reactions
Highly flammable. Dissolves in water with evolution of heat. The resulting solutions are basic.
Hazard
Skin irritant. Flammable, dangerous fire
risk. Eye and upper respiratory tract irritant.
Health Hazard
Exposures to butylamine (inhalation, ingestion, and through skin contact) are harmful.
It is very destructive to the mucous membranes and causes, redness, severe deep burns,
and loss of vision. Symptoms include, but are not limited to, sore throat, cough, burning
sensation, headache, fl ushing of the face, vomiting, dizziness, abdominal pain, diarrhea,
nausea, shock or collapse, shortness of breath, labored breathing, depression, convulsions, narcosis, and possibly unconsciousness. Exposure of this nature is unlikely, however, because of the irritating properties of the vapor. On catching fi re, butylamine gives
off irritating or toxic fumes (or gases). Repeated or prolonged contact with the skin may
cause dermatitis. The vapor is corrosive to the eyes, skin, and respiratory tract, and causes
lung edema.
Health Hazard
Inhalation causes irritation, nausea, vomiting, headache, faintness, severe coughing and chest pains; can cause lung edema. Ingestion causes severe irritation of mouth and stomach. Contact with eyes causes severe irritation and edema of the cornea. Contact with skin causes burns; absorption through skin may cause nausea, vomiting and shock.
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 any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Rinse out mouth and do not induce vomiting.
Medical observation is recommended for 24 to 48 hours
after breathing overexposure, as pulmonary edema may be
delayed. As first aid for pulmonary edema, a doctor or
authorized paramedic may consider administering a drug or
other inhalation therapy
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
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.
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
Intermediate for pharmaceuticals, dyestuffs, rubber chemicals, emulsifying agents, insecticides, synthetic tanning agents.
Uses
Intermediate for pharmaceuticals,
dyestuffs, rubber chemicals, emulsifying
agents, insecticides, synthetic tanning agents
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.
Definition
ChEBI: A primary aliphatic amine that is butane substituted by an amino group at position 1.
Preparation
Catalytic alkylation of ammonia with butyl alcohol.
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).
Aroma threshold values
Detection: 50 ppm
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).
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.
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.
