Chemical Properties
n-Butyl alcohol is a colorless flammable liquid with a strong alcoholic odor. n-Butyl
alcohol is a highly refractive liquid and burns with a strongly luminous flame. It is
incompatible with strong acids, strong oxidizing agents, aluminium, acid chlorides,
acid anhydrides, copper, and copper alloys. n-Butyl alcohol has extensive use in a large
number of industries. For instance, it is used as a solvent in industries associated with
the manufacturing of paints, varnishes, synthetic resins, gums, pharmaceuticals, veg etable oils, dyes, and alkaloids. n-Butyl alcohol is used in the manufacture of artifi cial
leather, rubber, and plastic cements, shellac, raincoats, perfumes, and photographic
fi lms.
General Description
Colorless liquid. Used in organic chemical synthesis, plasticizers, detergents, etc.
Reactivity Profile
N-BUTYL ALCOHOL(71-36-3) attacks plastics. [Handling Chemicals Safely 1980. p. 236]. Mixtures with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. May form explosive butyl hypochlorite by reacting with hypochlorous acid. May form butyl explosive butyl hypochlorite with chlorine.
Air & Water Reactions
Highly flammable. Soluble in water.
Hazard
Toxic on prolonged inhalation, irritant to
eyes. Toxic when absorbed by skin. Flammable,
moderate fire risk. Eye and upper respiratory tract
irritant.
Health Hazard
Anesthesia, nausea, headache, dizziness, irritation of respiratory passages. Mildly irritating to the skin and eyes.
Health Hazard
Exposures to n-butyl alcohol by inhalation, ingestion, and/or skin absorption are harm ful. n-Butyl alcohol is an irritant, with a narcotic effect and a CNS depressant. Butyl
alcohols have been reported to cause poisoning with symptoms that include, but are
not limited to, irritation to the eyes, nose, throat, and the respiratory system. Prolonged
exposure results in symptoms of headache, vertigo, drowsiness, corneal infl amma tion, blurred vision, photophobia, and cracked skin. It is advised that workers com ing in contact with n-butyl alcohol should use protective clothing and barrier creams.
Occupational workers with pre-existing skin disorders or eye problems, or impaired
liver, kidney or respiratory function may be more susceptible to the effects of the
substance.
Potential Exposure
Butyl alcohols are used as solvents for
paints, lacquers, varnishes, natural and synthetic resins,
gums, vegetable oils, dyes, camphor, and alkaloids. They
are also used as an intermediate in the manufacture of pharmaceuticals and chemicals; in the manufacture of artificial
leather, safety glass; rubber and plastic cements, shellac,
raincoats, photographic films, perfumes; and in plastic
fabrication.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
First aid
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way
valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and
isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact,
avoid spreading material on unaffected skin. Keep victim
warm and quiet. Effects of exposure (inhalation, ingestion
or skin contact) to substance may be delayed. Ensure that
medical personnel are aware of the material(s) involved
and take precautions to protect themselves. 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
UN1120 Butanols, Hazard Class: 3; Labels: 3—
Flammable liquid. UN1212 Isobutanol or Isobutyl alcohol,
Hazard Class: 3; Labels: 3—Flammable liquid
Incompatibilities
Butyl alcohols may form explosive mixture with air. In all cases they are Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates,
perchlorates, chlorine, bromine, fluorine, etc.); contact may
cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Attacks
some plastics, rubber and coatings. n-Butanol is incompatible with strong acids; halogens, caustics, alkali metals; aliphatic amines; isocyanates. sec-Butanol forms an explosive
peroxide in air. Ignites with chromium trioxide.
Incompatible with strong oxidizers; strong acids; aliphatic
amines; isocyanates, organic peroxides. tert-Butanol is
incompatible with strong acids (including mineral acid),
including mineral acids; strong oxidizers or caustics, aliphatic amines; isocyanates, alkali metals (i.e., lithium,
sodium, potassium, rubidium, cesium, francium). isoButanol is incompatible with strong acids; strong oxidizers;
caustics, aliphatic amines; isocyanates, alkali metals and
alkali earth. May react with aluminum at high temperatur
Waste Disposal
Incineration, or bury absorbed
waste in an approved land fill.
Physical properties
Clear, colorless liquid with a rancid sweet odor similar to fusel oil. Experimentally determined
detection and recognition odor threshold concentrations were 900 μg/m3 (300 ppbv) and 3.0 mg/m3
(1.0 ppmv), respectively (Hellman and Small, 1974). Odor threshold concentration in water is 500
ppb (Buttery et al., 1988). The least detectable odor threshold in concentration water at 60 °C was
0.2 mg/L (Alexander et al., 1982). Cometto-Mu?iz et al. (2000) reported nasal pungency threshold
concentrations ranging from approximately 900 to 4,000 ppm.
Occurrence
Reported present in peppermint oil from Brazil, Achillea ageratum, tea, apple aroma, American cranberry, black
currants, guava fruit, papaya, cooked asparagus, tomato, Swiss cheese, Parmesan cheese, heated butter, cognac, Armagnac, rum and cider.
Definition
ChEBI: A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.
Definition
Two alcohols that are
derived from butane: the primary alcohol
butan-1-ol (CH3(CH2)2CH2OH) and the
secondary alcohol butan-2-ol
(CH3CH(OH)CH2CH3). Both are colorless
volatile liquids used as solvents.
Production Methods
The principal commercial source of 1-butanol is n-butyraldehyde
obtained from the oxo reaction of propylene,
followed by hydrogenation in the presence of a catalyst
. 1-Butanol has also been produced from
ethanol via successive dehydrogenation to acetaldehyde,
followed by an aldol process. The earliest commercial
route to 1-butanol, which is still used extensively
in many Third World countries, employs fermentation
of molasses or corn products with Clostridium acetobutylicum
.
Aroma threshold values
Detection: 500 ppb to 509 ppm
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Synthesis
n-Butyl alcohol is obtained by fermentation of glycerol, mannite, starches, and sugars in general, using Bacillus butylicus
sometimes synergized by the presence of Clostridium acetobutryricum; synthetically, from acetylene.
Source
1-Butanol naturally occurs in white mulberries and papaya fruit (Duke, 1992). Identified
as one of 140 volatile constituents in used soybean oils collected from a processing plant that fried
various beef, chicken, and veal products (Takeoka et al., 1996).
Environmental Fate
2Biological. 1-Butanol degraded rapidly, presumably by microbes, in New Mexico soils releasing
carbon dioxide (Fairbanks et al., 1985). Bridié et al. (1979) reported BOD and COD values of 1.71
and 2.46 g/g using filtered effluent from a biological sanitary waste treatment plant. These values
were determined using a standard dilution method at 20 °C for a period of 5 d. Heukelekian and
Rand (1955) reported a similar 5-d BOD value of 1.66 g/g which is 64.0% of the ThOD value of
2.59 g/g. Using the BOD technique to measure biodegradation, the mean 5-d BOD value (mM
BOD/mM 1-butanol) and ThOD were 3.64 and 60.7%, respectively (Vaishnav et al., 1987). In
activated sludge inoculum, following a 20-d adaptation period, 98.8% COD removal was
achieved. The average rate of biodegradation was 84.0 mg COD/g?h (Pitter, 1976).
Photolytic. An aqueous solution containing chlorine and irradiated with UV light (λ = 350 nm)
converted 1-butanol into numerous chlorinated compounds which were not identified (Oliver and Carey, 1977).
Reported rate constants for the reaction of 1-butanol and OH radicals in the atmosphere: 6.8 x
10-10 cm3/molecule?sec at 292 K (Campbell et al., 1976), 8.31 x 10-12 cm3/molecule?sec
(Wallington and Kurylo, 1987). Reported rate constants for the reaction of 1-butanol and OH
radicals in the atmosphere: 8.3 x 10-12 cm3/molecule?sec at 298 K (Atkinson, 1990); with OH
radicals in aqueous solution: 2.2 x 10-9 L/molecule?sec (OH concentration 10-17 M) (Anbar and
Neta, 1967). Based on an atmospheric OH concentration of 1.0 x 106 molecule/cm3, the reported
half-life of 1-butanol is 0.96 d (Grosjean, 1997).
Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor. Burns
with a strongly luminous flame (Windholz et al., 1983).
1-Butanol will not hydrolyze because it has no hydrolyzable functional group (Kollig, 1993).
At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent
concentration of 466 mg/L. The adsorbability of the carbon used was 107 mg/g carbon (Guisti et
al., 1974).
Purification Methods
Dry it with MgSO4, CaO, K2CO3, or solid NaOH, followed by refluxing with, and distillation from, small amounts of calcium, magnesium activated with iodine, or aluminium amalgam. It can also be dried with molecular sieves, or by refluxing with n-butyl phthalate or succinate. (For method, see Ethanol.) n-Butanol can also be dried by efficient fractional distillation, water passing over in the first fraction as a binary azeotrope (contains about 37% water). An ultraviolet-transparent distillate has been obtained by drying with magnesium and distilling from sulfanilic acid. To remove bases, aldehydes and ketones, the alcohol is washed with dilute H2SO4, then NaHSO4 solution; esters are removed by boiling for 1.5hours with 10% NaOH. It has also been purified by adding 2g NaBH4 to 1.5L butanol, gently bubbling with argon and refluxing for 1 day at 50o. Then adding 2g of freshly cut sodium (washed with butanol) and refluxed for 1day. Distil and collect the middle fraction [Jou & Freeman J Phys Chem 81 909 1977]. [Beilstein 1 IV 1506.]
Toxicity evaluation
The primary effects observed following oral and inhalation
exposure in rats and mice to n-butyl alcohol include neurological
and neurodevelopmental effects. n-Butyl alcohol has
been evaluated in a large number of experimental animal and
in vitro studies examining possible mechanisms for alcoholinduced
neurotoxicity. One proposed mechanism is that alcohols,
in general, produce neurological changes by disrupting
the lipid bilayer. A few experimental animal studies have
shown that n-butyl alcohol, like other alcohols, can disrupt
membrane integrity. Other in vitro and experimental animal
studies have demonstrated that n-butyl alcohol interacts with
protein-receptors and modulates their effects such that it
potentiates inhibitory g-aminobutyric acid (GABA) and glycine
receptors and inhibits excitatory neuronal receptors such
a glutamate. This modulatory action of n-butyl alcohol is
supportive of the observed neurobehavioral changes (e.g.,
central nervous system (CNS) depressant profile) associated
with n-butyl alcohol exposure in humans.
In addition, experimental animal studies have shown that
n-butyl alcohol inhibits fetal rat brain astroglial cell proliferation
by disrupting the phospholipase D (PLD) signaling
pathway. Inhibition of astroglial cell proliferation, which has
been postulated as a mode of action for ethanol-induced
microencephaly and mental retardation observed in cases of
fetal alcohol syndrome. These mechanisms can also be relevant
to the observed dilation in the brain that has been noted in
animals gestationally exposed to n-butyl alcohol.
