| | Hexane Chemical Properties |
| Melting point | -95 °C | | Boiling point | 68.95 °C(lit.) | | density | 0.659 g/mL at 25 °C(lit.) | | vapor density | 3.5 (vs air) | | vapor pressure | 40 mm Hg ( 20 °C) | | refractive index | n20/D 1.388 | | Fp | 30 °F | | storage temp. | Store at +5°C to +30°C. | | solubility | Very soluble in ethanol, ethyl ether and chloroform. | | pka | >14 (Schwarzenbach et al., 1993) | | form | Liquid | | color | Colorless | | Specific Gravity | 0.660 (20/4℃) | | Relative polarity | 0.009 | | Odor | Mild gasoline-like odor detectable at 65 to 248 ppm | | Odor Threshold | 1.5ppm | | explosive limit | 1.0-8.1%(V) | | Water Solubility | insoluble | | λmax | λ: 200 nm Amax: ≤0.70
λ: 225 nm Amax: ≤0.10
λ: 250 nm Amax: ≤0.01 | | Merck | 14,4694 | | BRN | 1730733 | | Henry's Law Constant | 0.238, 0.413, 0.883, 0.768, and 1.56 at 10, 15, 20, 25, and 30 °C, respectively (EPICS, Ashworth
et al., 1988) | | Exposure limits | TLV-TWA 50 ppm (～175 mg/m3) (ACGIH),
500 ppm (～1750 mg/m3) (OSHA); IDLH
5000 ppm (NIOSH). | | Stability: | Stable. Incompatible with oxidizing agents, chlorine, fluorine, magnesium perchlorate. Highly flammable. Readily forms explosive mixtures with air. Note low flash point. | | InChIKey | VLKZOEOYAKHREP-UHFFFAOYSA-N | | LogP | 4 at 20℃ and pH7 | | CAS DataBase Reference | 110-54-3(CAS DataBase Reference) | | NIST Chemistry Reference | Hexane(110-54-3) | | EPA Substance Registry System | Hexane (110-54-3) |
| Provider | Language |
|
ALFA
| English |
| | Hexane Usage And Synthesis |
| Chemical Properties | n-Hexane is a highly flammable liquid, usually isolated from crude oil, and has extensive industrial applications as a solvent in adhesive bandage factories and other industries.
It is highly toxic, triggering several adverse health effects, i.e., nausea, skin irritation, dizziness, numbness of limbs, CNS depression, vertigo, and respiratory tract irritation to animals and humans. Occupational exposure of industrial workers has demonstrated motor polyneuropathy. Workers associated with long-term glue sniffi ng showed adverse effects in the form of degeneration of axons and nerve terminals.
| | Chemical Properties | n-Hexane is a highly flammable, colorless,
volatile liquid with a gasoline-like odor. The water/odor
threshold is 0.0064 mg/L and the air/odor threshold is
230 875 milligram per cubic meter. | | Physical properties | Clear, colorless, very flammable liquid with a faint, gasoline-like odor. An odor threshold
concentration of 1.5 ppmv was reported by Nagata and Takeuchi (1990). | | Uses | Determining refractive index of minerals; filling for thermometers instead of mercury, usually with a blue or red dye; extraction solvent for oilseed processing. | | Uses | Suitable for HPLC, spectrophotometry, environmental testing | | Uses | n-Hexane is a chief constituent of petroleumether, gasoline, and rubber solvent. It is usedas a solvent for adhesives, vegetable oils,and in organic analysis, and for denaturingalcohol. | | Definition | ChEBI: An unbranched alkane containing six carbon atoms. | | General Description | Clear colorless liquids with a petroleum-like odor. Flash points -9°F. Less dense than water and insoluble in water. Vapors heavier than air. Used as a solvent, paint thinner, and chemical reaction medium. | | Air & Water Reactions | Highly flammable. Insoluble in water. | | Reactivity Profile | HEXANE may be sensitive to light. Hexane may also be sensitive to prolonged exposure to heat. Hexane can react vigorously with oxidizing materials. This would include compounds such as liquid chlorine, concentrated O2, sodium hypochlorite and calcium hypochlorite. Hexane is also incompatible with dinitrogen tetraoxide. Hexane will attack some forms of plastics, rubber and coatings. . | | Hazard | Flammable, dangerous fire risk. | | Health Hazard | n-Hexane is a respiratory tract irritant andat high concentrations a narcotic. Its acutetoxicity is greater than that of n-pentane.Exposure to a concentration of 40,000 ppmfor an hour caused convulsions and death inmice. In humans a 10-minute exposure toabout 5000 ppm may produce hallucination,distorted vision, headache, dizziness, nausea,and irritation of eyes and throat. Chronicexposure to n-hexane may cause polyneuritis.
The metabolites of n-hexane injected inguinea pigs were reported as 2,5- hexanedioneand 5-hydroxy-2-hexanone, which arealso metabolites of methyl butyl ketone(DiVincenzo et al. 1976). Thus methyl butylketone and n- hexane should have similartoxicities. The neurotoxic metabolite, 2,5-hexanedione, however, is produced considerablyless in n-hexane. However, in the caseof hexane, the neurotoxic metabolite 2,5-hexanedione is produced to a much lesserextent. Continuous exposure to 250 ppmn-hexane produced neurotoxic effects in animals. Occupational exposure to 500 ppmmay cause polyneuropathy (ACGIH 1986).
Inhalation of n-hexane vapors have shownreproductive effects in rats and mice. | | Flammability and Explosibility | Hexane is extremely flammable (NFPA rating = 3), and its vapor can travel a
considerable distance to an ignition source and "flash back." Hexane vapor forms
explosive mixtures with air at concentrations of 1.1 to 7.5 % (by volume).
Hydrocarbons of significantly higher molecular weight have correspondingly higher
vapor pressures and therefore present a reduced flammability hazard. Carbon
dioxide or dry chemical extinguishers should be used for hexane fires. | | 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. | | Potential Exposure | n-Hexane is industrial chemical, emul sifier, in manufacture of plastics, resins; as a solvent, par ticularly in the extraction of edible fats and oils; as a
laboratory reagent; and as the liquid in low temperature
thermometers. Technical and commercial grades consist of
45 85% hexane, as well as cyclopentanes, isohexane, and
1% to 6% benzene. | | Carcinogenicity | Male rabbits exposed to
3000 ppm hexane (8 h/day, 6 days/week for 24 weeks)
developed papillary proliferation of nonciliated bronchiolar
cells. No tumors were found in mice painted with
hexane and croton oil as cocarcinogen, presumably for the
lifetime of each animal. Hexane is inactive as a tumorpromoting
agent. | | Source | In diesel engine exhaust at a concentration of 1.2% of emitted hydrocarbons (quoted,
Verschueren, 1983).
A constituent in gasoline. Harley et al. (2000) analyzed the headspace vapors of three grades of
unleaded gasoline where ethanol was added to replace methyl tert-butyl ether. The gasoline vapor
concentrations of hexane in the headspace were 4.31 wt % for regular grade, 3.74.8 wt % for midgrade,
and 2.3 wt % for premium grade.
Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without
catalytic converters were 1.82 and 268 mg/km, respectively (Schauer et al., 2002). | | Environmental fate | Biological. Hexane may biodegrade in two ways. The first is the formation of hexyl hydroperoxide,
which decomposes to 1-hexanol followed by oxidation to hexanoic acid. The other
pathway involves dehydrogenation to 1-hexene, which may react with water giving 1-hexanol
(Dugan, 1972). Microorganisms can oxidize alkanes under aerobic conditions (Singer and
Finnerty, 1984). The most common degradative pathway involves the oxidation of the terminal
methyl group forming 1-hexanol. The alcohol may undergo a series of dehydrogenation steps
forming a hexanal followed by oxidation to form hexanoic acid. The fatty acid may then be
metabolized by β-oxidation to form the mineralization products, carbon dioxide and water (Singer
and Finnerty, 1984).
Photolytic. An aqueous solution irradiated by UV light at 50 °C for 1 d resulted in a 50.51%
yield of carbon dioxide (Knoevenagel and Himmelreich, 1976). Synthetic air containing gaseous
nitrous acid and exposed to artificial sunlight (λ = 300–450 nm) photooxidized hexane into two
isomers of hexyl nitrate and peroxyacetal nitrate (Cox et al., 1980).
Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor. | | storage | hexane should be used only in areas free of ignition sources, and
quantities greater than 1 liter should be stored in tightly sealed metal containers in
areas separate from oxidizers. | | Shipping | UN1208 Hexanes, Hazard Class: 3; Labels:
3-Flammable liquid. | | Purification Methods | Purify as for n-heptane. Modifications include the use of chlorosulfonic acid or 35% fuming H2SO4 instead of conc H2SO4 in washing the alkane, and final drying and distilling from sodium hydride. Unsaturated impurities can be removed by shaking the hexane with nitrating acid (58% H2SO4, 25% conc HNO3, 17% water, or 50% HNO3, 50% H2SO4), then washing the hydrocarbon layer with conc H2SO4, followed by H2O, drying, and distilling over sodium or n-butyl lithium. It can also be purified by distillation under nitrogen from sodium benzophenone ketyl solubilised with tetraglyme. Also purify it by passage through a silica gel column followed by distillation [Kajii et al. J Phys Chem 91 2791 1987]. It is a FLAMMABLE liquid and a possible nerve toxin. [Beilstein 1 IV 338.] Rapid purification: Distil, discarding the first forerun and stored over 4A molecular sieves. | | Toxicity evaluation | Identification of 2,5-hexanedione as the major neurotoxic
metabolite of n-hexane proceeded rapidly after its discovery as
a urinary metabolite. 2,5-Hexanedione has been found to
produce a polyneuropathy indistinguishable from n-hexane.
2,5-Hexanedione is many times more potent than n-hexane,
the parent compound, in causing neurotoxicity in experimental
animals. It appears that the neurotoxicity of 2,5-hexanedione
resides in its γ-diketone structure since 2,3-, 2,4-hexanedione
and 2,6-heptanedione are not neurotoxic, while
2,5-heptanedione and 3,6-octanedione and other g-diketones
are neurotoxic. | | Incompatibilities | May form explosive mixture with air.
Contact with strong oxidizers may cause fire and explo sions. Contact with dinitrogen tetraoxide may explode @
28℃.Attacks some plastics, rubber and coatings. May
accumulate static electrical charges, and may cause ignition
of its vapors. | | Waste Disposal | Dissolve or mix the material
with a combustible solvent and burn in a chemical incinera tor equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed. |
| | Hexane Preparation Products And Raw materials |
| Raw materials | PETROLEUM ETHER-->Gas oils (petroleum), straight-run-->Hexane | | Preparation Products | L-Carnitine-L-tartrate-->1-(2-Methoxyphenyl)piperazine-->2-(2-ISOPROPYLPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE-->3-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID HYDRAZIDE-->[Bis(trifluoroacetoxy)iodo]benzene-->N-METHYL-O-TOLUIDINE-->3-ACETOXYBENZOIC ACID-->METHYL 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLATE-->2,5-Dichloroisonicotinic acid-->TERT-BUTYL 3-FORMYLPYRIDIN-4-YLCARBAMATE-->BIS(DIISOPROPYLAMINO)CHLOROPHOSPHINE-->2'-BROMOACETANILIDE-->(3-HYDROXYMETHYL-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER-->2-(4-chlorop henyl)-4，5-dihydro-1-methyl-5-(trifluoromethyl)-1H-pyr role-3-carbonitrile-->1 1'-BIS(DIPHENYLPHOSPHINO)FERROCENE-->4-BOCAMINO-NICOTINIC ACID-->1-DIPHENYLPHOSPHINO-1'-(DI-TERT-BUTYLPH&-->(1R,3S)-3-Aminocyclopentanecarboxylic acid-->5-Bromopicolinic acid-->CYANOMETHYLENETRIBUTYLPHOSPHORANE-->ETHYL 4-HYDROXY-7-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE-->3-CHLOROBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE-->3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLIC ACID-->TERT-BUTYL 4-FORMYL-2-METHOXYPHENYL CARB ONATE, 99-->1-Methyl-2-imidazolecarboxaldehyde-->1,2-Bis(dimethylsilyl)benzene-->3,4-DIHYDRO-2H-1,5-BENZODIOXEPINE-7-CARBALDEHYDE-->1,1'-BIS(DIISOPROPYLPHOSPHINO)FERROCENE-->(2,2-DIMETHYL-PROPYL)-HYDRAZINE-->1,1'-FERROCENEDICARBOXALDEHYDE-->(1R,4S)-4-Aminocyclopent-2-enecarboxylic acid-->Mono-caprylin glycerate-->CANOLA OIL-->5-Chloro-2-nitrobenzaldehyde-->BIS(DIETHYLAMINO)CHLOROPHOSPHINE-->RAPESEEDOIL,SUPERGLYCERINATED,FULLYHYDROGENATED-->Annatto-->Maize yellIow-->Pefurazoate |
|
