Quick Search
1-butanol (n-butanol) (n-butanol), also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure.
Isomers of 1-butanol (n-butanol) (n-butanol) are isobutanol, butan-2-ol and tert-butanol.
The unmodified term butanol usually refers to the straight chain isomer.
CAS: 71-36-3
MF: C4H10O
MW: 74.12
EINECS: 200-751-6
Synonyms
alcoolbutylique(french);butanol(french);Butanol-1;Butanolen;Butanolo;butanols;butylalcohol(non-specificname);Butylowy alkohol
1-butanol (n-butanol) (n-butanol) occurs naturally as a minor product of the ethanol fermentation of sugars and other saccharides and is present in many foods and drinks.
1-butanol (n-butanol) (n-butanol) is also a permitted artificial flavorant in the United States, used in butter, cream, fruit, rum, whiskey, ice cream and ices, candy, baked goods, and cordials.
1-butanol (n-butanol) (n-butanol) is also used in a wide range of consumer products.
The largest use of 1-butanol (n-butanol) (n-butanol) is as an industrial intermediate, particularly for the manufacture of butyl acetate (itself an artificial flavorant and industrial solvent).
1-butanol (n-butanol) is a petrochemical derived from propylene.
Estimated production figures for 1997 are: United States 784,000 tonnes; Western Europe 575,000 tonnes; Japan 225,000 tonnes.
1-butanol (n-butanol) is a type of alcohol with four carbon atoms being contained per molecule.
1-butanol (n-butanol) molecular formula is CH3CH2CH2CH2OH with three isomers, namely iso-butanol, sec-butanol and tert-butanol.
1-butanol (n-butanol) is colorless liquid with alcohol odor.
1-butanol (n-butanol) has the boiling point of being 117.7 ℃, the density (20 ℃) being 0.8109g/cm3, the freezing point being-89.0 ℃, flash point being 36~38 ℃, self-ignition point being 689F and the refractive index being (n20D) 1.3993.
At 20 ℃, 1-butanol (n-butanol)'s solubility in water is 7.7% (by weight) while the water solubility in 1-butanol (n-butanol) was 20.1% (by weight).
1-butanol (n-butanol) is miscible with ethanol, ether and other kinds of organic solvents.
1-butanol (n-butanol) can be used as the solvents of a variety of paints and the raw material for producing the plasticizers, dibutyl phthalate.
1-butanol (n-butanol) can also be used for the manufacture of butyl acrylate, butyl acetate, and ethylene glycol butyl ether and also used as the extract of intermediates of organic synthesis and biochemical drugs and can also used in the manufacture of surfactants.
Its steam can form explosive mixtures with air with the explosion limit being 3.7%~10.2% (volume fraction).
1-butanol (n-butanol) was first discovered by C-A. Wurtz (French) from the fusel oil obtained from the fermentation process of alcohol in 1852.
In 1913, the British Strange-Graham Companies have used corn as raw material for production of acetone through the fermentation process with butanol being the main byproduct.
Later, due to the increasing demand for butanol, the fermentation production factory began to mainly synthesize n-butanol with acetone and ethanol being the major byproduct.
During the Second World War, the German chemical company (Ruhr) began to apply propylene carboxyl method for the production of 1-butanol (n-butanol).
With the rise of the oil industry in 1950s, the 1-butanol (n-butanol) synthesis method had gotten rapid development with the propylene carboxyl method having the fastest speed.
1-butanol (n-butanol) is a colourless flammable liquid with strong alcoholic odour.
1-butanol (n-butanol) is a highly refractive liquid and burns with a strongly luminous flame.
1-butanol (n-butanol) is incompatible with strong acids, strong oxidising agents, aluminium, acid chlorides, acid anhydrides, copper, and copper alloys.
1-butanol (n-butanol) has an extensive use in a large number of industries.
For instance, 1-butanol (n-butanol) is used as solvent in industries associated with the manufacturing of paints, varnishes, synthetic resins, gums, pharmaceuticals, vegetable oils, dyes, and alkaloids.
1-butanol (n-butanol) finds its use in the manufacture of artificial leather, rubber, plastic cements, shellac, raincoats, perfumes, and photographic films.
1-butanol (n-butanol) is a primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group.
1-butanol (n-butanol) it produced in small amounts in humans by the gut microbes.
1-butanol (n-butanol) has a role as a protic solvent, a human metabolite and a mouse metabolite.
1-butanol (n-butanol)It is a primary alcohol, a short-chain primary fatty alcohol and an alkyl alcohol.
1-butanol (n-butanol) Chemical Properties
Melting point: -90 °C (lit.)
Boiling point: 116-118 °C (lit.)
density: 0.81 g/mL at 25 °C (lit.)
vapor density: 2.55 (vs air)
vapor pressure: 6.7 hPa (20 °C)
FEMA: 2178 | BUTYL ALCOHOL
refractive index : n20/D 1.399(lit.)
Fp: 95 °F
storage temp.: Store at +5°C to +30°C.
solubility: water: soluble
form:Liquid
pka: 15.24±0.10(Predicted)
color: APHA: ≤10
Relative polarity: 0.586
PH: 7 (70g/l, H2O, 20℃)
Odor: Alcohol-like; pungent; strong; characteristic; mildly alcoholic, non residual.
Odor Threshold: 0.038ppm
Odor Type: fermented
biological source: synthetic
explosive limit: 1.4-11.3%(V)
Water Solubility:80 g/L (20 ºC)
Sensitive: Moisture Sensitive
λmax λ: 215 nm Amax: 1.00
λ: 220 nm Amax: 0.50
λ: 240 nm Amax: 0.10
λ: 260 nm Amax: 0.04
λ: 280-400 nm Amax: 0.01
Merck: 14,1540
JECFA Number: 85
BRN: 969148
Henry's Law Constant: 49.2 at 50 °C, 92.0 at 60 °C, 152 at 70 °C, 243 at 80 °C (headspace-GC, Hovorka et al., 2002)
Exposure limits: TLV-TWA 300 mg/m3 (100 ppm) (NIOSH), 150 mg/m3 (50 ppm) (ACGIH); IDLH 8000 ppm (NIOSH).
Dielectric constant: 17.1（25℃）
Stability: Stable. Incompatible with strong acids, strong oxidizing agents, aluminium, acid chlorides, acid anhydrides, copper, copper alloys. Flammable.
Cosmetics Ingredients Functions: DENATURANT
SOLVENT
PERFUMING
Cosmetic Ingredient Review (CIR): 1-butanol (n-butanol) (71-36-3)
InChI: 1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
InChIKey: LRHPLDYGYMQRHN-UHFFFAOYSA-N
LogP: 0.88
Surface tension: 23.476mN/m at 298.15K
CAS DataBase Reference:71-36-3(CAS DataBase Reference)
NIST Chemistry Reference: 1-butanol (n-butanol)(71-36-3)
EPA Substance Registry System: 1-butanol (n-butanol) (71-36-3)
ECETOC JACC REPORT: 1-butanol 1-butanol (n-butanol) (71-36-3)
1-butanol (n-butanol) is a colorless flammable liquid with a strong alcoholic odor.
1-butanol (n-butanol) is a highly refractive liquid and burns with a strongly luminous flame.
1-butanol (n-butanol) is incompatible with strong acids, strong oxidizing agents, aluminium, acid chlorides, acid anhydrides, copper, and copper alloys.
1-butanol (n-butanol) has extensive use in a large number of industries.
For instance, 1-butanol (n-butanol) is used as a solvent in industries associated with the manufacturing of paints, varnishes, synthetic resins, gums, pharmaceuticals, vegetable oils, dyes, and alkaloids.
1-butanol (n-butanol) is used in the manufacture of artificial leather, rubber, and plastic cements, shellac, raincoats, perfumes, and photographic films.
1-butanol (n-butanol) is a solvent, chemical intermediate and an additive in unleaded gasoline.
1-butanol (n-butanol) is a colorless, volatile liquid with a rancid sweet odor.
The air odor threshold of 1-butanol (n-butanol) was reported to be 0.83 ppm ; others have identified the minimum concentration with identifiable odor as 11 and 15 ppm.
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.
Odor threshold concentration in water is 500 ppb.
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.
Uses
1-butanol (n-butanol) is the most important in industries and the most extensively studied.
1-butanol (n-butanol) is a colorless liquid with a strong, mildly alcoholic odor.
1-butanol (n-butanol) is used in chemical derivatives and as a solvent for paints, waxes, brake fluid, and cleaners.
1-butanol (n-butanol) is the allowable food flavors documented in the "food additives health standards" of China.
1-butanol (n-butanol) is mainly used for the preparation of food flavors of bananas, butter, cheese and whiskey.
For the candy, the usage amount should be 34mg/kg; for baked foods, it1-butanol (n-butanol) should be 32mg/kg; for soft drinks, it should be 12mg/kg; for cold drinks, it should be 7.0mg/kg; for the cream, it should be 4.0mg/kg; for alcohol, it should be 1.0mg/kg.
1-butanol (n-butanol) is mainly used for the manufacture of the n-butyl plasticizers of phthalic acid, aliphatic dicarboxylic acid and phosphoric acid that are widely applied to various kinds of plastic and rubber products.
1-butanol (n-butanol) can also be used as the raw material of producing butyraldehyde, butyric acid, butyl-amine and butyl lactate in the field of organic synthesis.
1-butanol (n-butanol) can also be used as the extraction agent of oil, drugs (such as antibiotics, hormones and vitamins) and spices as well as the alkyd paint additives.
1-butanol (n-butanol) can be used as the solvent of organic dyes and printing ink and de-waxing agent.
1-butanol (n-butanol) is used in the production of butylacetate, butyl glycol ether, and plasticizerssuch as dibutyl phthalate; as a solvent in thecoating industry; as a solvent for extractionsof oils, drugs, and cosmetic nail products;and as an ingredient for perfumes and flavor.
1-butanol (n-butanol) occurs in fusel oil and as aby-product of the fermentation of alcoholicbeverages such as beer or wine.
1-butanol (n-butanol) is presentin beef fat, chicken broth, and nonfilteredcigarette smoke.
Industrial use
Constituting 85% of its use, 1-butanol (n-butanol) is mainly used in the production of varnishes.
1-butanol (n-butanol) is a popular solvent, e.g. for nitrocellulose.
A variety of butanol derivatives are used as solvents, e.g. butoxyethanol or butyl acetate. Many plasticizers are based on butyl esters, e.g., dibutyl phthalate.
The monomer butyl acrylate is used to produce polymers.
1-butanol (n-butanol) is the precursor to n-butylamines.
Biofuel
1-butanol (n-butanol) has been proposed as a substitute for diesel fuel and gasoline.
It is produced in small quantities in nearly all fermentations (see fusel oil).
Clostridium produces much higher yields of butanol. Research is underway to increase the biobutanol yield from biomass.
Butanol is considered as a potential biofuel (butanol fuel).
Butanol at 85 percent strength can be used in cars designed for gasoline without any change to the engine (unlike 85% ethanol), and it provides more energy for a given volume than ethanol, almost as much as gasoline.
Therefore, a vehicle using butanol would return fuel consumption more comparable to gasoline than ethanol.
Butanol can also be added to diesel fuel to reduce soot emissions.
The production of, or in some cases, the use of, the following substances may result in exposure to 1-butanol (n-butanol): artificial leather, butyl esters, rubber cement, dyes, fruit essences, lacquers, motion picture, and photographic films, raincoats, perfumes, pyroxylin plastics, rayon, safety glass, shellac varnish, and waterproofed cloth.
Production method
There are several methods for their preparation.
Fermentation
In the past, the production of butanol has also used potatoes, grain or sugar as raw material and through their hydrolysis fermentation.
The resulting product from the fermentation broth contains a butanol content of 54.8%~58.5%, acetone content of 30.9%~33.7%, and the ethanol content of 7.8%-14.2%.
With the development of petrochemical industry, fermentation method has been gradually phased out.
The reaction equation is as follows: (C6H10O5) n [n (H2O)] → [strain] n-C6H12O6 [fermentation] → CH3COCH3 + C4H9OH + C2H5OH
The resulted fermentation broth was further fractionated to obtain acetone, ethanol and n-butanol separately.
Acetaldehyde method
Take acetaldehyde as raw material, add dilute alkali solution to give 2-hydroxybutyraldehyde at temperature below 20 ℃ with the reaction being stopped upon reaching 50%.
Use alkali to neutralize the acid and recycle the unreacted acetaldehyde and extract the 2-hydroxybutyraldehyde.
Then use acidic catalyst such as sulfuric acid and acetic acid for dehydration to obtain crotonaldehyde at 105~137 ℃, then use copper complex catalyst for hydrogenation at 160~240 ℃ to obtain the crude butyraldehyde and 1-butanol (n-butanol) with distillation to obtain the products.
CH3CH = CHCHO + H2 [catalyst] CH3CH2CH2CHO + CH3CH2CH2CH2OH
Its synthesis method including the following several ways:
Fermentation and Propylene carbonyl synthesis
Put propylene, carbon monoxide and hydrogen to the catalytic bed for reaction with catalyst being zeolite for absorbing cobalt salt or fatty acid cobalt with the reaction temperature being 130~160 ℃ and the reaction pressure being 20~25MPa.
The reaction can generate n-butyraldehyde and iso-butyraldehyde with separation via distillation and further catalytic hydrogenation of the n-butyraldehyde to obtain the 1-butanol (n-butanol).
CH3CH2CH2CHO + H2 → CH3CH2CH2CH2OH
You can alternatively use low pressure method with first-step method of propylene, carbon monoxide and water for synthesizing the butanol with the reaction temperature being 100~104 ℃ and pressure being 1.5MPa.
1-butanol (n-butanol) applies the mixture of iron pentacarbonyl, n-butyl pyrrolidine and water.
However, the one-way conversion of the propylene is low with only 8% to 10%. Reaction equation: CH3CH = CH2 + 3CO + 2H2O → n-C4H9OH + 2CO2
Production Methods
The principal commercial source of 1-butanol (n-butanol) is n-butyraldehyde obtained from the oxo reaction of propylene, followed by hydrogenation in the presence of a catalyst.
1-butanol (n-butanol) has also been produced from ethanol via successive dehydrogenation to acetaldehyde, followed by an aldol process.
The earliest commercial route to 1-butanol (n-butanol), which is still used extensively in many Third World countries, employs fermentation of molasses or corn products with Clostridium acetobutylicum .
