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71-36-3

Basic Information
CAS No.: 71-36-3
Name: Butanol
Article Data: 1216
Molecular Structure:
Molecular Structure of 71-36-3 (Butanol)
Formula: C4H10O
Molecular Weight: 74.1228
Synonyms: Butylalcohol (8CI);1-Butyl alcohol;Butanol;Butyl hydroxide;CCS 203;Hemostyp;Methylolpropane;NSC 62782;Propylcarbinol;n-Butanol;n-Butyl alcohol;
EINECS: 200-751-6
Density: 0.805 g/cm3
Melting Point: -89 °C
Boiling Point: 117.697 °C at 760 mmHg
Flash Point: 35 °C
Solubility: 80 g/L (20 °C) in water
Appearance: colourless liquid
Hazard Symbols: HarmfulXn, ToxicT, FlammableF
Risk Codes: 10-22-37/38-41-67-39/23/24/25-23/24/25-11
Safety: 13-26-37/39-46-7/9-45-36/37-16-7
Transport Information: UN 1120 3/PG 3
PSA: 20.23000
LogP: 0.77880
Synthetic route
123-72-8

butyraldehyde

71-36-3

butan-1-ol

Conditions
ConditionsYield
With Ipc2BOH In pentane at 25℃; for 6h;100%
With Ca2>2*THF In hexane at 20℃; for 0.5h; other carbonyl compounds, var. calcium tetrakis(alkoxy)alanates, solvents, times, temp.;99%
With hydrogen; aluminum oxide; copper at 150℃;99%
592-84-7

n-butyl formate

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogenchloride In acetone at 20℃; for 0.25h; Product distribution; other alkyl formates;100%
dodecacarbonyl-triangulo-triruthenium; P(C4H9)3 In pyridine at 180℃; for 8h;75%
With water; tetraphenylphosphonium bromide; triphenylphosphine; potassium hydroxide In dibutyl ether at 25℃; for 0.166667h;11%
106-88-7

ethyloxirane

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
With lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran at 15℃; for 0.25h; Product distribution; with other oxiranes;A 99%
B 1%
With zeolite supported zinc borohydride In tetrahydrofuran at 20℃; for 12h; Yield given. Yields of byproduct given;
1927-68-0

2-butoxytetrahydropyran

A

6581-66-4

2-methoxytetrahydropyran

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
With methanol; DOWEX 50 W-X2 cation exchange resin at 40℃; for 1.13333h;A n/a
B 99%
764-01-2

methyl propargyl alcohol

A

4088-60-2

cis-2-buten-1-ol

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A 99%
B n/a
1801-76-9

Tributoxyoxovanadium

200882-13-9

(3bR,4aR)-2-(3,4,4-trime-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)-ethanol

13968-48-4

17O-water

A

[V(17)O2((3bR,4aR)-2-(3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)-ethanol)(n-BuOH)]

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
In dichloromethane compd. prepd. by react. VO(On-Bu)3 with ligand in CH2Cl2; H2(17)O added to soln.; detn. by NMR;A 99%
B n/a
588-67-0

benzyl 1-butyl ether

A

108-88-3

toluene

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
With 0.5%Pd/TiO2; isopropyl alcohol In water at 24.84℃; for 2h; Inert atmosphere; Sealed tube; Irradiation;A 99%
B 99%
110-63-4

Butane-1,4-diol

A

96-48-0

4-butanolide

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; Cu-based catalyst at 190℃; Product distribution; Further Variations:; Temperatures; reaction in vapour phase, fixed bed reactor;A 98.8%
B 0.8%
110-16-7

maleic acid

A

109-99-9

tetrahydrofuran

B

96-48-0

4-butanolide

C

67-56-1

methanol

D

110-63-4

Butane-1,4-diol

E

617-48-1

malic acid

F

110-15-6

succinic acid

G

64-19-7

acetic acid

H

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.45%
B 0.06%
C 0%
D 0.21%
E 0.36%
F 98.73%
G 0.04%
H 0.08%
107-92-6

butyric acid

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen at 265℃; for 3480h; Reagent/catalyst; Time;98%
With water In aq. phosphate buffer at 20℃; pH=7.4; Electrolysis; Inert atmosphere; Enzymatic reaction;98.5%
With diphenylamine borane In tetrahydrofuran 1.) 0 deg C, 1 h, 2.) 20 deg C, 1 h;61%
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Specification

1-Butanol, also known as butyl alcohol, is a colourless, flammable, volatile liquid with a strong alcoholic odor. It is a four carbon straight chain alcohol. 1-Butanol is slightly soluble in water, miscible with alcohol, ether, benzene and other organic solvents, so it can dissolve alkaloids, camphor, dyes, rubber, ethyl cellulose, grease, wax and a variety of natural and synthetic resins. Naturally, 1-Butanol occurs as a minor product of the fermentation of sugars and other carbohydrates. And it is also present in many foods and beverages. 

Preparation of 1-Butanol:
There are three industry factures of 1-butanol: fermentation, propylene carbonyl synthesis and acetaldehyde aldol condensation.
Fermentation: The grain, cereals, potato or molasses and other raw materials are crushed and adding water to obtain fermentation liquor. After high pressure steam sterilization process, cooled and put in pure acetone - butanol bacteria. Then ferment at 36-37 °C. Fermentation genetates gas containing carbon dioxide and hydrogen generation. The fermentation liquor contains ethanol, butanol and acetone with the ratio of 6:3:1. People can seperate butanol, acetone and ethanol by rectification.
Propylene carbonyl synthesis: The carbon monoxide and hydrogen which are made from coke and propylene go through carbonyl synthesis reaction at high pressure in the presence of cobalt-based or rhodium-based catalyst to get n-butanal and isobutyraldehyde. Then, after hydrogenation and fractionation, 1-butanol can be obtained.
Acetaldehyde aldol condensation: The condensation and dehydration of two molecules of acetaldehyde can obtain crotonaldehyde. Crotonaldehyde can be hydrogenated to produce 1-butanol in the presence of nickel-chromium catalyst at 180 °C and 0.29MPa.

Uses of 1-Butanol:
1-Butanol is used as solvent for paints, coatings, resins, gums, dyes, varnishes, vegetable oils, waxes, dyes, fats, rubbers, resins, shellac, camphor, and alkaloids. It is also used as dehydrating agent, anticreaming agent, extractant of drugs (such as antibiotics, hormones and vitamins) and spices, additive of alkyd paint, etc. As a solvent, 1-butanol is used to separate potassium perchlorate and sodium perchlorate, and sodium chloride and lithium chloride. What's more, it is mainly used in the manufacture of phthalic acid, aliphatic dicarboxylic acid and phosphoric acid butyl acetate plasticizers which are widely used in a variety of plastic and rubber products. Besides, it is also used as a diluent/reactant in the manufacture of urea–formaldehyde and melamine–formaldehyde resins. In addition, it is allowed as artificial flavorant in the United States, used in ice cream and ices, cream, fruit, rum, baked goods, whiskey, candy, butter, and cordials.

Safty informaition of 1-Butanol:
1-Butanol is not only harmful if swallowed, but also irritating to respiratory system and skin. It also has risk of serious damage to the eyes. Vapours may cause drowsiness and dizziness. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If swallowed, seek medical advice immediately and show this container or label. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) But no deaths were reported at an inhaled concentration of 8000 ppm (4-hour exposure, rats). Keep 1-butanol away from food, drink and animal foodstuffs.

Structure Descriptors:
1. Smiles:C(CC)CO
2. InChI:InChI=1/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3

Toxicity of 1-Butanol are as follows: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 2500mg/kg (2500mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat LDLo intravenous 243mg/kg (243mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 16, Pg. 1, 1920.
dog LDLo oral 1760mg/kg (1760mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: HEMORRHAGE
Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 81, Pg. 192, 1875.
dog LDLo subcutaneous 2gm/kg (2000mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: HEMORRHAGE
Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 81, Pg. 192, 1875.
human TCLo inhalation 25ppm (25ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 282, 1943.
mammal (species unspecified) LC50 inhalation 28400mg/m3 (28400mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.
mouse LD50 intraperitoneal 254mg/kg (254mg/kg) LIVER: OTHER CHANGES Research Communications in Chemical Pathology and Pharmacology. Vol. 26, Pg. 75, 1979.
mouse LD50 intravenous 377mg/kg (377mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 330, 1962.
mouse LD50 oral 2680mg/kg (2680mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(11), Pg. 57, 1981.
mouse LD50 subcutaneous 3200mg/kg (3200mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rabbit LD50 oral 3484mg/kg (3484mg/kg) SENSE ORGANS AND SPECIAL SENSES: CORNEAL DAMAGE: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

CARDIAC: PULSE RATE
Industrial Medicine and Surgery. Vol. 41, Pg. 31, 1972.
rabbit LD50 skin 3400mg/kg (3400mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 10, 1974.
rabbit LDLo unreported 3500mg/kg (3500mg/kg)   Therapeutische Monatshefte. Vol. 6, Pg. 327, 1892.
rat LC50 inhalation 8000ppm/4H (8000ppm)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 10, 1974.
rat LD50 intraperitoneal 1122mg/kg (1122mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
rat LD50 intravenous 310mg/kg (310mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
rat LD50 oral 790mg/kg (790mg/kg) LIVER: FATTY LIVER DEGERATION

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

BLOOD: OTHER CHANGES
South African Medical Journal. Vol. 43, Pg. 795, 1969.

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