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2-Butanol

Physical and Chemical Properties Chemical Properties Uses Butanol isomers Laboratory method for preparing 2-butanol Production method Dangerous situations Incompatibility Storage Transport requirements Extinguish measures Hazards & Safety Information
2-Butanol
2-Butanol structure
CAS No.
78-92-2
Chemical Name:
2-Butanol
Synonyms
ccs301;CCS 301;2-BUTANOL;Butanol-2;s-Butanol;BUTAN-2-OL;sec-C4H9OH;SEC-BUTANOL;Butan-2-OlGr;dl-2-butanol
CBNumber:
CB0751661
Molecular Formula:
C4H10O
Formula Weight:
74.12
MOL File:
78-92-2.mol

2-Butanol Properties

Melting point:
−115 °C(lit.)
Boiling point:
98 °C(lit.)
Density 
0.808 g/mL at 25 °C(lit.)
vapor density 
2.6 (vs air)
vapor pressure 
12.5 mm Hg ( 20 °C)
refractive index 
n20/D 1.397(lit.)
Flash point:
80 °F
storage temp. 
Flammables area
solubility 
125g/l
form 
Liquid
color 
Colorless
Odor
Strong, pleasant.
Relative polarity
0.506
explosive limit
1.4-9.8%(V)
Water Solubility 
12.5 g/100 mL (20 ºc)
Sensitive 
Hygroscopic
Merck 
14,1541
BRN 
1718765
Exposure limits
TLV-TWA 450 mg/m3 (150 ppm) (NIOSH), 305 mg/m3 (100 ppm) (ACGIH); IDLH 10,000 ppm.
Stability:
Stable. Flammable. Substances to be avoided include acids, acid chlorides, acid anhydrides, oxidizing agents and halogens.
InChIKey
BTANRVKWQNVYAZ-UHFFFAOYSA-N
CAS DataBase Reference
78-92-2(CAS DataBase Reference)
NIST Chemistry Reference
2-Butanol(78-92-2)
EPA Substance Registry System
2-Butanol(78-92-2)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
  • NFPA
Hazard Codes  Xi
Risk Statements  10-36/37-67
Safety Statements  13-24/25-26-46-7/9
RIDADR  UN 1120 3/PG 3
WGK Germany  1
RTECS  EO1750000
Autoignition Temperature 761 °F
TSCA  Yes
HazardClass  3
PackingGroup  II
HS Code  29051490
Hazardous Substances Data 78-92-2(Hazardous Substances Data)
Toxicity LD50 orally in Rabbit: 6480 mg/kg LD50 dermal Rat > 2000 mg/kg
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H226 Flammable liquid and vapour Flammable liquids Category 3 Warning
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H336 May cause drowsiness or dizziness Specific target organ toxicity,single exposure; Narcotic effects Category 3 Warning P261, P271, P304+P340, P312,P403+P233, P405, P501
H361 Suspected of damaging fertility or the unborn child Reproductive toxicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
Precautionary statements:
P201 Obtain special instructions before use.
P202 Do not handle until all safety precautions have been read and understood.
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233 Keep container tightly closed.
P240 Ground/bond container and receiving equipment.
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P271 Use only outdoors or in a well-ventilated area.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353 IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313 IF exposed or concerned: Get medical advice/attention.
P337+P313 IF eye irritation persists: Get medical advice/attention.
P370+P378 In case of fire: Use … for extinction.
P405 Store locked up.
P403+P233 Store in a well-ventilated place. Keep container tightly closed.
P403+P235 Store in a well-ventilated place. Keep cool.
P501 Dispose of contents/container to..…

NFPA 704

Diamond Hazard Value Description
3
1 0
Health   1 Exposure would cause irritation with only minor residual injury (e.g. acetone, sodium bromate, potassium chloride)
Flammability   3 Liquids and solids (including finely divided suspended solids) that can be ignited under almost all ambient temperature conditions . Liquids having a flash point below 22.8 °C (73 °F) and having a boiling point at or above 37.8 °C (100 °F) or having a flash point between 22.8 and 37.8 °C (73 and 100 °F). (e.g. gasoline, acetone)
Instability   0 Normally stable, even under fire exposure conditions, and is not reactive with water (e.g. helium,N2)
Special  

(NFPA, 2010)

2-Butanol price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1081829 2-Butanol Pharmaceutical Secondary Standard; Certified Reference Material 78-92-2 3x1.2ml $67.5 2018-11-13 Buy
Sigma-Aldrich 19440 2-Butanol puriss. p.a., Reag. Ph. Eur., ≥99.5% (GC) 78-92-2 1l $65.4 2018-11-13 Buy
Alfa Aesar 041871 2-Butanol, anhydrous, 99%, packaged under Argon in resealable ChemSeal? bottles 78-92-2 1L $65.1 2018-11-16 Buy
Alfa Aesar 041871 2-Butanol, anhydrous, 99%, packaged under Argon in resealable ChemSeal? bottles 78-92-2 250ml $28.7 2018-11-16 Buy
Sigma-Aldrich 19440 2-Butanol puriss. p.a., Reag. Ph. Eur., ≥99.5% (GC) 78-92-2 250ml $28.2 2018-11-13 Buy

2-Butanol Chemical Properties,Uses,Production

Physical and Chemical Properties

2-butanol is also known as 2-butanol, methyl ethyl alcohol, chemical formula is CH3CH2CHOHCH3. Molecular weight is 74.12. It is colorless liquid with a strong aroma of mint, flammable, volatile, with optical activity. The molecule has a chiral carbon atom, can be present in three forms of right-handed body, left-handed body and racemic body, dl-body: the relative density is 0.8063. Melting point is-114.7 ℃. Boiling point is 99.5 ℃, 45.5 ℃ (7.999 × 103Pa). The flash point is 34 ℃. The refractive index is 1.3978. d-body: the relative density is 0.8080. Boiling point is 99.5 ℃. The flash point is 24 ℃. The refractive index is 1.3954. Specific rotation is + 13.9 °. l-body: the relative density is 0.8070. Boiling point is 99.5 ℃. The flash point is 28 ℃. The refractive index is 1.3955. Specific rotation is-13.51 ° (25 ℃). 2-butanol oxidation can generate methyl ethyl ketone and acetic acid. Slightly soluble in water (25 ℃ when 12.5ml/100ml), dissolved in acetone, benzene, miscible with ethanol and ether. This product interacts with water to form an azeotropic mixture, the product content is 68%, the total boiling point is 88.5 ℃. Rat oral is LD506480mg/kg. 2-butanol is the main raw material for producing methyl ethyl ketone, butyl acetate, sec-butyl acetate, and also used as a solvent and extraction agent, the raw materials of plasticizers, processing agents, herbicides, but also for synthesis of spices, flavors, coloring agents, wetting agent, cleaning agents and solvents of many natural resin, linseed oil and castor oil.

Chemical Properties

It is slightly sticky colorless flammable liquid, with a strong odor. Melting point is-114.7 ℃, the boiling point is 99.5 ℃, relative density (d204) is 0.808~0.809, the refractive index (nD25) is 1.3949, a flash point is 23.9 ℃. It is soluble in water, miscible in ethanol and ether.

Uses

1. Used as extraction solvent, spices.
2. 2-butanol is Used as a solvent, and chromatography reagents
3. 2-butanol is Used for the production of intermediates of methyl ethyl ketone, for the preparation of butyl acetate, sec-butyl, used as plasticizers, processing agents, herbicides, solvents and so on.
4. Used for the production of intermediates of methyl ethyl ketone, for the preparation of butyl acetate, sec-butyl.

Butanol isomers

Butanol is an important industrial raw material, also known as hydroxy butane, a monohydric alcohol, the lowest level alcohol for the same family which can have two or more isomers, butanol has four kinds of isomers, namely n-butanol, 2-butanol, tert-butanol and isobutanol. Relative molecular mass is 74.12. Butanol has the common property of alcohols, such as water-like, reacts with metal to produce alkoxide, reacts with halogen acid to produce halogenated hydrocarbons, dehydrates into alkenes, oxidation (or dehydrogenation) reaction to produce aldehydes and acids, and reacts with organic acids or oxygen-containing inorganic acid to generate ester and so on. In the four isomers, the toxicity of n-butanol is minimal, the toxicity of the other three is not large, but their irritation is great, with irritation to the skin and mucous membrane. Inhalation of large vapors can cause coma. The maximum allowable concentration at workplace is 100 × 10-6. Butanol can be directly used as a solvent, extraction agent, dehydrating agent, plasticizer, mineral processing agent, anti-aging agent, herbicide and so on.
Physical and chemical properties and toxicity of butanol are different due to isomers. The solubility in water depends on their structure, chemical properties depend on hydroxy location in alcohol: n-butanol and iso-butanol are primary alcohols, can be oxidized into the corresponding aldehyde or acid, sec-butyl alcohol is oxidized into the corresponding ketone, t-butanol is unsusceptible to oxidation.
Physicochemical properties comparison chart of 4 isomers of butanol
Physicochemical properties comparison chart of 4 isomers of butanol
Under dehydrating catalyst, butanol can produce butene, n-butanol and 2-butene can give 1-butene, 2-butene, 2-butanol can generate 2-butene, isobutanol and tert-butanol generate isobutylene. Under the catalyst of copper and silver, the dehydrogenation generates carbonyl compounds, n-butanol generates butyraldehyde, butanol generates methyl ethyl ketone, isobutanol generate isobutyraldehyde. Under the catalyst, air oxidation can generate acid. Catalyzed by a mineral acid, it reacts with organic acid to generate ester. Reaction with benzene, can generate butyl benzene. Butanol reacts with chlorine to generate butyraldehyde chloride. Under the action of the aluminum catalyst at 300~350 ℃, reacts with ammonia, n-butanol, iso-butanol and 2-butanol react with ammonia to generate butylamine, dibutylamine, tributylamine, t-butanol does not have this character. N-butanol and tert-butanol at 180 ℃ react with hydrogen sulfide to generate butyl mercaptan.
The above information were collated and edited by Xiaonan of Chemicalbook.

Laboratory method for preparing 2-butanol

1, As raw materials 2-butene reacts with sulfuric acid in concentrated sulfuric acid to produce sulfuric acid butyl ester, sulfuric acid ester is then hydrolyzed to produce 2-butanol, and then distillation purification.
Butanol is prepared from 2-butene as raw material
2, 2-butanone is used as raw material, under the action of a Grignard reagent, to prepare 2-butanol.
3, cis-2-butene is used as raw material, under the action of boron hydrides, to prepare d-or l-body.

Production method

After adsorption by butane of the cracking petroleum or natural gas in sulfuric acid, then hydrolyze with steam.

Dangerous situations

Prolonged inhalation is toxic, it irritates eye and skin. Flammable, flash point is 406 ℃, there is a greater risk of combustion. The allowable concentration in air of US is 100ppm (305mg/m3).

Incompatibility

Sec-butyl alcohol is incompatible with strong oxidizing agents.

Storage

It is Stored in metal drums, to prevent mechanical damage, best stored in a cool, dry and ventilated, non-flammable place, away from all possible sources of ignition, separated from strong oxidants.

Transport requirements

During transportation, "flammable liquid" shall be marked logo on the container. Others should be the same with "n-butanol".

Extinguish measures

When firing, dry powder fire extinguishing agent, fire-resistant foam or CO2 can be used. Water fighting is invalid, but spray with water in the fire container to keep it cool. If spills, and spills are not lighted, water mist can wash spray spills from the fire, and dilute to non-flammable mixtures. If necessary, water mist can be used to protect the operator to stop the leakage. Other items see the "n-butanol."

Hazards & Safety Information

Category: Flammable liquid
Toxicity grading: Poisoning
Acute toxicity
Oral-rat LD50: 6480 mg/kg, Intravenous-Mouse LD50: 764 mg/kg
Stimulus data
Eyes-rabbit 100 mg/24 hours    moderate, Skin-rabbit 500 mg/24 hr  mild
Hazardous characteristics
It is explosive when mixed with air, self-oxidized to form explosive peroxides.
Flammability hazard characteristics
in case of fire, high temperature, oxidant, it is flammable, burning to generate irritation smoke, spontaneous combustion in contact with chromium trioxide.
Storage characteristics
Treasury ventilation low-temperature drying, and it is stored from oxidants.
Extinguishing agent
Dry powder, water spray, carbon dioxide, foam
Professional standards
TWA 100 PPM (310 mg/m3)

Chemical Properties

Colourless liquid

Uses

Preparation of methyl ethyl ketone, sol- vent, organic synthesis, paint removers, industrial cleaners.

Uses

2-Butanol is used in the production of methylethyl ketone and sec-butyl acetate, as asolvent in lacquers and alkyd enamels, inhydraulic brake fluids, in cleaning compounds,and its xanthate derivatives in oreflotation.

Definition

ChEBI: A secondary alcohol that is butane substituted by a hydroxy group at position 2.

General Description

A clear colorless liquid with an alcohol odor. Flash point below 0 °F. Less dense than water. Vapors heavier than air. Soluble in water. Moderately irritates the eyes and skin. Prolonged and repeated contact may cause defatting and drying of the skin. Vapors may irritate the nose, throat and respiratory tract. May be harmful by ingestion.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

Attacks plastics. [Handling Chemicals Safely 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water (Merck 11th ed. 1989). Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73 1967; J, Org. Chem. 28:1893 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].

Hazard

Toxic, mutagenic, upper respiratory tract irritant, central nervous system impairment.

Health Hazard

Recommended Personal Protective Equipment: Organic vapor canister or air-supplied mask; chemical goggles or face splash shield; Symptoms Following Exposure: Headache, dizziness, and respiratory irritation. Liquid is severely irritating to the eyes and may cause eyeburn; General Treatment for Exposure: INHALATION: remove from exposure immediately; call a physician; if breathing is irregular or has stopped, start resuscitation and administer oxygen. INGESTION: induce vomiting and call a physician. EYES: flush with water for at least 15 min.; Toxicity by Inhalation (Threshold Limit Value): 150 ppm; Short-Term Exposure Limits: 200 ppm for 60 min.; Toxicity by Ingestion: Grade 1; LD50 = 5-15 g/kg (rat-single oral dose); Late Toxicity: None; Vapor (Gas) Irritant Characteristics: Vapors cause a slight smarting of the eyes or respiratory system if present in high concentrations. The effect is temporary; Liquid or Solid Irritant Characteristics: No appreciable hazard. Practically harmless to the skin; Odor Threshold: Data not available.

Health Hazard

Exposure to 2-butanol may cause irritationof the eyes and skin. The latter effect isproduced by its defatting action on skin. Thistoxic property is mild and similar to thatof other butanol isomers. High concentrationmay produce narcosis. The narcotic effect isstronger than that of n-butanol, probably dueto the higher vapor pressure of the secondaryalcohol.
The toxicity is lower than that of itsprimary alcohol analogue.
LD50 value, oral (rats): 6480 mg/kg.

Fire Hazard

Flash Point (°F): 15 ℃; Flammable Limits in Air (%): 1.7-9.0; Fire Extinguishing Agents: Carbon dioxide, dry chemical; Fire Extinguishing Agents Not To Be Used: Not pertinent; Special Hazards of Combustion Products: Not pertinent; Behavior in Fire: Not pertinent; Ignition Temperature (°F): 763; Electrical Hazard: Class I, Group D; Burning Rate: 3.1 mm/min.

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.

Safety Profile

Poison by intravenous and intraperitoneal routes. Mildly toxic by ingestion. Experimental reproductive effects. A skin and eye irritant. See also nBUTYL ALCOHOL and ALCOHOLS. Dangerous fire hazard when exposed to heat or flame. Auto-oxidizes to an explosive peroxide. Ignites on contact with chromium trioxide. To fight fire, use water spray, alcohol foam, CO2, dry chemical. Incompatible with oxidizing materials. When heated to decomposition it emits acrid smoke and fumes.

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.

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

Purification Methods

Purification methods are the same as for n-Butanol. These include drying with K2CO3 or CaSO4, followed by filtration and fractional distillation, refluxing with CaO, distillation, then refluxing with magnesium and redistillation, and refluxing with, then distilling from CaH2. Calcium carbide has also been used as a drying agent. The anhydrous alcohol is obtained by refluxing with sec-butyl phthalate or succinate. (For method see Ethanol.) Small amounts of alcohol can be purified via conversion to the alkyl hydrogen phthalate and recrystallisation [Hargreaves J Chem Soc 3679 1956]. For purification of optical isomers, see Timmermans and Martin [J Chem Phys 25 411 1928]. [Beilstein 2 III 1566.]

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.

2-Butanol Preparation Products And Raw materials

Raw materials

Preparation Products


2-Butanol Suppliers

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2-Butanol Spectrum


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