tert-Butanol

tert-Butanol Basic information
Product Name:tert-Butanol
Synonyms:t-Butyl Alcohol 〔2-Methyl-2-propanol〕;tert-Butanol EMPLURA.;tert-Butanol for analysis EMSURE ACS,Reag. Ph Eur;tert-ButanolACS reagent, ≥ 99.0% (GC);tert-Butanol, extra pure, 99.5%;tert-Butanol, for analysis ACS;tert-BUTYL ALCOHOL REAGENT (ACS);tert-Butanol 2-Methyl-2-propanol
CAS:75-65-0
MF:C4H10O
MW:74.12
EINECS:200-889-7
Product Categories:Organics;ACS and Reagent Grade Solvents;Carbon Steel Flex-Spout Cans;Plastic Bottles;ReagentPlus;ReagentPlus Solvent Grade Products;Semi-Bulk Solvents;Solvent Bottles;Solvent by Application;Solvent Packaging Options;Solvents;Anhydrous Solvents;Sure/Seal Bottles;Analytical Reagents;Analytical Reagents for General Use;Analytical/Chromatography;Histological Solvents;Puriss p.a. ACS;T-Z;75-65-0
Mol File:75-65-0.mol
tert-Butanol Structure
tert-Butanol Chemical Properties
Melting point 23-26 °C (lit.)
Boiling point 83 °C (lit.)
density 0.775 g/mL at 25 °C (lit.)
vapor density 2.55 (vs air)
vapor pressure 31 mm Hg ( 20 °C)
refractive index n20/D 1.399(lit.)
Fp 95 °F
storage temp. Store at +5°C to +30°C.
solubility water: miscible
pka19(at 25℃)
form Liquid After Melting
color APHA: ≤20
OdorCharacteristic; camphor-like; pungent.
PH Range7
Relative polarity0.389
Odor Threshold4.5ppm
explosive limit2.3-8.0%(V)
Water Solubility soluble
λmaxλ: 215 nm Amax: 1.00
λ: 230 nm Amax: 0.50
λ: 250 nm Amax: 0.20
λ: 300-350 nm Amax: 0.01
Merck 14,1542
JECFA Number85
BRN 906698
Henry's Law Constant1.22 at 25 °C (static headspace-GC, Merk and Riederer, 1997)
Exposure limitsTLV-TWA 300 mg/m3 (100 ppm) (ACGIH); IDLH 8000 ppm.
Stability:Stable. Very flammable. Incompatible with strong oxidizing agents, copper, copper alloys, alkali metals, aluminium.
InChIKeyDKGAVHZHDRPRBM-UHFFFAOYSA-N
LogP0.350
CAS DataBase Reference75-65-0(CAS DataBase Reference)
NIST Chemistry ReferenceEthanol, 1,1-dimethyl-(75-65-0)
EPA Substance Registry Systemtert-Butanol (75-65-0)
Safety Information
Hazard Codes Xn,F,T
Risk Statements 11-20-39/23/24/25-23/24/25-36/37
Safety Statements 9-16-45-36/37-7-46-26
RIDADR UN 1120 3/PG 3
WGK Germany 1
RTECS EO1925000
Autoignition Temperature896 °F
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29051410
Hazardous Substances Data75-65-0(Hazardous Substances Data)
ToxicityLD50 orally in rats: 3.5 g/kg (Schaffarzick, Brown)
IDLA1,600 ppm
MSDS Information
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tert-Butanol English
SigmaAldrich English
ACROS English
ALFA English
tert-Butanol Usage And Synthesis
Chemical Propertiestert-Butanol (CH3)3COH is a white crystalline solid or colorless liquid (above 77 °F) with a camphor-like odor (IPCS, 1987a; NIOSH, 2005). It is soluble in water and miscible with alcohol, ether, and other organic solvents (IPCS, 1987a). It is highly flammable and easily ignited by heat, sparks, or flames; vapors may form explosive mixtures with air. Fire and explosion may result from contact with oxidizing agents, strong mineral acids, or strong hydrochloric acid (NIOSH,1992).tert-butanol
tert-Butanol has been used for a variety of other purposes, including as a dehydrating agent and solvent. tert-butanol is a polar organic solvent that is used in such large scale applications as the manufacture of flavors, perfumes, and paint removers. It is also utilized as a denaturant for ethyl alcohol.
Tert-butanol is a metabolite of the gasoline additive methyl tert-butyl ether (MTBE).
tert-Butanol also is used to manufacture methyl methacrylate plastics and flotation devices. Cosmetic and food-related uses include the manufacture of flavors, and, because of its camphor-like aroma, it also is used to create artificial musk, fruit essences, and perfume (HSDB, 2007). It is used in coatings on metal and paperboard food containers (Cal/EPA, 1999) and industrial cleaning compounds, and can be used for chemical extraction in pharmaceutical applications (HSDB, 2007).
Physical propertiestert-Butanol is a colorless liquid or crystals with a camphor-like odor. A detection odor threshold concentration of 2,900 mg/m3 (957 ppmv) was experimentally determined by Dravnieks (1974). In a later study, Nagata and Takeuchi (1990) reported an odor threshold concentration 220 ppbv.
Usestert-Butanol is used as a solvent (e.g., for paints, lacquers, and varnishes); as a denaturant for ethanol and several other alcohols; as an octane booster in gasoline; as a dehydrating agent; as a chemical intermediate in the manufacturing of methyl methacrylate; and in the manufacturing of flotation agents, fruit essences, and perfumes.
Usestert-Butanol is used in the production of tert-butyl chloride, tert-butyl phenol, andisobutylene; in the preparation of artificial musk; and in denatured alcohols.
UsesPlastics, lacquers, cellulose esters, fruit essences, perfumes, and chemical intermediates; additive to unleaded gasoline
Production Methodstert-Butanol is produced as a by-product from the isobutane oxidation process for manufacturing propylene oxide. It is also produced by the acidcatalyzed hydration of isobutylene, a process no longer used in the United States.
DefinitionTert-butanol is a tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2. It has a role as a human xenobiotic metabolite. It derives from a hydride of an isobutane.
General DescriptionColorless oily liquid with a sharp alcohol odor. Floats and mixes with water. Produces irritating vapor. Freezing point is 78°F.
Air & Water ReactionsHighly flammable. Water soluble.
Reactivity ProfileAttacks 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-phenylm-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].
HazardIrritant to eyes and skin. Flammable, dan- gerous fire risk. Central nervous system impair- ment. Questionable carcinogen.
Health Hazardtert-Butanol is more toxic than secbutylalcohol but less toxic than the primaryalcohol. However, its narcotic actionis stronger than that of n-butanol. Inhalationmay cause drowsiness and mild irritationof the skin and eyes. Ingestion may produceheadache, dizziness, and dry skin.Acute oral LD50 value (rats): 3500 mg/kg.
Chemical ReactivityReactivity 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 ProfileModerately toxic by ingestion, intravenous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Dangerous fire hazard when exposed to heat or flame. Moderately explosive in the form of vapor when exposed to flame. Ignites on contact with potassium-sodum alloys. To fight fire, use alcohol foam, CO2, dry chemical. Incompatible with oxidizing materials, H202. See also n-BUTYL ALCOHOL and ALCOHOLS.
Potential Exposuretert-Butanol is 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.
CarcinogenicityThere were increased incidences of renal tubule adenoma and carcinoma in male rats, transitional epithelia hyperplasia of the kidney in male and female rats, follicular cell adenoma of the thyroid in female mice, and follicular cell hyperplasia of the thyroid and inflammation and hyperplasia of the urinary bladder in male and female mice. In addition, a slight increase in follicular cell adenoma or carcinoma of the thyroid (combined) in male mice may have been related to exposure to t-butyl alcohol. t-Butyl alcohol was inactive on mouse skin as a complete carcinogen or as a tumor promoter.
SourceDetected in a distilled water-soluble fraction of 94 octane unleaded gasoline at a concentration of 3.72 mg/L (Potter, 1996)
ShippingUN1120 Butanols, Hazard Class: 3; Labels: 3— Flammable liquid. UN1212 Isobutanol or Isobutyl alcohol, Hazard Class: 3; Labels: 3—Flammable liquid
Purification Methodstert-Butanol is synthesised commercially by the hydration of 2-methylpropene in dilute H2SO4. Dry it with CaO, K2CO3, CaSO4 or MgSO4, filter and fractionally distil it. Dry further by refluxing with, and distilling from, either magnesium activated with iodine, or small amounts of calcium, sodium or potassium, under nitrogen. Passage through a column of type 4A molecular sieve is another effective method of drying; as well as refluxing with tert-butyl phthalate or succinate. (For method see Ethanol.) Other methods include refluxing with excess aluminium tert-butylate, or standing with CaH2, and distilling as needed. Further purification is achieved by fractional crystallisation by partial freezing, taking care to exclude moisture. tert-Butyl alcohol samples containing much water can be dried by adding *benzene, so that the water distils off as a tertiary azeotrope, b 67.3o. Traces of isobutylene have been removed from dry tert-butyl alcohol by bubbling dry pre-purified nitrogen through for several hours at 40-50o before using. It forms azeotropic mixtures with a large number of compounds. It has also been purified by distillation from CaH2 into Linde 4A molecular sieves which had been activated at 350o for 24hours [Jaeger et al. J Am Chem Soc 101 717 1979]. [Beilstein 1 IV 1609.] Rapid purification: Dry tert-butanol over CaH2 (5% w/v), distil and store it over 3A molecular sieves.
Incompatibilitiestert-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).
Waste DisposalIncineration, or bury absorbed waste in an approved land fill.
Iodotrimethylsilane (Trifluoromethyl)trimethylsilane 2,2-Bis(hydroxymethyl)propionic acid METHYLPROPANOL 3-(Trifluoromethyl)benzaldehyde Trimethylolpropane 3-(trifluoromethyl) Cinnamaldehyde Buprofezin Basic Violet 1 tert-Butanol Butyl acrylate 2,6-Lutidine Sodium tert-butyl alcohol,tert-Butyl alcohol, sodium salt Methyl acrylate 1,1,1-Trichloro-tert-butyl alcohol,Trichloro-tert-butyl alcohol,BETA,BETA,BETA-TRICHLORO-TERT-BUTYL ALCOHOL,β, β, β-Trichloro-tert-butanol hemihydrate 1-Butanol DI-TERT-BUTYL ETHER 1-Propanol T-Butanol

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