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CAS No.: | 78-93-3 |
---|---|
Name: | 2-Butanone |
Article Data: | 985 |
Molecular Structure: | |
Formula: | C4H8O |
Molecular Weight: | 72.1069 |
Synonyms: | 3-Butanone;Butanone;Ethyl methyl ketone;MEK;Superbutanox M 50;Methyl ethyl ketone;Ethylmethylketone;Methylpropanone;Metiletilchetone;MEK(Methyl Ethyl Ketone ); |
EINECS: | 201-159-0 |
Density: | 0.786 g/cm3 |
Melting Point: | -86 °C, 187 K, -123 °F |
Boiling Point: | 79.64 °C, 353 K, 175 °F |
Flash Point: | 9 °C |
Solubility: | 27.5 g/100 mL in water |
Appearance: | Colorless liquid |
Hazard Symbols: | F, Xi |
Risk Codes: | 11-36-66-67 |
Safety: | 9-16 |
Transport Information: | UN 1193 3/PG 2 |
PSA: | 17.07000 |
LogP: | 0.98540 |
iso-butanol
butanone
Conditions | Yield |
---|---|
With copper(II) permanganate In dichloromethane for 0.166667h; Product distribution; Ambient temperature; various secondary alcohols; var. reaction time and reflux temperature; | 100% |
Stage #1: iso-butanol; platinum at 90℃; for 0.166667h; Stage #2: With dihydrogen peroxide In water at 90℃; for 2h; Product distribution / selectivity; | 100% |
With dihydrogen peroxide; SiW9Al3 at 90℃; for 7h; | 99% |
Conditions | Yield |
---|---|
With hydrogen; palladium(II) complex of ferrocenylamine sulfide (2) In acetone under 4137.2 Torr; for 0.5h; or with catalyst 3; | 100% |
With Pd/C; hydrogen In chloroform at 20℃; under 760.051 Torr; for 2h; Catalytic behavior; regioselective reaction; | 100% |
With hydrogen; Pd-polymethylhydrosiloxane nanocomposite In benzene at 20℃; for 5h; | 95% |
Conditions | Yield |
---|---|
(sulphos)Rh(CO)2 In octane; water at 100℃; for 1h; Product distribution; Further Variations:; Solvents; autoclave; | 100% |
With [Ru(η3:η3-C10H16)Cl2(benzimidazole)] In glycerol at 75℃; for 0.333333h; Sealed tube; Inert atmosphere; Green chemistry; | 99% |
With C12H24O16Ru3*2H2O; sodium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 45h; Catalytic behavior; Solvent; Schlenk technique; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With caro's acid; silica gel In dichloromethane for 0.166667h; Heating; | 100% |
With bismuth(III) nitrate; silica gel In acetone for 0.75h; | 98% |
With clayfen (montmorillonite K-10, Fe(NO3)3*9H2O) for 0.0333333h; microwave irradiation; | 88% |
Conditions | Yield |
---|---|
With C61H98ClN3P2Ru In dichloromethane-d2 at 50℃; under 3040.2 Torr; for 6h; Reagent/catalyst; Time; | 100% |
Conditions | Yield |
---|---|
With aluminum oxide; tripropylammonium fluorochromate (VI) In dichloromethane for 1h; | 98% |
With periodic acid at 20℃; for 0.0166667h; | 98% |
With perchloric acid; dihydrogen peroxide; potassium bromide; ammonium molybdate tetrahydrate In water at 20℃; for 1h; | 98% |
SEC-BUTYLAMINE
butanone
Conditions | Yield |
---|---|
With zinc dichromate trihydrate at 20℃; grinding; neat (no solvent); chemoselective reaction; | 97% |
With 3-carboxypyridinium dichromate In acetonitrile at 20℃; for 0.166667h; | 96% |
With potassium permanganate; iron(II) sulfate In dichloromethane for 5h; Heating; | 85% |
Conditions | Yield |
---|---|
With indium(III) triflate; water; toluene-4-sulfonic acid In 1,2-dichloro-ethane for 6h; Sealed tube; Reflux; regioselective reaction; | 96% |
With sodium tetrachloroaurate(III); sulfuric acid In methanol; water at 75℃; for 2.5h; | 94.8% |
With sulfuric acid; mercury(II) sulfate | |
With tricalcium diphosphate; tricadmium phosphate; water at 375℃; |
Conditions | Yield |
---|---|
With N-iodo-succinimide In chlorobenzene for 0.166667h; Product distribution; Irradiation; degradation of other α-hydroxy carboxylic acid; different times of irradiation and solvents, degradation in the dark at ambient temp.; | 96% |
With manganese(III) oxide at 50 - 60℃; |
Conditions | Yield |
---|---|
With sodium chloride; tin(ll) chloride In tetrahydrofuran; water for 2h; Heating; further sodium halides or pseudo-halides and metal halides; | 96% |
With sodium tetrahydroborate; tin(ll) chloride In tetrahydrofuran for 2h; Heating; | 93% |
With sodium iodide; tin(ll) chloride In tetrahydrofuran; water for 2h; Heating; | 91% |
Community Right-To-Know List. EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.
OSHA PEL: TWA 200 ppm; STEL 300 ppm
ACGIH TLV: TWA 200 ppm; STEL 300 ppm; BEI: 2 mg(MEK)/L in urine at end of shift
DFG MAK: 200 ppm (600 mg/m3)
NIOSH REL: (Ketones) TWA 590 mg/m3
DOT Classification: 3; Label: Flammable Liquid
For occupational chemical analysis use OSHA: #16 or NIOSH: 2-Butanone, 2500.
2-Butanone, with the CAS register number 78-93-3, is an organic compound with the formula C4H8O. It can alo be called as Methyl ethyl ketone or MEK. 2-Butanone is colorless liquid ketone has a sharp, sweet odor which is soluble in water. In addition, it is stable and highly flammable, which is also incompatible with oxidizing agents, bases, strong reducing agents. However, 2-Butanone should be protected from moisture. 2-Butanone has the EINECS register number 201-159-0. Because 2-Butanone has carbonyl group and activehydrogen connected with carbonyl, it is easy to produce many sorts of reaction. 2-Butanone can be heated with hydrochloric acid or sodium hydroxide to react a condensation reactions to generate 3,4-dimethyl-3-hexen-2-one or 3-methyl-3-hepten-5-one. If exposed long time under sunshine, 2-Butanone will convert into ethane, acetic acid or condensation compound. In addition, 2-Butanone can be oxidized into biacetyl by nitric acid. It can also react with phenol to give 2,2-di(4-hydroxyphenyl)butane.
Physical properties about 2-Butanone are:
(1)ACD/LogP: 0.468; (2)ACD/LogD (pH 5.5): 0.47; (3)ACD/LogD (pH 7.4): 0.47; (4)ACD/BCF (pH 5.5): 1.34; (5)ACD/BCF (pH 7.4): 1.34; (6)ACD/KOC (pH 5.5): 42.81; (7)ACD/KOC (pH 7.4): 42.81; (8)#H bond acceptors: 1 ; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.367; (11)Molar Refractivity: 20.61 cm3; (12)Molar Volume: 91.682 cm3; (13)Polarizability: 8.17 10-24cm3; (14)Surface Tension: 21.0410003662109 dyne/cm; (15)Density: 0.787 g/cm3; (16)Flash Point: -3.333 °C; (17)Enthalpy of Vaporization: 31.3 kJ/mol; (18)Boiling Point: 75.621 °C at 760 mmHg; (19)Vapour Pressure: 114.517997741699 mmHg at 25°C
Preparation of 2-Butanone:
2-Butanone is biosynthesized by some trees and found in some fruits and vegetables in small amounts. 2-Butanone can also be produced by oxidation or dehydrogenation of 2-Butanol using a catalyst based on copper, zinc, or bronze:
CH3CH(OH)CH2CH3 + O2 → CH3C(O)CH2CH3
CH3CH(OH)CH2CH3 → CH3C(O)CH2CH3 + H2
Moreover, 2-Butanone is made by the sulfation and hydration of 1 or 2-butgne to sec-butyl alcohol, which is then dehydrogenated to the ketone.
CH3CH2CH=CH2 → CH3CH2CH(OH)CH3
CH3CH=CHCH3 → CH3CH2CH(OH)CH3
CH3CH2CH(OH)CH3 → CH3CH2C(=O)CH3
Uses of 2-Butanone:
2-Butanone is commonly used as an industrial solvent in processes involving gums, resins, cellulose acetate and nitrocellulose coatings and in vinyl films. For this reason, 2-Butanone was found use in the manufacture of plastics, textiles, in the production of paraffin wax, and in household products such as lacquer, varnishes, paint remover, a denaturing agent for denatured alcohol, glues, and as a cleaning agent. Because 2-Butanone dissolves polystyrene, it is used as a welding agent used in connecting together parts of scale model kits. 2-Butanone is the precursor to produce methyl ethyl ketone peroxide which is a catalyst for some polymerization reactions.
Safety information of 2-Butanone:
When you are using 2-Butanone, you should be cautious about it. The substance is highly flammable and irritant, which is irritating to eyes. If repeated exposure, 2-Butanone may cause skin dryness or cracking. Its vapours may cause drowsiness and dizziness. In addition, you should keep its container in a well-ventilated place and keep 2-Butanone away from sources of ignition - No smoking.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCC(=O)C
(2)InChI: InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
(3)InChIKey: ZWEHNKRNPOVVGH-UHFFFAOYSA-N
The toxicity data of 2-Butanone is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LDLo | intraperitoneal | 2gm/kg (2000mg/kg) | LIVER: OTHER CHANGES | Food and Cosmetics Toxicology. Vol. 15, Pg. 627, 1977. |
human | TCLo | inhalation | 100ppm/5M (100ppm) | 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 | 38gm/m3 (38000mg/m3) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986. | |
mouse | LC50 | inhalation | 32gm/m3/4H (32000mg/m3) | Current Toxicology. Vol. 1, Pg. 47, 1993. | |
mouse | LD50 | intraperitoneal | 616mg/kg (616mg/kg) | Shell Chemical Company. Unpublished Report. Vol. -, Pg. 6, 1961. | |
mouse | LD50 | oral | 4050mg/kg (4050mg/kg) | Toxicology Letters. Vol. 30, Pg. 13, 1986. | |
rabbit | LD50 | skin | 6480mg/kg (6480mg/kg) | Shell Chemical Company. Vol. MSDS-5390-4, | |
rat | LC50 | inhalation | 23500mg/m3/8H (23500mg/m3) | American Industrial Hygiene Association Journal. Vol. 20, Pg. 364, 1959. | |
rat | LD50 | intraperitoneal | 607mg/kg (607mg/kg) | Environmental Research. Vol. 40, Pg. 411, 1986. | |
rat | LD50 | oral | 2737mg/kg (2737mg/kg) | Toxicology and Applied Pharmacology. Vol. 19, Pg. 699, 1971. |