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. |