butan-2-one
2-Butanone
CAS: 78-93-3
Molecular Formula: C4H8O
butan-2-one - Names and Identifiers
| Name | 2-Butanone |
| Synonyms | MEK 2-Butanone butan-2-one Ethyl methyl ketone Methyl ethyl ketone 2-Butanone (Controlled Chemical) METHYL ETHYL KETONE (MEK)(BUTANONE) METHYL ETHYL KETONE DISTILLED IN GLASS Ethyl methyl ketone~MEK~Methyl ethyl ketone |
| CAS | 78-93-3 |
| EINECS | 201-159-0 |
| InChI | InChI=1/C4H8O/c1-3-4(2)5/h3H2,1-2H3 |
butan-2-one - Physico-chemical Properties
| Molecular Formula | C4H8O |
| Molar Mass | 72.11 |
| Density | 0.805 g/mL at 25 °C (lit.) |
| Melting Point | -87 °C (lit.) |
| Boling Point | 80 °C (lit.) |
| Flash Point | 26°F |
| JECFA Number | 278 |
| Water Solubility | 290 g/L (20 ºC) |
| Solubility | Miscible with acetone, ethanol, benzene, ether (U.S. EPA, 1985), and many other solvents,particularly ketones and aldehydes |
| Vapor Presure | 71 mm Hg ( 20 °C) |
| Vapor Density | 2.49 (vs air) |
| Appearance | Solution |
| Color | Colorless |
| Odor | Sweet/sharp odor detectable at 2 to 85 ppm (mean = 16 ppm) |
| Exposure Limit | TLV-TWA, PEL 590 mg/m3 (200 ppm)(ACGIH, OSHA); STEL 885 mg/m3(300 ppm) (ACGIH); IDLH 3000 ppm(NIOSH). |
| Merck | 14,6072 |
| BRN | 741880 |
| pKa | 14.7 (quoted, Riddick et al., 1986) |
| PH | pH(1+4, 25℃):6.0～7.0 |
| Storage Condition | 2-8°C |
| Stability | Stable. Highly flammable. Incompatible with oxidizing agents, bases, strong reducing agents. Protect from moisture. |
| Explosive Limit | 1.8-11.5%(V) |
| Refractive Index | n20/D 1.379(lit.) |
| Physical and Chemical Properties | Colorless flammable liquid, acetone odor. melting point -85.9 ℃ boiling point 79.6 ℃ relative density 0.8054 refractive index 1.3788 flash point -6 ℃ solubility, ethanol and ether, miscible with oil. |
| Use | Dewaxing agent used as chemical solvent and lubricating oil |
butan-2-one - Risk and Safety
| Risk Codes | R11 - Highly Flammable R36 - Irritating to the eyes R66 - Repeated exposure may cause skin dryness or cracking R67 - Vapors may cause drowsiness and dizziness R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. |
| Safety Description | S9 - Keep container in a well-ventilated place. S16 - Keep away from sources of ignition. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN 1193 3/PG 2 |
| WGK Germany | 1 |
| RTECS | EL6475000 |
| TSCA | Yes |
| HS Code | 29141200 |
| Hazard Class | 3 |
| Packing Group | II |
| Toxicity | LD50 orally in rats: 6.86 ml/kg (Smyth) |
butan-2-one - Upstream Downstream Industry
| Raw Materials | Tert-butyl alcohol |
| Downstream Products | 2,3-Butanedione Benomyl Polyurethane 2-Butanone Dimethylglyoxime Methyl ethyl ketone peroxide |
butan-2-one - Nature
Open Data Verified Data
colorless transparent volatile liquid, acetone odor. Melting Point -85.9 ℃; Boiling point 79,6 ℃;30 ℃(15. 9kPa), relative density 0.8054 (20/4 ℃); Refractive index 1. 3788} flash point (Open Cup)-6 ℃; Spontaneous ignition point 515.6 ℃; Specific heat capacity 2.297kj/(kg. C), viscosity (20 C) 0.41mPa-s. Soluble in 4 parts of water, but the temperature increases when the solubility decreases, 20 ℃, water solubility of 26.8% (mass). Water in 2-butanone solubility of 11.8% (mass). Soluble in ethanol and ether, miscible with oil. With water to form an azeotrope, its boiling point of 74.3 deg C, containing methyl ethyl ketone 88.7%. The explosion limit in air is 1.97% to 10.1% (by volume).
Last Update：2024-01-02 23:10:35
butan-2-one - Preparation Method
Open Data Verified Data
The mixed C4 fraction containing butanol is reacted with sulfuric acid, diluted with water, hydrolyzed to form an aqueous solution of SEC-butanol, and then subjected to dehydration and purification to obtain SEC-butanol. Pure SEC-Butanol is dehydrogenated by catalysis of nickel or zinc oxide to obtain the finished product. Alternatively, n-butene direct hydration is used.
Last Update：2022-01-01 09:24:33
butan-2-one - Use
Open Data Verified Data
methyl ethyl ketone is mainly used as a solvent, such as for lubricating oil dewaxing, coating industry and a variety of resin solvents, vegetable oil extraction process and refining process of azeotropic distillation, its advantage is solubility, the volatility is lower than that of acetone, and it is a medium boiling point ketone solvent. Butanone is also an intermediate for the preparation of medicines, dyes, detergents, perfumes, antioxidants and certain catalysts, for the synthesis of anti-peeling agent methyl ethyl ketone oxime, polymerization catalyst methyl ethyl ketone peroxide, corrosion inhibitor methyl pentanol, etc, used in the electronics industry as a developer after lithography of integrated circuits. The electronic pure methyl ethyl ketone is applied to the developer of the lithography process of the electronic industry integrated circuit and the cleaning agent of the process.
Last Update：2022-01-01 09:24:34
butan-2-one - Safety
Open Data Verified Data
butanone is a low toxicity class, when inhaled vapor, can stimulate the eyes and nostril mucosa, and cause Head Pain. Severe poisoning can lead to numbness of hands and feet, long-term contact can cause dermatitis, the air concentration is allowed to be 200 × 10-6 away from the fire, dry place storage.
Last Update：2022-01-01 09:24:34
butan-2-one - Reference Information
| FEMA | 2170 | 2-BUTANONE |
| relative polarity | 0.327 |
| olfactory Threshold | 0.44ppm |
| Henry's Law Constant | 23.0 at 50.00 °C, 34.1 at 60.00 °C, 50.6 at 70.00 °C, 70.4 at 80.00 °C (headspace-GC, Hovorka etal., 2002) |
| LogP | 0.3 at 40℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| toxicity | GRAS(FEMA). Not specified by ADI (FAO/WHO,1994). LD502737mg/kg (rat, oral). |
| usage limit | FEMA(mg/kg): used as spice: Soft drink 70; Cold drink 270; Candy 100; baked goods 100. Moderate limits (FDA § 172.515,2000). |
| Use | used as a solvent for cellulose acetate, acrylic resin, alkyd resin, coating, ink, etc, lubricating Oil dewaxing agent, vulcanization accelerator, etc. used as a reagent for the determination of cadmium, copper and mercury, standard substances for chromatographic analysis and solvents for semiconductor lithography GB 2760-96 is defined as permitted flavorants. Mainly used in the preparation of cheese, coffee and banana flavor. It can also be used as an extraction solvent. methyl ethyl ketone is mainly used as a solvent, such as for lubricating oil dewaxing, coating industry and a variety of resin solvents, vegetable oil extraction process and refining process of azeotropic distillation, its advantage is the solubility, the volatility is lower than that of acetone, and it is a medium boiling point ketone solvent. Butanone is also an intermediate for the preparation of medicines, dyes, detergents, perfumes, antioxidants and certain catalysts, for the synthesis of anti-peeling agent methyl ethyl ketone oxime, polymerization catalyst methyl ethyl ketone peroxide, corrosion inhibitor methyl pentanol, etc, used in the electronics industry as a developer after lithography of integrated circuits. methyl ethyl ketone is a raw material for the preparation of acaricide pyrimidine. In addition, methyl ethyl ketone is mainly used as a solvent, such as dewaxing for lubricating oil, coating industry and a variety of resin solvents, azeotropic distillation for the extraction and purification of vegetable oils. Its advantages are strong solubility, low volatility than acetone, belonging to the boiling point ketone solvent; Methyl ethyl ketone is also the preparation of spices, antioxidants and some catalyst intermediates, synthesis of anti-peeling agent methyl ethyl ketone oxime, polymerization catalyst methyl ethyl ketone peroxide, A corrosion inhibitor, such as methyl pentynol, is also used as a developer after lithography of an integrated circuit. dewaxing agent used as chemical solvent and lubricating oil |
| production method | butanone is an important component of the distillate (xylan oil) of retorted Wood. Industrial production from SEC-butanol, butane, etc. (1) There are two methods of gas phase and liquid phase dehydrogenation. Gas phase dehydrogenation with zinc-copper alloy or zinc oxide as catalyst, temperature 400~500 ℃, atmospheric pressure; Liquid phase dehydrogenation with Raney nickel or copper chromite as catalyst, temperature 150 ℃. The liquid phase dehydrogenation reaction temperature and energy consumption are low, the yield is high, the catalyst life is long, and the separation process is simple. (2) butane liquid phase oxidation the main product of butane liquid phase oxidation is acetic acid, and the by-product is methyl ethyl ketone (about 16% of acetic acid production). The reaction temperature is 150~225 ℃, and the pressure is 4.0~8.0MPa. For example, the United Carbide Company of the United States, in, used this method to produce 226,000 tons of acetic acid, to obtain 36,000 tons of by-product methyl ethyl ketone. About 20% of butanone is currently produced in the United States using this method. At present, the methods under study and development are liquid phase oxidation of butene, isobutylbenzene method and so on. (3) butene liquid phase oxidation method is called the mutual Kerr method (Wacker method). The reaction was carried out at 90~120 ℃ and 1.0 ~ 2.0MPa with palladium chloride/copper chloride solution as catalyst. CH2 = CHCH2CH3[O2]→ ch3coch2ch3butene conversion is about 95%, butanone yield is about 88%, and the obtained reaction liquid is purified by distillation and the like to obtain a finished product. The process of this method is simple, but the equipment is seriously corroded, and heavy metals are required as catalysts. This method has not been applied to large-scale production. (4) isobutylbenzene method N-Butene and benzene by alkylation to generate isobutylbenzene, isobutylbenzene oxidation to generate hydrogen peroxide isobutylbenzene, finally with acid decomposition to get methyl ethyl ketone and phenol. The alkylation of benzene with aluminum chloride as catalyst, reaction temperature 50~70 ℃, isobutylbenzene; Isobutylbenzene in 110~130 ℃, 0.1 ~ 0.49MPa pressure, liquid phase oxidation of isobutylbenzene hydroperoxide; then in the presence of acid catalyst decomposition, in 20~60 deg C to extract concentrated oxidation liquid, methyl ethyl ketone and phenol, and finally separation and purification to obtain the finished product. This method is characterized by mild corrosion of process equipment, mild reaction conditions, and is conducive to industrialization. butanone is an important component of the distillate (xylan oil) of dry-distilled Wood. Industrial production from SEC-butanol, butane, etc. 1. Indirect hydration of sulfuric acid The mixed C4 fraction containing butanol is brought into contact with sulfuric acid to form acid sulfuric acid ester and Chinese sulfuric acid ester, then diluted with water, hydrolyzed to form secondary butanol aqueous solution, and then dehydrated and concentrated to obtain secondary butanol. Pure SEC-Butanol is dehydrogenated by catalysis of nickel or zinc oxide to obtain the finished product. This method is divided into two kinds of N-butene direct hydration method, one with resin as Catalyst, the other with Heteropoly acid as catalyst. SEC-butanol dehydrogenation method this process is divided into gas phase method and liquid phase method, and most of them adopt gas phase dehydrogenation process. That is, butyl alcohol is prepared by dehydrogenation under the action of dehydrogenation catalyst. 4. Gas phase oxidation of ethylene. Isobutylbenzene method of N-Butene and benzene by alkylation to generate isobutylbenzene, isobutylbenzene oxidation of hydrogen peroxide isobutylbenzene, finally with acid decomposition of methyl ethyl ketone and phenol. This method is characterized by: process equipment corrosion light, mild reaction conditions, is conducive to industrialization. It is obtained by hydrolyzing N-Butene and sulfuric acid, distilling off SEC-butanol, and then catalytically dehydrogenating. From the direct oxidation of butane. |
| category | flammable liquid |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 2737 mg/kg; Oral-mouse LD50: 3000 mg/kg |
| stimulation data | Skin-rabbit 500 mg/24 h moderate; eye-rabbit 80 Mg |
| explosive hazard characteristics | explosive when mixed with air |
| flammability hazard characteristics | in case of open flame, high temperature, flammable oxidant; Combustion stimulus smoke |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; Stored separately from oxidants and acids |
| extinguishing agent | dry powder, dry sand, carbon dioxide, foam, water mist |
| Occupational Standard | TWA 590 mg/m3; Tel 740 mg/m3 |
| spontaneous combustion temperature | 516°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
| immediate life-and health-threatening concentrations | 3,000 ppm |
Last Update：2024-04-09 20:48:19
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