Related Searches: 4-Methyl-2-pentanone, 4-Hydroxy-4-methyl-2-pentanone, 2-Pentanone, 4-hydroxy-4-methyl-, 2-methyl-3-pentanone, 2-Pentanone, View all

4-Methyl-2-pentanone(CAS No. 108-10-1)

4-Methyl-2-pentanone C6H12O (cas 108-10-1) Molecular Structure

108-10-1 Structure

Identification and Related Records

【Name】
4-Methyl-2-pentanone
【Iupac name】
4-methylpentan-2-one
【CAS Registry number】
108-10-1
【Synonyms】
Isobutyl methyl ketone
Isopropylacetone
Methyl isobutyl ketone
MIBK
Hexone
Methyl isobutyl keton
Methyl isobuty ketone
【EINECS(EC#)】
203-550-1
【Molecular Formula】
C6H12O (Products with the same molecular formula)
【Molecular Weight】
100.16
【Inchi】
InChI=1/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3
【InChIKey】
NTIZESTWPVYFNL-UHFFFAOYSA-N
【Canonical SMILES】
CC(C)CC(=O)C
【MOL File】
108-10-1.mol

Chemical and Physical Properties

【Appearance】
Clear liquid
【Density】
0.7978
【Melting Point】
-84℃
【Boiling Point】
117.4℃
【Vapour】
18.2mmHg at 25°C
【Refractive Index】
1.395-1.397
【Flash Point】
14℃
【Water】
17 g/L (20℃)
【Solubilities】
Soluble
【Color/Form】
Colorless liquid
【Storage temp】
2-8°C
【Spectral properties】
SADTLER REF NUMBER: 23 (IR, GRATING)
Index of refraction: 1.3692 at 20 deg C/D
IR: 44 (Sadtler Research Laboratories Prism Collection)
UV: 21 (Sadtler Research Laboratories Prism Collection)
Raman: 987 (Sadtler Research Laboratories Prism Collection)
1H NMR: 139 (Varian Associates NMR Spectra Catalogue)
13C NMR: 139 (Varian Associates NMR spectra collectoin)
MASS: 53587 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
【Computed Properties】
Molecular Weight:100.15888 [g/mol]
Molecular Formula:C6H12O
XLogP3:1.3
H-Bond Donor:0
H-Bond Acceptor:1
Rotatable Bond Count:2
Tautomer Count:3
Exact Mass:100.088815
MonoIsotopic Mass:100.088815
Topological Polar Surface Area:17.1
Heavy Atom Count:7
Formal Charge:0
Complexity:64.6
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Hydrophobe Count:1
Effective Rotor Count:2
Conformer Sampling RMSD:0.4
CID Conformer Count:4

Safety and Handling

【Hazard Codes】
F:Flammable
【Risk Statements】
R11;R20;R36/37;R66
【Safety Statements 】
S16;S29;S9
【HazardClass】
3
【Safety】
Hazard Codes:F,Xn,T
Risk Statements:11-20-36/37-66-39/23/24/25-23/24/25
11:Highly Flammable
20:Harmful by inhalation
36/37:Irritating to eyes and respiratory system
66:Repeated exposure may cause skin dryness or cracking
39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed
23/24/25:Toxic by inhalation, in contact with skin and if swallowed
Safety Statements:9-16-29-45-36/37-7
9:Keep container in a well-ventilated place
16:Keep away from sources of ignition - No smoking
29:Do not empty into drains
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37:Wear suitable protective clothing and gloves
7:Keep container tightly closed
RIDADR:UN 1245 3/PG 2
WGK Germany:1
HazardClass:3
PackingGroup:II
Hazardous Substances Data:108-10-1(Hazardous Substances Data)
【PackingGroup 】
II
【Skin, Eye, and Respiratory Irritations】
The MIBK odor was objectionable and the vapor was irritating to the eyes at 200 ppm.
... /AT 100 PPM/ METHYL ISOBUTYL KETONE MAY IRRITATE EYES OF MORE SENSITIVE PERSON.
Contact or the Vapor can irritate the eyes, nose, mouth, and throat. Contact can irritate the skin.
Irritation of the eyes, skin, and respiratory tract, ... .
【Cleanup Methods】
Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. Oil-skimming equipment and sorbent foams can be applied to slick if done immediately. Keep this chemical out of a confined space ... because of the possibility of an explosion ... It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.
【Transport】
UN 1245
【Fire Fighting Procedures】
... Water should not be used, since this may cause the fire to spread, though a water spray can be used to cool containers.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.
Flammable. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. Wear goggles and self-contained breathing apparatus. Extinguish with dry chemical, alcohol foam, or carbon dioxide. Water may be ineffective on fire. Cool exposed containers with water.
【Fire Potential】
Flammable liquid when exposed to heat, flame, or oxidizers.
【Formulations/Preparations】
Grade: Technical, 98.5%.
/The NF grade/ ... contains not less than 99% of methyl isobutyl ketone.
MIBK IS FREQUENTLY BLENDED WITH METHYL ETHYL KETONE IN HIGH SOLIDS LACQUERS
4-Methyl-2-pentanone is available with a purity of >99%.
【DOT Emergency Guidelines】
/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution.
/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.
/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.
/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Evacuation: Large spill: Consider initial downwind evacuation for at least 300 meters (1000 feet). Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Fire: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or alcohol-resistant foam. Large fires: Water spray, fog or alcohol-resistant foam. Use water spray or fog; do not use straight streams. Move containers from fire area if you can do it without risk. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn.
/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces.
/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. 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. Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adherencing to skin. Keep victim warm and quiet. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
【Exposure Standards and Regulations】
Methyl isobutyl ketone is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.
Methyl isobutyl ketone is an indirect food additive for use only as a component of adhesives.
【Reactivities and Incompatibilities】
Able to form unstable and explosive peroxides on contact with air. Reacts violently with strong oxidizers, potassium tert-butoxide, strong acids, aliphatic amines, reducing agents.
Ignites on contact with potassium-t-butoxide ... May form explosive peroxides upon exposure to air. Can react vigorously with reducing material.
4-Methyl-2-pentanone had not been considered prone to autoxidation, but an explosion during prolonged and repeated aerobic hot evaporation of the solvent was attributed to formation and explosion of a peroxide.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Work practices and industrial hygiene techniques should minimize the volatilization of ketones in the workroom air in order to ensure that the exposure limits are not exceeded. /Ketones/
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to disperse vapors and dilute standing pools of liquid.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet should be immediately removed due to its flammability hazard (i.e., for liquids with a flash point
【Protective Equipment and Clothing】
Ventilation, local exhaust, or breathing protection. Protective gloves. Protective clothing. Safety spectacles.
... Safety equipment suppliers/manufacturers can provide recommendations on the most protective glove/clothing materials ... Teflon and Styrene-Butadiene Rubber are among the recommended protective materials. ...
Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles.
Breakthrough times less (usually significantly less) than one hour reported by (normally) two or more testers for natural rubber. Breakthrough times greater than one hour reported by (normally two or more testers for polyvinyl alcohol (PVA). No data for butyl rubber, neoprene (Neop), nitrile rubber, nitrile rubber/polyvinyl chloride, polyethylene (PE), chlorinated polyethylene (CPE), polyurethane (PU), polyvinyl chloride (PVC), styrene-butadiene rubber (SBR), and viton.
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Respirator Recommendations: Up to 500 ppm Assigned Protection Factor (APF) Respirator Recommendation APF = 10 Any chemical cartridge respirator with organic vapor cartridge(s). Substance reported to cause eye irritation or damage; may require eye protection. APF = 50 Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister. APF = 50 Any powered, air-purifying respirator with a tight-fitting facepiece and organic vapor cartridge(s). Substance reported to cause eye irritation or damage; may require eye protection. APF = 10 Any supplied-air respirator. Substance reported to cause eye irritation or damage; may require eye protection. APF = 50 Any self-contained breathing apparatus with a full facepiece.
Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions: Assigned Protection Factor (APF) Respirator Recommendation APF = 10,000 Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode. APF = 10,000 Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape conditions: Assigned Protection Factor (APF) Respirator Recommendation APF = 50 Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister/Any appropriate escape-type, self-contained breathing apparatus.
【Specification】

clear liquid
Safety Statements:9-16-29-45-36/37-7
9:Keep container in a well-ventilated place
16:Keep away from sources of ignition - No smoking
29:Do not empty into drains
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37:Wear suitable protective clothing and gloves
7:Keep container tightly closed
【Octanol/Water Partition Coefficient】
log Kow = 1.31
【Disposal Methods】
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U161 and F003, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
A good candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 deg C and a residence time of 0.1 to 2 seconds.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

By hydrogenation of mesityl oxide over nickel at 160-190 deg C, ... .
ACETONE IS TREATED WITH BARIUM HYDROXIDE TO YIELD DIACETONE ALCOHOL; THIS IS DEHYDRATED TO MESITYL OXIDE WHICH CAN BE HYDROGENATED TO SATURATE THE DOUBLE BOND AND PRODUCE METHYL ISOBUTYL KETONE.
/Methyl isobutyl ketone is prepared/ by reacting sodium acetoacetic ester with isopropyl bromide and treating the resulting 2-isopropyl-acetoacetic ester with dilute acid to saponify the ester and decarboxylate the resulting keto acid.
In /a/ ... three-step process acetone undergoes alkali-catalyzed condensation in the first step to form diacetone alcohol. Dehydration of the latter to mesityl oxide takes place in the liquid phase at 90-130 deg C over an acid catalyst, such as phosphoric or sulfuric acid, with high selectivity. Selective hydrogenation of the carbon-carbon double bond in mesityl oxide to give 4-methyl-2-pentanone may be carried out in both the liquid phase and the gas phase with various catalysts, preferably palladium. ... Dehydration and hydrogenation can also be combined into a single process step.
... /A/ two-step process is less important industrially. Acetone is converted in a single step to mesityl oxide, which is then hydrogenated to 4-methyl-2-pentanone in a second step. Catalysts such as copper chromite or zirconium phosphate are used for the condensation, and palladium on aluminum oxide for the hydrogenation. 4-Methyl-2-pentanol is formed as a byproduct.
For the single-step production of 4-methyl-2-pentanone from acetone and hydrogen a combination of a cation exchanger with palladium is generally used as catalyst. The acetone is fed with hydrogen over the palladium-charged catalyst at 130 deg C and 0.5 - 5.0 MPa. A selectivity of > 95% at a conversion of
More than 60 percent of MIBK production comes from aldol condensation of acetone and derivative intermediated diacetone alcohol and mesityl oxide. ... MIBK may also be produced from isopropanol in a mixed ketones process, with diisobutyl ketone and acetone as co-products.
There are two main routes leading to MIBK. The first one comes from acetone condensation through intermediates diacetone alcohol and mesityl oxide. MIBK is also produced from isopropanol in a mixed ketones process with disobutyl ketone (DIBK) and acetone as coproducts. Methyl isobutyl carbinol, DIBK and mesityl oxide are coproduced or recovered during MIBK production processes.
U.S. Exports

(1984) 7.22X10+9 g
(1987) 5.90X10+5 lb
(1988) 1.92X10+6 lb
1997 exports amounted to 46 million pounds and averaged 40 million pounds annually in the 1994-97 period
2001 exports amounted to 47 million pounds; 2002 exports amounted to 53 million pounds
U.S. Imports

(1984) 9.31X10+9 g
(1986) 1.25X10+7 lb
1997 imports amounted to 23 million pounds and averaged 20 million pounds annually in the 1994-97 period
2001 imports amounted to 26 million pounds; 2002 imports amounted to 32 million pounds
U.S. Production

(1984) 6.50X10+10 g
(1987) 1.51X10+8 lb
(1988) 2.0X10+8 lb
In 1987 ... US production was 70,000 tons.
US Production (1993): 6.806X10+7 kg
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >100 million - 500 million 1990 >100 million - 500 million 1994 >100 million - 500 million 1998 >100 million - 500 million 2002 >100 million - 500 million
2-Pentanone, 4-methyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
US Producers of methyl isobtyl ketone (MIBK); US capacity (1998): 210 million pounds/year US Producers of Methyl Isobutyl Ketone (MIBK) US Producer 1998 Capacity (million pounds/year) Union Carbide 75 Eastman Chemical 35 Shell Chemicals 100
US Producers of methyl isobtyl ketone (MIBK); US capacity (2003): 195 million pounds/year US Producers of Methyl Isobutyl Ketone (MIBK) US Producer 2003 Capacity (million pounds/year) Dow Chemical 75 Eastman Chemical 20 Shell Chemicals 100
Global capacity stood at 366,000 tonnes/year in 2005, of which 90,000 tonnes/year was in the US, followed by 84,000 tonnes/year in western Europe, 59,000 tonnes/year in Japan and 43,000 tonne/year in Asia-Pacific (excluding Japan). Global demand for MIBK in 2005 was 287,000 tonnes. Asia-Pacific is the largest consumer with demand of 78,500 tonnes/year, followed by the US with 62,000 tonnes/year, then western Europe with 56,000 tonnes/year. Major Global MIBK Capacity (thousand tonnes/year) Producer Capacity Argentina 7.7 Brazil 20 China 15 France 39 India 7 Japan 59 Mexico 27.2 Netherlands 45 South Africa 27.2 South Korea 17 Taiwan 7 United States 90
Consumption Patterns

65% AS SOLVENT FOR PROTECTIVE COATINGS, 5% AS SOLVENT FOR RARE METAL EXTRACTION; 5% EXPORTED; 25% FOR MISC APPLICATIONS INCLUDING DEWAXING OF MINERAL OILS AND IN THE MANUFACTURE OF ANTIBIOTICS (1971)
NITROCELLULOSE LACQUERS, 25%; OTHER COATINGS, INKS, LACQUERS, 30%; SOLVENT EXTRACTION, 10%; MIBC, 10%; METALURGICAL, 5%; EXPORT, 15%; MISC, 5% (1980)
CHEMICAL PROFILE: Methyl isobutyl ketone. Demand: 1986: 145 million lb; 1987: 148 million lb; 1991 /projected/: 155 million lb. (Includes exports; in addition, 12.5 million lb were imported in 1986).
Demand 1995: 175 million pounds; 2000: 175 million pounds.
Demand 1998: 180 million pounds; 1999: 180 million pounds; 2003: 190 million pounds (includes exports)
Demand 2001: 146 million pounds; 2002: 147 million pounds; 2006: 147 million pounds, projected (demand equals production plus imports ... less exports)
(1998) US demand (production plus imports ... less exports) Methyl Isobutyl Ketone Consumption Percent (%) Coatings solvent (nitrocllulose, vinyl and acrylic) 65 Chemical production, including rubber antioxidants and acetylenic surfactants 20 Solvent extraction 5 Miscellaneous 10
(2003) US demand (production plus imports ... less exports) Methyl Isobutyl Ketone Consumption Percent (%) Coatings solvent (nitrocellulose, vinyl and acrylic) 54 Rubber antiozonants 23 Acetylenic surfactants 11 Solvent extraction 6 Miscellaneous 6
MIBK's use as a solvent is fragmented to more than 40 applications. About 16% of global MIBK is used as a solvent in transportation, refurnishing and marine coatings; 8.2% in construction coatings; 7.5% in wood coatings and 7.1% in metal coatings. Globally, 64% of total MIBK output is consumed as a solvent, 18% as an extraction solvent, 10% as rubber processing chemicals and 3% as surfactants. Methyl Isobutyl Ketone Consumption Percent (%) Coatings solvent (nitrocllulose, vinyl and acrylic) 54 Rubber antiozonants 23 Acetylenic surfactants 11 Solvent extraction 6 Miscellaneous 6
【Sampling Procedures】
NIOSH 1300: Analyte: methyl isobutyl ketone; Sampler: Solid Sorbent Tube, (coconut shell charcoal, 100 mg/50 mg); Flow rate: 0.01-0.2 l/min; Vol: min: 1 l, max: 25 l; sample stability: unknown.
Activated charcoal, Ambersorb XE-348, and Amberlites XAD-2, XAD-4, and XAD-7 were evaluated as solid adsorbents for work-room air sampling of selected ketones including methyl isobutyl ketone. Activated charcoal had good capacity for the compounds investigated, but most ketones decomposed on this adsorbent during storage. Ambersorb XE-348 also showed good capacity for most of the ketones and decomposition was insignificant. [Levin JO, Carleborg L; Ann Occup Hyg 31 (1): 31-8 (1987)] PubMed Abstract

Biomedical Effects and Toxicity

【Pharmacological Action】
Vapor causes irritation of eyes and nose; high concentrations cause anesthesia and depression. Liquid dries out skin and may cause dermatitis; irritates eyes but does not injure them.
【Biomedical Effects and Toxicity】
... Eight male volunteers (18 to 35 years old; weights = 68-90 kg) /were exposed/ to MIBK (concentrations of 2.4 ppm [10 mg/cu m], 24.4 ppm [100 mg/cu m], and 48.8 ppm [200 mg/cu m]) for 2 hr during light physical exercise on three different occasions. Exposures took place in a 12 cu m exposure chamber. Pulmonary retention of MIBK was decreased as fairly constant throughout the exposure period. The relative pulmonary uptake increased linearly with increasing exposure concentrations. Average values for uptake were 0.2 mmol at 10 mg/cu m, 1.7 mmol at 100 mg/cu m, and 3.2 mmol at 200 mg/cu m. At the end exposure, blood concentrations of MIBK increased linearly with increasing uptake. No tendency toward saturation kinetics was observed over the range of doses tested. The apparent blood clearance was 1.6 L/hr/kg at all exposure concentrations. The concentration of MIBK in the urine was higher than that noted in arterial blood both at 0.5 hr and 3 hr after exposure. Only 0.04% of the total dose was eliminated unchanged in the urine within 3 hr post exposure. ...
Methyl isobutyl carbinol (MIBC) is an oxygenated solvent that is metabolized to methylisobutyl ketone (MIBK) and then to 4-hydroxymethyl-4-methyl-2-pentanone (HMP). Plasma levels of MIBC, MIBK and HMP were determined up to 12 hr after a single oral 5 mmol/kg dose of MIBC or MIBK to male rats. The major material in the plasma in both cases was HMP, with similar areas-under-the-curve (AUC) and C(max) at 9 hr after dosing. MIBK plasma levels and AUC were also comparable after MIBK or MIBC administration. MIBC AUC was only about 6% of the total material in the blood after MIBC, and insignificant after MIBK administration. No other metabolites were detected in the plasma under the analytical conditions used. The extent of metabolism of MIBC to MIBK, by comparing combined AUCs for MIBK and HMP, was at least 73%. ... [Gingell R et al; Toxicol Lett 136 (3): 199-204 (2003)] PubMed Abstract
Absorption occurs following oral, dermal and inhalation administration. In man, pulmonary absorption in volunteers was reported to be about 60%.
In studies of methyl isobutyl ketone (MiBK)-potentiated cholestasis induced by taurolithocholic acid (TLC) or manganese-bilirubin (Mn-BR) combinations, MiBK is usually given by gavage whereas industrial exposure to MiBK normally occurs by inhalation. The present study was conducted to verify if the route of administration could influence the potentiation. Male Sprague-Dawley rats were treated with MiBK for 3 days orally or by inhalation (4 hr/day). The minimal effective doses (MED) for potentiating both models of intrahepatic induced cholestasis were estimated to be 3 mmol/kg or 400 ppm for the oral or inhalation route, respectively. Groups of rats were treated with 0.5, 1, or 2 times the MED. Half of each group was sacrificed after the last MiBK administration to determine plasma concentrations of MiBK and its metabolites by gas-liquid chromatography. The other half was challenged 18 hr later with TLC (30 umol/kg) or a combination of manganese (4.5 mg/kg) and bilirubin (15 mg/kg). Bile flow was measured from 15 to 135 min after the cholestatic challenge. Rats exposed to MiBK orally or by inhalation exhibited an enhanced diminution in bile flow that was dose-dependent. With dosages of 3 mmol/kg po or 400 ppm by inhalation or more, diminution in bile flow was significantly different from control values. Comparisons between maximal bile flow decrease and MiBK plasma concentration showed that the severity of the hepatotoxic response was dependent on the plasma MiBK concentration, irrespective of the route of administration. [Duguay AB, Plaa GL; Fundam Appl Toxicol 21 (2): 222-7 (1993)] PubMed Abstract
Ketones are readily absorbed through the intact skin. Usually they are rapidly excreted ... in the expired air. /Ketones/
Continuous intravenous infusion of 0.478 umol/min methyl isobutyl ketone (MIBK) was performed for 30 min in pentobarbital-anesthetized guinea-pigs. Epicutaneous exposure for 150 min was carried out 2.5 hr later after administration of MIBK to a sealed glass ring on the clipped back of the animals. Arterial blood was analyzed for MIBK by gas chromatography. Blood clearance averaged 201 mL/min/kg body wt. A maximum percutaneous uptake of 1.1 umol/min/sq cm was reached 10-45 min after the onset of exposure and decreased to 0.56 umol/min/sq cm during the latter part of exposure. [Hjelm EW et al; Toxicol Lett 56 (1-2): 79-86 (1991)] PubMed Abstract
The toxicokinetics of methyl isobutyl ketone ... /was/ studied in human volunteers during inhalation exposure. The volunteers were exposed (2 hr, 50 W) in an exposure chamber on four different occasions to about 10, 100 and 200 mg/cu m MIBK and to a combination of about 100 mg/cu m MIBK and 150 mg/cu m toluene. The relative pulmonary uptake of MIBK was about 60% and the total uptake increased linearly with increasing exposure concentration. The concentration of MIBK in blood rose rapidly after the onset of exposure and no plateau level was reached during exposure. No tendency for saturation kinetics could be observed within the dose interval and the apparent blood clearance was 1.61/hr/kg at all exposure levels. The concentration of unchanged MIBK in the urine after exposure was proportional with the total uptake. Only 0.04% of the total MIBK dose was eliminated unchanged via the kidneys within 3 hr post exposure. The concn of the metabolites 4-hydroxy-4-methyl-2-pentanone and 4-methyl-2-pentanol were below the detection limit (5 nmol/L). [Hjelm EW et al; Int Arch Occup Environ Health 62 (1): 19-26 (1990)] PubMed Abstract
The toxicokinetics as well as irritative effects and CNS symptoms of methyl isobutyl ketone (MIBK) were studied in human volunteers during inhalation exposure. The volunteers were exposed (2 hr, 50 W) in an exposure chamber on four different occasions to about 10, 100 and 200 mg/cu m MIBK and to a combination of about 100 mg/cu m MIBK and 150 mg/cu m toluene. The relative pulmonary uptake of MIBK was about 60% and the total uptake increased linearly with increasing exposure concentration. The concentration of MIBK in blood rose rapidly after the onset of exposure and no plateau level was reached during exposure. No tendency for saturation kinetics could be observed within the dose interval and the apparent blood clearance was 1.61/hr/kg at all exposure levels. The concentration of unchanged MIBK in the urine after exposure was proportional with the total uptake. Only 0.04% of the total MIBK dose was eliminated unchanged via the kidneys within 3 hr post exposure. ... [Hjelm EW et al; Int Arch Occup Environ Health 62 (1): 19-26 (1990)] PubMed Abstract
/The authors/ evaluated the percutaneous absorption of MIBK using eight outbred female guinea pigs. Initially, to determine blood clearance values MIBK was infused into each animal at a rate 0.478 umol MIBK per minute, corresponding to 0.680 to 0.928 umol/minute/kg bw, for 30 minutes. The average blood clearance to MIBK was 201 mL/min/kg bw. ... A maximum percutaneous uptake rate of 1.1 umol/min/sq cm was reached at 10 to 45 min after the initiation of exposure. A decrease in the uptake rate to 0.56 umol/min/sq cm was noted during the latter part of exposure (75 to 135 min after the initiation of exposure).

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a log Kow of 1.31(2) and a regression-derived equation(3), indicates that methyl isobutyl ketone is expected to have high mobility in soil(SRC). Volatilization of methyl isobutyl ketone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 19.9 mm Hg(4), and water solubility, 19,000 mg/L(5). Methyl isobutyl ketone is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Methyl isobutyl ketone was shown to biodegrade at a rate of 0.24 1/hr using activated sludge(6). Methyl isobutyl ketone degrades under both aerobic and anaerobic conditions(7-10).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a log Kow of 1.31(2) and a regression-derived equation(3), indicates that methyl isobutyl ketone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.4X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 19.9 mm Hg(4), and water solubility, 19,000 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 9 hours and 6 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 2(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation of methyl isobutyl ketone occurs in both freshwater and seawater(8-11).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl isobutyl ketone, which has a vapor pressure of 19.9 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl isobutyl ketone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 27 hours(SRC), calculated from its rate constant of 1.41X10-11 cu cm/molecule-sec at 25 deg (3). The photochemical degradation products of methyl isobutyl ketone with hydroxyl radicals are acetone and 2-methylpropanal(4). Methyl isobutyl ketone in cyclohexane exhibits strong absorption of UV light >290nm(5), suggesting that methyl isobutyl ketone has the potential to undergo direct photolysis in the environment.

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