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Home > Encyclopedia > Mesityl oxide

Mesityl oxide

Mesityl oxide structure

Mesityl oxide 

structure
  • CAS No:

    141-79-7

  • Formula:

    C6H10O

  • Chemical Name:

    Mesityl oxide

  • Synonyms:

    3-Penten-2-one,4-methyl-;4-Methyl-3-penten-2-one;Isobutenyl methyl ketone;Isopropylideneacetone;Mesityl oxide;Methyl isobutenyl ketone;2-Methyl-2-penten-4-one;4-Methyl-3-pentene-2-one;Methyl 2-methyl-1-propenyl ketone;Methyl 2,2-dimethylvinyl ketone;2-Methyl-4-oxo-2-pentene;2,2-Dimethylvinyl methyl ketone;NSC 38717

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

Oily, colorless to light-yellow liquid with a peppermint- or honey-like odor.


Mesityl oxide is a α,β-Unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a strong cat urine odor.


Mesityl oxide appears as a colorless, oily liquid with a pungent honey-like odor. Flash point 87°F. Less dense than water and slightly soluble in water. Vapors heavier than air. Used in paint removers, as a solvent for plastics, and as an insect repellent.|Liquid|COLOURLESS VISCOUS LIQUID WITH CHARACTERISTIC ODOUR. DARKENS ON STANDING.|Colourless oily liquid; unpleasant grassy-green or pungent, acrylic odour|Oily, colorless to light-yellow liquid with a peppermint- or honey-like odor.


Mesityl oxide appears as a colorless, oily liquid with a pungent honey-like odor. Flash point 87°F. Less dense than water and slightly soluble in water. Vapors heavier than air. Used in paint removers, as a solvent for plastics, and as an insect repellent.|4-Methyl-3-penten-2-one, 9CI is an olefinic compound. It derives from an acrylic acid.

Mesityl oxide Basic Attributes

98.14

98.14

1361550

205-502-5

77LAC84669

0814

38717

1229

DTXSID1029170

Oily, colorless to light-yellow liquid

2914190090

Characteristics

17.1

1.7

Clear Liquid, Free Of Suspended Matter

0.8592 g/cm3 @ Temp: 15 °C

-52.9 °C

130 °C @ Press: 760 Torr

87 °F

1.418

H2O: 28 G/L (20 ºC)

Flammables area

Vapour pressure, kPa at 20°C: 1.2

Relative vapour density (air = 1): 3.4

Oral-rat LD50: 1120 mg/kg; Oral-Mouse LD50: 710 mg/kg

It is flammable in case of open flame, high temperature and oxidant; steam is irritating; burning produces irritating smoke

1.4-10.1%(V)

... spearmint ...

OILY TASTE

Henry's Law constant = 3.67X10-5 atm-cu m/mole at 20 °C (est)

May darken upon standing|Max vapor concn: 12,3000 ppm at 20 °C|Conversion factors: 1 ppm = 4.02 mg/cu m; 1 mg/L = 249 ppm|Hydroxyl radical reaction rate constant = 7.86X10-11 cu cm/molecule-sec at 25 °C (est)

Highly flammable. Slightly soluble in water

Ketones

Highly Flammable

Mixing MESITYL OXIDE in equal molar proportions with any of the following substances in a closed container caused the temperature and pressure to increase: 2-aminoethanol, chlorosulfonic acid, ethylene diamine, nitric acid, oleum, or sulfuric acid [NFPA 1991].

652 °F (USCG, 1999)|652 °F (344 °C)|340 °C

-14,400 BTU/LB= -8,000 CAL/G= -330X10+5 JOULES/KG

9.08 eV

Lower flammable limit: 1.4% by volume; Upper flammable limit: 7.2% by volume|Class IC Flammable Liquid: Fl.P. at or above 73°F and below 100°F.

157 BTU/LB= 87 CAL/G= 3.7X10+5 JOULES/KG

Safety Information

III

3

UN 1229 3/PG 3

1

10-20/21/22-36/37/38

25

SB4200000

Xn

Treasury is ventilated, low temperature and dry; stored separately from oxidant

Explosive when mixed with air

P261-P280-P305 + P351 + P338-P311

H226-H302 + H312-H315-H319-H331-H335

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Mixing mesityl oxide and 2-aminoethanol /or chlorosulfonic acid or ethylene diamine or nitric acid or oleum or sulfuric acid/ in closed container caused temp and pressure to incr.|Oxidizers, acids.|... Attacks many plastics.

UN 1229

Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. (USCG, 1999)|Flammable. Above 25 °C explosive vapour/air mixtures may be formed.|Flammable - 3rd degree, Reactive - 1st degree

|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P322, P330, P363, P370+P378, P403+P235, and P501|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|Aggregated GHS information provided by 1678 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P311, P312, P314, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P311, P312, P314, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. 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. (ERG, 2016)

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: 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 SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet should be immediately removed due to its flammability hazard(i.e. for liquids with flash point Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear full protective clothing and positive pressure self-contained breathing apparatus.|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]|For more Personal Protective Equipment (PPE) (Complete) data for MESITYL OXIDE (10 total), please visit the HSDB record page.|(See protection codes)

Flammable liquid.|Dangerous, when exposed to heat or flame; can react with oxidizing materials

Above 25 °C explosive vapor/air mixtures may be formed ... /Mesityl oxide/ can presumably form explosive peroxides.|MAY EXPLODE IF IGNITED IN AN ENCLOSED AREA. CONTAINERS MAY EXPLODE IN FIRE.|Explosive limits , vol% in air: 1.4-10.1

Use dry chemical, foam, carbon dioxide, or water spray. Water may be ineffective. Use water spray to keep fire-exposed containers cool.|If material /is/ 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 spread fire. 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.|Aqueous film-forming foam (AFFF), alcohol-resistant foam, powder, carbon dioxide.

A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.|Vapors are heavier than air (vapor-air density at 100 °F, 1.1) and may travel to a source of ignition and flash back.

Eliminate all ignition sources. Stop or control the leak, if it can be done without undue risk. Use appropriate foam to blanket release and suppress vapors. Approach release from upwind. Absorb in noncombustible material for proper disposal.|Absorb on paper. Evaporate on a glass or iron dish in hood. Burn the paper.|Ventilation. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT wash away into sewer. (Extra personal protection: self-contained breathing apparatus).

If mesityl oxide gets into the eyes, flush them immediately with large amounts of water for 15 minutes, lifting the lower and upper lids occasionally. Get medical attention as soon as possible. Contact lenses should not be worn when working with this chemical.|If mesityl oxide gets on the skin, wash it immediately with soap and water. If mesityl oxide penetrates the clothing, remove the clothing immediately and wash the skin with soap and water. Get medical attention promptly.|If a worker has been incapacitated, move the affected worker from the hazardous exposure. Put into effect the established emergency rescue procedures. Do not become a casualty. Understand the facility's emergency rescue procedures and know the locations of rescue equipment before the need arises.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|For more Preventive Measures (Complete) data for MESITYL OXIDE (13 total), please visit the HSDB record page.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ 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 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for MESITYL OXIDE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Vapor irritating to eyes, nose and throat.|May be harmful if absorbed through skin or inhaled. Irritating to skin, eyes, and respiratory system.

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 25 ppm (100 mg/cu m).|Vacated 1989 OSHA PEL TWA 15 ppm (60 mg/cu m); STEL 25 ppn (100 mg/cu m) is still enforced in some states.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 ppm (40 mg/cu m).

Personal protection: self-contained breathing apparatus. Ventilation. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Fireproof. Separated from strong oxidants and acids. Do NOT store or transport in containers made from plastic or copper. Cool. Keep in the dark. Store in an area without drain or sewer access.

A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.

The substance is irritating to the eyes, skin and respiratory tract. Exposure far above the OEL could cause unconsciousness. If swallowed the substance may cause vomiting and could result in aspiration pneumonitis.

The substance defats the skin, which may cause dryness or cracking. The substance may have effects on the liver, kidneys and lungs.

NO open flames, NO sparks and NO smoking. Above 25 °C use a closed system, ventilation and explosion-proof electrical equipment.

STRICT HYGIENE!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Mesityl oxide is produced, as an intermediate or a final product, by process units covered under this subpart.

| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

Exhaust from an automobile using various hydrocarbon fuels under simulated city conditions yielded concentrations of <0.1-1.5 ppm of mesityl oxide(1). Qualitatively detected in Lockport, IL oil refinery final effluent(2) and in advanced waste water treatment concentrates from Orange County and Lake Tahoe, CA(3-5). In a comprehensive survey of 46 industrial and publicly owned treatment works, mesityl oxide was qualitatively identified in effluents from various organic chemical manufacturing sites(6).

Toxicity

moderately toxic

Use of alcoholic beverages enhances the harmful effect.

LD50 Rat oral 655 mg/kg|LC50 Rat inhalation 1130 ppm/4 hr|LC50 Rat inhalation 9 g/cu m/4 hr|LD50 Mouse ip 354 mg/kg|For more Non-Human Toxicity Values (Complete) data for MESITYL OXIDE (12 total), please visit the HSDB record page.

Mesityl oxide was qualitatively identified in nectarines obtained from a local orchard in Winters, CA(1).

Mesityl oxide's production and use in manufacturing methyl isobutyl ketone(1), and its use as an intermediate(2), solvent for nitrocellulose(2) and vinyl chloride-vinyl acetate resins(2-3), additive(3), or mineral extractant(3) may result in its release to the environment through various waste streams(SRC). Mesityl oxide's use as an insect repellent(4) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a water solubility of 28,900 mg/L(2) and a regression-derived equation(3), indicates that mesityl oxide is expected to have very high mobility in soil(SRC). Volatilization of mesityl oxide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.67X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 8.21 mm Hg(4), and water solubility(2). Mesityl oxide is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Theoretical %BOD values of 74(5) and 30(6) from studies done with sewage inoculum suggest that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a water solubility of 28,900 mg/L(2) and a regression-derived equation(3), indicates that mesityl oxide 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 3.67X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 8.21 mm Hg(4), and its water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 17 hours and 11 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 1.9(SRC), using a water solubility of 28,900 mg/L(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Theoretical %BOD values of 74(7) and 30(8) from studies done with sewage inoculum suggest that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), mesityl oxide, which has a vapor pressure of 8.21 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase mesityl oxide 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 4.9 hours(SRC), calculated from its rate constant of 7.86X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The rate constant for the vapor-phase reaction of mesityl oxide with ozone has been estimated as 2X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 1.4 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). The rate constant for the vapor-phase reaction of mesityl oxide with nitrate has been estimated as 2.04X10-13 cu cm/molecule-sec at 25 °C(5). This corresponds to an atmospheric half-life of about 3.9 hours at an atmospheric concentration of 2.4X10+8 nitrate molecules per cu cm(6). Vapor-phase mesityl oxide undergoes direct photolysis with an experimental half-life and rate constant of 76.8 hrs and 8.75X10-3/hr, respectively(7).

The rate constant for the vapor-phase reaction of mesityl oxide with photochemically-produced hydroxyl radicals has been estimated as 7.86X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of mesityl oxide with ozone has been estimated as 2X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.4 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). The rate constant for the vapor-phase reaction of mesityl oxide with nitrate has been estimated as 2.04X10-13 cu cm/molecule-sec at 25 °C(3). This corresponds to an atmospheric half-life of about 3.9 hours at an atmospheric concentration of 2.4X10+8 nitrate molecules per cu cm(4). Mesityl oxide is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(5). Vapor-phase mesityl oxide undergoes direct photolysis with an experimental half-life and rate constant of 76.8 hrs and 8.75X10-3/hr, respectively(6).

An estimated BCF of 1.9 was calculated in fish for mesityl oxide(SRC), using a water solubility of 28,900 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of mesityl oxide is estimated as 15(SRC), using a water solubility of 28,900 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that mesityl oxide is expected to have very high mobility in soil.

The Henry's Law constant for mesityl oxide is estimated as 3.67X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 8.21 mm Hg(1), and water solubility, 28,900 mg/L(2). This Henry's Law constant indicates that mesityl oxide is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 17 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 11 days(SRC). Mesityl oxide's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of mesityl oxide from dry soil surfaces may exist(SRC) based upon its vapor pressure(1).

DRINKING WATER: Mesityl oxide was qualitatively detected in samples of drinking water taken from Cincinnati, OH waterworks on 10/17/78 and 1/14/80(1-3).|SURFACE WATER: Mesityl oxide was qualitatively detected in the Glatt River in Switzerland(1).

Mesityl oxide was qualitatively identified in Idaho Russet Burbank baked potatoes(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 362 workers (34 of these are female) are potentially exposed to mesityl oxide in the US(1). Occupational exposure to mesityl oxide may occur through inhalation and dermal contact with this compound at workplaces where mesityl oxide is produced or used(SRC). Monitoring data indicate that the general population may be exposed to mesityl oxide via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with insect repellents and other products containing mesityl oxide(SRC).

Name Type of Test Exposure Route Species Observed Dose/Duration Toxic Effects Reference
SKIN/EYE IRRITATION DATA Standard Draize test Administration into the eye Human 25 ppm/15M -- Journal of Industrial Hygiene and Toxicology. (Cambridge, MA) V.18-31, 1936-49. For publisher information, see AEHLAU. Volume(issue)/page/year: 28,262,1946
SKIN/EYE IRRITATION DATA TCLo - Lowest published toxic concentration Inhalation Human 25 ppm Sense Organs and Special Senses (Eye)--conjunctive irritation Journal of Industrial Hygiene and Toxicology. (Cambridge, MA) V.18-31, 1936-49. For publisher information, see AEHLAU. Volume(issue)/page/year: 28,262,1946
SKIN/EYE IRRITATION DATA LD50 - Lethal dose, 50 percent kill Oral Rodent - rat 1120 mg/kg Details of toxic effects not reported other than lethal dose value-- Documentation of the Threshold Limit Values and Biological Exposure Indices, 5th ed., Cincinnati, OH, American Conference of Governmental Industrial Hygienists, Inc., 1986 Volume(issue)/page/year: 6,896,1991

Drug Information

Mesityl oxide ... reduced in body to apprecialbe extent. ... Shown to increase glucuronic output in rabbits. ... Repeated exposure of animals to non-lethal concentrations, suggests that it is probably not rapidly eliminated, and that with frequent exposures, blood concentration reaches anesthetic level.|It is readily absorbed through the intact skin.|... /Mesityl oxide/ can be absorbed into the body by inhalation of its vapor, through the skin and by ingestion.

Some mesityl oxide remains unchanged, some reduction and conjugation occurs. Metabolite is believed to be a glucuronide, but has not been demonstrated. /From table/|... Mesityl oxide reacts with certain sulfur-containing compounds in body, probably sulfhydryls and that this forms odorous product which ... /is/ believed to be sulfur substituted ketone.

4-Methyl-4-penten-2-one is the precursor of methyl isobutyl ketone ... and can be produced from acetone in a single- or a two-step process. Pure mesityl oxide is obtained by azeotropic distillation of the crude water-containing product. Subsequent purification by removal of the accompanying impurities, such as mesitylene and phorone ... is effected by distillation.

Inhalation causes irritation of nose and throat, headache, dizziness, difficult breathing. Contact with liquid or concentrated vapor causes severe eye irritation. Liquid irritates skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately flush the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water. Get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)


Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Anticipate seizures and treat if necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. /Turpentine, terpenes, and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive- pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... Monitor cardiac rhythm and treat arrhythmias as necessary ... Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ...Treat seizures with diazepam or lorazepam ... Use proparacaine hydrochloride to assist eye irrigation ... /Turpentine, Terpenes, and related compounds/|Irrigate eyes with water. Wash contaminated areas of body with soap and water. Give oxygen if indicated.|/If ingested/ ... Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention.

/HUMAN EXPOSURE STUDIES/ A majority of individuals experienced eye irritation after 3 to 5 minutes of exposure at 25 ppm mesityl oxide with the addition of nasal irritation at 50 ppm. On the basis of an unpleasant taste that persisted in some cases for 3 to 6 hours after exposure and the nasal irritation experienced at 50 ppm, these workers suggested 25 ppm as the highest concentration, which would be satisfactory for an 8-hour day. The probable human response to 100 ppm of mesityl oxide was predicted to be eye and mucous membrane irritation accompanied by difficulty in breathing, headache, and vertigo.|/HUMAN EXPOSURE STUDIES/ Exposure to 50 to 100 ppm caused eye irritation and half of the test subjects experienced nasal irritation and pulmonary discomfort at 25 ppm.|/SIGNS AND SYMPTOMS/ Mesityl oxide (MO) can produce marked irritation and transient corneal injury to the eye. Occasional skin contact may produce some irritation; prolonged contact may produce dermatitis and, if the dose is high enough, systemic injury. MO ... can produce ... /CNS depression/ via inhalation exposure. Sublethal concentrations of the vapors may result in vascular congestion, which has been reported to occur primarily in the kidneys. The liver and lung are affected to a lesser degree. Death is generally attributed to its ... /CNS depressant/ action ... The penetrating odor and eye and nose irritation that occurs following exposure at low levels should prevent overexposure.|/SIGNS AND SYMPTOMS/ Mesityl oxide is a strong irritant both on contact with the liquid and in the vapor phase and can cause necrosis of the cornea. Short exposure /may cause CNS depression/ ...|For more Human Toxicity Excerpts (Complete) data for MESITYL OXIDE (11 total), please visit the HSDB record page.

mesityl oxide

The substance can be absorbed into the body by inhalation of its vapour and by ingestion.|inhalation, ingestion, skin and/or eye contact

irritation eyes, skin, mucous membrane; narcosis, coma; In Animals: liver, kidney damage; central nervous system effects


Cough. Sore throat. Shortness of breath. Headache. Dizziness. Drowsiness. Unconsciousness. Respiratory and cardiac arrest.


Dry skin. Redness. Pain.


Redness. Pain.

Eyes, skin, respiratory system, central nervous system, liver, kidneys

Mesityl oxide Use and Manufacturing

Methods of Manufacturing

Acetone is condensed into diacetone alcohol in the presence of sodium hydroxide. The diacetone alcohol is dehydrated in the presence of phosphoric acid, and the crude product at 126-131°C is collected by fractional distillation, followed by rectification, and the fraction at 128-132°C is collected to obtain the finished product. The 1t product consumes about 1200kg of diacetone alcohol.

Uses

Solvent for nitrocellulose, many gums and resins, particularly vinyl resins.In lacquers, varnishes and enamels.In making methyl isobutyl ketone.


Intermediates

Production

This chemical is listed as a High Production Volume (HPV) (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).|(1973) 1.23X10+10 GRAMS (ACETONE USED IN MFR)|(1975) 2.07X10+10 GRAMS|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2982]

Grade: Technical|Grades of purity: 97+%

Petrochemical manufacturing|3-Penten-2-one, 4-methyl-: ACTIVE|FLAVORS USEFUL IN PEPPERMINT AND SPEARMINT.

OPTIMUM CONDITIONS FOR ABSORPTION & GAS CHROMATOGRAPHIC DETERMINATION OF MESITYL OXIDE & DIACETONE ALC WERE DETERMINED. ISOPROPYL ALC WAS MOST SUITABLE FOR ABSORPTION OF THE 2 CMPD FROM AIR. GAS CHROMATOGRAPHIC DETERMINATIONS WERE DONE ON COLUMNS WITH CARBOWAX 20 M DEPOSITED ON CHROMOSORB W-AW-DMCS (80-100 MESH) WITH FLAME-IONIZATION DETECTION. THE LOWER LIMIT OF DETERMINATION WAS 7.2 MG/CU M OF AIR FOR MESITYL OXIDE.|NIOSH Method 1301. Analyte: Mesityl oxide. Matrix: Air. Procedure: Gas chromatography, flame ionization detector. For mesityl oxide this method has an estimated detection limit of 0.05 mg/sample. The precision/RSD is 0.014 and the recovery is not given. Applicability: The working range is 0.10 to 3.0 mg/sample. Interferences: None reported.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]|Fire Hazards -> Flammable - 3rd degree, Reactive - 1st degree

Flavoring Agents

Computed Properties

Molecular Weight:98.14
XLogP3:1.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:98.073164938
Monoisotopic Mass:98.073164938
Topological Polar Surface Area:17.1
Heavy Atom Count:7
Complexity:96.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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