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Cyclohexanone

Cyclohexanone structure

Cyclohexanone 

structure
  • CAS No:

    108-94-1

  • Formula:

    C6H10O

  • Chemical Name:

    Cyclohexanone

  • Synonyms:

    Cyclohexanone;Anone;Hexanon;Hytrol O;Nadone;Pimelic ketone;Pimelin ketone;Sextone;Anon;NSC 5711;C 0489

  • Categories:

    Cosmetic Ingredient  >  Dissolving Agent

Description

Cyclohexanone, also known as C6H10O, is a colorless to pale yellow liquid with distinctive properties, characterized by a minty or acetone-like odor that becomes slightly rubbery in pure form. In chemical structure, cyclohexanone is a cyclic ketone compound formed by replacing one carbon atom in a cyclohexane molecule with an oxygen group. This molecular structure gives it unique physical and chemical properties. The physical properties of cyclohexanone make it excel in various applications. Its density is less than water, with a low flash point (111°F), meaning it can evaporate at relatively lower temperatures. Its vapor density is greater than air, making it an effective medium in certain chemical reactions. Additionally, cyclohexanone is a highly volatile liquid that can be mixed with most organic solvents but has low solubility in water, which makes it widely applicable in the solvent industry. In industrial production, cyclohexanone is produced in billions of kilograms per year, mainly used as a precursor for nylon production. Nylon is a widely used synthetic polymer found in clothing, carpets, and engineering plastics, among other products. Additionally, cyclohexanone is often used as a medium for chemical reactions, participating in various organic synthesis reactions to produce various chemicals. Meanwhile, due to its good solubility, it is also used as a solvent for paint, coatings, and cleaning agents. Cyclohexanone has many uses, but it should be noted that it has certain biological activity towards the body and may exist as an exogenous metabolite in the body. Therefore, appropriate protective measures should be followed when handling and using cyclohexanone, avoiding inhalation, contact with skin and eyes, and improper emissions to protect the environment and workers' health. Cyclohexanone is a versatile organic compound with wide applications in the chemical industry, from nylon production to solvent applications, and is present everywhere. However, it should be used with caution to ensure safety and environmental protection. The CAS number of cyclohexanone is 108-94-1, and it has many other names, such as anonon, hexanone, and cetone, reflecting its applications and recognition in different fields.

Cyclohexanone Basic Attributes

98.14

98.14

203-631-1

5QOR3YM052

0425

5711

1915

DTXSID6020359

OILY LIQUID|WATER-WHITE TO PALE YELLOW LIQUID|Water-white to pale-yellow liquid ...

2914220000

Characteristics

17.07000

0.76

Cyclohexanone appears as a colorless to pale yellow liquid with a pleasant odor. Less dense than water . Flash point 111°F. Vapors heavier than air. Used to make nylon, as a chemical reaction medium, and as a solvent.

0.9478 g/cm3 @ Temp: 20 °C

-31 °C

1.4 °C @ Press: 1.0 Torr

116 °F

n 20/D 1.450(lit.)

150 g/L (10 ºC)Flammable. soluble in water.

Keep containers closed; prohibit open flame. Store in cool and dark plane.

3.4 mm Hg ( 20 °C)

3.4 (vs air)

LD50 orally in rats: 1.62 ml/kg (Smyth)

Class II Combustible Liquid: Fl.P. at or above 100°F and below 140°F.

vol% in air: 1.1.4 (at 100°C)

ODOR REMINISCENT OF PEPPERMINT & ACETONE

11.3None

6.39e-12 cm3/molecule*sec

9.00e-06 atm-m3/mole

11.3

Flammable. Soluble in water.

Ketones

Highly Flammable

CYCLOHEXANONE forms an explosive peroxide with H2O2, and reacts vigorously with oxidizing materials (nitric acid). (NTP, 1992)

Cyclohexanone|D*: Other compounds that may form peroxides|9 samples, >1yrs, 1-3 ppm|Management of time-sensitive chemicals (JCHAS)

788 °F (USCG, 1999)|420 °C; 788 °F|420 °C

-15,430 btu/lb= -8570 cal/g= -358.8x10+5 J/kg

9.14 eV

Lower flammable limit: 1.1% by volume at 212 °F; Upper flammable limit: 9.4% by volume|Class II Combustible Liquid: Fl.P. at or above 100°F and below 140°F.

The vapour is heavier than air. As a result of flow, agitation, etc., electrostatic charges can be generated.

Corrosive

45.06 kJ/mol @ 25 °C

Critical temp: 673 °F= 356 °C= 629 deg K; Critical pressure: 560 psia= 38 atm= 3.8 MN/sq m

Safety Information

III

3

UN1915 Cyclohexanone, Hazard Class: 3; Labels: 3-Flammable liquid.UN 1915 3/PG 3

1

R10;R20

25-36/37/39-26

GW1050000

Xn

Fireproof. Separated from strong oxidants.

Stable. Combustible. Incompatible with strong oxidizing agents.

P280-P305 + P351 + P338

H226-H302 + H312 + H332-H315-H318

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U057, F003, must conform with USEPA regulations in storage,transportation, treatment and disposal of waste.|Cyclohexanone is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.|A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °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 °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 °C and a residence time of 0.1 to 2 seconds.

Incompatible with oxidizing agents.|Under controlled conditions, the explosive dimeric and trimeric acetone peroxide were produced. 2-Butanone and 3-pentanone gave shock and heat sensitive oily peroxides. Cyclopentanone reacts vigorously, giving a solid which soon produces a series of explosions if left in contact with the undiluted reaction liquor. Cyclohexanone gave oily, rather explosive peroxides.|Oxidation of 4-methylcyclohexanone by addition of nitric acid at about 75 °C caused a detonation to occur. These conditions have been used previously to oxidize the corresponding alcohol, but although the ketone is apparently an intermediate in oxidation of the alcohol, the former requires a much higher temp to start and maintain the reaction.|Oxidizers, nitric acid.

Occupational exposure to ketones, including cyclohexanone, is discussed.[NIOSH; Criteria Document: Ketones p.1-244 (1978) DHEW Pub. NIOSH 78-173.]|44 FR 31866 (6/1/79). The fourth report of the TSCA interagency testing committee to the administrator, EPA concerning cyclohexanone is discussed.|Spencer PS et al; Crit Rev Toxicol 7 (4): 279-356 (1980). Neurotoxicity of cyclohexanone is discussed.

UN 1915

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: 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. (ERG, 2016)|Flammable. Above 44 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree

|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P312, P304+P340, P312, P370+P378, P403+P235, and P501|Danger|H226 (100%): 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, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P362, P363, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 4093 companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P311, P312, P314, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, 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+P310, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P311, P312, P314, P321, P322, P330, P331, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: 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 127 [Flammable Liquids (Water-Miscible)]: 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 or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. (NIOSH, 2016)|Where there is a danger of splashes or prolonged skin contact, eye and face protection and hand and arm protection should be worn. /Cycloparaffins/|Wear appropriate chemical protective gloves, boots and goggles.|Clothing which is contaminated with cyclohexanone should be removed immediately and placed in closed containers for storage until it can be discarded or until provision is made for the removal of cyclohexanone from the clothing. If the clothing is to be laundered or cleaned, the person performing the operation should be informed of cyclohexanone's hazardous properties.|Wear appropriate personal protective clothing to prevent skin contact.|For more Personal Protective Equipment (PPE) (Complete) data for CYCLOHEXANONE (9 total), please visit the HSDB record page.|(See protection codes)

MODERATE, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS ...|/CYCLOHEXANONE/ ... SHOULD NOT PRESENT A PROBLEM OF FLAMMABILITY UNLESS HANDLED AT ELEVATED TEMP.

SLIGHT, IN ITS VAPOR FORM, WHEN EXPOSED TO FLAME|Explosive limits , vol% in air: 1.1-9.4 (at 100 °C)

ALCOHOL FOAM, DRY CHEMICAL OR CARBON DIOXIDE|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.

Remove all ignition sources. Ventilate area of spill or leak. For small quantities of liquids containing cyclohexanone, absorb on paper towels and place in an appropriate container. Place towels in a safe place (such as a fume hood) for evaporation. Allow sufficient time for evaporation of the vapors so that the hood ductwork is free from cyclohexanone vapors. Burn the paper in a suitable location away from combustible materials.|Large quantities of liquids containing cyclohexanone may be absorbed in vermiculite, dry sand, earth, or a similar material and placed in an appropriate container. Cyclohexanone should not be allowed to enter a confined space such as a sewer because of the possibility of an explosion. Cyclohexanone may be collected by vacuuming with an appropriate system. If a vacuum system is used, there should be no sources of ignition in the vicinity of the spill and flashback prevention devices should be provided.|Absorb on paper. Evaporate on a glass or an iron dish in hood. Burn the paper.

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. Use water spray to knock-down vapors.|Personnel protection: Avoid breathing vapors. Keep upwind. Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear appropriate chemical protective gloves, boots, and goggles.|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.|The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.

/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 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 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.|For more DOT Emergency Guidelines (Complete) data for CYCLOHEXANONE (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.

Inhalation of vapor can cause irritation of mucous membranes. Contact of liquid may produce dermatitis in sensitive individuals.

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 50 ppm (200 mg/cu m).|Vacated 1989 OSHA PEL TWA 25 ppm (100 mg/cu m), skin designation, is still enforced in some states.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 25 ppm (100 mg/cu m). Skin.

Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Fireproof. Separated from strong oxidants.

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

The substance and the vapour are irritating to the eyes, skin and respiratory tract. Exposure far above the OEL could cause lowering of consciousness.

NO open flames, NO sparks and NO smoking. Above 44 °C use a closed system, ventilation and explosion-proof electrical equipment. Prevent build-up of electrostatic charges (e.g., by grounding).

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles 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). These standards implement Section 111 of the Clean Air Act and are based on the Administrator's determination that emissions from the Synthetic Organic Chemical Manufacturing Industry cause, or contribute significantly to, air pollution which may reasonably be anticipated to endanger public health or welfare. The intended effect of these standards is to require all newly constructed, modified, and reconstructed Synthetic Organic Chemical Manaufacturing Industry process units to use the best demonstrated system of continuous emission reduction for equipment leaks of Volatile Organic Compounds, considering costs, non air quality health and environmental impact and energy requirements. Cyclohexanone is produced, as an intermediate or final product, by process units covered under this subpart. These standards of performance become effective upon promulgation but apply to affected facilities for which construction or modification commenced after January 5, 1981.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

U057; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.|F003; A hazardous waste from nonspecific sources when a spent solvent.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2700 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U057; As stipulated in 40 CFR 261.33, when CYCLOHEXANONE, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).|When cyclohexanone is a spent solvent, it is classified as a hazardous waste from a nonspecific source (F003), as stated in 40 CFR 261.31, and must be managed according to State and/or Federal hazardous waste regulations.

In a comprehensive survey of wastewater from 4,000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, cyclohexanone was identified in discharges of the following industrial category (positive occurrences, median concentration in ppb): leather tanning (4; 593), iron and steel manufacturing (2; 13.3), nonferrous metals (1; 28.1), paint and ink (5; 34.4), printing and publishing (2; 149), ore mining (2; 3.1), inorganic chemicals (5; 32.7), plastics and synthetics (23; 75.8), auto and other laundries (1; 1.2), pharmaceuticals (2; 44.2), explosives (1; 16.8), aluminum (4; 12.9), electronics (4; 11.9), organic chemicals (2; 62.7), and POTWs (12; 23.5)(1). Maximum effluent concentrations above 1000 ppb were observed in leather tanning (1,927 ppb), inorganic chemicals (10,256 ppb), and plastics and synthetics (2,345 ppb)(1).|Wastewater from advanced treatment facilities in Lake Tahoe, CA, Dallas, TX, and Blue Plains, Washington, DC contained cyclohexanone(1). A final effluent grab sample from the Danville, IL POTW collected in June 1980 contained cyclohexanone(2). Wastewaters from processing shale oil have been found to contain cyclohexanone(3,4). It was identified in leachate from a municipal landfill in Ontario, Canada(5). The concentration of cyclohexanone in active compost blower exhaust from a wastewater sludge composting facility was 13 ug/cu m(6).

RURAL: Cyclohexanone was qualitatively identified in air samples from the Whitaker Forest in the Sierra Nevada Mountains, CA, a forest containing mixed conifers, in June 1990(1) and in the southern Black Forest in Germany in 1983(2).|SOURCE DOMINATED: Cyclohexanone was detected in 4 of 12 air samples collected near American Cyanamide in Linden, NJ (1976-8) at levels of 22-629 ng/cu m, 270 ng/cu m average(1). Maximum ground levels of 153 ug/cu m were detected on the boundary of the Holston Army Munitions Plant(2).|INDOOR AIR: Cyclohexanone was detected in one of six homes tested in Northern Italy at a concentration of 6 ug/cu m(1).

No cyclohexanone was detected (detection limit 50 ppm) in 26 samples of glue from 12 different manufacturers in Europe and the U.S. obtained in Denmark, especially from toy dealers(1).

Toxicity

Cyclohexanone may be released to the environment, primarily air and wastewater, as a result of its manufacture, use, transport, and disposal. Cyclohexanone is emitted to the atmosphere during its industrial production from venting of "spent air" and other vent streams(1). Over 96% of all cyclohexanone produced is oxidized to adipic acid (for the manufacture of nylon 66) or converted to caprolactam (for the manufacture of nylon 6)(2). Other industrial uses are: thinner or solvent for synthetic resins, polymers, lacquers, inks, paint, and spot remover; and synthesis of insecticides, herbicides, and pharmaceuticals(1,2).|Use of cyclohexanone as a solvent results in its evaporation into the air. Applications in which cyclohexanone is used as a solvent would be expected to release more chemical than those in which it is used as a chemical intermediate in closed systems. Cyclohexanone may be produced as a disinfection byproduct in drinking water(1). In a pilot plant study in Evansville, IN, it was identified in raw water treated with liquid or gaseous ClO2, Cl2, and FeCl2 with dual media filtration, but not in raw water or raw water treated with ClO2 alone. In a 1978-1982 German survey of industrial solvents commonly found in thinners, degreasers, paints, inks and some reagents, cyclohexanone was found in 1.1% of the 275 products analyzed(2).

TERRESTRIAL FATE: Cyclohexanone is estimated to be highly mobile in soil(1,3,SRC). In view of its moderate vapor pressure(2) and low adsorption to soil(3), it would be expected to volatilize from surface soil. Although data are lacking, it may also undergo direct photolysis on the soil surface(4). Cyclohexanone is readily biodegradable according to aerobic screening tests(5-12) and therefore would be expected to biodegrade in soil(SRC).|AQUATIC FATE: If released in water, cyclohexanone would be slowly lost by volatilization. Its estimated half-lives in a model river and model lake are 4.1 and 33 days, respectively(1,2). Cyclohexanone is readily biodegradable according to aerobic screening tests(6) and in a die-away test performed using microorganisms from river water(3) and therefore, may be expected to biodegrade in natural waters. Adsorption to sediment(2,4) and bioconcentration(2,5) in aquatic organisms should be minimal(2) based upon its high water solubility(4) and low octanol/water partition coefficient(5).|ATMOSPHERIC FATE: In the atmosphere, cyclohexanone will degrade by reacting with photochemically-produced hydroxyl radicals. Its estimated half-life resulting from this reaction is 1.3 days(1,2).

The rate constant for the vapor-phase reaction of cyclohexanone with photochemically-produced hydroxyl radicals has been estimated to be 12.6X10-12 cu cm/molecule-sec at 25 degC(1) which corresponds to an atmospheric half-life of 1.3 days, assuming a hydroxyl radical concentration of 5X10+5 radicals/cu cm. Cyclohexanone absorbs UV radiation up to an approximate cutoff point of 325 nm(2). The measured direct photolysis rate constant in air is approximately 0.16 days, which corresponds to a half-life of 4.3 days(2). Ketones are resistant to hydrolysis(3).

The bioconcentration factor (BCF) for cyclohexanone can be estimated to be 2.4 based on the log Kow of 0.81(1) and a recommended regression equation(2). This BCF indicates that cyclohexanone will not bioconcentrate in aquatic organisms(SRC).|Based on a water solubility of 23,000 mg/l at 20 °C(1) and a log Kow of 0.81(2), the log BCF for cyclohexanone has been estimated to be 0.14 and 0.39, respectively, from recommended regression equations(1,3,SRC).

The Koc for cyclohexanone estimated using structure activity relationships (SAR) is 15(1). A Koc of 17 can be estimated from the water solubility, 23,000 mg/L(2), using a recommended regression equation(3). According to a suggested classification scheme(4), these Koc values indicate that cyclohexanone will be highly mobile in soil.

The Henry's Law constant for cyclohexanone, 9.00X10-6 atm-cu m/mol at 25 degC(1), may be used to estimated the volatilization half-lives of cyclohexanone from a model river and lake. Its half-life in a 1 m deep model river with a 1 m/s current and 3 m/s wind is 4.1 days(2). Its half-life in a model lake 1 m deep with a 0.05 m/s current and a 0.5 m/s wind is 33 days. In view of cyclohexanone's moderate vapor pressure, 4.33 mm Hg at 25 degC(3), and low soil adsorptivity, it would be expected to volatilize from surface layers of soil(2).

DRINKING WATER: Cyclohexanone was qualitatively detected in drinking water from Miami, FL; Ottumwa, IA; Philadelphia, PA; and Cincinnati, OH(1). Ottumwa, IA tap water contained 0.1 ppb cyclohexanone(2). Positive identifications in drinking water from Cincinnati, OH (Jan 1980), Miami, FL (Feb 1976), New Orleans, LA (Jan 1976), Ottumwa, IA (Sept 1976), and Seattle, WA (Nov 1976)(3).|GROUND WATER: Maximum concn of 30 ppb detected in ground waters from the Netherlands(1). Qualitative detection in a ground water aquifer in Australia(2).|SURFACE WATER: Cyclohexanone was qualitatively detected in surface waters within the blast zone of Mount St. Helens, WA 2.5 and 3.5 months after the volcanic eruption in May 18, 1980(1). The low molecular weight organic materials found are believed to be derived from pyrolysis of plant and soil organic materials(1). Qualitative detection of cyclohexanone was reported in the Rhine River(2).

... INDUSTRIALLY, CONTACT WITH SKIN & EYE & INHALATION OF VAPORS ARE MOST LIKELY TO OCCUR.|Humans will be primarily exposed to cyclohexanone by inhalation or dermal contact in occupational settings. The general population may be exposed through consumption of contaminated drinking water or inhalation of contaminated air. (SRC)|NIOSH (NOES Survey 1981-1983) has statistically estimated that 373,986 workers are potentially exposed to cyclohexanone in the USA(1). Of these exposures, 95% are from trade name mixtures that contain cyclohexanone. Environmental levels of cyclohexanone in a large video tape manufacturing plant and two plastic bag printing factories in Singapore ranged from 0.1 to 36.0 ppm, with a mean of 9.04 ppm(2). In a 1983 Belgium study, 262 air samples from 78 plants in northern Belgium were analyzed(3). Of these, 22 samples contained cyclohexanone, 9 from printing establishments and 13 from other plants; no cyclohexanone was found in painting or car repair shops. In a study of 15 screen printing plants in The Netherlands, the median and maximum TWA levels of cyclohexanone in the workrooms ranged from 0.02 to 10.60 mg/cu m and from 0.13 to 23.58 mg/cu m, respectively(4).

In a study including 42 production workers from a large video tape manufacturing plant and 17 workers from two plastic bag printing plants in Singapore, the mean cyclohexanone level in breath was 1.08 ppm with a range of 0-6.4 ppm(1). Environmental levels of cyclohexanone in the plants ranged from 0.1 to 36.0 ppm, with a mean of 9.04 ppm.

Drug Information

... ABSORPTION OF CYCLOHEXANONE THROUGH SKIN PRODUCES SAME EFFECTS AS BY OTHER ROUTES BUT DOSAGE REQUIRED IS LARGER.

/AFTER/ IP INJECTION OF 0.5 ML/MOUSE ... ONE OF METABOLIC PRODUCTS ... FOUND WAS ADIPIC ACID, PRESUMABLY DUE TO OXIDN OF CYCLOHEXANONE.|IT IS METABOLIZED BY REDUCTION INTO CYCLOHEXANOL & IS EXCRETED AS CYCLOHEXYLGLUCURONIDE.|... MINOR (1-2%) METABOLITES OF ... CYCLOHEXANONE & CYCLOHEPTANONE HAVE BEEN DETECTED IN RAT & RABBIT URINE. 2-HYDROXYCYCLOALKYLMERCAPTURIC ACIDS WHICH WERE PRESENT AS ... SULFATES ("DOUBLE CONJUGATES") ARE PRESUMABLY FORMED FROM DEHYDRATION OF CYCLOALKANOLS (MAJOR METABOLITES) TO CYCLOALKENES WITH SUBSEQUENT EPOXIDATION & MERCAPTURATION.|HEPATIC NICOTINAMIDE ADENINE DINUCLEOTIDE-DEPENDENT ALCOHOL DEHYDROGENASE ... HAS BEEN SHOWN TO BE RESPONSIBLE FOR METABOLISM OF ... CYCLOHEXANOL TO CORRESPONDING ... KETONE. SAME ENZYME IS CAPABLE OF CATALYZING REVERSE REACTION IN WHICH ... CYCLOHEXANONE ... /IS/ REDUCED TO ALCOHOL. EQUILIBRIUM OF SYSTEM FAVORS ... REVERSE REACTION & ... REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE ... /MAY/ FUNCTION AS COENZYME.|For more Metabolism/Metabolites (Complete) data for CYCLOHEXANONE (6 total), please visit the HSDB record page.

Inhalation of vapors from hot material can cause narcosis. The liquid may cause dermatitis. (USCG, 1999)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)|(See procedures)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .


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

IT HAS LOW ACUTE ORAL TOXICITY. OCCASIONAL SKIN CONTACT WITH LIQUID ... SHOULD CAUSE NO IRRITATION. ... BECAUSE IT IS CAPABLE OF DEFATTING SKIN, PROLONGED OR FREQUENTLY REPEATED SKIN CONTACT MAY ... /CAUSE/ IRRITATION OR DERMATITIS. EYE CONTACT WITH LIQUID MAY RESULT IN ... IRRITATION & ... TRANSIENT CORNEAL INJURY.|/CYCLOHEXANONE IS/ A WEAK CENTRAL NERVOUS DEPRESSANT ...|Exposure at 25 ppm of cyclohexanone was not uncomfortable for most subjects; 50 ppm was irritating especially to the throat; exposure at 75 ppm for 3 to 5 minutes resulted in more pronounced irritation of the eyes, nose, and throat.|... Achromatic regions, breaks, & deletions were seen in karyograms of human leukocytes which had been cultured on media containing 1x10-2, 1x10-3, 1x10-4 M cyclohexanone.|For more Human Toxicity Excerpts (Complete) data for CYCLOHEXANONE (9 total), please visit the HSDB record page.

cyclohexanone

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

irritation eyes, skin, mucous membrane; headache; narcosis, coma; dermatitis; In Animals: liver, kidney damage


Cough. Sore throat. Dizziness. Drowsiness.


MAY BE ABSORBED! Dry skin. Redness.


Redness. Pain.

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

Cyclohexanone Use and Manufacturing

Methods of Manufacturing

CATALYTIC OXIDATION OF CYCLOHEXANE|OBTAINED FROM CYCLOHEXANOL BY CATALYTIC DEHYDROGENATION OR BY OXIDN (WHICH YIELDS CYCLOHEXANONE & ADIPIC ACID) ... BRITISH PATENT 310,055 (SCHERING-KAHLBAUM 1928); US PATENTS 2,223,493-4 (DU PONT 1940); 2,285,914 (DU PONT 1942).|CATALYTIC HYDROGENTION OF PHENOL OR BY THE CATALYTIC AIR-OXIDATION OF CYCLOHEXANE; MAY BE PREPARED BY EITHER THE CATAYLTIC DEHYDROGENATION OR OXIDATIVE DEHYDROGENATION OF CYCHEXANOL. THE PROCESS IS CARRIED OUT IN EITHER A LIQUID PHASE CATALYZED BY PALLADIUM OR CARBON, OR IN THE VAPOR PHASE CATALYZED BY PALLADIUM OR ALUMINA.

Uses

Cyclohexanone is used in the productionof adipic acid for making nylon; in thepreparation of cyclohexanone resins; and asa solvent for nitrocellulose, cellulose acetate,resins, fats, waxes, shellac, rubber, and DDT..It is the raw material for the production of caprolactam and adipic acid; used as the solvents and diluent agents of paints, inks, synthetic resins and synthetic rubber; also used as leather degreasing agent.
Used as organic solvent;
Raw materials and solvents of synthet

Production

1,000,000,000 - 5,000,000,000 lb|(1972) 3.56X10+11 G|(1975) 2.51X10+11 G|(1984) 3.61X10+11 g|(1992) 6.65x10+5 t (estimated)|(1992) 4.78X10+8 kg

95% FOR CAPROLACTAM AND ADIPIC ACID; 5% FOR SOLVENT APPLICATIONS (1973)|97% FOR NYLON 6 OR NYLON 66 MFR (1979)

Technical: 99.8%|COMMERCIAL: 89%; HIGH PURITY: 99.5%

Adhesive manufacturing|Cyclohexanone: ACTIVE|Cyclohexanone, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|IN LACQUER INDUST AS SLOWLY EVAPORATING IMPROVER, ALSO FOR LACQUERS & INSULATORS FOR HEAT & ELECTRICITY & FOR AUTOMOBILE LACQUERS. IN TEXTILE & PLASTIC INDUST, AS SPOTTING AGENT & RE-LUSTERING AGENT FOR CELLULOSE ACETATE SILK & IN SPRAY PAINTING OF FABRIC & PLASTIC TEXTILES. USED IN THE LEATHER INDUSTRY; AS A METAL DEGREASER; IN PAINT REMOVERS & IN PRINTING INKS.|DISTILLATION OF PIMELIC ACID SALTS WILL ALSO YIELD CYCLOHEXANONE.

AIR SAMPLE, SPECTROPHOTOMETRY @ 525 NM. TREON JF ET AL; J IND HYG TOXICOL 25: 199 & 323 (1943). AIR SAMPLE, GAS CHROMATOGRAPHY. CROPPER FR, KAMINSKY S; ANAL CHEM 35: 735 (1963).|CYCLOHEXANONE WAS ABSORBED FROM AIR IN DISTILLED WATER & CONDENSED WITH FURFURAL IN ALKALINE MEDIUM, PRODUCT WAS ACIDIFIED WITH SULFURIC ACID & ANALYZED COLORIMETRICALLY AT 550 NM.|Matrix: air. Procedure: adsorption on charcoal, desorption with carbon disulfide, GC. Range: 98-392 mg/cu m. Sensitivity: 0.062.|ASTM Method No. D3686. Standard Practice for Sampling Atmospheres to Collect Organic Compound Vapors (Activated Charcoal Tube Adsorption Method). Toxic gas vapor detector tube (TGVTUB) detection limit not stated.|For more Analytic Laboratory Methods (Complete) data for CYCLOHEXANONE (7 total), please visit the HSDB record page.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fire Hazards -> Flammable - 2nd degree

Flavoring Agents

Computed Properties

Molecular Weight:98.14
XLogP3:0.8
Hydrogen Bond Acceptor Count:1
Exact Mass:98.073164938
Monoisotopic Mass:98.073164938
Topological Polar Surface Area:17.1
Heavy Atom Count:7
Complexity:68.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

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  • Data: 2026-07-23
  • Price: 9000.00Yuan/mt
  • Change: 0

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