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Cyclopentanone

Cyclopentanone structure

Cyclopentanone 

structure
  • CAS No:

    120-92-3

  • Formula:

    C5H8O

  • Chemical Name:

    Cyclopentanone

  • Synonyms:

    Cyclopentanone;Adipic ketone;Dumasin;Ketocyclopentane;Ketopentamethylene;Adipin keton;NSC 4122;6: PN: WO2007101224 PAGE: 36 claimed sequence;1800084-96-1

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

It is colorless, oily liquid with a pleasant mint smell. It has a melting point of-58.2 ℃, boiling point of 130.6 ℃, the relative density of 0.9509 (20 ℃), the refractive index of 1.4366 and the flash point of 29.82 ℃. It is miscible with ethanol, ethyl ether and slightly soluble in water. It is easy to undergo polymerization, especially in the case of trace amount of acid. colourless liquid Cyclopentanone has an agreeable, peppermint-like odor. It tends to polymerize in the presence of acid


Cyclopentanone appears as a clear colorless liquid with a petroleum-like odor. Flash point 87°F. Less dense than water and insoluble in water. Vapors heavier than air.|Liquid|CLEAR COLOURLESS LIQUID.|liquid; agreeable odour somewhat like peppermint


Cyclopentanone appears as a clear colorless liquid with a petroleum-like odor. Flash point 87°F. Less dense than water and insoluble in water. Vapors heavier than air.|Cyclopentanone is a cyclic ketone that consists of cyclopentane bearing a single oxo substituent. It has a role as a Maillard reaction product.

Cyclopentanone Basic Attributes

84.118

84.12

204-435-9

220W81TN3S

0427

4122

2245

DTXSID3029154

WATER-WHITE, MOBILE LIQUID

2914 29 00

Characteristics

17.1

0.38

Cyclopentanone appears as a clear colorless liquid with a petroleum-like odor. Flash point 87°F. Less dense than water and insoluble in water. Vapors heavier than air.

0.94869 g/cm3 @ Temp: 20 °C

-51.3 °C

130.6 °C @ Press: 760 Torr

26°C

n 20/D 1.437(lit.)

H2O: 9.18g/l slightly soluble

Flammables area

11.5 hPa (20 °C)

Relative vapour density (air = 1): 2.3

Intraperitoneal-mouse LD50: 1950 mg/kg; subcutaneous-Mouse LD50: 2600 mg/kg.

It is flammable in case of fire, high temperature and with burning producing irritated smoke.

1.6-10.8%(V)

DISTINCTIVE ETHEREAL ODOR, SOMEWHAT LIKE PEPPERMINT

2.94e-12 cm3/molecule*sec

1.00e-05 atm-m3/mole

POLYMERIZES EASILY, ESP IN PRESENCE OF ACIDS

Highly flammable. Insoluble in water.

Ketones

Highly Flammable

CYCLOPENTANONE polymerizes easily, especially in the presence of acids. Can react with oxidizing materials, i.e. hydrogen peroxide. (NTP, 1992)

Cyclopentanone|D*: Other compounds that may form peroxides|4 samples had 1-4 ppm peroxide; age >1 yrs|Management of time-sensitive chemicals (JCHAS)

The vapour is heavier than air.

Safety Information

III

3

UN 2245 3/PG 3

1

R10;R36/38

23

GY4725000

Xi

Treasury: ventilation, low-temperature and dry; store it separately from oxidants and acids.

Stable. Incompatible with strong reducing agents, strong oxidizing agents, strong bases.

P305 + P351 + P338

H226-H315-H319

The following wastewater treatment technologies have been investigated for cyclopentanone: concentration process: Biological treatment

OPDYKE DL J; FOOD COSMET TOXICOL 17 (3): 271 (1979). REVIEW WITH 23 REFERENCES ON TOXICITY, INHALATION, IRRITATION, SENSITIZATION, METABOLISM, PHARMACOLOGY & CYTOTOXICITY OF CYCLOPENTANONE.|Savolainer H; Nordic Expert Group for Documentation of Occupational Exposure Limits. Arbetarskyddtyrelsen Publikationsservice, 171 84 Solna, Sweden 33 pp. (1985). Literature survey on cyclohexanone and cyclopentanone as background for discussion of occupational exposure limits.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: 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. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016)|Flammable. Heating will cause rise in pressure with risk of bursting. Gas/air mixtures are explosive.|Flammable - 3rd degree

|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P313, P337+P313, P362, P370+P378, P403+P235, and P501|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|Aggregated GHS information provided by 619 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P312, P303+P361+P353, P305+P351+P338, P330, P337+P313, P370+P378, P403+P235, and P501

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: 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 128 [Flammable Liquids (Water-Immiscible)]: 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)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

DANGEROUS WHEN EXPOSED TO FLAME; CAN REACT WITH OXIDIZING MATERIALS.

ALCOHOL FOAM, CARBON DIOXIDE, DRY CHEM.

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ 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. Substances may be transported hot.|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ 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 or dilution water may cause pollution.|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ 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 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ 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 CYCLOPENTANONE (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.

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 acids. Cool. Keep in the dark. Keep in a well-ventilated room. Store only if stabilized.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes, skin and possibly the respiratory tract.

NO open flames, NO sparks and NO smoking.

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety goggles.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual 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.| 0 - Materials that in themselves are normally stable, even under fire conditions.

The major hazards encountered in the use and handling of cyclopentanone stem from its toxicologic properties and flammability. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this peppermint-smelling, water-white liquid may occur from its production and use as an intermediate for pharmaceuticals, biologicals, insecticides, and rubber chemicals. Effects from exposure may include contact burns to the skin and eyes, CNS depression, and suffocation. In activities and situations where over-exposure may occur, wear protective clothing and a positive pressure self-contained breathing apparatus. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes and wash exposed skin thoroughly with soap and water. Contaminated clothing and shoes should be removed and isolated at the site. Cyclopentanone may be ignited by heat, sparks, or flames (flash point: 87 °F, closed cup), and is dangerously reactive with oxidizing materials. Its heavier-than-air vapor may travel to a source of ignition and flash back, or accumulate to explosive concentrations in confined spaces such as sewers. Also, containers of this substance may explode in the heat of a fire. For fires involving cyclopentanone, extinguish with dry chemical, CO2, water spray, fog, or alcohol-resistant foam. Isolate the area for 1/2 mile in all directions if a tank, rail car, or tank truck is involved in the fire. For small spills of cyclopentanone, take up with sand or other noncombustible absorbent and place into containers for later disposal. Large spills should first be diked far ahead of the spill.

Cyclopentanone was detected in 4 of 7 wastewater effluents from energy related processes(1). A groundwater water sample from a coal gasification facility in Hanna, WY contained cyclopentanone at an average concn of 32 ppb; the process water at a coal gasification facility in Gillette, WY contained cyclopentanone at an average concn of 110 ppb; effluent from the gasification of Rosebud coal in Morgantown, WV contained cyclopentanone at an average concn of 56 ppb; and retort water from an in situ shale oil processing facility in Rock Spring, WY contained cyclopentanone at an average concn of 5 ppb(1). Wastewater from coal gasification at the Grand Fork's Energy Technology Center, ND was also reported to contain cyclopentanone at a concn of 0.8 mg/L(2). In addition, wastewater effluent from a shale oil facility in Queensland, Australia was shown to contain cyclopentanone at a concn of 53 mg/L(3).

SOURCE DOMINATED: In Nov. 1982, cyclopentanone was detected in the air outside an oil shale wastewater facility of Occidental Oil Shale Inc. at Logan Wash, CO(1).

Toxicity

poisoning

Cyclopentanone may be released to the environment via effluents at sites where it is produced or used as an intermediate for pharmaceuticals, biologicals, insecticides and rubber chemicals(4). Cyclopentanone is also released to the environment via effluents from the manufacture and use of coal-derived liquid fuels and the disposal of coal liquefaction and gasification waste byproducts(1-3).

TERRESTRIAL FATE: Cyclopentanone is not expected to hydrolyse in soils(1), or undergo photolysis on sunlit soil surfaces due to lack of >290 nm UV adsorption(2). A single 5-day BOD screening test, which utilized activated sludge for inocula, suggests that cyclopentanone will biodegrade rapidly upon acclimation in terrestrial environments(3). An estimated Koc of 30(1) indicates cyclopentanone should have a very high mobility in soil(4). A Henry's Law constant of 1.0X10-5 atm-cu m/mole(5) suggests volatilization of cyclopentanone from moist soils may be an important fate process(1). Based on a vapor pressure of 11.4 mm Hg at 25 °C(6), cyclopentanone should evaporate from dry surfaces, especially when present in high concn such as in spill situations(SRC).|AQUATIC FATE: Cyclopentanone is not expected to hydrolyze(1) or undergo direct photolysis in aquatic systems(2). A single 5-day BOD screening test, which utilized activated sludge for inocula, suggests that cyclopentanone will biodegrade rapidly upon acclimation in natural waters(3). An estimated log bioconcentration factor (log BCF) of -0.05(1) indicates cyclopentanone should not bioconcentrate in aquatic organisms(SRC). An estimated Koc of 30(1) indicates cyclopentanone should not partition from the water column to organic matter contained in sediments and suspended solids(SRC). A Henry's Law constant of 1.0X10-5 atm-cu m/mole at 25 °C(4) indicates that volatilization of cyclopentanone from natural bodies of water should be an important fate process(1). Based on this Henry's Law constant, the volatilization half-life from a model river has been estimated to be 3.5 days(1,SRC). The volatilization half-life from an model pond, which considers the effect of adsorption, has been estimated to be about 40 days(5,SRC).|ATMOSPHERIC FATE: Based on a vapor pressure of 11.4 mm Hg at 25 °C(1), cyclopentanone is expected to exist almost entirely in the vapor phase in ambient air(2). Vapor phase reactions with photochemically produced hydroxyl radicals in the atmosphere have been shown to be important(SRC). A rate constant for cyclopentanone of 2.94X10-12 cu cm/molecule-sec at 25 °C corresponds to an atmospheric half-life of about 5.5 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(3). Direct photolysis in air is not expected to be an important environmental fate process(4).

Ketones are generally resistant to hydrolysis(2). The photolysis of cyclopentanone in the environment should not be an important fate process(2). The rate constant for the vapor-phase reaction of cyclopentanone with photochemically produced hydroxyl radicals has been measured to be 2.94X10-12 cu cm/molecule-sec at 25 °C, which corresponds to an atmospheric half-life of about 5.5 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(3).

Based upon an estimated log kow of 0.24(1), the bioconcentration factor (log BCF) for cyclopentanone has been calculated to be -0.05, from a recommended regression-derived equations(2). This BCF value indicates cyclopentanone should not bioconcentrate in aquatic organisms(SRC).

Based on an estimated water solubility of 9175 mg/L(1), a Koc value of 30 for cyclopentanone has been calculated from a regression-derived equation(1,SRC). This Koc value indicates cyclopentanone should be very highly mobile in soil(2).

A Henry's Law constant of 1.0X10-5 atm-cu m/mole at 25 °C(1) indicates that volatilization of cyclopentanone from natural bodies of water should be an important fate process(2). Based upon this Henry's Law constant, the volatilization half-life from a model river (1 meter deep flowing 1 m/sec with a wind speed of 3 m/sec) has been estimated to be 3.5 days(2,SRC). The volatilization half-life from a model pond, which considers the effect of adsorption, has been estimated to be about 40 days(3,SRC). Based on the vapor pressure of 11.4 mm Hg at 25 °C(4), cyclopentanone should evaporate from dry surfaces, especially when present in high concn such as in spill situations(SRC).

DRINKING WATER: Cyclopentanone was listed as a contaminant found in drinking water for a survey of US cities including Pomona, Escondido, Lake Tahoe and Orange Co, CA and Dallas, Washington, DC, Cincinnati, Philadelphia, Miami, New Orleans, Ottumwa, IA, and Seattle(1).|GROUNDWATER: Cyclopentanone was detected in 3 of 3 groundwater samples near a coal gasification site near Hoe Creek in northeastern WY at concn of 13, 37 and 180 ppb(1).

Cyclopentanone was identified as a volatile component of baked potatoes produced by the baking process(1).

The most probable route of human exposure to cyclopentanone is by inhalation, dermal contact and ingestion. Atmospheric workplace exposures have been documented(2). Drinking water supplies(3) and baked potatoes(1) have been shown to contain cyclopentanone.|The most probable human exposure to cyclopentanone would be occupational exposure, which may occur through dermal contact or inhalation at places where it is produced or used(SRC). A 1982 study showed cyclopentanone was emitted to the air from wastewaters at a shale oil facility exposing inside workers(1). Non-occupational exposures are likely to occur among populations with contaminated drinking water supplies(2); or from the ingestion of certain foods(3).

Drug Information

... MINOR (1-2%) METABOLITES OF CYCLOPENTANONE ... HAVE BEEN DETECTED IN RAT & RABBIT URINE. 2-HYDROXYCYCLOALKYLMERCAPTURIC ACIDS ... WHICH WERE PRESENT AS ... SULFATE ('DOUBLE CONJUGATE') ... PRESUMABLY FORMED BY DEHYDRATION OF CYCLOALKANOLS (MAJOR METABOLITES) TO CYCLOALKENES WITH SUBSEQUENT EPOXIDATION & MERCAPTURATION.|... RABBITS FED ... /CYCLOPENTANONE/ EXCRETED LARGE AMT (MORE THAN HALF THE DOSE) AS CYCLOPENTYL ... GLUCURONIDE ... MINOR AMT OF SULFATE CONJUGATES WERE ALSO PRESENT.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: 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 or dilution water may cause pollution. (ERG, 2016)

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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. 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. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest. Refer for medical attention.


Rinse and then wash skin with water and soap.


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

/PRODUCES CNS DEPRESSION/ IN HIGH CONCN.|25 MMOLAR CYCLOPENTANONE INCUBATED WITH /HUMAN LUNG FIBROBLAST/ CELLS FOR 30 MIN AT 37 °C SHOWED NO SIGNS OF ACTIVE MEMBRANE DAMAGE.

cyclopentanone

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

Cough. Sore throat.


Redness. Pain.


Redness. Pain.

Cyclopentanone Use and Manufacturing

Methods of Manufacturing

PREPD BY HEATING ADIPIC ACID TO 285-295 °C IN PRESENCE OF BARIUM HYDROXIDE, DISTILLING, EXTRACTING WITH ETHER & FRACTIONATING.

Uses

1, Take the n-valeraldehyde and cyclopentanone as raw material, and first go through aldol condensation reaction and further dehydration reaction to obtain pentylene cyclopentanone, then followed by selective catalytic hydrogenation to obtain pentyl cyclopentanone. Pentyl cyclopentanone has strong floral and fruity aroma as well as nuances of jasmine. It can be used in the formulation of daily chemical flavor with the usage amount being less than 20%. IFRA has no restrictions.
2, Take n


Intermediates

Production

10,000,000 - 50,000,000 lb

99+% PURITY GRADE /AVAILABLE FROM COASTAL SPECIALTY CHEMICALS/

All other basic inorganic chemical manufacturing|Cyclopentanone: ACTIVE

CYCLIC AMINES, KETONES (INCL CYCLOPENTANONE) & ALCOHOLS WERE EXTRACTED FROM URINE WITH DICHLOROMETHANE, SEPARATED BY GAS CHROMATOGRAPHY & QUANTITATIVELY DETERMINED FROM STD CURVES BASED ON PEAK HEIGHTS RELATIVE TO ALKANES USED AS INTERNAL STD.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fire Hazards -> Flammable - 3rd degree

Flavoring Agents

Computed Properties

Molecular Weight:84.12
XLogP3:0.4
Hydrogen Bond Acceptor Count:1
Exact Mass:84.057514874
Monoisotopic Mass:84.057514874
Topological Polar Surface Area:17.1
Heavy Atom Count:6
Complexity:58.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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