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Cyclohexene

Cyclohexene structure

Cyclohexene 

structure
  • CAS No:

    110-83-8

  • Formula:

    C6H10

  • Chemical Name:

    Cyclohexene

  • Synonyms:

    Cyclohexene;Benzene,tetrahydro-;Benzene tetrahydride;Tetrahydrobenzene;1,2,3,4-Tetrahydrobenzene;Cyclohex-1-ene;NSC 24835;33004-06-7

  • Categories:

    Active Pharmaceutical Ingredients  >  Other Chemical Drugs

Description

Colorless liquid with a sweet odor.


Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light and air because it forms peroxides.


Cyclohexene appears as a colorless liquid. Insoluble in water and less dense than water. Flash point 20°F. Vapors heavier than air. Inhalation of high concentrations may have a narcotic effect. Used to make other chemicals.|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|Colorless liquid with a sweet odor.


Cyclohexene appears as a colorless liquid. Insoluble in water and less dense than water. Flash point 20°F. Vapors heavier than air. Inhalation of high concentrations may have a narcotic effect. Used to make other chemicals.|Cyclohexene is a cycloalkene that is cylohexane with a single double bond.

Cyclohexene Basic Attributes

82.1436

82.14

203-807-8

12L0P8F7GN

1054

24835

2256

DTXSID9038717

Colorless liquid

2902199090

Characteristics

0

2.89

Cyclohexene appears as a colorless liquid. Insoluble in water and less dense than water. Flash point 20°F. Vapors heavier than air. Inhalation of high concentrations may have a narcotic effect. Used to make other chemicals.

0.8098 g/cm3 @ Temp: 20 °C

-103.5 °C

83 °C @ Press: 760 Torr

< -7°C

1.459

H2O: insoluble

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

67 mm of Hg (@ 20°C)

2.8 (vs air)

Class IB Flammable Liquid: Fl.P. below 73°F and BP at or above 100°F.

1.20-5%

Sweet odor

6.77e-11 cm3/molecule*sec

0.05 atm-m3/mole|Henry's Law constant = 4.55X10-2 atm-cu m/mole at 25 °C

Aniline equivalent: 10; wt/gal: 6.7 lb at 25 °C|Standard heat of fusion -38.5 kJ/mole /Liquid/|Hydroxyl radical reaction rate constant = 6.77X10-11 cu cm/molec-sec at 25 °C

Highly flammable. Insoluble in water.

Hydrocarbons, Aliphatic Unsaturated

Highly Flammable

CYCLOHEXENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154].

Cyclohexene|B: Compounds that form peroxides on concentration (distillation/evaporation)|5 samples had 0-50 ppm peroxide; age >1 - 30 yrs|Kelly|Oxidizes readily in air to form explosive levels of peroxides. See Bretherick's and Cameo.|http://www.inchem.org/documents/icsc/icsc/eics1054.htm

471 °F (244 °C)|244 °C

3751.7 kJ/mole at 25 °C /liquid/

8.95 eV

Lower flammable limit: 0.8% by volume; Upper flammable limit: 2.8% by volume|Class IB Flammable Liquid: Fl.P. below 73°F and BP at or above 100°F.

The vapour is heavier than air and may travel along the ground; distant ignition possible. As a result of flow, agitation, etc., electrostatic charges can be generated.

30.46 kJ/mole at boiling point; 33.47 kJ/mole at 25 °C

Critical temperature = 287.4 °C; Critical pressure = 4.347 MPa

Safety Information

II

3

UN 2256 3/PG 2

1

R11;R21/22;R65

S16-S29-S33-S36/37

GW2500000

F:Flammable;Xn:Harmful;

Fireproof. Separated from strong oxidants. Cool. Well closed. Store only if stabilized.

Stable in the absence of air - may form peroxides in storage. Incompatible with oxidizing agents. Highly flammable.

P210-P280-P301 + P310-P312-P331

H225-H302-H304-H311

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.

Strong oxidizers [Note: Forms explosive peroxides with oxygen upon storage.]

UN 2256

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: 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)|Highly flammable. Vapour/air mixtures are explosive.|Flammable - 3rd degree

|Danger|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P270, P273, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P312, P322, P330, P331, P361, P363, P370+P378, P391, P403+P235, P405, and P501|Aggregated GHS information provided by 95 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P310, P301+P312, P303+P361+P353, P304+P340, P305+P351+P338, P312, P330, P331, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P322, P330, P331, P332+P313, P337+P313, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / 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 130 [Flammable Liquids (Water-Immiscible / 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. (NIOSH, 2016)|Respirator Recommendation: Up to 2000 ppm: (Assigned Protection Factor = 25) Any supplied-air respirator operated in a continuous-flow mode. Substance causes eye irritation or damage; eye protection needed./(Assigned Protection Factor = 25) Any powered, air-purifying respirator with organic vapor cartridge(s). Substance causes eye irritation or damage; eye protection needed./(Assigned Protection Factor = 50) Any chemical cartridge respirator with a full facepiece and organic vapor cartridge(s)./(Assigned Protection Factor = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister./(Assigned Protection Factor = 50) Any self-contained breathing apparatus with a full facepiece./(Assigned Protection Factor = 50) Any supplied-air respirator with a full facepiece.|Respirator Recommendation: Emergency or planned entry into unknown concentrations or IDLH conditions: (Assigned Protection Factor = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode./(Assigned Protection Factor = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.|Respirator Recommendation: Escape: (Assigned Protection Factor = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister/Any appropriate escape-type, self-contained breathing apparatus.|Wear appropriate personal protective clothing to prevent skin contact.|For more Personal Protective Equipment (PPE) (Complete) data for CYCLOHEXENE (6 total), please visit the HSDB record page.|(See protection codes)

Highly flammable.|Dangerous; keep away from heat and open flame.

Vapour/air mixtures are explosive ... /Cyclohexene/ can form explosive peroxides.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.|Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-half (1/2) mile radius.

The vapour is heavier than air and may travel along the ground; distant ignition possible. As a result of flow, agitation, etc, electrostatic charges can be generated.|A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.

Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT wash away into sewer. Filter respirator for organic gases and vapours.

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 should be immediately removed due to its flammability hazard (ie, liquids with a flash point <100 °F).|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.|For more Preventive Measures (Complete) data for CYCLOHEXENE (10 total), please visit the HSDB record page.

/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/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 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/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 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/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 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/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 CYCLOHEXENE (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.

The substance irritates the eyes, the skin and the respiratory tract.

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 300 ppm (1015 mg/cu m).

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 300 ppm (1015 mg/cu m).

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. 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. Do NOT wash away into sewer.

Fireproof. Separated from strong oxidants. Cool. Well closed. Store only if stabilized.

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

The substance is irritating to the eyes, skin and respiratory tract. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. The substance may cause effects on the central nervous system.

The substance defats the skin, which may cause dryness or cracking.

NO open flames, NO sparks and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting. Prevent build-up of electrostatic charges (e.g., by grounding). Do NOT use compressed air for filling, discharging, or handling. Use non-sparking handtools.

PREVENT GENERATION OF MISTS!

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

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. Cyclohexene is produced, as an intermediate or a final product, by process units covered under this subpart.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 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.

Cyclohexene has been detected in 2 of 46 US industrial effluent samples; electronics effluent at 83 ng/uL and at 1476 ng/uL(1). Cyclohexene was qualitatively detected in roadside ambient air samples(2), and air samples taken in the Allegheny Mountain Tunnel of the Pennsylvania Turnpike, 1979(3), and in roadway samples in Raleigh, NC, May 1983(4). Cyclohexene was detected at a concentration of 0.19 mg/cu m in the vicinity of an oil fire(5).

SEDIMENT: Cyclohexene was detected in sediment samples taken off the coast of South Africa, Dec to Jan 1975-76, at 10 ng/g dry weight at 8-12 cm depth and 0.1 ng/g at 36-40 cm depth; it was not detected at samples depths of 4-8 or 8-36 cm(1).

Toxicity

LD50 Rat oral 2.4 mL (1946 mg)/kg|LD50 Mouse oral >3.2 mL (2595 mg)/kg|LD50 Guinea pig oral >20 mL (16220 mg)/kg

Cyclohexene's production and use as an intermediate in the manufacture of adipic acid, maleic acid, and hexahydrobenzoic acid(1) may result in its release to the environment through various waste streams(SRC).|OCCURS IN COAL TAR.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 850(SRC), determined from a log Kow of 2.86(2) and a regression-derived equation(3), indicates that cyclohexene is expected to have low mobility in soil(SRC). Volatilization of cyclohexene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 4.55X10-2 atm-cu m/mole(4). Cyclohexene is expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 89 mm Hg(5). A 0% theoretical BOD in 4 weeks using an activated sludge inoculum and the Japanese MITI test(6), suggests that biodegradation is not a fast process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 850(SRC), determined from a log Kow of 2.86(2) and a regression-derived equation(3), indicates that cyclohexene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 4.55X10-2 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 hour and 4 days, respectively(SRC). According to a classification scheme(5), BCF values ranging from 23-45 measured in fish(6), suggests bioconcentration in aquatic organisms is low to moderate(SRC). A 0% theoretical BOD in 4 weeks using an activated sludge inoculum and the Japanese MITI test(6), suggests that biodegradation is not a fast process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyclohexene, which has a an extrapolated vapor pressure of 89 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cyclohexene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals, ozone, and nitrate radicals(SRC). The half-life for the reaction with hydroxyl radicals is estimated to be 6 hours(SRC), calculated from its rate constant of 6.77X10-11 cu cm/molecule-sec(3). The half-life for the reaction with ozone is estimated to be 2 hours(SRC), calculated from its rate constant of 2.04X10-16 cu-cm/molec-sec(4). The half-life for the reaction with nitrate radicals is estimated to be 4 hours(SRC), calculated from its rate constant of 1.9X10-12 cu-cm/molec-sec(5).

The rate constant for the vapor-phase reaction of cyclohexene with photochemically-produced hydroxyl radicals has been measured as 6.77X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of cyclohexene with ozone has been measured as 2.04X10-16 cu-cm/molec-sec at 21 °C(2). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 7X10+11 molec/cu-cm(2). An experimental rate constant of 1.9X10-12 cu-cm/molec-sec at 25 °C(3) has been measured for the gas-phase reaction of cyclohexene with nighttime nitrate radicals. This corresponds to an atmospheric half-life of about 4 hours at an atmospheric concentration of 2X10+8 nitrate radicals per cu cm(4). Cyclohexene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(5). Cyclohexene does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(5). Products from the reaction of cyclohexene with ozone are adipaldehyde, glutaraldehyde, pentanal, formic acid, carbon monoxide, carbon dioxide, 6-oxohexanoic acid, adipic acid, 5-oxopentanoic acid, and glutaric acid(6-8).

BCF values ranging from 23-45 and 12-38 were measured for carp exposed to 10 and 100 ug/L, respectively of cyclohexene during a 28 day incubation period(1). According to a classification scheme(2), this BCF range suggests bioconcentration in aquatic organisms is low to moderate(SRC).

The Koc of cyclohexene is estimated as 850 (SRC), using a log Kow of 2.86(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cyclohexene is expected to have low mobility in soil(SRC).

The Henry's Law constant for cyclohexene is 4.55X10-2 atm-cu m/mole at 25 °C(1). This Henry's Law constant indicates that cyclohexene is expected to volatilize rapidly from water surfaces(2). 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)(2) is estimated as 1 hour(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 4 days(SRC). Cyclohexene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Cyclohexene is expected to volatilize from dry soil surfaces(SRC) based upon a an extrapolated vapor pressure of 89 mm Hg(3).

DRINKING WATER: Cyclohexene has been qualitatively detected in drinking water(1). Detected in drinking water, date and location not provided, at a concentration of 0.13 ug/L(2).|GROUNDWATER: Cyclohexene was detected at levels ranging from 0.00317 to 2.29 mg/L in groundwater at a Marine Corp base in Beaufort, SC(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 517 workers (239 of these are female) may be exposed to cyclohexene in the USA(1). Occupational exposure to cyclohexene may occur through inhalation and dermal contact with this compound at workplaces where cyclohexene is produced or used(SRC).|Cyclohexene was detected in the air of the vulcanization area of a shoe-sole factory at concn of 3-12 ug/cu m(1).

Name Type of Test Exposure Route Species Observed Dose/Duration Toxic Effects Reference
OTHER MULTIPLE DOSE TOXICITY DATA TCLo - Lowest published toxic concentration Inhalation Rodent - rat 600 ppm/6H/26W-I Nutritional and Gross Metabolic--weight loss or decreased weight gain
Biochemical-Enzyme inhibition, induction, or change in blood or tissue levels-phosphatases
Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 37,155,1976

Drug Information

Cyclohexene is readily adsorbed following skin, eye, or respiratory exposure or following ingestion.|These hydrocarbons are poorly absorbed from the GI tract and do not cause appreciable systemic toxicity by this route unless aspiration has occurred.|... Two male Holtzman rats were each given 0.1 mL (81.1 mg/kg bw) of cyclohexene by stomach tube ... The urine sample for 24 hr contained 2-cyclohexen-1-one (0.1 % of the oral dose) but 2-cyclohexen-1-ol was not detected even by beta-glucuronidase treatment.|In an inhalation study, male F344/N rats were exposed nose-only to gaseous cyclohexene at 600 ppm (2,015 mg/cu m) for 60 minutes ... During exposure, the blood levels of cyclohexene increased up to 2 ug/g blood.

Following incubation of Aspergillus niger with cyclohexene, 3 transformation products were isolated: 2-cyclohexen-1-one, (+)-2-cyclohexen-1-ol, and (+)-3-cyclohexene-1,2-cis-diol.|Microsomal oxidases have been detected in the rabbit liver, which readily hydroxylate cyclohexene and a number of related aromatic compounds to the corresponding dihydroxy derivatives.|Hydroxylation of cyclohexene @ allylic position occurred in hepatic microsomes & 9000 g supernatant fractions of rats & rabbits. Formation of product, 2-cyclohexen-1-ol, required presence of NADPH-generating system, was inhibited by CO, and induced by phenobarbital.|In the rabbit, hydroxylation and conjugation occur, with the formation of sulfur-containing metabolites.|Hydroxylated and conjugated metabolites are eliminated in the urine ...

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: 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. (ERG, 2016)

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, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and 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.


Remove contaminated clothes. 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.

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. Administer activated charcoal ... . Treat frostbite with rapid rewarming techniques ... ./Aliphatic hydrocarbons 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 ... . /Aliphatic hydrocarbons and related compounds/|Remove contaminated clothes. Rinse and then wash skin with water and soap.

/SIGNS AND SYMPTOMS/ Hydrophobic hydrocarbons of this type would be expected to induce pulmonary damage, transient CNS depression of excitement, and secondary effects of hypoxia, infection, pneumatocele formation, and chronic lung dysfunction. Cardiac complications are rare.[Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:178]|/SIGNS AND SYMPTOMS/ ACUTE ... SYMPTOMS: Inhalation--cough and drowsiness; Skin--redness and dry skin; Eyes--redness; Ingestion--drowsiness, labored breathing and nausea.[IPCS, CEC; International Chemical Safety Card on Cyclohexene. (October 1999). Available from, as of October 04, 2006: http://www.inchem.org/documents/icsc/icsc/eics1054.htm]|/SIGNS AND SYMPTOMS/ EFFECTS OF SHORT-TERM EXPOSURE: /Cyclohexene/ irritates the eyes, the skin and the respiratory tract. Swallowing the liquid may cause aspiration into the lungs with the risk of chemical pneumonitis ... /It/ may cause effects on the central nervous system. EFFECTS OF LONG-TERM OR REPEATED EXPOSURE: The liquid defats the skin.[IPCS, CEC; International Chemical Safety Card on Cyclohexene. (October 1999). Available from, as of October 04, 2006: http://www.inchem.org/documents/icsc/icsc/eics1054.htm]|/BIOMONITORING/ Hydroxylated and conjugated metabolites are eliminated in the urine and may be quantitated by gas or high pressure liquid chromatography.[Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:177]|/OTHER TOXICITY INFORMATION/ Toxicity ... is low, although it is an irritant, and defats the skin on direct contact. It is an anesthetic and CNS depressant. When ingested, it represents a low to moderate pulmonary aspiration hazard.[Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:177]

cyclohexene

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

irritation eyes, skin, respiratory system; drowsiness


Cough. Drowsiness.


Redness. Dry skin.


Redness.

Eyes, skin, respiratory system, central nervous system

Cyclohexene Use and Manufacturing

Methods of Manufacturing

Cyclohexene is prepared by dehydration of cyclohexanol by thermal reaction of a ethylene-propylene-butadiene mixture.|Prepared by dehydration of cyclohexanol at high temps over various catalysts.|In Japan, cyclohexene is synthesized in a closed system by catalytic hydrogenation of benzene, isolated by fractionation.

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) GREATER THAN 1.4X10+6 GRAMS|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3368]

Grade: Technical 95%; 99%; research 99.9 mole%.|CYCLOHEXENE: 99+% (GOLD LABEL), 99%; BOTH INHIBITED WITH 0.01% 2,6-DI-TERT-BUTYL-4 METHYLPHENOL|CYCLOHEXENE: 99.5% ASSAY; INHIBITOR-SODIUM HYDROXIDE

Cyclohexene: ACTIVE|Cyclohexene occurs in coal tar.|In Japan, cyclohexene is synthesized in a closed system by catalytic hydrogenation of benzene, isolated by fractionation, stored temporarily in storage tanks and used solely as an intermediate for cyclohexanol synthesis in the same factory. Workers take quality control samples of fractionated cyclohexene once a day and stored cyclohexene once a month. ... Workers wear goggles and protecting gloves during sampling, exposure through dermal contact is therefore expected to be minimal.

MONITORING METHOD: ANALYTE: CYCLOHEXENE; MATRIX: AIR; RANGE: 510-2030 MG/CU M; PROCEDURE: ADSORPTION ON CHARCOAL, DESORPTION WITH CARBON DISULFIDE, GAS CHROMATOGRAPHY.|NIOSH Method #1500. Hydrocarbons 36-126 °C BP. Gas chromatography with FID detection, estimated limit of detection 0.001 - 0.01 mg/sample with capillary column.|Cyclohexene can be quantified using IR and UV spectroscopy, coulometric titration, NMR spectroscopy, and gas chromatography.

Fire Hazards -> Flammable - 3rd degree

Computed Properties

Molecular Weight:82.14
XLogP3:2.9
Exact Mass:82.078250319
Monoisotopic Mass:82.078250319
Heavy Atom Count:6
Complexity:45.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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