Vinylcyclohexene

108.18

108.18

202-848-9

1177

15760

1993

DTXSID3021437

Liquid

29021900

0

3.93

Off-white to beige-brownish Powder

0.8299 g/cm³ @ Temp: 20 °C

-108.9 °C

128 °C @ Press: 760 Torr

68 °F

n 20/D 1.463(lit.)

Solubility in water: none

2-8°C

10.2 mm Hg ( 25 °C)

3.76 (vs air)

Oral-Rat LD50: 2563 mg/kg; inhalation-mouse LC50: 27 g/m3

Inflammable in case of open flame, high temperature, oxidant; burning produces irritating smoke

Conversion factor: 4.43 mg/cu m = 1 ppm

4-Vinyl cyclohexene|D: Other compounds that may form peroxides|Kelly|American Conference of Governmental Industrial Hygienists, Inc. Documentation of the Threshold Limit Values and Biological Exposure Indices. 6th ed. Volumes I, II, III. Cincinnati, OH: ACGIH, 1991., p. 1703

517 °F (269 °C).|269 °C

The vapour mixes well with air, explosive mixtures are easily formed.

II

3.1

UN 1993 3/PG 2

2

11-38-40-65-62-52/53

16-33-36/37-62

GW6650000

F,Xn

The warehouse is ventilated, low temperature and dry; stored separately from oxidants and acids

OXIDIZES IN AIR TO FORM HYDROPEROXIDE

P201-P210-P273-P301 + P310-P308 + P313-P331

H225-H304-H315-H351-H361-H412

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/

Can react with oxidizers.|Upon contact with oxygen, VCH undergoes auto-oxidation to produce vinylcyclohexene hydroperoxide. The hydroperoxide can be formed during prolonged storage of butadiene, & further autocondensation leads to 1,2,3,6,1',2',3',6'-octahydrobiphenyl.

DHHS/NTP; Toxicology & Carcinogenesis Studies of 4-Vinylcyclohexene in F344/N Rats (Gavage Studies) Technical Report Series No. 303 (1986) NIH Publication No 86-2559

Highly flammable. Vapour/air mixtures are explosive.|Carcinogens, Flammable - 3rd degree, Reactive - 2nd degree

|Warning|H351: Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|Danger|H225 (76.3%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P281, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P331, P332+P313, P337+P313, P362, P370+P378, P391, P403+P235, P405, and P501|Aggregated GHS information provided by 429 companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P264, P280, P281, P302+P352, P308+P313, P321, P332+P313, P362, P405, and P501|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P281, P302+P352, P303+P361+P353, P305+P351+P338, P308+P313, P310, P312, P314, P321, P332+P313, P362, P370+P378, P403+P235, P405, and P501|H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

FLAMMABLE, DANGEROUS FIRE RISK.|DANGEROUS FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME

Explosive limits , vol% in air: 0.8-9.1

To fight fire, use foam, CO2, dry chemical.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for 4-VINYL-1-CYCLOHEXENE (10 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

It is an irritant, and it defats the skin on direct contact.

Consult an expert! Remove all ignition sources. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations.

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

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

The substance is irritating to the skin. The substance is mildly irritating to the eyes. If swallowed the substance easily enters the airways and could result in aspiration pneumonitis.

Animal tests show that this substance possibly causes toxic effects upon human reproduction. This substance is possibly carcinogenic to humans.

NO open flames, NO sparks and NO smoking. NO contact with oxidizing agents. Closed system, ventilation, explosion-proof electrical equipment and lighting. Do NOT use compressed air for filling, discharging, or handling.

STRICT HYGIENE!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 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.| 2 - Materials that readily undergo violent chemical changes at elevated temperatures and pressures.|W - No water: Materials that react violently or explosively with water.| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.

The concn of 4-vinylcyclohexene in air emissions from extruded ABS composite resins was between 0.26-6.50 ug/l(1). The quasi steady-state emission rate of 4-vinylcyclohexene from new carpets (measured in an environmental chamber) ranged 7.3-24.2 and 0.6-2.7 ug/sq m per hr after 24 and 168 hours of equilibration, respectively(2).

INDOOR AIR: The indoor air concn of 4-vinylcyclohexene was 0.27 ppb in a freshly carpeted 20 cu m stainless-steel room after a 168 hours equilibration period(1).

moderately toxic

LD50 Rat (Carworth-Wistar) oral 1.6 g/kg|LD50 Rat oral 2563 mg/kg|LD50 Rabbit skin 16,640 mg/kg

Toxicology and carcinogenesis studies of 4-vinylcyclohexene (greater than 98% pure), a dimer of 1,3-butadiene present in the off-gases from tire curing, were conducted by administering the chemical in corn oil by gavage 5 days per week at doses of 0, 200, or 400 mg/kg body weight to groups of 50 F344/N rats for 103 weeks. ... Many dosed rats died early in the 2 year studies (male: vehicle control, 17/50; low dose, 37/50; high dose, 45/50; female: vehicle control, 10/50; low dose, 22/55; high dose, 36/50; P<0.001 for all groups except low dose female rats, for which p= 0.022). The poor survival of dosed male and female rats reduced the sensitivity of the studies for detecting the possible carcinogenic effects of 4-vinylcyiclohexene. Mean body weights of dosed rats were comparable to those of their respective vehicle controls, except for high dose males late in the study. Administration of 4-vinycyclohexene ... was associated with a slightly increased incidence of epithelial hyperplasia of the forestomach (1/50; 3/50; 5/47) and squamous cell papillomas or carcinomas (combined) of the skin in high dose males (0/50; 1/50; 4/50). Low dose female rats whose survival was more similar to that of the vehicle controls, had a marginally increased incidence of adenomas was more similar to that of the vehicle controls, had a marginally increased incidence of adenomas or squamous cell carcinomas (combined) of the clitoral gland (1/50; 5/50; 0/49). ... Under these conditions, the 2 year gavage studies of 4-vinylcyclohexene in male and female rats ... were considered inadequate studies of carcinogenicity because of extensive and early mortality at the high dose or at body doses and the lack of conclusive evidence of a carcinogenic effect.|Toxicology and carcinogenesis studies of 4-vinylcyclohexene (greater than 99% pure), a dimer of 1,3-butadiene present in the off-gases from tire curing, were conducted by administering the chemical in corn oil by gavage 5 days per week at doses of 0, 200, or 400 mg/kg body weight to groups of 50 B63F1 mice of each sex for 103 weeks. ... Survival of high dose mice of each sex was lower (p< 0.001) than that of the vehicle controls, whereas survival of low dose mice of each sex was comparable to that of the vehicle controls. Mean body weights of high dose mice of each sex were generally lower than those of the vehicle controls throughout most of the 2 year studies. ... In B6C3F1 mice, administration of 4-vinylcyclohexene ... was associated with mild, acute inflammatory lesions and epithelial hyperplasia of the forestomach, especially in males (0/47; 7/50; 7/46), and with an increased incidence of a number of other nonneoplastic lesions including lung congestion in high dose males and females, splenic red pulp atrophy in high dose males, congestion of the adrenal gland in high dose females and cytologic alteration of the adrenal cortex in low dose and high dose females. ... The incidences of uncommon ovarian neoplasms were markedly increased (p< 0.01) in both groups of dosed female mice (mixed tumor, benign: 0/49; 25/48, 52%; 11/47, 23%; granulosa cell tumor: 1/49, 2%; 9/48, 19%; 11/47, 23%; granulosa cell tumor or carcinoma [combined]: 1/49, 2%; 10/48, 21%; 13/47, 28%). In addition, a slight increase in the incidence of adrenal gland adenomas in high dose females was observed (0/50; 3/39, 6%; 4/48, 8%). The extensive mortality seen in the high dose male mice confounded interpretation of the increased incidences of malignant lymphomas and alveolar/bronchiolar adenomas or carcinomas (combined) of the lung seen in these animals surviving to the end of the study (malignant lymphomas: 3/37, 8%; 5/39, 13%; 4/7, 57%; alveolar/bronchiolar adenomas or carcinomas [combined]: 3/37, 8%; 9/39, 23%; 3/7, 43%). ... Under these conditions, the 2 year gavage studies of 4-vinylcyclohexene in ... male mice were considered inadequate studies of carcinogenicity because of extensive and early mortality at the high dose or at both doses and the lack of conclusive evidence of a carcinogenic effect. There was clear evidence of carcinogenicity of 4-vinylcyclohexene for female mice, as shown by markedly increased incidences of uncommon ovarian neoplasms at both doses. In addition, the increased incidence of adrenal gland adenomas in high dose female mice may have been related to the administration of 4-vinylcyclohexene.|4-Vinylcyclohexene (VCH) was evaluated for reproductive toxicity in CD-1 mice using a continuous breeding protocol. VCH was administered to the animals by gavage in corn oil at doses of 0, 100, 250, or 500 mg/kg/day. Exposure to VCH for 14 wks did not significantly affect measures of reproductive competence. including initial fertility, mean number of litters/pair, live litter size, the proportion of pups born alive, or adjusted live pup weight. Absolute live pup weight was decreased (males & sexes combined) at the high dose. F0 feed & water consumption were not adversely affected by treatment. At necropsy, the F0 females in the high-dose group had slightly decreased body weight. VCH did not adversely affect preweaning growth or survival in the F1 generation. High-dose (500 mg/kg/day VCH) males, selected on postnatal day 21 for inclusion in Task 4, had decreased body weight throughout Task 4 to scheduled necropsy. F1 females selected from the high-dose group for inclusion in Task 4 had decreased body weight beginning at 74+/-10 days of age through Task 4 to necropsy. There was no effect of VCH treatment on feed or water consumption. VCH had no effect on the reproductive competence of the F1 generation; adjusted live pup weight for females & the sexes combined was slightly but significantly depressed in the VCH-treated litters. At necropsy, relative, but not absolute, liver weight (males & females) & sperm motility were increased in the VCH-treated group; testicular spermatid count was decreased by VCH treatment. The number of primordial, growing, & antral oocytes was significantly reduced in VCH-treated females. VCH at doses up to 500 mg/kg/day had no significant adverse effect on reproductive competence in either the F0 or F1 generation. For the F1 males & females, this was in spite of a slight but significant reduction in spermatid head count (83% of control) & ovarian follicles (46-67% of control), respectively. F0 females receiving 500 mg/kg/day exhibited slight general toxicity manifested as an 8% decr in body weight after 18 wks treatment. F1 males & females receiving 500 mg/kg/day VCH exhibited generalized toxicity manifested as an 8-10% decr in body weight throughout Task 4. These data indicate that VCH did not cause a detectable decr in reproductive competence in the F0 generation, nor was reproductive function adversely affected in F1 mice at doses that caused decreased body weight & ovarian & testicular toxicity.

IT IS FORMED ON PROLONGED STORAGE OF BUTADIENE ... .|4-Vinylcyclohexene's production and use in polymers and organic synthesis(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3300(SRC), determined from an measured log Kow of 3.93(2) and a regression-derived equation(3), indicates that 4-vinylcyclohexene is expected to have slight mobility in soil(SRC). Volatilization of 4-vinylcyclohexene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.5X10-2 atm-cu m/mole(SRC), derived from its vapor pressure, 15.7 mm Hg(4), and water solubility, 50 mg/l(5). The potential for volatilization of 4-vinylcyclohexene from dry soil surfaces may exist(SRC) based upon its vapor pressure(4). 4-Vinylcyclohexene, present at 100 mg/l, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the modified Japanese MITI test(2). Therefore, this compound should not biodegrade rapidly in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3300(SRC), determined from a measured log Kow of 3.93(2) and a regression-derived equation(3), indicates that 4-vinylcyclohexene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.5X10-2 atm-cu m/mole(SRC), derived from its vapor pressure, 15.7 mm Hg(4), and water solubility, 50 mg/l(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1.1 hours and 4.1 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 571(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC). 4-Vinylcyclohexene, present at 100 mg/l, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the modified Japanese MITI test(2). Therefore, this compound is not expected to biodegrade rapidly in aqueous systems(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-vinylcyclohexene, which has a vapor pressure of 15.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 4-vinylcyclohexene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC). The half-life for reaction in air with hydroxyl radicals is estimated to be 4.3 hours(SRC), calculated from its rate constant of 8.93X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). The half-life for reaction in air with ozone is estimated to be 1.3 hours(SRC), calculated from its rate constant of 2.12X10-16 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 4-vinylcyclohexene with photochemically-produced hydroxyl radicals has been estimated as 8.93X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 4-vinylcyclohexene with photochemically-produced ozone has been estimated as 2.12X10-16 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.3 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). 4-Vinylcyclohexene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).

165.96|An estimated BCF of 571 was calculated for 4-vinylcyclohexene(SRC), using a log Kow of 3.93(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).

The Koc of 4-vinylcyclohexene is estimated as 3300(SRC), using a measured log Kow of 3.93(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-vinylcyclohexene is expected to have slight mobility in soil(SRC).

The Henry's Law constant for 4-vinylcyclohexene is estimated as 4.5X10-2 atm-cu m/mole(SRC), derived from its vapor pressure, 15.7 mm Hg(1), and water solubility, 50 mg/l(2). This Henry's Law constant indicates that 4-vinylcyclohexene is expected to volatilize rapidly from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 1.1 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 4.1 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 19 days if adsorption is considered(4). 4-Vinylcyclohexene's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 4- vinylcyclohexene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 15.7 mm Hg(1).

Occupational exposure to 4-vinylcyclohexene may occur through inhalation and dermal contact with this compound at workplaces where 4-vinylcyclohexene, acrylonitrile-butadiene-styrene, or rubber compounds are produced or used(SRC). Concn of 4-vinylcyclohexene in workplace air averaged between 1.2-2.4 g/cu m and occasionally reached 3 g/cu m(1). The concn of 4-vinylcyclohexene was between 30-210 ug/cu m in the workplace air of shoe-sole factories that use polyisoprene, styrene-butadiene, and cis-polybutadiene polymers(2). The mean concn of 4-vinylcyclohexene in workplace air during rubber vulcanization at a tire manufacturing facility was between 71-92 ppb(3). Consumers may be exposed to 4-vinylcyclohexene from volatiles from carpets based on monitoring data(SRC).

A single oral dose of 400 mg/kg 4-[ethylene-C]VCH (99%, containing tert-butylcatechol as antioxidant) in corn oil was given to fasted female B6C3F1 mice & female F344 rats. The mice excreted 95% of the admin dose within 24 hr, & the rats excreted 95% of the dose within 48 hr via urine (50-60%) & expired air (30-40%). Negligible amounts of VCH appeared as CO2; fecal elimination accounted for 3% to 9% of the dose. Total tissue radioactivity in mice at 24 hr constituted <1% of the dose; in rats 3.4%, 1.1%, & 1.1% of the dose was retained in adipose tissue, skeletal muscle, & skin, respectively. Neither parent VCH nor its metabolites accumulated in the ovaries of either species [accounting for 0.05% of the admin dose], & there were no species-specific differences in ovarian distribution.|A single dose of 400 mg/kg body weight (14)C-4-vinylcyclohexene given by oral gavage in corn oil to fasted female B6C3F1 mice and Fischer 344 rats resulted in peak blood levels of about 100 nmol/ml between 1 and 2 hours after administration. Mice eliminated 95% of the radioactivity within 24 hours, whereas rats required 48 hours. The main routes of excretion of the radioactivity were the urine (50-60%) and expired air (30-40%). The concentration of 4-vinylcyclohexene was highest in adipose tissue (about 5 umol/g), which was about 10 times higher than that in tissues such as liver, skin and ovary.

WHEN 4-VINYLCYCLOHEXENE & 4-VINYLCYCLOHEXANE MONOXIDE WERE ADMIN TO MICE AT 500 MG/KG, CYTOCHROME p450, CYTOCHROME B5, NADPH-CYTOCHROME C REDUCTASE, AMINOPYRINE-N-DEMETHYLASE & EPOXIDE HYDROLASE WERE INDUCED. DOSES OF 500 MG/KG 4-VINYLCYCLOHEXENE, 4-VINYLCYCLOHEXENE MONOXIDE & 4-VINYLCYCLOHEXENE DIEPOXIDE DEPLETED HEPATIC REDUCED GLUTATHIONE LEVELS SUGGESTING THAT GLUTATHIONE WAS PROBABLY INVOLVED IN METABOLISM OF 4-VINYLCYCLOHEXENE.|THE MAIN 4-VINYL-1-CYCLOHEXENE METABOLITE FORMED IN MICE LIVER MICROSOMES AFTER INCUBATION WAS 4-VINYLCYCLOHEXANE-1,2-DIOL. OTHER METABOLITES WERE 4-VINYL-1,2-EPOXYCYCLOHEXANE & 4-VINYL-1-CYCLOHEXENE DIOXIDE. 4-VINYL-1-CYCLOHEXENE DIOXIDE INCREASED (APPROX 10 TIMES) THE FORWARD MUTATION RATE OF V79 CHINESE HAMSTER CELLS.|4-Vinylcyclohexene is metabolized in vitro by liver microsomal enzymes. The major metabolic products are 4-vinyl-1,2-epoxycyclohexane and 4-epoxyethyl-1,2-dihydroxycyclohexane, with trace amounts (less than 0.001%) of vinylcyclohexene diepoxide also being produced.|Wistar rat and Swiss mouse liver microsomal mixed function oxidase metabolize 4-vinylcyclohexene ... to 4-vinyl-1,2-epoxycyclohexane ..., 4-epoxyethylcyclohexene and traces of 4-epoxyethyl-1,2-epoxycyclohexane. These are further hydrolysed by epoxide hydrolase to the corresponding diols: 4-vinylcyclohexane-1,2-diol, 4-dihydroxyethylcyclohexene ... and possibly 4-epoxyethylcyclohexane-1,2-diol. The last two metabolites may be further metabolized to 4-dihydroxyethyl-1,2-epoxycyclohexane and the tetrol 4-dihydroxyethylcyclohexane-1,2-diol.|For more Metabolism/Metabolites (Complete) data for 4-VINYL-1-CYCLOHEXENE (6 total), please visit the HSDB record page.|4-VINYLCYCLOHEXENE has known human metabolites that include 1,2-Epoxy-4-vinylcyclohexane and Epoxy-4-vinylcyclohexene.

0.39 Days

VINYLALICYCLIC OLEFINS DESTROYED HEPATIC CYTOCHROME P450 FROM PHENOBARBITAL-PRETREATED MALE MICE, IN PRESENCE OF NADPH; THE LOSS OF THE ENZYME WAS ALWAYS ACCOMPANIED BY A QUANTITATIVELY CORRELATED LOSS OF MICROSOMAL HEME. THE COMPOUNDS (INCL 4-VINYL-1-CYCLOHEXENE) CAUSED MUCH SMALLER LOSSES OF CYTOCHROME P450 & HEME IN 3-METHYLCHOLANTHRENE-MICROSOMES THAN WITH PHENOBARBITAL ONES. THE EFFECT HAS BEEN SHOWN TO BE SPECIFIC FOR CYTOCHROME P450, IT IS NOT STIMULATED BY NADH, IT IS INHIBITED BY CARBON MONOXIDE, METYRAPONE, & IT SHOWS PSEUDO FIRST-ORDER KINETICS. THE EPOXIDES OF THE PARENT ACTIVE OLEFINS DID NOT INTERVENE IN THE DESTRUCTION OF THE ENZYME. THE INABILITY OF THE EPOXIDES RELATED TO THESE OLEFINS TO DESTROY CYTOCHROME P450 & THEIR STABILITY STRENGTHENS THE HYPOTHESIS THAT AN INTERMEDIATE ZWITTERION SPECIES IS RESPONSABLE FOR THE DESTRUCTIVE PROCESS BEFORE THE OXIRANE RING FORMATION.

Fresh air.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

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. 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 shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline 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 ... . /Aliphatic hydrocarbons and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory rest. Positive pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aliphatic hydrocarbons and related compounds/

It is an irritant, and it defats the skin on direct contact. It is a anesthetic and CNS depressant. When ingested, it represents a low to moderate pulmonary aspiration hazard.|Russian rubber workers inhaling mean VCH concn of 271 to 542 ppm (with peak VCH concn to 677 ppm) were reported to suffer from keratitis, rhinitis, headache, hypotonia, leukopenia, neutrophilia, lymphocytosis, and "impairment of pigment and carbohydrate metabolism."

4-ethenyl-1-cyclohexene

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

Cough. Headache.

Redness.

Redness.

Grades: Technical, 95%; Pure, 99%; Research.

All other basic organic chemical manufacturing|Cyclohexene, 4-ethenyl-: ACTIVE

GC was used to determine the quantity of 4-vinylcyclohexene formed from butadiene by its dimerization in the GC.|Quick simple method using GC with flame ionization for determination of 4-vinyl-1-cyclohexane in air. Sensitive to 1 ppm using 1 ml of air.

Fire Hazards -> Carcinogens, Flammable - 3rd degree, Reactive - 2nd degree