Vinylcyclohexene diepoxide

140.18

140.18

203-437-7

596C064IG4

0820

61281|54752|7583

2810

DTXSID0020604

COLORLESS LIQUID|Colorless liquid.

2932999099

25.1

0.8

1-vinyl-3-cyclohexene dioxide is a clear colorless liquid. Sets to glass at -67°F. Faint olefinic odor. (NTP, 1992)

1.0986 g/cm³ @ Temp: 20 °C

<-55 °C

227 °C @ Press: 760 Torr

225 °F

n 20/D 1.477(lit.)

High

Vapour pressure, kPa at 20°C:

4.07

Oral-Rat LD50: 2130 mg/kg; inhalation-rat LC50: 800 ppm/4 hours

Flammable; burning emits irritating smoke

SETS TO GLASS @ -55 °C|1 PPM APPROX= 5.73 MG/CU M @ 25 °C, 760 MM HG & 1 MG/L APPROX= 174 PPM @ 25 °C, 760 MM HG|REACTS WITH ACTIVE HYDROGEN COMPD (EG, ALCOHOLS, AMINES)

Water soluble. Hydrolyzes slowly in water.

Epoxides

Polymerizable

1-VINYL-3-CYCLOHEXENE DIOXIDE reacts with active hydrogen compounds (such as alcohols and amines). (NTP, 1992). Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

393 °C

Class IIIB Combustible Liquid: Fl.P. at or above 200°F.

III

6.1(b)

UN 2810 6.1/PG 3

1

23/24/25-68/20/21/22-68

23-24-45

RN8640000

T

Warehouse low temperature, ventilated, dry

Exothermic polymerization, closed container can explode

Stable. Combustible. Incompatible with strong oxidizing agents, alcohols, amines and other compounds containg an active hydrogen. Hydrolyzes slowly in water.

P201, P202, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, P501

H301

Alcohols, amines, water [Note: Slowly hydrolyzes in water].

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 4-Vinyl-1-cyclohexene Diepoxide (106-87-6) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s187vch.pdf]|NTP TR No 362; Route: skin paint; Species: rats and mice. NTIS No PB90219957/AS.[NTP; Division of Toxicology Research and Testing; Management Status Report; 07/22/92; p.27]

This chemical is combustible. (NTP, 1992)|Combustible. Risk of fire and explosion on contact with acids or bases.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P314, P321, P322, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. 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)

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and protect it from moisture. (NTP, 1992)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]|For more Personal Protective Equipment (PPE) (Complete) data for VINYLCYCLOHEXENE DIOXIDE (6 total), please visit the HSDB record page.|(See protection codes)

Slight, when exposed to heat or flame.

To fight fire: Water, foam, dry chemical.

The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.

STRONG IRRITANT TO SKIN & TISSUE.

Vacated 1989 OSHA PEL TWA 10 ppm (60 mg/cu m), skin designation, is still enforced in some states.

NIOSH considers vinyl cyclohexene to be a potential occupational carcinogen.|NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.|Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 ppm (60 mg/cu m), skin.

Personal protection: complete protective clothing including self-contained breathing apparatus. Ventilation. Collect leaking liquid in sealable containers. Wash away remainder with plenty of water.

Separated from food and feedstuffs, alcohols, amines and other active hydrogen compounds. Dry. Ventilation along the floor.

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 eyes, skin and respiratory tract. Inhalation may cause lung oedema. Exposure at high levels could cause death. The effects may be delayed. Medical observation is indicated.

The substance may have effects on the kidneys, ovary and testes. This may result in tissue lesions. This substance is possibly carcinogenic to humans. Animal tests show that this substance possibly causes toxic effects upon human reproduction.

NO open flames.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

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

moderately toxic

LD50 Rat oral 2.8 g/kg|LD50 Rabbit dermal 0.06 ml/kg|LD50 Rat oral 2130 mg/kg|LC50 Rat oral inhalation 800 ppm/4 hr|LD50 Rabbit dermal 620 mg/kg

Two-year studies were conducted by administrating 4-vinyl-1- cyclohexene diepoxide in acetone by dermal application, 5 days per week to groups of 60 rats of each sex at 0, 15, or 30 mg/animal. Groups of 60 mice of each sex were administered 0, 2.5, 5, or 10 mg/animal on the same schedule for 103 weeks. None of the doses selected had produced ulceration of skin in 13 week studies. ... In general, the body weights and survival were lower in mid and high dose groups than in vehicle controls. The survival was lower in exposed groups, primarily because of neoplasms (survival at week 105 male rats: vehicle control, 7/50; low dose, 8/50; high dose, 4/50; female rats: 27/50; 23/50; 15/50; male mice; vehicle control 38/50; low dose, 35/50; mid dose, 4/50; high dose, 0/50; female mice; 30/50; 15/50; 0/50). All high dose male mice died by week 83; the 10 surviving high dose female mice were killed during week 85. ... Acanthosis and sebaceous gland hypertrophy of skin from the scapula or back were observed at substantially increased incidences in exposed male and female rats. Squamous cell papillomas in male rats and squamous cell carcinomas in male and female rats were observed only in exposed rats (squamous cell carcinomas--male: vehicle control 0/50; low dose 33/50; high dose, 36/50; female: 0/50; 16/50). The incidences of basal celladenomas or carcinomas (combined) were increased (male: 0/50; 1/50; 6/50; female: 0/50; 3/50; 4/50). ... For exposed mice, acanthosis, hyperkeratosis, and necrotizing inflammation of the skin were observed over the scapula or back. Squamous cell carcinomas were found only in exposed mice (male: vehicle control, 0/50; low dose, 14/50; mid dose, 39/50; high dose, 42/50; female: 0/50; 6/50; 37/50; 41/50). ... Follicular atrophy and tubular hyperplasia of the ovary in female mice were increased (atrophy: 12/50; 43/49; 42/49; 47/50; tubular hyperplasia: 5/50; 35/49; 34/50). Mid and high dose females had benign or malignant granulosa cell tumors (0/50; 0/49; 7/49; 12/50) and benign mixed tumors (0/50; 0/49; 11/49; 6/50). The combined incidences of luteomas, granulosa cell tumors benign mixed tumors, or malignant granulosa cell tumors in mid and high dose female mice were increased (1/50; 0/49; 17/49; 18/50). The incidences of alveolar/bronchiolar adenomas or carcinomas (combined) in exposed female mice were marginally increased (4/50; 9/50; 11/50; 7/50). ... Under the conditions of these 2 year dermal studies, there was clear evidence of carcinogenic activity of 4-vinyl-1-cyclohexene diepoxide for male and female F344/N rats as shown by squamous cell and basal cell neoplasms of the skin. There was clear evidence of carcinogenic activity of 4-vinyl-1- cyclohexene diepoxide for male and female B6C3F1 mice, as shown by squamous cell carcinomas of the skin in males and squamous cell carcinomas of the skin and ovarian neoplasms in females; increased incidences of lung neoplasms in females may also have been related to chemical application.|The immunotoxic effects of 4-vinyl-1-cyclohexene diepoxide were studied in male B6C3F1 mice after a 5 day dermal exposure at doses ranging from 2.5 to 10 mg/mouse/day. 4-Vinyl-1-cyclohexene diepoxide was immunosuppressive at 10 mg/mouse and, to a lesser extent, at 5 mg/mouse, as indicated by a decrease in peripheral lymphocytes and the in vitro lymphoproliferative response to phytohemagglutinin and concanavalin A in the high dose group and suppression of the antibody plaque-forming-cell response in the 5 and 10 mg/mouse groups.|4-Vinyl-1-cyclohexene diepoxide was mutagenic in Salmonella typhimurium strains TA98, TA100, and TA1535 with and without exogenous metabolic activation; the compound was equivocally mutagenic in strain TA1537 without S9 but gave a positive response in the presence of activation. 4-Vinyl-1-cyclohexene diepoxide induced resistance to trifluorothymidine in mouse L5178Y/TK cells without exogenous metabolic activation; it was not tested with activation. 4-Vinyl-1-cyclohexene diepoxide induced sister chromatid exchanges and chromosomal aberrations in Chinese hamster ovary cells in the presence and absence of exogenous metabolic activation.

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)

4-Vinyl-1-cyclohexene diepoxide is absorbed by rodents exposed dermally orally, or by inhalation. ... Rats and mice received 0.1 ml and 0.01 ml, respectively, of dose mixtures containing 500 mg/ml (200 uc/ml) [ethylene-(14)C] 4-vinyl-1-cyclohexene diepoxide in acetone. The preliminary results indicate that 30% of the dose applied to the skin is absorbed over a 24 hr period for both rats and mice; only 1%-3% of the dose remained on the skin at the site of application. By 24 hr, 70%-80% of the absorbed dose had been eliminated from the body, virtually all in the urine. The radioactivity remaining in the body was distributed over a number of tissues, with no tissue containing more than 1% of the applied dose. The liver, muscle, and adipose tissue, however, contained 0.5%-1.6% and 1.2%-2.9% of the absorbed dose in rat and mouse tissue, respectively. Tissue to blood ratios ranged from 0.3 to 1.5 in rats and from 0.8 to 2.8 in mice.

In vitro studies with rabbit liver microsomal preparations showed that 4-vinyl-1-cyclohexene diepoxide can be metabolized to monoepoxymonoglycols, 1,2-hydroxy-4-vinylcyclohexane oxide, and 4-(1',2'-dihydroxyethyl)-1-cyclohexane oxide. Formation of these products is catalyzed by epoxide hydrolase. Conjugation with glutathione is another pathway for metabolism of 4-vinyl-1- cyclohexene. Depletion of reduced glutathione /was reported/ in the liver of mice given ip injections of 500 mg/kg 4-vinyl-1-cyclohexene diepoxide.|Carcinogenicity studies have shown that chronic administration of 4-vinylcyclohexene will induce ovarian tumors in B6C3F1 mice but not F-344 rats. This occurs because the blood level of the ovotoxic 4-vinylcyclohexene metabolite, 4-vinylcyclohexene-1,2-epoxide, is dramatically higher in 4-vinylcyclohexene treated female mice compared with rats. This species difference in 4-vinylcyclohexene epoxidation is also reflected in the rate of 4-vinylcyclohexene metabolism by hepatic microsomes (female mouse greater than female rat). The present study assessed the ability of microsomes obtained from human liver to metabolize 4-vinylcyclohexene to epoxides since humans are exposed to 4-vinylcyclohexene in certain occupational settings. The production of 4-vinylcyclohexene-1,2-epoxide and 4-vinylcyclohexene-7,8-epoxide from 4-vinylcyclohexene (1 mM) by human hepatic microsomes was linear with respect to microsomal protein concentration (0.25-1.0 mg/ml) and incubation time (5-20 min). 4-Vinylcyclohexene-1,2-epoxide was the major metabolite, while the rate 4-vinylcyclohexene-7,8-epoxide formation was about 6 fold lower and in some cases was below the limit of detection. There was no dramatic difference in the rate of 4-vinylcyclohexene epoxidation by hepatic microsomes obtained from male and female humans. The rate of 4-vinylcyclohexene-1,2-epoxide formation by female human hepatic microsomes was 0.71 + or - 0.35 nmol/mg microsomal protein/min (n = 4). This is 13 and 2 fold lower than the rate of 4-vinylcyclohexene-1,2-epoxide formation by female mouse and rat hepatic microsomes, respectively.|4-Vinylcyclohexene is a chemical to which humans are exposed in the rubber industry. A chronic carcinogenicity bioassay conducted by the NTP showed that oral administration of 4-vinylcyclohexene induced tumors in the ovaries of mice but not in those of rats. The hypothesis tested was that the species and organ specificity of 4-vinylcyclohexene toxicity was due to differences in the disposition of 4-vinylcyclohexene between the female rat and mouse. Therefore, the disposition of a single oral dose of 400 mg/kg (14)C 4-vinylcyclohexene was studied in female B6C3F1 mice and Fischer 344 rats. Mice eliminated greater than 95% of the dose in 24 hr, whereas rats required 48 hr to eliminate greater than 95% of the dose. The major routes of excretion of (14)C 4-vinylcyclohexene derived radioactivity were in the urine (50-60%) and expired air (30-40%). No evidence was obtained to indicate that the ovaries of either species retained 4-vinylcyclohexene as a parent cmpd or as radioactive equivalents. A dramatic difference was observed between the rat and mouse in the appearance of a monoepoxide of 4-vinylcyclohexene in blood from 0.5 to 6 hr after 4-vinylcyclohexene administration (800 mg/kg, ip). 4-Vinylcyclohexene-1,2-epoxide was present in the blood of mice with the highest concentration at 2 hr (41 nmol/ml). The blood concentration of 4-vinylcyclohexene-1,2-epoxide in rats was less than 2.5 nmol/ml at all times examined. 4-Vinylcyclohexene-7,8-epoxide was not present in the blood of either species at the level of detection. These findings were supported by in vitro studies of 4-vinylcyclohexene epoxidation by liver microsomes. The rate of epoxidation of 4-vinylcyclohexene (1 mM) to 4-vinylcyclohexene-1,2-epoxide was 6.5 fold greater in mouse liver microsomes than that in rat liver microsomes. The species difference in the rate of epoxide formation by the liver may be an important factor in the species difference in susceptibility to 4-vinylcyclohexene induced ovarian tumors.|VCH-diepoxide is a known human metabolite of 1,2-Epoxy-4-vinylcyclohexane and Epoxy-4-vinylcyclohexene.

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Target Organs: Eyes, skin, respiratory system, blood, thymus, reproductive system (NIOSH, 2016)|Carcinogens

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)|(See procedures)

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

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

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

HUMAN EXPERIENCE INDICATES THAT IT IS MILD TO MODERATE SKIN IRRITANT ... . ONE CASE OF SEVERE VESICULATION OF SKIN OF BOTH FEET WHEN WORKER WORE SHOES PREVIOUSLY CONTAMINATED WITH THIS COMPD.|TOXIC BY INGESTION & SKIN ABSORPTION. STRONG IRRITANT TO SKIN & TISSUE.|EYE INJURY IS CONSIDERED TO BE DEFINITE HAZARD. IF VAPOR PRESSURE OF 0.1 MM HG AT 20 °C IS CORRECT ... RISK BY INHALATION IS CONSIDERED TO BE SLIGHT. BECAUSE OF VERY LIMITED ... DATA & BECAUSE OF DEMONSTRATED CARCINOGENICITY WHEN ... APPLIED TO SKIN OF MOUSE, EXTREME CAUTION SHOULD BE EXERCISED IN USE OF THIS DIEPOXIDE.|Allergic contact dermatitis occurred in an electron microscopist after exposure to the cycloaliphatic epoxy, vinyl cyclohexane diepoxide. Cycloaliphatic epoxies are not based on the diglycidyl ether of bisphenol A, presently the epoxy of greatest commercial usage. Latex or polyvinyl chloride gloves did not protect the reported patient from precutaneous absorption and elicitation of allergic dermatitis.|A study of occupational exposure to sensitizing chemicals was conducted. The study was initiated because of numerous complaints of eye, nasal, skin, and respiratory irritation among workers at an industrial facility. Serum samples were obtained from 31 workers and assayed for immunoglobulin G and immunoglobulin E to an unspecified number of chemicals. An enzyme linked immunosorbent assay technique was used to detect the antibodies. Immunoglobulin G and immunoglobulin E antibodies against four chemicals were found: an aliphatic diisocyanate, 4-vinylcyclohexene-dioxide, trimellitic anhydride, and an unknown substance which was a component of n-octyl-n-decyl-trimellitate. The presence or absence of antibodies could not be correlated with the presence or absence of symptoms; however, the highest incidence of symptoms occurred in workers who were classified as having the highest exposures. It was noted that trimellitic anhydride is not known to be present at the facility. The source of the trimellitic anhydride response is not known. It was concluded that there is no occupational allergic disease in the worker population. The lack of correlation between the antibody responses and symptoms suggests that an immunologic factor is not the cause of the reported symptoms. The symptoms are more likely to be due to irritant nonimmunological reactions.

1-epoxyethyl-3,4-epoxycyclohexane

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

In Animals: irritation eyes, skin, respiratory system; testicular atrophy; leukopenia (reduced blood leukocytes), necrosis thymus; skin sensitization; [potential occupational carcinogen]

Cough. Laboured breathing. Sore throat.

MAY BE ABSORBED! Dry skin. Redness. Pain. Swelling.

Redness. Pain.

Eyes, skin, respiratory system, blood, thymus, reproductive system

7-Oxabicyclo[4.1.0]heptane, 3-(2-oxiranyl)-: ACTIVE|IT HAS BEEN PROPOSED FOR USE AS CHEM INTERMEDIATE (EG, FOR CONDENSATION WITH DICARBOXYLIC ACIDS) & AS MONOMER (EG, FOR PREPN OF POLYGLYCOLS CONTAINING UNREACTED EPOXY GROUPS OR FOR HOMO-POLYMERIZATION TO 3-DIMENSIONAL RESIN).

Determination of vinyl cyclohexene dioxide using GC and IR spectroscopy.

Health Hazards -> Carcinogens