Cyclohexanol
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Cyclohexanol
structure -
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CAS No:
108-93-0
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Formula:
C6H12O
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Chemical Name:
Cyclohexanol
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Synonyms:
Cyclohexanol;Adronal;Anol;Cyclohexyl alcohol;Hexahydrophenol;Hexalin;Hydroxycyclohexane;Naxol;Phenol,hexahydro-;Adronol;Hexalin (alcohol);1-Cyclohexanol;NSC 403656;NSC 54711;2263936-22-5
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CAS No:
Description
Cyclohexanol (C6H11OH), which is also known by its chemical formula C6H11OH, is a colorless, viscous liquid or can also be found in the form of a crystalline solid. This compound is characterized by its distinctive camphor-like odor. It holds significant importance in the chemical industry as it is derived from cyclohexane, which is a fundamental saturated hydrocarbon.
Cyclohexanol Basic Attributes
100.15900
100.16
203-630-6
8E7S519M3P
0243
403656
1986|1993
DTXSID4021894
Colorless needles or viscous liquid|Hygroscopic crystals|Sticky solid or colorless to light-yellow liquid (above 77 degrees F)
2906120090
Characteristics
20.23000
1.31140
Cyclohexanol appears as a colorless liquid with a camphor-like odor. Soluble in most organic liquids. Flash point 154°F. May be toxic by inhalation or skin exposure. Vapors are narcotic in high concentrations. Irritates skin, eyes and mucus membranes. Used in making soap, lacquers, and plastics.
0.9624 g/cm3 @ Temp: 20 °C
25.4 °C
161.08 °C @ Press: 760 Torr
67ºC
1.463-1.467
4%
Store at RT.
0.876mmHg at 25°C
Relative vapour density (air = 1): 3.5
Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.
vol% in air: 2.42
Camphor-like odor
4.40e-06 atm-m3/mole|Henry's Law constant = 4.40X10-6 atm-cu m/mol at 25 °C
Conversion factor: 1 ppm = 4.10 mg/cu m; 1 mg/L = 244.1 ppm|Hydroxyl radical reaction rate constant = 1.74X10-11 cu cm/molec-sec at 25 °C (est)
Less dense than water and slightly soluble in water.
Alcohols and Polyols
CYCLOHEXANOL is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. Violent reaction with nitric acid. Incompatible with strong oxidizers (chromium trioxide, nitric acid, etc.). (NTP, 1992)
Cyclohexanol|B*: Compounds that form peroxides on concentration (distillation/evaporation)|8 samples, >1- to 30 yrs, 3-2000 ppm|Management of time-sensitive chemicals (JCHAS)
572 °F (USCG, 1999)|572 °F (300 °C)|300 °C
-3.722 Mjoules/mole
10.00 eV
Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.
14.82 kcal/mol at 25 °C
Critical temperature: 650.10 K (377.1 °C); critical pressure: 4.26X10+6 Pa
Safety Information
UN 1993
1
R20/22; R37/38
S24/25
GV7875000
Xn
Separated from strong oxidants. Dry.
Stable. Incompatible with oxidizing agents. Reacts violently with oxidizing agents such as hydrogen peroxide and nitric acid, even at room temperature, to form an explosive material. Hygroscopic. Combustible.
P261
H302 + H332-H315-H335
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.
Contact with strong oxidizers causes a fire and explosion hazard. Attacks some plastics.|Ignites on contact with chromium trioxide. Violent reaction with /nitric acid/. Incompatible with oxidants.
Cyclohexanol is an indirect food additive for use only as a component of adhesives.
European Commission, ESIS; IUCLID Dataset, Cyclohexanol (108-93-0) (2000 CD-ROM edition) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.[Available from, as of May 5, 2010: http://esis.jrc.ec.europa.eu/]
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: 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 and poison 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)|Combustible. Above 68 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P321, P330, P332+P313, P362, P403+P233, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 1153 companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P332+P313, P362, P403+P233, P405, and P501|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P280, P281, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P332+P313, P403+P233, P405, and P501
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. 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)
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. 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. SMALL SPILL: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Personal protection: filter respirator for organic gases and vapors adapted to the airborne concentration of the substance.|Respirator Recommendations: Up to 400 ppm: [Table#169]|For more Personal Protective Equipment (PPE) (Complete) data for Cyclohexanol (6 total), please visit the HSDB record page.|(See protection codes)
Flammable when exposed to heat or flame.
Lower explosive limit: 2.7%% by volume; Upper explosive limit: 12% by volume|Above 68 °C explosive vapor/air mixtures may be formed.|Cyclohexanol and nitric acid can react at room temperature to form a violently explosive material. /Nitric acid plus cyclohexanol/|Explosive limits , vol% in air: 2.4-12
Use dry chemical, carbon dioxide, or alcohol foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position ... The only respirators recommended for fire fighting are self-contained breathing apparatuses that have full facepieces and are operated in a pressure-demand or other positive-pressure mode.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Spill handling: evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, or a similar material and deposit in sealed containers. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations.|Collect leaking and spilled liquid in sealable containers as far as possible. Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.|Environmental considerations - land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.|For more Cleanup Methods (Complete) data for Cyclohexanol (6 total), please visit the HSDB record page.
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 protectionequipment should be worn even when contact lenses are in place.|SRP: Contaminated protective clothing should be segregated in a manner that results in no direct personal contact by personnel who handle, dispose of, or clean the clothing. Quality assurance procedures to confirm the efficacy of the cleaning procedures should be implemented prior to the decontaminated protective clothing being returned for reuse by the workers. Contaminated clothing (including shoes/socks) should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|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.|For more Preventive Measures (Complete) data for Cyclohexanol (9 total), please visit the HSDB record page.
Severe eye irritant.|Irritation to the eyes, nose and throat of human subjects results at 100 ppm.
Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 50 ppm (200 mg/cu m).|Vacated 1989 OSHA PEL TWA 50 ppm (200 mg/cu m), skin designation, is still enforced in some states.
Recommended Exposure Limit: 10 Hour Time-Weighted Average: 50 ppm (200 mg/cu m), skin
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.
Separated from strong oxidants. Dry.
A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system.
The substance defats the skin, which may cause dryness or cracking.
NO open flames. Above 68 °C use a closed system and ventilation.
PREVENT GENERATION OF MISTS!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear safety spectacles or eye protection in combination with breathing protection.
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). 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. Cyclohexanol is produced, as an intermediate or final product, by process units covered under this subpart.
| 1 - Materials that, under emergency conditions, can cause significant irritation.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.
Cyclohexanol was qualitatively detected in 5 of 16 samples derived from large volume (>400 gallons) samples of advanced treatment concentrate from 4 of 6 cities (Lake Tahoe, CA, Oct 1974; Orange County, CA, Feb 1976; Dallas, TX, Nov 1974; Blue Plains, Washington, DC, May 1975)(1). Cyclohexanol was found at concentrations ranging from 0.24 to 1.2 mg/L in trench leachate from low level radioactive waste sites at Maxey Flats, KY and West Valley, NY(2,3). It has been found at concentrations >0.5 ppm in wastewaters from unspecified industries in the organic chemicals and plastics/synthetic fibers industrial categories(4). A concentration of 1 ppb was found in samples of leachate or samples of groundwater plume taken at an unspecified municipal landfill at an unspecified time(5). The cyclohexanol concentration found in wastewater from a Russian caprolactam manufacturing facility was reported to be 3.5 mg/L(6). Cyclohexanol was detected in the distillate of landfill leachate of Japanese municipal waste at a concentration of 112 ug/L(7).
URBAN/SUBURBAN: Cyclohexanol was qualitatively detected in ambient air samples taken from an unspecified site in the Los Angeles Basin between 1974 and 1975(1).
Cyclohexanol was detected in recently manufactured 100% nylon carpeting with polypropylene backing and styrene-butadiene rubber (SBR) adhesive. A residence time of 28.8 minutes was observed in screening studies measuring VOC concentration in headspace of the storage bags(1). In a study testing VOC emissions from commercially available lacquers and foils for furniture coatings, cyclohexanol was detected 2 times out of 44 samples analyzed in gas chamber tests(2). Cyclohexanol was detected in 1 out of 10 emission samples of PVC cushion vinyls for flooring materials at average concentrations of 16 ug/sq m-hr for a 3 day old sample and 9 ug/sq m-hr for a 28 day old sample(3).
Toxicity
... This study explored the acute effect of ethanol (EtOH) on the urinary excretion of cyclohexanol (CH-ol), 1,2- and 1,4-cyclohexanediol (CH-diol), biomarkers of exposure to important solvents, and chemical intermediates cyclohexanone (CH-one), cyclohexane (CH) and cyclohexanol. ... Volunteers (5-8 in each group) were exposed for 8 hours either to CH-one, CH or CH-ol vapor at concentrations of about 200, 1000, and (SRP: 2000) mg/cu m, respectively, with concomitant ingestion of EtOH (4 14-g doses taken during the exposure). Urine was collected for 72 hours and analyzed for CH-ol and CH-diols ... . RESULTS: The metabolic yields of CH-ol, 1,2-, and 1,4-CH-diol, respectively, in the exposures with EtOH were as follows: 11.3%, 36%, 23% after the exposure to CH-one, 3.1%, 15%, 8% after the exposure to CH, and 6.6%, 24%, 18% after the exposure to CH-ol. [The corresponding values obtained previously in matching experiments without EtOH were as follows: 1.0%, 39%, 18% (CH-one); 0.5%, 23%, 11% (CH); and 1.1%, 19%, 8% (CH-ol).] The excretion curves of the metabolites in the exposures with EtOH were not delayed when compared with the corresponding curves of a comparison group. CONCLUSIONS: The urinary excretion of CH-diols is much less sensitive to EtOH than that of CH-ol. It is recommended to employ CH-diols as useful and more reliable biomarkers of exposure to CH-one, CH and CH-ol in field examinations.
LD50 Rat oral 2060 mg/kg|LD50 Rat oral (gavage) 1550 mg/kg|LD50 Mouse ip 1352 mg/kg|LD50 Mouse sc 2480 mg/kg|For more Non-Human Toxicity Values (Complete) data for Cyclohexanol (8 total), please visit the HSDB record page.
Cyclohexanol's production and use in the synthesis of adipic acid, caprolactam (with cyclohexanone); as a stabilizer and homogenizer for soaps and synthetic detergent emulsions; as a solvent for lacquers, varnishes(1), oils, and shellacs(2), phenolic insecticides, for alkyd and phenolic resins, cellulosics; as a blending agent for lacquers, paints and varnishes; in finish removers, leather degreasing, polishing, plasticizers, plastics, and germicides(3) 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 11(SRC), determined from a log Kow of 1.23(2) and a regression-derived equation(3), indicates that cyclohexanol is expected to have very high mobility in soil(SRC). Volatilization of cyclohexanol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 4.40X10-6 atm-cu m/mole(4). Cyclohexanol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.657 mm Hg at 25 °C(5). In the Japanese MITI test, a 96% of theoretical BOD using activated sludge was reached in 4 weeks(6). Various other aerobic screening studies reported 5-day degradations ranging from 57% to 96% based on theoretical BOD in acclimated sewage inoculums or mixed microbial cultures(7-9). These data suggest that biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a log Kow of 1.23(2) and a regression-derived equation(3), indicates that cyclohexanol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 4.40X10-6 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 8.4 days and 64 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3.0(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). In the Japanese MITI test, a 96% of theoretical BOD using activated sludge was reached in 4 weeks(7). Various other aerobic screening studies reported 5-day degradations ranging from 57% to 96% based on theoretical BOD in acclimated sewage inoculums or mixed microbial cultures(8-10). These data suggest that biodegradation is an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyclohexanol, which has a vapor pressure of 0.657 mm Hg at 25 °C(2), will exist solely in the vapor phase in the ambient atmosphere. Vapor-phase cyclohexanol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 22 hrs(SRC), calculated from its rate constant of 1.7X10-11 cu cm/molecule-sec at 25 °C(3). Cyclohexanol does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of cyclohexanol with photochemically-produced hydroxyl radicals has been estimated as 1.7X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 22 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Cyclohexanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Cyclohexanol does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3.0 was calculated for cyclohexanol(SRC), using a log Kow of 1.23(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
The Koc of cyclohexanol is estimated as 11(SRC), using a log Kow of 1.23(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cyclohexanol is expected to have very high mobility in soil.
The Henry's Law constant for cyclohexanol is 4.40X10-6 atm-cu m/mole(1). This Henry's Law constant indicates that cyclohexanol is expected to volatilize 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 8.4 days(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 64 days(SRC). Cyclohexanol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Cyclohexanol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.657 mm Hg(3).
GROUNDWATER: Cyclohexanol was qualitatively detected in samples of groundwater taken between 1975 and 1978 from an aquifer polluted by organic waste from western suburbs of Melbourne, Australia(1). It was detected at a maximum concentration of 1 ppb in samples of groundwater taken between 1976 and 1978 at contaminated dump sites in the Netherlands(2). It was detected at a concentration of 1 ppb in groundwater taken from a landfill site near Norman, OK(3).|DRINKING WATER: Cyclohexanol was qualitatively detected in 8 of 16 samples of drinking water concentrate derived from large volume (>400 gallons) samples from 6 of 7 cities (Cincinnati, OH, Oct 1978; Miami, FL, Feb 1976; New Orleans, LA, Jan 1976; Philadelphia, PA, Feb 1976; Ottumwa, IA, Sept 1976; Seattle, WA, Nov 1976(1).
Cyclohexanol was detected in boiled and roasted Chinese chestnuts commercially grown in western Pennsylvania in 1994(1). Cyclohexanol was detected in raw earth almond from Valencia, Spain, but was not detected after subsequent roasting(2). Cyclohexanol was qualitatively detected in mixtures of volatile flavor components from fried chicken(3) and baked potatoes (Idaho Russet Burbank potatoes)(4).
According to the 2006 TSCA Inventory Update Report, the number of persons reasonably likely to be exposed in industrial manufacturing, processing, and use of cyclohexanol is 1000 or greater; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 112,365 workers (41,412 of these were female) were potentially exposed to cyclohexanol in the US(1). Occupational exposure to cyclohexanol may occur through inhalation and dermal contact with this compound at workplaces where cyclohexanol is produced or used. Monitoring and use data indicate that the general population may be exposed to cyclohexanol via inhalation of ambient or indoor air, ingestion of food and drinking water, and dermal contact with this compound or other consumer products containing cyclohexanol(SRC).|... Human subjects exposed ... for 3-5 min to 100 ppm ... the majority ... believed that highest permissible concn for an 8-hr exposure, from standpoint of comfort, should be less than 100 ppm. At concn of 272 ppm ... odor of cmpd was recognized at once by human subjects.
Cyclohexanol was detected in the expired air of 5 of 8 volunteer employees from the U.S. Air Force School of Aerospace Medicine, Brooks Air Force Base, Texas; the concentration averaged 0.78 ug/hr (for positive samples) and ranged between 0.28 and 1.6 ug/hr(1). It was detected in 65.6% of 387 samples of expired air taken from 54 study subjects who were carefully selected from urban areas and were normal, healthy, and non-smoking individuals; the geometric mean was 2.6 ng/L of expired air(2). In a study of 59 workers with occupational exposure to cyclohexanone, it was found that urinary cyclohexanol correlated with the time-weighted-average cyclohexanone exposure(3). When the time-weighted exposure was 25 ppm, the corresponding calculated cyclohexanol level was 54.5 mg/L.
Drug Information
The substance can be absorbed into the body by inhalation and by ingestion.|Animal expt ... In large doses ... /cyclohexanol/ is readily absorbed from the skin ... .|Following oral admin ... to rabbits, cmpd is excreted in urine in conjugation with sulfuric & glucuronic acids. Similar results were obtained when animals were subjected to repeated inhalation of cmpd.|... Rabbits exposed to lowest concn ... 145 ppm cyclohexanol in air, showed no incr in conjugation of urinary sulfates but excreted 5 times normal amt glucuronic acid.|... Incr in glucuronic acid in urine was paralleled by a decr in percentage of inorg sulfates. ... That the urinary sulfate ratio became normal when exposure ceased ... led ... to ... /conclusion/ that there was no prolonged retention in organism.
Cyclohexane was hydroxylated to cyclohexanol by rat liver microsomes in presence of NADPH & oxygen. Pretreatment with phenobarbital at 80 mg/kg/day ip stimulated activity 6-fold, while benzopyrene pretreatment at 20 mg/kg ip lowered cyclohexane hydroxylation.|Cyclohexanol was identified as the urinary metabolite after admin of cyclohexylamine hydrochloride to rats, rabbits, & guinea pigs (50-500 mg/kg, orally or ip) and humans (25 or 200 mg, orally).|Fed to rabbits, /cyclohexanol/ ... Is mostly excreted as the glucuronide conjugate (60% of the dose), but a small amt is oxidized further into trans-cyclohexane-1,2-diol (6%).|Hepatic NAD-dependent alcohol dehydrogenase ... is responsible for metabolism of ... cyclohexanol ...|For more Metabolism/Metabolites (Complete) data for Cyclohexanol (8 total), please visit the HSDB record page.
Cyclohexane, benzene, cyclohexanone, and phenol
Narcosis-depression of the central nervous system tending to produce sleep or unconsciousness. (USCG, 1999)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)|(See procedures)
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Higher alcohols (>3 carbons) and related compounds/|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 shock and treat if necessary ... . 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 ... . /Higher alcohols (>3 carbons) 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. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/
/HUMAN EXPOSURE STUDIES/ In a 48 hour closed patch test using 4% cyclohexanol in petrolatum, there was evidence of erythema or edema in human subjects.|/HUMAN EXPOSURE STUDIES/ ... Ten human subjects /were exposed/ to various concentrations of cyclohexanol for 3-5 minutes. The estimated acceptable concentration in air for 8 hours was reported by the volunteer subjects to be less than 100 ppm. No person was actually exposed to any of the test concentrations for 8 hours.|/HUMAN EXPOSURE STUDIES/ ... This study explored the acute effect of ethanol (EtOH) on the urinary excretion of cyclohexanol (CH-ol), 1,2- and 1,4-cyclohexanediol (CH-diol), biomarkers of exposure to important solvents, and chemical intermediates cyclohexanone (CH-one), cyclohexane (CH) and cyclohexanol. ... Volunteers (5-8 in each group) were exposed for 8 hours either to CH-one, CH or CH-ol vapor at concentrations of about 200, 1000, and 200 mg/cu m, respectively, with concomitant ingestion of EtOH (4 14-g doses taken during the exposure). Urine was collected for 72 hours and analyzed for CH-ol and CH-diols ... . RESULTS: The metabolic yields of CH-ol, 1,2-, and 1,4-CH-diol, respectively, in the exposures with EtOH were as follows: 11.3%, 36%, 23% after the exposure to CH-one, 3.1%, 15%, 8% after the exposure to CH, and 6.6%, 24%, 18% after the exposure to CH-ol. [The corresponding values obtained previously in matching experiments without EtOH were as follows: 1.0%, 39%, 18% (CH-one); 0.5%, 23%, 11% (CH); and 1.1%, 19%, 8% (CH-ol).] The excretion curves of the metabolites in the exposures with EtOH were not delayed when compared with the corresponding curves of a comparison group. CONCLUSIONS: The urinary excretion of CH-diols is much less sensitive to EtOH than that of CH-ol. It is recommended to employ CH-diols as useful and more reliable biomarkers of exposure to CH-one, CH and CH-ol in field examinations.|/SIGNS AND SYMPTOMS/ In a group of 174 women and 279 men who were exposed daily to less than the "permitted" concentration of cyclohexanol, 114 individuals showed nonspecific disturbances of the autonomic nervous system during a 2 year period, while only 8 out of 100 persons in a nonexposed control group had similar disturbances.|For more Human Toxicity Excerpts (Complete) data for Cyclohexanol (8 total), please visit the HSDB record page.
Cyclohexanol
The substance can be absorbed into the body by inhalation and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact
irritation eyes, skin, nose, throat; narcosis
Cough. Dizziness. Drowsiness. Headache. Nausea. Sore throat.
Dry skin. Redness.
Redness. Pain.
Eyes, skin, respiratory system
Cyclohexanol Use and Manufacturing
Cyclohexanol can be prepared in high yield by either vapor- or liquid-phase hydrogenation of phenol. Vapor-phase hydrogenation can be carried out by using a supported nickel catalyst or a nickel catalyst containing copper, cobalt, or manganese. The support is usually alumina or silicic acid. Yields as high as 98% have been reported. ... Commercial liquid-phase hydrogenation of phenol under mild conditions with a palladium on carbon catalyst gives greater than 99% yield of cyclohexanone at 90% conversion. By adjusting the operating conditions and changing to a Raney nickel catalyst, 99.9% selectivity for cyclohexanol can be achieved.|Liquid-phase oxidation of cyclohexane.|Boric acid modified oxidation of cyclohexane ... In the 1950s, Scientific Design (now Halcon International) developed a process in which anhydrous metaboric acid was added as a slurry to the first of several staged air oxidation vessels. The cyclohexyl hydroperoxide formed is trapped as the cyclohexyl perborate ester. The perborate ester then reacts with additional cyclohexane in the air oxidizer to yield the borate ester and additional cyclohexanol. This borate ester is relatively stable in the air oxidizer and is protected from over oxidation to ring-opened products. The ester is subsequently hydrolyzed to cyclohexanol and boric acid. The boric acid is dehydrated to metaboric acid and is recycled to the air oxidizer.|Production and hydration of cyclohexene ... The process involves three primary steps: the selective hydrogenation of benzene; the separation of the cyclohexene from the unconverted benzene and the over-hydrogenation product cyclohexane; and the hydration of the cyclohexene. The yield of this process from benzene to cyclohexanol is extremely high, probably greater than 95%.|For more Methods of Manufacturing (Complete) data for Cyclohexanol (7 total), please visit the HSDB record page.
Cyclohexanol is the organic compound with the formula (CH2)5CHOH. The molecule is related to cyclohexane ring by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Billions of kilograms are produced annually, mainly as a precursor to nylon.
750,000,000 - 1,000,000,000 lb|(1972) 3.87X10+11 GRAMS|(1975) PROBABLY GREATER THAN 1.36X10+6 GRAMS|(1992) Not reported|Cyclohexanol is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|For more U.S. Production (Complete) data for Cyclohexanol (6 total), please visit the HSDB record page.
90% FOR ADIPIC ACID FOR NYLON; 10% FOR MISC APPLICATIONS INCLUDING SYNTHESIS OF ADIPIC ACID FOR NON-NYLON APPLICATIONS, SYNTHESIS OF CYCLOHEXYL ESTERS (INCL DICYCLOHEXYL PHTHALATE), AND AS STABILIZER AND DYE SOLVENT IN THE TEXTILE INDUSTRY (1972).|(1985) 95% FOR ADIPIC ACID
Grade: Technical (contains freezing inhibitor)|Commercial products: Technical and High-grade|SOME CYCLOHEXANOL IS SHIPPED WITH 2.25% METHANOL AS ANTIFREEZE.|KA OIL USED FOR ADIPIC ACID PRODUCTION IS 65% CYCLOHEXANOL
All other basic organic chemical manufacturing|Cyclohexanol: ACTIVE|Was prepared by the treatment of 4-iodocyclohexanol with zinc dust in glacial acetic acid.
Method: NIOSH 1402, Issue 2; Procedure: gas chromatography with flame ionization detector; Analyte: cyclohexanol; Matrix: air; Detection Limit: 0.01 mg/sample.|Method: NIOSH 1405, Issue 1; Procedure: gas chromatography with flame ionization detector; Analyte: cyclohexanol; Matrix: air; Detection Limit: 1 ug/sample.|Method: OSHA 7; Procedure: gas chromatography with flame ionization detector; Analyte: cyclohexanol; Matrix: air; Detection Limit: not provided.|A TIME-SAVING GAS CHROMATOGRAPHIC METHOD FOR DETERMINING CYCLOHEXANOL IN AIR IS PRESENTED.|For more Analytic Laboratory Methods (Complete) data for Cyclohexanol (6 total), please visit the HSDB record page.
A simple and sensitive method for determining urinary cyclohexanol, the main metabolite of cyclohexanone, by hydrolysis and gas chromatography (GC) with a flame ionization detector was developed. ... The procedure is relatively simple and reproducible and it can be applied for occupational health measurement of cyclohexanone exposure.|COLORIMETRIC DETERMINATION OF CYCLOHEXANOL IN RAT URINE WITH ACCURACY OF + or - 7.8%.|A METHOD OF DETERMINING CYCLOHEXANOL IN RAT URINE BY GAS CHROMATOGRAPHY IS PRESENTED.
Food additives -> Flavoring Agents|Fire Hazards -> Flammable - 2nd degree|Insecticides
Flavoring Agents
Computed Properties
Molecular Weight:100.16
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:100.088815002
Monoisotopic Mass:100.088815002
Topological Polar Surface Area:20.2
Heavy Atom Count:7
Complexity:46.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
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