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Cyclohexane

Toxic Tips
INTRODUCTION Of the absorbed dose, only 0.5% cyclohexanol,
23.4% 1,2-cyclohexanediol and 11.3% 1,4-
Chemical Description cyclohexanediol were excreted in the urine
Cyclohexane is also named hexahydrobenzene, 72 h after exposure.7
hexamethylene, and hexanaphthen. It is
obtained in the distillation of petroleum crude
oil or by hydrogenation of benzene at 150 8C CLINICAL PRESENTATION
using Raney Nickel catalyst and at 10 atmo-
spheres H2 pressure. Cyclohexane can exist in Effects Following Inhalation
two interconvertible conformations—the boat Cyclohexane is a central nervous system depres-
and the chair.1 The Occupational Safety and sant. When inhaled, it can cause headache, nau-
Health Administration (OSHA) identifies sea, dizziness, narcosis and even death at high
cyclohexane as a benzene hexahydride.2 Cyclo- levels of exposure.2 Acute extreme exposure can
hexane is a colorless solvent with a pungent cause nausea, vomiting, incoordination, and
odor and an odor threshold of about 25 ppm. coma.8 Exposure to lower concentrations, such
Its molecular weight is 84.16; the freezing point as 250 ppm for 4 h, did not cause any observable
is 6.47 8C; the boiling point is 80.7 8C; the vapor neurobehavioral effects.3
pressure is 95 Torr at 20 8C; and its closed cup
flash point is at 8 8C. It is soluble in water, Effects Following Skin and Eye Exposure
alcohol, ether, acetone, and benzene.3 Cyclo- Cyclohexane is an irritant to the eyes and
hexane is a dangerous fire hazard; its flamm- mucous membranes. Chronic exposure to the
ability limits are between 1.3% and 8.4% by skin can cause dry, scaly, and fissured derma-
volume in air, and its auto ignition temperature titis.2 Cyclohexane vapor at or above 300 ppm
is at 245 8C.2 Its identification numbers include is irritating to the skin and eyes.5
the Chemical Abstracts Service (CAS) Registry
number (110-82-7), the OSHA IMIS code num- Carcinogenicity
ber (0810), and NIOSH Registry of Toxic Effects Cyclohexane has not been thoroughly tested
(RTECS) number (GU6300000).4 for its ability to cause cancer.9 However, it has
been found to be a weak promoter of skin
Uses and Typical Exposure Situations tumors caused by carcinogenic polycyclic aro-
Cyclohexane is mainly used as a solvent to matic hydrocarbons in a mouse skin bioas-
dissolve substances such as cellulose ethers, say.10 Be that as it may, sufficient data is not
lacquers, resins, fats, waxes, oils, bitumen, available to assign a carcinogenicity notation.3
and crude rubber. It is also used in the perfume
industry and in the production of nylon, paint,
and varnish remover. It is involved in the FIRST AID
synthesis of benzene, cyclohexanol, and cyclo-
hexanone. It is an important factor in manu- If a worker has become incapacitated due to
facturing of leather, where it has replaced the inhalation of cyclohexane, the victim should be
more toxic benzene.3 The general population removed from further exposure and medical
may be exposed to cyclohexane due to it being care obtained. If splashed in the eyes, cyclo-
present in gasoline.5 hexane should be immediately flushed from the
eyes with water and medical evaluation
obtained. Skin contact requires removing the
METABOLISM AND PHARMACOKINETICS contaminated clothing followed by washing
the skin with soap and water.2
Absorption by inhalation and urinary excretion
of cyclohexane were studied in eight workers in
a shoe factory, where cyclohexane was used as HANDLING AND STORAGE
a glue solvent. A total of 23% of the respiratory
dose and 34% of the alveolar dose were Accidental Release Measures
absorbed in the pulmonary blood. Urinary After a spill or leak, all workers should be
metabolites included cyclohexanol and cyclo- notified, and the sources of heat or ignition
hexanone, which did not exceed 0.5–1% of the removed. Stopping a leak while ventilating
absorbed dose.6 In another study, volunteers should be considered. Water spray may be used
were exposed to 300 ppm cyclohexane for 8 h. to reduce the vapors. All the spilled or leaked

1871-5532/$36.00 ß Division of Chemical Health and Safety of the American Chemical Society 33
doi:10.1016/j.jchas.2010.03.009 Elsevier Inc. All rights reserved.
cyclohexane should be absorbed in ver- tion of airborne cyclohexane concen- Safety and Health Guidelines for Cy-
miculite, dry sand, or earth, and placed tration is accomplished by using a solid clohexane, accessed from http://
into sealed containers for appropriate sorbent (charcoal) tube. Samples are www.osha.gov/SLTC/healthguide-
lines/cyclohexane/recognition.html on
disposal. If the accidental release collected at a maximum flow rate of
September 13, 2009.
involves a fire, use dry chemical, carbon 0.2 L/min until a maximum collection
3. American Conference of Governmen-
dioxide, alcohol-resistant foam or other volume of 5 L is reached. The sample is tal Industrial Hygienists (ACGIH).
foam-extinguishing agents, to fight the desorbed with carbon disulfide. The Documentation of the Threshold Limit
fire. In case of fire, an isolation distance analysis is conducted by gas chroma- Values for Chemical Substances, 7th
of a half-mile should be taken.9 tography using a flame-ionizing detec- ed.; Documentation for Cyclohexane,
tor (GC/FID).11 ACGIH, Cincinnati, OH, 2002.
Reactivities and Incompatibilities 4. Occupational Safety and Health Ad-
Exposure Guidelines ministration (OSHA). Chemical Sam-
The proper handling and storage of
The American Conference of Govern- pling Information for Cyclohexane,
cyclohexane are essential because
mental Industrial Hygienists (ACGIH) accessed from http://www.osha.gov/
cyclohexane reacts explosively with
has a Threshold Limit Value-Time dts/chemicalsampling/data/
nitrates, nitrogen dioxide, and dinitro- CH_230600.html#monitoring on Sep-
gen tetraoxide. It is not compatible Weighted Average (TLV-TWA) of
tember 13, 2009.
with oxidizing agents such as perchlo- 100 ppm for cyclohexane to prevent
5. National Library of Medicine. Hazar-
rates, peroxides, permanganates, chlo- central nervous system (CNS) impair- dous Substances Data Bank (HSDB).
rates, nitrates, chlorine, bromine, and ment.12 The OSHA Permissible Expo- Fact Sheet for Cyclohexane, accessed
fluorine. In addition, explosion-proof sure Limit (PEL) for cyclohexane is from http://toxnet.nlm.nih.gov/cgi-
electrical equipment and fittings 300 ppm (1050 mg/M3) as an 8-h time bin/sis/search/r?dbs+hsdb:@term+
should be used in areas where cyclo- weighted average (TWA) concentra- @rn+110-82-7 on September 13, 2009.
tion. NIOSH has established the 6. Mutti, A. S.; Lucertini, M.; Falzoi, M.;
hexane is handled.9
Recommended Exposure Limit et al. Organic solvents and chronic
(REL) of 300 ppm for cyclohexane as glomerulonephritis: a cross-sectional
Storage Guidelines study with negative findings for alipha-
Cyclohexane containers must be kept a TWA for up to a 10-h workday and a
tic and alicyclic C5–C7 hydrocarbons. J.
away from sources of ignition, such as 40-h work week.2 The NIOSH Imme-
Appl. Toxicol. 1981, 1(4), 224–226.
smoking and open flames. In addition, diately Dangerous to Life or Health 7. Mraz, J.; Galova, E.; Nohova, H.;
metal containers involved in the trans- Concentration (IDLH) is 1300 ppm.4 Vitkova, D. Markers of exposure to
fer of cyclohexane should be cyclohexanone, cyclohexane, and cy-
grounded.9 Cyclohexane should be clohexanol: 1,2 and 1,4-cyclohexane-
PERSONAL PROTECTION diol. Clin. Chem. 1994, 40, 1466–1468.
stored in a cool, dry, well-ventilated
8. Hathaway, G. J.; Proctor, N. H.;
area in tightly sealed containers away Personal protective equipment (PPE) Hughes, J. P.; Fischman, M. L. Proctor
from oxidizing agents.2 is based on the duration and concen- and Hughes’ Chemical Hazards of the
tration to which a worker is exposed to Workplace, 3rd ed. Van Nostrand Re-
cyclohexane. Any chemical-resistant inhold; New York, NY, 1991.
EXPOSURE CONTROLS clothing should be periodically evalu- 9. New Jersey Department of Health and
ated for its efficacy to prevent dermal Senior Services. Hazardous Substance
Control Methods Fact Sheet for Cyclohexane, accessed
contact. Safety showers and eye wash
Four methods can be used to prevent from http://nj.gov/health/eoh/rtkweb/
stations should be located close to
documents/fs/0565.pdf on September
or reduce the exposure of workers to operations involving cyclohexane. 13, 2009.
cyclohexane: process enclosure, local Workers should wear splash-proof 10. Gupta, K. P.; Mehrotra, N. K. Mouse
exhaust ventilation, general dilution chemical safety goggles. Workers skin ornithine decarboxylase induction
ventilation, and personal protective may also wear protective outer apparel and tumor promotion by cyclohexane.
equipment. Furthermore, the health such as aprons or encapsulating suits Cancer Lett. 1990, 15, 227–233.
care professional can consider the made of nitrile rubber.2 11. National Institute for Occupational
probable frequency, intensity, and Safety and Health (NIOSH). Manual
duration of exposure as well as the of Analytical Methods (NMAM)—
applicable medical condition of the REFERENCES Method 1500 for Hydrocarbons (Cyclo-
worker. Monitoring the urinary quan- 1. O’Neil, M. J., Heckelman, P. E., Koch, hexane), accessed from http://
C. B., & Roman, K. J. (Eds.). (2006). www.cdc.gov/niosh/nmam/method-
tity of cyclohexanol can be used as a
The Merck Index—An Encyclopedia of c.html on September 19, 2009.
biological method of evaluating the
Chemicals, Drugs, and Biologicals, 12. American Conference of Governmental
exposure to cyclohexane.2 Industrial Hygienists (ACGIH). 2009
Fourteenth Edition; Merck Research
Laboratories. Division of Merck & TLVs and BEIs Based on Documenta-
Sampling and Analysis Co., Inc.: Whitehouse Station, NJ, tion of the Threshold Limit Values for
As specified by National Institute for 2006, p. 456. Chemical Substances and Physical
Occupational Safety and Health 2. Occupational Safety and Health Ad- Agents & Biological Exposure Indices.
(NIOSH) Method 1500, determina- ministration (OSHA). Occupational ACGIH, Cincinnati, OH, 2009.

34 Journal of Chemical Health & Safety, May/June 2010