| Identification | More | [Name]
Cyclohexanol | [CAS]
108-93-0 | [Synonyms]
CYCLOHEXANOL
CYCLOHEXYL ALCOHOL
HEXAHYDROPHENOL
HEXALIN
HYDROXYCYCLOHEXANE
1-Cyclohexanol
Adronal
Adronol
Anol
Cicloesanolo
Cyclohexane, hydroxy-
Cykloheksanol
cykloheksanol(polish)
hexahydro-pheno
Hydralin
Hydrophenol
Naxol
Phenol, hexahydro-
CYCLOHEXANOL, REAGENTPLUS, 99%
CYCLOHEXANOL REAGENTPLUS(TM) 99% | [EINECS(EC#)]
203-630-6 | [Molecular Formula]
C6H12O | [MDL Number]
MFCD00003855 | [Molecular Weight]
100.16 | [MOL File]
108-93-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Cyclohexanol is a sticky solid (above 25℃
/77℃
F)
or colorless, viscous liquid. Faint camphor odor. | [Melting point ]
20-22 °C (lit.) | [Boiling point ]
160-161 °C (lit.) | [density ]
0.948 g/mL at 25 °C(lit.) | [vapor density ]
3.5 (vs air)
| [vapor pressure ]
0.98 mm Hg ( 25 °C)
| [refractive index ]
n20/D 1.465(lit.)
| [Fp ]
67 °C
| [storage temp. ]
Store at RT. | [solubility ]
40g/l | [form ]
Liquid After Melting | [pka]
16 | [color ]
Clear colorless | [Odor]
Like camphor. | [PH]
6.5 (40g/l, H2O, 20℃) | [Relative polarity]
0.509 | [Stability:]
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. | [explosive limit]
2-11.2%(V) | [Odor Type]
camphoreous | [Water Solubility ]
3.6 g/100 mL (20 ºC) | [Sensitive ]
Hygroscopic | [Merck ]
14,2725 | [BRN ]
906744 | [Henry's Law Constant]
16.9 at 50.00 °C, 34.4 at 60.00 °C (headspace-GC, Hovorka et al., 2002) | [Dielectric constant]
15.0（25℃） | [Exposure limits]
TLV-TWA 200 mg/m3 (50 ppm) (ACGIH);
IDLH 3500 ppm (NIOSH). | [LogP]
1.25 at 25℃ | [CAS DataBase Reference]
108-93-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Cyclohexanol(108-93-0) | [EPA Substance Registry System]
108-93-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/22:Harmful by inhalation and if swallowed .
R37/38:Irritating to respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
1
| [RTECS ]
GV7875000
| [F ]
21 | [Autoignition Temperature]
572 °F | [TSCA ]
Yes | [HS Code ]
2906 12 00 | [Hazardous Substances Data]
108-93-0(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 2.06 g/kg (Smyth) | [IDLA]
400 ppm |
| Hazard Information | Back Directory | [General Description]
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. | [Reactivity Profile]
CYCLOHEXANOL(108-93-0) 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.). | [Air & Water Reactions]
Less dense than water and slightly soluble in water. | [Hazard]
Toxic by ingestion. | [Health Hazard]
Narcosis-depression of the central nervous system tending to produce sleep or unconsciousness. | [Potential Exposure]
Cyclohexanol is used in making plac-
ticizers, dry cleaning, dyebath; and textile finishing formu-
lations; as a solvent for ethyl cellulose and other resins; it
is used in soap manufacture; it is used as a raw material for
adipic acid manufacture; as a nylon intermediate. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek Medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, includ-
ing resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a Medical
facility. When this chemical has been swallowed, get medi-
cal attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit. | [Shipping]
UN1986 Alcohols, toxic, flammable, n.o.s.,
Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poison
Inhalation Hazard, Technical Name Required. | [Incompatibilities]
Forms explosive mixture in air.
Incompatible with oxidizers (chlorates, nitrates, peroxides,
permanganates, perchlorates, chlorine, bromine, fluorine,
etc.); contact may cause fires or explosions. Keep away
from alkaline materials, strong bases, strong acids, oxoa-
cids, epoxides. Attacks some plastics. | [Description]
Cyclohexanol is a sticky solid (above 25℃/77°F) or colorless, viscous liquid with a faint camphorodor. Odor threshold=0.07 ppm. Molecularweight=100.16; Specific gravity (H2O:1)=0.96; Boilingpoint=161℃; Freezing/Melting point=24℃; Vaporpressure=mmHg at 25℃; Flash point=68℃;Autoignition temperature=300℃. The explosive limitsare: LEL=2.4%; UEL=12%. Hazard Identification (basedon NFPA-704 M Rating System): Health 1, Flammability 2,Reactivity 0. Slight solubility in water; solubility=4% at20℃. | [Chemical Properties]
colourless liquid | [Chemical Properties]
Cyclohexanol is a sticky solid (above 25℃
/77℃
F)
or colorless, viscous liquid. Faint camphor odor. | [Waste Disposal]
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinera-
tor equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed. | [Physical properties]
Clear, colorless to pale yellow, viscous, hygroscopic liquid with a camphor-like odor. A detection
odor threshold concentration of 64 μg/m3 (155 ppbv) was reported by Punter (1983). | [Occurrence]
Has apparently not been reported to occur in nature | [Uses]
Cyclohexanol is used for the productionof adipic acid and caprolactam for makingnylon. Its phthalate derivatives are used forplasticizers. It is used as a stabilizer for soapsand detergents; as a solvent for lacquers,varnishes, and shellacs; and as a dye solventfor textiles. | [Uses]
Solvent for alkyd resins, alcohol-sol phenolic resins, ethyl cellulose. manufacture of celluloid; finishing textiles; insecticides. | [Uses]
Solvent for oils, resins, ethyl cellulose;
manufacture of soap, plastics | [Definition]
ChEBI: An alcohol that consists of cyclohexane bearing a single hydroxy substituent. The parent of the class of cyclohexanols. | [Preparation]
By reduction of cyclohexanone or by hydrogenation of phenol in the presence of a catalyst (Arctander, 1969). | [Production Methods]
Cyclohexanol is prepared by the catalytic air oxidation of
cyclohexane or by the catalytic hydrogenation of phenol. The most important use of cyclohexanol is in producing
adipic acid used in the manufacture of caprolactam.
Cyclohexanol is used in the manufacture of esters for use
as plasticizers; it is also used as a chemical intermediate, a
stabilizer, a homogenizer for various soap and detergent
emulsions, and as a solvent for lacquers and varnishes .
The primary routes of occupational exposure are dermal and
inhalation. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 97, p. 7118, 1975 DOI: 10.1021/ja00857a025
Tetrahedron Letters, 21, p. 2305, 1980 DOI: 10.1016/S0040-4039(00)92591-7 | [Flammability and Explosibility]
Notclassified | [Chemical Reactivity]
Reactivity with Water: No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | [Environmental Fate]
Biological. Reported biodegradation products include cyclohexanone (Dugan, 1972;
Verschueren, 1983), 2-hydroxyhexanone, 1-oxa-2-oxocycloheptane, 6-hydroxyheptanoate, 6-
oxohexanoate, and adipate (quoted, Verschueren, 1983). In activated sludge inoculum, following a
20-d adaptation period, 96.0% COD removal was achieved. The average rate of biodegradation
was 28.0 mg COD/g?h (Pitter, 1976).
Photolytic. A photooxidation reaction rate constant of 1.74 x 10-13 cm3/molecule?sec was
estimated for the reaction of cyclohexanol with OH radicals in the atmosphere (Atkinson, 1987).
Chemical/Physical. Cyclohexanol will not hydrolyze in water because it does not contain a
hydrolyzable functional group (Kollig, 1993).
Complete combustion in air yields carbon dioxide and water vapor. | [Metabolism]
Cyclohexanol and its derivatives are generally not aromatized in vivo; large amounts of cyclohexanol may be excreted as urinary glucuronides (Williams, 1959), without prolonged retention in the organism (Browning, 1965). No urinary metabolites were detected when cyclohexanol was given to dogs by Bernhard (1937), who administered an sc dose of 0.29 g/kg, or by Weitzel (1950). Glucuronic acid was found in the urine of a dog following oral administration of cyclohexanol (Treon, 1963). Following administration to rabbits orally or by inhalation, cyclohexanol was excreted in the urine in conjugation with sulphuric and glucuronic acids. When 1-2 g cyclohexanol/kg (half the minimum lethal dose) was given orally to rabbits, 45-50% was excreted conjugated with glucuronic acid, with a decreased ratio of urinary inorganic sulphates to total sulphates. No cyclohexanone was recovered from the urine of a rabbit given 33% of the minimum lethal dose orally (Treon et al. 1943a,b). Elliott, Parke & Williams (1959) reported that more than 65% of a dose of 0-25 g cyclohexanol/kg was excreted by rabbits as glucuronides, chiefly cyclohexyl glucuronide, and an additional 6% was excreted as conjugated frarcs-cyclohexane-l,2-diol. Cyclohexanol is of interest as a metabolite of sodium cyclamate, having been identified as a metabolite in the urine of rats (Kojima & Ichibagase, 1968), rabbits (Ichibagase, Kojima, Inoue & Suenaga, 1972; Kojima & Ichibagase, 1968), guinea-pigs (Asahina, Yamaha, Sarrazin & Watanabe, 1972) and human subjects (Kojima & Ichibagase, 1969) given sodium cyclamate orally. When rabbits received 50 mg cyclohexanol as a single oral dose, the urine contained 25% of the unchanged alcohol and < 1% of the glucuronide. When rabbit-liver homogenate was incubated with cyclohexanol, 28% of the alcohol remained unchanged and 7% was metabolized. Almost no change occurred in the metabolism of cyclohexanol when the animal was pretreated with tolbutamide, which accelerates the metabolism of sodium cyclamate in the rabbit (Ichibagase et al. 1972). Cyclohexanol was not utilized to any significant extent by a number of endocrine tissues from human placenta, rat ovary, rat testis and rat adrenal gland (Ferguson, Baillie, Caiman & Hart, 1966). It was oxidized by horse-liver alcohol dehydrogenase in a preparative-scale process (Jones & Taylor, 1973) and was fermented in a process for the treatment of waste waters from caprolactam production (Kolesov, 1973). Cyclohexanol was identified as a metabolite in the urine (free and glucuronide-conjugated) in the expired air of rats receiving n-heptyl cyclohexylboronate as a single ip, iv or oral dose of 0.1 mg/kg (Caujolle, Mariotti, Oustrin & Pitet, 1970). | [storage]
Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with cyclohexanol you should be trainedon its proper handling and storage. Before entering confinedspace where this chemical may be present, check to makesure that an explosive concentration does not exist.Cyclohexanol must be stored to avoid contact with strongoxidizers (such as chlorine, bromine, and fluorine), sinceviolent reactions occur. Metal containers involving thetransfer of this chemical should be grounded and bonded.Where possible, automatically pump liquid from drums orother storage containers to process containers. Drums mustbe equipped with self-closing valves, pressure vacuum bungs,and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers of thischemical. Sources of ignition, such as smoking and openflames, are prohibited where this chemical is used, handled,or stored in a manner that could create a potential fire orexplosion hazard. Wherever this chemical is used, handled,manufactured, or stored, use explosion-proof electrical equipment and fittings. | [Purification Methods]
Reflux it with freshly ignited CaO, or dry it with Na2CO3, then fractionally distil it. Redistil it from Na. It is further purified by fractional crystallisation from the melt in dry air. Peroxides and aldehydes can be removed by prior washing with ferrous sulfate and water, followed by distillation under nitrogen from 2,4-dinitrophenylhydrazine, using a short fractionating column: water distils as the azeotrope. Dry cyclohexanol is very hygroscopic. The 3,4-dinitrobenzoate has m 111-112o (EtOH or aqueous EtOH) It has TOXIC vapours. [Beilstein 6 III 10, 6 IV 20.] |
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