Cyclohexane

HCID 8078CAS 110-82-7

Basic information

Standard SMILES
C1CCCCC1
InChIKey
XDTMQSROBMDMFD-UHFFFAOYSA-N
Molecular formula
C6H12
Average molar mass
84.16 g/mol
Monoisotopic mass
84.09390038

Overview

Cyclohexane appears as a clear colorless liquid with a petroleum-like odor. Used to make nylon, as a solvent, paint remover, and to make other chemicals. Flash point -4 °F. Density 6.5 lb / gal (less than water) and insoluble in water. Vapors heavier than air.

Names & identifiers

Preferred name
Cyclohexane
IUPAC
cyclohexane
English name
Cyclohexane
Molecular formula
C6H12
Molecular weight
84.16

Names & synonyms

CYCLOHEXANE110-82-7HexamethyleneHexahydrobenzeneHexanaphtheneCyclohexanCykloheksanBenzene, hexahydro-CicloesanoCyclohexaanBenzenehexahydrideRCRA waste number U056
Show more names
NAPHTHENEohexanehexamethylenCYCLOHEXANE-205Cyclohexane, pure
Caswell No. 269CCRIS 3928DTXSID4021923EPA Pesticide Chemical Code 025901NSC-40683548K5MKG32SAI3-08222DTXCID701923

Database identifiers

CAS
110-82-7、12217-02-6
PubChem CID
8078
DTXSID
DTXSID4021923
ChEMBL
CHEMBL15980
ChEBI
CHEBI:29005
UNII
48K5MKG32S
EC Number
203-806-2、601-849-5
Nikkaji
J2.882G

Properties

Computed structural properties

XLogP
3.4
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Aliphatics, Saturated (<C12)
CosmeticsSolvent
SpringerMaterials PropertiesCoriolis coupling
PesticidesPesticide -> EPA IRIS
LogP · 3 items

log Kow = 3.44

3.44

3.4

Physicochemical properties

Melting point
4 · 4-7 °C (lit.)
Boiling point
80.7 °C · 80.7 °C (lit.)
Density
0.779 g/mL · 0.779 g/mL at 25 °C (lit.)
vapor density
2.9 · 2.9 (vs air)
vapor pressure
168.8 mm · 168.8 mm Hg ( 37.7 °C)
refractive index
20 · n20/D 1.426(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P319, P321, P331, P332+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 4880) of reports.

Danger

H225 (> 99.9%): Highly Flammable liquid and vapor [Danger Flammable liquids]

Hazard information

Regulatory Information · 6 items

Chemical: Cyclohexane

Regulation (EC) No 178/2002 (amended)

Cyclohexane is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexane are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15483

Restricted substance: Cyclohexane

Cyclohexane: HSNO Approval: HSR001111 Approved with controls

Other Safety InformationIMAP assessments - Cyclohexane: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 items

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Vapour/air mixtures are explosive. Heating will cause rise in pressure with risk of bursting.

Fire PotentialDangerous fire hazard when exposed to heat or flame; can react with oxidizing materials.
Health Hazards · 2 items

Dizziness, with nausea and vomiting. Concentrated vapor may cause unconsciousness and collapse. (USCG, 1999)

CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Use water spray, foam, powder, carbon dioxide. Water may be ineffective. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 items

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.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Provision to contain effluent from fire extinguishing. Separated from strong oxidants. Store in an area without drain or sewer access.
Exposure Control and Personal Protection · 3 items

· Wear positive pressure self-contained breathing apparatus (SCBA).

Biological Exposure Indices (BEI) [ACGIH] - 50 mg/g creatinine at end of shift, end of workweek (1,2-cyclohexanediol in urine); [ACGIH TLVs and BEIs]

200.0 [ppm]

Toxicology

Body Burden · 2 items

Five of eight samples of mother's milk collected from 4 urban/industrial areas in the United States were positive for cyclohexane(1). A population of 54 normal, healthy, nonsmoking subjects from urban environment (387 samples) had a 64.6% occurrence of cyclohexane in expired air with a geometric mean concentration of 5.0 ng/L(2). In a heterogenous, nonsmoking population of 62 subjects, cyclohexane was a common constitutent in the expired air of control, diabetic, and prediabetic subjects(3).

Cyclohexane was qualitatively found in 8 of 12 breath samples of subjects monitored in Bayonne and Elizabeth, NJ, and Research Triangle Park, NC, 1980(1). Cyclohexane was detected in 30 of 56 personal air samplers for outside attendants at gasoline stations at a mean concentration of 0.114 mg/cu m, 45 of 49 samples for transport drivers at a mean concentration of 0.739 mg/cu m, and 43 of 49 samples for service attendants at a mean concentration of 0.127 mg/cu m(2). The indoor air inhaled dose of cyclohexane for residents in 3 Italian cities, March, 1995, was 28.5, 22.5. and 28.0 ug/day(3).

TreatmentTreatment is mainly symptomatic and supportive. Gastric lavage, emesis, and the administration of activated charcoal should be avoided, as vomiting increases the risk of aspiration. (A600)
Interactions · 2 items

Female mice inhaled 2x10-4 mol/L cyclohexane for 0.5-3 days. No change was noted after 0.5 days in hexobarbital (i) sleeping time or its half-life in plasma. After 1 day there was a decrease by 50 and 60% respectively. A steady state in inactivation was noted during the main increase in dealkylase, reductase, and cytochrome.

Mice (33 males) received one 60 ul application of 0.3% DMBA in benzene followed by a 60 uL/ application of cyclohexane twice/week for 50 weeks. No promoting activity of cyclohexane was observed.

Target Organs · 2 items

Developmental

Eyes, skin, respiratory system, central nervous system

Health EffectsPetroleum distillates are aspiration hazards and may cause pulmonary damage, central nervous system depression, and cardiac effects such as cardiac arrhythmias. They may also affect the blood, immune system, liver, and kidney. (A600, L1297)
Ecotoxicity Values · 5 items

LC50; Species: Crangon franciscorum (Bay Shrimp) weight 1.7 g, length 6.4 cm; Conditions: saltwater, static; Concentration: 3400 ug/L for 24 hr />99% purity/

LC50; Species: Crangon franciscorum (Bay Shrimp) weight 1.7 g, length 6.4 cm; Conditions: saltwater, static; Concentration: 2400 ug/L for 96 hr (95% confidence interval: 1700-3500 ug/L) />99% purity/

EC50; Species: Daphnia magna (Water flea) age 4-6 days, length 1.5 mm; Conditions: freshwater, static, 23 °C, pH 6-7, dissolved oxygen 5-9 mg/L; Concentration: 45 mmol/cu m for 48 hr (95% confidence interval: 34-60 mmol/cu m); Effect: intoxication, immobilization /> or =97% purity/

LC50; Species: Daphnia magna (Water flea) age < or =24 hr; Conditions: freshwater, static, 20-22 °C, pH 7.6-7.7; Concentration: 340000 ug/L for 24 hr /formulation/

For more Ecotoxicity Values (Complete) data for CYCLOHEXANE (20 total), please visit the HSDB record page.

Regulatory information

FDA Requirements · 2 items

Cyclohexane may be used in inks for marking food supplements in tablet form, gum, and confectionery. Restrictions: no residue.

Cyclohexane is an indirect food additive for use only as a component of adhesives.

RCRA Requirements · 1 item

U056; As stipulated in 40 CFR 261.33, when cyclohexane, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Cyclohexane is included on this list. Effective date: 12/19/85; Sunset date: 12/19/95.

FIFRA Requirements · 1 item

Residues of cyclohexane are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: solvent, cosolvent.

Atmospheric Standards · 1 item

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. Cyclohexane is produced, as an intermediate or a final product, by process units covered under this subpart.

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Safety data

F
3-10
OEB
A
OEL
TWA: 300 ppm (1050 mg/m3)
wgk
2
IDLA
1,300 ppm [10% LEL]
tsca
TSCA listed

Chemistry & industry

Pharmacology

Biological Half-Life · 1 item

This article reports the results obtained with the biological and environmental monitoring of occupational exposure to cyclohexane using 1,2-cyclohexanediol (1,2-DIOL) and 1,4-DIOL in urine. The kinetic profile of 1,2-DIOL in urine suggested by a physiologically based pharmacokinetic (PBPK) model was compared with the results obtained in workers. ...Both metabolites have a urinary half-life of close to 18 hr and accumulate during the working week. Comparison between data obtained from a PBPK model and those found in workers suggests that 1,2-DIOL and 1,4-DIOL are urinary metabolites suitable for the biological monitoring of industrial exposure to cyclohexane.

Metabolism/Metabolites · 6 items

Four known or suspected metabolites of cyclohexane (cyclohexanol, cyclohexanone, 1,4-cyclohexanediol and 1,4-cyclohexanedione) were also studied for kidney effects. These compounds were administered at a daily dose of 0.5 g/kg (5 I.P. injections per week for two weeks). Only cyclohexanol increased beta-2-microglobulin which suggests that this metabolite is responsible for the kidney effects of cyclohexane.

The disposition and metabolism of cyclohexane have been investigated in three species; rat, rabbit and man. The available data indicate that cyclohexane can be absorbed via the oral and inhalation routes but no adequate data exist via the dermal route. There is no clear evidence of bioretention in the tissue examined. No cyclohexane was found in the brain of rats exposed to cyclohexane for 2 weeks. Cyclohexane is known to undergo oxidative metabolism to yield cyclohexanol (major metabolite), cyclohexanone, and possibly other oxidative products (1,2- or 1,4-dihydroxycyclohexane and its corresponding ketone analogs). The alcohol products can form phase 2 conjugates (sulfates and glucuronide).

The metabolism and toxicokinetics of cyclohexane (CH) and cyclohexanol (CH-ol), important solvents and chemical intermediates, were studied in volunteers after 8-hr periods of inhalation exposure at concentrations of 1010 and 236 mg/cu m, respectively (occupational exposure limits: CH, 1050 mg/cu m; CH-ol, 200 mg/cu m)). Of the dose of absorbed parent compounds, the yields of urinary CH-ol and 1,2- and 1,4-cyclohexanediol (CH-diol) were 0.5%, 23.4%, and 11.3%, respectively, after exposure to CH and 1.1%, 19.1%, and 8.4%, respectively, after exposure to CH-ol as determined by a gas chromatography method involving hydrolysis of glucuronide conjugates. The metabolic patterns of CH and CH-ol were very similar to that of cyclohexanone (CH-one) studied in the laboratory previously. For all three compounds, peak excretion of CH-ol occurred at the end of the exposure period, after which it decayed rapidly. Excretion curves of 1,2- and 1,4-CH-diol reached maximal values within 0-6 hr postexposure, with subsequent elimination half-lives being 14-18 hr. The rate-limiting step in the elimination of CH compounds from the organism is renal clearance of CH-diols...

These compounds /including cyclohexane/ ... are metabolized mostly into cyclohexanol glucuronide.

For more Metabolism/Metabolites (Complete) data for CYCLOHEXANE (8 total), please visit the HSDB record page.

Volatile hydrocarbons are absorbed mainly through the lungs, and may also enter the body after ingestion via aspiration. (A600)

Absorption, Distribution and Excretion · 5 items

Studies from the exposure of the general population to cyclohexane revealed that human milk from five of eight mothers contained cyclohexane (concentrations not determined). /It was/ suggested that the cyclohexane in the milk resulted from the mothers' exposure to environmental pollutants since they resided near chemical manufacturing plants or industrial user facilities.

...Measures of brain metabolism, RNA, glutathione, and glutathione peroxidase activity were not affected by cyclohexane exposure. However, the cyclohexane dose increased, brain azoreductase activity decreased significantly and was still well below control levels after a recovery period. Activation of the mixed-function oxidase system has been found to inhibit azo reduction. /The results suggest/ that although increased blood circulation in the brain compared to fatty tissue enhances cyclohexane elimination from the brain, the activation of a liver mixed-function oxidase system is the primary vehicle for decreasing the cyclohexane concentration in the body as a whole.

Seventy-two hours after a single intravenous dose of 10 mg/kg [(14)C]cyclohexane or a single oral dose of 200 mg/kg to adult male Fischer 344 rats, the concentration of radioactivity in adipose was 16 times greater than that in blood. At higher oral doses (1,000 or 2,000 mg/kg), the adipose tissue-to-blood ratio of radioactivity approximately 45. Although radioactivity in adipose tissues was primarily cyclohexane (79-84%), in muscle, liver and skin, only 2-18% of the (14)C was identified as cyclohexane. Cyclohexane, cyclohexanol, and cyclohexanone were present in all tissues...

There are two major pathways in the elimination of cyclohexane: (1) cyclohexane (unmetabolized) is present in expired air, and (2) oxidative products e.g., cyclohexanol as free or bound, are present in the urine. Biomonitoring of cyclohexane exposure include the measurement of cyclohexane in alveolar air specimens or cyclohexanol (free or bound) in the urine.

For more Absorption, Distribution and Excretion (Complete) data for CYCLOHEXANE (6 total), please visit the HSDB record page.

Cellular LocationsMembrane

Uses & manufacturing

Uses · 6 items

Used in the production of nylon and as a paint and varnish remover; Also used as a solvent (lacquers, resins, and glues, e.g., in leather manufacturing) and intermediate for organic synthesis; [ACGIH]

Painting (Solvents) [Category: Paint]

For cyclohexane (USEPA/OPP Pesticide Code: 025901) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Organic solvent for lacquers and resins. Paint and varnish remover. In the extraction of essential oils. In analytical chemistry for molecular weight determinations (cryoscopic constant 20.3). In the manufacturing of adipic acid, benzene, cyclohexyl chloride, nitrocyclohexane, cyclohexanol and cyclohexanone. In the manufacturing of solid fuel for camp stoves. In fungicidal formulations (possesses slight fungicidal action). In the industrial recrystallization of steroids.

Manufacture of nylon; solvent for cellulose ethers, fats, oils, waxes, bitumens, resins, crude rubber; extraction essential oils; organic synthesis; paint and varnish removers; glass substitutes.

Over 98% of the cyclohexane produced is used to make nylon intermediates: adipic acid (60%), caprolactam, and hexamethylenediamine 75% of the caprolactam produced worldwide is used for nylon 6 manufacture. Minor miscellaneous uses, such as solvents and polymer reaction diluents, consume the remainder of the cyclohexane produced.

Impurities · 1 item

Impurities are unconverted benzene, aliphatic hydrocarbons in the benzene feed to the hydrogenation unit, methylcyclopentane formed by isomerization of cyclohexane, and methylcyclohexane formed by hydrogenation of the small amount of toluene in benzene.

U.S. Exports · 3 items

(1972) 2.35X10+11 grams

(1975) Negligible

(1984) 6.04X10+10 g

U.S. Imports · 3 items

(1972) Negligible

(1975) 1.28X10+11 grams

(1983) 8.63X10+9 g

U.S. Production · 6 items

2023: 1,000,000,000 - <2,500,000,000 lb

(1972) 1.04X10+12 grams

(1975) 6.51X10+11 grams

(1984) 9.03X10+11g

(1990) 2.46 billion lb

For more U.S. Production (Complete) data for CYCLOHEXANE (11 total), please visit the HSDB record page.

Consumption Patterns · 5 items

52% For adipic acid; 21% exported; 19% for caprolactam; 4% for 1,6-hexamethylenediamine; 4% for misc applications (1971)

65% For adipic acid; 32% for caprolactam; 3% for misc (1984 est)

CHEMICAL PROFILE: Cyclohexane. Adipic acid for nylon 66, 57%; caprolactam for nylon 6, 29%; exports, 13%; other, 1%.

CHEMICAL PROFILE: Cyclohexane. Demand: 1985: 234 million gallons; 1986: 279 million gallons; 1990 /projected/: 308 million gallons.

For more Consumption Patterns (Complete) data for CYCLOHEXANE (7 total), please visit the HSDB record page.

Applications · 5 items

DescriptionCyclohexane is obtained by the distillation of petroleum or by hydrogenation of benzene. It constitutes 0.5–1.0% of petroleum

UsesCyclohexane is a petroleum product obtainedby distilling C4- 400°F boiling rangenaphthas, followed by fractionation andsuperfractionation; also formed by catalytichydrogenation of benzene. It is usedextensively as a solvent for lacquers andresins, as a paint and varnish remover, andin the manufacture of adipic acid, benzene,cyclohexanol, and cyclohexanone.

UsesSuitable for HPLC, spectrophotometry, environmental testing

UsesSolvent for lacquers and resins. Paint and varnish remover. In the extraction of essential oils. In analytical chemistry for mol wt determinations (cryoscopic constant 20.3). In the manufacture of adipic acid, benzene, cyclohexyl chloride, nitrocyclohexane, cyclohexanol and cyclohexanone. In the manufacture of solid fuel for camp stoves. In fungicidal formulations (possesses slight fungicidal action). In the industrial recrystallization of steroids.

General DescriptionA clear colorless liquid with a petroleum-like odor. Used to make nylon, as a solvent, paint remover, and to make other chemicals. Flash point -4°F. Density 6.5 lb / gal (less than water) and insoluble in water. Vapors heavier than air.

Additional notes · 3 items

DefinitionChEBI: An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.

DefinitionA colorless liquid alkane that is commonly used as a solvent and in the production of hexanedioic acid (adipic acid) for the manufacture of nylon. Cyclohexane, itself, is manufactured by the reformation of longer chain hydrocarbons present in crude-oil fractions. It is also interesting from a structural point of view, existing as a ‘puckered’ six-membered ring, having all bonds between carbon atoms at 109.9° (the tetrahedral angle). The molecule undergoes rapid interconversion between two ‘chair-like’ CONFORMATIONS, which are energetically equivalent, passing through a ‘boat-like’ structure of higher energy. It is commonly represented by a hexagon.

Definitioncyclohexane: A colourless liquidcycloalkane, C6H12; r.d. 0.78; m.p.6.5°C; b.p. 81°C. It occurs in petroleumand is made by passing benzeneand hydrogen under pressureover a heated Raney nickel catalyst at150°C, or by the reduction of cyclohexanone.It is used as a solvent andpaint remover and can be oxidizedusing hot concentrated nitric acid tohexanedioic acid (adipic acid). The cyclohexanering is not planar and canadopt boat and chair conformations;in formulae it is representedby a single hexagon.

Related reactions

3,560 records

Linked notes

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