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CAS No.: | 108-94-1 |
---|---|
Name: | Cyclohexanone |
Article Data: | 2587 |
Molecular Structure: | |
Formula: | C6H10O |
Molecular Weight: | 98.1448 |
Synonyms: | AI3-00041;Anon;Anone;CCRIS 5897;Cicloesanone;Cicloesanone [Italian];Cyclohexanon;Cyclohexyl ketone;Cykloheksanon;Cykloheksanon [Polish];Hexanon; |
EINECS: | 203-631-1 |
Density: | 0.947 g/cm3 |
Melting Point: | -16.4 °C |
Boiling Point: | 155.65 °C |
Flash Point: | 44 °C |
Solubility: | Water solubility: 150 g/L (10 °C) |
Appearance: | colourless liquid |
Hazard Symbols: | Xn |
Risk Codes: | 10-20 |
Safety: | 25 |
Transport Information: | UN 1915 3/PG 3 |
PSA: | 17.07000 |
LogP: | 1.51960 |
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; diisobutylaluminium hydride In tetrahydrofuran; diethyl ether; hexane at -50℃; for 0.5h; | 100% |
With hydrogen; mer-Os(PPh3)3HBr(CO) In toluene at 100℃; under 760 Torr; for 24h; | 100% |
With diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In chloroform for 1h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With Fe2(4,4″-dioxido-[1,1′:4′,1″-terphenyl]-3,3″-dicarboxylate); 1-(tert-butylsulfonyl)-2-iodosylbenzene In [D3]acetonitrile at 20℃; for 1.5h; | A 100% B 100% |
With 3-chloro-benzenecarboperoxoic acid; [Ni2(L2H2)(OAc)2] at 20℃; for 1h; | A 7% B 93% |
With 3-chloro-benzenecarboperoxoic acid; (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride In dichloromethane; acetonitrile for 1h; Product distribution; Ambient temperature; other catalysts; kinetic isotope effect; | A 2% B 89% |
Conditions | Yield |
---|---|
With sodium bromite In acetic acid for 5h; Ambient temperature; | 100% |
With potassium permanganate; Sucrose-ethyleneoxide adducts In toluene at 20℃; for 24h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis;; | 100% |
With 4 A molecular sieve; tetrabutylammonium periodite; sodium ruthenate(VI) In dichloromethane at 20℃; for 24h; Oxidation; | 100% |
Conditions | Yield |
---|---|
With Geotrichum candidum CCT 1205 whole cells In aq. phosphate buffer at 28℃; for 24h; pH=6.5; Enzymatic reaction; | A 100% B n/a |
With hydrogen; In methanol at 30℃; under 735.5 Torr; for 5h; | A 0.8% B 98.2% |
With C8H13O2S2(3-)*Na(1+)*Rh(1+)*H(1+); hydrogen In water; toluene at 60℃; under 15001.5 Torr; for 4h; Inert atmosphere; Schlenk technique; Autoclave; | A 90% B 9% |
Conditions | Yield |
---|---|
With copper(II) sulfate In tetrahydrofuran; methanol; water for 3h; Heating; | 100% |
With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 In acetonitrile for 0.333333h; Oxidation; Heating; | 100% |
With Co1.4Cu1.6[Co(CN)6]2; oxygen In ethanol; water at 100℃; under 3750.38 Torr; for 3h; Reagent/catalyst; Time; Solvent; | 100% |
Conditions | Yield |
---|---|
With copper(II) sulfate In tetrahydrofuran; methanol; water for 2h; Heating; | 100% |
2-methyl-1,5-dioxaspiro<5.5>undecane
cyclohexanone
Conditions | Yield |
---|---|
With 4-phenyl-2,2,5,5-tetramethyl-3-imidazolin-1-yloxy-3-oxide; 15-crown-5; KCrO5Cl In acetonitrile at 60℃; for 7h; Product distribution; Further Variations:; Reagents; | 100% |
diethyl ether
A
(1S,3aR,5S,5'S,6R,6a'R)-2,2'-dimethyl-5'-(2-methyl-1,3-dioxolan-4-yl)dihydro-3a'H-3-oxaspiro[bicyclo[3.2.0.]heptane-6,6'-furo[2,3-d][1,3]dioxole]
B
cyclohexanone
Conditions | Yield |
---|---|
With copper(II) bis(trifluoromethanesulfonate); benzene Inert atmosphere; Irradiation; | A 65% B 100% |
Conditions | Yield |
---|---|
With Geotrichum candidum CCT 1205 whole cells In aq. phosphate buffer at 28℃; for 24h; pH=6.5; Baeyer-Villiger Ketone Oxidation; Enzymatic reaction; | A n/a B 100% C n/a |
14,15-dioxa-7-aza-dispiro[5.1.5.2]pentadecane
A
caprolactam
B
11-cyanoundecanoic acid
C
cyclohexanone
Conditions | Yield |
---|---|
With cerium(IV) oxide; 2,2'-azobis(isobutyronitrile) at 50℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere; | A n/a B 99.2% C n/a |
Reported in EPA TSCA Inventory.
OSHA PEL: TWA 25 ppm (skin)
ACGIH TLV: TWA 20 ppm, STEL 50 ppm (skin); Confirmed Animal Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
NIOSH REL: (Ketone (Cyclohexanone)) TWA 100 mg/m3
DOT Classification: 3; Label: Flammable Liquid
For occupational chemical analysis use OSHA: #01 or NIOSH: Ketones I (Desorption in CS2), 1300.
Cyclohexanone, with the CAS register number 108-94-1, is a colorless to pale yellow liquid with a pleasant odor. It is the organic compound with the formula C6H10O. Its EINECS register number is 203-631-1. Cyclohexanone is slightly soluble in water (5-10 g/100 mL), but miscible with ethanol. The substance is stable and combustible, which is incompatible with strong oxidizing agents.Cyclohexanone can form an explosive peroxide with H2O2 and react vigorously with oxidizing materials, such as nitric acid. It is easily ignited by heat, sparks or flames. It will form vapors when it is mixed with air. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas. Its container may explode when heated.
Physical properties about Cyclohexanone are: (1)ACD/LogP: 0.821; (2)ACD/LogD (pH 5.5): 0.82; (3)ACD/LogD (pH 7.4): 0.82; (4)ACD/BCF (pH 5.5): 2.48; (5)ACD/BCF (pH 7.4): 2.48; (6)ACD/KOC (pH 5.5): 66.58; (7)ACD/KOC (pH 7.4): 66.58; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.453; (10)Molar Refractivity: 27.801 cm3; (11)Molar Volume: 102.952 cm3; (12)Polarizability: 11.021 10-24cm3; (13)Surface Tension: 32.523998260498 dyne/cm; (14)Density: 0.953 g/cm3; (15)Flash Point: 46.667 °C; (16)Enthalpy of Vaporization: 39.248 kJ/mol; (17)Boiling Point: 155.749 °C at 760 mmHg; (18)Vapour Pressure: 2.98600006103516 mmHg at 25°C
Preparation of Cyclohexanone: Cyclohexanone can be prepared from cyclohexanol by oxidation with chromic oxide. In addition, it can be produced by the partial hydrogenation of phenol:
C6H5OH + 2 H2 → (CH2)5CO
Besides, Cyclohexanone is also produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:
C6H12 + O2 → (CH2)5CO + H2O
Uses of Cyclohexanone: The great majority of Cyclohexanone is used as the precursors in production of adipic acid, caprolactam, Nylon 6,6 and Nylon 6. It can be used to make nylon, as a chemical reaction medium, and as a solvent, for instance, used in paint, especially in the paint which contains nitrocellulose, polymer or copolymer of chloroethene and polymer of methylacrylic acid ester. Cyclohexanone can also be used in dyeing and as levelling agent of faded light silk.
When you are using Cyclohexanone, you should be very cautious about it. The substance is flammable and harmful, which is harmful by inhalation. What's more, you must avoid contact with your eyes.
You can still convert the following datas into molecular structure of Cyclohexanone:
(1)Canonical SMILES: C1CCC(=O)CC1
(2)InChI: InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
(3)InChIKey: JHIVVAPYMSGYDF-UHFFFAOYSA-N
Toxicity of Cyclohexanone:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
frog | LDLo | subcutaneous | 1900mg/kg (1900mg/kg) | AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 50, Pg. 199, 1903. |
guinea pig | LCLo | inhalation | 400ppm/4H (400ppm) | National Technical Information Service. Vol. AD-A066-307, | |
guinea pig | LDLo | intraperitoneal | 760mg/kg (760mg/kg) | National Technical Information Service. Vol. AD-A066-307, | |
human | TCLo | inhalation | 75ppm (75ppm) | SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 282, 1943. |
mammal (species unspecified) | LC50 | inhalation | 25gm/m3 (25000mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988. | |
mammal (species unspecified) | LD50 | oral | 3gm/kg (3000mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988. | |
monkey | LDLo | intravenous | 284mg/kg (284mg/kg) | Toxicology and Applied Pharmacology. Vol. 37, Pg. 115, 1976. | |
mouse | LCLo | inhalation | 19200mg/m3/90 (19200mg/m3) | GASTROINTESTINAL: OTHER CHANGES | Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979. |
mouse | LD50 | intraperitoneal | 1230mg/kg (1230mg/kg) | GASTROINTESTINAL: OTHER CHANGES | Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979. |
mouse | LD50 | oral | 1400mg/kg (1400mg/kg) | National Technical Information Service. Vol. AD-A066-307, | |
mouse | LDLo | subcutaneous | 1300mg/kg (1300mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: ATAXIA | Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 50, Pg. 199, 1903. |
rabbit | LD50 | intraperitoneal | 1540mg/kg (1540mg/kg) | GASTROINTESTINAL: OTHER CHANGES | Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979. |
rabbit | LD50 | skin | 1mL/kg (1mL/kg) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. | |
rabbit | LDLo | oral | 1600mg/kg (1600mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC | Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 199, 1943. |
rat | LC50 | inhalation | 8000ppm/4H (8000ppm) | Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 18, 1974. | |
rat | LD50 | intraperitoneal | 1130mg/kg (1130mg/kg) | GASTROINTESTINAL: OTHER CHANGES | Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979. |
rat | LD50 | oral | 1620uL/kg (1.62mL/kg) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. | |
rat | LD50 | subcutaneous | 2170mg/kg (2170mg/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 415, 1943. | |
rat | LDLo | intravenous | 568mg/kg (568mg/kg) | Toxicology and Applied Pharmacology. Vol. 37, Pg. 115, 1976. |