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Cyclohexanone
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Cyclohexanone
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Cyclohexanone
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108-94-1 Cyclohexanone
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Amadis Chemical offer CAS#108-94-1;CAT#A801945
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Cyclohexanone CAS:108-94-1
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108-94-1 Usage

Health Hazard

Inhalation of vapors from hot material can cause narcosis. The liquid may cause dermatitis.

Definition

ChEBI: A cyclic ketone that consists of cyclohexane bearing a single oxo substituent.

General Description

A colorless to pale yellow liquid with a pleasant odor. Less dense than water . Flash point 111°F. Vapors heavier than air. Used to make nylon, as a chemical reaction medium, and as a solvent.

Reactivity Profile

Cyclohexanone forms an explosive peroxide with H2O2, and reacts vigorously with oxidizing materials (nitric acid).

Chemical properties

Colorless, clear liquid with soil smell; its impure product appears as light yellow color. Easily soluble in ethanol and ether.

Purification Methods

Dry cyclohexanone with MgSO4,CaSO4, Na2SO4 or Linde type 13X molecular sieves, then distil it. Cyclohexanol and other oxidisable impurities can be removed by treatment with chromic acid or dilute KMnO4. More thorough purification is possible by conversion to the bisulfite addition compound, or the semicarbazone, followed by decomposition with Na2CO3 and steam distillation. [For example, equal weights of the bisulfite adduct (crystallised from water) and Na2CO3 are dissolved in hot water and, after steam distillation, the distillate is saturated with NaCl and extracted with Et2O which is then dried (anhydrous MgSO4 or Na2SO4), filtered and the solvent evaporated prior to further distillation.] FLAMMABLE [Beilstein 7 III 14, 7 IV 15.]

Production method

In the 1940s, the industrial production of cyclohexanone mainly applied hydrogenation of phenol to generate cyclohexanol, followed by dehydrogenation to give cyclohexanone. In the 1960s, with the development of petrochemical industry, the cyclohexane oxidation production method gradually dominated. In 1967, the one step method of phenol hydrogenation, developed by the Netherlands National Mining Company (DSM) was industrialized. This method has short production process, good product quality and high yield, but the raw materials of phenol and catalyst are expensive, so the majority of the industry still adopts the cyclohexane oxidation method.
1. Phenol method takes nickel as a catalyst; first apply hydrogenation of phenol to give cyclohexanol, followed by dehydrogenation to give cyclohexanone using zinc as the catalyst for zinc.
2. Cyclohexane oxidation method uses cyclohexane as the raw material; first apply non-catalyst condition; use oxygen-rich air for oxidation to give cyclohexyl hydroperoxide, followed by decomposition into the mixture of cyclohexanol, cyclohexanone, alcohol and ketone in the presence of tert-butyl chromate catalyst; further apply a series of distillation refinement to get qualified products. Raw material consumption quota: cyclohexane (99.6%) 1040kg / t.
3. Benzene hydrogenation oxidation method; benzene subjects to hydrogenation (with hydrogen) at 120-180 ℃ in the presence of nickel catalyst to generate cyclohexane; cyclohexane has oxidation reaction with air at 150-160 ℃, 0.908MPa to obtain the mixture of cyclohexanol and cyclohexanone; separate them to obtain the cyclohexanone product. Cyclohexanol is dehydrogenated at 350-400 ° C in the presence of a zinc-calcium catalyst to produce cyclohexanone. Raw material consumption quotas: benzene (99.5%) 1144kg / t, hydrogen (97.0%) 1108kg / t, caustic soda (42.0%) 230kg / t.

Air & Water Reactions

Flammable. Soluble in water.

Fire Hazard

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 hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Chemical Properties

colourless liquid

Application

It is the raw material for the production of caprolactam and adipic acid; used as the solvents and diluent agents of paints, inks, synthetic resins and synthetic rubber; also used as leather degreasing agent.
Used as organic solvent;
Raw materials and solvents of synthetic resin and synthetic fiber;
Cyclohexanone is an important chemical raw material, being the major intermediates of making nylon, caprolactam and adipic acid. It is also an important industrial solvent, for example, for paints, especially for those containing nitrocellulose, vinyl chloride polymers and their copolymers or methacrylate polymer paints. Used as an excellent solvent for pesticides such as organophosphate insecticide. It is used as a solvent for dyes, viscous solvents for piston aviation lubricants, solvents for greases, waxes and rubbers. Also used as leveling agent for dyeing and fading silk; degreasing agents for polishing metal; wood coloring paint; also used for cyclohexanone stripping, decontamination and spot removal. Cyclohexanone and cyanoacetic acid can have condensation reaction to generate cyclohexylidene acetic acid, and then followed by elimination and decarboxylation to get cyclohexene acetonitrile, and finally giving cyclohexene ethylamine by hydrogenation [3399-73-3]. Cyclohexene ethylamine is a intermediate for some drugs.
The solvents for fibers, resins, rubbers, paraffins, shellac and DDT; for organic synthesis; it can dissolve many of the complexes formed by the elements and organic reagents; bismuth determination; extract rare metal such as uranium, thorium, cobalt and titanium.

Contact allergens

Used as a polyvinyl chloride solvent, cyclohexanone caused contact dermatitis in a woman manufacturing PVC fluidotherapy bags. Cyclohexanone probably does not cross-react with cyclohexanone resin. A cyclohexanone-derived resin used in paints and varnishes caused contact dermatitis in painters
InChI:1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2

108-94-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (29135)  Cyclohexanone  Selectophore, ≥99.5% 108-94-1 29135-500ML 2,438.28CNY Detail
Sigma-Aldrich (29135)  Cyclohexanone  Selectophore, ≥99.5% 108-94-1 29135-100ML 789.75CNY Detail
Sigma-Aldrich (29135)  Cyclohexanone  Selectophore, ≥99.5% 108-94-1 29135-10ML 376.74CNY Detail
Sigma-Aldrich (29140)  Cyclohexanone  puriss. p.a., ≥99.5% (GC) 108-94-1 29140-1L 862.29CNY Detail
Sigma-Aldrich (29140)  Cyclohexanone  puriss. p.a., ≥99.5% (GC) 108-94-1 29140-500ML 573.30CNY Detail
Sigma-Aldrich (29140)  Cyclohexanone  puriss. p.a., ≥99.5% (GC) 108-94-1 29140-100ML 420.03CNY Detail
Alfa Aesar (A15607)  Cyclohexanone, 99+%    108-94-1 2500ml 545.0CNY Detail
Alfa Aesar (A15607)  Cyclohexanone, 99+%    108-94-1 500ml 279.0CNY Detail
Alfa Aesar (A15607)  Cyclohexanone, 99+%    108-94-1 100ml 175.0CNY Detail
Alfa Aesar (33309)  Cyclohexanone, ACS, 99+%    108-94-1 *4x1L 1334.0CNY Detail
Alfa Aesar (33309)  Cyclohexanone, ACS, 99+%    108-94-1 4L 1300.0CNY Detail
Alfa Aesar (33309)  Cyclohexanone, ACS, 99+%    108-94-1 1L 369.0CNY Detail

108-94-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclohexanone

1.2 Other means of identification

Product number -
Other names cyclo-hexanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Adhesives and sealant chemicals,Agricultural chemicals (non-pesticidal),CBI,Intermediates,Paint additives and coating additives not described by other categories,Solvents (for cleaning or degreasing),Solvents (which become part of product formulation or mixture)
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:108-94-1 SDS

108-94-1Synthetic route

cyclohexenone
930-68-7

cyclohexenone

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
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%
cyclohexane
110-82-7

cyclohexane

A

cyclohexanone
108-94-1

cyclohexanone

B

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
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%
cyclohexanol
108-93-0

cyclohexanol

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
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%
cyclohexenone
930-68-7

cyclohexenone

A

cyclohexanone
108-94-1

cyclohexanone

B

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
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%
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
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%
cyclohexanone hydrazone
6156-08-7

cyclohexanone hydrazone

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 2h; Heating;100%
2-methyl-1,5-dioxaspiro<5.5>undecane
6413-26-9, 147441-58-5, 147441-59-6

2-methyl-1,5-dioxaspiro<5.5>undecane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
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
60-29-7

diethyl ether

C20H30O6

C20H30O6

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]
1244773-04-3

(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
108-94-1

cyclohexanone

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate); benzene Inert atmosphere; Irradiation;A 65%
B 100%
cyclohexenone
930-68-7

cyclohexenone

A

hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

B

cyclohexanone
108-94-1

cyclohexanone

C

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
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
21842-28-4

14,15-dioxa-7-aza-dispiro[5.1.5.2]pentadecane

A

caprolactam
105-60-2

caprolactam

B

11-cyanoundecanoic acid
5810-18-4

11-cyanoundecanoic acid

C

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
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
cyclohexen-1-ol
4065-81-0

cyclohexen-1-ol

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With [Ru(η(3):η(3)-C10H16)Cl(O2CCH3)] In aq. phosphate buffer at 50℃; for 10h; pH=7; Sealed tube; Inert atmosphere;99%
With perchloric acid; acetaldehyde; acetone; sodium chloride In water at 25℃; Rate constant; Equilibrium constant; Irradiation;
With sulfuric acid In water at 25℃; Rate constant; Equilibrium constant;
In water at 25℃; Equilibrium constant; ionic strength: 0.01 M;
at 19.9 - 59.9℃; Equilibrium constant; Thermodynamic data; keto-enol-tautomerism, keto-enol-association; ΔH;
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With water at 80℃; for 0.25h; microwave irradiation;99%
With silica gel; iron(III) chloride at 20℃; for 0.0833333h;97%
With water; Nafion-H In acetone for 0.5h;95%
1,1-diethoxycyclohexane
1670-47-9

1,1-diethoxycyclohexane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With water at 80℃; for 0.25h; microwave irradiation;99%
With water; acetone; mesoporous aluminosilicate at 55℃; for 2h;85%
With aluminium(III) iodide In acetonitrile; benzene for 0.166667h; Ambient temperature;90 % Chromat.
With erbium(III) triflate In nitromethane for 0.5h; Product distribution; Further Variations:; Solvents; reaction time;
cyclohexyl-1-phenyl-1-hydroperoxide
20614-61-3

cyclohexyl-1-phenyl-1-hydroperoxide

A

cyclohexanone
108-94-1

cyclohexanone

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
Fe/W/Zr oxide catalyst of example 3 In acetone at 70℃; Product distribution / selectivity;A 99%
B 99%
With sulfuric acid In decane; nitromethane Product distribution / selectivity;A 99.56 %Chromat.
B 99.47 %Chromat.
sulfuric acid In decane; nitromethane at 53℃; Product distribution / selectivity;
2,2,3,3-tetramethyl-1,4-dioxaspiro<4.5>decane
32893-35-9

2,2,3,3-tetramethyl-1,4-dioxaspiro<4.5>decane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With iron(III) chloride hexahydrate; acetaldehyde In dichloromethane for 1h; Reflux;99%
phenol
108-95-2

phenol

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With Pd nanoparticles and TiO2; hydrogen; hydrazine hydrate In water at 80℃; under 450.045 Torr; for 10h; Catalytic behavior; Kinetics; Mechanism; Reagent/catalyst;98.9%
With hydrogen at 160 - 200℃; under 1125.11 Torr; for 1h; Reagent/catalyst; Autoclave;96.3%
With 2 mol-% Pd/C; hydrogen; potassium formate In water at 90℃; for 6h; Temperature; Reagent/catalyst;94%
cyclohexane
110-82-7

cyclohexane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With methyltrifluoromethyldioxirane In dichloromethane at -22℃; for 0.3h;98%
With hydrogenchloride; FeH6Mo6O24(3-)*3H3N*3H(1+)*7H2O; tetrabutylammomium bromide; dihydrogen peroxide In 1,4-dioxane; water at 85℃; for 24h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst;98%
With dihydrogen peroxide at 49.84℃; for 3h; Catalytic behavior; Temperature; Reagent/catalyst;93.1%
1,3-dioxolane-2-spirocyclohexane
177-10-6

1,3-dioxolane-2-spirocyclohexane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With 1,1,1-trifluoro-2-propanone; methyltrifluoromethyldioxirane In dichloromethane at 0℃; for 2h; also dimethyldioxirane efficiently afford cleavage of acetals and ketals to carbonyl products under mild, neutral conditions through α-CH insertion, also react dialkyl ethers and cyclic ethers to alcohols, aldehydes, carboxylic axids or to lactones;98%
With 1,1,1-trifluoro-2-propanone; methyltrifluoromethyldioxirane In dichloromethane at 0℃; for 2h;98%
With iron(III) chloride In dichloromethane for 0.25h; Ambient temperature;96%
1,5-dithiaspiro[5.5]undecane
180-96-1

1,5-dithiaspiro[5.5]undecane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; dihydrogen peroxide In water; acetonitrile at 20℃; for 0.75h;98%
With acetic acid at 20℃; for 6h;82%
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 3h; Micellar solution;75%
N'-cyclohexylidene-N,N-dimethyl-hydrazine
10424-93-8

N'-cyclohexylidene-N,N-dimethyl-hydrazine

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With baker's yeast; phosphate buffer In ethanol at 37℃; for 12h;98%
With triethylene diamine nickel thiosulfate; water In chloroform at 20℃; for 0.0833333h; Hydrolysis;94%
With chloro-trimethyl-silane; sodium iodide In water; acetonitrile for 0.05h; deprotection;92%
cyclohexane-1,1-diylbis(phenylsulfane)
37457-08-2

cyclohexane-1,1-diylbis(phenylsulfane)

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20 - 25℃; for 2h; Irradiation;98%
Cyclohex-2-enol
822-67-3

Cyclohex-2-enol

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With [Ru(η(5)-C5,κ-P-Cp(P))(CH3CN)2]PF6 In tetrahydrofuran-d8 at 60℃; for 5h; Inert atmosphere;97%
With tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; potassium carbonate In acetonitrile for 1h; Inert atmosphere; Reflux;96%
With bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (1,3,5-triaza-7-phosphaadamantane); isopropyl alcohol In water at 100℃; for 1h; Reagent/catalyst;95.5%
cyclohexanone semicarbazone
1589-61-3

cyclohexanone semicarbazone

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With ammonium chlorochromate on aluminum oxide In diethyl ether for 0.5h; Heating; various conditions;97%
With zirconium hydrogen sulfate; silica gel In hexane at 20℃; for 0.3h;92%
With water; silica gel; tetrabromosilane In tetrachloromethane at 20℃; for 0.233333h;90%
3-Butyl-1,2,5-trioxa-spiro[5.5]undecan-4-one

3-Butyl-1,2,5-trioxa-spiro[5.5]undecan-4-one

A

2-oxohexanoic acid
2492-75-3

2-oxohexanoic acid

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
triethylamine In dichloromethane at 20 - 25℃; for 16h;A 97%
B n/a
cyclohexanone phenylhydrazone
946-82-7

cyclohexanone phenylhydrazone

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With baker's yeast; phosphate buffer In ethanol at 37℃; for 11h;97%
With caro's acid; silica gel for 0.05h; Oxidation; Irradiation;94%
With iron(II) sulfate In chloroform at 20℃; for 0.75h; Hydrolysis;90%
2-hexyl-1,4-dioxa-spiro[4.5]decane

2-hexyl-1,4-dioxa-spiro[4.5]decane

A

1,2-octandiol
1117-86-8

1,2-octandiol

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With sodium bromate; ammonium cerium(IV) nitrate In acetonitrile at 80℃; for 0.333333h;A 97%
B 95%
rac-octan-2-ol
4128-31-8

rac-octan-2-ol

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With C53H46ClN3P2Ru; potassium tert-butylate; acetone at 56℃; under 750.075 Torr; for 0.666667h; Oppenauer Oxidation;97%
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

acetaldehyde
75-07-0

acetaldehyde

A

Acetaldehyde oxime
107-29-9

Acetaldehyde oxime

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With sulfuric acid at 4 - 10℃; for 2h;A 97%
B 97%
pyrrolidine
123-75-1

pyrrolidine

cyclohexanone
108-94-1

cyclohexanone

1-(1-Cyclohexen-1-yl)pyrrolidine
1125-99-1

1-(1-Cyclohexen-1-yl)pyrrolidine

Conditions
ConditionsYield
In toluene for 18h; Molecular sieve; Dean-Stark trap; Heating / reflux;100%
With sulfuric acid In toluene Dean-Stark; Reflux;99%
With K-10 Montmorillonite clay In toluene for 2.5h; Heating;95%
furfural
98-01-1

furfural

cyclohexanone
108-94-1

cyclohexanone

(2E,6E)-2,6-bis(2-furylmethylene)cyclohexanone
62085-75-0

(2E,6E)-2,6-bis(2-furylmethylene)cyclohexanone

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 0.025h; microwave irradiation;100%
With sodium hydroxide In ethanol; water at 20℃; for 24h; Inert atmosphere; Green chemistry;99%
aluminum oxide for 0.0416667h; microwave irradiation;98%
methanol
67-56-1

methanol

cyclohexanone
108-94-1

cyclohexanone

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With trimethyl orthoformate at 40℃; under 6000480 Torr; for 8h;100%
With chloranil In acetonitrile for 0.5h; Irradiation;99%
With trimethyl orthoformate at 20℃; for 0.5h;98%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

cyclohexanone
108-94-1

cyclohexanone

ethyl cyclohexylideneacetate
1552-92-7

ethyl cyclohexylideneacetate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil for 1h;
Stage #2: cyclohexanone In tetrahydrofuran; mineral oil for 18h;
100%
With sodium hydride In tetrahydrofuran for 8h;98%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With 15-crown-5; sodium hydride In tetrahydrofuran; mineral oil at 0℃;
Stage #2: cyclohexanone In tetrahydrofuran; mineral oil at -40 - 20℃;
97%
Pentaerythritol
115-77-5

Pentaerythritol

cyclohexanone
108-94-1

cyclohexanone

7,11,18,21-tetraoxa-trispiro[5.2.2.5.2.2]heneicosane
183-10-8

7,11,18,21-tetraoxa-trispiro[5.2.2.5.2.2]heneicosane

Conditions
ConditionsYield
With sulfuric acid at 80℃;100%
With pyrographite In toluene for 8h; Heating;94%
peroxodisulfate ion; zirconium(IV) oxide In toluene for 4h; Heating;94%
1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

cyclohexanone
108-94-1

cyclohexanone

2-methyl-1,5-dioxaspiro<5.5>undecane
6413-26-9, 147441-58-5, 147441-59-6

2-methyl-1,5-dioxaspiro<5.5>undecane

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In benzene for 8.5h; Heating;100%
With pyridine; toluene-4-sulfonic acid In benzene Condensation; Heating;100%
With toluene-4-sulfonic acid In benzene Heating;81%
With MOR zeolite supported Bronsted acidic ionic liquid at 50℃; for 2h;68.1%
With toluene-4-sulfonic acid; benzene
cyclohexanone
108-94-1

cyclohexanone

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

cyclopenta-2,4-dien-1-ylidenecyclohexane
3141-04-6

cyclopenta-2,4-dien-1-ylidenecyclohexane

Conditions
ConditionsYield
Stage #1: cyclohexanone; cyclopenta-1,3-diene With pyrrolidine In methanol at 20℃; Inert atmosphere;
Stage #2: With acetic acid In methanol for 0.15h;
100%
In methanol for 0.416667h; Ambient temperature; new method;96%
With pyrrolidine In methanol for 0.416667h; Ambient temperature;96%
cyclohexanone
108-94-1

cyclohexanone

benzaldehyde
100-52-7

benzaldehyde

2-Benzylidenecyclohexanone
5682-83-7

2-Benzylidenecyclohexanone

Conditions
ConditionsYield
Stage #1: cyclohexanone With sodium hydroxide In ethanol; water at 0 - 5℃;
Stage #2: benzaldehyde In ethanol; water
100%
With CaO modified with benzyl bromide In methanol at 65℃; under 760.051 Torr; for 3h; Reagent/catalyst; Concentration; Temperature; Time;95.8%
With N,N-Dimethyltrimethylsilylamine; magnesium bromide ethyl etherate at 20℃; for 16h; Inert atmosphere; neat (no solvent);93%
cyclohexanone
108-94-1

cyclohexanone

1-Ethynyl-1-cyclohexanol
78-27-3

1-Ethynyl-1-cyclohexanol

1,2-di(1-hydroxycyclohexyl)acetylene
78-54-6

1,2-di(1-hydroxycyclohexyl)acetylene

Conditions
ConditionsYield
Stage #1: 1-Ethynylcyclohexan-1-ol With ethylmagnesium bromide In tetrahydrofuran at 23 - 80℃;
Stage #2: cyclohexanone In tetrahydrofuran at 23 - 25℃;
Stage #3: With ammonium chloride In tetrahydrofuran; water
100%
With sodium hydroxide; tetrabutylammomium bromide In toluene at 70℃; for 2h;89%
Stage #1: 1-Ethynylcyclohexan-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: cyclohexanone With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; hexane at -78 - 20℃; for 14h;
74%
cyclohexanone
108-94-1

cyclohexanone

ethylene glycol
107-21-1

ethylene glycol

1,3-dioxolane-2-spirocyclohexane
177-10-6

1,3-dioxolane-2-spirocyclohexane

Conditions
ConditionsYield
With zeolite HSZ-360 In toluene for 3h; Heating;100%
With [Al(H2O)6][MS]3 In cyclohexane for 0.833333h; Reagent/catalyst; Dean-Stark; Reflux;100%
With AgOTf and (3-(3,5-bis(diphenylphosphino)phenyl)-pyridine) In toluene for 12h; Reflux;99%
cyclohexanone
108-94-1

cyclohexanone

ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

1,4-dithiaspiro[4.5]decane
177-16-2

1,4-dithiaspiro[4.5]decane

Conditions
ConditionsYield
With thionyl chloride; silica gel In toluene for 24h; Heating;100%
With bentonite In toluene for 3h; Heating;99%
With silica gel; iron(III) chloride In dichloromethane Ambient temperature;99%
cyclohexanone
108-94-1

cyclohexanone

allyl bromide
106-95-6

allyl bromide

1-allyl-1-cyclohexanol
1123-34-8

1-allyl-1-cyclohexanol

Conditions
ConditionsYield
With ammonium acetate; zinc In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;100%
zinc In N,N-dimethyl-formamide for 2h; Product distribution; Ambient temperature; other solvents : N,N-dimethylacetoamide, N-methyl-2-pyrrolidone, 2-pyrrolidone, 2-methyloxazoline;99%
With zinc In N,N-dimethyl-formamide for 2h; Ambient temperature; other solvents : N,N-dimethylacetoamide, N-methyl-2-pyrrolidone, 2-pyrrolidone, 2-methyloxazoline;99%
cyclohexanone
108-94-1

cyclohexanone

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

1-hydroxy-1-cyclohexanecarbonitrile
931-97-5

1-hydroxy-1-cyclohexanecarbonitrile

Conditions
ConditionsYield
With Hevea brasiliensis (S)-hydroxynitrile lyase pH=4.5; aq. buffer; Enzymatic reaction;100%
With titanium(IV) isopropylate; dl-3-(2-hydroxy-1-naphthylidene)-imino-ε-caprolactam (Nap-ACL) In dichloromethane for 3h; Ambient temperature;99%
With ytterbium(III) isopropoxide In tetrahydrofuran for 0.5h; Ambient temperature;94%
cyclohexanone
108-94-1

cyclohexanone

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-cyano-2-cyclohexylideneacetate
6802-76-2

ethyl 2-cyano-2-cyclohexylideneacetate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In neat liquid at 20℃; for 0.133333h; Knoevenagel Condensation; Green chemistry;100%
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.333333h; Knoevenagel condensation;98%
With ammonium acetate; acetic acid In toluene Knoevenagel Condensation; Reflux;97%
cyclohexanone
108-94-1

cyclohexanone

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

3H-spiro{benzothiazole-2,1'-cyclohexane}
182-53-6

3H-spiro{benzothiazole-2,1'-cyclohexane}

Conditions
ConditionsYield
With trifluoroacetic acid at 80℃; for 16h; Reagent/catalyst;100%
In toluene Heating;93.8%
With aluminum oxide In neat (no solvent) at 20℃; for 0.5h; Inert atmosphere;92%
cyclohexanone
108-94-1

cyclohexanone

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide
4545-18-0

N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide

Conditions
ConditionsYield
In methanol at 20℃; for 3h;100%
In methanol at 20℃; Inert atmosphere;99.5%
With hydrogenchloride In methanol for 24h; Heating;97%
cyclohexanone
108-94-1

cyclohexanone

benzylamine
100-46-9

benzylamine

N-benzylcyclohexylamine
4383-25-9

N-benzylcyclohexylamine

Conditions
ConditionsYield
With formic acid; Cp*IrCl(N-(phenyl(pyridin-2-yl)methyl)methanesulfonamide)complex In ethyl acetate at 40℃; for 18h; Reagent/catalyst; Inert atmosphere;100%
Stage #1: cyclohexanone; benzylamine With formic acid; chlorido(8-quinolinolato-k2N,O)(η5-pentamethylcyclopentadienyl)iridium(III) In ethyl acetate at 0 - 40℃; Inert atmosphere; Schlenk tube; Cooling with ice;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Product distribution / selectivity;
98%
With 4 A molecular sieve; borane pyridine complex In methanol for 16h;96%
cyclohexanone
108-94-1

cyclohexanone

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

1-oxa-4-thia-spiro[4.5]decane
177-15-1

1-oxa-4-thia-spiro[4.5]decane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether for 3h; Heating;100%
With hydrogenchloride In diethyl ether at 20℃; for 0.15h;98%
bis(acetylacetonato)dioxidomolybdenum(VI) In acetonitrile at 20℃; for 3.5h;96%
cyclohexanone
108-94-1

cyclohexanone

malononitrile
109-77-3

malononitrile

2-(cyclohexylidene)malononitrile
4354-73-8

2-(cyclohexylidene)malononitrile

Conditions
ConditionsYield
hydrotalcite structure integrating fluoride ions In DMF (N,N-dimethyl-formamide) at 25℃; for 2h; Conversion of starting material; Knoevenagel Condensation;100%
With 1-butyl-1,4-diazabicyclo[2.2.2]octanylium hydrotetrafluoroborate In water at 20℃; for 0.0333333h; Knoevenagel condensation;100%
Ru(+)Cp*(NCCHCO2Et)(-)*(PPh3)2 In tetrahydrofuran at 25℃; for 5h; Condensation; Aldol reaction;99%
cyclohexanone
108-94-1

cyclohexanone

hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

Conditions
ConditionsYield
With Fe(AAEMA)3; oxygen; isobutyraldehyde In 1,2-dichloro-ethane under 760 Torr; for 36h; Ambient temperature;100%
With borax; dihydrogen peroxide; N-benzyl-N,N,N-triethylammonium chloride In water; benzene at 55℃; for 24h;100%
With bismuth(lll) trifluoromethanesulfonate In dichloromethane at 20℃; for 0.5h; Baeyer-Villiger oxidation;100%
cyclohexanone
108-94-1

cyclohexanone

2-bromocyclohexanone
1056477-06-5

2-bromocyclohexanone

Conditions
ConditionsYield
With N-Bromosuccinimide; toluene-4-sulfonic acid In dichloromethane; cyclohexanone at 0℃; for 4h; Reflux;100%
With N-Bromosuccinimide; toluene-4-sulfonic acid In dichloromethane at 0℃; for 4h; Reflux;98%
With Cl(CF2)4SO2Br In tetrachloromethane at 10℃; for 0.166667h;95%
cyclohexanone
108-94-1

cyclohexanone

Adipic acid
124-04-9

Adipic acid

Conditions
ConditionsYield
With sodium nitrite In trifluoroacetic acid100%
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 5.25h; Product distribution / selectivity;100%
With dihydrogen peroxide; ortho-tungstic acid In water at 90℃; for 20h; Product distribution / selectivity;99%
cyclohexanone
108-94-1

cyclohexanone

6-Hydroxyhexanoic acid
1191-25-9

6-Hydroxyhexanoic acid

Conditions
ConditionsYield
Stage #1: cyclohexanone With potassium peroxomonosulfate In water at 20℃; Baeyer-Villiger oxidation;
Stage #2: With water at 20℃; Solvolysis; Further stages.;
100%
With dihydrogen peroxide; n-butylstannoic acid; acetic acid at 70℃; for 8h;87%
With Oxone In hexane; water at 40℃; for 6h; Baeyer-Villiger oxidation;77%
cyclohexanone
108-94-1

cyclohexanone

Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

Conditions
ConditionsYield
With N,O-bis(trimethylsilyl)hydroxylamine; potassium hydride In tetrahydrofuran for 1.5h; Ambient temperature; - 78 deg C to room temp.;100%
With acetic acid; acetone oxime at 120℃; for 1h;100%
With ammonium chloride; Amberlyst A-21 In ethanol for 1h; Ambient temperature;100%
cyclohexanone
108-94-1

cyclohexanone

2-Chlorocyclohexanone
822-87-7

2-Chlorocyclohexanone

Conditions
ConditionsYield
With iodine; mercury dichloride In dichloromethane for 0.5h; Ambient temperature;100%
With N-chloro-succinimide In dimethyl sulfoxide at 20℃; for 0.166667h;92%
With N-chloro-succinimide In various solvent(s) at 20℃; for 0.416667h;90%
cyclohexanone
108-94-1

cyclohexanone

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
With hydrogen; 5 percent Rh/MgO; magnesium oxide In water at 323℃; under 15001.2 Torr; Product distribution;100%
With Triethoxysilane; benzoic acid ethyl ester; cesium fluoride at 25℃; for 0.0166667h;100%
With zinc(II) tetrahydroborate In acetonitrile for 0.166667h; Ambient temperature;100%
ethanol
64-17-5

ethanol

cyclohexanone
108-94-1

cyclohexanone

1,1-diethoxycyclohexane
1670-47-9

1,1-diethoxycyclohexane

Conditions
ConditionsYield
With trimethyl orthoformate at 60℃; under 6000480 Torr; for 8h;100%
With orthoformic acid triethyl ester at 20℃; for 1h;96%
iodine for 1h;90%

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Continuous liquid-phase phenol hydrogenation to cyclohexanone over Pd/Al2O3 was conducted in a membrane dispersion based fixed-bed reactor system. The effects of membrane structure on the phenol hydrogenation and gas–liquid two-phase flow were investigated by experimental results coupled with c...detailed

Improving the energy efficiency and production performance of the Cyclohexanone (cas 108-94-1) ammoximation process via thermodynamics, kinetics, dynamics, and economic analyses08/20/2019

Cyclohexanone ammoximation is widely used as an efficient method to synthesize cyclohexanone oxime in industrial production. In this study, the cyclohexanone ammoximation production process was explored based on reaction kinetics in order to reduce its energy consumption and total annual cost. T...detailed

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