1501-82-2

Basic information

• Product Name: CYCLODODECENE
• Synonyms: 1-Cyclododecene;Cyclododecene (c,t);Cyclododecene,c&t;CYCLODODECENE;CYCLODECENE;Cyclododecene (cis- and trans- mixture);Cyclododecene (cis+trans);Cyclododecene, ca 70% trans isomer
• CAS NO: 1501-82-2
• Molecular Formula: C₁₂H₂₂
• Molecular Weight: 166.3
• EINECS: 216-117-7
• Product Categories: Alkenes;Cyclic;Organic Building Blocks
• Mol File: 1501-82-2.mol
• Article Data: 43

Chemical Properties

• Melting Point: 9°C
• Boiling Point: 232-245 °C(lit.)
• Flash Point: 201 °F
• Appearance: /Liquid
• Density: 0.870 g/mL at 20 °C(lit.)
• Vapor Pressure: 9.88E-08mmHg at 25°C
• Refractive Index: n20/D 1.485
• Water Solubility: Insoluble in water. Soluble in alcohol.
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: CYCLODODECENE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLODODECENE(1501-82-2)
• EPA Substance Registry System: CYCLODODECENE(1501-82-2)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R38:Irritating to skin.
• Safety Statements: 23-24/25
• WGK Germany: 1
• Hazardous Substances Data: 1501-82-2(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 80, 1973 DOI: 10.1021/jo00941a015

InChI:InChI=1/2C12H22/c2*1-2-4-6-8-10-12-11-9-7-5-3-1/h2*1-2H,3-12H2/b2-1+;2-1-

Synthetic route

cyclododeca-1,5,9-triene (4904-61-4) → cyclododecane (294-62-2) + cyclododecene (1501-82-2) + cyclododeca-1,5-diene (1502-04-1, 67881-13-4)

Conditions	Yield
With hydrogen at 80 - 160℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;	A 100% B n/a C n/a
With hydrogen; Ru4Sn6/Davison 923 mesoporous silica at 119.84℃; under 22502.3 Torr; for 12h; Product distribution; Further Variations:; reaction times;

meso-1,2-dibromocyclododecane (51371-31-4) → cyclododecene (1501-82-2)

Conditions	Yield
With triethyl borane; tri-n-butyl-tin hydride In hexane; toluene at -78℃; for 0.5h;	96%

2-(cyclododecyloxy)tropone (87563-19-7) → 2-hydroxy-2,4,6-cycloheptatrien-1-one (533-75-5) + cyclododecene (1501-82-2)

Conditions	Yield
In dimethylsulfoxide-d6 at 180℃; for 2h;	A n/a B 95%

triethyl borane (97-94-9) + O-cyclododecyl-S-methyl dithiocarbonate (4373-12-0) → S-Ethyl S'-methyl dithiocarbonate (10596-55-1) + cyclododecane (294-62-2) + cyclododecene (1501-82-2) + 1,1'-bicyclododecane (88011-88-5) + cyclododecanone (830-13-7)

Conditions	Yield
With air In hexane Product distribution; Mechanism; Ambient temperature; variation of temperature; other thiocarbonyl derivatives;	A 91% B 62% C 12% D 9% E 4%

cyclododecanol (1724-39-6) + 4-Phenylbutyric acid (1821-12-1) → cyclododecene (1501-82-2) + cyclododecyl 4-phenylbutyrate

Conditions	Yield
CHF3O3S*C14H13N In n-heptane at 115℃; for 6 - 9h; Product distribution / selectivity;	A 10% B 90%
diphenylammonium trifluoromethanesulfonate In n-heptane at 115℃; for 6 - 10h; Product distribution / selectivity;	A 20% B 71%
With sulfonated polypyrene In n-heptane at 80℃; for 24h;	A 35% B 45%

dimethyl diazomalonate (6773-29-1) + 1,2-epoxycyclododecane (286-99-7) → mesoxalate de methyle (3298-40-6) + cyclododecene (1501-82-2)

Conditions	Yield
With dirhodium tetraacetate In benzene for 0.75h; Heating;	A n/a B 85%

1-(triethoxysilyl)-cyclododecene → cyclododecene (1501-82-2)

Conditions	Yield
With silver fluoride In tetrahydrofuran; methanol; water	84%

cyclododecanecarboxylic acid (884-36-6) → cyclododecene (1501-82-2)

Conditions	Yield
With 2,2-dimethylpropanoic anhydride; bis[2-(diphenylphosphino)phenyl] ether; palladium dichloride In various solvent(s) at 110℃; for 16h;	81%

(1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) → cyclododecane (294-62-2) + cyclododecene (1501-82-2)

Conditions	Yield
With hydrogen at 240℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;	A 71% B 26%

2-cyclododecyloxysulfonyl-benzoic acid 2-(2-methoxy-ethoxy)-ethyl ester (888021-89-4) → chlorocyclododecane (34039-83-3) + cyclododecene (1501-82-2)

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃;	A 66% B 21%

Dodecahydro-1,3-dioxa-2-thia-cyclopentacyclododecene 2,2-dioxide → cyclododecene (1501-82-2)

Conditions	Yield
With iodine; triphenylphosphine In N,N-dimethyl-formamide Heating;	65%

cyclododeca-1,5,9-triene (4904-61-4) → cyclododecene (1501-82-2) + cyclododeca-1,5-diene (1502-04-1, 67881-13-4)

Conditions	Yield
With hydrogen at 240℃; under 760.051 Torr; for 0.000638889h;	A 65% B 25%
Stage #1: cyclododeca-1,5,9-triene With hydrogen; 0.5% palladium on alumina at 120℃; under 825.083 Torr; Industry scale; Gas phase; Stage #2: 0.5% palladium on alumina Product distribution / selectivity;	A n/a B 0.2%
Stage #1: cyclododeca-1,5,9-triene With carbon monoxide; hydrogen; 0.5% palladium on alumina at 120℃; under 825.083 Torr; Industry scale; Gas phase; Stage #2: 0.5% palladium on alumina Product distribution / selectivity;	A n/a B 0.2%
With hydrogen; Ru4Sn6/Davison 923 mesoporous silica at 99.84℃; under 22502.3 Torr; for 8h; Product distribution; Further Variations:; Catalysts; Temperatures;

1,2-epoxycyclododecane (286-99-7) → cyclododecene (1501-82-2)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran at 20℃; Inert atmosphere;	60%
With niobium pentachloride; zinc In tetrahydrofuran; benzene at 23℃; for 24h; Inert atmosphere;	45%
With triethylsilane; [NiNPtBu3]4 In toluene at 90℃; for 12h; Inert atmosphere; Sealed tube;

formyl cyclododecane (5037-22-9) → hydroxymethylcyclododecane (1892-12-2) + cyclododecane (294-62-2) + cyclododecene (1501-82-2)

Conditions	Yield
With [(η4-Ph4C4C-OH)(1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene)IrH2] In 1,3,5-trimethyl-benzene at 160℃; for 20h; Temperature; Concentration; Solvent;	A 14 %Chromat. B n/a C 55%

cyclododecyl iodide (61682-10-8) + benzaldehyde (100-52-7) → cyclododecane (294-62-2) + cyclododecene (1501-82-2) + 1-cyclododecyl-1-phenylmethanol (108229-11-4)

Conditions	Yield
With chromium dichloride; cobalt(II) phthalocyanine In N,N-dimethyl-formamide at 30℃; for 20h;	A 21% B 54% C 2%

cyclododecyl bromide (7795-35-9) → cyclododecane (294-62-2) + cyclododecene (1501-82-2)

Conditions	Yield
With zinc; cob(I)alamin In water; acetic acid at 0℃; for 1h;	A 17 % Chromat. B 76.7 % Chromat.

cyclododeca-1,5,9-triene (4904-61-4) → cyclododecene (1501-82-2)

Conditions	Yield
With hydrogen; nickel(II) In methanol at 150℃; under 36752.9 Torr; var. solvents, var. catalysts Co and Ni complexes; other object of study- activity of catalysts;
With ruthenium trichloride; formaldehyd; hydrogen; acetic acid; triphenylphosphine In ethanol; water at 25 - 160℃; under 7500.75 - 15001.5 Torr; for 6.66667h;
With ruthenium trichloride; formaldehyd; hydrogen; acetic acid; triphenylphosphine In ethanol; water at 25 - 160℃; under 7500.75 - 15001.5 Torr; for 6.66667h;
With ruthenium trichloride; formaldehyd; hydrogen; acetic acid; triphenylphosphine In ethanol at 160℃; under 15001.5 Torr; Temperature; Pressure;

cyclododecanol (1724-39-6) → cyclododecene (1501-82-2)

Conditions	Yield
With silica gel; copper(II) sulfate In 1,1,2,2-tetrachloroethylene for 1h; Heating; pentadecane (internal standard in g.l.c. analysis);	98 % Chromat.
With silica gel; copper(II) sulfate In 1,1,2,2-tetrachloroethylene for 0.416667h; Product distribution; Thermodynamic data; Mechanism; Heating; other solvents, catalysts, adsorbents, different time;	98 % Chromat.

Cyclododecyl p-toluenesulphonate (27092-44-0) → cyclododecene (1501-82-2) + cyclododecanol (1724-39-6)

Conditions	Yield
In water at 100℃; for 15h; Yield given. Yields of byproduct given;

trans-1,2-dibromocyclododecane (51306-71-9, 51371-31-4, 66768-00-1) → cyclododecene (1501-82-2)

Conditions	Yield
With tetrahydrofuran; chromium chloride; lithium aluminium tetrahydride In N,N-dimethyl-formamide at 90℃; Yield given;

Cyclododecyl phenyl telluride (97567-72-1) → cyclododecene (1501-82-2) + cyclododecanol (1724-39-6) + cyclododecyl acetate (6221-92-7) + cyclododecanone (830-13-7)

Conditions	Yield
With sodium periodate; acetic acid at 25℃; for 24h;	A 37 % Chromat. B 10 % Chromat. C 11 % Chromat. D 20 % Chromat.

diisobutylaluminum benzenetellurolate + cyclododecyl methanesulfonate (103763-35-5) → cyclododecene (1501-82-2) + Cyclododecyl phenyl telluride (97567-72-1)

Conditions	Yield
In dichloromethane at -40℃; for 5.5h;	A 43 % Chromat. B 46 % Chromat.

Cyclododecyl phenyl telluride (97567-72-1) + acetic acid (64-19-7) → cyclododecene (1501-82-2) + cyclododecanol (1724-39-6) + cyclododecyl acetate (6221-92-7) + cyclododecanone (830-13-7)

Conditions	Yield
With sodium periodate In water at 25℃; for 24h;	A 37 % Chromat. B 10 % Chromat. C 11 % Chromat. D 20 % Chromat.

C30H38OP(1+)*BF4(1-) → cyclododecene (1501-82-2) + 1-fluorocyclododecane (61682-09-5)

Conditions	Yield
In tetrahydrofuran for 0.666667h; Heating; Yield given. Yields of byproduct given;

cyclododecane (294-62-2) → cyclododecene (1501-82-2)

Conditions	Yield
IrH2[anthracene(P-t-Bu2)-1,8] at 230℃; Product distribution; Further Variations:; Temperatures; Catalysts;
With C28H54BIrN2P2 at 230℃; for 20h; Catalytic behavior; Temperature; Glovebox;

cyclododecyl bromide (7795-35-9) → cyclododecene (1501-82-2)

Conditions	Yield
With silver tetrafluoroborate In nitromethane; N,N-dimethyl-formamide at 20℃; for 12h;

cyclododecanol (1724-39-6) → chlorocyclododecane (34039-83-3) + cyclododecene (1501-82-2)

Conditions	Yield
With trichloroacetamide; triphenylphosphine In dichloromethane at 30℃; for 0.25h;

1-bromocyclododec-1-ene (1132-79-2) + phenylboronic acid (98-80-6) → (Z)-1-bromocyclododec-1-ene (16250-58-1) + cyclododecene (1501-82-2) + (E)-1-phenylcyclododecene

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water Suzuki coupling; Heating;

cyclododecene (1501-82-2) → 1,2-epoxycyclododecane (286-99-7)

Conditions	Yield
With tert.-butylhydroperoxide In toluene at 79.84℃; for 4.83333h; Temperature; Concentration;	100%
With phosphoric acid; sodium tungstate; sulfuric acid; dihydrogen peroxide; aliquat 336 In water at 90℃; for 4h; pH=3;	99.6%
With copper 1,3,5-benzenetricarboxylate; oxygen; pivalaldehyde In acetonitrile at 40℃; under 760.051 Torr; for 6h;	99%

cyclododecene (1501-82-2) → cyclododecane (294-62-2)

Conditions	Yield
With aluminum oxide; sodium tetrahydroborate; nickel dichloride In hexane at 40℃; Catalytic hydrogenation;	100%
With ethanol; lithium; nickel dichloride; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at 20℃; for 1h;	99%
With hydrogen; NiCl2-Li-[poly(2-vinyl-naphthalene)-co-(divinylbenzene)] In tetrahydrofuran at 20℃; under 760.051 Torr; for 1h;	99%

cyclododecene (1501-82-2) + benzene (71-43-2) → phenylcyclododecane (15971-88-7)

Conditions	Yield
With Et3NH[Al2Cl7] at 40℃; for 6h; Temperature; Inert atmosphere;	98%
ethylaluminum dichloride

diiodomethane (75-11-6) + cyclododecene (1501-82-2) → bicyclo<10.1.0>tridecane (3105-35-9)

Conditions	Yield
With tetradecafluorohexane; triethylaluminum In hexane at 20℃; for 36h; Darkness;	98%

methanol (67-56-1) + cyclododecene (1501-82-2) → 12,12-dimethoxydodecanal (84201-78-5)

Conditions	Yield
Stage #1: cyclododecene With ozone In methanol; dichloromethane at -40℃; Stage #2: With toluene-4-sulfonic acid In methanol at 20℃; for 1.5h; Stage #3: methanol With dimethylsulfide; sodium hydrogencarbonate at 20℃;	92%

1,4-Butanediol diacrylate (1070-70-8) + cyclododecene (1501-82-2) → polymer; monomer(s): 1,4-butanediol diacrylate; cyclododecene

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane Heating;	91%

cyclododecene (1501-82-2) → cyclododecyl iodide (61682-10-8)

Conditions	Yield
With titanium(IV) iodide In dichloromethane at 20℃; for 12h;	91%

cyclododecene (1501-82-2) + O-tosylhydroxylamine (52913-14-1) → 13-aza-bicyclo[10.1.0]tridecane (286-98-6)

Conditions	Yield
In dichloromethane	90%

cyclododecene (1501-82-2) → 1-fluoro-2-iodocyclododecane (410096-79-6)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; N-iodo-succinimide; perfluoropropylene; diethylamine In water; toluene for 24h; Ambient temperature;	88%
With triethylamine pentahydrogen fluoride salt; triethylammonium iodide In dichloromethane at 20℃; Electrochemical reaction;	84%
With iodine pentafluoride-pyridine-hydrogen fluoride; potassium iodide In dichloromethane at 0 - 20℃; for 17.5h; Reagent/catalyst;	78%
With iodine pentafluoride-pyridine-hydrogen fluoride; potassium iodide In dichloromethane at 0 - 20℃; for 17.5h;	78%

cyclododecene (1501-82-2) + N-methylaniline (100-61-8) → N-(cyclododecylmethyl)aniline

Conditions	Yield
With chlorotris(dimethylamido)(κ2-N,O-3-phenyl-2-pyridonato)tantalum(V) In (2)H8-toluene at 145℃; for 44h; Glovebox; Inert atmosphere;	88%

cyclododecene (1501-82-2) → cyclododecanone (830-13-7)

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile at 55℃; for 12h; Wacker Oxidation;	87%
With tert.-butylhydroperoxide; silver hexafluoroantimonate; [Pd(Quinox)Cl2] In dichloromethane; water at 20℃; Wacker Oxidation; regioselective reaction;	76%
With dinitrogen monoxide for 1h; Flow reactor;	52%
With dinitrogen monoxide In cyclohexane at 300 - 350℃; under 75007.5 Torr; for 6h; Temperature; Flow reactor;

cyclododecene (1501-82-2) + bis(4-fluorophenyl)disulfide (405-31-2) → 2-(4-fluorophenylthio)cyclododecan-1-one

Conditions	Yield
Stage #1: bis(4-fluorophenyl)disulfide In dichloromethane at -78℃; Electrolysis; Stage #2: cyclododecene In dichloromethane; dimethyl sulfoxide at -78℃; for 0.0833333h; Schlenk technique; Stage #3: With triethylamine In dichloromethane; dimethyl sulfoxide at -78 - 25℃; for 1.08333h; Schlenk technique;	87%

cyclododecene (1501-82-2) → perdeuterated cyclododecene (97797-70-1)

Conditions	Yield
With water-d2; palladium on activated charcoal at 250℃; for 12h;	85%
With water-d2; palladium on activated charcoal at 250℃; for 4h;	84%

cyclododecene (1501-82-2) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile for 24h;	85%
With tetrafluoroboric acid; iodomesitylene; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water; acetonitrile at 50℃; for 10h; Inert atmosphere;	77 %Spectr.
With potassium peroxymonosulfate; iodobenzene In water; acetonitrile at 60℃; for 8h;	82 %Spectr.

Bromoform (75-25-2) + cyclododecene (1501-82-2) → 13,13-dibromobicyclo<10.1.0>tridecane (17301-57-4)

Conditions	Yield
With potassium hydroxide; benzyltrimethylammonium chloride In ethanol; water for 12h;	84%
With potassium tert-butylate In hexane at 10℃; for 4h; Inert atmosphere;
With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In ethanol; water at 0 - 20℃; for 16h;

cyclododecene (1501-82-2) + N-(benzenesulfonyl)-N-[(trifluoromethyl)sulfanyl]benzenesulfonamide → 2-(trifluoromethylthio)cyclododecanol

Conditions	Yield
With dimethyl sulfoxide at 20℃; for 2h; Schlenk technique; Inert atmosphere;	84%

cyclododecene (1501-82-2) → 1,2-dichlorocyclododecane (82936-35-4)

Conditions	Yield
With chloro-trimethyl-silane; nitro acetate In dichloromethane at -10℃;	83%
With chlorine In dichloromethane at -10℃;

cyclododecene (1501-82-2) + ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0) → Propionic acid 3a,4,5,6,7,8,9,10,11,12,13,13a-dodecahydro-1-oxa-2-aza-cyclopentacyclododecen-3-yl ester

Conditions	Yield
In toluene for 80h; Ambient temperature;	81%

isopropyl acrylate (689-12-3) + cyclododecene (1501-82-2) → diisopropyl (2E,14E)-hexadec-2,14-dienoate

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 16h; Inert atmosphere; Reflux;	81%

cyclododecene (1501-82-2) → C48H88O12 + C48H88O16 (74515-85-8)

Conditions	Yield
With ozone-containing oxygen In diethyl ether at -70℃; for 1h;	A n/a B 80%

cyclododecene (1501-82-2) → α-Chlorcyclododecanonoxim (4575-77-3, 4806-74-0, 6667-06-7) + C24H44Cl2N2O2 (121779-61-1)

Conditions	Yield
With chloro-trimethyl-silane; isopentyl nitrite at -10℃; Neat (no solvent);	A 10% B 80%

Upstream product

• 103-82-2 phenylacetic acid 
• 294-62-2 cyclododecane 
• 1724-39-6 cyclododecanol 
• 530-48-3 1,1-Diphenylethylene 
• 34039-83-3 chlorocyclododecane 
• 706-31-0 (1E,5E,9Z)-cyclododeca-1,5,9-triene 
• 5037-22-9 formyl cyclododecane 
• 6221-92-7 cyclododecyl acetate 
• 286-99-7 1,2-epoxycyclododecane 
• 4904-61-4 cyclododeca-1,5,9-triene 
• 1486-75-5 (E)-Cyclododecen 
• 1132-79-2 1-bromocyclododec-1-ene 
• 98-80-6 phenylboronic acid 
• 7795-35-9 cyclododecyl bromide 

Downstream Products

• 74285-16-8 methyl 12-oxotridecanoate 
• 1731-79-9 dodecanedioic acid dimethyl ester 
• 286-99-7 1,2-epoxycyclododecane 
• 77059-21-3 2,3-epoxy-cyclododecanol 
• 112-41-4 1-dodecene 
• 765-03-7 1-dodecyne 
• 294-62-2 cyclododecane 
• 2986-54-1 Cyclododecyl methyl ether 
• 51302-77-3 bicyclo<7.3.0>dodecane 
• 3956-80-7 12-oxododecanoic acid 
• 693-23-2 1,12-dodecanedioic acid 
• 35951-28-1 2-chlorocyclododecanone 
• 21964-49-8 tetradeca-1,13-diene 
• 6221-92-7 cyclododecyl acetate 

Relevant articles and documents

Studies on partial hydrogenation of 1,5,9-cyclo-dodecatriene towards cyclo-dodecene

The selective hydrogenation of 1,5,9-cis,trans,trans-cyclo-dodecatriene (1,5,9-ctt-CDT) towards cyclo-dodecene (CDE) depends strongly on the pressure of hydrogen, respectively the hydrogenation rate. High yields of CDE (>90%) can only be reached at extremely low hydrogen pressure. In order to elucidate this exceptional reaction performance the course of reaction has been studied for a wide range of hydrogen pressure, 0.01>pH2>2.5MPa, taking into consideration data of other research groups. The CDT hydrogenations were discontinuously carried out in liquid phase on Pd/Al2O3 at T = 353 K. The resulting hypothesis of this study is that the very low reaction rate at low pH2 is necessary in order to realize a dense surface coverage of 1,5,9-CDT and 1,5-cyclo-dodecadiene (CDD) isomers where these molecules show adsorption on Pd via two double bonds so that readsorption of formed CDE and subsequent hydrogenation to cyclo-dodecane (CDA) is hardly possible. On the whole this new hypothesis on the reaction course of CDT hydrogenation gives a sound and fully consistent view on this rather complicated reaction.

Hydrogenation of 1,5,9-Cyclododecatriene in a Three-Phase System in the Presence of Nickel Nanoparticles Supported on NаX Zeolite

The hydrogenation of 1,5,9-cyclododecatriene in the presence of nanostructured Ni catalysts, supported with NaX zeolite, in a flow-through reactor at atmospheric hydrogen pressure was investigated. Nickel nanoparticles on the support surface were prepared by chemical reduction of the precursor (NiCl2) with NaBH4 and NH2NH2. The effect exerted on the yield of hydrogenation products by the nominal residence time of the gas phase in the reaction zone and by the process temperature was considered, and the catalyst operation life was analyzed. The catalysts showed high activity and allowed preparation of cyclododecane in ~100% yield at a process temperature of up to 160°С.

METHOD FOR MANUFACTURING CYCLODODECANONE AND APPARATUS FOR MANUFACTURING THE SAME

A method for manufacturing cyclododecanone according to the present invention has an effect of having a significantly high conversion rate of cyclododecene and selectivity of cyclododecanone, can minimize the cost used for equipment and processes, is practical, and has an advantageous effect on industrial mass production compared to the prior art by significantly reducing a reaction residence time and a required reaction volume of a reactor.COPYRIGHT KIPO 2019