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Basic Information
CAS No.: 78-18-2
Name: Cyclohexanone peroxide
Molecular Structure:
Molecular Structure of 78-18-2 (Cyclohexanone peroxide)
Formula: C12H22 O5
Molecular Weight: 246.304
Synonyms: Peroxide,1-hydroperoxycyclohexyl 1-hydroxycyclohexyl (6CI,7CI);1-Hydroxy-1'-hydroperoxydicyclohexyl peroxide; Perhexa P
EINECS: 201-091-1
Density: 1.2 g/cm3
Melting Point: 76-77 °C
Boiling Point: 374.7 °C at 760 mmHg
Flash Point: 180.4 °C
Appearance: White to colorless solid.
Hazard Symbols: Dangerous fire risk, powerful oxidizer.
Safety: Slightly toxic by parenteral route. A severe eye and skin irritant. When heated to decomposition it emits acrid smoke and irritating vapors.
PSA: 74.60000
LogP: 3.05660
Related products
Synthetic route
108-94-1

cyclohexanone

78-93-3

butanone

A

78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

B

126-76-1

3,6-dimethyl-3,6-dihydroperoxy-4,5-dioxaoctane

Conditions
ConditionsYield
With C14H34N2O6S2(2+)*2HO4S(1-)A 95.2%
B 96.4%
...Expand
108-94-1

cyclohexanone

78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

Conditions
ConditionsYield
With dihydrogen peroxide; nitric acid at 18℃; for 2h; Kinetics; Thermodynamic data; Temperature; Time;96.2%
With dihydrogen peroxide In Petroleum ether at 70 - 80℃; for 4h; Solvent;88.7%
With sulfuric acid; dihydrogen peroxide at 10℃; for 1h;84%
766-07-4

cyclohexyl hydroperoxide

A

78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

B

2407-94-5

1,1'-dihydroxycyclohexyl peroxide

C

2699-12-9

bis-(1-hydroperoxycyclohexyl)peroxide

D

108-94-1

cyclohexanone

Conditions
ConditionsYield
With ozone In tetrachloromethane at 20℃; Kinetics;
...Expand
108-94-1

cyclohexanone

A

78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

B

2407-94-5

1,1'-dihydroxycyclohexyl peroxide

C

2699-12-9

bis-(1-hydroperoxycyclohexyl)peroxide

Conditions
ConditionsYield
With dihydrogen peroxide In tetrachloromethane
...Expand
7647-01-0

hydrogenchloride

7732-18-5

water

7722-84-1

dihydrogen peroxide

108-94-1

cyclohexanone

78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

...Expand
7647-01-0

hydrogenchloride

60-29-7

diethyl ether

7732-18-5

water

7722-84-1

dihydrogen peroxide

108-94-1

cyclohexanone

78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

...Expand
108-93-0

cyclohexanol

peroxide

peroxide

oxygen

oxygen

A

78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

B

bis-<1-hydroxy-cyclohexyl>-peroxide ?

bis-<1-hydroxy-cyclohexyl>-peroxide ?

...Expand
78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

2699-12-9

bis-(1-hydroperoxycyclohexyl)peroxide

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide at 20℃; for 24h;92%
With dihydrogen peroxide
78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

78-94-4

methyl vinyl ketone

A

73154-83-3

2,12-Tridecanedione

B

590-90-9

1-Hydroxy-3-butanone

C

333-60-8

2-oxodecanoic acid

D

108-94-1

cyclohexanone

Conditions
ConditionsYield
With titanium(III) chloride; acetic acid for 3h; Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts;A 26%
B n/a
C n/a
D n/a
With titanium(III) chloride; acetic acid for 3h; Ambient temperature; Yield given. Title compound not separated from byproducts;A 26%
B n/a
C n/a
D n/a
...Expand
110-86-1

pyridine

78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

98-88-4

benzoyl chloride

13213-29-1

1,1-bis-benzoylperoxy-cyclohexane

Conditions
ConditionsYield
unter Kuehlung;
...Expand
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Chemistry

Molecular Formula: C12H22O5
Molar mass: 246.3001 g/mol
Nominal Mass: 246 Da 
Average Mass: 246.3001 Da 
Monoisotopic Mass: 246.146724 Da
Density: 1.2 g/cm3
Flash Point: 180.4 °C
Index of Refraction: 1.518
Boiling Point: 374.7 °C at 760 mmHg
Vapour Pressure: 3.81E-07 mmHg at 25°C
Structure of Cyclohexanone peroxide (78-18-2):

XLogP3-AA: 2.3
H-Bond Donor: 2
H-Bond Acceptor: 5
Systematic Name of Cyclohexanone peroxide (78-18-2): 1-(1-Hydroperoxycyclohexyl)peroxycyclohexan-1-ol 
SMILES: O(OC1(OO)CCCCC1)C2(O)CCCCC2 
InChI: InChI=1/C12H22O5/c13-11(7-3-1-4-8-11)16-17-12(15-14)9-5-2-6-10-12/h13-14H,1-10H2 
InChIKey: UICXTANXZJJIBC-UHFFFAOYAL 
Std. InChI: InChI=1S/C12H22O5/c13-11(7-3-1-4-8-11)16-17-12(15-14)9-5-2-6-10-12/h13-14H,1-10H2 
Std. InChIKey: UICXTANXZJJIBC-UHFFFAOYSA-N 

Toxicity Data With Reference

1.    

eye-rbt 80 mg/1M RNS SEV

     ZAARAM    Zentralblatt fuer Arbeitsmedizin und Arbeitsschutz. 8 (1958),25.
2.    

par-mus LD50:2 g/kg

     NCPBBY    National Clearinghouse for Poison Control Centers, Bulletin. U.S. Department of Health, Education, and Welfare (Washington, DC) Jan/Feb ,1969.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Slightly toxic by parenteral route. A severe eye and skin irritant. When heated to decomposition it emits acrid smoke and irritating vapors.

Standards and Recommendations

DFG MAK: Strong Skin Effects

Specification

 Cyclohexanone peroxide (78-18-2) also can be called Perhexa P ; Cyclohexanol, 1-((1-hydroperoxycyclohexyl)dioxy)- ; 1-Hydroperoxycyclohexyl 1-hydroxycyclohexyl peroxide ;and 1-Hydroxy-1'-hydroperoxydicyclohexyl peroxide .