Product Name

  • Name

    6-Caprolactam

  • EINECS 203-313-2
  • CAS No. 105-60-2
  • Article Data439
  • CAS DataBase
  • Density 1.01 g/cm3
  • Solubility 4560 g/L (20 °C) in water
  • Melting Point 68-71 °C(lit.)
  • Formula C6H11NO
  • Boiling Point 272.5 °C at 760 mmHg
  • Molecular Weight 113.159
  • Flash Point 136.7 °C
  • Transport Information UN 2811 6.1/PG 2
  • Appearance white crystalline solid
  • Safety 2
  • Risk Codes 20/22-36/37/38
  • Molecular Structure Molecular Structure of 105-60-2 (6-Caprolactam)
  • Hazard Symbols HarmfulXn
  • Synonyms 1-Aza-2-cycloheptanone;2-Azacycloheptanone;2-Ketohexamethylenimine;2-Perhydroazepinone;6-Caprolactam;6-Hexanelactam;A 19374;AP (lactam);Aminocaproic lactam;Azepan-2-one;Caprolactam;Hexahydro-1H-azepin-2-one;Hexahydro-2-azepinone;Hexahydro-2H-azepin-2-one;Hexano-6-lactam;Hexanoicacid, 6-amino-, cyclic lactam;Hexanolactam;NSC 117393;NSC 25536;NSC 4977;e-Caprolactam;w-Caprolactam;
  • PSA 29.10000
  • LogP 1.00540

Synthetic route

Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 20℃; for 3h; Beckmann rearrangement;100%
With supercritical water; sulfuric acid at 374.84℃; under 300030 Torr; for 0.000202222h;99.5%
With 1,3,5-trichloro-2,4,6-triazine at 60℃; for 2h; Beckmann rearrangement;99%
1-[(2-oxazepan-1-yl)carbonyl]azepan-2-one
19494-73-6

1-[(2-oxazepan-1-yl)carbonyl]azepan-2-one

[1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane
1760-24-3

[1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane

A

caprolactam
105-60-2

caprolactam

B

C15H31N3O5Si

C15H31N3O5Si

Conditions
ConditionsYield
In toluene at 75℃; for 3h;A n/a
B 100%
...Expand
3-(trimethoxysilyl)propan-1-amine
13822-56-5

3-(trimethoxysilyl)propan-1-amine

1-[(2-oxazepan-1-yl)carbonyl]azepan-2-one
19494-73-6

1-[(2-oxazepan-1-yl)carbonyl]azepan-2-one

A

caprolactam
105-60-2

caprolactam

B

n-[5-(trimethoxysilyl)-2-aza-1-oxo-pentyl]caprolactam

n-[5-(trimethoxysilyl)-2-aza-1-oxo-pentyl]caprolactam

Conditions
ConditionsYield
In toluene at 75℃; for 3h;A n/a
B 100%
...Expand
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

dimethyl sulfate
77-78-1

dimethyl sulfate

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
In N,N-dimethyl-formamide99.6%
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

epichlorohydrin
106-89-8

epichlorohydrin

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
In N,N-dimethyl-formamide99.5%
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
...Expand
1-amino-5-cyanopentane
2432-74-8

1-amino-5-cyanopentane

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
99.1%
99%
98.9%
6-aminohexanoic acid
60-32-2

6-aminohexanoic acid

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
zeolite F-9 In toluene for 20h; Heating;99.1%
zeolite F-9 In toluene for 20h; Product distribution; Heating; other catalyst, other solvent;99.1%
With di(n-butyl)tin oxide In xylene for 12h; Heating;95%
methyl 6-oxohexanoate
6654-36-0

methyl 6-oxohexanoate

A

caprolactam
105-60-2

caprolactam

B

poly(6-aminocaproamide-co-6-aminocaproic acid)

poly(6-aminocaproamide-co-6-aminocaproic acid)

C

6-aminocaproic amide
373-04-6

6-aminocaproic amide

D

methyl 6-aminohexanoate hydrochloride
2780-89-4

methyl 6-aminohexanoate hydrochloride

E

6-aminohexanoic acid
60-32-2

6-aminohexanoic acid

Conditions
ConditionsYield
Stage #1: methyl 6-oxohexanoate With ammonia In methanol; water at 35℃; under 22502.3 Torr; for 0.00416667h;
Stage #2: With hydrogen; 5 % ruthenium on Al2O3 In methanol; water at 120℃; under 22502.3 Torr; for 22h;		A 99%
B n/a
C n/a
D n/a
E n/a
...Expand
caprolactam; 6-aminocaproic acid; 6-aminocaproic amide; nylon-6-oligomers; water; mixture of

caprolactam; 6-aminocaproic acid; 6-aminocaproic amide; nylon-6-oligomers; water; mixture of

A

caprolactam
105-60-2

caprolactam

B

pentamide
626-97-1

pentamide

C

5-hexenoic acid
1577-22-6

5-hexenoic acid

D

hexanoic acid
142-62-1

hexanoic acid

E

valeric acid
109-52-4

valeric acid

Conditions
ConditionsYield
at 300℃; under 9000.9 Torr; for 5h;A 99%
B n/a
C n/a
D n/a
E n/a
Stage #1: caprolactam; 6-aminocaproic acid; 6-aminocaproic amide; nylon-6-oligomers; water; mixture of at 220℃; under 5250.53 - 52505.3 Torr; for 0.5h;
Stage #2: at 300℃; under 9000.9 - 90009 Torr; for 5h;		A 99%
B n/a
C n/a
D n/a
E n/a
...Expand
1-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-hexahydro-2H-azepin-2-one
22993-71-1

1-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-hexahydro-2H-azepin-2-one

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
With methanesulfonic acid; water In tert-butyl alcohol at 80℃; for 2h;98%
cyclohexanone
108-94-1

cyclohexanone

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
With sodium azide; methanesulfonic acid In 1,2-dimethoxyethane at -30 - 20℃; for 3h;96%
With XY-zeolite; hydroxylamine hydrochloride for 0.0333333h; microwave irradiation;95%
With sodium azide; sulfuric acid; silica gel at 60℃; for 0.583333h; Schmidt reaction;92%
O-methylcaprolactim
2525-16-8

O-methylcaprolactim

naphthalene-2-carboxylate
93-09-4

naphthalene-2-carboxylate

A

caprolactam
105-60-2

caprolactam

B

methyl naphthalene-2-carboxylate
2459-25-8

methyl naphthalene-2-carboxylate

Conditions
ConditionsYield
at 80 - 85℃; for 16h;A n/a
B 96%
...Expand
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

A

caprolactam
105-60-2

caprolactam

B

cyclohexenone
930-68-7

cyclohexenone

C

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
Hβ zeolite In various solvent(s) at 349.9℃; under 750.06 Torr; Title compound not separated from byproducts;A 95.9%
B 0.8%
C 0.7%
With Mg-Al-borate-pillared layerd double hydroxides at 340℃; for 4h; Product distribution; Further Variations:; Reagents; Beckmann rearrangement; vapor-phase;
With WOx/SBA-15 (10 wt.percent W) In methanol at 350℃; for 3h; Beckmann rearrangement; Inert atmosphere; Flow reactor;
...Expand
1-oxa-2-azaspiro[2.5]octane
185-80-8

1-oxa-2-azaspiro[2.5]octane

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
With Vanadium(IV)-verbindung95%
tert-butyl 2-oxoazepane-1-carboxylate
106412-36-6

tert-butyl 2-oxoazepane-1-carboxylate

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 50℃; for 18h; Sealed tube;95%
With silica gel; ytterbium(III) triflate In neat (no solvent) at 40℃; for 3h; Yield given;
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

A

caprolactam
105-60-2

caprolactam

B

hex-5-enenitrile
5048-19-1

hex-5-enenitrile

C

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
silica-boria catalyst at 250℃;A 93%
B n/a
C n/a
silica-boria at 250℃; Product distribution; Effect of silica-boria catalyst.;
With benzene; boria-hydroxyapatite at 300℃; Product distribution; further catalysts;
potassium phosphate at 350℃; Product distribution; study of activity and selectivity of various phosphate catalysts in the Beckmann rearrangement; other temperatures; other catalysts;
With calcined hierarchical silicalite-1 octahedra comprising highly-branched and orthogonally-stacked nanoplates catalyst In ethanol at 349.84℃; Beckmann Rearrangement; Inert atmosphere;
...Expand
nylon-6

nylon-6

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
In water; toluene at 370℃; under 96759.7 Torr; for 1h; Autoclave; Supercritical conditions;93%
With C2F6NO4S2(1-)*C11H20N3(1+) In PP13; TFSA at 300℃;80%
cyclohexanone
108-94-1

cyclohexanone

A

caprolactam
105-60-2

caprolactam

B

Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride In neat (no solvent) at 70℃; for 15h; Temperature; Solvent; Time;A 7%
B 92%
With acetylhydroxamic acid; sulfuric acid In acetonitrile at 80℃; under 1292.9 Torr; for 0.166667h; Microwave irradiation;A 83%
B 4%
With hydroxylamine hydrochloride In acetonitrile at 100℃; for 3h; Temperature;A 72%
B 23%
N-(benzyloxycarbonyl)-2-oxo-azepane
23511-69-5

N-(benzyloxycarbonyl)-2-oxo-azepane

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
Stage #1: N-(benzyloxycarbonyl)-2-oxo-azepane With diethylaluminium chloride In hexane; dichloromethane at -78℃; for 0.166667h;
Stage #2: With methyl-phenyl-thioether In hexane; dichloromethane at 0℃; for 1h;		92%
1-[(2-oxazepan-1-yl)carbonyl]azepan-2-one
19494-73-6

1-[(2-oxazepan-1-yl)carbonyl]azepan-2-one

dopamine hydrochloride
62-31-7

dopamine hydrochloride

A

caprolactam
105-60-2

caprolactam

B

N-(3,4-dihydroxyphenethyl)-2-oxoazepane-1-carboxamide

N-(3,4-dihydroxyphenethyl)-2-oxoazepane-1-carboxamide

Conditions
ConditionsYield
With triethylamine In chloroform at 20 - 90℃; for 48h;A n/a
B 92%
...Expand
O-methylcaprolactim
2525-16-8

O-methylcaprolactim

benzoic acid
65-85-0

benzoic acid

A

caprolactam
105-60-2

caprolactam

B

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

Conditions
ConditionsYield
at 80 - 85℃; for 16h;A n/a
B 91%
...Expand
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

A

caprolactam
105-60-2

caprolactam

B

hexanenitrile
628-73-9

hexanenitrile

C

hex-5-enenitrile
5048-19-1

hex-5-enenitrile

D

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With boron(III) phosphate In benzene at 300℃; under 750.06 Torr; for 2.66667h; Product distribution; Further Variations:; Catalysts; Solvents; Beckmann rearrangement;A 90.4%
B n/a
C n/a
D n/a
Hβ(10)500 In benzene at 300℃; Product distribution; Further Variations:; Catalysts; Solvents; Temperatures;
...Expand
C12H21N3
185350-62-3

C12H21N3

1-amino-5-cyanopentane
2432-74-8

1-amino-5-cyanopentane

A

caprolactam
105-60-2

caprolactam

B

ethyl 6-aminohexanoate
371-34-6

ethyl 6-aminohexanoate

Conditions
ConditionsYield
With water; titanium(IV) oxide In ethanol at 230℃; under 60006 Torr;A 90%
B n/a
...Expand
1-azacycloheptane-2-thione
7203-96-5

1-azacycloheptane-2-thione

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2h; Ambient temperature;89%
With eosin; oxygen In N,N-dimethyl-formamide at 20℃; for 10h; Irradiation; Green chemistry;87%
With manganese(IV) oxide In chloroform Ambient temperature;85%
1-triisopropylsilyloxy-1-azidocyclohexane

1-triisopropylsilyloxy-1-azidocyclohexane

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
In cyclohexane for 1h; Irradiation;89%
In cyclohexane at 0℃; for 3.5h; Schmidt Reaction; Inert atmosphere; UV-irradiation;83%
N-benzyl-2-azetidinone
4458-64-4

N-benzyl-2-azetidinone

7-Methylsulfanyl-2,3,4,5-tetrahydro-1H-azepine
80096-41-9

7-Methylsulfanyl-2,3,4,5-tetrahydro-1H-azepine

A

caprolactam
105-60-2

caprolactam

B

N-benzyl 3-methylthiopropionamide
80096-38-4

N-benzyl 3-methylthiopropionamide

Conditions
ConditionsYield
at 140℃; for 72h; sealed tube;A 88.5%
B 59.8%
...Expand
N-hydroxysuccinimide ester of 6-{[(benzyloxy)carbonyl]amino}hexanoic acid
53733-98-5

N-hydroxysuccinimide ester of 6-{[(benzyloxy)carbonyl]amino}hexanoic acid

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate88%
2-aminocaprolactam
21568-87-6

2-aminocaprolactam

caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
With potassium hydroxide; hydroxylamine-O-sulfonic acid In water at 0 - 95℃; for 0.333333h; pH=11; Temperature; pH-value; Flow reactor;88%
With potassium hydroxide; hydroxylamine-O-sulfonic acid In water at -5 - 75℃; for 4h; Product distribution / selectivity;75%
With hydrogen sulfide; hydrogen; Ru-S/C (8 molpercent) In tetrahydrofuran at 250℃; under 5171.62 Torr; for 8h; Product distribution / selectivity;42%
caprolactam
105-60-2

caprolactam

α-chlorooxohexamethylenimine
19434-64-1

α-chlorooxohexamethylenimine

Conditions
ConditionsYield
With sodium hypochlorite; acetic acid; tert-butyl alcohol In toluene at 0℃; for 2h;100%
With sodium hypochlorite; acetic acid; tert-butyl alcohol In toluene at -5 - 0℃; for 2h;100%
With trichloroisocyanuric acid In dichloromethane at 20℃; for 1h;99%
caprolactam
105-60-2

caprolactam

N-nitroso-6-caprolactam
35784-01-1

N-nitroso-6-caprolactam

Conditions
ConditionsYield
With sodium acetate; Nitrogen dioxide In dichloromethane at -20℃;100%
With sodium acetate; dinitrogen tetraoxide In dichloromethane at -10℃; for 1h;100%
With hydrogenchloride; water; sodium nitrite
With mixture of gaseous nitrogen oxides; acetic acid
With pyridine; nitrosonium tetrafluoroborate In acetonitrile
caprolactam
105-60-2

caprolactam

benzyl bromide
100-39-0

benzyl bromide

1-Benzyl-hexahydro-azepin-2-on
33241-96-2

1-Benzyl-hexahydro-azepin-2-on

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 4h; 0 deg C to 25 deg C;100%
Stage #1: caprolactam With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;		98%
With sodium hydride In tetrahydrofuran; paraffin 1.) 0 deg C to room temperature, 2 h, 2.) room temperature, 2 h;96%
caprolactam
105-60-2

caprolactam

ethyl acrylate
140-88-5

ethyl acrylate

3-(2-Oxo-azepan-1-yl)-propionic acid ethyl ester
88948-41-8

3-(2-Oxo-azepan-1-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran Michael addition reaction;100%
With tetraethoxy orthosilicate; cesium fluoride In neat (no solvent) at 25℃; for 1h;89%
caprolactam
105-60-2

caprolactam

benzyl chloroformate
501-53-1

benzyl chloroformate

N-(benzyloxycarbonyl)-2-oxo-azepane
23511-69-5

N-(benzyloxycarbonyl)-2-oxo-azepane

Conditions
ConditionsYield
Stage #1: caprolactam With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: benzyl chloroformate In tetrahydrofuran at 20℃; for 10h;		100%
With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h;88%
Stage #1: caprolactam With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: benzyl chloroformate In tetrahydrofuran at -78 - 20℃; Inert atmosphere;		52%
With sodium hydride 1.) THF, 2.) THF, from 0 to 25 deg C, 75 min; Yield given. Multistep reaction;
caprolactam
105-60-2

caprolactam

(isocyanatomethyl)methoxydimethylsilane
35450-25-0

(isocyanatomethyl)methoxydimethylsilane

hexahydro-N-[(methoxydimethylsilyl)methyl]-2-oxo-1H-azepine-1-carboxamide

hexahydro-N-[(methoxydimethylsilyl)methyl]-2-oxo-1H-azepine-1-carboxamide

Conditions
ConditionsYield
In 1,4-dioxane for 4h; Heating / reflux;100%
caprolactam
105-60-2

caprolactam

acetamide
60-35-5

acetamide

Azepan-2-one; compound with acetamide

Azepan-2-one; compound with acetamide

Conditions
ConditionsYield
at 90℃; Inert atmosphere;100%
caprolactam
105-60-2

caprolactam

1-dodecylbromide
143-15-7

1-dodecylbromide

Azone
59227-89-3

Azone

Conditions
ConditionsYield
With sodium hydroxide In water; toluene99.6%
With sodium hydroxide In toluene95%
With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate In cyclohexane92.8%
caprolactam
105-60-2

caprolactam

6-aminohexanoic acid
60-32-2

6-aminohexanoic acid

Conditions
ConditionsYield
With dodecatungstosilic acid; water at 75℃; for 6h; Reagent/catalyst; Large scale;99.4%
With water; sodium hydroxide at 120℃; under 1500.15 Torr; for 11h; Temperature; Pressure; Time;98.5%
Stage #1: caprolactam With acetic acid In water; acetone at 120℃; for 12h;
Stage #2: With ethylamine at 15℃; for 12h; Reagent/catalyst; Temperature; Solvent;		88.1%
caprolactam
105-60-2

caprolactam

1-azacycloheptane-2-thione
7203-96-5

1-azacycloheptane-2-thione

Conditions
ConditionsYield
With pyridin-1-ium-1-yl[pyridin-1-ium-1-yl(sulfido)phosphinothioyl]sulfanyl-sulfido-thioxo-phosphane In acetonitrile for 0.5h; Reflux;99%
With Lawessons reagent In tetrahydrofuran at 20℃; for 0.0833333h;98%
With 2,4-{[3-[(CH2)5C8F17]-4-MeO-phenyl]}2-P2S2 2,4-disulfide In tetrahydrofuran for 2h;96%
caprolactam
105-60-2

caprolactam

1-amino-5-cyanopentane
2432-74-8

1-amino-5-cyanopentane

Conditions
ConditionsYield
With manganese(IV) oxide; ammonia at 200℃; under 9750.98 Torr; Reagent/catalyst; Temperature; Pressure;99%
With ammonia; silica gel; copper at 360℃;
caprolactam
105-60-2

caprolactam

allyl bromide
106-95-6

allyl bromide

N-allyl-ε-caprolactam
17356-28-4

N-allyl-ε-caprolactam

Conditions
ConditionsYield
Stage #1: caprolactam With sodium hydride In tetrahydrofuran
Stage #2: allyl bromide In tetrahydrofuran		99%
With sodium hydride In tetrahydrofuran at 20℃;92%
With potassium hydroxide 1.) toluene, 80 deg C to 90 deg C, 45 min, 2.) toluene; Yield given. Multistep reaction;
caprolactam
105-60-2

caprolactam

2-(ethylthio)acetyl chloride
54256-37-0

2-(ethylthio)acetyl chloride

1-ethylsulfenylacetylazepan-2-one
221444-88-8

1-ethylsulfenylacetylazepan-2-one

Conditions
ConditionsYield
In benzene for 12h; Heating;99%
In benzene
caprolactam
105-60-2

caprolactam

para-iodoanisole
696-62-8

para-iodoanisole

1-(4-methoxyphenyl)hexahydro-2H-azepin-2-one

1-(4-methoxyphenyl)hexahydro-2H-azepin-2-one

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 24h; Inert atmosphere;99%
With potassium phosphate; copper(l) iodide; glycine In 1,4-dioxane at 100℃; for 24h; Goldberg reaction;92%
With pyridine; [Cu2(pda)3(ReO4)2]2*2H2O; caesium carbonate at 170℃; for 3h; Inert atmosphere;87%
caprolactam
105-60-2

caprolactam

hex-1-yne
693-02-7

hex-1-yne

N-((E)-hex-1-enyl)azepan-2-one
1128000-71-4

N-((E)-hex-1-enyl)azepan-2-one

Conditions
ConditionsYield
With dmap; ruthenium trichloride; tributylphosphine; water; potassium carbonate In toluene at 100℃; for 15h; optical yield given as %de;99%
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 1,4-bis(dicyclohexylphosphino)butane; ytterbium(III) triflate In chlorobenzene at 60℃; for 16h; Inert atmosphere; optical yield given as %de;32%
caprolactam
105-60-2

caprolactam

benzyl chloroformate
501-53-1

benzyl chloroformate

N-Benzoylcaprolactam
6248-28-8

N-Benzoylcaprolactam

Conditions
ConditionsYield
Stage #1: caprolactam With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: benzyl chloroformate In tetrahydrofuran; hexane at -78 - 20℃; for 2h;		99%
caprolactam
105-60-2

caprolactam

6-nitrohexanoic acid
10269-96-2

6-nitrohexanoic acid

Conditions
ConditionsYield
With methyltrifluoromethyldioxirane In water at 0℃; for 2h;99%
With methyltrifluoromethyldioxirane; trifluoroacetic acid In acetone at 0℃; for 3h;99%
caprolactam
105-60-2

caprolactam

carbon monoxide
201230-82-2

carbon monoxide

isoprene
78-79-5

isoprene

A

1-(4-methylpent-3-enoyl)azepan-2-one

1-(4-methylpent-3-enoyl)azepan-2-one

B

C12H19NO2

C12H19NO2

Conditions
ConditionsYield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; under 30003 Torr; for 20h; Autoclave;A 99%
B n/a
...Expand
caprolactam
105-60-2

caprolactam

carbon monoxide
201230-82-2

carbon monoxide

phenylacetylene
536-74-3

phenylacetylene

1-(2-phenylacryloyl)azepan-2-one

1-(2-phenylacryloyl)azepan-2-one

Conditions
ConditionsYield
With bis(2-(diphenylphosphanyl)-1H-pyrrol-1-yl)methane; palladium(II) acetylacetonate; toluene-4-sulfonic acid In toluene at 100℃; under 30003 Torr; for 12h; Autoclave; regioselective reaction;99%
...Expand
caprolactam
105-60-2

caprolactam

hexahydro-azepin-2-one; hydrogenphosphate
19411-98-4

hexahydro-azepin-2-one; hydrogenphosphate

Conditions
ConditionsYield
With phosphoric acid In water at 20℃; for 12.5h;98.6%

2-Oxohexamethylenimine Consensus Reports

CAPROLACTAM  is reported in EPA TSCA Inventory.Caprolactam was included on the list of hazardous air pollutants to be controlled under the Clean Air Act of 1990. It was subsequently removed from the list in 1993.

2-Oxohexamethylenimine Standards and Recommendations

OSHA PEL: Dust: 1 mg/m3; STEL 3 mg/m3; Vapor: 5 ppm; STEL 10 ppm
ACGIH TLV: TWA (aerosol and vapor) 5 mg/m3; Not Suspected as a Human Carcinogen
DFG MAK: 5 mg/m3
NIOSH REL: (Caprolactam, dust) TWA 1 mg/m3; STEL 3 mg/m3; (Caprolactam, vapor) TWA 0.22 ppm; STEL 0.66 ppm

2-Oxohexamethylenimine Specification

The Caprolactam, with the cas registry number 105-60-2, has the IUPAC name of azepan-2-one. This is a kind of white flake or molten mass, and it is soluble in water, chlorinated solvent, petroleum hydrocarbon, cyclohexene, benzene, methyl alcohol, ethanol and diethyl [ethyl] ether. Its product categories are including pharmaceutical intermediates; highly purified reagents; other categories; zone refined products.

The characteristics of this chemical are as follows: (1)ACD/LogP: -0.32; (2)ACD/LogD (pH 5.5): -0.32; (3)ACD/LogD (pH 7.4): -0.32; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 15.87; (7)ACD/KOC (pH 7.4): 15.87; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Polar Surface Area: 20.31; (11)Index of Refraction: 1.446; (12)Molar Refractivity: 31.14 cm3; (13)Molar Volume: 116.7 cm3; (14)Polarizability: 12.34 ×10-24 cm3; (15)Surface Tension: 30.4 dyne/cm; (16)Density: 0.969 g/cm3; (17)Flash Point: 136.7 °C; (18)Enthalpy of Vaporization: 51.08 kJ/mol; (19)Boiling Point: 272.5 °C at 760 mmHg; (20)Vapour Pressure: 0.00607 mmHg at 25°C.

The production method is as below: 1-azido-1-methylsulfanyl-cyclohexane could react to produce  Caprolactam, with the following condition: reagent: trifluoroacetic acid; solution: CHCl3; reation time: 2 hours; reaction temp.: 25 ℃; yield: 79%.

Use of Caprolactam is as below: Caprolactam could react with methanol to produce ch7-methoxy-azepan-2-one, with the following condition: yield: 94%; other condition: methoxylation by anodic oxidation (C rods, (C2H5)4NOTs).

As to its usage, it is widely applied in many ways. It could be used in producing polycaprolactam, synthetic fibre (KaprOn); It could also be used in making wheel gear, bearing, tubular product, medical apparatus and instruments and others. Besides, it could be applied in painting, stabilizer for plastics, in composing lysine, and also in pharmaceutic material.

When dealing with this chemical, you should be cautious. This is irritating to eyes, respiratory system and skin. Besides, being a kind of harmful chemical, it may cause damage to health. And if by inhalation and if swallowed, it will be very harmful. Therefore, while keeping, keep out of the reach of children.

Additionally, the following data information could be converted into the molecular structure:
(1)SMILES:O=C1NCCCCC1
(2)InChI:InChI=1/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8)
(3)InChIKey:JBKVHLHDHHXQEQ-UHFFFAOYAF

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo subcutaneous 2800mg/kg (2800mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 50, Pg. 199, 1903.
guinea pig LDLo subcutaneous 950mg/kg (950mg/kg)   Medicina del Lavoro. Industrial Medicine. Vol. 43, Pg. 124, 1952.
 
human TCLo inhalation 100ppm (100ppm) LUNGS, THORAX, OR RESPIRATION: COUGH American Industrial Hygiene Association Journal. Vol. 34, Pg. 384, 1973.
 
mouse LC50 inhalation 450mg/m3 (450mg/m3) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 10(10), Pg. 54, 1966.
mouse LD50 intraperitoneal 650mg/kg (650mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ANALGESIA

BEHAVIORAL: ANTIPSYCHOTIC		 Journal of Pharmaceutical Sciences. Vol. 60, Pg. 1058, 1971.
 
mouse LD50 intravenous 480mg/kg (480mg/kg)   IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. Vol. 39, Pg. 247, 1986.
 
mouse LD50 oral 930mg/kg (930mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 10(10), Pg. 54, 1966.
mouse LD50 subcutaneous 750mg/kg (750mg/kg)   IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. Vol. 39, Pg. 247, 1986.
 
mouse LD50 unreported 930mg/kg (930mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED		 Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(10), Pg. 33, 1990.
rabbit LD intravenous > 300mg/kg (300mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS		 British Journal of Industrial Medicine. Vol. 11, Pg. 1, 1954.
 
rabbit LD50 skin 1410uL/kg (1.41mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
 
rabbit LD50 unreported 1gm/kg (1000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED		 Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(10), Pg. 33, 1990.
rat LC50 inhalation 300mg/m3/2H (300mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 32, 1982.
rat LD50 oral 1210mg/kg (1210mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHROMODACYRORREA: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 National Toxicology Program Technical Report Series. Vol. NTP-TR-214, Pg. 1982,
rat LD50 skin > 2gm/kg (2000mg/kg)   National Technical Information Service. Vol. OTS0557720,
rat LD50 unreported 580mg/kg (580mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED		 Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(10), Pg. 33, 1990.
rat LDLo intraperitoneal 800mg/kg (800mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS		 British Journal of Industrial Medicine. Vol. 11, Pg. 1, 1954.
 

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