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6-Caprolactam, a colorless organic compound with a slightly sweet odor, is a cyclic compound that consists of a six-membered lactam ring. It is commonly used in the manufacturing of synthetic fibers and resins, most notably in the production of nylon 6, a versatile, water-resistant material often used in textiles. Produced on a large scale from cyclohexanone, the process involves the conversion of cyclohexanone to oxime followed by a Beckmann rearrangement. Although it is considered to have low acute toxicity, chronic exposure can lead to skin, eye, and respiratory irritations.

105-60-2

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105-60-2 Usage

Uses

Used in Textile Industry:
6-Caprolactam is used as a raw material for the production of nylon 6, a synthetic fiber known for its water resistance and versatility, making it suitable for various textile applications.
Used in Plastics and Resins Industry:
6-Caprolactam is used as a monomer in the synthesis of nylon 6, which is then used to produce a wide range of plastics and resins with diverse applications in various industries.
Used in Chemical Production:
6-Caprolactam is used as an intermediate in the production of other chemicals, taking advantage of its reactive lactam ring for further chemical transformations.

Check Digit Verification of cas no

The CAS Registry Mumber 105-60-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 5 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 105-60:
(5*1)+(4*0)+(3*5)+(2*6)+(1*0)=32
32 % 10 = 2
So 105-60-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8)

105-60-2 Well-known Company Product Price

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  • Alfa Aesar

  • (L06999)  epsilon-Caprolactam, 99%   

  • 105-60-2

  • 100g

  • 116.0CNY

  • Detail
  • Alfa Aesar

  • (L06999)  epsilon-Caprolactam, 99%   

  • 105-60-2

  • 500g

  • 173.0CNY

  • Detail
  • Alfa Aesar

  • (L06999)  epsilon-Caprolactam, 99%   

  • 105-60-2

  • 2500g

  • 550.0CNY

  • Detail
  • Aldrich

  • (C2204)  ε-Caprolactam  99%

  • 105-60-2

  • C2204-5G

  • 269.10CNY

  • Detail
  • Aldrich

  • (C2204)  ε-Caprolactam  99%

  • 105-60-2

  • C2204-250G

  • 322.92CNY

  • Detail
  • Aldrich

  • (C2204)  ε-Caprolactam  99%

  • 105-60-2

  • C2204-1KG

  • 437.58CNY

  • Detail

105-60-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name ε-caprolactam

1.2 Other means of identification

Product number -
Other names PA 6

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:105-60-2 SDS

105-60-2Synthetic 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%
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%
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
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
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
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%
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;
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;
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%
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%
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;
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
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%
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

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
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%
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%

105-60-2Relevant articles and documents

Hierarchical silicalite-1 octahedra comprising highly-branched orthogonally-stacked nanoplates as efficient catalysts for vapor-phase Beckmann rearrangement

Chang, Albert,Hsiao, Hsu-Ming,Chen, Tsai-Hsiu,Chu, Ming-Wen,Yang, Chia-Min

, p. 11939 - 11942 (2016)

A triblock structure-directing agent was designed to synthesize hierarchical silicalite-1 octahedra comprising highly-branched, orthogonally-stacked and self-pillared nanoplates that exhibited excellent and stable activity for the vapor-phase Beckmann rearrangement of cyclic oximes and high lactam selectivity.

VAPOR-PHASE BECKMANN REARRANGEMENT OF CYCLOHEXANONE OXIME OVER SILICA-BORIA CATALYST PREPARED BY CHEMICAL VAPOR DEPOSITION METHOD

Sato, Satoshi,Sakurai, Hiroaki,Urabe, Kazuo,Izumi, Yusuke

, p. 277 - 278 (1985)

Cyclohexanone oxime was converted to ε-caprolactam in a high yield of 93percent at 250 deg over a silica-supported boron oxide catalyst which was prepared by means of chemical vapor deposition.This catalyst was much more efficient than silica-boria and alumina-boria which were obtained by the usual impregnation method.

Active Sites for the Liquid-Phase Beckmann Rearrangement of Cyclohexanone, Acetophenone and Cyclododecanone Oximes, Catalyzed by Beta Zeolites

Camblor,Corma,Garcia,Semmer-Herledan,Valencia

, p. 267 - 272 (1998)

The Beckmann rearrangement of oximes with different molecular sizes, i.e. cyclohexanone, cyclododecanone, and acetophenone oximes, has been studied in liquid phase at 130°C over a series of four Beta zeolites differing in the presence or absence of framework Al and internal silanol groups. When the zeolite does not contain framework Al and internal silanols, no appreciable conversion was observed. The catalyst having internal silanol groups but no framework Al exhibits oxime conversion, but the selectivity to the corresponding amide is low in some cases. In the Beta zeolite without silanol groups but containing framework Al, conversion and selectivity were found to be very high. This superior performance of Broensted acid sites, compared to silanol groups, shows that the results reported for the vapor phase reaction cannot be extrapolated when the reaction is performed in liquid phase. Finally, as could be anticipated according to the dimensions of the micropores, it is shown that H-Beta zeolites exhibit a much better catalytic performance than H-ZSM-5 zeolite for larger sized oximes.

Ammoximation of cyclohexanone by nitric oxide and ammonia: A One-step process for synthesis of polycaprolactam

Prasad,Vashisht, Seema

, p. 373 - 376 (1996)

Catalytic transformation of cyclohexanone by nitric oxide and ammonia to cyclohexanone oxime, its rearrangement to caprolactam, and its polymerization to polycaprolactam has been studied in the liquid phase over solid catalysts. The influence of various catalysts and process parameters on the oximation reaction is reported. A maximum yield of 37.78% with a selectivity of 80.95% for caprolactam could be achieved, over a synthetically prepared Al2O3-SiO2 catalyst, at a cyclohexanone : NO : NH3 molar ratio of 1:2.9:1.7 and a temperature of 348 K. In this process the production of oxime and its rearrangement to caprolactam occur simultaneously. The resulting caprolactam polymerises later to give a molecular weight ranging from 500 to 5000. A tentative mechanism for the reactions is suggested.

Porous aluminosilicate inorganic polymers (geopolymers): a new class of environmentally benign heterogeneous solid acid catalysts

Alzeer, Mohammad I.M.,MacKenzie, Kenneth J.D.,Keyzers, Robert A.

, p. 173 - 181 (2016)

Aluminosilicate inorganic polymers (geopolymers) were developed as a new class of cost-efficient, environmentally friendly, solid acid catalysts and their performance evaluated in a model liquid-phase Beckmann rearrangement reaction (cyclohexanone oxime to ε-caprolactam). The active sites were generated within the structure of the geopolymers by ion-exchange with NH4+ followed by thermal treatment. The effect of varying the starting composition on the textural and acidic properties of the geopolymer catalysts was studied and its influence on the catalytic activity was investigated. Catalytic performance was significantly improved by the use of post-synthetic treatments. No significant decrease in the yield of ε-caprolactam after recycling for five times suggesting that geopolymer-based catalysts are advantageous over supported catalysts which often lose their catalytic activity due to leaching of the active sites from the support. The catalytic activities obtained in this study are comparable, and sometimes superior, to other solid catalysts suggesting that geopolymers have a great potential as environmentally benign heterogeneous catalysts.

An Integrated Cofactor/Co-Product Recycling Cascade for the Biosynthesis of Nylon Monomers from Cycloalkylamines

Sarak, Sharad,Sung, Sihyong,Jeon, Hyunwoo,Patil, Mahesh D.,Khobragade, Taresh P.,Pagar, Amol D.,Dawson, Philip E.,Yun, Hyungdon

, p. 3481 - 3486 (2021)

We report a highly atom-efficient integrated cofactor/co-product recycling cascade employing cycloalkylamines as multifaceted starting materials for the synthesis of nylon building blocks. Reactions using E. coli whole cells as well as purified enzymes produced excellent conversions ranging from >80 and 95 % into desired ω-amino acids, respectively with varying substrate concentrations. The applicability of this tandem biocatalytic cascade was demonstrated to produce the corresponding lactams by employing engineered biocatalysts. For instance, ?-caprolactam, a valuable polymer building block was synthesized with 75 % conversion from 10 mM cyclohexylamine by employing whole-cell biocatalysts. This cascade could be an alternative for bio-based production of ω-amino acids and corresponding lactam compounds.

Amino-alcohol cyclization: Selective synthesis of lactams and cyclic amines from amino-alcohols

Pingen, Dennis,Vogt, Dieter

, p. 47 - 52 (2014)

By employing an amination catalyst, previously used in the direct synthesis of amines from alcohol with ammonia, n-amino-alcohols could be selectively cyclized to either the amide or the amine. By the addition of water, the amine could be produced as the major product whereas adding a sacrificial ketone as a hydrogen acceptor resulted in the amide as the major product. Without an additive a mixture of both the amine and the amide was observed. N-substituted amino-alcohols solely gave cyclic amines under these conditions. From 2-(n-alkanol) anilines the cyclic amines were produced, where the n-propanol derivative selectively formed quinoline as the major product.

Catalytic properties of WOx/SBA-15 for vapor-phase Beckmann rearrangement of cyclohexanone oxime

Bordoloi, Ankur,Halligudi

, p. 141 - 147 (2010)

WOx/SBA-15 nanocomposite materials with different WOx loadings were prepared by one step hydrothermal synthesis and used in the vapor-phase Beckmann rearrangement of cyclohexanone oxime to ε-caprolactam. The catalysts were thoroughly characterized by X-ray diffraction (XRD), sorption analysis, energy dispersive X-ray analysis (EDAX) and Raman spectroscopy. The acidities of the catalysts were estimated by ammonia temperature programmed desorption (NH3-TPD) and Fourier transform infrared studies of adsorbed pyridine (pyridine-FTIR). The optimum temperature for the Beckmann rearrangement was 350 °C. Using WOx/SBA-15(20) under the vapor-phase reaction conditions [temperature = 350 °C, WHSV = 0.6 h-1, oxime concentration = 2.5% (w/w) in MeOH] gave 79% cyclohexanone oxime conversion with 93%, ε-caprolactam selectivity. The ε-caprolactam selectivity was found to be dependent on temperature and space velocity. A correlation has been made between the rearrangement activity and acidity and the structural properties of the catalysts.

Weil-defined N-heterocyclic carbene based ruthenium catalysts for direct amide synthesis from alcohols and amines

Zhang, Yao,Chen, Cheng,Ghosh, Subhash Chandra,Li, Yongxin,Hong, Soon Hyeok

, p. 1374 - 1378 (2010)

Well-defined N-heterocyclic carbene based ruthenium, complexes were developed as highly active catalysts for direct amide synthesis from alcohols and amines. A catalytic amount of a base such, as KO1Bu was essential to initiate the catalytic cycle. Activity of the Ru complexes was comparable with the reported in situ Ru catalysts. These catalysts provided mechanistic insight suggesting a Ru hydride species as an active catalytic intermediate. The generation of the Ru hydride was critical for the amidation of free aldehydes.

Construction of tertiary chiral centers by Pd-catalyzed asymmetric allylic alkylation of prochiral enolate equivalents

Kita, Yusuke,Numajiri, Yoshitaka,Okamoto, Noriko,Stoltz, Brian M.

, p. 6349 - 6353 (2015)

Abstract The palladium-catalyzed decarboxylative allylic alkylation of enol carbonates derived from lactams and ketones is described. Employing these substrates with an electronically tuned Pd catalyst system trisubstituted chiral centers are produced. These stereocenters have been previously challenging to achieve using Pd complex/chiral P-N ligand systems.

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