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105-60-2

Basic Information
CAS No.: 105-60-2
Name: 6-Caprolactam
Article Data: 439
Molecular Structure:
Molecular Structure of 105-60-2 (6-Caprolactam)
Formula: C6H11NO
Molecular Weight: 113.159
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;
EINECS: 203-313-2
Density: 1.01 g/cm3
Melting Point: 68-71 °C(lit.)
Boiling Point: 272.5 °C at 760 mmHg
Flash Point: 136.7 °C
Solubility: 4560 g/L (20 °C) in water
Appearance: white crystalline solid
Hazard Symbols: HarmfulXn
Risk Codes: 20/22-36/37/38
Safety: 2
Transport Information: UN 2811 6.1/PG 2
PSA: 29.10000
LogP: 1.00540
Synthetic route
100-64-1

Cyclohexanone oxime

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%
19494-73-6

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

1760-24-3

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

A

105-60-2

caprolactam

B

C15H31N3O5Si

Conditions
ConditionsYield
In toluene at 75℃; for 3h;A n/a
B 100%
13822-56-5

3-(trimethoxysilyl)propan-1-amine

19494-73-6

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

A

105-60-2

caprolactam

B

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

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

Cyclohexanone oxime

77-78-1

dimethyl sulfate

105-60-2

caprolactam

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

Cyclohexanone oxime

106-89-8

epichlorohydrin

105-60-2

caprolactam

Conditions
ConditionsYield
In N,N-dimethyl-formamide99.5%
21842-28-4

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

A

105-60-2

caprolactam

B

5810-18-4

11-cyanoundecanoic acid

C

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
2432-74-8

1-amino-5-cyanopentane

105-60-2

caprolactam

Conditions
ConditionsYield
99.1%
99%
98.9%
60-32-2

6-aminohexanoic acid

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%
6654-36-0

methyl 6-oxohexanoate

A

105-60-2

caprolactam

B

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

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

C

373-04-6

6-aminocaproic amide

D

2780-89-4

methyl 6-aminohexanoate hydrochloride

E

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

105-60-2

caprolactam

B

626-97-1

pentamide

C

1577-22-6

5-hexenoic acid

D

142-62-1

hexanoic acid

E

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
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    Caprolactam

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    Product Description Product Name: Caprolactam CAS: 105-60-2 MF: C6H11NO MW: 113.16 EINECS: 203-313-2 Product Categories: Pharmaceutical Intermediates;Highly Purified Reagents;Other Categories;Zone Refined Products Mol File: 105-60-2.mol Melti

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    Caprolactam

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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.

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

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.