Caprolactam

Base Information

• Chemical Name: Caprolactam
• CAS No.: 105-60-2
• Deprecated CAS: 117955-36-9,168214-28-6,2953-03-9,32838-21-4,32838-23-6,34876-18-1,168214-28-6,2953-03-9,32838-21-4,34876-18-1
• Molecular Formula: C6H11NO
• Molecular Weight: 113.159
• Hs Code.: 2933710000
• European Community (EC) Number: 919-537-5
• ICSC Number: 0118
• NSC Number: 117393,25536,4977
• UN Number: 3082
• UNII: 6879X594Z8
• DSSTox Substance ID: DTXSID4020240
• Nikkaji Number: J3.605F
• Wikipedia: Caprolactam
• Wikidata: Q409397
• Metabolomics Workbench ID: 51773
• ChEMBL ID: CHEMBL276218
• Mol file: 105-60-2.mol

Synonyms:Aminocaproic Lactam;Caprolactam;Hexahydro 2H Azepin 2 One;Hexahydro-2H-Azepin-2-One;Lactam, Aminocaproic

Chemical Property of Caprolactam

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 0.00607mmHg at 25°C
• Melting Point: 68-71 °C(lit.)
• Refractive Index: 1.4935
• Boiling Point: 272.5 °C at 760 mmHg
• PKA: 16.61±0.20(Predicted)
• Flash Point: 136.7 °C
• PSA: 29.10000
• Density: 1.01 g/cm³
• LogP: 1.00540
• Water Solubility.: 4560 g/L (20℃)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 113.084063974
• Heavy Atom Count: 8
• Complexity: 90.5

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: R20/22:; R36/37/38:
• Safety Statements: S2:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Other Monomers
• Canonical SMILES: C1CCC(=O)NCC1
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the skin, eyes and respiratory tract. The substance may cause effects on the central nervous system.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the nervous system and liver.

Technology Process of Caprolactam

There total 286 articles about Caprolactam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.2%

14,15-dioxa-7-aza-dispiro[5.1.5.2]pentadecane (21842-28-4) → caprolactam (105-60-2,9012-16-2) + 11-cyanoundecanoic acid (5810-18-4) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4)

Guidance literature:

With cerium(IV) oxide; 2,2'-azobis(isobutyronitrile); at 50 ℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield: 99.0%

methyl 6-oxohexanoate (6654-36-0) → caprolactam (105-60-2,9012-16-2) + poly(6-aminocaproamide-co-6-aminocaproic acid) + 6-aminocaproic amide (373-04-6) + methyl 6-aminohexanoate hydrochloride (2780-89-4) + 6-aminohexanoic acid (60-32-2,93208-38-9)

Guidance literature:

methyl 6-oxohexanoate; With ammonia; In methanol; water; at 35 ℃; for 0.00416667h; under 22502.3 Torr;

With hydrogen; 5 % ruthenium on Al2O3; In methanol; water; at 120 ℃; for 22h; under 22502.3 Torr;

Reference yield: 99.0%

caprolactam; 6-aminocaproic acid; 6-aminocaproic amide; nylon-6-oligomers; water; mixture of → caprolactam (105-60-2,9012-16-2) + pentamide (626-97-1) + 5-hexenoic acid (1577-22-6) + hexanoic acid (142-62-1) + valeric acid (109-52-4)

Guidance literature:

at 300 ℃; for 5h; under 9000.9 Torr;

upstream raw materials:

N-Bromosuccinimide

cyclohexanone-oxime

Adipic acid

6-Hydroxyhexanoic acid

Downstream raw materials:

N-acetyl-ε-aminocapramide

N-[(Z)-3-Oxo-1-(2-oxo-azepan-3-yl)-but-1-enyl]-benzamide

N-(But-1-yl)-ε-caprolactam

1-ethylhexahydro-2H-azepin-2-one

Refernces

• 1、 Sato, Satoshi,Sakurai, Hiroaki,Urabe, Kazuo,Izumi, Yusuke. "VAPOR-PHASE BECKMANN REARRANGEMENT OF CYCLOHEXANONE OXIME OVER SILICA-BORIA CATALYST PREPARED BY CHEMICAL VAPOR DEPOSITION METHOD". . p. 277 - 278. Retrieved 1985.
• 2、 Prasad,Vashisht, Seema. "Ammoximation of cyclohexanone by nitric oxide and ammonia: A One-step process for synthesis of polycaprolactam". . p. 373 - 376. Retrieved 1996.
• 3、 Sarak, Sharad,Sung, Sihyong,Jeon, Hyunwoo,Patil, Mahesh D.,Khobragade, Taresh P.,Pagar, Amol D.,Dawson, Philip E.,Yun, Hyungdon. "An Integrated Cofactor/Co-Product Recycling Cascade for the Biosynthesis of Nylon Monomers from Cycloalkylamines". . p. 3481 - 3486. Retrieved 2021.
• 4、 Kelly,Matthews. "-". . p. 2159. Retrieved 1971.
• 5、 Kobayashi. "-". . p. 3467,3470. Retrieved 1973.
• 6、 Kita, Yusuke,Numajiri, Yoshitaka,Okamoto, Noriko,Stoltz, Brian M.. "Construction of tertiary chiral centers by Pd-catalyzed asymmetric allylic alkylation of prochiral enolate equivalents". . p. 6349 - 6353. Retrieved 2015.
• 7、 Liu, Pingle,Xie, Huan,You, Kuiyi,Hao, Fang,Li, Xiaofeng,Luo, He'An. "Preparation of SiO2-Al2O3 and its supported Co3O4 Catalysts for nitrosation of cyclohexane". . p. 150 - 154. Retrieved 2010.
• 8、 Yin, Jie,Wildeman, Jur,Loontjens, Ton. "Lysine-based functional blocked isocyanates for the preparation of polyurethanes provided with pendant side groups". . p. 2036 - 2049. Retrieved 2015.
• 9、 Drouin, Alexandre,Lessard, Jean. "Ring contraction of N-chlorolactams, a novel rearrangement". . p. 4285 - 4288. Retrieved 2006.
• 10、 Xu, Changhai,Hinks, David,Sun, Chang,Wei, Qufu. "Establishment of an activated peroxide system for low-temperature cotton bleaching using N-[4-(triethylammoniomethyl)benzoyl]butyrolactam chloride". . p. 71 - 77. Retrieved 2015.