6-Aminohexanoic acid lactam

Aminohexanoic Acid Lactam tert- Amyl Alcohol ... 

Aminohexanoic acid lactam (s-caprolactam) is obtained in two steps starting from cyclohexanone. The ketone is converted into an oxime. Then, the oxime is converted into -caprolactam by tteatment with sulfuric acid. The second step, called the Beckmann rearrangement, proceeds through a series of cationic intermediates and a skeletal rearrangement. 

Caprolactam (5.68, Fig. 5.21) has a seven-membered lactam ring and is a major industrial compound in the production of Nylon , its polymer. This compound shows only moderate levels of toxicity in mice and rats when administered orally. The hydrolysis product 6-aminohexanoic acid (5.69) was a minor metabolite in rats [176]. Hydroxylation in the y-position to yield 5.70 without preliminary hydrolysis of the lactam linkage has been shown to be the major metabolic pathway. This metabolite hydrolyzes in urine to produce 6-amino-4-hydroxyhexanoic acid (5.71), which is in equilibrium with the corresponding lactone (5.72). 

Caprolactam or (hexahydroazepin-2-one) is, without doubt, the most important azepine derivative. This seven-membered lactam is produced in vast quantities as an intermediate for the manufacture of nylon 6 (B-75MI51601, B-70MI51601). Polymerization, which is carried out at high temperatures with water as the initiator or at low temperatures with a strong base (e.g. NaH), proceeds by attack at the caprolactam carbonyl by the amino function of the open-chain monomer, e -aminohexanoic acid. 

A soln of lactam 11611751 (R = R3 = Me R2 = R4=H 200mg, 1.42mmol) in coned HC1 (2mL) and H20 (6mL) was maintained at gentle reflux for 5h. The solvent was removed under reduced pressure to afford crude 3,5-dimethylaminohexanoic acid (not characterized). SOCl2 (1 mL) was added to MeOH (4mL) at 0°C and stirred for 20 min. To this soln at 0°C was added the crude aminohexanoic acid in MeOH (4mL), and the mixture was stirred overnight at rt. The solvent was then removed under reduced pressure to afford methyl (3R,5S)-6-amino-3,5-dimethyI hexanoate hydrochloride. 

Nylon 6 is another polyamide, which is made by heating an aqueous solution of e-caprolactam. The seven-membered ring of the lactam is opened to form 6-aminohexanoic acid, the monomer that reacts with more lactam to form the polyamide chain. This step-growth polymerization thus begins with a single difunctional monomer that has two different functional groups, NH2 and COOH. 

CAS 105-60-2 EINECS/ELINCS 203-313-2 Synonyms /tminocaproic lactam 6-Aminohexanoic acid cyclic lactam 2-/tzacyclophetanone 6-Caprolactam e-Caprolactam Cyclohexanone iso-oxime Hexahydro-2-azepinone Hexahydro-2H-azepin-2-one 6-Hexanelactam Hexanoneisoxime 1,6-Hexolactam 2-Ketohexameth-ylenimine 2-Oxohexamethyleneimine 2-Oxohexamethylenimine 2-Perhydroazepinone Classification Lactam Empirical CsHnNO Formula (CHJsNH CO... 

Nylon 6 is normally prepared from the lactam derived from 6-aminohexanoic acid, called 8-caprolactam. Do you remember what a lactam is Write the structure of e-caprolactam. 

CAS 105-60-2 EINECS/ELINCS 203-313-2 Synonyms Aminocaproic lactam 6-Aminohexanoic acid cyclic lactam 2-Azacyclophetanone 6-Caprolactam c-Caprolactam... 

Another important method for the preparation of amino acids involves direct cleavage of a cyclic ketone. In section 2.1.A, a lactam product (a cyclic amide) was produced from the ketone and then cleaved by hydrolysis, but in this section the ketone moiety is cleaved directly. A cyclic ketone such as cyclopentanone can be oxidatively cleaved with sulfuric acid. When this cleavage was followed by treatment with nitrosyl sulfate, an oximino acid 2.11) was formed. Catalytic hydrogenation of the oximino group gave 4-aminobutanoic acid (2.72). Similar treatment of cycloheptanone gave 6-aminohexanoic acid (2.75) and cyclononanone led to 8-aminooctanoic acid. ... 

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