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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2271228Generated: November 1, 2026

Ammonia → Caprolactam

https://huagongshe.com/reaction/2271228

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantMethyl 6-oxohexanoateHCID 81164—
ReactantHCID 178418361HCID 178418361—
SolventMethanolHCID 887—
ProductCaprolactamHCID 7768—
ProductMethyl 6-aminohexanoateHCID 1810164—

Reaction Steps

Such a process is described in U.S. Pat. No. 4,731,445. This publication describes a process in which first methyl 5-formylvalerate is contacted with ammonia and hydrogen in the presence of methanol as solvent and a hydrogenation catalyst. In this step methyl 6-aminocaproate and a small amount of ε-caprolactam is obtained. In a second step, the excess ammonia and hydrogen are removed from the reaction mixture. In a third step, the methyl 6-aminocaproate is reacted with water in the presence of a small amount (0.1 to 2 wt. %) of ammonia at a temperature of 50 to 250 ° C. The released methanol is simultaneously removed. Example 1 of U.S. Pat. No. 4,731,445 discloses the reaction of methyl 6-aminocaproate with water in the presence of an almost negligible amount of ammonia at a temperature of about 100° C. The resulting aqueous mixture, which mixture contains 6-aminocaproic acid and small amounts of 6-minocaproamide and ε-caprolactam, is heated to a emperature of 330° C. In this step the 6-aminocaproic acid and 6-aminocaproamide reacts by cyclization to ε-caprolactam.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06333412B1
Source datasetuspto-grants-2001_12
ORD IDord-0c4f98ac782a4c91b1e9575b625b646a
Source noteuspto-grants-2001_12