IP Library Granted Patent US 11,618,732
Granted Patent B2
US 11,618,732 · App. 17/115,396 · Granted Apr 4, 2023

Process for the synthesis of n-substituted lactams and amides

Inventors: Xiawei Zhang (West Chester, PA); Robert Schutter, Jr. (Sewell, NJ); Lihao Tang (Bridgewater, NJ); Scott Keenan (Marlton, NJ); Xin Li (Broomall, PA)
Assignee: AdvanSix Resins & Chemical LLC
C07D223/04B01J23/44
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Quick Facts
Patent No.
US 11,618,732
App. No.
17/115,396
Granted
Apr 4, 2023
Kind
B2
Abstract

A process for the synthesis of N-alkylated lactams via reductive alkylation. The process of the present disclosure may be conducted by the addition of an aldehyde to a lactam in the presence of a catalyst under a reducing atmosphere.

Claims (14)

1. A process for preparing a substituted lactam, comprising:

reacting caprolactam with an alkylating agent selected from paraformaldehyde, formaldehyde, and acetaldehyde;

in the presence of:

a catalyst;

hydrogen; and

optionally, process solvents, a total content of the process solvents of less than 1500 ppm,

to form water and an N-substituted lactam selected from the group consisting of N-methylcaprolactam and N-ethylcaprolactam.

2. The process of claim 1 , wherein the total content of process solvents is less than 1000 ppm.

3. The process of claim 1 , wherein the catalyst is a palladium catalyst.

4. The process of claim 1 , wherein the reacting step is carried out at a temperature from 50° C. to 200° C.

5. The process of claim 1 , wherein the reacting step is carried out in the presence of a hydrogen atmosphere at a pressure of 100 to 200 psi.

6. The process of claim 1 , wherein the N-substituted lactam is N-methylcaprolactam.

7. The process of claim 1 , wherein the N-substituted lactam is N-ethylcaprolactam.

8. The process of claim 1 , wherein the N-substituted lactam is obtained at a yield of greater than 90%.

Assignments (1)
SECURITY INTEREST Recorded Oct 27, 2021
From: ADVANSIX INC.; ADVANSIX RESINS & CHEMICALS LLC
To: TRUIST BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 057940/0794 →
Continuity (2)
Provisional Application 62946591 · Dec 11, 2019
Related Publication 20210179562A1 · Jun 17, 2021