Laurolactam preparation method and synthesis apparatus

Patent metadata

Field	Value
Publication number	US-11535591-B2
Application number	US-201917311353-A
Country	US
Kind code	B2
Filing date	Dec 18, 2019
Priority date	Dec 19, 2018
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

The present invention relates to a laurolactam preparation method and synthesis apparatus, and epoxidation and a rearrangement reaction are performed in the conversion of cyclododecene into cyclododecanone so that the preparation method can synthesize laurolactam having a higher purity with a higher selectivity and in a higher yield than a conventional preparation method.

First claim

The invention claimed is:

1. A laurolactam preparation method, comprising:
a) synthesizing epoxidized cyclododecane by epoxidizing cyclododecene (CDEN) with a catalyst;
b) synthesizing cyclododecanone by catalyzing the epoxidized cyclododecane; and
c) synthesizing cyclododecanone oxime by performing ammoximation on the cyclododecanone.

2. The laurolactam preparation method of claim 1 , further comprising, before the step a), synthesizing cyclododecene (CDEN) by performing a partial hydrogenation reaction on cyclododecatriene (CDT).

3. The laurolactam preparation method of claim 2 , wherein the cyclododecatriene (CDT) is synthesized by performing a cyclotrimerization reaction on 1, 3-butadiene with a Ziegler-Natta catalyst.

4. The laurolactam preparation method of claim 2 , wherein the partial hydrogenation reaction is performed through a stirrer in which a negative pressure and a positive pressure are generated by stirring.

5. The laurolactam preparation method of claim 2 , wherein the partial hydrogenation reaction is performed in the presence of a homogeneous catalyst containing ruthenium chloride, triphenyl phosphine, and formaldehyde or carbon monoxide complex.

6. The laurolactam preparation method of claim 1 , wherein the step a) is epoxidized using a catalyst containing a tungsten oxide salt and a phase transfer agent.

7. The laurolactam preparation method of claim 1 , wherein the step b) is performed in the presence of an alkali halide as a catalyst.

8. The laurolactam preparation method of claim 1 , wherein in the step c), the cyclododecanone oxime is synthesized by reacting ammonia; hydrogen peroxide; a catalyst containing titanium silicalite; and a reaction activator containing ammonium acetate with cyclododecanone in a solvent containing ethanol.

9. The laurolactam preparation method of claim 1 , further comprising, after the step c), d) synthesizing laurolactam by performing a Beckmann rearrangement reaction on the cyclododecanone oxime.

10. The laurolactam preparation method of claim 9 , wherein the Beckman rearrangement reaction synthesizes laurolactam from cyclododecanone oxime through a catalyst containing cyanuric chloride in a solvent containing isopropylcyclohexane.

11. The laurolactam preparation method of claim 9 , further comprising, after the step d) of synthesizing laurolactam, e) separating and purifying the laurolactam from a mixture containing the laurolactam.

Assignees

• Hanwha Solutions Corp
• Doosan Enerbility Co Ltd

Inventors

• Kim Jiyeon
• Kim Youngjin
• Park Jeongseok
• Park Jinho
• Seo Hyun
• Hyeong Seonghoon
• Song Kyuho

Classifications

• C07C49/307

  to a seven- to twelve-membered ring · CPC title

• C07C249/04 Primary

  of oximes · CPC title

• C07C45/58

  in three-membered rings · CPC title

• C07D225/02

  not condensed with other rings · CPC title

• C07C13/273

  with a twelve-membered ring · CPC title