Method for manufacturing cyclododecanone

Patent metadata

Field	Value
Publication number	US-11358923-B2
Application number	US-201917298921-A
Country	US
Kind code	B2
Filing date	Sep 16, 2019
Priority date	Dec 19, 2018
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

The present invention relates to a method of preparing cyclododecanone. According to the present invention, a method of preparing cyclododecanone which allows implementation of a high conversion rate and minimization of production of unreacted materials and reaction by-products may be provided. In addition, the present invention implements a high conversion rate and a high selectivity even by a simplified process configuration, and thus may be usefully utilized in an economical method of preparing laurolactam, allowing commercially easy mass production.

First claim

The invention claimed is:

1. A method of preparing cyclododecanone, the method comprising: applying heat while additionally injecting hydrogen peroxide to a mixture of cyclododecene and hydrogen peroxide under a catalyst system including a tungsten compound, a phosphoric acid compound, and an amine compound to prepare epoxidized cyclododecane; and preparing cyclododecanone by a rearrangement reaction without separation of a reaction mixture including the epoxidized cyclododecane under an alkaline metal halide catalyst,
wherein the hydrogen peroxide additionally injected is injected is injected so that the following relation formula is satisfied:
50≤ In f ≤150

1.0≤ In m ≤3.0  [Relation Formula]

wherein In f is an injection flow rate per minute (μl/min) of the hydrogen peroxide additionally injected based on a 0.1 L reactor, and
In m is a mole ratio (B/A) between cyclododecene (A) and hydrogen peroxide additionally injected (B).

2. The method of preparing cyclododecanone of claim 1 , wherein the mixture includes substantially no cyclododecane.

3. The method of preparing cyclododecanone of claim 1 , wherein 1 to 10 parts by weight of the hydrogen peroxide is mixed, based on 100 parts by weight of the cyclododecene.

4. The method of preparing cyclododecanone of claim 1 , wherein the tungsten compound is a tungstic acid, a tungstate salt, or a mixture thereof.

5. The method of preparing cyclododecanone of claim 1 , wherein the phosphoric acid compound is an inorganic phosphoric acid, an inorganic phosphate salt, an organic phosphoric acid, or a mixture thereof.

6. The method of preparing cyclododecanone of claim 1 , wherein the amine compound is a tertiary amine, a quaternary ammonium salt, and a mixture thereof.

7. The method of preparing cyclododecanone of claim 1 , wherein 0.001 to 10 parts by weight of the catalyst system is included, based on 100 parts by weight of the cyclododecene.

8. The method of preparing cyclododecanone of claim 7 , wherein in the catalyst system, the tungsten compound (a), the phosphoric acid compound (a), and the amine compound (c) are mixed at a weight ratio of 1:0.1 to 2.0:0.1 to 5.0.

9. The method of preparing cyclododecanone of claim 1 , wherein the preparing of epoxidized cyclododecane is performed under a temperature condition of 50 to 120° C.

10. The method of preparing cyclododecanone of claim 1 , wherein the rearrangement reaction is performed without a solvent.

11. The method of preparing cyclododecanone of claim 1 , wherein 0.01 to 10 parts by weight of the alkali metal halide catalyst is included, based on 100 parts by weight of the epoxidized cyclododecane.

12. The method of preparing cyclododecanone of claim 1 , wherein a conversion rate of the cyclododecene and a conversion rate of the epoxidized cyclododecane are 90% or more.

Assignees

• Hanwha Solutions Corp

Inventors

• Kim Jiyeon
• Park Jeongseok
• Park Jinho
• Song Kyuho

Classifications

• B01J31/0239

  Quaternary ammonium compounds · CPC title

• B01J23/30

  Tungsten · CPC title

• C07C45/28 Primary

  of CHx-moieties · CPC title

• B01J27/16

  containing oxygen {, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr} · CPC title

• C07D301/12 Primary

  with hydrogen peroxide or inorganic peroxides or peracids · CPC title