Method for manufacturing cyclododecanone

Patent metadata

Field	Value
Publication number	US-2022064094-A1
Application number	US-201917298921-A
Country	US
Kind code	A1
Filing date	Sep 16, 2019
Priority date	Dec 19, 2018
Publication date	Mar 3, 2022
Grant date	—

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

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.

2 . The method of preparing cyclododecanone of claim 1 , wherein the hydrogen peroxide additionally 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, and In m is a mole ratio (B/A) between cyclododecene (A) and hydrogen peroxide additionally injected (B).

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

4 . 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.

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

6 . 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.

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

8 . 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.

9 . The method of preparing cyclododecanone of claim 8 , 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.

10 . 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.

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

12 . 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.

13 . 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

• C07D301/12 Primary

  with hydrogen peroxide or inorganic peroxides or peracids · 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

• C07C45/28 Primary

  of CHx-moieties · CPC title

• C07C2601/20

  the ring being twelve-membered · CPC title

• B01J23/30

  Tungsten · CPC title