1,5,9-cyclododecatriene composition and continuous preparation method therefor

Patent metadata

Field	Value
Publication number	US-12286388-B2
Application number	US-202118034140-A
Country	US
Kind code	B2
Filing date	Oct 27, 2021
Priority date	Oct 27, 2020
Publication date	Apr 29, 2025
Grant date	Apr 29, 2025

Abstract

The present invention provides a continuous preparation method of cyclododecatriene including: preparing a reaction composition by mixing butadiene, a main catalyst, and a co-catalyst with a toluene solvent; and allowing the reaction composition to react at a reaction pressure higher than a vapor pressure of the butadiene, and a cyclododecatriene composition prepared by the continuous preparation method.

First claim

The invention claimed is:

1. A continuous preparation method of cyclododecatriene comprising:
preparing a reaction composition by mixing butadiene, a main catalyst, and a co-catalyst with a toluene solvent; and
reacting the reaction composition at a reaction pressure higher than a vapor pressure of the butadiene in a temperature range of 30 to 70° C.

2. The continuous preparation method of cyclododecatriene of claim 1 , wherein the butadiene and the toluene solvent are included at a weight ratio of 1:1 to 3:1.

3. The continuous preparation method of cyclododecatriene of claim 1 , wherein the main catalyst is one or more of titanium chloride and titanium alkoxide.

4. The continuous preparation method of cyclododecatriene of claim 1 , wherein a concentration of the main catalyst in the reaction composition is more than 0.5 mmol/L and less than 2.5 mmol/L.

5. The continuous preparation method of cyclododecatriene of claim 1 , wherein the main catalyst and the co-catalyst are mixed so that an aluminum/titanium (Al/Ti) mole ratio is 10 to 100.

6. The continuous preparation method of cyclododecatriene of claim 1 , wherein the butadiene is mixed in a liquid state.

7. The continuous preparation method of cyclododecatriene of claim 1 , wherein the reaction pressure is 5 to 10 bar.

8. The continuous preparation method of cyclododecatriene of claim 1 , wherein the reaction composition is reacted for 30 to 80 minutes.

9. A cyclododecatriene composition prepared by the continuous preparation method of cyclododecatriene of claim 1 , wherein a conversion of the butadiene is 85 wt % or more and a selectivity of the cyclododecatriene is 85 wt % or more.

10. The cyclododecatriene composition of claim 9 , wherein the cyclododecatriene composition has a 4-vinylcyclohexane (VCH) selectivity of less than 1 wt %.

11. The cyclododecatriene composition of claim 9 , wherein the cyclododecatriene composition has a cyclooctadiene (COD) selectivity of less than 0.2 wt %.

12. The cyclododecatriene composition of claim 9 , wherein the cyclododecatriene composition has a toluene-C 4 (Tol-C 4 ) selectivity of less than 15 wt %.

Assignees

• Hanwha Solutions Corp

Inventors

• Hyeong Seonghoon
• Park Jinho
• Jang Namjin

Classifications

• C07C13/277

  with a cyclododecatriene ring · CPC title

• B01J21/063 Primary

  Titanium; Oxides or hydroxides thereof · CPC title

• B01J21/02

  Boron or aluminium; Oxides or hydroxides thereof · CPC title

• C07C2601/20

  the ring being twelve-membered · CPC title

• C07C2527/20

  Carbon compounds · CPC title