Process for preparing cyclododecanone

Patent metadata

Field	Value
Publication number	US-9533933-B2
Application number	US-201514815014-A
Country	US
Kind code	B2
Filing date	Jul 31, 2015
Priority date	Aug 1, 2014
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

Cyclododecanone (CDON) is prepared by epoxidizing cyclododecene (CDEN) to epoxycyclododecane (CDAN epoxide), and rearranging the CDAN epoxide to CDON to obtain a mixture comprising said CDON and CDEN, wherein CDEN is separated from the CDON-containing mixture and sent to the epoxidation to CDAN epoxide in step a.

First claim

The invention claimed is:

1. A process for preparing cyclododecanone (CDON) by a reaction route I, comprising
a. epoxidizing cyclododecene (CDEN) to epoxycyclododecane (CDAN epoxide), and
b. rearranging the CDAN epoxide to CDON to obtain a mixture comprising said CDON and CDEN,
wherein:
CDEN is separated from the CDON-containing mixture and sent to the epoxidation to CDAN epoxide in step a;
the CDAN epoxide from step a comprises cyclododecane (CDAN) which is at least partly removed prior to the rearrangement in step b; and
the CDAN removed prior to the rearrangement in step b is sent to a reaction route II for preparation of CDON, comprising:
c. hydrogenation of cyclododecatriene (CDT) to CDAN,
d. oxidation of CDAN to give a mixture comprising cyclododecanol (CDOL) and CDON and
e. dehydrogenation of CDOL to CDON.

2. The process according to claim 1 , wherein CDEN for the epoxidation in step a is obtained from cyclododecatriene (CDT).

3. The process according to claim 1 , wherein the rearrangement in step b is effected in the presence of a noble metal catalyst.

4. The process according to claim 3 , wherein the catalyst for the rearrangement (step b) comprises titanium dioxide, zirconium dioxide or both.

5. The process according to claim 1 , wherein the CDAN epoxide from step a comprises CDEN which is at least partly removed prior to the rearrangement in step b.

6. The process according to claim 1 , wherein the CDON-containing mixture comprises cyclododecanol (CDOL) which is dehydrogenated to CDON.

7. The process according to claim 6 , wherein the CDOL is separated from the CDON-containing mixture prior to the dehydrogenation and is sent to the reaction route II for preparation of CDON.

8. The process according to claim 1 , wherein at least one removal of any compound is conducted by distillation.

9. The process according to claim 1 , wherein all removals of any compound are conducted by distillation.

10. The process according to claim 1 , wherein CDT is obtained from 1,3-butadiene.

11. A process for synthesizing laurolactam from CDON, wherein the CDON is prepared according to claim 1 .

12. The process according to claim 11 , wherein the CDON is converted to cyclododecanone oxime (CDON oxime).

13. A process for preparing nylon-12 from CDON, wherein the CDON is prepared according to claim 1 .

Assignees

• Micoine Kevin
• Meier Ralf
• Herwig Juergen
• Roos Martin
• Haeger Harald
• Cameretti Luca
• Doering Jens
• Evonik Degussa Gmbh

Inventors

• Micoine Kevin
• Meier Ralf
• Herwig Juergen
• Roos Martin
• Haeger Harald
• Cameretti Luca
• Doering Jens

Classifications

• C07D225/02

  not condensed with other rings · CPC title

• C07C45/28

  of CHx-moieties · CPC title

• B01J23/44

  Palladium · CPC title

• C07C45/512 Primary

  the singly bound functional group being a free hydroxyl group · CPC title

• C07C29/52

  in the presence of mineral boron compounds with, when necessary, hydrolysis of the intermediate formed · CPC title