IP Library Granted Patent US 9,533,932
Granted Patent B2
US 9,533,932 · App. 14/814,984 · Granted Jan 3, 2017

Process for preparing cyclododecanone

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Quick Facts
Patent No.
US 9,533,932
App. No.
14/814,984
Granted
Jan 3, 2017
Kind
B2
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 cyclododecane (CDAN), wherein CDAN is separated from the CDON-containing mixture and oxidized to CDON.

Claims (25)

1. A process for preparing cyclododecanone (CDON) by a reaction route I, said 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 cyclododecane (CDAN),

wherein CDAN is separated from the CDON-containing mixture and oxidized to CDON.

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

3. The process according to claim 2 , wherein the catalyst for the rearrangement comprises titanium dioxide, zirconium dioxide or both.

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

5. The process according to claim 4 , wherein the CDAN removed prior to the rearrangement is oxidized to CDON.

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 a reaction route II for preparation of CDON, said reaction route II comprising

a. hydrogenation of cyclododecatriene (CDT) to CDAN,

b. oxidation of CDAN to give a mixture comprising CDOL and CDON and

c. dehydrogenation of CDOL to CDON.

8. The process according to claim 1 , wherein the CDAN removed prior to performance of the oxidation, is sent to a reaction route II for preparation of CDON, comprising

a. hydrogenation of CDT to CDAN,

b. oxidation of CDAN to give a mixture comprising CDOL and CDON, and

c. dehydrogenation of CDOL to CDON.

9. The process according to claim 8 , wherein the CDAN removed is sent to the oxidation of CDAN as per step b of reaction route II.

10. The process according to claim 9 , wherein the CDAN contains up to 0.5% by weight of cyclododecene (CDEN), based on the total weight of CDAN and CDEN.

11. The process according to claim 8 , wherein the CDAN removed is sent to the hydrogenation of CDT as per step a of reaction route II, the CDAN containing 0.1% to 99% by weight of CDEN, based on the total weight of CDAN and CDEN.

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

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

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

15. The process according to claim 14 , wherein the CDON is converted to cyclododecanone oxime (CDON oxime).

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

Assignments (2)
CHANGE OF NAME Recorded Jan 31, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051765/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 8, 2015
From: MICOINE, KEVIN; MEIER, RALF; HERWIG, JUERGEN; ROOS, MARTIN; HAEGER, HARALD; CAMERETTI, LUCA; DOERING, JENS
To: EVONIK DEGUSSA GMBH
Reel/Frame 036757/0326 →