IP Library Granted Patent US 11,629,115
Granted Patent B2
US 11,629,115 · App. 17/122,187 · Granted Apr 18, 2023

Alkoxycarbonylation of trivinylcyclohexane

Inventors: Kaiwu Dong (BoZhou, CN); Robert Franke (Marl, DE); Ralf Jackstell (Rostock, DE); Matthias Beller (Ostseebad Nienhagen, DE)
Assignee: EVONIK OPERATIONS GMBH
C07C67/40B01J31/2295C07C67/38B01J2531/824C07C69/003
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Quick Facts
Patent No.
US 11,629,115
App. No.
17/122,187
Granted
Apr 18, 2023
Kind
B2
Abstract

Process for the alkoxycarbonylation of trivinylcyclohexane.

Claims (40)

1. A process for preparing trivinylcyclohexane triesters comprising the process steps of:

a) initially charging one of the compounds (i), (ii), (iii) or a mixture of at least two of these compounds:

b) adding the ligand (L) and a compound comprising Pd,

or adding a complex comprising Pd and the ligand (L):

c) adding an alcohol having 1 to 12 carbon atoms;

d) feeding in CO;

e) heating the reaction mixture of a) to d), wherein the compound/the mixture of a) is converted to a trivinylcyclohexane triester.

2. The process according to claim 1 ,

wherein the compound (i) is initially charged in process step a).

3. The process according to claim 1 ,

wherein the compound (ii) is initially charged in process step a).

4. The process according to claim 1 ,

wherein the alcohol in process step c), besides the oxygen, does not comprise any further heteroatoms and contains no multiple bonds.

5. The process according to claim 1 ,

wherein the alcohol in process step c) is selected from:

methanol, ethanol, n butanol, methylpropanol, n pentanol, iso pentanol, 2-methylbutanol, 3-methylbutanol, n hexanol, iso hexanol, n heptanol, iso heptanol, n octanol, iso octanol, 2-ethylhexanol, n nonanol, iso nonanol, n decanol, iso decanol, or 2-propylheptanol.

6. The process according to claim 1 ,

wherein the alcohol in process step c) is methanol.

7. The process according to claim 1 ,

wherein CO is fed in in process step d) up to a pressure in the range from 20 bar to 60 bar.

8. The process according to claim 1 ,

wherein the heating in process step e) is carried out at a temperature in the range from 90° C. to 130° C.

9. The process according to claim 1 ,

comprising the additional process step f):

f) purifying the trivinylcyclohexane triester.

10. A process comprising the process steps of:

a) initially charging one of the compounds (i), (ii), (iii) or a mixture of at least two of these compounds:

b) adding the ligand (L) and a compound comprising Pd,

or adding a complex comprising Pd and the ligand (L):

c) adding an alcohol having 1 to 12 carbon atoms;

d) feeding in CO;

e) heating the reaction mixture of a) to d), wherein the compound/the mixture of a) is converted to a triester;

f) purifying the triester; and

g) reacting the purified triester with NaOMe and H 2 to give the triol.

11. The process according to claim 10 ,

wherein the reaction in process step g) is catalyzed with Ru-MACHO-BH.

12. The process according to claim 10 ,

wherein the reaction in process step g) is carried out at a H 2 pressure in the range of 30 bar to 70 bar.

13. The process according to claim 10 ,

wherein the re Currently Amended action in process step g) is carried out at a temperature in the range from 80° C. to 120° C.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2024
From: EVONIK OPERATIONS GMBH
To: EVONIK OXENO GMBH & CO. KG
Reel/Frame 066242/0585 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2021
From: DONG, KAIWU; FRANKE, ROBERT; JACKSTELL, RALF; BELLER, MATTHIAS
To: EVONIK OPERATIONS GMBH
Reel/Frame 056472/0831 →
Priority Claims (1)
EP 19216884 · Dec 17, 2019 · regional
Continuity (1)
Related Publication 20210179532A1 · Jun 17, 2021