Granted Patent B2

US 12,377,405 · App. 17/192,452 · Granted Aug 5, 2025

Inventor: Han Lee (Chicago, IL)

Assignee: Novomer, Inc.

B01J31/183B01J31/1815B01J31/2243C07D487/22C07F5/069B01J2231/321B01J2531/0205B01J2531/025B01J2531/0252B01J2531/31B01J2531/845

Abstract

Claims (33)

1. A method for preparing an aluminum-based carbonylation catalyst and a ketone, comprising contacting a compound of formula I with a neutral metal carbonyl compound to produce the aluminum-based carbonylation catalyst and the ketone, wherein:

the compound of formula I is

the neutral metal carbonyl compound is dicobalt octacarbonyl, tetracobalt dodecacarbonyl, or a mixture thereof,

the aluminum-based carbonylation catalyst is

[Co(CO) 4 ] − ; and

the ketone is

wherein:

Q is a nitrogen atom and the four Q groups are part of a single porphyrin ligand; and

R q is an optionally substituted C 1-12 aliphatic group.

2. The method of claim 1 , wherein the moiety

is:

wherein:

R d is independently at each occurrence hydrogen, halogen, —OR 4 , —NR y 2 , —SR, —CN, —NO 2 , —SO 2 R y , —SOR y , —SO 2 NR y 2 ; —CNO, —NRSO 2 R y , —NCO, —N 3 , —SiR 3 ; or an optionally substituted group selected from the group consisting of C 1-20 aliphatic; C 1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 6- to 10-membered aryl; 5- to 10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and 4- to 7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, where two or more R d groups may be taken together to form one or more optionally substituted rings,

each R y is independently hydrogen, or an optionally substituted group selected the group consisting of: carbamoyl, arylalkyl; 6- to 10-membered aryl; C 1-12 aliphatic; C 1-12 heteroaliphatic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 5- to 10-membered heteroaryl having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 4- to 7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; an oxygen protecting group; and a nitrogen protecting group; where two R y on the same nitrogen atom may be taken with the nitrogen atom to form an optionally substituted 4- to 7-membered heterocyclic ring having 0-2 additional heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur,

R 4 is a hydroxyl protecting group or R y , and

R is independently at each occurrence optionally substituted C 1-12 aliphatic or optionally substituted aryl.

3. The method of claim 1 , wherein the moiety

is:

4. The method of claim 1 , wherein the moiety

is:

wherein:

R d is independently at each occurrence hydrogen, halogen, —OR 4 , —NR y 2 , —SR, —CN, —NO 2 , —SO 2 R y , —SOR y , —SO 2 NR y 2 ; —CNO, —NRSO 2 R y , —NCO, —N 3 , —SiR 3 ; or an optionally substituted group selected from the group consisting of C 1-20 aliphatic; C 1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 6- to 10-membered aryl; 5- to 10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and 4- to 7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, where two or more R d groups may be taken together to form one or more optionally substituted rings,

each R y is independently hydrogen, or an optionally substituted group selected the group consisting of: carbamoyl, arylalkyl; 6- to 10-membered aryl; C 1-12 aliphatic; C 1-12 heteroaliphatic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 5- to 10-membered heteroaryl having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 4- to 7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; an oxygen protecting group; and a nitrogen protecting group; where two R y on the same nitrogen atom may be taken with the nitrogen atom to form an optionally substituted 4- to 7-membered heterocyclic ring having 0-2 additional heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur,

R 4 is a hydroxyl protecting group or R y , and

R is independently at each occurrence optionally substituted C 1-12 aliphatic or optionally substituted aryl.

5. The method of claim 1 , wherein the moiety

is

6. The method of claim 1 , wherein the moiety

is:

7. The method of claim 1 , wherein the carbonylation catalyst is produced in a composition having a halide or alkali metal salt content in an amount less than about 200 ppm.

8. The method of claim 1 , wherein R q is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and octyl.

9. The method of claim 1 , wherein R q is ethyl.

10. The method of claim 1 , wherein the compound of formula I is:

Assignments (4)

Continuity (4)

References Cited (226)