IP Library Granted Patent US 8,722,933
Granted Patent B2
US 8,722,933 · App. 12/702,655 · Granted May 13, 2014

Method for preparing metal complexes of polydentate beta-ketoiminates

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Quick Facts
Patent No.
US 8,722,933
App. No.
12/702,655
Granted
May 13, 2014
Kind
B2
Abstract

A method for making a group 2 metal-containing polydentate β-ketoiminate represented by the following structure A: wherein M is a metal selected from the group consisting of Mg, Ca, Sr, and Ba; R 1 , R 3 , R 5 , and R 6 are independently selected from an alkyl group, a fluoroalkyl group, a cycloaliphatic group, and an aryl group; R 2 is selected from a hydrogen atom, an alkyl group, an alkoxy group, a cycloaliphatic group, and an aryl group; and R 4 is an alkyenyl bridge, comprising: reacting M in a reaction mixture comprising a tridentate ketoimine ligand and an alcohol comprising at least one selected from the group consisting of R 7 OH and (OH) n R 8 wherein R 7 and R 8 are independently selected from an alkyl group and an aryl group. In certain embodiments, the reaction mixture further comprises an organic solvent.

Claims (20)

1. A method for preparing a group 2 metal-containing polydentate β-ketoiminate represented by the following structure A:

wherein M is a metal selected from the group consisting of Mg, Ca, Sr, and Ba; R 1 , R 3 , R 5 , and R 6 are independently selected from an alkyl group, a fluoroalkyl group, a cycloaliphatic group, and an aryl group; R 2 is selected from a hydrogen atom, an alkyl group, an alkoxy group, a cycloaliphatic group, and an aryl group; and R 4 is an alkyenyl bridge, wherein the method comprises:

reacting M in a reaction mixture comprising a tridentate ketoimine ligand and an alcohol selected from the group consisting of methanol, ethanol, n-propanol, iso-propanol, n-butanol, sec-butanol, iso-butanol, n-pentanol, neo-pentanol, and combinations thereof, for a reaction time of from about 4 to about 48 hours to obtain the group 2 metal-containing polydentate β-ketoiminate at a yield greater than 80%, wherein the tridentate ketoimine ligand comprises a compound represented by the following structure B:

wherein R 1 , R 3 , R 5 , and R 6 are independently selected from an alkyl group, a fluoroalkyl group, a cycloaliphatic group, and an aryl group; R 2 is selected from a hydrogen atom, an alkyl group, an alkoxy group, a cycloaliphatic group, and an aryl group; and R 4 is an alkyenyl bridge.

2. The method of claim 1 wherein M comprises strontium.

3. The method of claim 1 wherein the molar ratio of M to the alcohol in the reaction mixture ranges from about 0.1 to 5.

4. The method of claim 1 wherein the reaction mixture further comprises an organic solvent.

5. The method of claim 4 wherein the organic solvent comprises toluene and hexane.

6. The method of claim 4 wherein the organic solvent comprises tetrahydrofuran.

7. The method of claim 4 wherein the reacting step is carried out in the presence of the organic solvent wherein at least one of the tridentate ketoimine ligand and the alcohol is at least partially soluble therein.

8. The method of claim 4 wherein the metal and the tridentate ketoimine ligand are added in the organic solvent and then the alcohol is added.

9. The method of claim 8 wherein the alcohol is added to the reaction mixture portion wise to avoid sudden exothermal reaction.

10. The method of claim 4 wherein the reaction mixture is refluxed at the boiling point of the organic solvent.

11. The method of claim 1 wherein the metal-containing polydentate β-ketoiminate comprises bis(2,2-dimethyl-5-(dimethylaminoethyl-imino)-3-hexanonato-N,O,N′)strontium.

12. The method of claim 1 wherein the metal-containing polydentate β-ketoiminate comprises bis(2,2-dimethyl-5-(1-dimethylamino-2-propylimino)-3-hexanonato-N,O,N′)strontium.

13. The method of claim 1 wherein the metal-containing polydentate β-ketoiminate comprises bis(2,2-dimethyl-5-(1-ethylmethylaminoethyl-imino)-3-hexanonato-N,O,N′)strontium.

14. The method of claim 1 wherein the metal-containing polydentate β-ketoiminate comprises bis(2,2-dimethyl-5-(1-methyethylamino-2-propylimino)-3-hexanonato-N,O,N′)strontium.

15. The method of claim 1 wherein the metal-containing polydentate β-ketoiminate comprises bis(2,2-dimethyl-5-(1-diethylaminoethyl-imino)-3-hexanonato-N,O,N′)strontium.

16. The method of claim 1 wherein the metal-containing polydentate β-ketoiminate comprises bis(2,2-dimethyl-5-(1-diethylamino-2-propylimino)-3-hexanonato-N,O,N′)strontium.

17. The method of claim 1 wherein the alcohol is iso-propanol.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Oct 7, 2019
From: CITIBANK, N.A., AS AGENT
To: VERSUM MATERIALS US, LLC
Reel/Frame 050647/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 20, 2017
From: AIR PRODUCTS AND CHEMICALS, INC.
To: VERSUM MATERIALS US, LLC
Reel/Frame 041772/0733 →
PATENT SECURITY AGREEMENT Recorded Oct 27, 2016
From: VERSUM MATERIALS US, LLC
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 040503/0442 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2010
From: LEI, XINJIAN; SPENCE, DANIEL P.
To: AIR PRODUCTS AND CHEMICALS, INC.
Reel/Frame 024087/0323 →