Butadiene telomerization catalyst preparation and use thereof

Patent metadata

Field	Value
Publication number	US-11713286-B2
Application number	US-202217703458-A
Country	US
Kind code	B2
Filing date	Mar 24, 2022
Priority date	Apr 10, 2015
Publication date	Aug 1, 2023
Grant date	Aug 1, 2023

Abstract

Catalyst compositions are prepared by contacting a palladium source and 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane and a methoxyocta-diene compound, in a primary aliphatic alcohol, under suitable conditions including a ratio of equivalents of palladium to equivalents of 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane ranging from greater than 1:1 to 1:1.3. The result is a complex of palladium, a 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaada-mantane ligand, and a ligand selected from a methoxyoctadiene ligand, an octadienyl ligand, or a protonated octadienyl. Such complexes may, in solution, exhibit surprising solubility and storage stability and are useful in the telomerization of butadiene, which is a step in the production of 1-octene.

First claim

The invention claimed is:

1. A process for preparing a catalyst composition useful for catalyzing the telomerization of butadiene comprising dissolving as reagents a palladium source, 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane, as set forth in structures (I) and (II),

and a methoxyoctadiene compound in a primary aliphatic alcohol, such that the ratio of equivalents of the palladium to equivalents of the 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane ranges from greater than 1:1 to 1:1.3, to form a catalyst composition comprising a complex comprising palladium, a 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane ligand, and a ligand selected from a methoxyoctadiene ligand, an octadienyl ligand, or a protonated octadienyl ligand, in the primary aliphatic alcohol.

2. The process of claim 1 wherein:
(a) the palladium source is selected from palladium acetylacetonate, palladium formate, palladium acetate, palladium propionate, palladium octanoate, palladium carbonate, palladium hydroxide, palladium citrate, tetrakis(triphenylphosphine) palladium, bis(1,5-cyclooctadiene) palladium, bis(dibenzylideneacetone) palladium, and combinations thereof;
(b) the methoxyoctadiene compound is selected from 1-methoxy-2,7-octadiene, 3-methoxy-1,7-octadiene, and combinations thereof;
(c) the primary aliphatic alcohol is selected from methanol, ethanol, propanol, butanol, ethylene glycol, propylene glycol, glycerol, and combinations thereof; or
(d) a combination thereof.

3. The process of claim 1 , wherein the palladium source is selected from palladium acetylacetonate, palladium formate, palladium acetate, palladium propionate, palladium octanoate, palladium carbonate, palladium hydroxide, palladium citrate, tetrakis(triphenylphosphine) palladium, bis(1,5-cyclooctadiene) palladium, bis(dibenzylideneacetone) palladium, and combinations thereof.

4. The process of claim 1 , wherein the methoxyoctadiene compound is selected from 1-methoxy-2,7-octadiene, 3-methoxy-1,7-octadiene, and combinations thereof.

5. The process of claim 1 , wherein the primary aliphatic alcohol is selected from methanol, ethanol, propanol, butanol, ethylene glycol, propylene glycol, glycerol, and combinations thereof.

6. The process of claim 1 , wherein the process further comprises adding (a) a carboxylic acid; (b) a promoter selected from alkoxides, enolates, phenoxides, borohydrides, and hydrazides, all of alkali metals; alkaline earth metals and quaternary ammoniums; alkali metal salts; or a combination thereof; or (c) a combination thereof.

7. The process of claim 1 , wherein the process further comprises adding a carboxylic acid.

8. The process of claim 1 , wherein the process further comprises adding a promoter.

9. The process of claim 8 , wherein the promoter is selected from alkoxides, enolates, phenoxides, borohydrides, and hydrazides, all of alkali metals; alkaline earth metals and quaternary ammoniums; alkali metal salts; or a combination thereof.

10. The process of claim 1 , wherein the ratio of equivalents of the palladium source to the equivalents of the 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phospha-adamantane ranges from 1:1.2 to 1:1.3.

Assignees

• Dow Global Technologies Llc

Inventors

• Klinkenberg Jessica L
• Briggs John R

Classifications

• C07C2/406 Primary

  with hydrides or organic compounds · CPC title

• B01J31/2438

  and further hetero atoms as ring members, excluding the positions adjacent to P · CPC title

• C07C41/06 Primary

  by addition of organic compounds only · CPC title

• B01J2231/20

  Olefin oligomerisation or telomerisation · CPC title

• B01J2531/824

  Palladium · CPC title