Process to prepare aluminoxanes

Patent metadata

Field	Value
Publication number	US-10822356-B2
Application number	US-201716092037-A
Country	US
Kind code	B2
Filing date	May 19, 2017
Priority date	May 24, 2016
Publication date	Nov 3, 2020
Grant date	Nov 3, 2020

Abstract

Process to prepare alkylaminoxane by reacting, in the absence of solvent, 1 molar equivalent of alkylaluminium with 0.1 to 0.8 molar equivalent of a substituted allylic alcohol of the formula (I) wherein R1 and R2 are independently selected from aliphatic and aromatic hydrocarbon groups, and each R3, R4, and R5 is independently selected from aliphatic and aromatic hydrocarbon groups and a hydrogen atom.

First claim

The invention claimed is:

1. Process for preparing alkylaluminoxane by reacting, in the absence of solvent, 1 molar equivalent of alkylaluminium with 0.1 to 0.8 molar equivalent of a substituted allylic alcohol of the formula

wherein R1 and R2 are independently selected from aliphatic and aromatic hydrocarbon groups, and R3, R4, and R5 are independently selected from aliphatic and aromatic hydrocarbon groups and a hydrogen atom.

2. Process according to claim 1 wherein between 0.5 and 0.8 molar equivalent of substituted allylic alcohol is used per molar equivalent of alkylaluminium.

3. Process according to claim 2 wherein R1 and R2 are independently selected from branched and linear alkyl or alkylene groups of up to 20 carbon atoms, and wherein R3, R4, and R5 are independently selected from branched and linear alkyl and alkylene groups of up to 20 carbon atoms and a hydrogen atom.

4. Process according to claim 3 wherein the substituted allylic alcohol is selected from the group consisting of 4-methyl-3-pentene-2-ol, 3-methyl-2-pentene-1-ol, 3-methyl-2-hexene-1-ol, 3-ethyl-2-pentene-1-ol, (trans)-3,7-dimethyl-2,6-octadien-1-ol, and 3-methyl-2-butene-1-ol.

5. Process according to claim 1 wherein R1 and R2 are independently selected from branched and linear alkyl or alkylene groups of up to 20 carbon atoms, and wherein R3, R4, and R5 are independently selected from branched and linear alkyl and alkylene groups of up to 20 carbon atoms and a hydrogen atom.

6. Process according to claim 5 wherein the substituted allylic alcohol is selected from the group consisting of 4-methyl-3-pentene-2-ol, 3-methyl-2-pentene-1-ol, 3-methyl-2-hexene-1-ol, 3-ethyl-2-pentene-1-ol, (trans)-3,7-dimethyl-2,6-octadien-1-ol, and 3-methyl-2-butene-1-ol.

7. Process according to claim 1 wherein between 0.6 and 0.75 molar equivalent of substituted allylic alcohol is used per molar equivalent of alkylaluminium.

8. Process according to claim 1 wherein between 0.6 and 0.75 molar equivalent of substituted allylic alcohol is used per molar equivalent of alkylaluminium and wherein R1 and R2 are independently selected from branched and linear alkyl or alkylene groups of up to 20 carbon atoms, and wherein R3, R4, and R5 are independently selected from branched and linear alkyl and alkylene groups of up to 20 carbon atoms and a hydrogen atom.

9. Process according to claim 8 wherein the substituted allylic alcohol is selected from the group consisting of 4-methyl-3-pentene-2-ol, 3-methyl-2-pentene-1-ol, 3-methyl-2-hexene-1-ol, 3-ethyl-2-pentene-1-ol, (trans)-3,7-dimethyl-2,6-octadien-1-ol, and 3-methyl-2-butene-1-ol.

10. Process for preparing alkylaluminoxane by reacting, in the absence of solvent, 1 molar equivalent of alkylaluminium with 0.6 to 0.75 molar equivalent of a substituted allylic alcohol selected from the group consisting of 4-methyl-3-pentene-2-ol, 3-methyl-2-pentene-1-ol, 3-methyl-2-hexene-1-ol, 3-ethyl-2-pentene-1-ol, (trans)-3,7-dimethyl-2,6-octadien-1-ol, and 3-methyl-2-butene-1-ol.

11. Process for preparing alkylaluminoxane by reacting, in the absence of solvent, alkyl aluminium with methacrylic acid or a conjugated unsaturated carbonyl-functional compound of the formula

wherein R1 and R2 are independently selected from aliphatic hydrocarbon groups, R3 is an aliphatic hydrocarbon group or a hydrogen atom, and R4 is an aliphatic hydrocarbon group, a hydrogen atom, or a hydroxyl group in a ratio of 0.1 to 0.8 molar equivalent oxygen atoms in the part —C═O(R4) of the methacrylic acid or conjugated unsaturated carbonyl-functional compound per molar equivalent of aluminium atoms in the alkylaluminium.

12. Process according to claim 11 wherein R1 and R2 are independently selected from branched and linear aliphatic alkyl and alkylene groups of up to 20 carbon atoms, R3 is a branched or linear aliphatic alkyl or alkylene group of up to 20 carbon atoms or a hydrogen atom, and R4 is a branched or linear aliphatic alkyl or alkylene group of up to 20 carbon atoms, a hydrogen atom, or a hydroxyl group.

13. Process according to claim 12 wherein methacrylic acid or one of the conjugated unsaturated carbonyl-functional compounds is selected from the group consisting of 3-methyl-2-butenoic acid, 2-methyl-2-propenoic acid, 4-methyl-3-pentene-2-one, 3-methyl-2-butenal.

14. Process according to claim 11 wherein methacrylic acid or one of the conjugated unsaturated carbonyl-functional compounds is selected from the group consisting of 3-methyl-2-butenoic acid, 2-methyl-2-propenoic acid, 4-methyl-3-pentene-2-one, 3-methyl-2-butenal.

15. Process according to claim 11 wherein the alkylaluminium is a trialkylaluminium wherein the alkyl groups are alkyl groups of up to 8 carbon atoms.

16. Process of claim 15 wherein one or more of the alkyl groups on the alkylaluminium are isobutyl, ethyl or methyl.

17. Process according to claim 15 wherein the alkylaluminium is a compound wherein at least 50% of the alkyl groups are methyl.

18. Process according to claim 17 wherein the alkylaluminium contains trimethylaluminium.

19. Process according to claim 18 , wherein the obtained aluminoxane is subsequently dissolved in an aliphatic solvent.

20. Process according to claim 19 wherein the aliphatic solvent is hexane or heptane.

Assignees

• Nouryon Chemicals Int Bv

Inventors

• Van Der Kruijs Peter

Classifications

• C07F5/066

  compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage) · CPC title

• C07F5/068 Primary

  preparation of alum(in)oxanes · CPC title

• B01J31/143

  of aluminium · CPC title

• C08F4/52

  selected from boron, aluminium, gallium, indium, thallium or rare earths (C08F4/14 takes precedence) · CPC title

• B01J2231/20

  Olefin oligomerisation or telomerisation · CPC title