Process for deactivation of an olefin oligomerization catalyst

Patent metadata

Field	Value
Publication number	US-10407359-B2
Application number	US-201615760383-A
Country	US
Kind code	B2
Filing date	Sep 13, 2016
Priority date	Sep 16, 2015
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

A process for deactivation of an olefin oligomerization catalyst is described, including contacting a catalyst composition with a catalyst quenching medium to form a deactivated catalyst composition, and recovering excess catalyst quenching medium. The catalyst quenching medium includes an alcohol having at least 6 carbon atoms, an organic amine, an amino alcohol, or a combination comprising at least one of the foregoing. The catalyst quenching medium is present in a molar ratio of catalyst quenching medium to catalyst of at least 3:1. A process for the oligomerization of an olefin is also described, including feeding the olefin, a solvent, and a catalyst composition into a reactor, oligomerizing the olefin in the reactor to form a reaction product stream including linear alpha olefins, solvent, and the catalyst composition, and contacting the reaction product stream with a catalyst quenching medium.

First claim

The invention claimed is:

1. A process for deactivation of an olefin oligomerization catalyst, the process comprising:
contacting the olefin oligomerization catalyst with a catalyst quenching medium comprising an alcohol having at least 6 carbon atoms, an organic amine, an amino alcohol, or a combination comprising at least one of the foregoing, to form a deactivated catalyst composition, wherein the catalyst quenching medium is present in a molar ratio of catalyst quenching medium to the olefin oligomerization catalyst of at least 100:1; and
recovering excess catalyst quenching medium.

2. The process of claim 1 , further comprising recycling the recovered catalyst quenching medium.

3. The process of claim 1 , wherein the catalyst composition comprises a chromium source, a heteroatomic multidentate ligand, an activator, and optionally, a modifier.

4. The process of claim 1 , wherein the catalyst composition is halogen-free.

5. The process of claim 1 , wherein the catalyst quenching medium comprises a C 6-20 alkyl alcohol.

6. The process of claim 1 , wherein the catalyst quenching medium comprises at least one of 1-hexanol, 3-hexanol, 2-ethyl-1-hexanol, 3-octanol, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 2-methyl-3-heptanol, 1-octanol, 2-octanol, 4-octanol, 7-methyl-2-decanol, 1-decanol, 2-decanol, 3-decanol, 4-decanol, 5-decanol, or 2-ethyl-1-decanol.

7. The process of claim 1 , wherein at least 60% of the catalyst quenching medium is recovered.

8. A process for the oligomerization of an olefin, the process comprising:
feeding the olefin, a solvent, and a catalyst composition comprising a chromium source, a heteroatomic multidentate ligand, and an activator into a reactor;
oligomerizing the olefin in the reactor to form a reaction product stream comprising linear alpha olefins, the solvent, and the catalyst composition;
contacting the reaction product stream with a catalyst quenching medium comprising an alcohol having at least 6 carbon atoms, an organic amine, an amino alcohol, or a combination comprising at least one of the foregoing, to form a first intermediate stream comprising a deactivated catalyst composition, linear alpha olefins, the solvent, and excess catalyst quenching medium;
separating the linear alpha olefins from the first intermediate stream to provide a second intermediate stream comprising the deactivated catalyst composition and excess catalyst quenching medium; and
recovering the catalyst quenching medium from the second intermediate stream;
wherein the catalyst quenching medium is contacted with the reaction product stream in a molar ratio of catalyst quenching medium to the catalyst composition of at least 100:1.

9. The process of claim 8 , wherein the olefin is ethylene.

10. The process of claim 8 , wherein the solvent comprises at least one of toluene, xylene, mesitylene, ethyl benzene, n-pentane, n-hexane, and cyclohexane.

11. The process of claim 3 , wherein the chromium source is at least one of CrCl 3 (tetrahydrofuran) 3 , Cr(III)acetylacetonate, Cr(III)octanoate, chromium hexacarbonyl, Cr(III)-2-ethylhexanoate, benzene(tricarbonyl)-chromium, or Cr(III)chloride.

12. The process of claim 3 , wherein the heteroatomic multidentate ligand is (phenyl) 2 PN(iso-propyl)P(phenyl)N(iso-propyl)H.

13. The process of claim 3 , wherein the activator is a tri(C 1-6 alkyl) aluminum.

14. The process of claim 3 , wherein the modifier comprises tetraphenylphosphonium chloride, tetraethylammonium chloride-monohydrate, tetraethylammonium chloride, isopropylamine hydrochloride, triethylamine hydrochloride, tetrapropylammonium chloride, trimethyldodecylammonium chloride, tetra-n-butylammonium chloride, tetraethylammonium bromide, p-toluidine hydrochloride, dimethyldistearylammonium chloride and (tri-n-butyl)-n-tetradecylphosphonium chloride.

15. The process of claim 8 , wherein the linear alpha olefins comprise C 4-12 linear alpha olefins.

16. The process of claim 8 , wherein the linear alpha olefins comprise at least one of 1-butene, 1-hexene, or 1-octene.

17. The process of claim 8 , wherein the catalyst quenching medium is miscible with the reaction product stream.

18. The process of claim 8 , wherein the process further comprises recycling recovered catalyst quenching medium.

19. The process of claim 8 , wherein distillation is used for separating the linear alpha olefins and recovering the catalyst quenching medium.

20. The process of claim 8 , wherein separating the linear alpha olefins and recovering the catalyst quenching medium occur in different rectification columns.

Assignees

• Sabic Global Technologies Bv

Inventors

• Alqahtani Abdullah
• Wöhl Anina
• Müller Wolfgang
• Harff Marco
• Bölt Heinz
• Metzner Andreas
• Noack Ralf
• Gärtner Lars-Erik
• Meiswinkel Andreas

Classifications

• C07C2527/132

  Compounds comprising a halogen and chromium, molybdenum, tungsten or polonium · CPC title

• C07C2/26

  with hydrides or organic compounds (C07C2/20 takes precedence) · CPC title

• C07C2/22

  Metal halides; Complexes thereof with organic compounds · CPC title

• B01J31/34 Primary

  of chromium, molybdenum or tungsten · CPC title

• B01J2231/20

  Olefin oligomerisation or telomerisation · CPC title