LIGAND COMPOUND, CATALYST SYSTEM FOR OLEFIN OLIGOMERIZATION, AND METHOD FOR OLEFIN OLIGOMERIZATION USING THE SAME (As Amended)

Patent metadata

Field	Value
Publication number	US-2016304543-A1
Application number	US-201414892679-A
Country	US
Kind code	A1
Filing date	Nov 18, 2014
Priority date	Nov 18, 2013
Publication date	Oct 20, 2016
Grant date	—

Abstract

This disclosure relates to a ligand compound, a catalyst system for olefin oligomerization, and a method for olefin oligomerization using the same. The catalyst system for olefin oligomerization according to the present invention has excellent catalytic activity, and yet, exhibits high selectivity to 1-hexene and 1-octene, thus enabling efficient preparation of alpha-olefin.

First claim

1 . A ligand compound represented by the following Chemical Formula 1:

in the Chemical Formula 1,
at least one of R 1 to R 6 is a substituent represented by the following Chemical Formula 2,
the other R 1 to R 6 , which are not represented by the following Chemical Formula 2, are independently hydrogen, a C1-20 alkyl group which may or may not contain at least one heteroatom, a C3-20 cycloalkyl group, a C6-20 aryl group, a C7-20 arylalkyl group, a C7-20 alkylaryl group, or a C3-30 heteroaryl group, provided that all the other R 1 to R 6 which are not represented by the following Chemical Formula 2 cannot be hydrogen,
R 7 to R 10 are independently hydrogen, a C1-20 alkyl group which may or may not contain at least one heteroatom, a C3-20 cycloalkyl group, a C6-20 aryl group, a C7-20 arylalkyl group, a C7-20 alkylaryl group, or a C3-30 heteroaryl group, and two different neighboring groups of the R 7 to R 10 may be connected to each other to form a C6-20 aromatic ring,

in the Chemical Formula 2,
R 11 to R 14 are independently a C1-20 alkyl group, a C2-20 alkenyl group, a C6-20 aryl group, a C7-20 arylalkyl group, a C7-20 alkylaryl group, or a C7-20 alkoxyaryl group.

2 . The ligand compound according to claim 1 , wherein in the Chemical Formula 1, at least one of R 1 to R 6 that are not represented by the Chemical Formula 2 is a C1-4 alkyl group, a C3-10 cycloalkyl group, a C6-10 aryl group, or a C7-15 arylalkyl group.

3 . The ligand compound according to claim 1 , wherein R 7 to R 10 in the Chemical Formula 1 are independently hydrogen or a C1-20 alkyl group which may or may not contain at least one heteroatom, and two different neighboring groups of the R 7 to R 10 may be connected to each other to form a C6-20 aromatic ring.

4 . The ligand compound according to claim 1 , wherein R 11 to R 14 in the Chemical Formula 2 are identical to each other.

5 . The ligand compound according to claim 1 , wherein R 11 to R 14 in the Chemical Formula 2 are phenyl.

6 . The ligand compound according to claim 1 , wherein the compound represented by the Chemical Formula 1 is selected from the group consisting of

7 . A catalyst system for olefin oligomerization comprising the ligand compound according to claim 1 , a source of transition metal and a cocatalyst.

8 . The catalyst system according to claim 7 , wherein the source of transition metal is at least one selected from the group consisting of chromium(III)acetylacetonate, tris(tetrahydrofuran)chromium trichloride, chromium(III)-2-ethylhexanoate, chromium(III)tris(2,2,6,6-tetramethyl-3,5-heptanedionate), chromium(III)benzoylacetonate, chromium(III)hexafluoro-2,4-pentanedionate, and chromium(III)acetate hydroxide.

9 . The catalyst system according to claim 7 , wherein the cocatalyst is at least one selected from the group consisting of the compounds represented by the following Chemical Formulae 3 to 5:
−[Al(R 15 )−O] c -  [Chemical Formula 3]
in the Chemical Formula 3, R 15 's are identical or different, and are independently a halogen radical, a C1-20 hydrocarbyl radical, or a C1-20 hydrocarbyl radical substituted with halogen, and c is an integer of 2 or more,
D(R 16 ) 3   [Chemical Formula 4]

in the Chemical Formula 4, D is aluminum or boron, R 16 's are identical or different, and are independently hydrogen, halogen, a C1-20 hydrocarbyl or a C1-20 hydrocaryl substituted with halogen,
[L-H] + [Q(E) 4 ] −   [Chemical Formula 5]

in the Chemical Formula 5, L is neutral Lewis base, [L-H] + is Bronsted acid, Q is Br 3+ or Al 3+ , and E's are independently a C 6-20 aryl group or a C 1-20 alkyl group, unsubstituted or substituted with at least one selected from the group consisting of halogen, a C 1-20 hydrocarbyl, an alkoxy and a phenoxy group.

10 . A method for olefin oligomerization, comprising the step of multimerizing olefins in the presence of the catalyst system for olefin oligomerization of claim 7 .

11 . The method for olefin oligomerization according to claim 10 , wherein the olefin is ethylene.

12 . The method for olefin oligomerization according to claim 10 , wherein the multimerization temperature is 5 to 200° C.

13 . The method for olefin oligomerization according to claim 10 , wherein the multimerization pressure is 1 to 300 bar.

Assignees

• Lg Chemical Ltd

Inventors

• Lee Yong Ho
• Shin Eun Ji
• Sa Seok Pil
• Lee Ki Soo

Classifications

• C07F9/46 Primary

  Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids {including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof} · CPC title

• C07C2531/22

  Organic complexes · CPC title

• B01J2531/62

  Chromium · CPC title

• C08F110/02

  Ethene · CPC title

• B01J31/188

  Amide derivatives thereof · CPC title