Catalyst systems and processes for cyclic poly alpha-olefins

Patent metadata

Field	Value
Publication number	US-2026055215-A1
Application number	US-202319112165-A
Country	US
Kind code	A1
Filing date	Sep 14, 2023
Priority date	Sep 16, 2022
Publication date	Feb 26, 2026
Grant date	—

Abstract

The present disclosure relates to cyclic poly alpha-olefin (PAO) materials prepared from alpha-olefins, and processes for making them.

First claim

1 . A process for producing a poly alpha-olefin (PAO) from two or more different alpha-olefins, the process comprising:
contacting a feed comprising one or more C 6 -C 32 cyclic alpha-olefins and one or more C 4 -C 32 linear and/or branched alpha-olefins with a catalyst system comprising a metallocene compound in a polymerization reactor under polymerization conditions to effect a polymerization reaction to obtain a polymerization reaction mixture, the polymerization reaction mixture comprising a mixture of PAOs (e.g., PAO molecules) having vinylidenes, tri-substituted vinylenes, di-substituted vinylenes and optionally vinyl unsaturation, and obtaining an unsaturated PAO product from the polymerization reaction mixture.

2 . The process of claim 1 , wherein the unsaturated PAO product comprises a mixture of PAO molecules having vinylidenes, tri-substituted vinylenes, di-substituted vinylenes, and optionally vinyl unsaturation, and, optionally, is substantially free of the alpha-olefin feed.

3 . The process of claim 1 , wherein one of the one or more C 6 -C 32 cyclic alpha-olefins comprises a ring unsaturation, and the unsaturated PAO product further comprises cyclic di-substituted vinylenes.

4 . The process of claim 1 , wherein the unsaturated PAO product comprises dimer and/or trimer molecules having vinylidenes, tri-substituted vinylenes, di-substituted vinylenes and optionally vinyl unsaturation.

5 - 14 . (canceled)

15 . The process of claim 1 , wherein the one or more cyclic C 6 -C 32 alpha-olefins are selected from vinylcyclobutane, vinylcyclopentane, vinylcyclohexane, 4-vinylcyclohex-1-ene, vinylcycloheptane, vinylcyclooctane, vinylcyclononane, vinylcyclodecane, vinylcycloundecane, vinylcyclododecane, 5-vinylnorbornane, 5-vinyl-2-norbornene, allylcyclohexane, and allylcyclooctane.

16 . The process of claim 15 , wherein the one or more cyclic C 6 -C 32 alpha-olefins are selected from vinylcyclobutane, vinylcyclopentane, vinylcyclohexane, and 4-vinylcyclohex-1-ene.

17 . The process of claim 1 , wherein the one or more C 4 -C 32 linear and/or branched alpha-olefins are selected from 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 1-heneicosene, 1-docosene, 1-tricosene, 1-tetracosene, 1-pentacosene, 1-hexacosene, 1-heptacosene, 1-octacosene, 1-nonacosene, 1-triacontene, 4-methyl-1-pentene, 3-methyl-1-pentene, 5-methyl-1-nonene, and 3,5,5-trimethyl-1-hexene.

18 . The process of claim 17 , wherein the one or more C 4 -C 32 linear and/or branched alpha-olefins are selected from 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 4-methyl-1-pentene, 3-methyl-1-pentene, 5-methyl-1-nonene, and 3,5,5-trimethyl-1-hexene.

19 . The process of claim 1 , wherein the one or more C 4 -C 32 linear alpha-olefins comprise C 4 -C 20 linear alpha-olefins, C 4 -C 12 linear alpha-olefins, C 4 -C 8 linear alpha-olefins, C 5 -C 8 linear alpha olefins, or C 5 -C 6 linear alpha olefins, wherein the one or more C 4 -C 32 branched alpha-olefins comprise C 5 -C 20 branched alpha-olefins, C 5 -C 12 branched alpha-olefins, C 5 -C 10 branched alpha-olefins, C 6 -C 9 branched alpha olefins, or C 6 -C 8 branched alpha olefins, and wherein the one or more C 6 -C 32 cyclic alpha-olefins comprise C 6 -C 20 cyclic alpha-olefins, C 6 -C 14 cyclic alpha-olefins, or C 8 -C 12 cyclic alpha-olefins.

20 - 41 . (canceled)

42 . The process of claim 1 , wherein the metallocene compound is represented by formula (I):

wherein:
R 1 , R 2 , and R 3 are each independently hydrogen or a substituted or unsubstituted linear, branched, or cyclic C 1 -C 20 hydrocarbyl or silylcarbyl group;
R 4 and R 5 are each independently a substituted or unsubstituted linear, branched, or cyclic C 1 -C 30 hydrocarbyl or silylcarbyl group where R 4 and R 5 , taken together with the carbon atoms in the first cyclopentadienyl ring to which they are directly connected, collectively form one or more substituted or unsubstituted rings annelated to the first cyclopentadienyl ring;
R 12 , R 13 , R 14 , R 15 , and R 16 are each independently a hydrogen or a substituted or unsubstituted linear, branched, or cyclic C 1 -C 20 hydrocarbyl, silylcarbyl, or germanyl group, and at least four of R 12 , R 13 , R 14 , R 15 , and R 16 are not hydrogen;
M is a Group 3, 4, or 5 transition metal having an integer coordination number of v, wherein v is 3, 4, or 5;
each X is independently a halogen, a hydride, an amide, an alkoxide, a sulfide, a phosphide, a diene, an amine, a phosphine, an ether, or a C 1 -C 20 substituted or unsubstituted linear, branched, or cyclic hydrocarbyl group, or optionally two or more X moieties may together form a fused ring or ring system; and
m is an integer equal to v-2.

43 . The process of claim 1 , wherein the metallocene compound is represented by formula (II):

wherein:
R 1 , R 2 , and R 3 are each independently hydrogen or a substituted or unsubstituted linear, branched, or cyclic C 1 -C 20 hydrocarbyl group;
R 6 , R 7 , R 17 , and R 18 are each independently hydrogen, a substituted or unsubstituted linear, branched, or a cyclic C 1 -C 30 hydrocarbyl group, or R 6 and R 7 , R 7 and R 17 , or R 17 and R 18 taken together with the carbon atoms in the indenyl ring to which they are directly connected, collectively form one or more substituted or unsubstituted rings annelated to the indenyl ring;
R 12 , R 13 , R 14 , and R 15 are each independently a substituted or unsubstituted linear, branched, or cyclic C 1 -C 20 hydrocarbyl group;
R 16 is hydrogen or a substituted or unsubstituted linear, branched, or cyclic C 1 -C 20 hydrocarbyl group or silylcarbyl group;
each X is independently a halogen, a hydride, an amide, an alkoxide, a sulfide, a phosphide, a diene, an amine, a phosphine, an ether, a C 1 -C 20 substituted or unsubstituted linear, branched, or cyclic hydrocarbyl group, or two or more X moieties together form a fused ring or ring system;
M is a Group 3, 4, or 5 transition metal having an integer coordination number of v, wherein v is 3, 4, or 5; and
m is an integer equal to v-2.

44 . The process of claim 1 , wherein the metallocene compound is represented by formula (III):

wherein:
R 1 and R 2 are hydrogen;
R 23 and R 19 comprise, independently, Group 14 atoms, such as C, Ge, or Si (e.g., R 23 includes C and R 19 includes C or Si);
R 20 , R 21 , and R 22 are independently hydrogen or a substituted or unsubstituted linear, branched, or cyclic C 1 -C 20 hydrocarbyl group and at least two of R 20 , R 21 , and R 22 are independently a substituted or unsubstituted linear, branched, or cyclic C 1 -C 20 hydrocarbyl group;
R 6 , R 7 , R 17 , and R 18 are each independently hydrogen, a substituted or unsubstituted linear, branched, or cyclic C 1 -C 30 hydrocarbyl group, or R 6 and R 7 , R 7 and R 17 , or R 17 and R 18 , taken together with the carbon atoms in the indenyl ring to which they are directly connected, collectively form one or more substituted or unsubstituted rings annelated to the indenyl ring;
R 12 , R 13 , R 14 , R 15 , and R 16 are each independently a substituted or unsubstituted linear, branch

Assignees

• Exxonmobil Technology & Engineering Company

Inventors

• Canich Jo Ann M
• Zabula Alexander V
• Younker Jarod M
• Jiang Peijun
• Mccullough Laughlin G
• Carpenter Alex E
• Singleton Danielle G
• Dupper Torin J
• Vincent Dwight L
• Kheir Sarah A

Classifications

• C08F2410/01

  Additive used together with the catalyst, excluding compounds containing Al or B · CPC title

• C08F4/65927

  two cyclopentadienyl rings being mutually bridged · CPC title

• C08F2420/10

  Heteroatom-substituted bridge, i.e. Cp or analog where the bridge linking the two Cps or analogs is substituted by at least one group that contains a heteroatom · CPC title

• C10N2040/04

  Oil-bath; Gear-boxes; Automatic transmissions; Traction drives · CPC title

• C07C2602/42

  the bicyclo ring system containing seven carbon atoms · CPC title