IP Library Granted Patent US 12698245
Granted Patent B2
US 12698245 · App. 17/633,913 · Granted Aug 4, 2026

Processes for producing poly alpha olefins and method of analysis and apparatuses therefor

Inventors: Monica D. Lotz (Houston, TX); Frank N. Raushel (Baytown, TX); Timothy M. Boller (Houston, TX); Mark H. Li (Sugar Land, TX); Kyle G. Lewis (Houston, TX); Jennifer L. Rapp (Houston, TX)
Assignee: ExxonMobil Chemical Patents Inc.
C07C2/34C07C5/25C10M177/00C07C2531/14C07C2531/22C10M2205/0285
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Quick Facts
Patent No.
US 12698245
App. No.
17/633,913
Granted
Aug 4, 2026
Kind
B2
Abstract

The present disclosure provides processes and apparatus for producing poly alpha olefins. In at least one embodiment, a process to produce a poly alpha olefin includes introducing a first olefin monomer to a first catalyst and an activator in a first reactor to form a first reactor effluent comprising an olefin dimer and an olefin trimer. The process includes introducing the first reactor effluent to a filtration unit to form a filtration effluent, and introducing the filtration effluent to a first distillation unit to form a first distillation effluent. The process includes introducing the first distillation effluent (or a second distillation effluent) to a second catalyst in a second reactor to form a second reactor effluent comprising the olefin trimer. The process includes removing a sample at any stage of the process and introducing the sample to a gas chromatograph.

Claims (39)

1 . A process to produce a poly alpha olefin, the process comprising:

introducing a first olefin monomer to a first catalyst and an activator in a first reactor to form a first reactor effluent comprising olefin dimers;

introducing the first reactor effluent to a distillation unit to form a distillation effluent comprising olefin dimers;

introducing the distillation effluent to a second catalyst and a second olefin monomer in a second reactor to form a second reactor effluent comprising the poly alpha olefin, wherein the poly alpha olefin comprises olefin trimers;

removing a first sample from a first line extending between the first reactor and the distillation unit and removing a second sample from a second line extending between the distillation unit and the second reactor;

measuring an amount of the olefin dimers in each of the first and second samples in one or more gas chromatographs in substantially real-time, wherein the olefin dimers comprise vinylidene dimers and/or trisubstituted dimers, wherein the trisubstituted dimers comprise cis-trisubstituted dimers and/or trans-trisubstituted dimers; and

adjusting one or more process conditions to increase an amount of the trisubstituted dimers, wherein adjusting the one or more process conditions comprises adjusting one or more reactor conditions for the first reactor, adjusting one or more distillation conditions of the distillation unit, heating the first reactor effluent flowing through the first line, and/or heating the distillation effluent flowing through the second line.

2 . The process of claim 1 , further comprising: isomerizing the vinylidene dimers in the first reactor effluent, the distillation effluent, or both to form an isomerized product, wherein the isomerized product comprises trisubstituted dimers.

3 . The process of claim 2 , wherein the isomerizing comprises heating the first reactor effluent, the distillation effluent, or both.

4 . The process of claim 3 , wherein the heating comprises heating the first reactor effluent flowing through the first line with one or more first heat exchangers, heating the distillation effluent flowing through the second line with one or more second heat exchangers, or both.

5 . The process of claim 3 , wherein the first reactor effluent, the distillation effluent, or both is heated to a temperature of about 200° C. or greater.

6 . The process of claim 3 , wherein the isomerizing occurs in absence of an isomerization catalyst.

7 . The process of claim 3 , wherein the isomerizing occurs in absence of an isomerization reactor.

8 . The process of claim 6 , wherein the first catalyst is a metallocene catalyst and the second catalyst is Lewis acid.

9 . The process of claim 2 , further comprising:

introducing the isomerized product to a filtration unit to form a filtration effluent which is introduced to a first distillation unit, wherein the filtration unit has an average pore size of from about 5 to about 20 microns.

10 . The process of claim 2 , wherein the isomerized product comprises a molar ratio of cis-trisubstituted dimers to trans-trisubstituted dimers ranging from about 10:1 to about 1:10.

11 . The process of claim 2 , wherein the isomerized product comprises less than 70 wt.% of di-substituted Vinylidene dimers.

12 . The process of claim 1 , wherein the measuring in the one or more gas chromatographs comprises:

setting the one or more gas chromatographs to a first temperature from about 30° C. to about 100° C.;

holding the first temperature for a time from about 30 seconds to about 10 minutes;

increasing the first temperature to a second temperature at a rate from about 1° C. per minute to about 20° C. per minute and the second temperature is from about 60° C. to about 250° C.;

holding the second temperature for a time from about 30 seconds to about 20 minutes;

increasing the second temperature to a third temperature at a rate from about 2° C. per minute to about 40° C. per minute, and the third temperature is from about 200° C. to about 350° C.; and

holding the third temperature for a time from about 30 seconds to about 30 minutes.

13 . The process of claim 3 ; wherein:

the first temperature is about 60° C.; and the first temperature is held for about 1 minute;

the first temperature is increased to the second temperature at a rate of about 10° C. per minute and the second temperature is about 180° C.;

the second temperature is held for a time of about 5 minutes;

the second temperature is increased to the third temperature at a rate of about 25° C. per minute; and the third temperature is about 250° C.; or

the third temperature is held for a time of about 8 minutes.

14 . The process of claim 1 , wherein the one or more gas chromatographs comprises a column coated with a material comprising heavy wax, diphenyl, dimethyl polysiloxane, polyethylene glycol, or fused silica.

15 . The process of claim 1 , wherein the first and/or second sample comprises C 6 -C 20 dimers.

16 . The process of claim 1 , wherein the first and/or second sample comprises greater than 45 wt. % of trisubstituted dimer.

17 . The process of claim 16 , wherein the first and/or second sample comprises greater than 85 wt. % of trisubstituted dimer.

18 . The process of claim 1 , wherein the second olefin monomer is the same as the first olefin monomer.

19 . The process of claim 1 , wherein the poly alpha olefin further comprises dimers.

20 . The process of claim 1 , wherein adiusting the one or more process conditions comprises adiusting the one or more reactor conditions, and wherein the one or more reactor conditions comprise a reaction temperature.

21 . The process of claim 1 , wherein the first sample is measured in a first gas chromatograph and the second sample is measured in a second gas chromatograph.