Sustainable aviation fuel from normal alpha olefin byproducts and process for same

Patent metadata

Field	Value
Publication number	US-12540287-B2
Application number	US-202318462558-A
Country	US
Kind code	B2
Filing date	Sep 7, 2023
Priority date	Sep 7, 2023
Publication date	Feb 3, 2026
Grant date	Feb 3, 2026

Abstract

Process for making sustainable aviation fuel (SAF) from specific bio-ethylene oligomerization reactions producing a C 4 -C 8 alpha-olefin and a by-product mixture of C 10 olefins. This mixed decene stream is upgraded by further oligomerizing with at least one C 4 -C 6 alpha-olefin to provide a C 16− olefin stream, which is hydrogenated to C 16− paraffins which is used to form a SAF. Employing bio-ethylene to produce the mixed decene stream, which is relatively low-value due in part to its non-selectivity, leverages that non-selectivity into a desirable sustainable aviation fuel product where the low selectivity is preferable. These and other embodiments and aspects are described herein.

First claim

What is claimed is:

1 . A process for making a sustainable aviation fuel, the process comprising:
(a) providing a bio-ethylene feed, at least a portion of which is derived from dehydration of biomass ethanol; (b) contacting the bio-ethylene feed with a first catalyst system comprising a first oligomerization catalyst to form an oligomerization product comprising at least one C 4 -C 8 alpha-olefin and a mixture of decenes; (c) separating the mixture of decenes from the oligomerization product; (d) (i) contacting the mixture of decenes with at least one C 6− alpha-olefin in the presence of a second catalyst system comprising a second oligomerization catalyst, or (ii) contacting the mixture of decenes with at least one C 8− alpha-olefin in the presence of a second catalyst system comprising a metathesis catalyst, to provide a C 16− olefin stream; (e) hydrogenating the C 16− olefin stream in the presence of a first hydrogenation catalyst to provide C 16− paraffins; and (f) using the C 16− paraffins as a component to form a sustainable aviation fuel.

2 . The process for making a sustainable aviation fuel according to claim 1 , wherein the at least one C 6− alpha-olefin comprises ethylene, propylene, 1-butene, 1-pentene, 1-hexene, or a combination thereof.

3 . The process for making a sustainable aviation fuel according to claim 1 , wherein the at least one C 8− alpha-olefin comprises propylene, 1-butene, 2-butene, isobutylene, 1-pentene, 1-hexene, 3,3-dimethyl-1-butene, 1-octene, or a combination thereof.

4 . The process for making a sustainable aviation fuel according to claim 1 , wherein the oligomerization product comprises 1-butene, 1-hexene, 1-octene, dodecenes, tetradecenes, or any combination thereof.

5 . The process for making a sustainable aviation fuel according to claim 1 , wherein:
(a) the sustainable aviation fuel is certified as compliant with the Carbon Offsetting and Reduction Scheme for International Aviation (CORSIA) sustainability criteria in accordance with the International Sustainability and Carbon Certification (ISCC) CORSIA certification system; or (b) the sustainable aviation fuel is certified as a Lower Carbon Aviation Fuel (LCAF) in accordance with the International Sustainability and Carbon Certification (ISCC) LCAF certification system; wherein the certification is based upon the weight or fraction of the sustainable aviation fuel attributable to the biomass ethanol determined by mass balance and a free attribution method.

6 . The process for making a sustainable aviation fuel according to claim 1 , wherein the oligomerization product comprises:
at least 60 mol % 1-hexene, at least 60 mol % 1-octene, or at least 60 mol % 1-hexene and 1-octene combined; or from 70 wt. % to 99.8 wt. % hexene or from 70 wt. % to 99.8 wt. % octene, and at least 0.2 wt. % of the mixture of decenes.

7 . The process for making a sustainable aviation fuel according to claim 1 , wherein the mixture of decenes comprises 1-decene, 2-butyl-1-hexene, 3-propyl-1-heptene, 4-ethyl-1-octene, 5-methyl-1-nonene, 4-decene, 5-decene, or any combination thereof.

8 . The process for making a sustainable aviation fuel according to claim 1 , wherein the mixture of decenes comprises from 76 mol % to 95 mol % C 10 monoolefins.

9 . The process for making a sustainable aviation fuel according to claim 1 , wherein the first catalyst system, the second catalyst system, or both comprise independently a chromium-based catalyst, a metallocene-based catalyst, a Ziegler-Natta based catalyst, a metal-oxide supported Group 6-10 transition metal-based catalyst, or a combination thereof.

10 . The process for making a sustainable aviation fuel according to claim 9 , wherein the first catalyst system, the second catalyst system, or both further comprise a metal alkyl compound selected from an organoaluminum compound, an organoaluminoxane, an organoboron compound, an organozinc compound, an organomagnesium compound, an organolithium compound, or any combination thereof.

11 . The process for making a sustainable aviation fuel according to claim 1 , wherein the first catalyst system, the second catalyst system, or both comprise independently a chromium-based catalyst, and the chromium-based catalyst comprises (a) a chromium-containing compound, (b) a heteroatomic ligand, (c) a metal alkyl compound, and (d) optionally, a diluent.

12 . The process for making a sustainable aviation fuel according to claim 11 , wherein the heteroatomic ligand is selected from a pyrrole compound, a diphosphino aminyl compound, an N 2 -phosphinyl amidine compound, an N 2 -phosphinyl formamidine compound, or combinations thereof.

13 . The process for making a sustainable aviation fuel according to claim 11 , wherein the heteroatomic ligand is selected from a pyrrole compound having the Formula P1 or Formula I1:

wherein R 2p , R 3p , R 4p , and R 5p of Formula P1 and R 2i , R 3i , R 4i , R 5i , R 6i , and R 7i of Formula I1 are selected independently from a C 1 to C 18 organyl group, a C 1 to C 18 hydrocarbyl group, or a C 3 to C 60 silyl group.

14 . The process for making a sustainable aviation fuel according to claim 11 , wherein the heteroatomic ligand is a diphosphino aminyl moiety having Structure PNP2:

wherein the R 1n , R 2n , R 3n , R 4n , and R 5n independently are: a C 1 to C 30 organyl group; a C 1 to C 30 organyl group comprising inert functional groups; a C 1 to C 30 hydrocarbyl group; a C 1 to C 30 alkyl group; a C 6 to C 30 aromatic group; a phenyl group or a C 6 to C 30 substituted phenyl group; or a substituted or an unsubstituted C 1 to C 20 alkyl group.

15 . The process for making a sustainable aviation fuel according to claim 14 , wherein any substituent of a substituted group is selected from a halide, a C 1 to C 10 hydrocarbyl group, or a C 1 to C 10 hydrocarboxy group.

16 . The process for making a sustainable aviation fuel according to claim 11 , wherein the heteroatomic ligand is selected from an N 2 -phosphinyl formamidine compound having Structure NPF1, or an N 2 -phosphinyl formamidine compound having Structure NPA1:

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are independently a C 1 to C 30 organyl group, a C 1 to C 30 organyl group consisting essentially of inert functional groups, or a C 1 to C 30 hydrocarbyl group.

17 . The process for making a sustainable aviation fuel according to claim 11 , wherein the diluent comprises a hydrocarbon, a halogenated hydrocarbon, or combinations thereof.

18 . The process for making a sustainable aviation fuel according to claim 1 , wherein the first catalyst system, the second catalyst system, or both comprise independently:
(a) a chromium-containing compound, a pyrrole compound, an organoaluminum compound, and optionally a halide containing compound; (b) a chromium-containing compound, a diphosphino aminyl compound, and an organoaluminum compound; (c) a chromium-containing compound complexed to a diphosphino aminyl compound, and an organoaluminum compound; (d) a chromium-containing compound, an N 2 -phosphinyl amidine compound, and an organoaluminum compound; (e) a chromium-containing compound complexed to an N 2 -phosphinyl amidine com

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

• Webster-Gardiner Michael S
• Hillier James
• Khankal Reza
• Fern Jared
• Bischof Steven M
• Malinski Thomas J
• Gee Jeffery C
• Kerns Spencer A

Classifications

• C10L2270/04

  for turbines, planes, power generation · CPC title

• C07C2531/24

  Phosphines · CPC title

• C07C2531/22

  Organic complexes · CPC title

• B01J2231/20

  Olefin oligomerisation or telomerisation · CPC title

• C07C5/03

  of non-aromatic carbon-to-carbon double bonds · CPC title