IP Library › Granted Patent US 11,639,320
Granted Patent B1
US 11,639,320 · App. 17/750,663 · Granted May 2, 2023

Process for the production of renewable distillate-range hydrocarbons

Inventors: Bong Kyu Chang (Novato, CA); Hye-Kyung Cho Timken (Albany, CA); Michelle K. Young (Marvel, TX)
Assignee: Chevron U.S.A. Inc.
C07C2/22C10G50/02C07C2527/06C07C2527/122C07C2527/125C07C2527/128
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,639,320
App. No.
17/750,663
Granted
May 2, 2023
Kind
B1
Abstract

A process for producing renewable distillate-range hydrocarbons is provided. The process includes dehydrating a renewable C2-C6 alcohol feedstock to produce an olefin, oligomerizing the olefin the presence of a halometallate ionic liquid catalyst to produce an oligomer product and hydrogenating the oligomer product or fractions thereof to produce saturated distillate-range hydrocarbons.

Claims (24)

1. A process for producing distillate-range hydrocarbons, the process comprising:

(a) dehydrating bio-alcohols in a fermentation stream comprising isobutanol to form an olefin stream and a water stream wherein the dehydration process is conducted at selected process conditions sufficient to achieve conversion of the bio-alcohols that is 95% or more and wherein an amount of oxygenates in the olefin stream is less than 1 wt. %;

(b) separating the olefin stream from the water stream;

(c) contacting the olefin stream with a halometallate ionic liquid catalyst, the halometallate ionic liquid catalyst comprising an organic cation and a halometallate anion, in an oligomerization reactor under oligomerization conditions to form a mixture comprising the halometallate ionic liquid catalyst and an oligomer product, wherein at least 50 wt. % of the oligomer product has boiling point distribution of from 150° C. to 400° C.; and

(d) separating the oligomer product from the halometallate ionic liquid catalyst.

2. The process of claim 1 , wherein the bio-alcohols in the fermentation stream contain anywhere from 2 to 4 carbon atoms.

3. The process of claim 1 , wherein dehydrating comprises reacting the bio-alcohols in the fermentation stream over a solid acid catalyst at a temperature of from 300° C. to 500° C. and a pressure of from 100 kPa to 3447 kPa.

4. The process of claim 1 , wherein the organic cation of the halometallate anion comprises an ammonium cation, a pyrrolidinium cation, a pyridinium cation, an imidazolium, a phosphonium cation, or any combination thereof.

5. The process of claim 1 , wherein the halometallate anion contains a metal selected from Al, Ga, In, Mn, Fe, Co, Ni, Cu, Zn, or any combination thereof, and a halide selected from F, Cl, Br, I, or any combination thereof.

6. The process of claim 1 , wherein the halometallate anion is a chloroaluminate.

7. The process of claim 1 , wherein the halometallate ionic liquid comprises 1-butylpriyidinium chloroaluminate.

8. The process of claim 1 , wherein the oligomerization conditions include a temperature of from 35° C. to 130° C., and a pressure of from 400 psig to 600 psig (2.8 MPa to 4.1 MPa).

9. The process of claim 1 , further comprising feeding a co-catalyst to the oligomerization reactor.

10. The process of claim 9 , wherein the co-catalyst is HCl or a chloroalkane.

11. The process of claim 1 , further comprising feeding an inert hydrocarbon diluent to the oligomerization reactor.

12. The process of claim 11 , wherein the inert hydrocarbon diluent is a C6-C12 alkane.

13. The process of claim 1 , wherein the oligomer product comprises at least 50 mol. % ti-substituted olefins and tetra-substituted olefins.

14. The process of claim 1 , wherein the oligomer product comprises at least 30 wt. % C20+ olefins.

15. The process of claim 1 , further comprising fractionating the oligomer product at a selected fractionation temperature to obtain individual fractions, a fraction containing distillate-range olefins boiling at or higher than the fractionation temperature and a light fraction boiling at or below the fractionation temperature.

16. The process of claim 15 , wherein the fractionation temperature is in a range of from 100° C. to 140° C. or from 140° C. to 180° C.

17. The process of claim 15 , further comprising hydrogenating the distillate-range olefins to form distillate-range paraffins.

18. The process of claim 17 , wherein the distillate-range paraffins are in the diesel fuel range or jet fuel range.

19. The process of claim 1 , further comprising hydrogenating the oligomer product to form a hydrogenated oligomer product.

20. The process of claim 19 , further comprising separating the hydrogenated oligomer product into a saturated jet-range hydrocarbons stream and a saturated diesel-range hydrocarbons stream.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 23, 2022
From: CHANG, BONG KYU; TIMKEN, HYE-KYUNG CHO; YOUNG, MICHELLE K.
To: CHEVRON U.S.A. INC.
Reel/Frame 059981/0795 →
Cited By (2)
US 12,528,999 US 12,618,016