IP Library › Granted Patent US 10,577,291
Granted Patent B2
US 10,577,291 · App. 14/073,058 · Granted Mar 3, 2020

Methods for producing jet-range hydrocarbons

Inventors: Stanley Joseph Frey (Palatine, IL); Geoffrey William Fichtl (Chicago, IL); Paul Barger (Arlington Heights, IL); Scott M. Roney (Wheaton, IL); Steven Lee Krupa (Fox River Grove, IL); Christopher P. Nicholas (Evanston, IL)
Assignee: UOP LLC
C07C2/12B01J29/40B01J29/7034B01J29/7042B01J29/7046C07C5/03C10G50/00B01J29/7038C07C2529/89C10G2300/301C10G2300/4081C10G2400/08C10G2400/20C10G2400/22
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 10,577,291
App. No.
14/073,058
Granted
Mar 3, 2020
Kind
B2
Abstract

A method for producing jet-range hydrocarbons includes passing a stream comprising renewable C 4 olefins to an oligomerization reactor containing a zeolite catalyst to produce an oligomerized effluent, separating the oligomerized effluent to produce a jet range hydrocarbon stream and a recycle stream comprising C 8 olefins, and passing at least a portion of the recycle stream to the oligomerization reactor. A first at least about 10% of the jet-range hydrocarbon stream hydrocarbons boil between n-octane and n-undecane and wherein a second at least about 10% of the jet-range hydrocarbon stream hydrocarbons boil between n-dodecane and n-pentadecane.

Claims (25)

1. A method for producing jet-range hydrocarbons comprising:

dimerizing a stream comprising C 4 olefins to C 4 olefin oligomers over SPA or acidic ion exchange resin catalysts in a dimerization zone to provide a dimerized effluent, wherein conversion of C 4 olefins in the dimerizing step is greater than or equal to about 90% and wherein the dimerization zone is operated to favor C 8 compounds;

oligomerizing the entire dimerized effluent over a catalyst consisting of a MTT zeolite on a binder in an oligomerization reactor operated at a temperature of 171 to 197° C. and a pressure of 710 to 890 psig to produce an oligomerized effluent;

separating the oligomerized effluent to produce a jet range hydrocarbon stream and a recycle stream comprising C 8 olefins; and

passing at least a portion of the recycle stream to the oligomerization reactor,

wherein a first at least about 10 wt % of the jet-range hydrocarbon stream hydrocarbons have boiling points between the boiling point of n-octane and the boiling point of n-undecane and wherein a second at least about 10 wt % of the jet-range hydrocarbon stream hydrocarbons have boiling points between the boiling point of n-dodecane and the boiling point of n-pentadecane.

2. The method of claim 1 , wherein the C 4 olefins are derived from dehydrating a renewable alcohol with a 14 C/ 12 C ratio indicative of atmospheric carbon.

3. The method of claim 1 , wherein the dimerization zone operates at a temperature from about 93° C. to about 120° C. and a pressure of about 1000 psig to produce C 4 olefin oligomers.

4. The method of claim 1 , wherein the binder comprises alumina powder and wherein in the combined MTT zeolite and alumina powder, the MTT zeolite is present in an amount of from about 5 to about 85 wt % MTT with the balance alumina powder.

5. The method of claim 4 , wherein in the combined MTT zeolite and alumina powder the MTT zeolite is present in an amount of from about 20 to about 82 wt % MTT with the balance being the alumina powder.

6. The method of claim 1 , further comprising hydrogenating the jet range hydrocarbon stream in a hydrogenation reactor.

7. A method for producing jet-range hydrocarbons comprising:

dimerizing a stream comprising C 4 olefins to C 4 olefin oligomers over SPA or acidic ion exchange resin catalysts in a dimerization zone to provide a dimerized effluent, wherein conversion of C 4 olefins in the dimerizing step is greater than or equal to about 90% and wherein the dimerization zone is operated to favor C 8 compounds;

oligomerizing the dimerized effluent over a catalyst consisting of a MTT zeolite on a binder in an oligomerization reactor operated at a temperature of 171 to 197° C., a liquid hourly space velocity of about 0.75 to 1.50 hr −1 and a pressure of 710 to 890 psig to produce an oligomerized effluent, wherein a first at least about 10 wt.-% of the oligomerized effluent hydrocarbons have boiling points between the boiling point of n-octane and the boiling point of n-undecane and wherein a second at least about 10 wt.-% of the oligomerized effluent hydrocarbons have boiling points between the boiling point of n-dodecane and the boiling point of n-pentadecane;

separating the oligomerized effluent by distillation to produce a jet range hydrocarbon stream and a recycle stream comprising C 8 olefins; and

passing at least a portion of the recycle stream to the dimerization zone, wherein the jet-range hydrocarbons comprise between 14 and 16 wt % C 16 hydrocarbons.

8. The method of claim 7 , wherein the C 4 olefins are derived from dehydrating a renewable alcohol with a 14 C/ 12 C ratio indicative of atmospheric carbon.

9. The method of claim 7 , wherein the binder comprises alumina powder and wherein in the combined MTT zeolite and alumina powder, the MTT zeolite is present in an amount of from about 5 to about 85 wt % MTT with the balance alumina powder.

10. The method of claim 7 , wherein the binder comprises alumina powder and wherein in the combined MTT zeolite and alumina powder, the MTT zeolite is present in an amount of from about 20 to about 82 wt % MTT with the balance alumina powder.

11. The method of claim 7 , further comprising hydrogenating the jet range hydrocarbon stream in a hydrogenation reactor.

12. A method for producing jet-range hydrocarbons comprising:

dimerizing C 4 olefins over SPA or acidic ion exchange resin catalysts in a dimerization zone to produce dimers of the C 4 olefins, wherein conversion of the C 4 olefins in the dimerizing step is greater than or equal to about 90% and wherein the dimerization zone is operated to favor C 8 compounds;

oligomerizing a stream comprising the dimers of the C 4 olefins over a catalyst consisting of a MTT zeolite on a binder in an oligomerization reactor to produce an oligomerized effluent, wherein a first at least about 10 wt.-% of the oligomerized effluent hydrocarbons have boiling points between the boiling point of n-octane and the boiling point of n-undecane and wherein a second at least about 10 wt.-% of the oligomerized effluent hydrocarbons having boiling points between the boiling point of n-dodecane and the boiling point of n-pentadecane;

separating the oligomerized effluent by distillation to produce a jet range hydrocarbon stream and a recycle stream comprising C 8 olefins; and

passing at least a portion of the recycle stream to the dimerization zone.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 11, 2013
From: FREY, STANLEY JOSEPH; FICHTL, GEOFFREY WILLIAM; BARGER, PAUL; RONEY, SCOTT M.; KRUPA, STEVEN LEE; NICHOLAS, CHRISTOPHER P.
To: UOP LLC
Reel/Frame 031577/0792 →
Continuity (2)
Provisional Application 61725398 · Nov 12, 2012
Related Publication 20150045599A1 · Feb 12, 2015
Cited By (3)
US 12,516,003 US 12,528,999 US 12,618,016