Granted Patent B2

US 12,516,002 · App. 18/747,297 · Granted Jan 6, 2026

Inventors: Ramin Abhari (Bixby, OK); H. Lynn Tomlinson (Leonard, OK); Vladimir Gruver (Jenks, OK)

Assignee: REG Synthetic Fuels, LLC

C07C1/2078C07C1/22C07C9/14C07C9/15C07C9/22C09K5/063C10L1/04C07C2521/02C07C2521/04C07C2523/882C07C2523/883C07C2523/888C07C2525/00C07C2525/02C07C2527/18

Abstract

Claims (44)

1 . A method comprising:

feeding naturally occurring fatty acids and esters to a reactor containing a gas phase and a catalyst in a slurry phase, where the catalyst comprises nickel, molybdenum, cobalt, tungsten, or a combination of any two or more thereof;

at least partially hydrogenating/hydrogenolyzing the naturally occurring fatty acids and esters in the reactor;

withdrawing a gas stream from the reactor and at least partially condensing the gas stream;

separating the at least partially condensed gas stream into a second gas stream, a liquid water stream, and a liquid hydrocarbon stream; and

processing the liquid hydrocarbon stream to recover at least a portion of even carbon numbered paraffins from the liquid hydrocarbon stream to produce a phase change material;

wherein

the reactor contains the catalyst in an amount of 1% to 30% based on dry bulk catalyst volume per total slurry volume;

the reactor is controlled to be within 315° C. to 343° C. and within 200 psig to about 2,000 psig;

the liquid hydrocarbon stream comprises at least 80 wt % even carbon number paraffins selected from the C 12 -C 24 range; and

the processing comprises distilling the liquid hydrocarbon stream.

2 . The method of claim 1 , wherein the naturally occurring fatty acids and esters comprise vegetable oils, plant oils, algal oils, animal fats, tall oil fatty acid, or a combination of any two or more thereof.

3 . The method of claim 1 , wherein the naturally occurring fatty acids and esters comprise chicken fat, beef tallow, yellow grease, choice white grease, lard, soybean oil, corn oil, cottonseed oil, canola oil, coconut oil, sunflower oil, palm oil, palm kernel oil, rapeseed oil, or a combination of any two or more thereof.

4 . The method of claim 1 , wherein

the naturally occurring fatty acids and esters comprise chicken fat, beef tallow, yellow grease, choice white grease, lard, soybean oil, corn oil, cottonseed oil, canola oil, sunflower oil, palm oil, rapeseed oil, or a combination of any two or more thereof; and

the even carbon number paraffins comprise n-hexadecane and n-octadecane.

5 . The method of claim 1 , wherein

the naturally occurring fatty acids and esters comprise coconut oil, palm kernel oil, or a combination thereof; and

the even carbon number paraffins comprise n-dodecane and n-tetradecane.

6 . The method of claim 1 , wherein the even carbon number paraffins comprise n-dodecane, n-tetradecane, n-hexadecane, and n-octadecane.

7 . The method of claim 1 , wherein the catalyst has an equivalent particle diameter of about 10 microns to about 400 microns.

8 . The method of claim 7 , wherein

the naturally occurring fatty acids and esters comprise chicken fat, beef tallow, yellow grease, choice white grease, lard, soybean oil, corn oil, cottonseed oil, canola oil, sunflower oil, palm oil, rapeseed oil, or a combination of any two or more thereof; and

the even carbon number paraffins comprise n-hexadecane and n-octadecane.

9 . The method of claim 7 , wherein

the naturally occurring fatty acids and esters comprise coconut oil, palm kernel oil, or a combination thereof; and

the even carbon number paraffins comprise n-dodecane and n-tetradecane.

10 . The method of claim 7 , wherein the even carbon number paraffins comprise n-dodecane, n-tetradecane, n-hexadecane, and n-octadecane.

11 . The method of claim 1 , wherein the catalyst has an equivalent particle diameter of 30 to 80 microns.

12 . The method of claim 1 , wherein the catalyst comprises nickel-molybdenum, cobalt-molybdenum, or nickel-tungsten.

13 . The method of claim 12 , wherein the catalyst has an equivalent particle diameter of about 10 microns to about 400 microns.

14 . The method of claim 13 , wherein the catalyst has an equivalent particle diameter of 30 to 80 microns.

15 . The method of claim 14 , wherein

the naturally occurring fatty acids and esters comprise chicken fat, beef tallow, yellow grease, choice white grease, lard, soybean oil, corn oil, cottonseed oil, canola oil, sunflower oil, palm oil, rapeseed oil, or a combination of any two or more thereof; and

the even carbon number paraffins comprise n-hexadecane and n-octadecane.

16 . The method of claim 14 , wherein

the naturally occurring fatty acids and esters comprise coconut oil, palm kernel oil, or a combination thereof; and

the even carbon number paraffins comprise n-dodecane and n-tetradecane.

17 . The method of claim 14 , wherein the even carbon number paraffins comprise n-dodecane, n-tetradecane, n-hexadecane, and n-octadecane.

18 . The method of claim 1 , wherein the at least partially hydrogenating/hydrogenolyzing the naturally occurring fatty acids and esters produces a partially converted product;

the method further comprises:

transferring the partially converted product to a fixed-bed reactor; and

hydrogenating/hydrogenolyzing the partially converted product in the fixed-bed reactor.

19 . The method of claim 18 , wherein transferring the partially converted product to the fixed-bed reactor comprises filtering a slurry stream from the reactor to remove and recycle the catalyst and part of a liquid from the slurry stream back to the reactor.

Continuity (8)

References Cited (400)