IP Library › Granted Patent US 12,049,434
Granted Patent B2
US 12,049,434 · App. 18/118,674 · Granted Jul 30, 2024

Even carbon number paraffin composition and method of manufacturing same

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
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Quick Facts
Patent No.
US 12,049,434
App. No.
18/118,674
Granted
Jul 30, 2024
Kind
B2
Abstract

Paraffin compositions including mainly even carbon number paraffins, and a method for manufacturing the same, is disclosed herein. In one embodiment, the method involves contacting naturally occurring fatty acid/glycerides with hydrogen in a slurry bubble column reactor containing bimetallic catalysts with equivalent particle diameters from about 10 to about 400 micron. The even carbon number compositions are particularly useful as phase change material.

Claims (41)

1. A method comprising:

feeding naturally occurring fatty acids and esters to a slurry bubble column 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, and the catalyst has an equivalent particle diameter of about 10 microns to about 400 microns;

partially hydrogenating/hydrogenolyzing the naturally occurring fatty acids and esters in the slurry bubble column reactor to produce a partially converted product;

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

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

withdrawing a liquid product stream from the reactor;

wherein

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

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

the liquid product stream comprises at least 75 wt % even carbon number paraffins selected from the C 12 -C 24 range.

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

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 30 to 80 microns.

14. The method of claim 13 , wherein the liquid product stream comprises at least 80 wt % even carbon number paraffins selected from the C 12 -C 24 range.

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 , comprising further processing the liquid product stream to recover at least a portion of the even carbon numbered paraffins and produce a phase change material.

19. The method of claim 18 , wherein the further processing comprises distilling the liquid product stream.

20. The method of claim 1 , wherein transferring the partially converted product to the fixed-bed reactor comprises filtering a slurry stream from the slurry bubble column reactor to remove and recycle the catalyst and part of a liquid from the slurry stream back to the slurry bubble column reactor.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 18, 2024
From: ABHARI, RAMIN; TOMLINSON, H. LYNN; GRUVER, VLADIMIR
To: SYNTROLEUM CORPORATION
Reel/Frame 067763/0902 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 18, 2024
From: SYNTROLEUM CORPORATION
To: REG SYNTHETIC FUELS, LLC
Reel/Frame 067764/0040 →
Continuity (7)
Continuation 17404557 · Aug 17, 2021
Continuation 16896486 · Jun 9, 2020
Continuation 15973064 · May 7, 2018
Continuation 14997285 · Jan 15, 2016
Continuation 13466813 · May 8, 2012
Division 12331906 · Dec 10, 2008
Related Publication 20230219867A1 · Jul 13, 2023