IP Library Granted Patent US 11,097,994
Granted Patent B2
US 11,097,994 · App. 16/896,486 · Granted Aug 24, 2021

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 11,097,994
App. No.
16/896,486
Granted
Aug 24, 2021
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 (39)

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, and the catalyst has an equivalent particle diameter of about 10 microns to about 400 microns;

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

withdrawing a liquid product stream from the reactor;

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; 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 steps comprise distilling the liquid product stream.

20. The method of claim 1 , wherein withdrawing a liquid product stream from the 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.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Jul 1, 2022
From: UMB BANK, N.A., AS COLLATERAL TRUSTEE
To: REG SYNTHETIC FUELS, LLC; RENEWABLE ENERGY GROUP, INC.; REG SENECA, LLC; REG BIOFUELS, LLC
Reel/Frame 060562/0428 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 20, 2021
From: ABHARI, RAMIN; TOMLINSON, H. LYNN; GRUVER, VLADIMIR
To: SYNTROLEUM CORPORATION
Reel/Frame 056919/0136 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 20, 2021
From: SYNTROLEUM CORPORATION
To: REG SYNTHETIC FUELS, LLC
Reel/Frame 056919/0283 →
PATENT SECURITY AGREEMENT Recorded Jun 19, 2021
From: REG SYNTHETIC FUELS, LLC
To: UMB BANK, N.A., AS COLLATERAL TRUSTEE
Reel/Frame 056628/0673 →
Continuity (5)
Continuation 15973064 · May 7, 2018
Continuation 14997285 · Jan 15, 2016
Continuation 13466813 · May 8, 2012
Division 12331906 · Dec 10, 2008
Related Publication 20200299210A1 · Sep 24, 2020
Cited By (1)
US 12,516,002