IP Library Granted Patent US 9,963,401
Granted Patent B2
US 9,963,401 · App. 14/997,285 · Granted May 8, 2018

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 9,963,401
App. No.
14/997,285
Granted
May 8, 2018
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 (37)

1. A method for preparing a phase change material comprising:

feeding naturally occurring fatty acids and esters to a reactor containing a liquid phase, a gas phase, and a catalyst comprising 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;

controlling an intracatalyst temperature gradient within the reactor to reduce thermal decarboxylation relative to oxygen hydrogenolysis; and

withdrawing a liquid product stream from the reactor;

wherein 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 temperature in the reactor is controlled to be within 315° C. to 343° C.

3. 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.

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, coconut oil, sunflower oil, palm oil, palm kernel oil, rapeseed oil, or a combination of any two or more thereof.

5. 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.

6. 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.

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

8. 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.

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

10. The method of claim 1 , wherein

temperature in the reactor is controlled to be within 315° C. to 343° C.;

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.

11. The method of claim 1 , wherein

temperature in the reactor is controlled to be within 315° C. to 343° C.;

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.

12. 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.

13. The method of claim 12 , wherein the further processing steps comprise distilling the liquid product stream.

14. The method of claim 13 , wherein temperature in the reactor is controlled to be within 315° C. to 343° C.

15. 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 the liquid from the slurry stream back to the reactor.

16. A method for preparing a phase change material comprising:

feeding naturally occurring fatty acids and esters to a reactor containing a liquid phase, a gas phase, and a catalyst comprising nickel, molybdenum, cobalt, and/or tungsten;

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 said gas stream;

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

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

17. The method of claim 16 , comprising further processing the liquid hydrocarbon stream to recover at least a portion of the even carbon numbered paraffins from the stream to produce a phase change material.

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 →
PATENT SECURITY AGREEMENT Recorded Jun 19, 2021
From: REG SYNTHETIC FUELS, LLC
To: UMB BANK, N.A., AS COLLATERAL TRUSTEE
Reel/Frame 056628/0673 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2018
From: SYNTROLEUM CORPORATION
To: REG SYNTHETIC FUELS, LLC
Reel/Frame 044751/0441 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2018
From: ABHARI, RAMIN; TOMLINSON, H. LYNN; GRUVER, VLADIMIR
To: SYNTROLEUM CORPORATION
Reel/Frame 044751/0481 →
Continuity (3)
Continuation 13466813 · May 8, 2012
Division 12331906 · Dec 10, 2008
Related Publication 20160264491A1 · Sep 15, 2016