IP Library Granted Patent US 11,186,785
Granted Patent B2
US 11,186,785 · App. 16/928,900 · Granted Nov 30, 2021

Bio-based synthetic fluids

Inventors: Ramin Abhari (Bixby, OK); E. Gary Roth (Bristow, OK); Peter Z. Havlik (Tulsa, OK); H. Lynn Tomlinson (Leonard, OK)
Assignee: REG Synthetic Fuels, LLC
C10G50/00A01N25/02C09K8/32C09K8/34C09K8/64C09K21/08C10G3/00C10G3/50C10G49/00C10G49/02C10G50/02C10M105/04C10M105/52C11D7/241E21B43/26C10G2300/1011C10G2300/1014C10G2300/1018C10N2040/20Y02P30/20
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 11,186,785
App. No.
16/928,900
Granted
Nov 30, 2021
Kind
B2
Abstract

A method is provided involving altering the viscosity of bio-derived paraffins to produce a paraffinic fluid, where the altering step includes chlorinating the bio-derived paraffins; the bio-derived paraffins include a hydrodeoxygenated product produced by hydrodeoxygenating a bio-based feed where the bio-based feed includes bio-derived fatty acids, fatty acid esters, or a combination thereof; the bio-derived paraffins include n-paraffins; and the n-paraffins have a biodegradability of at least 40% after about 23 days of exposure to microorganisms. Also provided are methods of protecting and/or cleaning a substance by applying the paraffinic fluid.

Claims (28)

1. A method for producing a paraffinic fluid with selective solvency having a Kauri-Butanol value from about 19 to about 25, an aniline point of about 80° C. or greater, and a kinematic viscosity of less than about 10 cSt at 40° C., the method comprising

hydrodeoxygenating a bio-based feed to produce a hydrodeoxygenated product;

at least partially hydroisomerizing the hydrodeoxygenated product over a bifunctional catalyst at a hydrogen gas-to-oil (GOR) ratio in the range of about 100 NL/L to about 1,000 NL/L and at a liquid hourly space velocity (LHSV) in the range of about 0.2 hr −1 to about 5 hr −1 to produce a hydroisomerized product with a ratio of isoparaffins-to-normal paraffins in the range of about 1:1 to about 30:1; and

fractionating the hydroisomerized product into different fractionation cuts such that one or more fractionation cuts have

a ratio of isoparaffins-to-normal paraffins in the range of about 1:1 to about 30:1 where at least about 80 wt % of the isoparaffins are mono-methyl branched paraffins and the mono-methyl branched paraffins comprise less than about 30 wt % terminal branched isoparaffins,

a biodegradability of at least about 40% after about 23 days of exposure to microorganisms,

a Kauri-Butanol value from about 19 to about 25,

an aniline point of about 80° C. or greater, and

a kinematic viscosity of less than about 10 cSt at 40° C.;

wherein the bio-based feed comprises bio-derived fatty acids, fatty acid esters, or a combination thereof; and

wherein the paraffinic fluid comprises the one or more fractionation cuts.

2. The method of claim 1 , wherein the bio-derived fatty acids, fatty acid esters, or a combination thereof comprises algae oils, beef tallow, camelina oil, canola oil, rapeseed oil, castor oil, choice white grease, coconut oil, coffee bean oil, corn oil, cottonseed oil, fish oils, hemp oil, Jatropha oil, linseed oil, mustard oil, palm oil, palm kernel oil, poultry fat, soybean oil, sunflower oil, tall oil, tall oil fatty acid, Tung oil, used cooking oils, yellow grease, products of the food industry, or a combination of any two or more thereof.

3. The method of claim 1 , wherein the bio-derived fatty acids, fatty acid esters, or a combination thereof comprise 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 one or more fractionation cuts comprise greater than 99 wt % saturates.

5. The method of claim 1 , wherein the one or more fractionation cuts have a pour point of less than −10° C.

6. The method of claim 1 , wherein the one or more fractionation cuts have a pour point of less than −15° C.

7. The method of claim 1 , wherein the one or more fractionation cuts have a pour point of less than −20° C.

8. The method of claim 1 , wherein the one or more fractionation cuts have an aniline point of about 80° C. to about 98° C.

9. The method of claim 1 , wherein the one or more fractionation cuts comprise less than about 0.5 wt % aromatics.

10. The method of claim 1 , wherein the one or more fractionation cuts comprise less than 0.1 wt % aromatics.

11. The method of claim 1 , wherein the one or more fractionation cuts are free of benzene.

12. The method of claim 1 , wherein the one or more fractionation cuts have a flash point above 60° C.

13. The method of claim 1 , wherein the one or more fractionation cuts have a ratio of isoparaffins-to-normal paraffins is between about 5:1 and about 20:1.

14. The method of claim 1 , wherein the paraffinic fluid has a pour point of less than −10° C.

15. The method of claim 1 , wherein the paraffinic fluid has a biodegradability of at least about 40% after about 23 days of exposure to microorganisms.

16. The method of claim 1 , wherein the paraffinic fluid has an aniline point of about 80° C. to about 98° C.

17. The method of claim 1 , wherein the paraffinic fluid has less than about 0.5 wt % aromatics.

18. The method of claim 1 , wherein the paraffinic fluid has a flash point above 60° C.

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 Sep 23, 2021
From: ABHARI, RAMIN; ROTH, E. GARY; HAVLIK, PETER Z.; TOMLINSON, H. LYNN
To: SYNTROLEUM CORPORATION
Reel/Frame 057582/0080 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 23, 2021
From: SYNTROLEUM CORPORATION
To: REG SYNTHETIC FUELS, LLC
Reel/Frame 057582/0200 →
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 (6)
Continuation 16025773 · Jul 2, 2018
Division 15270646 · Sep 20, 2016
Division 14598966 · Jan 16, 2015
Division 13871972 · Apr 26, 2013
Provisional Application 61809183 · Apr 5, 2013
Related Publication 20210024835A1 · Jan 28, 2021