IP Library Granted Patent US 10,011,783
Granted Patent B2
US 10,011,783 · App. 15/270,646 · Granted Jul 3, 2018

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
C10G50/00A01N25/02C09K8/32C09K8/34C09K8/64C09K21/08C10G3/00C10G3/50C10G49/00C10G49/02C10G50/02C10M105/04C10M105/52C11D7/241E21B43/26C10G2300/1011C10G2300/1014C10G2300/1018C10N2240/40Y02P30/20
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Quick Facts
Patent No.
US 10,011,783
App. No.
15/270,646
Granted
Jul 3, 2018
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 oligomerizing the bio-derived paraffins to produce an oligomerized product; 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 (43)

1. A method comprising altering the viscosity of bio-derived paraffins to produce a paraffinic fluid, wherein

the altering step comprises oligomerizing the bio-derived paraffins to produce an oligomerized product, wherein the oligomerized product has a kinematic viscosity of at least about 10 cSt at 40° C.;

the paraffinic fluid comprises the oligomerized product;

the bio-derived paraffins comprise a hydrodeoxygenated product produced by hydrodeoxygenating a bio-based feed where the bio-based feed comprises bio-derived fatty acids, fatty acid esters, or a combination thereof; and

the bio-derived paraffins comprise n-paraffins where the n-paraffins

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

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

2. The method of claim 1 , wherein the oligomerized product comprises less than about 1 wt % aromatics.

3. The method of claim 1 , wherein the oligomerized product comprises less than about 0.1 wt % aromatics.

4. The method of claim 1 , wherein the oligomerized product is free of benzene.

5. The method of claim 1 , wherein the altering step comprises oligomerizing bio-derived paraffins within the C 16 -C 18 range.

6. The method of claim 1 , wherein oligomerizing bio-derived paraffins comprises contacting the bio-derived paraffins with an organic peroxide to produce the oligomerized product.

7. The method of claim 6 , wherein the oligomerized product has a biodegradability of at least about 40% after about 23 days of exposure to microorganisms.

8. The method of claim 6 , wherein the oligomerized product is a dimer, trimer, tetramer, or a mixture of any two or more thereof.

9. The method of claim 6 , wherein the organic peroxide is present in an amount between about 2 wt % and about 40 wt % based on the total weight of the bio-derived paraffins and the organic peroxide.

10. The method of claim 6 , wherein the organic peroxide is of the formula

R—O—O—R′

where R and R′ are each independently H, alkyl, or aryl.

11. The method of claim 6 , wherein the organic peroxide comprises di-tert butyl peroxide, 2,5-dimethyl 2,5-di(t-butylperoxy)hexane, dicumyl peroxide, dibenzoyl peroxide, dipropyl peroxide, ethyl propyl peroxide, or tert-butyl tert-amyl peroxide.

12. The method of claim 6 , wherein the contacting is performed at a temperature between about 50° C. and about 250° C.

13. The method of claim 6 , wherein

the organic peroxide is present in an amount between about 5 wt % and about 20 wt % based on the total weight of the bio-derived paraffins and the organic peroxide; and

the contacting is performed at a temperature between about 60° C. and about 200° C.

14. The method of claim 6 , wherein the oligomerized product is used as a drilling fluid, a hydraulic fracturing fluid, a metal working fluid, a protecting agent, or a combination of any two or more thereof.

15. The method of claim 1 , wherein the bio-derived paraffins are produced by

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

at least partially hydroisomerizing the hydrodeoxygenated product to produce a hydroisomerized product;

wherein

the bio-derived paraffins comprise the hydrodeoxygenated product and the hydroisomerized product;

the hydrodeoxygenated product comprises n-paraffins;

the hydroisomerized product comprises isoparaffins where at least about 80 wt % of the isoparaffins are mono-methyl branched paraffins;

the mono-methyl branched paraffins comprise less than about 30 wt % terminal branched isoparaffins; and

the isoparaffins

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

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

16. The method of claim 15 , wherein the hydrodeoxygenated product comprises

n-paraffins in the range of about 80 wt % to about 100 wt %;

cycloparaffins in the range of about 0 wt % to about 10 wt %; and

less than about 1 wt % total aromatics.

17. 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 combinations of any two or more thereof.

18. 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.

19. The method of claim 5 , wherein oligomerizing bio-derived paraffins within the C 16 -C 18 range comprises contacting the bio-derived paraffins with an organic peroxide to produce the oligomerized product.

20. The method of claim 19 , wherein the organic peroxide comprises di-tert butyl peroxide, 2,5-dimethyl 2,5-di(t-butylperoxy)hexane, dicumyl peroxide, dibenzoyl peroxide, dipropyl peroxide, ethyl propyl peroxide, or tert-butyl tert-amyl peroxide.

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 (4)
Division 14598966 · Jan 16, 2015
Division 13871972 · Apr 26, 2013
Provisional Application 61809183 · Apr 5, 2013
Related Publication 20170009148A1 · Jan 12, 2017