IP Library Granted Patent US 11,001,774
Granted Patent B2
US 11,001,774 · App. 16/284,827 · Granted May 11, 2021

Biorenewable kerosene, jet fuel, jet fuel blendstock, and method of manufacturing

Inventors: Ramin Abhari (Bixby, OK); David A. Slade (Ames, IA); H. Lynn Tomlinson (Tulsa, OK); Erik Ashby (S. San Francisco, CA); Nate Green (Ames, IA); Caroline Golden (Baton Rouge, LA)
Assignee: REG SYNTHETIC FUELS, LLC
C10L1/08C10G3/50C10G3/54C10L1/04C10L5/361C10L5/365C10L11/04C10G2300/1011C10G2300/1014C10G2300/304C10G2400/04C10G2400/08C10L2200/0469C10L2230/06C10L2270/026C10L2270/04Y02E50/10Y02P30/20Y02T50/678
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Quick Facts
Patent No.
US 11,001,774
App. No.
16/284,827
Granted
May 11, 2021
Kind
B2
Abstract

The present technology provides compositions that include at least about 98 weight percent (“wt %”) n-paraffins which, among other surprising features, may be suitable for use as a diesel fuel, an aviation fuel, a jet fuel blendstock, a blendstock to reduce the cloud point of a diesel fuel, a fuel for portable heaters, and/or as a charcoal lighter fluid. The composition includes at least about 98 wt % C 7 -C 12 n-paraffins, where at least about 10 wt % of composition includes n-decane, at least about 20 wt % of the composition includes n-dodecane, and at least about 75 wt % of the composition includes even carbon number paraffins. The composition also includes less about 0.1 wt % oxygenates and less than about 0.1 wt % aromatics. The composition may be produced by a process that includes hydrotreating a biorenewable feedstock comprising at least one of palm kernel oil, coconut oil, babassu oil, microbial oil, or algal oil.

Claims (65)

1. A method of producing a composition, the method comprising

contacting a feed stream comprising a biorenewable feedstock with a hydrotreatment catalyst in a fixed bed hydrotreatment reactor to produce a hydrotreated product; and

fractionating the hydrotreated product to produce the composition;

wherein

the biorenewable feedstock comprises at least one of palm kernel oil, coconut oil, babassu oil, microbial oil, or algal oil;

the hydrotreatment catalyst comprises a monometallic Mo catalyst;

the fixed bed hydrotreatment reactor

is at a temperature less than about 750° F.; and

is at a pressure from about 200 psig to about 4,000 psig; and

the composition comprises

at least 98 wt % C 7 -C 12 n-paraffins, wherein at least 10 wt % of composition comprises n-decane, at least 20 wt % of the composition comprises n-dodecane, and at least 75 wt % of composition comprises even carbon number paraffins;

less than 0.1 wt % oxygenates; and

less than 0.1 wt % aromatics.

2. The method of claim 1 , wherein the liquid hourly space velocity of the biorenewable feedstock through the fixed bed hydrotreatment reactor is from about 0.2 hr −1 to about 10.0 hr −1 .

3. The method of claim 1 , wherein the biorenewable feedstock further comprises animal fats, animal oils, plant fats, plant oils, vegetable fats, vegetable oils, or greases.

4. The method of claim 1 , wherein the biorenewable feedstock further comprises one or more of animal fats, poultry oil, soybean oil, canola oil, carinata oil, rapeseed oils, palm oil, jatropha oil, castor oil, camelina oil, seaweed oil, halophile oils, rendered fats, restaurant greases, brown grease, yellow grease, waste industrial frying oils, fish oils, tall oil, and tall oil fatty acids.

5. The method of claim 1 , wherein the biorenewable feedstock further comprises one or more of carinata oil, animal fats, restaurant greases, brown grease, yellow grease, and waste industrial frying oils.

6. The method of claim 1 , wherein the feed stream further comprises a diluent and the volume ratio of diluent to biorenewable feedstock falls within the range from about 0.5:1 to about 20:1.

7. The method of claim 1 , wherein the method comprises fractionating the hydrotreated product to produce the composition and one or more C 14 -C 22 n-paraffin fractions comprising at least about 90 wt % C 14 -C 22 n-paraffins.

8. The method of claim 7 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % C 14 -C 16 n-paraffins.

9. The method of claim 7 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % C 14 -C 18 n-paraffins.

10. The method of claim 7 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % C 16 -C 18 n-paraffins.

11. The method of claim 7 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % C 18 -C 20 n-paraffins.

12. The method of claim 7 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % n-tetradecane.

13. The method of claim 7 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % n-hexadecane.

14. The method of claim 7 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % n-octadecane.

15. The method of claim 7 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % n-icosane.

16. The method of claim 7 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % n-docosane.

17. The method of claim 1 , wherein the method comprises fractionating the hydrotreated product to produce the composition and two or more C 14 -C 22 n-paraffin fractions, wherein each C 14 -C 22 n-paraffin fraction independently comprises at least about 90 wt % C 14 -C 22 n-paraffins.

18. The method of claim 17 , wherein the two or more C 14 -C 22 n-paraffin fractions comprise

a fraction comprising at least about 90 wt % n-tetradecane;

a fraction comprising at least about 90 wt % n-hexadecane; and

a fraction comprising at least about 90 wt % n-octadecane.

19. A method of producing a composition, the method comprising

contacting a feed stream comprising a biorenewable feedstock with a hydrotreatment catalyst in a fixed bed hydrotreatment reactor to produce a hydrotreated product; and

fractionating the hydrotreated product to produce the composition;

wherein

the biorenewable feedstock comprises at least one of palm kernel oil, coconut oil, babassu oil, microbial oil, or algal oil;

the fixed bed hydrotreatment reactor

is at a temperature less than about 750° F.; and

is at a pressure from about 200 psig to about 4,000 psig;

the composition comprises

at least 98 wt % C 7 -C 12 n-paraffins, wherein at least 10 wt % of composition comprises n-decane, at least 20 wt % of the composition comprises n-dodecane, at least 75 wt % of composition comprises even carbon number paraffins, and a weight ratio of C 12 paraffins to C 11 paraffins from 3.0:1 to 1.2:1;

less than 0.1 wt % oxygenates; and

less than 0.1 wt % aromatics; and

the feed stream further comprises a diluent and a volume ratio of diluent to biorenwable feedstock falls within the range from about 0.5:1 to about 20:1.

20. The method of claim 19 , wherein the liquid hourly space velocity of the biorenewable feedstock through the fixed bed hydrotreatment reactor is from about 0.2 hr −1 to about 10.0 hr −1 .

21. The method of claim 19 , wherein the biorenewable feedstock further comprises animal fats, animal oils, plant fats, plant oils, vegetable fats, vegetable oils, or greases.

22. The method of claim 19 , wherein the biorenewable feedstock further comprises one or more of animal fats, poultry oil, soybean oil, canola oil, carinata oil, rapeseed oils, palm oil, jatropha oil, castor oil, camelina oil, seaweed oil, halophile oils, rendered fats, restaurant greases, brown grease, yellow grease, waste industrial frying oils, fish oils, tall oil, and tall oil fatty acids.

23. The method of claim 19 , wherein the biorenewable feedstock further comprises one or more of carinata oil, animal fats, restaurant greases, brown grease, yellow grease, and waste industrial frying oils.

24. The method of claim 19 , wherein the method comprises fractionating the hydrotreated product to produce the composition and one or more C 14 -C 22 n-paraffin fractions comprising at least about 90 wt % C 14 -C 22 n-paraffins.

25. The method of claim 24 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % C 14 -C 16 n-paraffins.

26. The method of claim 24 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % C 14 -C 18 n-paraffins.

27. The method of claim 24 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % C 16 -C 18 n-paraffins.

28. The method of claim 24 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % C 18 -C 20 n-paraffins.

29. The method of claim 24 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % n-tetradecane.

30. The method of claim 24 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % n-hexadecane.

31. The method of claim 24 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % n-octadecane.

32. The method of claim 24 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % n-icosane.

33. The method of claim 24 , wherein the one or more C 14 -C 22 n-paraffin fractions comprises a fraction comprising at least about 90 wt % n-docosane.

34. The method of claim 19 , wherein the method comprises fractionating the hydrotreated product to produce the composition and two or more C 14 -C 22 n-paraffin fractions, wherein each C 14 -C 22 n-paraffin fraction independently comprises at least about 90 wt % C 14 -C 22 n-paraffins.

35. The method of claim 34 , wherein the two or more C 14 -C 22 n-paraffin fractions comprise

a fraction comprising at least about 90 wt % n-tetradecane;

a fraction comprising at least about 90 wt % n-hexadecane; and

a fraction comprising at least about 90 wt % n-octadecane.

Assignments (3)
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 Apr 7, 2021
From: ABHARI, RAMIN; SLADE, DAVID A.; TOMLINSON, H. LYNN; ASHBY, ERIK; GREEN, NATE; GOLDEN, CAROLINE
To: REG SYNTHETIC FUELS, LLC
Reel/Frame 055849/0398 →
Continuity (3)
Continuation 15592080 · May 10, 2017
Provisional Application 62334968 · May 11, 2016
Related Publication 20190276758A1 · Sep 12, 2019
Cited By (3)
US 12,297,393 US 12,331,254 US 12,522,771