METHOD FOR PRODUCING RENEWABLE MIDDLE-DISTILLATE COMPOSITION, USE OF THE COMPOSITION AND FUEL CONTAINING THE SAME

• US 20170183593A1
• Filed: 12/28/2016
• Published: 06/29/2017
• Est. Priority Date: 12/29/2015
• Status: Active Grant

• Current Assignee: Neste Oil Oyj
• Original Assignee: Neste Oil Oyj
• Inventors: SANDBERG, Kati, LINDBLAD, Marina, KIISKI, Ulla, MYLLYOJA, Jukka
• Granted Patent: US 10,640,721 B2
• Time in Patent Office: Days
• CPC Class Codes: B01J 23/44 Palladium
• CPC Class Codes: B01J 35/59 Membranes
• CPC Class Codes: C07C 51/353 by isomerisation; by change of size of the carbon skeleton
• CPC Class Codes: C10G 2300/202 Heteroatoms content, i.e. S, N, O, P
• CPC Class Codes: C10G 2400/04 Diesel oil
• CPC Class Codes: C10G 3/46 in combination with chromium, molybdenum, tungsten metals or compounds thereof
• CPC Class Codes: C10G 3/50 in the presence of hydrogen, hydrogen donors or hydrogen generating compounds
• CPC Class Codes: C10L 1/04 essentially based on blends of hydrocarbons
• CPC Class Codes: C10L 1/08 for compression ignition
• CPC Class Codes: C10L 10/08 for improving lubricity; for reducing wear
• CPC Class Codes: C10L 10/14 for improving low temperature properties
• CPC Class Codes: C10L 2200/0446 Diesel
• CPC Class Codes: C10L 2200/0469 Renewables or materials of biological origin
• CPC Class Codes: C10L 2270/026 for diesel engines, e.g. automobiles, stationary, marine
• CPC Class Codes: C10L 2270/04 for turbines, planes, power generation
• CPC Class Codes: C10L 2290/543 Distillation, fractionation or rectification for separating fractions, components or impurities during preparation or upgrading of a fuel
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel
• CPC Class Codes: Y02P 30/20 using bio-feedstock
• CPC Class Codes: Y02T 50/678 Aviation using fuels of non-fossil origin

Abstract

The present invention provides a fuel comprising a renewable middle distillate composition obtainable by hydrodeoxygenation of a feedstock comprising levulinic acid dimers/oligomers and fractionated distillation. The renewable middle distillate composition contains less than 10.0 wt.-% aromatics.

Claims

1. A fuel comprising:

a renewable middle distillate composition, wherein the renewable middle distillate composition is obtained from a feedstock having dimers and/or oligomers of levulinic acid and/or of levulinic acid derivatives (levulinic acid dimers/oligomers), subjected to hydrodeoxygenation followed by fractionated distillation, wherein the renewable middle distillate composition contains less than 10.0 wt.-% aromatics, as determined in accordance with ASTM D2425.

2. The fuel according to claim 1, wherein the renewable middle distillate composition contains at most 9.5 wt.% of aromatics, as determined in accordance with ASTM D2425.

3. The fuel according to claim 1, wherein the freezing point of the renewable middle distillate composition is −

70°

C. or lower.

4. The fuel according to claim 1, wherein the renewable middle distillate composition contains at least 50 wt. % of cycloparaffins, as determined in accordance with ASTM D2425.

5. The fuel according to claim 1, wherein the renewable middle distillate composition contains at most 80 wt.% of cycloparaffins, as determined in accordance with ASTM D2425.

6. The fuel according to claim 1, wherein the fuel further contains fossil fuel, HEFA (hydroprocessed ester and fatty acids) fuel and/or HVO (hydrotreated vegetable oil) fuel.

7. The fuel according to claim 1, wherein the BOCLE lubricity of the renewable middle distillate composition is 0.75 mm or less as determined in accordance with ASTM D5001-10 (2014).

14. The fuel according to claim 1, wherein the renewable middle distillate composition obtained by hydrodeoxygenation of dimers and/or oligomers of levulinic acid and/or of levulinic acid derivatives (levulinic acid dimers/oligomers), followed by fractionated distillation, is an aviation fuel or aviation fuel component.

15. The fuel according to claim 1, wherein the renewable middle distillate composition contains at most 3.0 wt.-% of aromatics, as determined in accordance with ASTM D2425.

16. The fuel according to claim 2, wherein the freezing point of the renewable middle distillate composition is −

95°

C. or lower.

17. The fuel according to claim 2, wherein the renewable middle distillate composition contains at least 55 wt.-% of cycloparaffins, as determined in accordance with ASTM D2425.

18. The fuel according to claim 2, wherein the renewable middle distillate composition contains at most 70 wt.-% of cycloparaffins, as determined in accordance with ASTM D2425.

19. The fuel according to claim 2, wherein the BOCLE lubricity of the renewable middle distillate composition is 0.67 mm or less, as determined in accordance with ASTM D5001-10 (2014).

8. A method for production of a renewable middle distillate composition, the method comprising:

subjecting a feedstock containing dimers and/or oligomers of levulinic acid and/or of levulinic acid derivatives (levulinic acid dimers/oligomers) to at least one hydrodeoxygenation (HDO) reaction; and

fractionating the a resulting HDO product to obtain the middle distillate composition,

wherein the renewable middle distillate composition contains less than 10.0 wt.-% aromatics, as determined in accordance with ASTM D2425.

9. The method according to claim 8, wherein the renewable middle distillate composition contains at most 9.5wt.% of aromatics, as determined in accordance with ASTM D2425.

10. The method according to claim 8, comprising:

subjecting a raw material containing at least levulinic acid to a C—

C coupling reaction so as to produce the dimers and/or oligomers of levulinic acid and/or of levulinic acid derivatives (levulinic acid dimers/oligomers).

11. The method according to claim 10, wherein the C—

C-coupling reaction is conducted at a temperature in the range of 100-200°

C.

12. The method according to claim 8, comprising:

providing a raw material containing at least levulinic acid and/or a derivative thereof;

subjecting the raw material to a C—

C coupling reaction, wherein the C—

C coupling reaction is carried out in a presence of hydrogen and using an acidic ion exchange resin carrying a hydrogenating metal as a catalyst, so as to produce a C—

C-coupling containing dimers and/or oligomers of levulinic acid and/or of levulinic acid derivatives (levulinic acid dimers/oligomers);

subjecting a feedstock containing at least the levulinic acid dimers/oligomers to a hydrodeoxygenation (HDO) reaction to produce a HDO product; and

fractionating the HDO product to obtain the middle distillate composition.

20. The method according to claim 8, wherein the renewable middle distillate composition contains at most 3.0 wt.-% of aromatics, as determined in accordance with ASTM D2425.

21. The method according to claim 20, comprising:

subjecting a raw material containing at least levulinic acid to a C—

C coupling reaction so as to produce the dimers and/or oligomers of levulinic acid and/or of levulinic acid derivatives (levulinic acid dimers/oligomers).

22. The method according to claim 10, wherein the C—

C-coupling reaction is conducted at a temperature in the range of 120-140°

C.

13. A method for producing a fuel having a renewable middle distillate composition, wherein the renewable middle distillate composition is obtained from a feedstock having dimers and/or oligomers of levulinic acid and/or of levulinic acid derivatives (levulinic acid dimers/oligomers), subjected to hydrodeoxygenation followed by fractionated distillation, wherein the renewable middle distillate composition contains less than 10.0 wt.-% aromatics, as determined in accordance with ASTM D2425, wherein the middle distillate composition is obtained by a method comprising:

subjecting the feedstock containing dimers and/or oligomers of levulinic acid and/or of levulinic acid derivatives (levulinic acid dimers/oligomers) to at least one hydrodeoxygenation (HDO) reaction; and

fractionating a resulting HDO product to obtain the middle distillate composition,

wherein the renewable middle distillate composition contains less than 10.0 wt.-% aromatics, as determined in accordance with ASTM D2425.