Upgrading lignocellulosic or carbohydrate material

Patent metadata

Field	Value
Publication number	US-10988431-B2
Application number	US-201716474786-A
Country	US
Kind code	B2
Filing date	Dec 22, 2017
Priority date	Dec 30, 2016
Publication date	Apr 27, 2021
Grant date	Apr 27, 2021

Abstract

The present disclosure relates to a method for upgrading lignocellulosic material carbohydrates and/or carbohydrate derivatives by dimerisation and/or oligomerisation using specific catalysts and to the use of the upgraded products.

First claim

The invention claimed is:

1. A method for upgrading carbohydrates, carbohydrate derivatives or lignocellulosic material, the method comprising:
providing a feedstock containing carbohydrates, carbohydrate derivatives or lignocellulosic material, wherein the carbohydrates, carbohydrate derivatives, or lignocellulosic material include(s) angelica lactone; and
dimerising and oligomerising the carbohydrates, carbohydrate derivatives, or lignocellulosic material at a reaction temperature in a range of 30° C. to 195° C., in a presence of a heterogeneous catalyst to produce a dimer and oligomer product;
wherein the oligomerising constitutes formation of trimers or higher and wherein the content of trimers or higher is 30 area-% or more in a Gel Permeation Chromatography (GPC) chromatogram relative to the sum of dimers and oligomers in the dimer and oligomer product,
wherein the lignocellulosic material is levulinic acid, an ester of levulinic acid and/or a dehydration product of levulinic acid,
wherein the heterogeneous catalyst is an inorganic catalyst containing an alkali metal compound and at least one further metal compound, or is an inorganic catalyst containing an alkali metal compound and an alkaline earth metal compound and at least one further metal compound, and
wherein the further metal constituting the at least one further metal compound is at least one selected from the group consisting of Al, Si, Sc, Ti, V, Y, Zr, Nb, Mo, La, Ce, Hf, Ta and W.

2. The method according to claim 1 , wherein the heterogeneous catalyst is a supported catalyst.

3. The method according to claim 2 , wherein the heterogeneous catalyst is a catalyst comprising:
the alkali metal compound and/or the alkaline earth metal compound on a support formed by the at least one further metal compound.

4. The method according to claim 3 , wherein the support is formed by an oxide of the further metal.

5. The method according to claim 2 , wherein the heterogeneous catalyst is a catalyst comprising:
an oxide of the alkali metal and/or an oxide of the alkaline earth metal on a support formed by an oxide of the further metal.

6. The method according to claim 1 , wherein the heterogeneous catalyst is a catalyst comprising:
the alkali metal compound and/or the alkaline earth metal compound as a mixed compound.

7. The method according to claim 6 , wherein all metal compounds of the catalyst are in oxide form.

8. The method according to claim 1 , wherein a metal constituting the alkali metal compound and/or an alkaline earth metal compound is at least one selected from the group consisting of Li, Na, K, Mg and Ca.

9. The method according to claim 5 , wherein the metal constituting the alkali metal compound and/or an alkaline earth metal compound is at least one selected from the group consisting of Li, Na, K, Mg and Ca.

10. The method according to claim 8 , wherein the further metal constituting the at least one further metal compound is at least one selected from the group consisting of Al, Si, Sc, Ti, V, Y, Zr, Nb, Mo, La, Ce, Hf, Ta and W.

11. The method according to claim 9 , wherein the further metal constituting the at least one further metal compound is at least one selected from the group consisting of Al, Si, Sc, Ti, V, Y, Zr, Nb, Mo, La, Ce, Hf, Ta and W.

12. The method according to claim 1 , wherein the further metal constituting the at least one further metal compound is at least one selected from the group consisting of Al, Si, Ti, Zr and Ce.

13. The method according to claim 8 , wherein the further metal constituting the at least one further metal compound is at least one selected from the group consisting of Al, Si, Ti, Zr and Ce.

14. The method according to claim 9 , wherein the further metal constituting the at least one further metal compound is at least one selected from the group consisting of Al, Si, Ti, Zr and Ce.

15. The method according to claim 1 , wherein the heterogeneous catalyst further comprises a compound selected from the group consisting of NaOx/AlOx; KOx/AlOx; MgOx/AlOx; NaOx/SiOx; KOx/SiOx; MgOx/SiOx; NaOx/TiOx; KOx/TiOx; MgOx/TiOx; NaOx/CeOx; KOx/CeOx; MgOx/CeOx; NaOx/ZrOx; KOx/ZrOx; and MgOx/ZrOx,
wherein the term “Ox” refers to an oxide of a respective metal and a sign “I” refers to providing respective compounds as a supported catalyst, including being the support, or a mixed compound catalyst.

16. The method according to claim 15 , wherein the heterogeneous catalyst further comprises a compound selected from the group consisting of KOx/TiOx and MgOx/ZrOx.

17. The method according to claim 1 , wherein the heterogeneous catalyst further comprises:
potassium oxide/titania (K 2 O/TiO 2 ) or magnesia/zirconia (MgO/ZrO 2 ).

18. The method according to claim 1 , wherein the reaction temperature is in a range of 30° C. to 190° C.

19. The method according to claim 1 , wherein the reaction temperature is in a range of 30° C. to 185° C.

20. The method according to claim 15 , wherein the reaction temperature is in a range of 30° C. to 180° C.

21. The method according to claim 16 , wherein the reaction temperature is in a range of 30° C. to 150° C.

22. The method according to claim 17 , wherein the reaction temperature is in a range of 30° C. to 140° C.

23. The method according to claim 18 , wherein the reaction temperature is in a range of 30° C. to 130° C.

24. The method according to claim 1 , wherein the reaction temperature is in a range of 50° C. to 185° C.

25. The method according to claim 1 , wherein the heterogeneous catalyst is an inorganic catalyst comprising:
an alkali metal compound and an alkaline earth metal compound and one further metal compound as the heterogeneous catalyst.

26. The method according to claim 1 , wherein the alkaline metal compound and/or the alkaline earth metal compound is a metal oxide, a metal nitride, a metal carbonate and/or a metal carbide.

27. The method according to claim 1 , wherein the metal constituting the alkali metal compound and/or an alkaline earth metal compound is at least one selected from the group consisting of Na, K and Mg.

28. The method according to claim 1 , comprising:
hydrogenating the dimer and oligomer product to obtain a hydrogenated product.

29. The method according to claim 1 , comprising:
applying the dimer and oligomer product as an intermediate for producing fuel and/or chemicals.

30. The method according to claim 28 , comprising:
providing the hydrogenated product as a fuel component.

Assignees

• Neste Oyj

Inventors

• Linblad Marina
• Käldström Mats
• Wallenius Susanna
• Sundblom Sören
• Seläntaus Maaria
• Ikonen Elias

Classifications

• Y02P30/20

  using bio-feedstock · CPC title

• C10G3/50 Primary

  in the presence of hydrogen, hydrogen donors or hydrogen generating compounds · CPC title

• C07C51/353 Primary

  by isomerisation; by change of size of the carbon skeleton · CPC title

• B01J23/10

  of rare earths · CPC title

• C07C51/367

  by introduction of functional groups containing oxygen only in singly bound form · CPC title