IP Library Granted Patent US 12,637,622
Granted Patent B2
US 12,637,622 · App. 17/261,754 · Granted May 26, 2026

Production of hydrocarbons from recycled or renewable organic material

Inventors: Jouni Touronen (Porvoo, FI); Kaisa Lamminpää (Porvoo, FI); Antti Pasanen (Porvoo, FI); Susanna Kuitunen (Porvoo, FI); Anna Zaitseva (Porvoo, FI)
Assignee: NESTE OYJ
C10G3/50C10G1/002C10G3/42C10G9/36C10G11/00C10G45/58C10G47/00C10G2300/1003
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Quick Facts
Patent No.
US 12,637,622
App. No.
17/261,754
Granted
May 26, 2026
Kind
B2
Abstract

A method is disclosed of producing hydrocarbons from a recycled or renewable organic material wherein the recycled or renewable organic material contains hydroxyaromatic hydrocarbon compounds. Exemplary methods include (a) providing recycled or renewable organic material; (b) optionally purifying the recycled or renewable organic material; (c) hydrotreating the recycled or renewable organic material in a presence of a hydrotreating catalyst, thereby forming a hydrocarbon stream and a phenol-containing effluent; (d) separating phenols from the phenol-containing effluent of step (c), thereby forming a phenol stream and a purified water stream; and (e) recycling the phenol stream obtained in step (d) to step (c) to increase the yield of hydrocarbons obtained from step (c); to obtain hydrocarbons containing less than 1 wt % oxygen.

Claims (35)

1 . A method of producing hydrocarbons from a recycled or renewable organic material wherein the recycled or renewable organic material contains hydroxyaromatic hydrocarbon compounds, the method comprising:

(a) providing recycled or renewable organic material;

(b) optionally purifying the recycled or renewable organic material;

(c) hydrotreating the recycled or renewable organic material in a presence of a hydrotreating catalyst, thereby forming a hydrocarbon stream and a phenol-containing effluent;

(d) separating phenols from the phenol-containing effluent of step (c), by liquid-liquid extraction with a non-aromatic organic solvent that is sparingly soluble to water or by stripping, thereby forming a phenol stream and a purified water stream; and

(e) recycling the phenol stream obtained in step (d) to step (c) to increase a yield of hydrocarbons obtained from step (c);

to obtain hydrocarbons containing less than 1 wt % oxygen,

wherein the recycled or renewable organic material includes at least one or more of crude tall oil (CTO) and its derivatives; tall oil pitch (TOP), tall oil fatty acid (TOFA), distilled tall oil (DTO) and crude fatty acid (CFA); sterol containing fats, and/or animal fats.

2 . A method as claimed in claim 1 , wherein the recycled or renewable organic material is selected to contain more than 0.01 wt % hydroxyaromatic hydrocarbon compounds.

3 . A method as claimed in claim 1 , wherein the hydroxyaromatic hydrocarbon compounds are selected from among plant based hydroxyaromatic hydrocarbon compounds, sterols and/or lignin and/or animal fat based compounds, and sterols.

4 . A method as claimed in claim 1 , wherein step (b) is accomplished by heat treating the recycled or renewable organic material.

5 . A method as claimed in claim 1 , wherein step (b) is accomplished by bleaching the recycled or renewable organic material.

6 . A method as claimed in claim 5 , wherein hydrotreating step (c) takes place under continuous hydrogen flow.

7 . A method as claimed in claim 6 , wherein in step (c) the continuous hydrogen flow has an H2/feed ratio selected to be from 500 to 2000 n-L/L.

8 . A method as claimed in claim 1 , wherein step (c) is performed at a temperature selected to be from 270 to 380° C.

9 . A method as claimed in claim 1 , wherein step (c) is performed under pressure from 4 to 20 MPa.

10 . A method as claimed in claim 1 , wherein the hydrotreating catalyst in step (c) includes at least one component selected from IUPAC group 6, 8 or 10 of the Periodic Table.

11 . A method as claimed in claim 1 , wherein the hydrotreating catalyst in step (c) is a supported Pd, Pt, Ni, NiW, NiMo or a CoMo catalysts and the support is zeolite, zeolite-alumina, alumina and/or silica, NiW/Al 2 O 3 , NiMo/Al 2 O 3 or CoMo/Al 2 O 3 .

12 . A method as claimed in claim 1 , wherein step (c) is accomplished by (c1) hydrodeoxygenating (HDO) the recycled or renewable organic material.

13 . A method as claimed in claim 12 , wherein in step (c1) the HDO catalyst is sulphided NiW, NiMO or COMO catalyst.

14 . A method as claimed in claim 12 , wherein HDO is performed at a temperature from 290 to 350° C. under pressure from 4 to 20 MPa and under continuous hydrogen flow.

15 . A method as claimed in claim 1 , wherein a part of the hydrotreated product is recycled in step (c).

16 . A method as claimed in claim 15 , wherein a ratio of fresh feed to the hydrotreated product is from 2:1 to 20:1.

17 . A method as claimed in claim 1 , wherein the non-aromatic organic solvent is selected from a group consisting of mesityl oxide, methyl isobutyl ketone, methyl tert-butyl ketone, methyl tert-butyl ether, methyl isopropyl ketone, 3-heptanone, 2-hexanone and mixtures thereof.

18 . A process for producing recycled or renewable hydrocarbons, the process comprising:

(x) producing hydrocarbons from a recycled or renewable organic material as claimed in claim 1 ; and

(y) subjecting the hydrocarbons to an oil refinery conversion process, wherein the oil refinery conversion process includes altering a molecular weight of the feed, removal of heteroatoms from the feed, altering a degree of saturation of the feed, rearranging the molecular structure of the feed, or any combination thereof to obtain at least one recycled or renewable hydrocarbon.

19 . A process as claimed in claim 18 , wherein step (y) is hydrocracking.

20 . A process as claimed in claim 19 , wherein step (y) is performed in a mild hydrocracking (MHC) refinery unit.

21 . A process as claimed in claim 19 , wherein step (y) is performed in a presence of a hydrocracking catalyst.

22 . A process as claimed in claim 18 , wherein step (y) is steamcracking.

23 . A process as claimed in claim 18 , wherein step (y) is isomerization.

24 . A process as claimed in claim 18 , wherein step (y) is hydrotreating.

25 . A process as claimed in claim 18 , wherein step (y) is thermal catalytic cracking.

26 . A process as claimed in claim 18 , wherein step (y) is fluid catalytic cracking.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2021
From: TOURONEN, JOUNI; LAMMINPÄÄ, KAISA; PASANEN, ANTTI; KUITUNEN, SUSANNA; ZAITSEVA, ANNA
To: NESTE OYJ
Reel/Frame 055804/0334 →
Priority Claims (1)
FI 20185653 · Jul 20, 2018 · national
Continuity (1)
Related Publication 20210269722A1 · Sep 2, 2021
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