# US 10,370,317 B2 · Method for ketonisation of biological material

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- Number: US 10,370,317 B2
- Document ID: US10370317B2
- Status: Granted
- Kind: B2
- Application number: 16/027,714
- Filed: 2018-07-05
- Published: 2019-01-03
- Granted: 2019-08-06
- Earliest claimed: 2014-10-24
- Assignees: Neste Oyj
- Applicants: Neste Oyj
- Inventors: Mika Kettunen; Jukka Myllyoja; Rami Piilola
- Web page: https://patentgrep.com/patent/US10370317B2

## CPC

- C07C 45/48: involving decarboxylation
- B01J 21/063: {Titanium; Oxides or hydroxides thereof}
- B01J 23/04: Alkali metals
- B01J 23/883: and nickel
- B01J 35/19: {Catalysts containing parts with different compositions}
- C10G 3/42: {Catalytic treatment}
- C10G 3/46: {in combination with chromium, molybdenum, tungsten metals or compounds thereof}
- C10G 3/47: {containing platinum group metals or compounds thereof}
- C10G 3/50: {in the presence of hydrogen, hydrogen donors or hydrogen generating compounds}
- C10G 45/58: to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins (C10G32/00 takes precedence; improving or increasing the octane number or aromatic content of naphtha C10G35/00)
- C10G 65/043: {at least one step being a change in the structural skeleton}
- B01J 23/42: Platinum
- B01J 29/85: Silicoaluminophosphates [SAPO compounds]
- C10G 2300/1011: Biomass
- C10G 2400/10: Lubricating oil
- Y02P 30/20: using bio-feedstock
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A method for producing ketones includes a) providing a feedstock of biological origin having fatty acids and/or fatty acid derivatives having an average chain length of 24 C-atoms or less; b) subjecting the feedstock to a catalytic ketonization reaction in the presence of aK2O/TiO2-catalyst; and c) obtaining from the ketonization reaction a product stream having ketones, which ketones have a longer average hydrocarbon chain length than the average hydrocarbon chain length in the feedstock, wherein step b) is carried out directly on the feedstock and in the presence of the K2O/TiO2-catalyst as the sole catalyst applied in the ketonization reaction.

## Claims

### Claim 1

A method for producing ketones, which method comprises:
a) providing a feedstock of biological origin containing fatty acids and/or fatty acid derivatives having an average chain length of 24 C-atoms or less;
b) subjecting said feedstock to a catalytic ketonisation reaction performed under a gas pressure of from 0.5 MPa to 5 MPa in a presence of a K2O/TiO2-catalyst; and
c) obtaining from said ketonisation reaction a product stream containing ketones, which ketones have a longer average hydrocarbon chain length than the average hydrocarbon chain length in said feedstock;
wherein the feedstock is in liquid form during the subjecting;
wherein the feedstock has a liquid feed flow rate WHSV of from 0.1 h−1 to 10 h−1; and
wherein the subjecting is carried out directly on said feedstock and in a presence of said K2O/TiO2-catalyst as a sole catalyst applied in said ketonisation reaction.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the subjecting is carried out directly on said feedstock without preceding or simultaneous hydrogenation of double bonds present in the fatty acids and/or fatty acid derivatives in said feedstock.

### Claim 3 (depends on 1)

The method according to claim 1, wherein said feedstock of biological origin contains unsaturated fatty acids and/or fatty acid derivatives, or esters.

### Claim 4 (depends on 1)

The method according to claim 1, comprising:
achieving said gas pressure by hydrogen or nitrogen or any other suitable gas.

### Claim 5 (depends on 1)

The method according to claim 1, wherein said K2O/TiO2-catalyst is supported on alumina, silica or active carbon.

### Claim 6 (depends on 1)

The method according to claim 1, comprising:
performing said ketonisation reaction in a temperature ranging from 150° C. to 400° C.

### Claim 7 (depends on 1)

The method according to claim 1, comprising:
d) a hydrodeoxygenation step wherein said ketones obtained from said ketonisation reaction are hydrodeoxygenated;
e) an optional isomerisation step; and
f) optional step(s) of further after-treatment.

### Claim 8 (depends on 7)

The method according to claim 7, comprising:
carrying out said hydrodeoxygenation step in a presence of a Pd, Pt, Ni, NiMo, NiW or CoMo catalyst optionally being supported, on alumina, silica or active carbon.

### Claim 9 (depends on 7)

The method according to claim 7, comprising:
carrying out said optional isomerisation step in the presence of a Pd, Pt or Ni metal catalyst, or a Pt-SAPO or Pt-ZSM catalyst.

### Claim 10 (depends on 7)

The method according to claim 7, comprising:
carrying out said hydrodeoxygenation step and said optional isomerisation step in the same reaction zone as said ketonisation reaction or in separate reaction zone(s) subsequent to said ketonisation reaction zone.

### Claim 11 (depends on 1)

The method of claim 1, comprising:
including said ketones as base oil components or as intermediate material for product of base oil components.

### Claim 12 (depends on 11)

The method according to claim 11, comprising:
obtaining the ketones from a feedstock containing triglycerides.

### Claim 13 (depends on 1)

The method according to claim 1, comprising:
performing said ketonisation reaction under gas pressure of from 1 MPa to 3 MPa.

### Claim 14 (depends on 1)

The method according to claim 1, comprising:
performing said ketonisation reaction under gas pressure of from 1.5 MPa to 2 MPa.

### Claim 15 (depends on 1)

The method according to claim 1, comprising:
performing said ketonisation reaction in a temperature ranging from 200° C. to 375° C., and/or a liquid feed flow rate WHSV from 0.2 to 5 h−1.

### Claim 16 (depends on 1)

The method according to claim 1, comprising:
performing said ketonisation reaction in a temperature ranging from 250° C. to 350° C., and/or a liquid feed flow rate WHSV from 0.5 to 1 h−1.

### Claim 17 (depends on 1)

The method according to claim 1, comprising:
performing said ketonisation reaction in a temperature ranging from 275° C. to 325° C., and/or a liquid feed flow rate WHSV from 0.5 to 1 h−1.

### Claim 18 (depends on 1)

The method according to claim 1, wherein the feedstock comprises triglycerides or a mixture of triglycerides and free fatty acids, and wherein the catalytic ketonisation reaction is performed without preceding hydrogenation of double bonds present in the fatty acids and/or fatty acid derivatives.