Renewable chemical production engaging metathesis and microbial oxidation

Patent metadata

Field	Value
Publication number	US-2023339828-A2
Application number	US-202017762974-A
Country	US
Kind code	A2
Filing date	Sep 25, 2020
Priority date	Sep 26, 2019
Publication date	Oct 26, 2023
Grant date	—

Abstract

Herein is provided a process for combined renewable 1-decene and renewable carboxylic diacid production from a fatty acid ester containing feedstock, wherein the feedstock is first subjected to metathesis reaction conditions, recovery of 1-decene and then to microbial oxidation to yield diacids in a fermentation broth. Diacids of unusual carbon chains lengths are thereby obtainable.

First claim

1 . A process for producing 1-decene and renewable carboxylic diacids from a C6-C22 fatty acid ester containing feedstock, the process comprising:
a) providing the C6-C22 fatty acid ester containing feedstock, wherein the feedstock contains at least one unsaturated fatty acid ester; b) subjecting the feedstock to metathesis reaction conditions in the presence of an alkene selected from C2, C3, C4 alkenes and a metathesis catalyst, to obtain metathesis products comprising renewable alkenes and fatty acid esters; c) recovering C10 alkenes, comprising 1-decene from the metathesis products; d) subjecting a part of the metathesis products after optional pretreatment(s), to microbial oxidation to yield diacids in a fermentation broth; e) recovery of the renewable diacids from the fermentation broth.

2 . A process according to claim 1 , wherein a pretreatment in step d) comprises hydrolysis of any metathesis products in form of esters before subjecting said metathesis products to microbial oxidation in step d).

3 . A process according to claim 1 or 2 , wherein the pretreatment in step d) comprises hydrogenation of the metathesis products in the form of alkenes and unsaturated fatty acids before subjecting said metathesis products to microbial oxidation in step d).

4 . A process according to one of claim 1 or 2 , wherein renewable diacids recovered from the fermentation broth are subjected to hydrogenation to saturate any C═C double bonds.

5 . A process according to any one of the previous claims, wherein the fatty acid ester containing feedstock from step a) is subjected to a pretreatment selected from a treatment with an adsorbent, a treatment with a metal alkyl compound, a treatment with a metal alkoxide compound, a treatment with a reducing agent, a treatment with an organic or inorganic drying agent, a thermal treatment or a combination thereof.

6 . A process according to claim 1 , wherein separation step c), following the metathesis step b), comprises recovering metathesis catalyst before subjecting the remaining metathesis products to microbial oxidation in step d).

7 . A process according to one of the claims 1 - 6 , wherein separation in step c) comprises a flash evaporation for removing a gaseous fraction, preferably comprising C 2 to C 4 alkenes, from the metathesis products, and optionally recycling them back to metathesis reaction.

8 . A process according to one of the claims 1 - 7 , wherein the C2-C4 alkene in metathesis reaction is ethene or 2 -butene, more preferably ethene.

9 . A process according to one of the claims 1 - 7 , wherein the C4 alkene in metathesis reaction is propene or 1-butene.

10 . A process according to any of the preceding claims, wherein metathesis conditions comprise a temperature from 20 to 120° C., a pressure from 0.1 to 3 MPa and a metathesis catalyst comprising a metal selected from ruthenium, molybdenum, osmium, chromium, rhenium, tungsten, preferably selected from tungsten, ruthenium, molybdenum.

11 . A process according to claim 2 , wherein separation in step d) further comprises fractional distillation and recovery of at least one fraction selected from
a first fraction comprising at least 80%-wt of the total fraction weight unsaturated fatty acids having a carbon chain length of C10. a second fraction comprising at least 80%-wt of the total fraction weight saturated fatty acids having a carbon chain length from C11 to C15; a third fatty acid fraction comprising at least 80%-wt of the total fraction weight fatty acids having a carbon chain length C16; a fourth fatty acid fraction comprising at least 80%-wt of the total fraction weight fatty acids having a carbon chain length from C17 to C18; a fraction comprising renewable alkenes having carbon numbers from C11 to C12.

12 . Process according to claim 11 , further comprising subjecting the third fatty acid fraction comprising fatty acids having a carbon chain length C16, to ketonisation and hydrotreatment to produce renewable base oil fulfilling the API group III requirements.

13 . A process according to claim 11 or 12 , further comprising subjecting the third fatty acid fraction comprising fatty acids having a carbon chain length C16, to ketonisation whereby ethene is released, recovered and recycled back to metathesis reaction in step b).

14 . A process according to claim 11 , wherein the fourth fatty acid fraction is subjected to hydrotreatment, preferably by combined or sequential hydrodeoxygenation and hydroisomerization, whereby at least one component is obtained selected from renewable diesel, renewable naphtha, renewable aviation fuel, and renewable gasoline.

15 . Use of combined metathesis reaction of fatty acid esters and microbial oxidation for producing renewable 1-decene and carboxylic diacids, by a process according to one of claims 1 - 14 .

16 . Use according to claim 15 further comprising renewable base oil production by process according to claim 12 or 13 .

17 . Use according to claim 15 or 16 further comprising renewable fuel production.

Assignees

• Neste Oyj

Inventors

• Hietala Jukka
• Räsänen Jukka
• Leminen Anja
• Rämö Virpi

Classifications

• C07C6/04 Primary

  at a carbon-to-carbon double bond · CPC title

• C07C67/333

  by isomerisation; by change of size of the carbon skeleton (introduction or elimination of carboxyl groups C07C67/313, C07C67/32) · CPC title

• C12P7/6409

  Fatty acids · CPC title

• C07C51/36

  by hydrogenation of carbon-to-carbon unsaturated bonds · CPC title

• C07C51/44

  by distillation · CPC title