US 12,145,906 B2
Renewable chemical production engaging metathesis and microbial oxidation
Jukka Hietala, Porvoo (FI); Jukka Räsänen, Porvoo (FI); Anja Leminen, Porvoo (FI); and Virpi Rämö, Porvoo (FI)
Assigned to NESTE OYJ, Espoo (FI)
Appl. No. 17/762,974
Filed by Neste Oyj, Espoo (FI)
PCT Filed Sep. 25, 2020, PCT No. PCT/FI2020/050632
§ 371(c)(1), (2) Date Mar. 23, 2022,
PCT Pub. No. WO2021/058877, PCT Pub. Date Apr. 1, 2021.
Claims priority of application No. 20195822 (FI), filed on Sep. 26, 2019.
Prior Publication US 2022/0356131 A1, Nov. 10, 2022
Prior Publication US 2023/0339828 A2, Oct. 26, 2023
Int. Cl. C07C 6/04 (2006.01); C07C 1/22 (2006.01); C07C 5/22 (2006.01); C07C 51/36 (2006.01); C07C 51/44 (2006.01); C07C 67/333 (2006.01); C10G 3/00 (2006.01); C10M 101/04 (2006.01); C10M 177/00 (2006.01); C10N 70/00 (2006.01); C12P 7/6409 (2022.01)
CPC C07C 6/04 (2013.01) [C07C 1/22 (2013.01); C07C 5/22 (2013.01); C07C 51/36 (2013.01); C07C 51/44 (2013.01); C07C 67/333 (2013.01); C10G 3/42 (2013.01); C10M 101/04 (2013.01); C10M 177/00 (2013.01); C12P 7/6409 (2013.01); C10G 2300/1011 (2013.01); C10M 2203/1025 (2013.01); C10N 2070/00 (2013.01)] 23 Claims
 
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 a presence of (1) an alkene selected from the group consisting of a C2 alkene, a C3 alkene, a C4 alkene and a combination thereof, and (2) a metathesis catalyst, to obtain metathesis products containing renewable alkenes and fatty acid esters;
c) recovering C10 alkenes, containing 1-decene from the metathesis products;
d) subjecting a part of the metathesis products including the fatty acid esters to a pretreatment, wherein the pretreatment includes producing fatty acids from the fatty acid esters, and subjecting the fatty acids to microbial oxidation in a presence of genetically engineered microorganisms cultured in a liquid medium containing a carbon source and other nutrients, to yield a plurality of renewable diacids each having a carbon number from C10 to C15 in a fermentation broth; and
e) recovering the plurality of renewable diacids from the fermentation broth.