US 11,834,384 B2
Preparation of olefin by alcohol dehydration, and uses thereof for making polymer, fuel or fuel additive
Christine-Joy Richardson, Lyons (FR); Laurent Germanaud, Heyrieux (FR); Stéphane Kressmann, Communay (FR); Steven Henning, Downington, PA (US); Keith Nelson, Exton, PA (US); and Delphine Minoux, Nivelles (BE)
Assigned to TOTAL MARKETING SERVICES, Puteaux (FR)
Appl. No. 16/979,620
Filed by TOTAL MARKETING SERVICES, Puteaux (FR)
PCT Filed Mar. 15, 2019, PCT No. PCT/EP2019/056557
§ 371(c)(1), (2) Date Sep. 10, 2020,
PCT Pub. No. WO2019/175393, PCT Pub. Date Sep. 19, 2019.
Claims priority of application No. 18305299 (EP), filed on Mar. 16, 2018; and application No. 19305169 (EP), filed on Feb. 11, 2019.
Prior Publication US 2021/0040012 A1, Feb. 11, 2021
Int. Cl. C07C 1/24 (2006.01); C07C 11/10 (2006.01); C07C 2/08 (2006.01); C08F 210/08 (2006.01); C10L 1/16 (2006.01)
CPC C07C 1/24 (2013.01) [C07C 2/08 (2013.01); C08F 210/08 (2013.01); C10L 1/1608 (2013.01); C07C 11/10 (2013.01); C07C 2521/04 (2013.01); C07C 2529/65 (2013.01)] 22 Claims
 
1. A C5 olefin mixture containing:
(i) at least 50 wt % of an olefin mixture comprising (i-a) 2-methyl-but-2-ene, (i-b) 2-methyl-but-1-ene and (i-c) 3-methyl-but-1-ene, and
(ii) (ii-a) one C4 olefin chosen among 1-butene, 2-butene, 2-methylpropene, and/or (ii-b) one C6 olefin chosen among 1-hexene, 2-hexene, 3-hexene, 2-methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2-ethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene, cyclohexene, 2-methyl-2-pentene, 3-methyl-2-pentene, 3,3-dimethyl-1-butene, 1-methyl-cyclopentene, 3-methyl-cyclopentene, 4-methyl-cyclopentene, methylene-cyclopentane,
the C5 olefin mixture optionally comprising (ii-c) one C15 hydrocarbon,
the C5 olefin mixture being obtained by a process comprising the steps of:
a) providing an initial composition comprising at least 20 wt % of a C5 branched alcohol based on the total weight of the initial composition, and
b1) dehydrating the initial composition and separating the obtained dehydrated composition to provide a first stream enriched in C2 olefins, a second stream enriched in C5 olefins, and a third stream containing heavier compounds, the C5 olefin mixture being recovered from the second stream enriched in C5 olefins, or
b2) separating the initial composition to provide a first stream enriched in C2 alcohols, a second stream enriched in C5 alcohols, and a third stream enriched in heavier compounds, and dehydrating the second stream enriched in C5 alcohols to obtain the C5 olefin mixture,
wherein the initial composition is obtained by fermentation of biomass feedstocks, and
wherein the initial composition comprises at least 20 wt % Cs branched alcohol, at least 1 wt % ethanol, at least 0.1 wt % n-propanol, at least 1 wt % C4 alcohols, at most 1.5 wt % esters and at least 5 wt % water, based on the total weight of the initial composition.