US 11,884,614 B2
Normal alpha olefin synthesis using decarbonylative olefination
Brooke L. Small, Kingwood, TX (US); and Michael S. Webster-Gardiner, Humble, TX (US)
Assigned to Chevron Phillips Chemical Company LP, The Woodlands, TX (US)
Filed by Chevron Phillips Chemical Company LP, The Woodlands, TX (US)
Filed on May 26, 2022, as Appl. No. 17/824,960.
Prior Publication US 2023/0382825 A1, Nov. 30, 2023
Int. Cl. C07C 5/03 (2006.01); C07C 45/50 (2006.01); C07C 1/207 (2006.01); B01J 31/28 (2006.01); B01J 23/44 (2006.01); C07C 1/24 (2006.01)
CPC C07C 5/03 (2013.01) [B01J 23/44 (2013.01); B01J 31/28 (2013.01); C07C 1/2076 (2013.01); C07C 1/24 (2013.01); C07C 45/505 (2013.01); C07C 2523/44 (2013.01)] 21 Claims
 
1. A process comprising:
(i) subjecting a first normal alpha olefin having the structure (C)n—C═C to hydroformylation in the presence of carbon monoxide and hydrogen to form a first composition comprising a first linear aldehyde having the structure C(C)n+1CH(═O);
(ii) subjecting the first linear aldehyde to decarbonylative olefination to form a second composition comprising a C2n+5 linear internal olefin;
(iii) subjecting the linear internal olefin to isomerization-hydroformylation in the presence of carbon monoxide and hydrogen to form a third composition comprising a second linear aldehyde having the structure C(C)2n+4CH(═O); and
(iv-a) subjecting the second linear aldehyde to hydrogenation-dehydration to form a product composition comprising a second normal alpha olefin having the structure (C)2n+4—C═C; or
(iv-b1) subjecting the second linear aldehyde to hydrogenation to form a fourth composition comprising a linear alcohol having the structure C(C)2n+4C(OH); and
(iv-b2) subjecting the linear alcohol to dehydration to form a product composition comprising a second normal alpha olefin having the structure (C)2n+4—C═C;
wherein n is an integer from 0 to 30.