Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

Processes for producing olefins include integration of steam cracking with a dual catalyst metathesis process. The processes include steam cracking a hydrocarbon feed to form a cracking reaction effluent containing butenes, separating the cracking reaction effluent to produce a cracking C4 effluent including normal butenes, isobutene, and 1,3-butadiene, subjecting the cracking C4 effluent to selective hydrogenation to convert 1,3-butadiene in the cracking C4 effluent to normal butenes, removing isobutene from a hydrogenation effluent to produce a metathesis feed containing normal butenes, and contacting the metathesis feed with a metathesis catalyst and a cracking catalyst directly downstream of the metathesis catalyst to produce a metathesis reaction effluent. Contacting with the metathesis catalyst causes metathesis of normal butenes to produce ethylene, propene, and C5+ olefins, and contacting with the cracking catalyst causes C5+ olefins produced through metathesis to undergo cracking reactions to produce additional propene, ethylene, or both.

Processes for producing olefins include integration of steam cracking with a dual catalyst metathesis process. The processes include steam cracking a hydrocarbon feed to form a cracking reaction effluent containing butenes, separating the cracking reaction effluent to produce a cracking C4 effluent including normal butenes, isobutene, and 1,3-butadiene, subjecting the cracking C4 effluent to selective hydrogenation to convert 1,3-butadiene in the cracking C4 effluent to normal butenes, removing isobutene from a hydrogenation effluent to produce a metathesis feed containing normal butenes, and contacting the metathesis feed with a metathesis catalyst and a cracking catalyst directly downstream of the metathesis catalyst to produce a metathesis reaction effluent. Contacting with the metathesis catalyst causes metathesis of normal butenes to produce ethylene, propene, and C5+ olefins, and contacting with the cracking catalyst causes C5+ olefins produced through metathesis to undergo cracking reactions to produce additional propene, ethylene, or both.

Processes for producing olefins include integration of steam cracking with a dual catalyst metathesis process. The processes include steam cracking a hydrocarbon feed to form a cracking reaction effluent containing butenes, separating the cracking reaction effluent to produce a cracking C4 effluent including normal butenes, isobutene, and 1,3-butadiene, subjecting the cracking C4 effluent to selective hydrogenation to convert 1,3-butadiene in the cracking C4 effluent to normal butenes, removing isobutene from a hydrogenation effluent to produce a metathesis feed containing normal butenes, and contacting the metathesis feed with a metathesis catalyst and a cracking catalyst directly downstream of the metathesis catalyst to produce a metathesis reaction effluent. Contacting with the metathesis catalyst causes metathesis of normal butenes to produce ethylene, propene, and C5+ olefins, and contacting with the cracking catalyst causes C5+ olefins produced through metathesis to undergo cracking reactions to produce additional propene, ethylene, or both.

A process to produce 1-octene and 1-decene includes (a) separating a composition containing an oligomer product—which contains 15 to 80 mol % C.sub.6 olefins, 20 to 80 mol % C.sub.8 olefins, and 5 to 20 mol % C.sub.10+ olefins—into a first oligomer composition containing C.sub.6 alkanes and at least 85 mol % C.sub.6 olefins (e.g., 1-hexene), a second oligomer composition containing at least 20 mol % C.sub.8 olefins (e.g., 1-octene), and a heavies stream containing C.sub.10+ olefins, then (b) contacting a metathesis catalyst system with the first oligomer composition to form a first composition comprising C.sub.10 linear internal olefins, (c) contacting the C.sub.10 linear internal olefins with a catalytic isomerization catalyst system in the presence of photochemical irradiation to form a second composition comprising 1-decene, and (d) purifying the second composition to isolate a third composition comprising at least 90 mol % 1-decene. Processes to produce 1-hexene and 1-decene also are described, as well as related manufacturing systems and processes to produce higher carbon number normal alpha olefins from lower carbon number normal alpha olefins.

A process to produce 1-octene and 1-decene includes (a) separating a composition containing an oligomer product—which contains 15 to 80 mol % C.sub.6 olefins, 20 to 80 mol % C.sub.8 olefins, and 5 to 20 mol % C.sub.10+ olefins—into a first oligomer composition containing C.sub.6 alkanes and at least 85 mol % C.sub.6 olefins (e.g., 1-hexene), a second oligomer composition containing at least 20 mol % C.sub.8 olefins (e.g., 1-octene), and a heavies stream containing C.sub.10+ olefins, then (b) contacting a metathesis catalyst system with the first oligomer composition to form a first composition comprising C.sub.10 linear internal olefins, (c) contacting the C.sub.10 linear internal olefins with a catalytic isomerization catalyst system in the presence of photochemical irradiation to form a second composition comprising 1-decene, and (d) purifying the second composition to isolate a third composition comprising at least 90 mol % 1-decene. Processes to produce 1-hexene and 1-decene also are described, as well as related manufacturing systems and processes to produce higher carbon number normal alpha olefins from lower carbon number normal alpha olefins.

A process to produce 1-octene and 1-decene includes (a) separating a composition containing an oligomer product—which contains 15 to 80 mol % C.sub.6 olefins, 20 to 80 mol % C.sub.8 olefins, and 5 to 20 mol % C.sub.10+ olefins—into a first oligomer composition containing C.sub.6 alkanes and at least 85 mol % C.sub.6 olefins (e.g., 1-hexene), a second oligomer composition containing at least 20 mol % C.sub.8 olefins (e.g., 1-octene), and a heavies stream containing C.sub.10+ olefins, then (b) contacting a metathesis catalyst system with the first oligomer composition to form a first composition comprising C.sub.10 linear internal olefins, (c) contacting the C.sub.10 linear internal olefins with a catalytic isomerization catalyst system in the presence of photochemical irradiation to form a second composition comprising 1-decene, and (d) purifying the second composition to isolate a third composition comprising at least 90 mol % 1-decene. Processes to produce 1-hexene and 1-decene also are described, as well as related manufacturing systems and processes to produce higher carbon number normal alpha olefins from lower carbon number normal alpha olefins.

A method of producing a fuel additive includes passing a feed stream comprising C4 hydrocarbons through a methyl tertiary butyl ether unit producing a first process stream; passing the first process stream through a selective hydrogenation unit producing a second process stream; passing the second process stream through an isomerization unit producing a third process stream; and passing the third process stream through a hydration unit producing the fuel additive and a recycle stream.

A method of producing a fuel additive includes passing a feed stream comprising C4 hydrocarbons through a methyl tertiary butyl ether unit producing a first process stream; passing the first process stream through a selective hydrogenation unit producing a second process stream; passing the second process stream through an isomerization unit producing a third process stream; and passing the third process stream through a hydration unit producing the fuel additive and a recycle stream.