A process to produce 1-octene and 1-decene includes (a) separating a composition containing an oligomer product—which contains from 15 to 80 mol % C.sub.6 olefins, from 20 to 80 mol % C.sub.8 olefins, and from 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 85 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 an isomerization hydrofunctionalization catalyst system to form a second composition containing a functionalized alkane, (d) retro-hydrofunctionalizing the functionalized alkane to form a third composition containing 1-decene, and (e) purifying the third composition to isolate a fourth composition containing at least 90 mol % 1-decene. Processes to produce 1-hexene and 1-decene also are described, as well as related manufacturing systems.

The invention relates to methods of hydrodeoxygenation of oxygenated compounds into compounds with unsaturated carbon-carbon bonds, comprising the steps of: a) providing a reaction mixture comprising, an oxygenated compound containing one or more of a hydroxyl, keto or aldehyde group, an ionic liquid, a homogeneous metal catalyst, and carbon monoxide or a carbon monoxide releasing compound, b) reacting said reaction mixture under a H2 atmosphere at acidic conditions at a temperature between 180 and 250° C. and a pressure between 10 and 200 bar.

The invention relates to methods of hydrodeoxygenation of oxygenated compounds into compounds with unsaturated carbon-carbon bonds, comprising the steps of: a) providing a reaction mixture comprising, an oxygenated compound containing one or more of a hydroxyl, keto or aldehyde group, an ionic liquid, a homogeneous metal catalyst, and carbon monoxide or a carbon monoxide releasing compound, b) reacting said reaction mixture under a H2 atmosphere at acidic conditions at a temperature between 180 and 250° C. and a pressure between 10 and 200 bar.

The present disclosure relates to a process for converting one or more alkyl halides to acyclic C3-C6 olefins, said process comprising the steps of (a) providing a feedstream comprising one or more alkyl halides; (b) providing a catalyst composition; and (c) contacting said feedstream with said catalyst composition under reaction conditions. The process is remarkable in that said process further comprises a step of steaming said catalyst composition before the step (c) and in that said catalyst composition comprises one or more zeolites and a binder, wherein said one or more zeolites comprise at least one 10-membered ring channel. The present disclosure further relates to the use of a catalyst composition in said process, said catalyst composition comprising one or more zeolites and a binder, wherein said catalyst composition is steamed before use.

The present disclosure relates to a process for converting one or more alkyl halides to acyclic C3-C6 olefins, said process comprising the steps of (a) providing a feedstream comprising one or more alkyl halides; (b) providing a catalyst composition; and (c) contacting said feedstream with said catalyst composition under reaction conditions. The process is remarkable in that said process further comprises a step of steaming said catalyst composition before the step (c) and in that said catalyst composition comprises one or more zeolites and a binder, wherein said one or more zeolites comprise at least one 10-membered ring channel. The present disclosure further relates to the use of a catalyst composition in said process, said catalyst composition comprising one or more zeolites and a binder, wherein said catalyst composition is steamed before use.

The present disclosure relates to a process for converting one or more methyl halides to acyclic C3-C6 olefins, said process comprising the steps of (a) providing a feedstream comprising one or more methyl halides; (b) providing a catalyst composition; and (c) contacting said feedstream with said catalyst composition under reaction conditions. The process is remarkable in that said reaction conditions include a reaction temperature below 400° C., and in that said catalyst composition comprises one or more molecular sieves with a Si/Al atomic ratio ranging from 2 to 18 and wherein said one or more molecular sieves comprise a plurality of pores, wherein said pores have a shape of an 8-membered ring or less.

The present disclosure relates to a process for converting one or more methyl halides to acyclic C3-C6 olefins, said process comprising the steps of (a) providing a feedstream comprising one or more methyl halides; (b) providing a catalyst composition; and (c) contacting said feedstream with said catalyst composition under reaction conditions. The process is remarkable in that said reaction conditions include a reaction temperature below 400° C., and in that said catalyst composition comprises one or more molecular sieves with a Si/Al atomic ratio ranging from 2 to 18 and wherein said one or more molecular sieves comprise a plurality of pores, wherein said pores have a shape of an 8-membered ring or less.

The invention relates to a process for the oligomerization of ethylene, carried out at a pressure of between 0.1 and 10.0 MPa, at a temperature of between 30 and 200° C., in a cascade of N gas/liquid reactors in series, N being at least equal to 2, comprising a step of introducing a catalytic oligomerization system into at least the first reactor of the cascade, a step of bringing said catalytic system and an optional solvent into contact with ethylene by introducing said ethylene into the lower part of the reaction chamber of at least the first reactor of the cascade, for each reactor n, a step of withdrawing a liquid fraction in the lower part of the reaction chamber of the reactor n, the liquid fraction being separated into two streams: a first stream corresponding to a first, “main”, part of the liquid fraction, which is conveyed to a heat exchanger for cooling; a second stream corresponding to the second part of the liquid fraction which constitutes the liquid feedstock of the following reactor n+1 in the cascade, a step of introducing said second part of the liquid phase withdrawn from the reactor n towards the reaction chamber of the following reactor n+1 in the direction of flow, a step of cooling said first part of the liquid fraction withdrawn from the reactor n in step c) by passing said first part of the liquid fraction into a heat exchanger in order to obtain a cooled liquid fraction, a step of introducing said liquid fraction cooled in step e) at the top of the reaction chamber of said reactor n, the steps a) to f) being carried out, unless indicated otherwise, for each reactor n of the cascade, n being between 1 and N. The invention also relates to a device of N stirred gas/liquid reactors in a cascade, enabling the oligomerization process to be carried out.

The invention relates to a process for the oligomerization of ethylene, carried out at a pressure of between 0.1 and 10.0 MPa, at a temperature of between 30 and 200° C., in a cascade of N gas/liquid reactors in series, N being at least equal to 2, comprising a step of introducing a catalytic oligomerization system into at least the first reactor of the cascade, a step of bringing said catalytic system and an optional solvent into contact with ethylene by introducing said ethylene into the lower part of the reaction chamber of at least the first reactor of the cascade, for each reactor n, a step of withdrawing a liquid fraction in the lower part of the reaction chamber of the reactor n, the liquid fraction being separated into two streams: a first stream corresponding to a first, “main”, part of the liquid fraction, which is conveyed to a heat exchanger for cooling; a second stream corresponding to the second part of the liquid fraction which constitutes the liquid feedstock of the following reactor n+1 in the cascade, a step of introducing said second part of the liquid phase withdrawn from the reactor n towards the reaction chamber of the following reactor n+1 in the direction of flow, a step of cooling said first part of the liquid fraction withdrawn from the reactor n in step c) by passing said first part of the liquid fraction into a heat exchanger in order to obtain a cooled liquid fraction, a step of introducing said liquid fraction cooled in step e) at the top of the reaction chamber of said reactor n, the steps a) to f) being carried out, unless indicated otherwise, for each reactor n of the cascade, n being between 1 and N. The invention also relates to a device of N stirred gas/liquid reactors in a cascade, enabling the oligomerization process to be carried out.

The invention relates to a process for the oligomerization of ethylene, carried out at a pressure of between 0.1 and 10.0 MPa, at a temperature of between 30 and 200° C., in a cascade of N gas/liquid reactors in series, N being at least equal to 2, comprising a step of introducing a catalytic oligomerization system into at least the first reactor of the cascade, a step of bringing said catalytic system and an optional solvent into contact with ethylene by introducing said ethylene into the lower part of the reaction chamber of at least the first reactor of the cascade, for each reactor n, a step of withdrawing a liquid fraction in the lower part of the reaction chamber of the reactor n, the liquid fraction being separated into two streams: a first stream corresponding to a first, “main”, part of the liquid fraction, which is conveyed to a heat exchanger for cooling; a second stream corresponding to the second part of the liquid fraction which constitutes the liquid feedstock of the following reactor n+1 in the cascade, a step of introducing said second part of the liquid phase withdrawn from the reactor n towards the reaction chamber of the following reactor n+1 in the direction of flow, a step of cooling said first part of the liquid fraction withdrawn from the reactor n in step c) by passing said first part of the liquid fraction into a heat exchanger in order to obtain a cooled liquid fraction, a step of introducing said liquid fraction cooled in step e) at the top of the reaction chamber of said reactor n, the steps a) to f) being carried out, unless indicated otherwise, for each reactor n of the cascade, n being between 1 and N. The invention also relates to a device of N stirred gas/liquid reactors in a cascade, enabling the oligomerization process to be carried out.