Processes for making bicyclic compounds and precursors thereof, and particularly for making [1.1.1]propellane and bicyclo[1.1.1]pentane and derivatives thereof, utilize continuous flow reaction methods and conditions. A continuous process for making [1.1.1]propellane can be conducted under reaction conditions that advantageously minimize clogging of a continuous flow reactor. A continuous flow process can be used to make precursors of [1.1.1]propellane.

Processes for making bicyclic compounds and precursors thereof, and particularly for making [1.1.1]propellane and bicyclo[1.1.1]pentane and derivatives thereof, utilize continuous flow reaction methods and conditions. A continuous process for making [1.1.1]propellane can be conducted under reaction conditions that advantageously minimize clogging of a continuous flow reactor. A continuous flow process can be used to make precursors of [1.1.1]propellane.

A gas separation method including performing a gas separation operation that separates a source gas into a primary-side gas and a secondary-side gas with a membrane of a membrane module. The source gas contains a combustible component. The gas separation operation includes pressurizing the source gas and supplying the source gas to a primary side of the membrane module and depressurizing a secondary side of the membrane module to a pressure lower than an atmospheric pressure. The primary-side gas has a higher concentration of the combustible component than the secondary-side gas, and the gas separation method further includes detecting a composition of the secondary-side gas and stopping the gas separation operation in an instance in which the composition enters a specified range.

A gas separation method including performing a gas separation operation that separates a source gas into a primary-side gas and a secondary-side gas with a membrane of a membrane module. The source gas contains a combustible component. The gas separation operation includes pressurizing the source gas and supplying the source gas to a primary side of the membrane module and depressurizing a secondary side of the membrane module to a pressure lower than an atmospheric pressure. The primary-side gas has a higher concentration of the combustible component than the secondary-side gas, and the gas separation method further includes detecting a composition of the secondary-side gas and stopping the gas separation operation in an instance in which the composition enters a specified range.

The present invention concerns a method (100) for the production of a propylene product (9) in which a component mixture (2) containing propane, propylene and hydrogen is provided using a propane dehydrogenation (10) to which a reaction feed (1) containing propane and hydrogen is subjected, the component mixture (2) or a part thereof being subjected as a first separation feed to a first membrane separation (40), by means of which a first permeate (3) enriched in hydrogen with respect to the first separation feed and a first retentate (4) depleted in hydrogen with respect to the first separation feed and containing hydrogen, propane and propylene are formed, the first retentate (4) or part thereof being subjected to a second membrane separation (50) as a second separation feed, in which a second permeate (6) containing at least the predominant part of the hydrogen of the second separation feed and a second retentate containing at least the predominant part of the propane and the propylene of the second separation feed are formed, wherein the first membrane separation (40) is carried out using a sweep gas (5) containing propane and the first permeate (3) is obtained as a permeate (3) charged with propane of the sweep gas (5) and/or the second membrane separation (50) is carried out using the sweep gas (5) containing propane and the second permeate (6) is obtained as a permeate (6) charged with propane of the sweep gas (5), and wherein the first permeate (3) charged with propane of the sweep gas (5) and/or the second permeate (3) charged with propane of the sweep gas or one or more parts thereof is used in the formation of the reaction feed (1). A corresponding plant is also the subject of this invention.

The present invention concerns a method (100) for the production of a propylene product (9) in which a component mixture (2) containing propane, propylene and hydrogen is provided using a propane dehydrogenation (10) to which a reaction feed (1) containing propane and hydrogen is subjected, the component mixture (2) or a part thereof being subjected as a first separation feed to a first membrane separation (40), by means of which a first permeate (3) enriched in hydrogen with respect to the first separation feed and a first retentate (4) depleted in hydrogen with respect to the first separation feed and containing hydrogen, propane and propylene are formed, the first retentate (4) or part thereof being subjected to a second membrane separation (50) as a second separation feed, in which a second permeate (6) containing at least the predominant part of the hydrogen of the second separation feed and a second retentate containing at least the predominant part of the propane and the propylene of the second separation feed are formed, wherein the first membrane separation (40) is carried out using a sweep gas (5) containing propane and the first permeate (3) is obtained as a permeate (3) charged with propane of the sweep gas (5) and/or the second membrane separation (50) is carried out using the sweep gas (5) containing propane and the second permeate (6) is obtained as a permeate (6) charged with propane of the sweep gas (5), and wherein the first permeate (3) charged with propane of the sweep gas (5) and/or the second permeate (3) charged with propane of the sweep gas or one or more parts thereof is used in the formation of the reaction feed (1). A corresponding plant is also the subject of this invention.

The present invention concerns a method (100) for the production of a propylene product (9) in which a component mixture (2) containing propane, propylene and hydrogen is provided using a propane dehydrogenation (10) to which a reaction feed (1) containing propane and hydrogen is subjected, the component mixture (2) or a part thereof being subjected as a first separation feed to a first membrane separation (40), by means of which a first permeate (3) enriched in hydrogen with respect to the first separation feed and a first retentate (4) depleted in hydrogen with respect to the first separation feed and containing hydrogen, propane and propylene are formed, the first retentate (4) or part thereof being subjected to a second membrane separation (50) as a second separation feed, in which a second permeate (6) containing at least the predominant part of the hydrogen of the second separation feed and a second retentate containing at least the predominant part of the propane and the propylene of the second separation feed are formed, wherein the first membrane separation (40) is carried out using a sweep gas (5) containing propane and the first permeate (3) is obtained as a permeate (3) charged with propane of the sweep gas (5) and/or the second membrane separation (50) is carried out using the sweep gas (5) containing propane and the second permeate (6) is obtained as a permeate (6) charged with propane of the sweep gas (5), and wherein the first permeate (3) charged with propane of the sweep gas (5) and/or the second permeate (3) charged with propane of the sweep gas or one or more parts thereof is used in the formation of the reaction feed (1). A corresponding plant is also the subject of this invention.

The present invention concerns a process (100) for the production of a butylene product (9) in which a component mixture (2) containing butane, butylene and hydrogen is provided using a butane hydrogenation (10) to which a reaction feed (1) containing butane and hydrogen is subjected, the component mixture (2) or part thereof being subjected as a first separation feed to a first membrane separation (40), by means of which a first permeate (3) enriched in hydrogen with respect to the first separation feed and a first retentate (4) depleted in hydrogen with respect to the first separation feed and containing hydrogen, butane and butylene are formed, the first retentate (4) or part thereof being subjected to a second membrane separation (50) as a second separation feed, in which a second permeate (6) containing at least the predominant part of the hydrogen of the second separation feed and a second retentate containing at least the predominant part of the butane and the butylene of the second separation feed are formed, wherein the first membrane separation (40) is carried out using a sweep gas (5) containing butane and the first permeate (3) is obtained as permeate (3) charged with butane of the sweep gas (5) and/or the second membrane separation (50) is carried out using the sweep gas (5) containing butane and the second permeate (6) is obtained as permeate (6) charged with butane of the sweep gas (5), and wherein the first permeate (3) charged with butane of the sweep gas (5) and/or the second permeate (3) charged with butane of the sweep gas or one or more parts thereof is used in the formation of the reaction feed (1). A corresponding plant is also the subject of this invention.

The present invention concerns a process (100) for the production of a butylene product (9) in which a component mixture (2) containing butane, butylene and hydrogen is provided using a butane hydrogenation (10) to which a reaction feed (1) containing butane and hydrogen is subjected, the component mixture (2) or part thereof being subjected as a first separation feed to a first membrane separation (40), by means of which a first permeate (3) enriched in hydrogen with respect to the first separation feed and a first retentate (4) depleted in hydrogen with respect to the first separation feed and containing hydrogen, butane and butylene are formed, the first retentate (4) or part thereof being subjected to a second membrane separation (50) as a second separation feed, in which a second permeate (6) containing at least the predominant part of the hydrogen of the second separation feed and a second retentate containing at least the predominant part of the butane and the butylene of the second separation feed are formed, wherein the first membrane separation (40) is carried out using a sweep gas (5) containing butane and the first permeate (3) is obtained as permeate (3) charged with butane of the sweep gas (5) and/or the second membrane separation (50) is carried out using the sweep gas (5) containing butane and the second permeate (6) is obtained as permeate (6) charged with butane of the sweep gas (5), and wherein the first permeate (3) charged with butane of the sweep gas (5) and/or the second permeate (3) charged with butane of the sweep gas or one or more parts thereof is used in the formation of the reaction feed (1). A corresponding plant is also the subject of this invention.

The present invention concerns a process (100) for the production of a butylene product (9) in which a component mixture (2) containing butane, butylene and hydrogen is provided using a butane hydrogenation (10) to which a reaction feed (1) containing butane and hydrogen is subjected, the component mixture (2) or part thereof being subjected as a first separation feed to a first membrane separation (40), by means of which a first permeate (3) enriched in hydrogen with respect to the first separation feed and a first retentate (4) depleted in hydrogen with respect to the first separation feed and containing hydrogen, butane and butylene are formed, the first retentate (4) or part thereof being subjected to a second membrane separation (50) as a second separation feed, in which a second permeate (6) containing at least the predominant part of the hydrogen of the second separation feed and a second retentate containing at least the predominant part of the butane and the butylene of the second separation feed are formed, wherein the first membrane separation (40) is carried out using a sweep gas (5) containing butane and the first permeate (3) is obtained as permeate (3) charged with butane of the sweep gas (5) and/or the second membrane separation (50) is carried out using the sweep gas (5) containing butane and the second permeate (6) is obtained as permeate (6) charged with butane of the sweep gas (5), and wherein the first permeate (3) charged with butane of the sweep gas (5) and/or the second permeate (3) charged with butane of the sweep gas or one or more parts thereof is used in the formation of the reaction feed (1). A corresponding plant is also the subject of this invention.