Abstract: Provided is a separation membrane that is suitable for use in separating one or more hydrocarbons from a hydrocarbon mixture. More specifically, the separation membrane includes a porous support for which acid content is not substantially detected by ammonia temperature programmed desorption in a temperature range of higher than 450° C. and not higher than 600° C. and a porous separation layer containing a zeolite that is disposed on the porous support.

Abstract: Provided is a separation membrane that is suitable for use in separating one or more hydrocarbons from a hydrocarbon mixture. More specifically, the separation membrane includes a porous support for which acid content is not substantially detected by ammonia temperature programmed desorption in a temperature range of higher than 450° C. and not higher than 600° C. and a porous separation layer containing a zeolite that is disposed on the porous support.

Abstract: Provided are a membrane separation method and a membrane separation device that enable membrane separation of a hydrocarbon mixture with high separation efficiency. The membrane separation method includes a step (A) of exposing a zeolite membrane to an atmosphere having a dew point of ?20° C. or lower and a step (B) of using the zeolite membrane to perform membrane separation of a hydrocarbon mixture after step (A). The membrane separation device includes: a membrane separation module including a housing and a zeolite membrane that is housed in the housing and is configured to perform membrane separation of a hydrocarbon mixture; a feedstock supply mechanism configured to supply the hydrocarbon mixture into the membrane separation module; and a gas supply mechanism configured to supply a gas having a dew point of ?20° C. or lower into a space in which the zeolite membrane is housed in the membrane separation module.

Abstract: The present invention is a method for producing a cyclopentyl alkyl ether compound represented by formula (1): R1—O—R2 (wherein, R1 represents an alkyl group having 1 to 10 carbon atoms that may have a substituent or a cycloalkyl group having 3 to 8 carbon atoms that may have a substituent, and R2 represents a cyclopentyl group that may have a substituent), wherein a cyclopentene that may have a substituent is reacted with an alcohol compound represented by formula (2): R1OH (wherein R1 represents the same as described above) in the presence of an acidic zeolite having a silica/alumina ratio of 80 or higher. The present invention provides a method for producing a cyclopentyl alkyl ether compound, wherein a reaction can be carried out in a liquid phase, catalyst activity is less lowered over time (long catalyst life), and a desired cyclopentyl alkyl ether compound can be continuously produced with high reaction efficiency and long-term stability even when a large amount of raw material is fed.

Abstract: The present invention is a method for producing a cycloalkyl alkyl ether compound comprising reacting substituted or unsubstituted cyclopentene or substituted or unsubstituted cyclohexene with an alcohol compound represented by a formula (2): R1OH (wherein R1 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms) in a gaseous state in presence of an acidic ion-exchange resin to produce a cycloalkyl alkyl ether compound represented by a formula (1): R1—O—R2 (wherein R1 is the same as defined above, and R2 is a substituted or unsubstituted cyclopentyl group or a substituted or unsubstituted cyclohexyl group), the acidic ion-exchange resin having a specific surface area of 20 to 50 m2/g, an average pore size of 20 to 70 nm, and a total exchange capacity of 4.8 to 6.0 eq/L-R wet resin.

Abstract: The present invention is a method for producing a cycloalkyl alkyl ether compound comprising reacting substituted or unsubstituted cyclopentene or substituted or unsubstituted cyclohexene with an alcohol compound represented by a formula (2): R1OH (wherein R1 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms) in a gaseous state in presence of an acidic ion-exchange resin to produce a cycloalkyl alkyl ether compound represented by a formula (1): R1—O—R2 (wherein R1 is the same as defined above, and R2 is a substituted or unsubstituted cyclopentyl group or a substituted or unsubstituted cyclohexyl group), the acidic ion-exchange resin having a specific surface area of 20 to 50 m2/g, an average pore size of 20 to 70 nm, and a total exchange capacity of 4.8 to 6.0 eq/L-R wet resin.