Disclosed is a cyclopropanation process comprising the step of reacting an alkene compound having at least one carbon-carbon double bond with at least one dihaloalkane. The reaction is carried out in the presence of (i) particulate metal Zn, (ii) catalytically effective amount of particulate metal Cu or a salt thereof, (iii) at least one haloalkylsilane, and (iv) at least one solvent.

A spirally configured cis-stilbene/fluorene hybrid material is shown in formula (1),

##STR00001##

wherein n is 1, 2 or 3, R.sub.1 to R.sub.6 are independently selected from the group consisting of hydrogen atom, halogen atom, cyano group, alkyl group, cycloalkyl group, alkoxy group, amino group, haloalkyl group, thioalkyl group, silyl group, alkenyl group and aromatic ring group, R.sub.8 is a hydrogen atom, tert-butyl group or aryl group, when n is 1, R.sub.7 is a hydrogen atom, diarylamino group or 2-diarylamino-spirobifluorene group, when n is 2 or 3, R.sub.7 is a hydrogen atom, diarylamino group or 2-diarylamino-spirobifluorene group.

A spirally configured cis-stilbene/fluorene hybrid material is shown in formula (1),

##STR00001##

wherein n is 1, 2 or 3, R.sub.1 to R.sub.6 are independently selected from the group consisting of hydrogen atom, halogen atom, cyano group, alkyl group, cycloalkyl group, alkoxy group, amino group, haloalkyl group, thioalkyl group, silyl group, alkenyl group and aromatic ring group, R.sub.8 is a hydrogen atom, tert-butyl group or aryl group, when n is 1, R.sub.7 is a hydrogen atom, diarylamino group or 2-diarylamino-spirobifluorene group, when n is 2 or 3, R.sub.7 is a hydrogen atom, diarylamino group or 2-diarylamino-spirobifluorene group.

Disclosed is a cyclopropanation process comprising the step of reacting an alkene compound having at least one carbon-carbon double bond with at least one dihaloalkane. The reaction is carried out in the presence of (i) particulate metal Zn, (ii) catalytically effective amount of particulate metal Cu or a salt thereof, (iii) at least one haloalkylsilane, and (iv) at least one solvent.

Disclosed is a cyclopropanation process comprising the step of reacting an alkene compound having at least one carbon-carbon double bond with at least one dihaloalkane. The reaction is carried out in the presence of (i) particulate metal Zn, (ii) catalytically effective amount of particulate metal Cu or a salt thereof, (iii) at least one haloalkylsilane, and (iv) at least one solvent.

A method for producing a hydrogenated petroleum resin by reacting dicyclopentadiene with a vinyl aromatic compound, subjecting the reaction product obtained by this reaction to thermal polymerization, and then hydrogenating the resulting product, including the following steps (A) to (C): (A) a preliminary reaction step of reacting a vinyl aromatic compound represented by the following Formula (1) (in the formula, R.sup.1 is a hydrogen atom or the like) with dicyclopentadiene under the condition that selectivity for a phenylnorbornene derivative, which is a reaction product and is represented by the following Formula (2) {in the formula, R.sup.1 has the same meaning as in the above Formula (1)}, is 90% or more to obtain a reaction liquid containing the phenylnorbornene derivative: (B) a polymerization step of heating the reaction liquid, which contains the phenylnorbornene derivative and is obtained in the preliminary reaction step (A), to a temperature of 240 to 300? C. to polymerize the reaction liquid, thereby obtaining a polymerization reaction product; and (C) a hydrogenation step of hydrogenating the polymerization reaction product, which is obtained in the polymerization step (B), in the presence of a catalyst to obtain a hydrogenated petroleum resin. ##STR00001##

A method for producing a hydrogenated petroleum resin by reacting dicyclopentadiene with a vinyl aromatic compound, subjecting the reaction product obtained by this reaction to thermal polymerization, and then hydrogenating the resulting product, including the following steps (A) to (C): (A) a preliminary reaction step of reacting a vinyl aromatic compound represented by the following Formula (1) (in the formula, R.sup.1 is a hydrogen atom or the like) with dicyclopentadiene under the condition that selectivity for a phenylnorbornene derivative, which is a reaction product and is represented by the following Formula (2) {in the formula, R.sup.1 has the same meaning as in the above Formula (1)}, is 90% or more to obtain a reaction liquid containing the phenylnorbornene derivative: (B) a polymerization step of heating the reaction liquid, which contains the phenylnorbornene derivative and is obtained in the preliminary reaction step (A), to a temperature of 240 to 300? C. to polymerize the reaction liquid, thereby obtaining a polymerization reaction product; and (C) a hydrogenation step of hydrogenating the polymerization reaction product, which is obtained in the polymerization step (B), in the presence of a catalyst to obtain a hydrogenated petroleum resin. ##STR00001##

A separation medium consisting of a cyclodextrin metal-organic framework (CD-MOF) for separating aromatic compounds and methods of preparing the same are presented. Bottom-up preparations include the following steps: (a) preparing a first mixture comprising a cyclodextrin, an alkali metal salt, water and an alcohol; (b) performing one of the following two steps: (i) stirring the first mixture; or (ii) adding an amount of a surfactant to the first mixture to form a second mixture; and (c) crystallizing the CD-MOF from the first mixture or the second mixture. Top-down preparations include the following steps: (a) preparing a first mixture comprising the cyclodextrin, an alkali metal salt, water and an alcohol; (b) crystallizing the CD-MOF from the first mixture; and (c) optionally performing particle size reduction of the crystallized CD-MOF. The CD-MOFs are amenable for use in methods for separating alkylaromatic and haloaromatic compounds from a mixture of hydrocarbons.

A separation medium consisting of a cyclodextrin metal-organic framework (CD-MOF) for separating aromatic compounds and methods of preparing the same are presented. Bottom-up preparations include the following steps: (a) preparing a first mixture comprising a cyclodextrin, an alkali metal salt, water and an alcohol; (b) performing one of the following two steps: (i) stirring the first mixture; or (ii) adding an amount of a surfactant to the first mixture to form a second mixture; and (c) crystallizing the CD-MOF from the first mixture or the second mixture. Top-down preparations include the following steps: (a) preparing a first mixture comprising the cyclodextrin, an alkali metal salt, water and an alcohol; (b) crystallizing the CD-MOF from the first mixture; and (c) optionally performing particle size reduction of the crystallized CD-MOF. The CD-MOFs are amenable for use in methods for separating alkylaromatic and haloaromatic compounds from a mixture of hydrocarbons.

A method for producing a hydrogenated petroleum resin by reacting dicyclopentadiene with a vinyl aromatic compound, subjecting the reaction product obtained by this reaction to thermal polymerization, and then hydrogenating the resulting product, including the following steps (A) to (C): (A) a preliminary reaction step of reacting a vinyl aromatic compound represented by the following Formula (1) (in the formula, R.sup.1 is a hydrogen atom or the like) with dicyclopentadiene under the condition that selectivity for a phenylnorbornene derivative, which is a reaction product and is represented by the following Formula (2) {in the formula, R.sup.1 has the same meaning as in the above Formula (1)}, is 90% or more to obtain a reaction liquid containing the phenylnorbornene derivative: (B) a polymerization step of heating the reaction liquid, which contains the phenylnorbornene derivative and is obtained in the preliminary reaction step (A), to a temperature of 240 to 300 C. to polymerize the reaction liquid, thereby obtaining a polymerization reaction product; and (C) a hydrogenation step of hydrogenating the polymerization reaction product, which is obtained in the polymerization step (B), in the presence of a catalyst to obtain a hydrogenated petroleum resin.

##STR00001##