JPH0977689A - Hydrogenation of olefins - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a hydrogenation product of an olefin in the presence of a catalyst high in hydrogenation activity in a high yield by reacting the olefin with hydrogen in the presence of the catalyst comprising a metallocene compound and an organic aluminum compound. SOLUTION: An olefin (preferably a cycloalkadiene) is reacted with hydrogen in the presence of (A) a metallocene compound and (B) an organic aluminum oxy compound (preferably methylaluminoxane) preferably at 20-100 deg.C for 1-30hr. The component A is preferably a zirconocene of the formula: MLx (M is zirconium; L groups are ligands, wherein at least one of the L groups is a ligand having a cyclopentadienyl skeleton, and the others are each a 1-12C hydrocarbon, an alkoxy, etc.; x is the valency of M). The component A and the component B are used in amounts of 0.001-0.1 mole and 0.01-1 mole, respectively, per mole of the olefin. The components A and B are used in an Al/M atomic ratio of 100-500.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a method for hydrogenating olefins, and more particularly to a method for hydrogenating olefins using a catalyst.

[0002]

2. Description of the Related Art Conventionally, as a method for hydrogenating olefins, various catalysts have been known. For example, a method using titanocene and an aluminum hydride derivative (JP-A-54-4292). Gazette), titanocene,
A method using alkyllithium and organoaluminum (JP-A-60-220147) and a method using titanocene and alkyllithium (JP-A-61-1206).
33132, JP-A-61-47706, JP-A-61-57524), a method using titanocene, zirconocene or hafnocene and trialkylaluminum (JP-A-2-172537) and titanocene. There is a method using triisobutylaluminum (JP-A-5-286870), a method using titanocene and an additive (JP-A-7-2702), and the like. However, a method of using a metallocene compound and methylaluminoxane in combination as a catalyst is not known.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to propose a method for hydrogenating olefins which makes it possible to obtain hydrogenated products in high yield using a catalyst having high hydrogenation activity.

[0004]

The present invention is the following method for hydrogenating olefins. (1) A method for hydrogenating olefins, which comprises reacting olefins with hydrogen in the presence of a metallocene compound and an organoaluminumoxy compound. (2) The method according to (1) above, wherein the metallocene compound is a zirconocene compound. (3) The above (1) or (2), wherein the organoaluminum oxy compound is methylaluminoxane.
The described method. (4) The method according to any one of (1) to (3) above, wherein the olefins are cycloolefins. (5) The method according to (4) above, wherein the cycloolefins are monoenes or dienes. (6) A method for hydrogenating an olefin, which comprises reacting an olefin with hydrogen in the presence of a zirconocene compound having an alkyl-substituted cyclopentadienyl group as a ligand and methylaluminoxane to obtain an alkane. (7) A method for hydrogenating an olefin, which comprises reacting an olefin with hydrogen in the presence of a zirconocene compound having an ethylenebisindenyl group as a ligand and methylaluminoxane to obtain an alkane. (8) In the presence of a zirconocene compound having a dialkylmethylene (cyclopentadienyl-fluorenyl) group as a ligand and methylaluminoxane, an olefin is reacted with hydrogen to obtain an alkane. Hydrogenation method. (9) Hydrogenation of olefins, characterized in that an alkane is obtained by reacting an olefin with hydrogen in the presence of a zirconocene compound having a dialkylsilylenebis (phenylindenyl) group as a ligand and methylaluminoxane. Method. (10) An olefin characterized by obtaining an alkane by reacting an olefin with hydrogen in the presence of a zirconocene compound having a dialkylsilylenebis (phenanthrenylindenyl) group as a ligand and methylaluminoxane. Hydrogenation method.

The olefins which can be hydrogenated by the method of the present invention are not limited as long as they are compounds having one or more olefinic double bonds in the molecule, and those having a chain structure or a cyclic structure can be used. Cycloolefins which are cyclic olefins such as cycloalkene, cycloalkadiene, cycloalkatriene and cycloalkatetraene; chain olefins, chain diene compounds, chain triene compounds, chains Examples include chain olefins such as formula tetraene compounds. These olefins may be substituted with an alkyl group having 1 to 5 carbon atoms such as methyl, ethyl, propyl, butyl and pentyl, and a functional group such as halogen, hydroxyl group and carboxyl group. Of these, cycloolefins are preferable, and among them, a cycloalkene having one olefinic double bond or a cycloalkadiene having two olefinic double bonds is particularly preferable.

Specific examples of the cycloalkene include cycloalkene having 5 to 12 carbon atoms such as cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclodecene and cyclododecene.

Specific examples of the cycloalkadiene include cycloalkadiene having 4 to 12 carbon atoms such as cyclobutadiene, cyclopentadiene, cyclohexadiene, cyclooctadiene and cyclododecadien. Examples of the cycloalkatriene include cycloalkatriene having 7 to 12 carbon atoms such as cyclododecatriene. Examples of the cycloalkatetraene include cycloalkatetraene having 8 to 12 carbon atoms such as cyclooctatetraene.

Specific examples of the chain olefin include chain olefins having 1 to 16 carbon atoms such as ethylene, propylene, butene, pentene, hexene, octene, decene, dodecene, tetradecene and hexadecene.

Examples of the chain diene compound include chain diene compounds having 4 to 12 carbon atoms such as butadiene, pentadiene, hexadiene, octadiene and dodecadiene. Examples of the chain triene compound include chain triene compounds having 4 to 12 carbon atoms such as hexatriene and dodecatriene.

The metallocene compound constituting the hydrogenation catalyst used in the present invention is a periodical system containing at least one ligand having a cyclopentadienyl skeleton such as 5-membered cyclopentadienyl or its derivative. It is a transition metal compound of Group 4 in the table. Such metallocene compounds are preferably those represented by the following general formula (1).

ML _x (1) (wherein M represents a transition metal atom selected from Group 4 of the periodic table, L represents a ligand coordinated to the transition metal, and at least one L is L is a ligand having a cyclopentadienyl skeleton, and L other than the ligand having a cyclopentadienyl skeleton is a hydrocarbon group having 1 to 12 carbon atoms, an alkoxy group, an aryloxy group, a trialkylsilyl group, SO ₃ R ¹
A group (wherein R ¹ represents a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent such as halogen), a halogen atom or a hydrogen atom, and x represents a valence of the transition metal. . )

In the above general formula (1), M is a transition metal atom selected from Group 4 of the periodic table, specifically, a zirconium atom, a titanium atom or a hafnium atom, of which the zirconium atom is preferable.

Examples of the ligand having a cyclopentadienyl skeleton include cyclopentadienyl group, methylcyclopentadienyl group, dimethylcyclopentadienyl group, trimethylcyclopentadienyl group, tetramethylcyclopentadienyl group. Group, pentamethylcyclopentadienyl group, ethylcyclopentadienyl group, methylethylcyclopentadienyl group, propylcyclopentadienyl group, methylpropylcyclopentadienyl group, butylcyclopentadienyl group, methylbutylcyclo Examples thereof include an alkyl-substituted cyclopentadienyl group such as a pentadienyl group and a hexylcyclopentadienyl group, an indenyl group, a 4,5,6,7-tetrahydroindenyl group, and a fluorenyl group. These groups may be substituted with a halogen atom, a trialkylsilyl group or the like.

When the compound represented by the above general formula (1) contains two or more ligands having a cyclopentadienyl skeleton, the ligands having two cyclopentadienyl skeletons among them are , Alkylene groups such as ethylene and propylene, substituted alkylene groups such as isopropylidene and diphenylmethylene, silylene groups or dimethylsilylene groups, diphenylsilylene groups, and substituted silylene groups such as methylphenylsilylene groups. .

Specific examples of the ligand L other than the ligand having a cyclopentadienyl skeleton include the following. As the hydrocarbon group having 1 to 12 carbon atoms,
Examples thereof include an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, and the like. More specifically, examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. Examples thereof include a cyclopentyl group and a cyclohexyl group, examples of the aryl group include a phenyl group and tolyl group, and examples of the aralkyl group include a benzyl group and a neophyll group.

As the alkoxy group, a methoxy group,
Examples of the ethoxy group, butoxy group and the like, examples of the aryloxy group include a phenoxy group and the like, examples of the trialkylsilyl group include a trimethylsilyl group, and examples of the ligand represented by SO ₃ R ¹ include: Examples thereof include p-toluenesulfonato group, methanesulfonato group, trifluoromethanesulfonato group and the like.

Halogen includes fluorine, chlorine, bromine,
Examples thereof include iodine. Such a transition metal compound containing a ligand having a cyclopentadienyl skeleton is more specifically represented by the following general formula (1a) when the valence of the transition metal is 4.

R ² _k R ³ _l R ⁴ _m R ⁵ _n M (1a) (wherein M represents a transition metal atom and R ² represents a group (ligand) having a cyclopentadienyl skeleton. , R ³ , R ⁴ and R ⁵ are groups having a cyclopentadienyl skeleton (ligand), alkyl groups, cycloalkyl groups, aryl groups, aralkyl groups, alkoxy groups, aryloxy groups, trialkylsilyl groups, SO ₃ R ¹ group, a halogen atom or a hydrogen atom, k is an integer of 1 or more, and k + l + m + n =
4. )

In the present invention, in the transition metal compound represented by the general formula (1a), at least one of R ³ , R ⁴ and R ⁵ is a group (ligand) having a cyclopentadienyl skeleton. For example, compounds in which R ² and R ³ are groups (ligands) having a cyclopentadienyl skeleton are preferably used. Thus, the above general formula (1
When the compound represented by a) contains two or more groups (ligands) having a cyclopentadienyl skeleton, two of them are
Groups (ligands) each having one cyclopentadienyl skeleton are alkylene groups such as ethylene and propylene, substituted alkylene groups such as isopropylidene and diphenylmethylene, silylene groups or dimethylsilylene, diphenylsilylene, methylphenylsilylene, etc. May be bound via a substituted silylene group of Further, R ² and R ³ are groups (ligands) having a cyclopentadienyl skeleton
And R ⁴ and R ⁵ are groups having a cyclopentadienyl skeleton, alkyl groups, cycloalkyl groups, aryl groups, aralkyl groups, alkoxy groups, aryloxy groups, trialkylsilyl groups, SO ₃ R ¹ , halogen atoms Or a hydrogen atom.

Specific examples of transition metal compounds in which M is zirconium, that is, zirconocene compounds, will be shown below. Bis (indenyl) zirconium dichloride, bis (indenyl) zirconium dibromide, bis (indenyl) zirconium bis (p-toluenesulfonato), bis (4,5,6,7-tetrahydroindenyl) zirconium dichloride, bis (fluorenyl) Zirconium dichloride, ethylenebis (indenyl) zirconium dichloride, ethylenebis (indenyl) zirconium dibromide, ethylenebis (indenyl) dimethylzirconium, ethylenebis (indenyl) diphenylzirconium, ethylenebis (indenyl) methylzirconium monochloride, ethylenebis (indenyl) ) Zirconium bis (methane sulfonate), ethylene bis (indenyl) zirconium bis (p-toluene sulfonate), ethylene bis (indenyl) dil Conium bis (trifluoromethanesulfonato), ethylene bis (4,5,6,7-tetrahydroindenyl) zirconium dichloride, isopropylidene (cyclopentadienyl-fluorenyl) zirconium dichloride, isopropylidene (cyclopentadienyl-methylcyclopenta) Dienyl) zirconium dichloride, dimethylsilylenebis (cyclopentadienyl) zirconium dichloride, dimethylsilylenebis (methylcyclopentadienyl) zirconium dichloride, dimethylsilylenebis (dimethylcyclopentadienyl) zirconium dichloride, dimethylsilylenebis (trimethylcyclo) Pentadienyl) zirconium dichloride, dimethylsilylene bis (indenyl) zirconium dichloride, dimethylsilylene bis (indene Le) zirconium bis (trifluoromethanesulfonate), dimethylsilylene-bis (4,5,6,
7-tetrahydroindenyl) zirconium dichloride,
Dimethyl silylene (cyclopentadienyl-fluorenyl) zirconium dichloride, diphenyl silylene bis (indenyl) zirconium dichloride, methylphenyl silylene bis (indenyl) zirconium dichloride, bis (cyclopentadienyl) zirconium dichloride, bis (cyclopentadienyl) zirconium Dibromide, bis (cyclopentadienyl) methylzirconium monochloride, bis (cyclopentadienyl) ethylzirconium monochloride, bis (cyclopentadienyl) cyclohexylzirconium monochloride, bis (cyclopentadienyl) phenylzirconium monochloride , Bis (cyclopentadienyl) benzyl zirconium monochloride, bis (cyclopentadienyl) zirconium monochloride Domonohydride, bis (cyclopentadienyl) methylzirconium monohydride, bis (cyclopentadienyl) dimethylzirconium, bis (cyclopentadienyl) diphenylzirconium, bis (cyclopentadienyl) dibenzylzirconium, bis (cyclo Pentadienyl) zirconium methoxy chloride, bis (cyclopentadienyl) zirconium ethoxy chloride, bis (cyclopentadienyl) zirconium bis (methanesulfonato), bis (cyclopentadienyl) zirconium bis (p-toluenesulfonato) Bis (cyclopentadienyl) zirconium bis (trifluoromethanesulfonato), bis (methylcyclopentadienyl) zirconium dichloride, bis (dimethylcyclopentadienyl) zil Bis (dimethylcyclopentadienyl) zirconium ethoxy chloride, bis (dimethylcyclopentadienyl) zirconium bis (trifluoromethanesulfonato), bis (ethylcyclopentadienyl) zirconium dichloride, bis (methylethylcyclopentadiene) (Enyl) zirconium dichloride, bis (propylcyclopentadienyl) zirconium dichloride, bis (methylpropylcyclopentadienyl) zirconium dichloride, bis (butylcyclopentadienyl) zirconium dichloride, bis (methylbutylcyclopentadienyl) zirconium dichloride , Bis (methylbutylcyclopentadienyl) zirconium bis (methanesulfonato), bis (trimethylcyclopentadienyl) zirconium Mudichloride, bis (tetramethylcyclopentadienyl) zirconium dichloride, bis (pentamethylcyclopentadienyl) zirconium dichloride, bis (hexylcyclopentadienyl) zirconium dichloride, bis (trimethylsilylcyclopentadienyl) zirconium dichloride.

In the above examples, the di-substituted cyclopentadienyl ring includes 1,2- and 1,3-substituted compounds, and the tri-substituted compound is 1,2,3- and 1,2,4-substituted compounds. Including the body. Alkyl groups such as propyl and butyl are n-, i-, sec-, tert-
Including isomers such as. In the present invention, in the zirconium compound as described above, a compound in which a zirconium atom is replaced with a transition metal atom such as a titanium atom or a hafnium atom can also be used.

Next, the organoaluminum oxy compound constituting the hydrogenation catalyst used in the present invention will be described. The organoaluminum oxy compound may be a conventionally known benzene-soluble aluminoxane or a benzene-insoluble or sparingly soluble organoaluminum oxy compound as disclosed in JP-A-2-276807.

Examples of the benzene-soluble aluminoxane include aluminoxanes represented by the following general formula (2) or (3).

Embedded image (In the formula, R ⁶ represents a hydrocarbon group, and p represents an integer of 2 or more.)

In the aluminoxane represented by the general formula (2) or (3), R ⁶ is an alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group, and p
Is preferably 5 or more, more preferably methylaluminoxane in which R ⁶ is a methyl group.

The above-mentioned conventionally known benzene-soluble aluminoxane can be produced, for example, by the following method. (1) Compounds containing adsorbed water or salts containing water of crystallization, such as magnesium chloride hydrate, copper sulfate hydrate, aluminum sulfate hydrate, nickel sulfate hydrate, ceric chloride hydrate, etc. A method of adding an organoaluminum compound such as trialkylaluminum to the hydrocarbon medium suspension of, and reacting the organoaluminum compound with adsorption water or crystallization water.

(2) A method of directly acting water, ice or steam on an organoaluminum compound such as trialkylaluminum in a medium such as benzene, toluene, ethyl ether or tetrahydrofuran.

(3) A method of reacting an organoaluminum compound such as trialkylaluminum with an organotin oxide such as dimethyltin oxide or dibutyltin oxide in a medium such as decane, benzene or toluene.

The aluminoxane may contain a small amount of organic metal component. Alternatively, the solvent or unreacted organoaluminum compound may be removed from the recovered aluminoxane solution by distillation, and then redissolved in the solvent.

Specific examples of the organoaluminum compound used when preparing the aluminoxane include trimethylaluminum, triethylaluminum, tripropylaluminum, triisopropylaluminum, and tri-n-.
Trialkyl aluminum such as butyl aluminum, triisobutyl aluminum, tri sec-butyl aluminum, tri tert-butyl aluminum, tripentyl aluminum, trihexyl aluminum, trioctyl aluminum, tridecyl aluminum; tricyclohexyl aluminum, tricyclooctyl aluminum, etc. Tricycloalkyl aluminum; Dialkyl aluminum halides such as dimethyl aluminum chloride, diethyl aluminum chloride, diethyl aluminum bromide, diisobutyl aluminum chloride; Dialkyl aluminum hydrides such as diethyl aluminum hydride and diisobutyl aluminum hydride; Dimethyl aluminum methoxide, diethyl aluminum ethoxy Dialkylaluminum alkoxides such as diethyl aluminum phenoxide dialkylaluminum arylene Loki Cid, etc., and the like. Of these, trialkylaluminums and tricycloalkylaluminums are particularly preferred.

Further, as the organoaluminum compound represented by the following general formula _{(i-C 4 H 9)} x Al y (C 5 H 10) z (x, y, z are positive numbers, it is z ≧ 2x It is also possible to use isoprenylaluminum represented by The above organoaluminum compounds are used alone or in combination.

The solvent used in the preparation of the aluminoxane is benzene, toluene, xylene, cumene,
Aromatic hydrocarbons such as cymene; pentane, hexane, heptane, octane, decane, dodecane, hexadecane,
Aliphatic hydrocarbons such as octadecane; cyclopentane,
Alicyclic hydrocarbons such as cyclohexane, cyclooctane, and methylcyclopentane; petroleum fractions such as gasoline, kerosene, and light oil, or halides of the above aromatic hydrocarbons, aliphatic hydrocarbons, alicyclic hydrocarbons, especially chlorinated products And hydrocarbon solvents such as bromide. In addition, ethers such as ethyl ether and tetrahydrofuran can also be used. Of these solvents, aromatic hydrocarbons are particularly preferable.

The benzene-insoluble or sparingly soluble organoaluminum oxy compound disclosed in JP-A-2-276807 as the organoaluminum oxy compound used in the present invention is, for example, a method in which water is reacted with the aluminoxane, or Examples thereof include an organoaluminum oxy compound obtained by a method such as a method of reacting water or a compound containing active hydrogen with a hydrocarbon solution of the organoaluminum compound.

The benzene-insoluble organoaluminum oxy compound obtained by the above method is represented by the general formula (4)

Embedded image (In the formula, R ⁷ represents a hydrocarbon group having 1 to 12 carbon atoms.)
It is presumed to have an alkyloxyaluminum unit represented by

The above-mentioned organoaluminum oxy compound used in the present invention is commercially available or handled as a solution or dispersion prepared by dissolving or dispersing in an organic solvent such as toluene. The hydrogenation catalyst used in the present invention is a catalyst containing the metallocene compound and the organoaluminumoxy compound as essential components.

The hydrogenation in the present invention can be carried out by reacting the olefins with hydrogen in the presence of the metallocene compound and the organoaluminum compound. In this case, the amount of the metallocene compound used is 0.00001 to 0.5 mol per 1 mol of the olefin,
It is preferably 0.001 to 0.1 mol. The amount of the organoaluminum oxy compound used is 0.0001 to 5 mol, preferably 0.01 to 1.0 mol, per 1 mol of olefins. The ratio of the metallocene compound and the organoaluminum compound used in the hydrogenation reaction of the present invention is 1 to 1000, preferably 100 to 500, expressed as the atomic ratio of Al / M. Here, M represents a transition metal atom in the general formula (1).

As a method of reacting olefins with hydrogen, a method of introducing hydrogen into a reactor holding olefins and reacting with or without pressurization to a predetermined pressure can be adopted. When pressurizing, the pressure of hydrogen is 0.1 to 10 MPa, preferably 0.5 to 5 MPa.

The hydrogenation reaction can be carried out without using a reaction medium, but it is preferably used. As the reaction medium, aromatic hydrocarbons such as benzene, toluene, xylene, cumene and cymene; pentane, hexane, heptane,
Aliphatic hydrocarbons such as octane, decane, dodecane, hexadecane, and octadecane; Alicyclic hydrocarbons such as cyclopentane, cyclohexane, cyclooctane, and methylcyclopentane; Petroleum fractions such as gasoline, kerosene, and light oil, or the above aromatic carbons Hydrogen, aliphatic hydrocarbons, halides of alicyclic hydrocarbons and the like can be used, and also metallocene compounds or organoaluminum oxy compounds can be prepared,
It is also possible to use the solvent used for storage.

The reaction conditions are such that the temperature is 0 to 200 ° C., preferably 20 to 100 ° C., and the time is 0.1 to 100 hours, preferably 1 to 30 hours. By carrying out the reaction in this manner, the olefinic double bond of the olefins is hydrogenated and reduced to obtain a hydrogenated product. For example, when a cycloalkene is hydrogenated, a cycloalkane is obtained, and in the case of olefins having a plurality of olefinic double bonds such as cycloalkadiene and cycloalkatriene, the number of olefinic double bonds is A cycloalkene, a mixture of cycloalkadiene and cycloalkane which is one or more less than these, or a cycloalkane is finally obtained when the hydrogenation reaction is sufficiently carried out.

[0039]

EFFECTS OF THE INVENTION Since the hydrogenation method of the present invention uses a metallocene compound and an organoaluminumoxy compound having high hydrogenation activity as catalysts, it is possible to easily hydrogenate olefins with a high yield. A hydrogenated product can be obtained.

[0040]

BEST MODE FOR CARRYING OUT THE INVENTION Next, embodiments of the present invention will be described. Examples 1 to 9 After a stainless autoclave having a volume of 50 ml equipped with a stirrer and a ventilation valve was replaced with argon, 280 mg (2.54 mmol) of cyclooctene and 8.5 ml of 1 mM hexane solution of the metallocene compound shown in Table 1 (metallocene compound As 8.5 μmol), toluene 8 m
1, a 6% by weight solution of methylaluminoxane in toluene 2.
0 ml (1.7 mmol as methylaluminoxane)
Was charged. Next, while applying a hydrogen pressure of 4 MPa, 80 ° C.
The temperature was raised to 2, and the reaction was performed for 2 hours. Then, the analysis of the reaction product was performed using gas chromatography. The results are shown in Table 1.

Comparative Examples 1 to 3 Hydrogenation was carried out in the same manner as in Example 1 except that the compounds shown in Table 1 were used as catalysts. The results are shown in Table 1.

Examples 10 to 12 2.4 ml of toluene in a 30 ml Schlenk bottle sufficiently replaced with nitrogen, 0.005 m of metallocene compound shown in Table 2
0.5 ml of toluene containing mol, 0.6 ml of a toluene solution of methylaluminoxane (1.0 mmo in terms of Al)
1) was charged and stirred at room temperature for 30 minutes. Next, after replacing the system with hydrogen, 1,3-cyclooctadiene 1.5 mmo
1.5 ml of toluene containing 1 was added, and 2 at room temperature and atmospheric pressure was added.
The hydrogenation reaction was carried out for 0 hours. Then, the analysis of the reaction product was performed using gas chromatography. Table 2 shows the results.

Comparative Example 4 1.5 ml of a decane solution of triisobutylaluminum instead of methylaluminoxane (1.5 mm in terms of Al)
reaction was carried out in the same manner as in Example 10 except that Table 2 shows the results.

[0044]

[Table 1]

[0045]

[Table 2]

Notes of Table 1 and Table 2 MAO: Methylaluminoxane Me: Methyl group no: No detection of hydrogenated substance i-Bu: Isobutyl group

[0047]

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[0048]

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[0049]

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Continuation of the front page (51) Int.Cl. ⁶ Identification number Reference number in the agency FI Technical display location // C07B 61/00 300 C07B 61/00 300

Claims (10)

[Claims] 1. A method for hydrogenating olefins, which comprises reacting olefins with hydrogen in the presence of a metallocene compound and an organoaluminumoxy compound. 2. The method according to claim 1, wherein the metallocene compound is a zirconocene compound. 3. The method according to claim 1 or 2, wherein the organoaluminum oxy compound is methylaluminoxane. 4. The method according to claim 1, wherein the olefins are cycloolefins. 5. The method according to claim 4, wherein the cycloolefins are monoenes or dienes. 6. Hydrogenation of olefins, characterized in that an alkane is obtained by reacting an olefin with hydrogen in the presence of a zirconocene compound having an alkyl-substituted cyclopentadienyl group as a ligand and methylaluminoxane. Method. 7. A method for hydrogenating olefins, which comprises reacting an olefin with hydrogen in the presence of a zirconocene compound having an ethylenebisindenyl group as a ligand and methylaluminoxane to obtain an alkane. 8. An olefin which is obtained by reacting an olefin with hydrogen in the presence of a zirconocene compound having a dialkylmethylene (cyclopentadienyl-fluorenyl) group as a ligand and methylaluminoxane to obtain an alkane. Method of hydrogenation. 9. An alkane is obtained by reacting an olefin with hydrogen in the presence of a zirconocene compound having a dialkylsilylenebis (phenylindenyl) group as a ligand and methylaluminoxane. Hydrogenation method. 10. An alkane is obtained by reacting an olefin with hydrogen in the presence of a zirconocene compound having a dialkylsilylenebis (phenanthrenylindenyl) group as a ligand and methylaluminoxane. Method for hydrogenating olefins.