Derivative of bicyclo [2.2.1] heptane, method for its production, and fluid for traction drive

Abstract

Derivatives of bicyclo[2.2.1]heptane in the invention have a high traction coefficient under high temperature and an excellent viscosity characteristic under low temperature and are useful for the fluid for a traction drive, and a method in the invention produces such derivatives economically and efficiently.

What is claimed is:  
     
         1 . Exo-2-methyl-exo-3-methyl-endo-2-[(endo-2-methylbicyclo[2.2.1]hepto-exo-3-yl)methyl]bicycle[2.2.1]heptane, Exo-2-methyl-exo-3-methyl-endo-2-[(endo-3-methylbicyclo[2.2.1]hepto-exo-2-yl)methyl] bicyclo[2.2.1]heptane, endo-2-methyl-exo-3-methyl-exo-2-[(exo-3-methylbicyclo-[2.2.1]hepto-exo-2-yl)methyl]bicyclo[2.2.1]heptane, endo-2-methyl-exo-3-methl-exo-2-[(exo-2-methylbicyclo[2.2.1]hepto-exo-3-yl)methyl] bicyclo[2.2.1]heptane, endo-2-methyl-exo-3-methyl-exo-2-[(endo-3-methylbicyclo[2.2.1]hepto-endo-2-yl)methyl]bicyclo[2.2.1]heptane, or endo-2-methyl-exo-3-methyl-exo-2-[(endo-2-methylbicyclo[2.2.1]hepto-endo-3-yl) methyl]bicyclo[2.2.1]heptane.  
     
     
         2 . Exo-2-methyl-exo-3-methyl-endo-2-[(endo-3-methylbicyclo[2.2.1]hepto-exo-2-yl)methyl]bicyclo[2.2.1]heptane.  
     
     
         3 . Exo-2-methyl-exo-3-methyl-endo-2-[(endo-2-methylbicyclo[2.2.1]hepto-exo-3-yl)methyl]bicyclo[2.2.1]heptane  
     
     
         4 . Endo-2-methyl-exo-3-methyl-exo-2-[(exo-3-methylbicyxclo[2.2.1]hepto-exo-2-yl)methyl]bicyclo[2.2.1]heptane.  
     
     
         5 . Endo-2-methyl-exo-3-methyl-exo-2-[(exo-2-methylbicyclo[2.2.1]hepto-exo-3-yl)methyl]bicyclo[2.2.1]heptane  
     
     
         6 . Endo-2-methyl-exo-3-methyl-exo-2-[(endo-3-methylbicyclo[2.2.1]hepto-endo-2-yl)methyl]bicyclo[2.2.1]heptane.  
     
     
         7 . Endo-2-methyl-exo-3-methyl-exo-2-[(endo-2-methylbicyclo[2.2.1]hepto-endo-3-yl)methyl]bicyclo[2.2.1]heptane.  
     
     
         8 . A mixture of exo-2-methyl-exo-3-methyl-endo-2-[(endo-3-methylbicyclo[2.2.1]hepto-exo-2-yl)methyl]bicyclo[2.2.1]heptane and exo-2-methyl-exo-3-methyl-endo-2-[(endo-2-methylbicyclo[2.2.1]hepto-exo-3-yl) methyl]bicyclo[2.2.1]heptane.  
     
     
         9 . A mixture of endo-2-methyl-exo-3-methyl-exo-2-[(exo-3-methylbicyclo[2.2.1]hepto-exo-2-yl)methyl]bicyclo[2.2.1]heptane and endo-2-methyl-exo-3-methyl-exo-2-[(exo-2-methylbicyclo[2.2.1]hepto-exo-3-yl) methyl]bicyclo[2.2.1]heptane.  
     
     
         10 . A mixture of endo-2-methyl-exo-3-methyl-exo-2-[(endo-3-methylbicyclo[2.2.1]hepto-endo-2-yl)methyl]bicyclo[2.2.1]heptane and endo-2-methyl-exo-3-methyl-exo-2-[(endo-2-methylbicyclo[2.2.1]hepto-endo-3-yl) methyl]bicyclo[2.2.1]heptane.  
     
     
         11 . A method for preparing a bicyclo[2.2.1]heptane derivative represented by the following formula (IV)  
       
         
           
           
               
               
           
         
       
       (In the formula, m represents 2 or 3 and n represents 1 or 2.)  
       and characterized by dimerization of a methylene- and methyl-substitutedbicyclo[2.2.1l]heptane ring compound and/or a methyl-substituted bicyclo[2.2.1]heptene ring compound under the presence of an acid catalyst at 60° C. or lower temperature and hydrogenating the produced dimer under the presence of a catalyst for hydrogenation at 200-300° C.  
     
     
         12 . A method for preparing a bicyclo[2.2.1]heptane derivative according to  claim 11 , wherein a methylene- and methyl-substituted bicyclo[2.2.1]heptane ring compound is 2-methylene-3-methylbicyclo[2.2.1]heptane and/or 3-methylene-2-methylbicyclo[2.2.1]heptane.  
     
     
         13 . A method for preparing a bicyclo[2.2.1]heptane derivative according to  claim 8 , wherein a methyl-substituted bicyclo[2.2.1]heptene ring compound is 2,3-dimethylbicyclo[2.2.1]hepto-2-ene.  
     
     
         14 . A method for preparing the bicyclo[2.2.1]heptane derivative according to  claim 1 , wherein an acid catalyst is a Lewis acid.  
     
     
         15 . A method for preparing a bicyclo[2.2.1]heptane derivative according to  claim 11 , wherein the catalyst for hydrogenation is a nickel catalyst.  
     
     
         16 . A fluid for a traction drive, characterized by consisting of a synthetic oil having physical properties. 
 (1) Molecular weight: 210 or heavier.    (2) Kinematic viscosity at 40° C.: 10-25 mm 2 /s    (3) Viscosity index: 60 or higher    (4) Pour point: −40° C. or lower    (5) Density at 20° C.: 0.93 g/cm 3  or higher    (6) Traction coefficient at 140° C.: 90% or higher of the coefficient of 2,4-dicyclohexyl-2-methylpentane    
     
     
         17 . A fluid for a traction drive according to  claim 16 , characterized by a hydrogenated dimer of at least one alicyclic compound selected from bicyclo[2.2.1]heptane ring compounds, bicyclo[3.2.1]octane ring compounds, bicyclo[3.3.0]octane ring compounds, and bicyclo[2.2.2]octane ring compounds.  
     
     
         18 . A fluid for a traction drive according to  claim 16 , wherein a synthetic oil is a compound represented by the following general formula (VIII).  
       
         
           
           
               
               
           
         
       
       (In the formula, both R 1  and R2 represent hydrogen atoms or alkyl groups with carbon numbers of 1-3, R3 represents a methylene group, an ethylene group, or a trimethylene group that may be substituted by a methyl group or an ethyl group in a side chain, r represents 0 or 1, and both p and q represent integral numbers of 1-3.)  
     
     
         19 . A fluid for a traction drive consisted of a derivative of bicyclo[2.2.1]heptane represented by the following formula (VII).  
       
         
           
           
               
               
           
         
       
       (In the formula, m represents 2 or 3 and n represents 1 or 2.)  
     
     
         20 . A fluid for a traction drive consisted of at least one compound selected from the group of compounds according to  claim 1.