JP2001247492A - Bicyclo[2.2.1]heptane derivative and method for producing the same and fluid for traction drive - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new compound high in coefficient of traction at high temperatures, excellent in low-temperature viscosity characteristics, therefore useful as a fluid for traction drive. SOLUTION: This new compound is at least one bicyclo[2.2.1]heptane derivative selected from compounds each having a specific three-dimensional structure such as exo-2-methyl-exo-3-methyl-endo-2-[(endo-3-methylbicyclo[2.2.1]hept-exo-2- yl)methyl]bicyclo [2.2.1]heptane.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel bicyclo [2.2.1] heptane derivative and a method for producing the same, and a traction drive fluid containing the bicyclo [2.2.1] heptane derivative. More specifically, a novel bicyclo [2.2.1] heptane derivative which has a high traction coefficient at a high temperature and an excellent low-temperature viscosity property and is useful as a traction drive fluid, and such a bicyclo [2.2.1] The present invention relates to an economical and efficient method for producing a heptane derivative, and particularly to a traction drive fluid having a high traction coefficient at high temperatures and an excellent low-temperature viscosity characteristic.

[0002]

2. Description of the Related Art Traction drive fluid is used as a drive lubricant of a traction drive device used for continuously variable power transmission in automobiles and various industrial machines. The traction coefficient required for this traction drive fluid is generally said to depend on the size of the traction drive device, and as the development of small and lightweight traction drive devices progresses, traction drive devices with higher traction coefficients are used. Fluid is needed.

For example, a traction type CVT for an automobile
(Continuously variable transmission) has a large torque transmission capacity and is small in size, so the traction drive fluid used for it has a high temperature (for example, 1
It is essential that the traction coefficient of the traction oil at around 40 ° C.) is sufficiently higher than the designed value of CVT.

[0004] A traction drive fluid is required to have various performances in addition to a high traction coefficient. For example, in order to maintain excellent startability even in a cold region, even at -40 ° C, for example, 200,000 mPa
-It is required to have a low viscosity of s or less. On the other hand, even when used at a high temperature, volatilization of the base oil must be suppressed and a sufficient oil film must be maintained.

[0005] Among the above-mentioned performances, in particular, increasing the traction coefficient at high temperatures and decreasing the viscosity at low temperatures are contradictory performances, and although development of a traction oil satisfying both has been desired, , Its development was very difficult. Against this background, the present inventors have conducted intensive research and found a group of compounds having an excellent high-temperature traction coefficient (Japanese Patent Publication No. 7-103387). However, the low-temperature viscosity characteristics are not always sufficient. Was.

[0006]

SUMMARY OF THE INVENTION The present invention has been made from the above viewpoint, and has a high traction coefficient at a high temperature.
It is an object of the present invention to provide a novel compound which is excellent in low-temperature viscosity characteristics and is useful as a traction drive fluid, and a method for economically and efficiently producing such a compound.

Another object of the present invention is to provide a traction drive fluid having a high traction coefficient at a high temperature and excellent low-temperature viscosity characteristics.

[0008]

Means for Solving the Problems The present inventors have conducted intensive studies and as a result, have found that bicyclo [2.2.
1] The fact that the heptane derivative exhibits particularly excellent performance as a traction drive fluid, and that the above-mentioned bicyclo [2.2.1] heptane derivative can be produced economically and efficiently by using a specific raw material and a specific reaction condition. I found it.

The present inventors have further found that a synthetic oil containing the above bicyclo [2.2.1] heptane derivative and having specific properties exhibits particularly excellent performance as a traction drive fluid.

The present invention has been completed based on the above findings. That is, the gist of the present invention is as follows. [1] exo-2-methyl-exo-3-methyl-en
do-2-[(endo-3-methylbicyclo [2.
2.1] Hept-exo-2-yl) methyl] bicyclo [2.2.1] heptane, exo-2-methyl-exo
-3-Methyl-endo-2-[(endo-2-methylbicyclo [2.2.1] hept-exo-3-yl)
Methyl] bicyclo [2.2.1] heptane, endo-
2-methyl-exo-3-methyl-exo-2-[(e
xo-3-methylbicyclo [2.2.1] hept-ex
o-2-yl) methyl] bicyclo [2.2.1] heptane, endo-2-methyl-exo-3-methyl-ex
o-2-[(exo-2-methylbicyclo [2.2.
1] Hept-exo-3-yl) methyl] bicyclo [2.2.1] heptane, endo-2-methyl-ex
o-3-methyl-exo-2-[(endo-3-methylbicyclo [2.2.1] hept-endo-2-yl) methyl] bicyclo [2.2.1] heptane, and e
ndo-2-methyl-exo-3-methyl-exo-2
-[(Endo-2-methylbicyclo [2.2.1] hept-endo-3-yl) methyl] bicyclo [2.
2.1] One or more bicyclo [2.2.1] heptane derivatives selected from heptane. [2] exo-2-methyl-exo-3-methyl-en
do-2-[(endo-3-methylbicyclo [2.
2.1] Hept-exo-2-yl) methyl] bicyclo [2.2.1] heptane and exo-2-methyl-ex
Bicyclo consisting of a mixture with o-3-methyl-endo-2-[(endo-2-methylbicyclo [2.2.1] hept-exo-3-yl) methyl] bicyclo [2.2.1] heptane [2.2.1] Heptane derivative. [3] endo-2-methyl-exo-3-methyl-e
xo-2-[(exo-3-methylbicyclo [2.2.
1] hept-exo-2-yl) methyl] bicyclo [2.2.1] heptane and endo-2-methyl-e
xo-3-methyl-exo-2-[(exo-2-methylbicyclo [2.2.1] hept-exo-3-yl)
Bicyclo [2.2.1] heptane derivative comprising a mixture with [methyl] bicyclo [2.2.1] heptane. [4] endo-2-methyl-exo-3-methyl-e
xo-2-[(endo-3-methylbicyclo [2.
2.1] Hept-endo-2-yl) methyl] bicyclo [2.2.1] heptane and endo-2-methyl-
exo-3-methyl-exo-2-[(endo-2-
Methylbicyclo [2.2.1] hept-endo-3-
Yl) Bicyclo [2.2.1] heptane derivative comprising a mixture with methyl] bicyclo [2.2.1] heptane. [5] exo-2-methyl-exo-3-methyl-en
do-2-[(endo-3-methylbicyclo [2.
2.1] Hept-exo-2-yl) methyl] bicyclo [2.2.1] heptane, exo-2-methyl-exo
-3-Methyl-endo-2-[(endo-2-methylbicyclo [2.2.1] hept-exo-3-yl)
Methyl] bicyclo [2.2.1] heptane, endo-
2-methyl-exo-3-methyl-exo-2-[(e
xo-3-methylbicyclo [2.2.1] hept-ex
o-2-yl) methyl] bicyclo [2.2.1] heptane and endo-2-methyl-exo-3-methyl-e
xo-2-[(exo-2-methylbicyclo [2.2.
1] A bicyclo [2.2.1] heptane derivative comprising a mixture of hept-exo-3-yl) methyl] bicyclo [2.2.1] heptane. [6] endo-2-methyl-exo-3-methyl-e
xo-2-[(exo-3-methylbicyclo [2.2.
1] Hept-exo-2-yl) methyl] bicyclo [2.2.1] heptane, endo-2-methyl-ex
o-3-methyl-exo-2-[(exo-2-methylbicyclo [2.2.1] hept-exo-3-yl) methyl] bicyclo [2.2.1] heptane, endo-2
-Methyl-exo-3-methyl-exo-2-[(en
do-3-methylbicyclo [2.2.1] hept-en
do-2-yl) methyl] bicyclo [2.2.1] heptane and endo-2-methyl-exo-3-methyl-exo-2-[(endo-2-methylbicyclo [2.2.1] Hept-endo-3-yl) methyl]
A bicyclo [2.2.1] heptane derivative comprising a mixture of bicyclo [2.2.1] heptane. [7] 2-methylene-3-methylbicyclo [2.2.
1] One or more bicyclo selected from heptane, 3-methylene-2-methylbicyclo [2.2.1] heptane and 2,3-dimethylbicyclo [2.2.1] hept-2-ene [2.2.1] the dimerization of a heptane ring compound at 60 ° C. or lower in the presence of an acid catalyst, and the resulting dimer is hydrogenated at 220 to 280 ° C. in the presence of a hydrogenation catalyst. Bicyclo [2.2.1] of [5]
A method for producing a heptane derivative. [8] 2-Methylene-3-methylbicyclo [2.2.
1] One or more bicyclo selected from heptane, 3-methylene-2-methylbicyclo [2.2.1] heptane and 2,3-dimethylbicyclo [2.2.1] hept-2-ene [2.2.1] the dimerization of a heptane ring compound at 60 ° C. or lower in the presence of an acid catalyst, and hydrogenating the resulting dimer at 170 to 220 ° C. in the presence of a hydrogenation catalyst. Bicyclo [2.2.1] of [6]
A method for producing a heptane derivative.

[9] The above-mentioned [7] or [8], wherein the acid catalyst is a Lewis acid.
2. The method for producing a bicyclo [2.2.1] heptane derivative according to item 1. [10] The bicyclo [2.2.1] heptane derivative according to any of the above [1] to [6] or the above [7] to [7]

A traction drive fluid comprising a bicyclo [2.2.1] heptane derivative obtained by the production method according to any one of [9] and a synthetic oil having the following physical properties as a base oil. (1) Molecular weight: 210 or more (2) Kinematic viscosity at 40 ° C .: 10 to 25 mm ² / s (3) Viscosity index: 60 or more (4) Pour point: −40 ° C. or less (5) Low temperature viscosity at −40 ° C .: 150,000 mP
a · s or less (6) Density at 20 ° C .: 0.93 g / cm ³ or more (7) Traction coefficient at 140 ° C .: 90% or more of the value of 2,4-dicyclohexyl-2-methylpentane

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The bicyclo [2.
2.1] A heptane derivative, a method for producing the derivative, and a traction drive fluid will be described in detail. 1. Bicyclo [2.2.1] heptane derivative The present invention relates to a bicyclo [2.2.1] heptane having a specific structure.
Heptane derivative, specifically, exo-2-methyl-exo-3-methyl-endo-2-[(endo-
3-methylbicyclo [2.2.1] hept-exo-2
-Yl) methyl] bicyclo [2.2.1] heptane, e
xo-2-methyl-exo-3-methyl-endo-2
-[(Endo-2-methylbicyclo [2.2.1] hept-exo-3-yl) methyl] bicyclo [2.2.
1] Heptane, endo-2-methyl-exo-3-methyl-exo-2-[(exo-3-methylbicyclo [2.2.1] hept-exo-2-yl) methyl] bicyclo [2.2 .1] heptane, endo-2-methyl-exo-3-methyl-exo-2-[(exo-2-
Methylbicyclo [2.2.1] hept-exo-3-yl) methyl] bicyclo [2.2.1] heptane, end
o-2-methyl-exo-3-methyl-exo-2-
[(Endo-3-methylbicyclo [2.2.1] hept-endo-2-yl) methyl] bicyclo [2.2.
1] heptane, and endo-2-methyl-exo-3
-Methyl-exo-2-[(endo-2-methylbicyclo [2.2.1] hept-endo-3-yl) methyl] bicyclo [2.2.1] heptane Bicyclo [2.2.1] heptane derivative. These compounds are represented by the following (I) to (VI), respectively.
Is represented by the following chemical structural formula.

[0012]

Embedded image

These bicyclo [2.2.1] heptane derivatives have a high traction coefficient at high temperatures and excellent low-temperature viscosity characteristics, and are used worldwide for traction drive fluids (from traction to cold regions to high temperature regions). CVT
Lubricant). Also,
It is an extremely valuable compound for further reducing the traction CVT.

These compounds are all contained in a bicyclo [2.2.1] heptane derivative represented by the following general formula (VII), and are described below. ] In a method for producing a heptane derivative,
It is manufactured at the same time or in a similar manner by partially changing the manufacturing conditions. The chemical structures of these compounds are represented by mass chromatograms, ¹ H-NMR, ¹³ C-NM
It is specified by analysis of each spectrogram of R, ¹³ C- ¹³ C-NMR and ¹ H- ¹³ C-NMR.

These compounds may be used alone or in a mixture of two or more. As a mixture of these compounds, for example, as those which are easily produced and obtained as a mixture because the properties are very similar,
Mixtures of two compounds each of formulas (I) and (II), formulas (III) and (IV), and formulas (V) and (VI). In addition, examples of those that can be efficiently obtained under one production condition include, for example, four kinds of mixtures of the compounds of formulas (I) to (IV) and formulas (III) to (VI). The same applies to the mixtures of the formulas (I) to (VI). The mixing ratio of each of the above mixtures is arbitrary, and any mixture ratio can be used.

2. Production method of bicyclo [2.2.1] heptane derivative The present invention provides 2-methylene-3-methylbicyclo [2.2.1] heptane and 3-methylene-2-methylbicyclo [2.2. 1] One or more bicyclo [2.2.1] heptane ring compounds selected from heptane and 2,3-dimethylbicyclo [2.2.1] hept-2-ene are reacted with an acid catalyst. The resulting dimer is hydrogenated at 170 to 280 ° C. in the presence of a hydrogenation catalyst, whereby the bicyclo represented by the above formulas (I) to (VI) [2. 2.1] A method for producing a bicyclo [2.2.1] heptane derivative mainly containing a mixture of heptane derivatives.

In the present invention, the isomerization reaction is controlled by further selecting the above-mentioned production conditions, and the bicyclo [2.2.1] heptane derivative represented by the formulas (I) to (VI) is obtained. Can be obtained in any proportion. For example, after producing a dimer by the above-mentioned method, by hydrogenating at 220 to 280 ° C. in the presence of a hydrogenation catalyst, the bicyclo [2.
2.1] A bicyclo [2.2.1] heptane derivative containing a mixture of heptane derivatives as a main component can be efficiently produced.

By hydrogenating at 170 to 220 ° C. in the presence of a hydrogenation catalyst by the above method, the above formula (II)
Bicyclo [2.2.] Containing a mixture of the bicyclo [2.2.1] heptane derivatives represented by (I) to (VI) as a main component.
1] A heptane derivative can be produced efficiently.

Here, 2-methylene-3 used as a raw material
-Methylbicyclo [2.2.1] heptane has exo
-2-methyl-3-methylenebicyclo [2.2.1] heptane and endo-2-methyl-3-methylenebicyclo [2.2.1] heptane are present, and 3-methyl-methylenebicyclo [2.2.1] heptane is also present.
2-methylenebicyclo [2.2.1] heptane is ex
o-3-methyl-2-methylenebicyclo [2.2.1]
Heptane and endo-3-methyl-2-methylenebicyclo [2.2.1] heptane are present and may be any of these.

Further, 2-methylene-3-methylbicyclo [2.2.1] heptane, 3-methylene-2-methylbicyclo [2.2.1] heptane and 2,3-dimethylbicyclo [2.2] .1] When two or more of the starting compounds of hept-2-ene are used as a mixture, the mixing ratio is not particularly limited, and any mixing ratio can be used. Among them, it is preferable to use a raw material compound in which these three are mixed.

In the present invention, first, the starting compound is dimerized in the presence of an acidic catalyst. Examples of the acidic catalyst include mineral acids such as hydrofluoric acid and polyphosphoric acid, organic acids such as triflic acid, aluminum chloride, ferric chloride, tin tetrachloride, titanium tetrachloride, boron trifluoride, and boron trifluoride complex. , Boron tribromide, aluminum bromide, gallium chloride, gallium bromide, and the like; and organic aluminum compounds such as triethylaluminum, diethylaluminum chloride, and ethylaluminum dichloride.

Among these catalysts, Lewis acid catalysts such as boron trifluoride, boron trifluoride complex, tin tetrachloride, titanium tetrachloride, and aluminum chloride are preferred because they can be dimerized at a lower temperature. preferable. Among them, boron trifluoride diethyl ether complex, boron trifluoride water complex,
Boron trifluoride complexes such as boron trifluoride alcohol complexes are more preferred.

The use amount of these catalysts is not particularly limited, but is usually 0.1 to 10 based on the starting olefin.
0 mass%, preferably in the range of 0.5 to 20 mass%. In the dimerization reaction, a solvent is not necessarily required, but it may be used for handling the raw material olefin or catalyst during the reaction or for controlling the progress of the reaction. Examples of such a solvent include various hydrocarbons such as various pentanes, various hexanes, various octanes, various nonanes, various decane, cyclopentane, cyclohexane, methylcyclohexane, and the like.
Alicyclic hydrocarbons such as decalin, ether compounds such as diethyl ether and tetrahydrofuran, halogen-containing compounds such as methylene chloride and dichloroethane, nitromethane,
Examples thereof include nitro compounds such as nitrobenzene.

This dimerization reaction is usually performed at a reaction temperature of 60 ° C. or lower, preferably 40 ° C. or lower. Reaction temperature 60
If the temperature exceeds ℃, the dimer which is a reaction product may be sterically isomerized, and it is preferable to perform the dimerization at a lower temperature in order to suppress the isomerization reaction. On the other hand, the dimerization lower limit temperature is not particularly limited as long as the reaction proceeds, but is preferably -70 ° C or higher, more preferably -30 ° C or higher, from the economical viewpoint.

The reaction pressure for the dimerization reaction is appropriately set depending on the reaction temperature, the type of catalyst, the presence or absence of a solvent or the type used, but normal pressure is usually preferable. The reaction time is usually preferably in the range of 0.5 to 10 hours. In the present invention, the dimer thus obtained is hydrogenated usually in the presence of a hydrogenation catalyst.

As the hydrogenation catalyst, a catalyst having a metal component supported on a carrier can be used. Specifically, an inorganic oxide carrier such as diatomaceous earth, alumina, silica-alumina, or activated carbon supports a metal of Group 8 to 10 of the periodic table, for example, a metal such as nickel, ruthenium, palladium, platinum, rhodium, and iridium. Hydrogenation catalyst. Among these, from the viewpoint of product selectivity,
Nickel-based catalysts such as nickel / diatomaceous earth and nickel / silica alumina are preferred. If necessary, a solid acid such as zeolite, silica alumina or activated clay may be used as a co-catalyst for the hydrogenation reaction.

In particular, in producing the bicyclo [2.2.1] heptane derivative of the present invention, it is preferable to use a nickel / diatomaceous earth catalyst as the hydrogenation catalyst. The use ratio of this catalyst is 0.1 to 10 with respect to the dimerization product.
It is used in an amount of 0% by mass, preferably 1 to 20% by mass.

This hydrogenation reaction proceeds in the absence of a solvent as in the case of the above-mentioned dimerization reaction, but it is preferable to use a solvent, and preferable solvents include various pentanes, various hexanes, various octanes, and various nonanes. And saturated hydrocarbons such as various decane and alicyclic hydrocarbons such as cyclopentane, cyclohexane, methylcyclohexane and decalin.

As described above, the reaction temperature of the hydrogenation reaction is preferably from 170 to 280 ° C, more preferably from 180 to 270 ° C. When the reaction temperature is lower than 170 ° C., the isomerization reaction does not sufficiently occur, the viscosity index of the product is lowered, and the desired product may not be obtained.
If the temperature is higher than 0 ° C., a decomposition reaction starts to occur, and the yield of a product may decrease. Here, the reaction temperature is set to 220 to 280.
If the hydrogenation reaction is carried out at a temperature of 230 ° C., more preferably at 230 to 270 ° C., the compounds having the chemical structures represented by formulas (I) to (IV) can be produced in good yield, and the reaction temperature is preferably 170 to 220 ° C. If a hydrogenation reaction is carried out in the range of 180 to 220 ° C., compounds having the chemical structures represented by the formulas (III) to (VI) can be produced in good yield.

The reaction pressure of the hydrogenation reaction is as follows:
Although there is no particular limitation, the reaction is performed in a range from normal pressure to 20 MPa (G), preferably from normal pressure to 10 MPa (G). The hydrogen pressure is preferably 0.5 to 9 MPa (G), more preferably 1 to 8 MPa (G). The reaction time is usually 1 to 10 hours. The bicyclo [2.2.1] heptane derivative represented by the formulas (I) to (VI) thus obtained has a high traction coefficient at a high temperature, excellent low-temperature viscosity characteristics, and a low-temperature region. Traction drive C worldwide
It can be used as VT oil.

3. Traction drive fluid of the present invention
The traction drive fluid is the bicyclo
[2.2.1] heptane derivative, that is, a compound of formula (I)
Bicyclo having the steric structure represented by (VI) [2.
2.1] A compound containing at least one heptane derivative
It is a fluid for traction drive. Furthermore, the present invention
The fluid for traction drive includes the following (1) to (7)
It is a synthetic oil having physical properties. (1) The number average molecular weight of the synthetic oil is 210 or more, preferably
Is 215 to 290. With number average molecular weight less than 210
May cause a large amount of volatilization when used at high temperatures.
Is not preferred. (2) The kinematic viscosity at 40 ° C. of the synthetic oil is 10 to 25 m
m^Two/ S, preferably 12 to 24 mm^Two/ S. 4
Kinematic viscosity at 0 ° C is 10mm^Two/ S is less than
At high temperatures, the viscosity becomes too low and a sufficient lubricating oil film thickness is obtained.
There is a risk of disappearing. On the other hand, 25mm^Two/ S
And the low temperature viscosity at -40 ° C increases.
Traction drive device is difficult to start when used
Become. (3) The synthetic oil has a viscosity index of 60 or more, preferably 65 or more.
That is all. If the viscosity index is less than 60,
Low-temperature viscosity increases, causing
The traction drive device becomes difficult to start. (4) The pour point of the synthetic oil is −40 ° C. or lower, preferably −
45 ° C. or less. Cold when pour point is higher than -40 ° C
The traction drive will start when
It becomes difficult. (5) Low temperature viscosity at -40 ° C is 150,000 m
Pa · s or less, preferably 130,000 mPa · s or less
Below. Low temperature viscosity at -40 ° C of 150,000
If it exceeds mPa · s, it will cause
The drive unit becomes difficult to start. (6) The density of the synthetic oil at 20 ° C. is 0.93 g / c
m^ThreeAbove, preferably 0.93 to 1.50 g / cm^Three
It is. 0.93 g / cm density at 20 ° C ^ThreeLess than
Lower the traction coefficient at high temperatures.
There is. (7) The traction coefficient of the synthetic oil at 140 ° C.
Of the value of 2,4-dicyclohexyl-2-methylpentane
90% or more, preferably 2,4-dicyclohexyl-2
Not less than the value of methylpentane. At 140 ° C
The fractionation coefficient is 2,4-dicyclohexyl-2-methyl
If it is less than 90% of the value of lupentane,
The torque transmission capacity may not be sufficient.

The compound constituting the synthetic oil of the present invention contains a bicyclo [2.2.1] heptane derivative having a steric structure represented by formulas (I) to (VI). Is not particularly limited as long as it satisfies the physical properties of (1) to (7), but is usually preferably at least 20% by mass, more preferably at least 50% by mass, particularly preferably at least 70% by mass, based on the synthetic oil. .

Compounds other than the bicyclo [2.2.1] heptane derivative having a steric structure represented by the above formulas (I) to (VI), which may constitute the synthetic oil of the present invention, Is, for example, a bicyclo [2.2.1] heptane ring compound, a bicyclo [3.2.1] octane ring compound,
A preferred compound is a dimer hydride of at least one alicyclic compound selected from a bicyclo [3.3.0] octane ring compound and a bicyclo [2.2.2] octane ring compound.

Among these compounds, dimer hydrides of bicyclo [2.2.1] heptane ring compounds represented by the following general formula (VII) (provided that formulas (I) to (VI) (Excluding the bicyclo [2.2.1] heptane derivative represented by This compound has the formula (I) to (V
The bicyclo [2.2.1] heptane derivative represented by the formula (I) is an isomer having a different steric structure, and the bicyclo [2.2.1] heptane derivative represented by the formula (I) to (VI) is During production, it may be obtained as a by-product.

[0035]

Embedded image

(Wherein, R ¹ and R ² each represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R ³ represents a methylene group or an ethylene group which may be substituted with a methyl group or an ethyl group on the side chain. Represents a group or a trimethylene group, n represents 0 or 1, and p and q each represent an integer of 1 to 3.) The hydride represented by the general formula (VII) is obtained by dimerizing an olefin as a raw material. And then hydrogenated and then distilled.

Examples of the olefin as the raw material include bicyclo [2.2.1] hept-2-ene; vinyl-substituted or isopropenyl-substituted bicyclo [2.2.
1] alkenyl-substituted bicyclo [2.2.1] hept-2-ene such as hept-2-ene; alkylidene such as methylene-substituted, ethylidene-substituted or isopropylidene-substituted bicyclo [2.2.1] hept-2-ene Substituted bicyclo [2.2.1] hept-2-ene; alkenyl-substituted bicyclo [2.2.1] heptane such as vinyl-substituted or isopropenyl-substituted bicyclo [2.2.1] heptane; methylene-substituted, ethylidene-substituted or Alkylidene-substituted bicyclo [2.2.1] heptane such as isopropylidene-substituted bicyclo [2.2.1] heptane; bicyclo [3.2.1] octene; vinyl-substituted or isopropylenyl-substituted bicyclo [3.2.1] Alkenyl-substituted bicyclo [3.2.1] octene such as octene; methylene-substituted and ethylidene-substituted Is alkylidene-substituted bicyclo [3.2.1] octene such as isopropylidene-substituted bicyclo [3.2.1] octene; alkenyl-substituted bicyclo [3.2] such as vinyl-substituted or isopropylenyl-substituted bicyclo [3.2.1] octane; 2.1] octane; alkylidene-substituted bicyclo [3.2.1] octane such as methylene-substituted, ethylidene-substituted or isopropylidene-substituted bicyclo [3.2.1] octane; bicyclo [3.
3.0] octene; alkenyl-substituted bicyclo [3.3.0] octene such as vinyl-substituted or isopropenyl-substituted bicyclo [3.3.0] octene; methylene-substituted, ethylidene-substituted or isopropylidene-substituted bicyclo [3.3. 0] alkylidene-substituted bicyclo [3.3.0] octene such as octene; alkenyl-substituted bicyclo [3.3.0] octane such as vinyl-substituted or isopropenyl-substituted bicyclo [3.3.0] octane; methylene-substituted, ethylidene Alkylidene-substituted bicyclo [3.3.0] octane such as substituted or isopropylidene-substituted bicyclo [3.3.0] octane; bicyclo [2.2.2]
Octene; vinyl-substituted or isopropenyl-substituted bicyclo [2.2.2] octene or other alkenyl-substituted bicyclo [2.2.2] octene; methylene-substituted, ethylidene-substituted or isopropylidene-substituted bicyclo [2.2.
2] alkylidene-substituted bicyclo such as octene [2.2.
2] octene; alkenyl-substituted bicyclo [2.2.2] octane such as vinyl-substituted or isopropenyl-substituted bicyclo [2.2.2] octane; methylene-substituted, ethylidene-substituted or isopropylidene-substituted bicyclo [2.
2.2] alkylidene-substituted bicyclo such as octane [2.
2.2] octane.

In particular, in order to obtain a dimeric hydride of the bicyclo [2.2.1] heptane ring compound represented by the general formula (VII), the corresponding starting olefinic ring compound must be Specifically, for example, bicyclo [2.2.1]
Hept-2-ene; 2-methylenebicyclo [2.2.
1] heptane; 2-methylbicyclo [2.2.1] hept-2-ene; 2-methylene-3-methylbicyclo [2.2.1] heptane; 2,3-dimethylbicyclo [2.2.1] ] Hept-2-ene; 2-methylene-7-
Methylbicyclo [2.2.1] heptane; 2,7-dimethylbicyclo [2.2.1] hept-2-ene; 2-methylene-5-methylbicyclo [2.2.1] heptane;
2,5-dimethylbicyclo [2.2.1] hept-2-
Ene; 2-methylene-6-methylbicyclo [2.2.
1] heptane; 2,6-dimethylbicyclo [2.2.
1] Hept-2-ene; 2-methylene-1-methylbicyclo [2.2.1] heptane; 1,2-dimethylbicyclo [2.2.1] hept-2-ene; 2-methylene-4
-Methylbicyclo [2.2.1] heptane; 2,4-dimethylbicyclo [2.2.1] hept-2-ene; 2-
Methylene-3,7-dimethylbicyclo [2.2.1] heptane; 2,3,7-trimethylbicyclo [2.2.
1] Hept-2-ene; 2-methylene-3,6-dimethylbicyclo [2.2.1] heptane; 2-methylene-
3,3-dimethylbicyclo [2.2.1] heptane;
2,3,6-trimethylbicyclo [2.2.1] hept-2-ene; 2-methylene-3-ethylbicyclo [2.
2.1] heptane; and 2-methyl-3-ethylbicyclo [2.2.1] hept-2-ene.

The above-mentioned dimerization means not only dimerization of the same kind of olefin but also co-dimerization of a plurality of different kinds of olefins. The olefin dimerization reaction described above is
Usually, a solvent is added as needed in the presence of a catalyst.
As a catalyst used for this dimerization reaction, an acidic catalyst is usually used. Specific examples of the acid catalyst include those represented by the above formula (I)
To the bicyclo having a steric structure represented by (VI) [2.
2.1] The same ones as used in producing the heptane derivative can be used. Also, the amount of catalyst used,
The same applies to the reaction conditions.

Next, the obtained dimer is hydrogenated in the presence of a hydrogenation catalyst. As the hydrogenation catalyst, the same catalyst as that used in producing the bicyclo [2.2.1] heptane derivative having the stereostructure represented by the above formulas (I) to (VI) may be used. it can. The same applies to the amount of the catalyst used and the use of the solvent in the hydrogenation reaction.

The reaction temperature of the hydrogenation reaction is not particularly limited and is usually 100 to 300 ° C., preferably 200 to 300 ° C.
00 ° C, particularly preferably 220 to 280 ° C. When the reaction temperature is lower than 100 ° C., a compound having an insufficient viscosity index may be generated, and when the reaction temperature is higher than 300 ° C., the product may be decomposed and the yield may be reduced. The reaction pressure for the hydrogenation reaction is the same as the reaction pressure for producing the bicyclo [2.2.1] heptane derivative having the steric structure represented by the formulas (I) to (VI).

The compound of the present invention other than the bicyclo [2.2.1] heptane derivative having a steric structure represented by any of formulas (I) to (VI) further includes any of a cyclohexyl group and a decalyl group in the molecule. And a compound having at least two of these. Representative examples of this compound include, for example, 2,4-dicyclohexyl-2-methylpentane, 2,4-dicyclohexylpentane, 1,3-
Dicyclohexyl-3-methylbutane and the like.

In the present invention, the synthetic oil satisfying the physical properties (1) to (7) is used as the base oil of the traction drive fluid, but does not deviate from the range of the physical properties (1) to (7). As described above, another liquid material may be mixed with the synthetic oil for use. For example, a low-viscosity base oil such as poly-α-olefin oil (PAO) or diester is mixed so as not to impair the high-temperature traction coefficient, or an alicyclic compound-based traction base oil or dicyclopentadiene is used so as not to impair the low-temperature viscosity. A high temperature traction coefficient improving base such as a system hydrogenated petroleum resin can be mixed. The amount of the liquid material to be mixed is preferably 15% by mass or less based on the final synthetic oil.

Further, if necessary, an antioxidant, a rust inhibitor, a detergent / dispersant, a pour point depressant, a viscosity index improver, an extreme pressure agent, an antiwear agent, Various additives such as an oil agent, an antifoaming agent, and a corrosion inhibitor can be blended in appropriate amounts.

[0045]

[Example 1]

(Preparation of Raw Olefin) In a 2-liter stainless steel autoclave, 561 g (8 mol) of crotonaldehyde and 352 g (2.67 mol) of dicyclopentadiene were charged and reacted by stirring at 170 ° C. for 3 hours.
After the reaction solution was cooled to room temperature, 18 g of Raney nickel catalyst (manufactured by Kawaken Fine Chemical Co .; M-300T) was added, and hydrogenation was carried out at a hydrogen pressure of 0.9 MPa (G) and a reaction temperature of 150 ° C. for 4 hours. After cooling, the catalyst was filtered off, and the filtrate was distilled under reduced pressure to give 105 ° C./2.67 kPa (20 mm
Hg) 565 g of a fraction were obtained. This fraction was analyzed by mass spectrum and nuclear magnetic resonance spectrum. As a result, this fraction was found to be 2-hydroxymethyl-3-methylbicyclo [2.2.
1] heptane and 3-hydroxymethyl-2-methylbicyclo [2.2.1] heptane.

Next, 20 g of γ-alumina (N612N, manufactured by Nikki Chemical Co., Ltd.) was placed in a flow-type atmospheric pressure reaction tube made of quartz glass having an outer diameter of 20 mm and a length of 500 mm.
The dehydration reaction was carried out at 1.1 ° C. and a weight hourly space velocity (WHSV) of 1.1 hr ^-1 to give 2-methylene-3-methylbicyclo [2.2.
1] Heptane and 55% by mass of 3-methylene-2-methylbicyclo [2.2.1] heptane and 30% by mass of 2,3-dimethylbicyclo [2.2.1] hept-2-ene
2-hydroxymethyl-3-methylbicyclo [2.2.1] heptane and 3-hydroxymethyl-2-
490 g of a dehydration reaction product of methylbicyclo [2.2.1] heptane was obtained.

(Preparation of dimer hydride) Boron trifluoride diethyl ether complex 8 was placed in a 1-liter four-necked flask.
g, and 400 g of the olefin compound obtained above,
The dimerization reaction was performed at 20 ° C. for 4 hours while stirring using a mechanical stirrer. The reaction mixture is diluted with dilute NaO
After washing with an aqueous H solution and saturated saline, 12 g of a nickel / diatomaceous earth catalyst for hydrogenation [N-113, manufactured by JGC Chemicals Co., Ltd.] was added to a 1 liter autoclave, and the hydrogen pressure was 3 MPa.
(G) A hydrogenation reaction was performed under the conditions of a reaction temperature of 250 ° C. and a reaction time of 6 hours. After completion of the reaction, the catalyst was removed by filtration, and the filtrate was distilled under reduced pressure to obtain 240 g of the desired dimer hydride. Table 1 shows the general properties of the dimer hydride and the measurement results of the traction coefficient.

The dimer hydride was subjected to precision distillation separation twice using a rotary band type distillation apparatus having 120 theoretical plates to obtain 149.2 ° C./0.67 kPa (5 mmHg).
1 g of the component (A component) was obtained. When the A component was analyzed,
Exo-2-methyl-exo-3-methyl-endo-2-[(endo-3-methylbicyclo [2.2.1] hept-exo-2-yl) methyl] having a purity of 98% by mass
Bicyclo [2.2.1] heptane and exo-2-methyl-exo-3-methyl-endo-2-[(endo-
2-methylbicyclo [2.2.1] hept-exo-3
-Yl) methyl] bicyclo [2.2.1] heptane. The structural formula of the component A is represented by the formula (I),
This is as shown in (II).

The mass chromatogram, ¹ H-NMR, ¹³ C-NMR, ¹³ C- ¹³ C-NM used in this structural analysis
R and ¹ H- ¹³ C-NMR spectrograms are shown in FIGS.
It is shown in FIG. Separate by precision distillation in the same manner as described above, 1 g of 133.6 ° C./0.27 kPa (2 mmHg) component (B component) was obtained. When the component B was analyzed, it was found that endo-2-methyl-exo-3-methyl-exo-2-[(exo-3-methylbicyclo [2.2.1] hept-exo-2-yl having a purity of 99% by mass. ) Methyl] bicyclo [2.2.1] heptane and endo-2-methyl-exo-3-methyl-exo-2-[(exo-2-
Methylbicyclo [2.2.1] hept-exo-3-yl) methyl] bicyclo [2.2.1] heptane. The structural formula of the B component is the above formula (III), (IV)
As shown in FIG.

The mass chromatogram, ¹ H-NMR, ¹³ C-NMR, and ¹³ C- ¹³ C-NM used in this structural analysis were used.
Each spectrogram of R, ¹ H- ¹³ C-NMR is shown in FIG.
It is shown in FIG. The dimer hydride prepared in Example 1 was analyzed by gas chromatography to find that the A component 20
% By mass, and 60% by mass of the B component.

Example 2 Table 1 shows the measurement results of the general properties and the traction coefficient of the fraction containing 65% by mass of the component A and 25% by mass of the component B obtained by the precision distillation of Example 1.

Example 3 In Example 1, the hydrogenation reaction was carried out at 250 ° C. for 6 hours.
240 g of dimeric hydride was obtained in the same manner except that the reaction was carried out for 2 hours. This dimer hydride is converted into 1 theoretical plate.
By performing precision distillation separation twice with a 20-stage rotary band type distillation apparatus, 1 g of the above-mentioned B component was obtained.

Further, by precision distillation separation in the same manner as described above, 138.6 ° C./0.27 kPa (2 mmHg)
1 g of the component (C component) was obtained. When the C component was analyzed,
Endo-2-methyl-exo-3 having a purity of 100% by mass
-Methyl-exo-2-[(endo-3-methylbicyclo [2.2.1] hept-endo-2-yl) methyl] bicyclo [2.2.1] heptane and endo-2-
Methyl-exo-3-methyl-exo-2-[(end
o-2-methylbicyclo [2.2.1] hept-end
o-3-yl) methyl] bicyclo [2.2.1] heptane. The structural formula of the C component is as shown in the above formulas (V) and (VI).

The mass chromatogram, ¹ H-NMR, ¹³ C-NMR, and ¹³ C- ¹³ C-NM used in this structural analysis were used.
FIG. 11 shows each spectrogram of R, ¹ H- ¹³ C-NMR.
~ 15. The dimer hydride prepared in Example 3 was analyzed by gas chromatography to find that the B component 4
It contained 5% by mass and 45% by mass of the C component.

Example 4 Table 1 shows the measurement results of the general properties and the traction coefficient of the fraction containing 88% by mass of the component B and 10% by mass of the component C obtained by the precise distillation of Example 3. .

Example 5 In Example 1, the catalyst for the dimerization reaction was changed to a boron trifluoride diethyl ether complex (8 g).
Was used in the same manner except that 32 g of tin tetrachloride was used, to obtain 140 g of a dimeric hydride. As a result of analyzing the dimer hydride by gas chromatography, it contained 20% by mass of the component A and 60% by mass of the component B. Table 1 shows the measurement results of the general properties and the traction coefficient.

Comparative Example 1 The procedure of Example 1 was repeated, except that the hydrogenation reaction was carried out at 250 ° C. for 6 hours.
240 g of dimeric hydride was obtained in the same manner except that the reaction was carried out for an hour. This dimer hydride is represented by mass spectrum,
As a result of analysis by nuclear magnetic resonance spectrum, it was found to be a bicyclo [2.2.1] heptane derivative represented by the above formula (VII). Table 1 shows the measurement results of the general properties and the traction coefficient.

Comparative Example 2 350.5 g of crotonaldehyde (5
Mol) and 198.3 g of dicyclopentadiene (1.5
Mol), and reacted by stirring at 170 ° C. for 2 hours. After cooling the reaction solution to room temperature, 5% ruthenium-
22 g of a carbon catalyst (NE Chemcat Corporation)
Hydrogenation was performed at a hydrogen pressure of 7 MPa (G) and a reaction temperature of 180 ° C. for 4 hours. After cooling, the catalyst was separated by filtration, and the filtrate was distilled under reduced pressure to obtain 242 g of a 70 ° C./0.12 kPa (0.9 mmHg) fraction. The fraction was analyzed by mass spectrum and nuclear magnetic resonance spectrum. As a result, the fraction was found to be 2-hydroxymethyl-3-methylbicyclo [2.2.1] heptane and 3-hydroxymethyl-2-methylbicyclo [2.
2.1] Heptane was confirmed.

Next, 15 g of γ-alumina (Norton Alumina SA-6273 manufactured by Nikka Seiko Co., Ltd.) was placed in a flow-type atmospheric pressure reaction tube made of quartz glass having an outer diameter of 20 mm and a length of 500 mm. Space velocity (WHSV)
A dehydration reaction was performed at 1.07 hr ^-1 and 2-methylene-3-
Methylbicyclo [2.2.1] heptane and 65% by mass of 3-methylene-2-methylbicyclo [2.2.1] heptane and 2,3-dimethylbicyclo [2.2.1] hept-2-ene 28 196 g of a dehydration reaction product of 2-hydroxymethyl-3-methylbicyclo [2.2.1] heptane and 3-hydroxymethyl-2-methylbicyclo [2.2.1] heptane each containing 1% by mass were obtained.

(Preparation of dimer hydride) 9.5 g of activated clay (manufactured by Mizusawa Chemical Co .; Galleon Earth NS) and 190 g of the olefin compound obtained above were placed in a 500 ml four-necked flask, and heated at 145 ° C. The mixture was stirred for a time to perform a dimerization reaction. After filtering the activated clay from the reaction mixture, 6 g of a nickel / diatomaceous earth catalyst for hydrogenation [N-113, manufactured by Nikki Chemical Co., Ltd.] was added to a 1 liter autoclave, hydrogen pressure was 4 MPa (G), reaction temperature was 160 ° C., and reaction was carried out. The hydrogenation reaction was performed under the conditions of 4 hours. After completion of the reaction, the catalyst was removed by filtration, and the filtrate was distilled under reduced pressure to give a boiling point of 126 to 128 ° C / 0.03 kPa (0.2 m
116 g of dimer hydride of the mHg) fraction were obtained. The dimer hydride was analyzed by mass spectrum and nuclear magnetic resonance spectrum, and as a result, was found to be a bicyclo [2.2.1] heptane derivative represented by the above formula (VII).
Table 1 shows the measurement results of the general properties and the traction coefficient.

Comparative Example 3 In Example 1, the catalyst for the dimerization reaction was changed to a boron trifluoride diethyl ether complex (8 g).
Was replaced with 20 g of 116% polyphosphoric acid, and 280 g of a dimer hydride was obtained in the same manner except that the dimerization reaction was carried out at 100 ° C. instead of at 20 ° C. The dimer hydride was analyzed by mass spectrum and nuclear magnetic resonance spectrum, and as a result, was found to be a bicyclo [2.2.1] heptane derivative represented by the above formula (VII). Table 1 shows the measurement results of the general properties and the traction coefficient.

The measurement of the traction coefficient in the above Examples and Comparative Examples was performed using a two-cylinder friction tester. That is, a cylinder of the same size in contact (diameter 52
mm, thickness 6mm, the driven side is a Tyco type with a radius of curvature of 10mm, and the driving side is a flat type without crowning). Apply a load of 98.0N with the weight,
The tangential force generated between the two cylinders, that is, the traction force was measured, and the traction coefficient was determined. This cylinder is bearing steel SU
J-2 Mirror finish, average peripheral speed 6.8m /
s, the maximum Hertz contact pressure was 1.23 Gpa. In measuring the traction coefficient at a fluid temperature (oil temperature) of 140 ° C., the oil temperature was raised from 40 ° C. to 140 ° C. by heating the oil tank with a heater.
The traction coefficient at a slip ratio of 5% was determined.

[0063]

[Table 1]

[0064]

[Table 2]

[0065]

The present invention provides a novel compound, a bicyclo [2.2.1] heptane derivative. Further, the bicyclo [2.2.1] heptane derivative can be produced economically and efficiently by the production method of the present invention. In addition, the bicyclo [2.2.1] heptane derivative or the traction drive fluid of the present invention has a high traction coefficient at high temperatures and excellent low-temperature viscosity characteristics, and is suitable for use worldwide from cold regions to high temperatures. Traction drive CVT
Available as oil.

[Brief description of the drawings]

Fig. 1: Mass chromatogram of component A

FIG. 2: ¹ H-NMR spectrogram of component A

FIG. 3: ¹³ C-NMR spectrogram of component A

FIG. 4: ¹³ C- ¹³ C two-dimensional NMR spectrogram of component A

FIG. 5: ¹ H- ¹³ C two-dimensional NMR spectrogram of component A

FIG. 6: Mass chromatogram of B component

FIG. 7: ¹ H-NMR spectrogram of component B

FIG. 8: ¹³ C-NMR spectrogram of component B

FIG. 9: ¹³ C- ¹³ C two-dimensional NMR spectrogram of component B

FIG. 10: ¹ H- ¹³ C two-dimensional NMR spectrogram of component B

FIG. 11: Mass chromatogram of C component

FIG. 12: ¹ H-NMR spectrogram of component C

FIG. 13: ¹³ C-NMR spectrogram of C component

FIG. 14: ¹³ C- ¹³ C two-dimensional NMR spectrogram of C component

FIG. 15: ¹ H- ¹³ C two-dimensional NMR spectrogram of C component

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme court ゛ (Reference) C10N 20:00 C10N 20:00 C Z 20:02 20:02 20:04 20:04 30:02 30: 02 30:08 30:08 40:04 40:04 F term (reference) 4H006 AA01 AA02 AA03 AB60 AC21 AD31 BA61 BA66 BA67 BE20 4H039 CA10 CL11 4H104 BA02A EA01A EA02A EA03A EA04A EA06A LA01 LA04 PA03

Claims (10)

[Claims] 1. exo-2-methyl-exo-3-methyl-endo-2-[(endo-3-methylbicyclo [2.2.1] hept-exo-2-yl) methyl] bicyclo [2. 2.1] Heptane, exo-2-methyl-
exo-3-methyl-endo-2-[(endo-2
-Methylbicyclo [2.2.1] hept-exo-3-
Yl) methyl] bicyclo [2.2.1] heptane, en
do-2-methyl-exo-3-methyl-exo-2-
[(Exo-3-methylbicyclo [2.2.1] hept-exo-2-yl) methyl] bicyclo [2.2.1]
Heptane, endo-2-methyl-exo-3-methyl-exo-2-[(exo-2-methylbicyclo [2.
2.1] Hept-exo-3-yl) methyl] bicyclo [2.2.1] heptane, endo-2-methyl-ex
o-3-methyl-exo-2-[(endo-3-methylbicyclo [2.2.1] hept-endo-2-yl) methyl] bicyclo [2.2.1] heptane, and e
ndo-2-methyl-exo-3-methyl-exo-2
-[(Endo-2-methylbicyclo [2.2.1] hept-endo-3-yl) methyl] bicyclo [2.
2.1] One or more bicyclo [2.2.1] heptane derivatives selected from heptane. 2. exo-2-methyl-exo-3-methyl-endo-2-[(endo-3-methylbicyclo [2.2.1] hept-exo-2-yl) methyl] bicyclo [2. 2.1] heptane and exo-2-methyl-exo-3-methyl-endo-2-[(endo-
2-methylbicyclo [2.2.1] hept-exo-3
-Yl) methyl] bicyclo [2.2.1] heptane; a bicyclo [2.2.1] heptane derivative. 3. Endo-2-methyl-exo-3-methyl-exo-2-[(exo-3-methylbicyclo [2.2.1] hept-exo-2-yl) methyl] bicyclo [2. 2.1] heptane and endo-2-methyl-exo-3-methyl-exo-2-[(exo-2
-Methylbicyclo [2.2.1] hept-exo-3-
Yl) Bicyclo [2.2.1] heptane derivative comprising a mixture with methyl] bicyclo [2.2.1] heptane. 4. Endo-2-methyl-exo-3-methyl-exo-2-[(endo-3-methylbicyclo [2.2.1] hept-endo-2-yl) methyl]
Bicyclo [2.2.1] heptane and endo-2-methyl-exo-3-methyl-exo-2-[(endo
-2-Methylbicyclo [2.2.1] hept-endo
-3-yl) methyl] bicyclo [2.2.1] heptane; a bicyclo [2.2.1] heptane derivative. 5. exo-2-methyl-exo-3-methyl-endo-2-[(endo-3-methylbicyclo [2.2.1] hept-exo-2-yl) methyl] bicyclo [2. 2.1] Heptane, exo-2-methyl-
exo-3-methyl-endo-2-[(endo-2
-Methylbicyclo [2.2.1] hept-exo-3-
Yl) methyl] bicyclo [2.2.1] heptane, en
do-2-methyl-exo-3-methyl-exo-2-
[(Exo-3-methylbicyclo [2.2.1] hept-exo-2-yl) methyl] bicyclo [2.2.1]
Heptane and endo-2-methyl-exo-3-methyl-exo-2-[(exo-2-methylbicyclo [2.2.1] hept-exo-3-yl) methyl] bicyclo [2.2.1] ] A bicyclo [2.2.1] heptane derivative comprising a mixture of heptane. 6. Endo-2-methyl-exo-3-methyl-exo-2-[(exo-3-methylbicyclo [2.2.1] hept-exo-2-yl) methyl] bicyclo [2. 2.1] Heptane, endo-2-methyl-exo-3-methyl-exo-2-[(exo-2-
Methylbicyclo [2.2.1] hept-exo-3-yl) methyl] bicyclo [2.2.1] heptane, end
o-2-methyl-exo-3-methyl-exo-2-
[(Endo-3-methylbicyclo [2.2.1] hept-endo-2-yl) methyl] bicyclo [2.2.
1] heptane, and endo-2-methyl-exo-3
-Cyclo-2.2 comprising a mixture of -methyl-exo-2-[(endo-2-methylbicyclo [2.2.1] hept-endo-3-yl) methyl] bicyclo [2.2.1] heptane. .1] heptane derivatives. 7. 2-methylene-3-methylbicyclo [2.2.1] heptane, 3-methylene-2-methylbicyclo [2.2.1] heptane and 2,3-dimethylbicyclo [2.2. 1] 1 selected from hept-2-ene
One or more bicyclo [2.2.1] heptane ring compounds are dimerized at 60 ° C. or lower in the presence of an acid catalyst, and the resulting dimer is reacted at 220 to 280 ° C. in the presence of a hydrogenation catalyst. 6. The bicyclo [2.2.
1] A method for producing a heptane derivative. 8. Methylene-3-methylbicyclo [2.2.1] heptane, 3-methylene-2-methylbicyclo [2.2.1] heptane and 2,3-dimethylbicyclo [2.2. 1] 1 selected from hept-2-ene
One or more bicyclo [2.2.1] heptane ring compounds are dimerized at 60 ° C. or lower in the presence of an acid catalyst, and the resulting dimer is reacted at 170 to 220 ° C. in the presence of a hydrogenation catalyst. 7. The bicyclo [2.2.
1] A method for producing a heptane derivative. 9. The method according to claim 7, wherein the acid catalyst is a Lewis acid.
2. The method for producing a bicyclo [2.2.1] heptane derivative according to item 1. 10. A bicyclo [2.2.1] heptane derivative according to any one of claims 1 to 6, or a compound according to claims 7 to 9.
A traction drive fluid comprising a bicyclo [2.2.1] heptane derivative obtained by the production method according to any one of the above, and a synthetic oil having the following physical properties as a base oil. (1) Molecular weight: 210 or more (2) Kinematic viscosity at 40 ° C: 10 to 25 mm ² / s (3) Viscosity index: 60 or more (4) Pour point: -40 ° C or less (5) Low temperature viscosity at -40 ° C: 150,000 mP
(6) Density at 20 ° C .: 0.93 g / cm ³ or more (7) Traction coefficient at 140 ° C .: 90% or more of the value of 2,4-dicyclohexyl-2-methylpentane