JPH02174729A - 1,1-dicyclohexylcycloalkane derivative, its production method, and traction drive fluid containing the same - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel compound 1,1-dicyclohexylcycloalkane derivative, a method for producing the same, and a traction drive fluid containing the same.

[Prior art and problems to be solved by the invention] Research has been conducted to reduce the size and weight of traction drive devices, mainly for automobile applications, and as a result, the requirements for the traction drive fluid used in the devices have also become stricter. Performance that can withstand use under various conditions, especially stable high performance over a wide temperature range from low to high temperatures, such as high traction coefficient from low to high temperatures, low viscosity, and excellent oxidation stability. etc. are required.

Various compounds have been proposed as traction drive fluids (Japanese Patent Publication No. 46-338, No. 4).
6-339). However, conventional traction drive fluids do not fully satisfy the above-mentioned required performance. For example, a compound that exhibits a high traction coefficient at high temperatures has a high viscosity near room temperature, and at lower temperatures, the viscosity increases significantly, resulting in poor fluidity, large stirring losses, and reduced transmission efficiency. there were. On the other hand, compounds that have a low viscosity near room temperature have excellent transmission efficiency at low temperatures, but have a low traction coefficient at high temperatures, and their viscosity decreases too much at high temperatures, causing problems in the lubrication of traction transmission devices. It had become.

[L1! Means for Solving the Problem] Therefore, the present inventors conducted extensive research in order to develop a traction drive fluid that satisfies the above-mentioned required performance.

As a result, we found that the new compound alone has the properties of a high traction coefficient and low viscosity at high temperatures, that these properties are maintained even when blended with other compounds, and that the new compound can be manufactured efficiently. find a way to
This led to the completion of the present invention.

That is, the present invention provides a 1,1-dicyclo5xylcycloalkylene conductor C represented by the following formula (R1,1
2, R3, H4, n'l and R6 represent a hydrogen atom or a lower alkyl group, and these may be the same or different. There is a plurality of R3, R4, R8 or R6 in one molecule. In this case, a plurality of R3, R4, R4 or R6 may be the same or different, and any two of R3, R4, R8 or R6 together form an alkylene group. 0m and n are O
It is an integer of ~6, and m+n=4-6. ), and also provides a compound represented by the following formula (II) (wherein R1, R2, R3, R4, R5 and R6 are the same as above. m and n are also the same as above). A method for producing a 1,1-dicyclohexylcycloalkane solid conductor represented by the above formula (1), characterized in that hydrogen, a hydrogenation catalyst, and a dehydration catalyst are coexisted in the mixture, and a hydrogenation treatment and a dehydration treatment are performed in combination. The compound represented by the formula (II) is hydrogenated to form a compound represented by the following formula (Ill) (wherein R1, R2, R', R4,
RS and l'R' are the same as above. Further, m and n are also the same as above. ), followed by dehydration and hydrogenation.
A method for producing a 1-dicyclohexylcycloalkane conductor is provided. Furthermore, the present invention provides a traction drive fluid containing a 1,1-dicyclohexylcycloalkane rust conductor represented by the formula (I).

The 1,1-dicyclohexylcycloalkane conductor represented by the formula (1) has no known compounds and is a new compound.

This new compound can be produced using the compound represented by the above formula (Natsu 1) as a raw material. That is, the compound represented by the formula (II) is hydrogenated to form a compound represented by the formula (III), and then a new compound represented by the formula (1) is obtained by dehydration and hydrogenation. In the present invention, R1, R2, R3R4, R8 and R6 in the formula represent a hydrogen atom or a lower alkyl group. As a lower alkyl group,
Examples include alkyl groups having 1 to 6 carbon atoms, such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, and isobutyl group. nl, R2, R3, R4, nl
1 and R6 may be the same or different.

In addition, when there is a plurality of R3, R4, 35 or R6 in one molecule, the plurality of R3, R4, R5 or R6 may be the same or different. For example, when m = 2, R3 may be a methyl group or an ethyl group.

Furthermore, any two of R3, R4, R8 and R6 may be combined to form an alkylene group. Such alkylene groups have 1 to 12 carbon atoms and may be straight or branched, such as methylene groups, ethylene groups,
Propylene group, trimethylene group, isopropylidene group,
Examples include isobutylene group.

In order to obtain the novel compound represented by the formula (1) from the compound represented by the formula (11), the reaction method of the present invention is to carry out the reaction in the coexistence of hydrogen, a hydrogenation catalyst, and a dehydration catalyst. ■ A method of reacting using hydrogen, a hydrogenation catalyst, and a dehydration catalyst simultaneously; ■ A method of first reacting using hydrogen and a hydrogenation catalyst, and then reacting using hydrogen, a hydrogenation catalyst, and a dehydration catalyst; ■First, react with hydrogen using a hydrogenation catalyst,
Next, there are three methods of reacting using a dehydration catalyst and then reacting again using hydrogen and a hydrogenation catalyst.
Although any method may be used, method (2) is preferred because it allows the reaction to be completed in one batch and saves time and effort.

The hydrogenation catalyst used in the above reaction includes nickel,
Commonly used materials containing one or more metals such as ruthenium, palladium, platinum, rhodium, iridium, copper, chromium, molybdenum, cobalt, and tungsten can be mentioned. Further, a catalyst in which the above-mentioned metal is supported on a carrier such as activated carbon may be used, and a solid acid catalyst is suitable as a dehydration catalyst. Examples of such a catalyst include white earths such as activated clay and acid clay, zeolites, Commonly used catalysts include silica, alumina, silica-alumina, cation exchange resins, and heteropolyacids.9 The amount of each catalyst used in the present invention is 0.1-100% by weight of the hydrogenation catalyst. %, preferably 1-20% by weight
, the solid acid catalyst is 0.1 to 100% by weight, preferably 1 to 100% by weight.
It is 20% by weight.

Further, the above reaction can also be carried out using a solvent. In this case, the solvent that can be used is n-
Examples include saturated hydrocarbons such as pentane, n-hexane, decane, cyclopentane, cyclohexane, methylcyclohexane, ethylcyclohexane, and decalin, aromatic hydrocarbons such as benzene, toluene, xylene, and tetralin, and polar solvents such as acetone ethanol. When an aromatic hydrocarbon is used, the solvent is also hydrogenated, and when a polar solvent is used, the solvent may be hydrogenated or dehydrated, so it is preferable to use a saturated hydrocarbon.

The above reaction is carried out at room temperature to 300°C, preferably at room temperature to 220°C.
℃, normal pressure to 200 kg/cm2G, preferably 5 to 1
50kg/cm2G for 0.5 to 24 hours, preferably 1
In order to efficiently carry out the 0 reaction which lasts for ~8 hours, first 12 hours are required.
Hydrogenation was carried out by holding at around 0°C for about 2 hours, then 1
It is preferable to hold the temperature at 80 to 2θO<0>C for about 2 hours to perform dehydration and hydrogenation. Here, if the temperature is lower than room temperature, the dehydration reaction will be difficult, and if it exceeds 300°C, the raw material represented by the above formula (!) will easily decompose, which is undesirable.
After the reaction is completed, if the catalyst is removed in duplicate, the above formula (
A compound represented by I) is obtained. Specific examples of this compound include 1,1-dicyclohexylcyclopentane;
1-Cyclohexyl-1-(methylcyclohexyl)-
Cyclopentane: 1-cyclohexyl-1-(ethylcyclohexyl)-cyclopentane; 1-cyclohexyl-1-(propylcyclohexyl)-cyclopentane:
1-cyclohexyl-1-(butylcyclohexyl)-
Cyclopentane, 1.1-di(methylcyclohexyl)-cyclopentane = 1-(methylcyclohexyl)-
1-(ethylcyclohexyl)-cyclopentane; 1.
1-di(ethylcyclohexyl)-cyclopentane,
1.1-dicyclohexyl-(methylcyclopentane)
;1-cyclohexyl-1-(methylcyclohexyl)
-(methylcyclopentane): 1-cyclohexyl-1
-(ethylcyclohexyl)-(methylcyclopentane): 1-cyclohexyl-1-(methylcyclohexyl)-(ethylcyclopentane); 1,1-di(methylcyclohexyl)-(methylcyclopentane), 1.1 −
Dicyclohexyl-(dimethylcyclopentane); 1.
1-dicyclohexyl-(methylethylcyclopentane), 1,1-dicyclohexylcyclohexane; l-cyclohexyl-1-(methylcyclohexyl)cyclohexane: 1-cyclohexyl-1-(ethylcyclohexyl)cyclohexane; 1-cyclohexyl-1-(propylcyclohexyl)cyclohexane; 1-cyclohexyl-1-(butylcyclohexyl)cyclohexane: 1,1-di(methylcyclohexyl)cyclohexane: 1-(methylcyclohexyl)-1-(ethylcyclohexyl) Cyclohexane; 1.1-di(ethylcyclohexyl)cyclohexane; 1.1-dicyclohexyl-(methylcyclohexane); l-cyclohexyl-
1-(methylcyclohexyl)-(methylcyclohexane); 1-cyclohexyl-1-(ethylcyclohexyl)-(methylcyclohexane); 1-cyclohexyl-1-(methylcyclohexyl)-(ethylcyclohexane); 1, 1-di(methylcyclohexyl)-(methylcyclohexane); 1,1-dicyclohexyl-(dimethylcyclohexane); 1,1-dicyclohexyl-
(methylethylcyclohexane); 2,2-dicyclohexyl-[2,2,1]bicyclohebutane, 2-cyclohexyl-2-(methylcyclohexyl) -[2,2
,11bicyclohexyl-2.2-di(methylcyclohexyl)[2,2,1]bicyclohebutane;2,2-dicyclohexyl-1,7,7trimethyl-[2,2,1
] Bicyclohebutane; 8,8-dicyclohexyl-[
4,3,0]bicyclononane; 2,2-dicyclohexyl-[2,2,2]bicyclooctane, and the like.

1 expressed by the above formula (1) obtained in this way,
The 1-dicyclohexylcycloalkane conductor has a high traction coefficient at high temperatures and a low viscosity, so it is suitable as a traction drive fluid.

Moreover, this 1,1-dicyclohexylcycloalkane conductor can be blended and used as other traction drive fluids. In this case, the 1,1-dicyclohexylcycloalkane conductor is contained in the total traction drive fluid in an amount of 1% by weight or more, preferably 5 to 60% by weight.
% by weight.

In this way, the 1,1-dicyclohexylcycloalkane conductor of the present invention can be used in blends with other traction drive fluids to increase the traction coefficient, and also to provide lower traction coefficients than conventional traction drive fluids. Because of its viscosity, it is also possible to increase the blend ratio to increase the traction coefficient.

[Example] Next, the present invention will be explained by examples.

Example 1 101.79 g of 1.1-bis(4-hydroxyphenyl)-cyclohexane (trade name: Bisphenol Z1 manufactured by Honshu Kagaku ■) was placed in an autoclave at 1°C.

5% by weight ruthenium/activated carbon catalyst for hydrogenation (manufactured by Nippon Engelhard) 30.40 g, activated clay (product name: Galleon Earth NS, manufactured by Mizusawa Chemical) 50.40
The reaction was carried out for 2 hours at a hydrogen pressure of 75 kg/cm"G and a temperature of 120°C.Then, the temperature was raised to 190°C and the reaction was further carried out for 2 hours.The reaction was completed. After that, cool it down.
A catalyst? The solvent was distilled off from door to door. The product 'H-N
MR analysis revealed that there were no aromatic peaks or olefin peaks, and the hydrogenation rate was 999% or more. In addition, analysis by C-NMR shows that there is one quaternary carbon, two tertiary carbons, and only secondary carbons remain, and analysis by GC-MS shows that the molecular weight is 248 (C1lll
)132), and when analyzed by GC (FID), the product showed a single peak (retention time: 15.1 IIlin
), and it turned out that there was no raw material left at all. The gas chromatography analysis conditions are column: 0V-7,2
m, 5115 column; column temperature = 80°C ~ 330°C
℃ at 10℃/min; Inlet temperature = 350℃ Nicarrier gas: N2.45mf/min; Detector: F
I used it as an ID. From these results, the product has the structural formula 11:
+8) It was identified as 13□ 1,1-dicyclohexylcyclohexane. The yield was 92.4g. 'H-NMR, 'C-NMR and GC-MS charts of this product are shown in Figures 1, 2 and 3, respectively.The properties of this product are as shown below.

Kinematic viscosity: 34.24cSt (@40℃) 4.39
9cSt (@100℃) Viscosity index knee 50 Specific gravity: (1574℃) 0.9583 Refractive index:
(nd") 1.5131Furthermore, the traction coefficient of this material was measured in the temperature range of 40°C to 140°C, and the results are shown in Figure 4.The traction coefficient was measured using a 2-cylindrical friction tester. In other words, cylinders of the same size (diameter 52 mm, height 6 mm)
The driven side is a tyco type with a radius of curvature of 10 + + + m, and the driving side is a flat type without crowning), and one side is set at a constant speed (
1500rpm) and the other from 150Orpm to 175
It was rotated continuously to 0 rpm, a 7 kg load was applied to the contact portion of both cylinders by a spring, and the tangential force generated between the two cylinders, that is, the traction force, was measured to determine the traction coefficient. This cylinder was made of bearing steel 5UJ-2 with a mirror finish, and the maximum Hertzian contact pressure was 112 kgf/ma+2.

In addition, in measuring the relationship between the traction coefficient and oil temperature, the oil temperature was varied from 40°C to 140°C by heating the oil tank with a heater, and the relationship between the traction coefficient and oil temperature at a slip rate of 5% was measured. is plotted.

Example 2 The same operation as in Example 1 was performed except that the reaction temperature was set at 190° C. from the beginning and the reaction was carried out for 4 hours. When the product was analyzed by GC (FID), peaks similar to those in Example 1 were obtained, but the selectivity was 90%.

Example 3 2200 g of bisphenol was placed in a No. 11 autoclave, and 30.28 g of 5rf 1% ruthenium/activated carbon catalyst for hydrogenation was added.
g and acetone 400a+j as a solvent,
The reaction was carried out for 3 hours at a hydrogen pressure of 75 kg/cm'G and a temperature of 130°C. After the reaction was completed, the reactor was cooled and the catalyst was separated from the reactor, and the reactor fluid was analyzed, and it was found that all of the acetone solvent had been converted to isopropyl alcohol. The product was subjected to GC (FID
) As a result of the analysis, three components were recognized, the same peak as in Example 1 was about 5%, and the peak at 17.5++in was 15%.
A peak of about 80% was observed at 20.8 m1n. Next, when the solvent was distilled off, it solidified, so it was recrystallized with hexane to obtain a component with a peak of 20.8 m1n with a purity of 98%.

Analysis by ') I-NMR, '3C-NMR, and GC-MS revealed that this component was 1,1-bis(4-hydroxycyclohexyl)-cyclohexane. Yield was 135 g.

Then, 109.56 g of the obtained 1,1-bis(4-hydroxycyclohexyl)-cyclohexane, 30.40 g of 5 wt% ruthenium/activated carbon catalyst for hydrogenation, 50.40 g of activated clay, and 500 mj of ethylcyclohexane as a solvent were again added. It was charged into the above-mentioned 11 autoclave and heated at a hydrogen pressure of 60 kg/cm'G and a temperature of 195°C.
After 0 hours of reaction, after cooling and separating the catalyst, the liquid was analyzed by GC (FID) and found to be 20.8 m
The 1n peak completely disappeared, and the 1n peak obtained in Example 1
A peak of 5.1 m1n was obtained with a selectivity of 95%.

Comparative example 1 522g of toluene in a 4-hole flask.

27.6 g of anhydrous aluminum chloride and 1 nitromethane
2.6 g of methallyl chloride was added thereto, and while stirring at 10° C., 181.2 g of methallyl chloride was added dropwise over 2 hours, and stirring was continued for an additional hour to complete the reaction. This and 75m of water
After adding 1 liter of aluminum chloride to decompose the aluminum chloride and then separating the oil layer, the oil layer was washed once with water 2001, twice with 300 mj of 1N aqueous sodium hydroxide solution, and dried over anhydrous magnesium sulfate. After distilling off unreacted raw materials using a rotary evaporator, the boiling point is 11% by distillation under reduced pressure.
0-115℃ 10.12mmHg fraction 262.5g
I got it. As a result of analyzing the obtained fraction, this fraction was 2-
It was found to be 75% methyl-1,2-ditolylpropane and 25% of the isomerized product 2-methyl-1,1-ditolylpropane.

Subsequently, 250 g of the obtained fraction was placed in an autoclave No. 11, and a nickel catalyst (manufactured by JGC Chemical ■: N-113) was added.
Add 20g, hydrogen pressure 85kg/cm'G, temperature 1
Hydrogenation was carried out at 70° C. for 6 hours. After cooling, the catalyst was heated and the product was analyzed, and the hydrogenation rate was 99.
It was found that 2-methyl-1,2 di(methylcyclohexyl)propane was 75% and 2-methyl-1,1-di(methylcyclohexyl)propane was 25%. Further, the properties of this product are as shown below.

Kinematic viscosity: 14.84cst (@40℃) 2.84
4cSt (@100℃) Viscosity index knee 22 Specific gravity: (1574℃) 0.8860 Refractive index:
(d'') 1.4813 Furthermore, the traction coefficient of this product was measured in the same manner as in Example 1, and the results are shown in FIG.

Example 4 The 1,1-dicyclohexylcyclohexane obtained in Example 1 and the fluid obtained in Comparative Example 1 were blended at a ratio of 1:1, and the traction coefficient was determined in the same manner as in Example 1. It was measured. The results are shown in FIG. Further, the properties of this fluid are as shown below.

Kinematic viscosity: 20.96cSt (@40℃) 3.45
6cSt (@100℃) Viscosity index knee 30 Specific gravity: (1574℃) 0.9199 Refractive index:
(nd") 1.4961 Example 5 102.57 g of cyclohexanone in a IIl separable flask equipped with a gas inlet tube, stirrer and thermometer.
, phenol 76.65 g, orthocresol 186
．． 27 g and 8 mi' of thioglycolic acid were charged, and the mixture was stirred at 54° C. for 3 hours while bubbling hydrogen chloride gas. After 3 hours, the contents became a purple solid. Next, stop blowing in hydrogen chloride gas, and add 2
00 mA' and 200 mj+ of hot water of 70 to 80°C were added and stirred at 70°C for 1 hour. As a result, the lumps loosened and became pink crystals, so they were cooled to room temperature.
The crystals were separated by vacuum filtration. When this crystal was recrystallized with a mixed solvent of toluene-ethanol (20:1), 235 g of white crystal with a slight light purple color was obtained.

When the obtained crystals were dissolved in acetone and analyzed by GC (FID), three components, a, b, and c, were observed. The analysis conditions were: Column: 0V-101 (capillary) 50m; Column temperature: 280-300°C at 2°C/ll.
The temperature was increased by 1 inch; other conditions were the same as in the case of the 2M column.

The retention times of the three components are a: 8.1 m1n, b:
8.6m1n.

C: It was 9.0 m1n. Also, the component ratio is a:b:
c=10:22:68. 'H-NMR
, 13C-NMR.

As a result of analysis by GC-MS and analysis of test sample bisphenol 2, a is bisphenol Z, b is cyclohexane with one phenol and one orthocresol bonded to the 1 position, and C is cyclohexane with orthocresol bonded to the 1 position. It turned out that it was a combination of two.

Next, 180 g of the obtained crystals were charged into an IJ2 autoclave, and 15.2 g of a 5% by weight ruthenium/activated carbon catalyst for hydrogenation (manufactured by Nippon Engelhardt Co., Ltd.) was added.

25.4 g of USY type zeolite (H5Z-330HLI^: manufactured by Tosoh) and 400 g of dioxane as a solvent.
Add al, hydrogen pressure 75kg/ca+'G, temperature 12
The reaction was carried out at 0°C for 2 hours. After that, increase the temperature further by 2
The temperature was raised to 10°C and the reaction was continued for an additional 5 hours. After the reaction was completed, the product was treated and analyzed in the same manner as in Example 1, and it was found that there were no hydroxyl groups at all and the hydrogenation rate was 99.9% or more. Also, GC (FID) and GC-1
According to analysis by 45, CI +! l I+ 1 of 32
．． 9% 1-dicyclohexylcyclohexane + '1
9H34's 1=cyclohexyl-1-(3-methylcyclohexyl)cyclohexane is 24% + 620836
of 1,1-di(3-methylcyclohexyl)cyclohexane was found to be 67%. Yield: 118 g
Met. A portion of this was taken and fractionated by liquid chromatography. J-NMR of C19H1+, "C-
The NMR and GC-MS charts are shown in Figure 5, respectively.
Shown in FIGS. 6 and 7. Further, the properties of the obtained crystal as a whole are as shown below.

Kinematic viscosity: 43.63cSt (@40℃) 4.65
4cSt (@100℃) Viscosity index knee 101 Specific gravity, (15/4℃) 0.9403 Refractive index: (nd") 1.5048 Furthermore, the traction coefficient of this product was measured in the temperature range from 40℃ to 140℃ The results are shown in Figure 4.

Example 6 In a separable flask at 1°C equipped with a stirrer and a thermometer, 101.24 g of cyclohexanone, 273.78 g of orthocresol, and 11.98 g of concentrated hydrochloric acid (35%) were added.
g and 8 mR of thioglycolic acid, and heated at 60°C for 1
．． Stirring was performed for 5 hours. The contents solidified and became like a slurry, so 300ml of water and 30ml of dioxane were added.
0++l was added and stirred at 80°C for 1 hour. Next, 20 g of sodium chloride was added and the mixture was separated into two layers, and then the organic layer was separated and washed twice with water 2001.

When light components were distilled off using a rotary evaporator, crystals were precipitated, and when this was recrystallized from a mixed solvent of toluene-ethanol (20:1), 184 g of white crystals were obtained. Take a part of the obtained crystal')
When analyzed by I-NMR, C-NMR, and GC-MS, it was confirmed that there is one component, and this component is 1.
It turned out to be 1-bis(4-hydroxy-3-methylphenyl)-cyclohexane. That is, the C component was the same as that obtained in Example 5.

Next, 180 g of the obtained crystals were subjected to a reaction in the same manner as in Example 5. After the reaction was completed, the product was treated and analyzed in the same manner as in Example 1, and it was found that there were no hydroxyl groups at all and the hydrogenation rate was 99.9% or more. Also, G
Analysis by C-MS, 'H-NMR and 'C-NMR revealed that this was the 1,1-di(3
-methylcyclohexyl)-cyclohexane. Yield was 148 g.

'H-NMR, '3C-NMR and GC-MS charts are shown in Figures 8, 9 and 1θ, respectively.

Moreover, the properties of this product are as shown below.

Kinematic viscosity: 51.24cSt (@40℃) 4.88
2cSt (@10C℃) Viscosity index, -121 Specific gravity, (15/4℃) 0.9332 Refractive index:
(mouth d") 1.5016 Furthermore, the traction coefficient of this thing was changed from 40℃ to 14
Figure 4 shows the results measured in a temperature range of 0°C.

Example 7 100.51 g of cyclopentanone, 2 phenol in an IJl separable flask equipped with a stirrer and thermometer
40.48 g of concentrated hydrochloric acid (35%), 200.00 g of thioglycolic acid, and 161 g of thioglycolic acid were charged, and stirred at 43° C. for 1 hour. Thereafter, when it was left to stand for one day, the contents solidified and became slurry-like, so this was separated by vacuum filtration and the obtained crystals were washed with water (100 ml) and meta-xylene 100a+4. After repeating this operation three times and drying the crystals, 12 white crystals were found.
8.38g was obtained. Take a part of the obtained crystal and 'H-
When analyzed by NMR, 13C-NMR, and GC-MS, it was confirmed that there is one component;
．． It turned out to be 1-bis(4-hydroxyphenyl)-cyclopentane. In addition, GC (FID) klm
The analysis conditions are: Column: 0V-101 (capillary) 50m: Column temperature = 280℃: Injection temperature: 3
50°C; carrier gas: N2.60m1/win. The retention time of the obtained crystal was 6.6 m1n.

Next, 120 g of the obtained crystals were charged into an autoclave No. 11, and 20.1 g of a 5% by weight ruthenium/activated carbon catalyst for hydrogenation (manufactured by Nippon Engelhard) and USY type zeolite (H5Z-330HIJA: manufactured by Tosoh) were added.
20.2 g and 400 mjl dioxane as solvent
was added, and the reaction was carried out at a hydrogen pressure of 80 kg/cm2G and a temperature of 120°C for 1 hour, and then at 150°C for 1.5 hours.

After that, the temperature was further increased to 215℃, and the hydrogen pressure was increased to 110℃.
kg/cm"G for 4.5 hours. After the reaction, the product was treated in the same manner as in Example 1.
Analysis by H-NMR revealed that there were no aromatic peaks or olefin peaks, and the hydrogenation rate was 99.9% or more. In addition, in analysis by C-NMR, 4
There is one class carbon, two tertiary carbons, and only secondary carbons remain, and according to GC-MS analysis, the molecular weight is 2:14.
(CI7H30), and GC (FrD) analysis revealed that the retention time was 4.3 ml, which was completely different from the raw material. From these results, the product has the structural formula CI? It was identified as H3° 1,1-dicyclohexylcyclopentane. Yield was 108.56g.

'H-NMR,'C-NMR and GC-M of this
The charts of S are shown in Figures 11, 12 and 1, respectively.
Shown in Figure 3. Further, the properties of this product are as shown below.

Kinematic viscosity: 25.72cSt (@40℃) 3.78
8 cSt (9100°C) Viscosity index knee 53 Specific gravity: (Is/4°C) 0.9586 Refractive index: (nd”) LsHl Furthermore, the traction coefficient of this material was changed from 40°C to 14
The results of measurements in a temperature range of 0° C. are shown in FIG. 14. The traction coefficient was measured in the same manner as in Example 1.

Example 8 91.9 g of cyclopentanone, 2 of orthocresol in 11 separable flasks equipped with stirrer and thermometer
43.20 g of concentrated hydrochloric acid (35%), 97.49 g of thioglycolic acid 8a+j were charged, and the mixture was stirred at 28°C for 3 hours. Thereafter, when it was left to stand for one day, the contents solidified and became slurry-like, so this was separated by vacuum filtration and the obtained crystals were washed with 100 nl of water and 100 ml of meta-xylene. After repeating this operation three times, the crystals were dried and one white crystal was found.
69.04 g was obtained. Take some of the crystals obtained.
)1-NMR, "C-NMR and GC-MS analysis revealed one component, and this component is 1.1-bis(4-hydroxy-3-methylphenyl)-cyclopentane. It turned out that GC (FI
D) The retention time with (capillary 50m) is 7.
It was 7m1n.

Next, 160 g of the obtained crystals were subjected to a reaction in the same manner as in Example 7. After the reaction was completed, the product was treated and analyzed in the same manner as in Example 7, and it was found that there were no hydroxyl groups at all and the hydrogenation rate was 99.9% or more. Also, G
Analysis by C-MS, 'H-NMR and 'C-NMH shows that this is a 1,1 di(Cl1i+)134.
It was identified as 3-methylcyclohexyl)-cyclopentane. The yield was 142.16g. GC (FI
The retention time according to D) was 4.8 m1n.

') I-NMR, '3C-NMR and G-MS charts are shown in Figures 15, 16 and 17, respectively. Further, the properties of this product are as shown below.

Kinematic viscosity: 61.82cSt (@40℃) 4.81
3cSt (@100℃) Viscosity index, -241 Specific gravity: (1574℃) 0.9426 Refractive index:
(nd") 1.5034Furthermore, the traction coefficient of this material was measured in a temperature range of 40°C to 140°C, and the results are shown in FIG.

Example 9 112.06 g of norcamphor, 235.92 g of phenol and 12+a thioglycolic acid were placed in a tX separable flask equipped with a gas inlet, stirrer and thermometer.
7 while adding il and bubbling hydrogen chloride gas.
Stirring was performed at 0°C for 6 hours. The contents became a dark brown solid. The blowing of hydrogen chloride gas was stopped, meta-xylene 2001Ili+ and water 2501 were added, and the mixture was stirred at 70° C. for 1 hour, whereby the agglomerates were loosened and pale pink crystals were precipitated. Then, cool to room temperature and vacuum tPA
After separating the crystals, the crystals were washed with 100+nj of water and 100+nil of meta-xylene. After repeating this operation three times, the crystals were dried to produce 163.
55g was obtained. Take a part of the obtained crystal ')I-NM
When analyzed by R,"C-NMR and GC-MS, it was recognized that there is one component, and this component is 2.2-
Bis(4-hydroxyphenyl) -[2,2,1]
It turned out to be bicyclohebutane. GC(FID
) (Capillary 50m) retention time is 10.8
It was m1n.

Next, 150 g of the obtained crystals were placed in 11 autoclaves, and the final stage temperature was set to 220°C in Example 7.
The reaction was carried out in the same manner as in Example 7 except for the following. After the reaction was completed, the product was treated and analyzed in the same manner as in Example 7, and it was found that there were no hydroxyl groups, aromatics, or olefins.
It was found that the hydrogenation rate was 99.9% or more. Also,
Analysis by GC-MS, '+1-NMR and 13C-NMR revealed that this product was 2.2- of C16)13□.
It was identified as dicyclohexyl[2,2,1]bicyclohebutane. Yield was 135.21 g. G
The retention time by C(FID) was 5.1 m1n.

'H-NMR, 'C-NMR and GC-MS charts are shown in Figures 18, 19 and 20, respectively.The properties of this product are as shown below.

Kinematic viscosity: 99.90cSt (@40℃) 6.77
2C5t (@ 100℃) Viscosity index knee 101 Ratio Iff: (15/4℃) 0.9819 Refractive index:
(nd'') 1.5200 Furthermore, the traction coefficient of this material was measured in a temperature range of 40°C to 140°C, and the results are shown in FIG.

Example 10 132.77 g of norcamphor, 325.33 g of orthocresol, and 1 portion of thioglycolic acid were placed in a separable flask equipped with a gas blowing tube, a stirrer, and a thermometer.
2mj) was charged and stirred at 74° C. for 7 hours while bubbling hydrogen chloride gas.

The contents became a dark brown solid. Stop blowing hydrogen chloride gas, and add 200 mR of meta-xylene and 200 mR of water.
' was added and stirred at 70°C for 1 hour, the agglomerates were loosened and a flaming 6 suspension was obtained. Next, it was cooled to room temperature, the crystals were separated by vacuum filtration, and then filtered with 100 m of water! ! and meta-xylene 10
The crystals were washed with 0ml. After repeating this operation three times, the crystals were dried to obtain 156.80 g of white crystals.

A part of the obtained crystal was taken and subjected to '+1-NMR.

"When analyzed by C-NMR and GflNy MS, it was confirmed that there is one component, and this component is 2.2-
Bis(4-hydroxy-3-methylphenyl)[2,2
, 1] was found to be bicyclohebutane. G.C.
(FID) (capillary 50 m) retention time was 11.7 m1n.

Next, 150 g of the obtained crystals were subjected to a reaction in the same manner as in Example 9. After the reaction was completed, the product was treated and analyzed in the same manner as in Example 7, and it was found that there were no hydroxyl groups, aromatics, or olefins, and the hydrogenation rate was 99.9% or more. Also, GC-MS.

By analysis by ) I-NMR and C-NMR, this substance was identified as 2,2-di(3-methylcyclohexyl) [2,2,1]bicyclohebutane of C211136. The yield was 131. It was 56g.
The retention time by C(FID) was 5.4 m1n.

'H-NMR, 'C-NMR and GC-MS charts are shown in Figures 21, 22 and 23, respectively.The properties of this product are as shown below.

Kinematic viscosity: 230.2cSt (@40℃) 8.33
7cSt (@ 100℃) Viscosity index knee 277 Specific gravity: (1574℃) 0.9660 Refractive index: (nd20) 1.5135 Furthermore, the results of measuring the traction coefficient of this product in the temperature range from 40℃ to 140℃ It is shown in FIG.

[Effects of the Invention] According to the present invention, a 1,1-dicyclohexylcycloalkal conductor, which is a new compound, can be efficiently produced. It has a high traction coefficient over a wide temperature range. Furthermore, since this compound has a high traction coefficient, it is possible to reduce the size and weight of the traction drive device and extend its life.

[Brief Description of the Drawings] Fig. 1, Fig. 2, and Fig. 3 show 1 in Example 1,
')I-NMR of 1-dicyclohexylcyclohexane
(Solvent: CDC1's), I3C-NMR (Solvent:
CDCRs) and GC-MS are shown, respectively. Fourth
The figure is a graph showing the relationship between fluid traction coefficient and temperature in Examples 1.4.5 and 6 and Comparative Example 1. Figures 5, 6 and 7 show 'H-NMR of l-cyclohexyl-1-(3-methylcyclohexyl)cyclohexane in Example 5 (solvent: CDCN5).
, '3C-NMR (solvent: CDCjs) and GC
Figures 8, 9 and 10, which respectively show -MS, show 'H-NMR of 1,1-di(3-methylcyclohexyl)cyclohexane in Example 6 (solvent: coc
p3), '3C-NMn (solvent: CDCRs)
and GC-MS are shown, respectively. Figures 11, 12, and 13 show 'H-NMR of 1,1-dicyclohexylcyclopentane in Example 7 (solvent: CD
Cj's), "C-NMR (solvent: CDCjs) and GC-MS, respectively. FIG. 14 shows Example 7.
, 8.9 and lO and a graph showing the relationship between the traction coefficient and temperature of the fluid in Comparative Example 1. 15, 16 and 17 are 1 and 1 in Example 8.
-di(3-methylcyclohexyl)cyclopentane'
Figures 18, 19 and 20 show 2,2-dicyclohexyl in Example 9. [2,2,1]')l-NMR of bicyclohebutane (solvent diCDCf3),
"C-NMR (solvent: CDCj's) and GC-M
S is shown respectively. Figures 21, 22 and 23 show the composition of 2,2-di(3-methylcyclohexyl)-[2,2,l]bicyclohebutane in Example 1O.
) I-NMR (solvent: CDCjs), “C-NM
R (solvent: CDCf3) and GC-MS are shown, respectively.

Claims (4)

[Claims] (1) A 1,1-dicyclohexylcycloalkane derivative represented by the following formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (In the formula, R^1, R^2, R^3, R^4, R^5 and R^6 are hydrogen atoms or lower alkyl groups and these may be the same or different. If there are multiple R^3, R^4, R^5 or R^6 in one molecule, multiple R^3, R ^4, R^5 or R^
6 may be the same or different. Also,
Any two of R^3, R^4, R^5 or R^6 may be combined to form an alkylene group. m and n are integers from 0 to 6, and m+n=4 to 6. ) (2) Compound represented by the following formula (II)▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formula, R^1, R^2, R^3, R^4, R^ 5 and R^6 represent a hydrogen atom or a lower alkyl group, and these may be the same or different. R^3, R^4, R^5 or R^6 in one molecule. If there are multiple R^3, R^4, R^5 or R^
6 may be the same or different. Also,
Any two of R^3, R^4, R^5 or R^6 may be combined to form an alkylene group. m and n are integers from 0 to 6, and m+n=4 to 6. 2. The method for producing a 1,1-dicyclohexylcycloalkane derivative according to claim 1, wherein hydrogen, a hydrogenation catalyst, and a dehydration catalyst are coexisting in the 1,1-dicyclohexylcycloalkane derivative. (3) A compound represented by the following formula (III) obtained by hydrogenating the compound represented by the formula (II) according to claim 2 ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ ... (III) (In the formula, R^1, R^2, R^3, R^4, R^5 and R^6 represent a hydrogen atom or a lower alkyl group, and these may be the same or different. 1 molecule If there are multiple R^3, R^4, R^5 or R^6 in it, multiple R^3, R^4, R^5 or R^
6 may be the same or different. Also,
Any two of R^3, R^4, R^5 or R^6 may be combined to form an alkylene group. m and n are integers from 0 to 6, and m+n=4 to 6. ), followed by dehydration and hydrogenation. (4) 1,1- represented by formula (I) according to claim 1
A traction drive fluid containing a dicyclohexylcycloalkane derivative.