JPS614796A - Production of synthetic lubricating oil - Google Patents

Abstract

PURPOSE:To obtain synthetic lubricating oil for traction drive, which has a high coefficient of traction, by hydrogenating a specified tetralin derivative or naphthalene derivative in the presence of a ruthenium or rhodium catalyst. CONSTITUTION:A compd. of formula I or II (wherein X<1> is a group of formula III, IV, V or VI; R is a 1-5C alkyl) such as 1,1'-bistetralin or 1,1-dinaphthyethane is hydrogenated in the presence of a ruthenium or rhodium catalyst to obtain the desired synthetic lubricating oil of formula VII (wherein X<2> is a group of formula VIIIor IX). Examples of compds. of formula VII are 1,1'-bisdecalin and 1,2-didecalypropane. The synthetic lubricating oil has a remarkably high coefficient of traction, as compared with that of an oil obtd. by carrying out the hydrogenation in the presence of other metal such as platinum or nickel.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing synthetic lubricating oil, and more particularly to a method for producing synthetic lubricating oil for traction drives having a high traction coefficient.

The traction drive fluid is a fluid used in traction drive devices such as various continuously variable transmissions. This drive device is designed to meet the demands for miniaturization and high speed.

It is required to be used under high load conditions.

The present inventors have conducted extensive research to develop a traction drive fluid that can withstand use under such harsh conditions. It has been known that compounds having two or more naphthene rings are preferable as traction drive fluids, and the present inventors have already developed compounds represented by the following formula, which are more effective than known ones. It was discovered that the compound has a higher traction coefficient at high temperatures.

These compounds are produced by dimerizing naphthalene or tetralin, followed by hydrogenation, or by subjecting naphthalene or tetralin to a Friedel-Crach reaction with alkenyl halides, alkyl cibarides, or aldehydes in the presence of an appropriate catalyst such as a nickel catalyst. However, as a result of repeated research, the present inventors discovered that an even higher traction coefficient could be obtained by using a ruthenium or rhodium catalyst during hydrogenation. The present invention was completed based on this knowledge.

The present invention provides a method for producing a synthetic lubricating oil represented by the following formula (g), which comprises hydrogenating a compound represented by the following formula (II) or (II) in the presence of a ruthenium or rhodium catalyst. Here, xl is C court Th, C fuya, C court〉g.

@tent, and R is an alkylene group having 1 to 5 carbon atoms. ) (Here, X is % or [stock], and R is an alkylene group having 1 to 5 carbon atoms.).

The compound represented by the above formula (I) or (ff) is a tetrari/or naphthalene derivative, and specific examples include 1. f-bistetralin, 1.2'-bistetralin, 1.1-ditetralylethane, 2-methyl-1,
Examples include 2-ditetrallylpropane, 1,2-ditetrallylbrovane, 1,1-dinaphthylethane, x,r-binaphthyl, and the like.

The conditions for hydrogenating the compound represented by formula (I) or (l[) above in the presence of a ruthenium or rhodium catalyst are a temperature of 10 to 300°C, preferably 50 to 200°C,
Pressure 1-200 Vtyn2Gs preferably 5-50
11V6++2G. Note that ruthenium or rhodium is often used supported on a commonly used carrier such as silica, alumina, or activated carbon, but there are various forms in which it is used.

Next, specific examples of the compound represented by formula I) are shown below.

Synthetic lubricating oil obtained by the method of the present invention has a significantly high relative traction coefficient when hydrogenated using other metals such as platinum and nickel as a catalyst, making it an excellent fluid for traction drives. The reason for this is thought to be that many decalin rings are in the cis form (meaning that the hydrogens attached to the carbons at the 9 and 10 positions are in the bus position).

The compound obtained by the present invention can be used as it is as a base stock for traction drive fluid, and has a small change in traction coefficient from low to high temperatures;
It also shows an excellent traction coefficient. therefore,
It not only contributes to the miniaturization of drive devices and can withstand use under harsh conditions of high temperature and high load, but is also suitable for continuously variable transmissions for automobiles, continuously variable transmissions for industrial use, hydraulic equipment, etc. It can be widely used in various devices.

Next, examples of the present invention will be shown. The traction coefficients in the Examples and Comparative Examples were measured using a two-cylindrical friction test eflK. That is, one of the cylinders of the same size (diameter 52111iK, thickness 6n) that are in contact with the Sl line is moved at a constant speed (200Or, p, m,), and the other cylinder is moved at a constant speed slower than the speed (II900r, p, m, ), and a spring is applied to the contact area of both cylinders to
A load of Kt was applied, the torque was measured using a strain gauge and a torque meter, and the traction coefficient was determined. This cylinder is made of bearing steel 8UJ-2, and the surface is alumina (0,
03μ) It has a puff finish than K, and the surface roughness is R.
][=0.2μ. Also, the average Hertzian contact pressure is 75
It was b7m2. When making measurements, heat the oil tank with a heater to keep the oil temperature from 60℃ to 140℃.
changed to.

Example 1 Tetralin 3960y and anhydrous aluminum chloride 1001 in a 5A' glass flask! was added, and the temperature inside the flask was cooled to 10°C with ice water. Next, 453 g of methallyl chloride was slowly added dropwise into the mixture over 5 hours while stirring, and the mixture was further stirred for 1 hour to complete the °C reaction.

Then, 700 cc of water was added to the flask to decompose the aluminum chloride and separate the oil layer. This oil layer was washed three times each with a 2N aqueous sodium hydroxide solution (1) and a saturated saline solution (1), and then with anhydrous sodium sulfate. Dry.

Next, a hakama with unreacted tetralin removed by distillation,
Boiling point 165-175℃ 10℃ 1nm by distillation under reduced pressure
700 g of Hg fraction was obtained. As a result of analyzing this fraction, 1
．． The main components are a 2:1 (molar ratio) mixture of dimerized products of raw materials such as 2'-bistetralin and 1,1'-bistetralin, and ring-opened dimerized products of raw materials such as 1-natralyl-4-phenylbutane. It was confirmed that it contained a small amount of 2-methyl-1,2-ditetralylbrobanes as a subcomponent.

Put 500cc of this into 11 autoclaves,
Add 10 g of 5% ruthenium carbon catalyst for hydrogenation (manufactured by Nippon Engelhardt Co., Ltd.) and 10 g of water, and hydrogen E5
Hydrogenation was carried out at 0 Ky/cm 2 and a reaction temperature of 150°C. After cooling, the reaction solution was filtered to separate the catalyst. After stripping the light components, analysis revealed a hydrogenation rate of 99.
．． 9% or more, which includes trimerized hydrogenated products such as 1,2'-bisdecalin and 1,1'-bisdecalin, and ring-opened trimerized hydrogenated products such as 1-decaryl-4-cyclohexylbutane. It was confirmed that a mixture of 2 (molar ratio) was the main component and contained a small amount of 2-methyl-1,2-decarylpropane as a subcomponent. The specific gravity of this material is 0095 (II5/4°C), and the kinematic viscosity is 75 cSt.
(40'C), 7. ocst (II 00°C), and the refractive index np was 1°5108.

The traction coefficient of this material was measured over a temperature range of 60° C. to 140° C. The results are shown in FIG.

Comparative Example 1 In Example 1, hydrogenation was carried out using 25 g of a nickel catalyst for hydrogenation (manufactured by JGC Chemical Co., Ltd., trade name: rN-113 Catalyst) at a hydrogen pressure of 50 622 and a reaction temperature of 20'0°C. Other than that, the operation was the same.

The resulting mixture has a specific gravity of 0.95 (II5/4°C) and a kinematic viscosity of 65 cst (40°C), 6,2
cst (II00°C), and the refractive index nv is 1.50
It was 93.

The traction coefficient of this material was measured over a temperature range of 60°C to 140°C, and the results are shown in FIG.

Example 2 The reaction was carried out in the same manner as in Example 1 except that allyl chloride 383y was used instead of methallyl chloride in Example 1, and the boiling point was 155 to 175°C (0.1 min).
750 g of fraction g) was obtained. 500 g of this fraction was mixed with a 5% rhodium-carbon catalyst (manufactured by Nippon Engelhardt Co., Ltd.) 15
The hydrogenation treatment was carried out in the same manner as in Example 1 except that 1,2-didecalylbrobanes were used as the main component, and 1-
550 g of a product containing decalyl-4-phenylbutane and 1,2-hystecalin was obtained. The obtained product has a refractive index n of 1.5076 and a specific gravity of 0-94 (II5/
4℃), kinematic viscosity 9 Q cst (40℃), 7,
6c, 5t (II00°C). The traction coefficient of this material was measured over a temperature range of 60° C. to 140° C. The results are shown in FIG.

Comparative Example 2 In Example 2, hydrogenation was carried out using hydrogen E using 25 g of a nickel catalyst for hydrogenation (manufactured by JGC Chemical, trade name: rN-113 Catalyst).
50 KK9/6n2. The same procedure was followed except that the reaction temperature was 200°C.

The specific gravity of the resulting mixture is O095 (II5/4°C), the refractive index nDi, s066 + kinematic viscosity 83C8t
(40'C), 7.5 cSt (II00°C).

The traction coefficient of this material was measured over a temperature range of 60° C. to 140° C. The results are shown in FIG.

[Brief explanation of the drawing]

FIGS. 1 and 2 are graphs showing the relationship between the traction coefficient and temperature of the compounds obtained in Examples.

Claims (1)

[Claims] A synthetic lubricating oil represented by the following formula (III), which is obtained by hydrogenating a compound represented by the following formula (I) or (II) in the presence of a ruthenium or rhodium catalyst. Production method. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) (Here, X^1 is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R is an alkylene group with 1 to 5 carbon atoms. be. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (Here, X^2 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼
Or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R is an alkylene group having 1 to 5 carbon atoms. )