DE1108365B - High pressure lubricating oils - Google Patents

Description

It has been found that reaction products of hexachlorocyclopentadiene and dienophilic monocarboxylic acid esters are particularly suitable as high-pressure lubricating oils. You can use the reaction products mentioned use as such as high pressure lubricating oils, but they can also be used as lubricating oils based on hydrocarbons, good high-pressure lubricating oils are obtained.

The dienophilic monocarboxylic acid esters used for the reaction with hexachlorocyclopentadiene are vinyl esters into consideration, e.g. B. vinyl acetate, vinyl propionate, vinyl butyroate, vinyl hexanoate, vinyl 2-ethylhexanoate, Vinyl oleate, vinyl palmitate.

The esters of the "," - unsaturated are also suitable Carboxylic acids, ζ. B. n-butyl acrylate, i-butyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, lauryl acrylate, Butyl crotonate.

The additives according to the invention can be added to lubricating oils in a known manner, for. B. manufacture in such a way that one first of all «, ^ - unsaturated monocarboxylic acids Reacts with hexachlorocyclopentadiene and then the esterification of the products obtained in at a special stage.

The high content of chlorine, which is very firmly bound in the reaction products mentioned, is not split off as a lubricating oil or lubricating oil additive and makes the reaction products flame-retardant and when mixed with hydrocarbon oils increase the flash point of these oils. Already the

Applicant:

Aniline & Soda Factory in Baden

Corporation,

Ludwigshafen / Rhine

Dr. Adolf Hrubesch, Ludwigshafen / Rhine,

and Dr. Herbert Friederich, Worms,

have been named as inventors

In many cases, an addition of 0.5 to 10 percent by weight is sufficient to make lubricating oils based on hydrocarbons to improve significantly. But you can also use large amounts, e.g. B. 15, 20, 30 percent by weight and add more.

It is already known that reaction products of hexachlorocyclopentadiene with dicarboxylic acid esters to be used as additives to lubricating oils. However, these reaction products are those from hexachlorocyclopentadiene and monocarboxylic acid esters, as in the following comparative experiments demonstrate.

Amount added More specific
wear and tear Entry into the
Wear high position Added fabric in one
commercially available
ίτπιηππΐ τιΐτ · per horsepower hour in load level VJl UIlU (Jl 1 Ul
High pressure gear oils 0.15 mg to in 1% Load level 10 11 1. Di-n-butyl ester of dichloroendomethylenetetrachloro 0.22 mg of cyclohexenedicarboxylic acid 4% Load level 3 to 11 11 0.17 mg of 1% Load level 3 to 11 11 2. Di-iso-butyl ester of dichloroendomethylene tetra- 0.13 mg of chlorocyclohexene dicarboxylic acid 4% Load level 3 to 12 12th 0.06 mg of 1% Load level 3 to 12 over 12 3. Isobutyl ester of dichloroendomethylenetetrachloro 0.04 mg of cyclohexene monocarboxylic acid 4% Load level 3 to 12 over 12

109 610/400

It is also proposed to use reaction products of hexachlorocyclopentadiene with lubricating oils to add ethylenically or acetylenically unsaturated compounds, these being unsaturated Compounds but no carboxylic acid, ester or anhydride group, but at least one chlorine or Bromine atom included. These compounds are therefore not identical to those used according to the invention.

The parts mentioned in the following examples are parts by weight.

example 1

The mixture is heated 374 parts hexachlorocyclopentadiene (96 ^o / oig) in a stirred flask with 98 parts by weight of acrylic acid (98%) slowly to 150 ⁰ C. and left for 4 hours at this temperature. Then 10 parts of p-toluenesulphonic acid, 50 parts of xylene and 320 parts of C ₈ H ₁₀ initial fatty alcohol are added. In a few hours, the water is separated off via a separator, and the flow is distilled off at an internal temperature of 200 ° C. in a normal water jet vacuum. In the following high-vacuum distillation _O76 obtained 520 parts of a yellowish oil having a bp. 185-260 ⁰ C.

If you add 4 percent by weight of this compound to an SAE-20 test oil, you get in the Niemann test machine a spec. Wear of 0.08 mg per horsepower hour; the Almen-Wieland machine shows a load capacity of 1550 to 1600 kg; the diameter of the wear cap in the four-ball apparatus is 2.7 mm.

If the compound obtained is used as such as a lubricating oil, the wear values are in Niemann testing machine at 0.06mg per horsepower hour, the values in the Almen-Wieland machine at 1900 to 1950 kg and the diameter of the wear cap in the four-ball apparatus is 2.4 mm.

Example 2

In the same way as in Example 1, the n-butyl ester, the lauryl ester and the octadecyl ester can be used of acrylic acid to add to hexachlorocyclopentadiene. These reaction products can, as in Example 1 be used.

It is sometimes advantageous for the production of lubricating oils with very high viscosity, moreover ίο Polymers of the acrylic ester, methacrylic ester, polyisobutylene or add styrene series.

Example 3

The mixture is heated 1,100 parts of hexachlorocyclopentadiene in stirred flasks at 160 ° C, then slowly added dropwise 400 parts Vinylpropinonat added and the reaction mixture maintained for 3 hours at 160 to 170 ° C. Vacuum distillation is obtained therefrom in almost quantitative yield the adduct C ₁₀ H ₈ OCl ₆ ( Molecular weight 357) with b.p. ₁₅ of 183 ° C, which is a good high-pressure lubricating oil.

Claims (2)

PATENT CLAIMS: 1. Use of reaction products of hexachlorocyclopentadiene with dienophilic monocarboxylic acid esters as high pressure lubricating oils. 2. High pressure lubricating oils, consisting of lubricating oils based on hydrocarbons and an addition of reaction products according to claim 1. Considered publications:
U.S. Patent Nos. 2,622,096, 2,771,423, 2,773,832. Legacy Patents Considered:
German Patent No. 1 075 775.