CS231232B1 - Organosilicon esters and process for their preparation - Google Patents

Abstract

Organosilicon esters of the theoretical composition I6 5 R.O-Si-X ’ I 0Ro ‘ CH-, " l J I65 -Si-X i - Si-X -Si-OR. 1 4 1CH3 0.9 | c6H5 θ,’ “3 and their preparation method is created by reacting tripropylene glycol ether with a mixture of dimethyldichlorosilane and diphenyldichlorosilane, then the resulting mixture is reacted with phenyltrichlorosilane and a mixture of decanol and dodecanol and the esterification is completed with 2-ethylhexanol. After the reaction is complete, a solution of sodium hydroxide in 2-ethylhexanol is added and the volatile components are distilled off. Stable esters are used in a wide temperature range in combination with siloxane, diester, polyolester and mineral oils for lubrication purposes.

Description

(54) Organosilicon esters and method of their preparation

Organosilicon esters of theoretical composition

I ^{6 5} RO-Si-X ' I

0R _about

' CH-, l ^J I ⁶⁵ -Si-X i - Si-X -Si-OR. 1 ⁴ 1 CH ₃ 0.9 | ^c 6 ^H 5 θ,’ “3

and the method of their preparation is created by reacting tripropylene glycol ether with a mixture of dimethyldichlorosilane and diphenyldichlorosilane, then the resulting mixture is reacted with phenyltrichlorosilane and a mixture of decanol and dodecanol and the esterification is completed with 2-ethylhexanol after the reaction is complete a solution of sodium hydroxide in 2-ethylhexanol is added and the volatile components are distilled off.

Stable esters are used over a wide temperature range in combination with siloxane, diester, polyolester and mineral oils for lubrication purposes.

23,232

The invention relates to organosilicon compounds and a method for their preparation from dimethyldichlorosilane, diphenyldichlorosilane, polyethylene glycol ethers, polypropylene glycol ethers, phenyltrichlorosilane and monohydric alcohols.

The issue of preparation of organosilicon esters generally falls under the esterification methods of halosilanes. The conditions of reactions of alcohols with chlorosilanes are the subject of a number of publications (OrganoSilicon compounds, vol. I Academia, Prague 1965, Ladenburg. Ber. 6, 379/1983).

A review of various methods of esterification of halosilanes is given in Chem. Rev. Azh» 97 (1947).

For the purposes of lubrication technology, many types of oils have been tested, from mineral oils, to esters of organic alcohols with mono- or dicarboxylic acids, to organosilicon compounds. Organosilicon esters are usually prepared using solvents and hydrogen chloride acceptors. Amines such as pyridine, aniline, triethylamine, etc. are usually used as acceptors.

When they are used, a large amount of bulky salt is formed, as a result of which it is necessary to use a lot of solvents to enable the mixture to be volatile. The process is therefore unsuitable for industrial practice. Therefore, new types of substances and more advantageous processes for their preparation were sought, for example those given in Czechoslovak patent 231 224 and Czechoslovak patent 228 443 and elsewhere. It has now been found that organosilicon esters according to the invention, which are new and have not yet been described in the literature, are suitable for the purposes of lubrication technology.

These are organosilicon compounds of theoretical composition

C,H _r I ™3 ^C A I CA 1 ⁵ R,O~ - Si -X I You X - You are -X 1 - Yes - OR, 4 I 0Η ₉ to 0.9 C,H _R 6 5 OJ . ^0R 3

where

X k, and K, ' 3 denotes a residue derived from tripropylene glycol ether denotes alkyl and 8 carbon atoms, denotes a mixture of alkyls containing 85% alkyls with 10 carbon atoms and 15% alkyls with 12 carbon atoms, which are prepared according to the invention by reacting tripropylene glycol ether with a mixture of 0.9 molar parts of dimethyldichlorosilane and 0.1 molar parts of diphenyldichlorosilane and a mixture of decanol and dodecanol in a ratio of 85:15 and the esterification is completed with 2-ethylhexanol at a temperature of 15 to .60 °G, after the reaction is complete, a solution of sodium hydroxide in the 2-ethylhexanol used is added and the volatile components are distilled off.

The example below illustrates an embodiment of the invention.

Example of execution

129 g of tripropylene glycol ether was introduced into a 6 l Keller flask equipped with a stirrer, thermometer, reflux condenser, addition funnel, heating bath and outlet pipe with manometer. A mixture of 25 g of diphenyldichlorosilane and 116 g of dimethyldichlorosilane was added to the flask over 1 h, while stirring and simultaneously heating the flask, then 320 g of a mixture containing 85% decanol and 15% dodecanol, 423 g of phenyltrichlorosilane and 286 g of 2-ethylhexanol. The addition was controlled according to the pressure of the escaping hydrogen chloride and the temperature was increased so that by the end of the addition in the flask it reached 100 to 120 °C. After all the 2-ethylhexanol had been added, a stream of nitrogen was introduced to the bottom of the flask through a tube and, while stirring and heating the flask to 110 to 120 °C, the acidity content in the flask was reduced by the stream of nitrogen within 30 to 60 minutes to an acidity number of 0.05 mg KOH/g and a salt content of 0.05 mg KOH/g. Then, the calculated amount of a saturated solution of sodium hydroxide in 2-ethylhexanol was added to the flask with stirring. The contents of the flask were then passed into a distillation apparatus and the excess alcohol was distilled off at a pressure of 2,000 Pa to a boiling point of 210 °C.

After cooling, the distillation residue was filtered through paper, yielding 944 g of clear, light yellow liquid with an acid number of 0.03 mg KOH/g, n^ 1.4760, with a flash point of 225 °C, a burning point of 261 °C, a freezing point of -55 °C, a viscosity at 200 °C of 4.54 mm ^{2 *} .s ^- '; a viscosity at 150 °C of 7.47 mm ² .s'^, a viscosity at 100 °C of 16.39 mm ² .s ^- \ a viscosity at -20 °C of 4,565 mm ² .s~\ with a viscosity index of 206 and a moisture content at 80% relative humidity in about 90 h of 0.22% by weight.

An ester of the chemical composition indicated was prepared in the above-mentioned manner, the symbols having the meanings indicated above.

where general

SUBJECT OF THE INVENTION

Claims (2)

RjO Organosilicon esters of theoretical composition CUH _r 1 ^J gh ₃ ^{C6H5 ​} °ό ^H 5 You are -X - Yes | - X - You X - Si - OR, \ ⁴ <\J —o 1 CH. 3 0.9 ^6 ^H 5 0.1 OB. ’ 3 where X R1 represents a residue derived from tripropylene glycol ether and R3 represents an alkyl with 8 carbon atoms and R4 represents a mixture of alkyls containing 85% alkyls with 10 carbon atoms and 15% alkyls with 12 carbon atoms. 2. A method for preparing organosilicon esters according to item 1, characterized in that tripropylene glycol ether is reacted with a mixture of 0.9 molar parts of dimethyldichlorosilane and 0.1 molar part of diphenyldichlorosilane, then it is reacted with 2 molar parts of phenyltrichlorosilane and a mixture of decanol and dodecanol in a ratio of 85:15 and the esterification is completed with 2-ethylhexanol at a temperature of 15 to 160 °C, after the reaction is complete, a solution of sodium hydroxide in 2-ethylhexanol is added and the volatile components are distilled off.