CS230323B1 - Organo-silicon esters and method of preparing same - Google Patents

Description

The invention relates to a process for the preparation of organosilicon esters from halophenyltrichlorosilanes and polyethylene glycol alkyl ethers suitable for the lubrication technique.

The ever-increasing demands on the parameters of equipment, machines and engines, especially aircraft engines, have led to increased requirements for lubricating oils. Many types of oils have been tried for the purpose of lubrication technology, from mineral to esters of organic alcohols with mono- or dicarboxylic acids to organosilicon compounds. The disadvantageous properties of the methyl and phenylsiloxanes themselves have been eliminated by the lower alkyl alkoxysilanes found later. It has now been found that esters containing aryl, optionally haloaryl and alkoxy groups with a larger substituent can be synthesized. This finding has been used in the preparation of the novel organosilicon esters of the invention. The aforementioned organosilicon esters are prepared conventionally using solvents and hydrogen chloride acceptors. Amines such as pyridine, aniline, triethylamine and the like are generally used as acceptors. Using these acceptors, a large amount of the hydrochloride of the base used is a ballast substance. The procedure is unacceptable for industrial practice. A novel process has been developed for novel types of esters, eliminating these disadvantageous synthesis conditions.

The novel esters of formula (I) of the present invention are useful over a very wide temperature range and are readily miscible with siloxane, diester, polyolester and mineral oils. They excellently dissolve additives and can therefore be used for the preparation of synthetic oils, hydraulic fluids, greases, etc. Organosilicate esters of formula I

O (CH 2 CH 2 O) _from R /

C6H5. _n X _n Si-O (CH 2 CH 2 O) _from R (I) \

O (CH 2 CH 2 O) _z R where X = Cl, Br η = 1 to 5

R = C1-C4 alkyl of 1 to 3 are prepared according to the invention by reacting a halophenyltrichlorosilane of formula II

C6H5. _n X _n SiCl 3 (II)

Where X = Cl, Br η = 1 to 5 with alkyl polyglycol ethers at 15 to 160 degrees Celsius, after completion of the reaction, reduce the hydrogen chloride content by displacement with a stream of nitrogen, then add the sodium hydroxide solution in the alcohol used and distil off the volatiles. The example below illustrates an embodiment of the invention.

Exemplary embodiment

To a 6 L Keller four-necked flask equipped with a stirrer, thermometer, reflux condenser, admission funnel, heating bath, and manometer drain line, 881 g of butyldiethylene glycol ether was charged, and 369 g of chlorophenyltrichlorosilane was charged over 1 hour with stirring. The addition was controlled according to the hydrogen chloride escaping pressure, and the temperature was raised to reach 100-120 ° C in the flask at the end of the addition. After all chlorophenyltrichlorosilane was allowed to flow, a stream of nitrogen was introduced into the bottom of the flask through the tube, stirring and heating the flask to 110 to 110 ° C.

At 120 ° C, the acidity of the flask was reduced to a acid value of 0.04 mg KOH / g over 30 to 60 minutes with a nitrogen stream. A calculated amount of saturated sodium hydroxide in butyldiethylene glycol ether was then added to the flask with stirring. The contents of the flask were then transferred to a vacuum distillation apparatus and the excess alcohol distilled off at 2000 Pa to a boiling point of 150 ° C. After cooling, the distillation residue was filtered through paper to give 880 g of a clear, yellowish liquid with an acid number of 0.04, n _D ^{25 of} 1.4763, a viscosity at 100 ° C of 3.08 mm ² . s ^-1 , at 50 ° C, 7.94 mm ² . s ^-1 , at -20 ° C 178 mm ² . s ^-1 -40 ° C 1258 mm ² .s ^_1 viscous index 172, flash point 165 ° C burning temperature of 204 ° C, pour point -70 ° C.

The effect of the liquid on butadiene styrene rubber at 120 ° C in terms of bulk, weight and hardness swelling is weaker than that of mineral motor oil.

The liquid at 80% relative humidity had a weight gain of 1.55% at 90 hours and only 0.83% after addition of the antioxidant additive.

Claims (2)

Subject 1. Organosilicate esters of formula I O (CH 2 CH 2 O) _Z R / C6H5-nXnSi-O (CH2CH2O) _Z R (I) \ O (CH 2 Cl 2 O) _Z R wherein X = Cl, Br n = 1 to 5 R = C 1 -C 4 alkyl z = 1 to 3 2. A process for the preparation of organosilicon esVYNALEZ of teres according to claim 1, characterized in that the halophenyltrichlorosilane of the formula II: C ₆ H5. _n X _n Si 3 (II) where X = Cl, Br n = 1 to 5 is reacted with alkyl polyglycol ethers at 15 to 160 ° C, after completion of the reaction reduce the hydrogen chloride content by displacement with a stream of nitrogen, then add sodium hydroxide solution in the used alcohol, and the volatiles are distilled off.