CS226983B1 - Method of preparing organo-silicon esters - Google Patents

Description

The invention relates to a process for the preparation of organosilicon esters from phenyltrichlorosllan, monovalent alcohols, glycols and polyglycol ethers. The new esters are suitable for use in the lubrication technology. They could also find applications in the cosmetics and plastics industries as plasticizers.

Usually, organosilicon esters are prepared using solvents and hydrogen chloride acceptors. However, a novel process has also been developed to eliminate these disadvantageous synthesis conditions.

The esters obtained are very thermo-oxidative and hydrolytically stable and have excellent lubricity. They are applicable over a very wide temperature range and are readily miscible with siloxane, diester, petholester and mineral oils. They dissolve additives perfectly and can therefore be used for the preparation of oils, hydraulic fluids, greases etc.

Their action on butadiene styrene rubber at 120 ° C, 70 h in terms of both swelling volume and weight and hardness is comparable to conventional mineral motor oils.

Process for the preparation of organosilicon esters of the theoretical formula I

V.-O * k

Jut

226 983

226,983 wherein R ₁ to R ^ represents an alkyl group and from 8 to 16 carbon atoms axay have a value of 0.1 to 10, x _{"-CH2-CH2-O- CH2} -CH £ ₂

CI-CH ₂ and ^CH 3 Ji

Ys -QH-CHgO3'3 4 β wherein z has a value of 0 to 3 »by the reaction of phenyltriohlorsilane of formula II

CGH ₅ SiCl ₃ (II) β β alcohols Jednemecnými number of carbon atoms from 8 to 16 and further otylenglykolem, polyethylene glycol ethers, propylene glycol, or mixtures thereof, optionally polypropylonglykolethery ,, according to the invention consists in that the fenyltrichlorsilan reacts with said alcohol at a temperature of 15 to 160 ° C, after completion of the reaction, reduce the hydrogen chloride content by displacement with a stream of nitrogen, then add a solution of sodium hydroxide in one alcohol and distil off and volatile components.

The examples below illustrate embodiments of the invention.

Example 1

Da 6 1 Koller four-necked flasks equipped with a stirrer, thermometer, reflux condenser, addition funnel, arterial bath, and manometer outlet were charged with 212 g diethylonglykelsthor, 200 g triprepylene glycol ether, 320 g alcohol blend containing 85% decanol and 15% dodecanol and stirred while heating the flask, 740 g of phenyltriohorsilane and then 325 g of 2-ethylhexanol were added over an hour. The addition was controlled according to the hydrogen chloride escaping pressure and the temperature was raised to rise to 100-120 ° C in the flask at the end of the addition. Nitrogen was then introduced into the bottom of the flask and the acidity of the flask was reduced to 0.08 mg KOH / g with a nitrogen stream over a period of 30 to 60 minutes while stirring and heating the flask to 110-120 ° C. The calculated amount of saturated sodium hydroxide solution of 2-ethylhexanol was then added to the flask with stirring. The contents of the flask were then transferred to a vacuum distillation apparatus and the volatiles were distilled off at 1400 Pa and a boiling point of 220 ° C. After cooling, the distillation residue was filtered through paper to give 1108 g of a clear, yellow ester with an acid number of 0.04 mg KOH / g, n ^ ² ^ 1.4862, flash point 217 ° C, combustion temperature 249 ° C, pour point -43 ° C, viscosity at

100 ° C 20.99 mm ² .s @ ² at 50 ° C 88.39 mm ² .e "^ ·, at -20 ° G 12842 mm ² .s" ^, viscosity index 187.

Example 2

Using the procedure and apparatus of Example 1, 270 g of dipropylene glycol ether were treated,

150 g of trletylene glycolother, 320 g of the alcohol mixture of Example 1, 740 g of phenyltriohorsilane and 325 g of 2-ethylhexanol. ^By distilling off at 1440 Pa to a boiling point of 226 ° C, 1072 g of a distillation residue was obtained which was clear, yellow, having an acid number of 0.03 mgXOH / g, a flash point of 227 ° C, a combustion temperature of 253 ° C, a freezing point. -43 ®C, viscosity at 100 ° C 14.28 mm ² .s ¹ , at 50 ° C 37.5.6 rnnAs “ ¹ , at -20 ° C 8978 ηΛβ ¹ .

Example 3

As in Example 1, an ester was synthesized from 14 g of dipropylene glycol ether, 150 g of trlethylene glycolother, 320 g of the alcohol mixture of Example 1, 740 g of phenyltriohorsilane and 325 g of 2-ethylhexanol. Distillation at 1500 Pa to a boiling point of 242 ° C was obtained

226 983

1024 g of clear, yellow ester, β acid number 0,06 mg KOH / g, n ^ ² ^ 1,4820, flash point

223 ®C, burning temperature 258 ®C, pour point -55 ° S, viscosity at 100 ®C 10.32 mm ² .s ” ¹ , at 50 ®G 37» 56 mm ² .a ^-1 , at -20 ° C 2889 mm ² .a ^-1 , at -40 ° C 38882 "m ^2. "" ¹ , viscosity index 185.

Claims (1)

pSbdbžtyísíiezu HER Process for the preparation of organosilicon esters of the theoretical formula (1) γ ₅ PT ^C v6 ^H 5 ^x si-ox- z -Si-O-Y- dR L ^OR 2 J X ^ 6 ^H 5 -SiOR / STEED. (I) wherein R ^ to R ^ represents an alkyl group having 8 16 carbon atoms EŽ axay have a value of 0.1 to 10, Σ = -CH ₂ - CHgO - CHgO- [CH - CHgOz Υ -CH-CHgO- [CH-CHgO-1 ° Η ₃ L ^C * 3 J z wherein z has a value of 0 to 3 »by the reaction of phenyltrichlorosilane of formula II c ₆ h _{5 with 3} ' and ethylene glycol, polyethylene glycol ethers, propylene glycol or polypropylene glycol ethers or a mixture thereof, characterized in that phenyltrichlorosilane is reacted with said alcohols at a temperature of 15 DEG to 160 DEG C., after completion of the reaction, the hydrogen chloride content is reduced by displacement with a nitrogen stream. of monovalent alcohol and the volatiles are distilled off.