CS228475B1 - Organosilicon esters and process for their preparation - Google Patents

Abstract

Organosilicon esters of the general formula I O(CH2CH2O)zR1 Z C6H5-nXnSi-OR2 \ or3 where X = Cl, Br, η = 1 to 5, Ri alkyl containing 1 to 4 carbon atoms, Rz, R3 are the same or different and denote alkyl with 8 to 20 carbon atoms, z = 1 to 3, and a method for their preparation by reacting halophenyltrichlorosilane with polyethylene glycol alkyl ether and monohydric alcohols at a temperature of 15 to 160 °C, after the reaction is complete, the hydrogen chloride content is reduced by displacement with a stream of nitrogen, then a solution of sodium hydroxide in the alcohol used is added and the volatile components are distilled off. The new esters are high-quality lubricating components for use in a wide temperature range, well miscible with siloxane, diester and other oils.

Description

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

Typically, organosilicon esters are prepared using solvents and hydrogen chloride acceptors. As chloracceptors, amines such as pyridine, aniline, triethylamine and the like are generally used. With the use of these acceptors, a large amount of the hydrochloride of the base used is a ballast substance. The process is therefore unacceptable for industrial practice because the amine, excess alcohol and solvent used to dissolve the hydrochloride would have to be recovered and returned to production. For new types of esters, however, a new process eliminating these disadvantageous synthesis conditions has been developed.

The novel esters are useful over a very wide temperature range and are readily miscible with siloxane, diester, polyester and mineral oils. They dissolve additives perfectly and can therefore be used for the preparation of synthetic oils, hydraulic fluids, greases etc.

Organosilicate esters of general formula I 0 (ΟΗ ₂ ΟΗ ₂ 0) _ζ Κ!

/

C 1 H 8 -nX 11 Si-OR _{2 '} or ₃ (I) wherein

X = Cl, Br, η = 1 to 5,

R1 alkyl having 1 to 4 carbon atoms,

R 2, R 3 are the same or different and denote alkyl having 8 to 20 carbon atoms, z = 1 to 3, formed by the reaction of halophenyltrichlorosilanes of formula II

C ₆ H ₅ _ _n X _n SiCl ₃ (II) wherein X and n are as defined above, with alkyl polyglycol ethers and monohydric alcohols are prepared according to the invention so that halogenfenyltrichlorsilan reacting with said polyethylenglykolalkyletherem and alcohols at 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 the alcohol used and distill off the volatiles.

The example below illustrates an embodiment of the invention.

Exemplary embodiment

To 61 Keller four-necked flasks equipped with a stirrer, thermometer, reflux condenser, admission funnel, heating bath, and manometer drain line were added 243 g of butyldiethylene glycol ether, 240 g of a mixture containing 85% decanol and 15% dodecanol. 369 g of chlorophenyltrichlorosllan and 260 g of 2-ethylhexanol were added for one hour. 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. Upon addition of 2-ethylhexanol, a nitrogen stream was introduced into the bottom of the flask and the acid content of the flask was reduced to an acid number of 0.12 mg KOH / g while stirring and heating the flask to 100-120 ^° C. A calculated amount of saturated solution of sodium hydroxide in 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 excess alcohol distilled off at 2000 Pa to a boiling point of 133 ° C. After cooling, the distillation residue was filtered through paper to obtain 740 g of a clear, yellowish liquid with an acid number of 0.07 n _D ²⁵ = 1.4717, a flash point of 212 ° C, a combustion temperature of 231 ° C, a freezing point of -68 ° C, viscosity at 100 ° C 3,55 mm ² . s ^-1 , at 50 ° C 10.00 mm ² . s “*, at –20 ° C 285 mm ² .s ^-1 , at - 40 ° C 1984 mm ² .s ^-1 , viscosity index 153. Liquid action on elastomer with butadiene styrene rubber at 120 ° C for swelling by volume, weight and the hardness variation is slightly higher than the effect of mineral motor oil.

The liquid at 80% relative humidity solidified at 90 hours by 0.49% weight gain and only 0.11 percent after addition of the antioxidant additive.

Claims (2)

SUBJECT 1. Organosilicon esters of the general formula I O (CH ₂ CH ₂ OhR! / C ₆ H _{5 -n} X _n Si-OR ₃ or ₃ (I) wherein X = Cl, Br, n = 1 to 5, R 1 alkyl of 1 to 4 carbon atoms of the invention R 2, R 3 are the same or different and denote alkyl having 8 to 20 carbon atoms, z = 1 to 3. 2. A process for the preparation of organosilicon esters according to item 1 by reacting an alkylpolyglycol ether with monovalent alcohols, characterized in that halophenyltrichlorosilane is reacted with said polyethylene glycol alkyl ether and alcohols at a temperature of 15-160 ° C, after completion of the reaction sodium hydroxide in the alcohol used and the volatiles were distilled off.