66548-22-9

Usage

Uses

Used in Silicone Elastomers and Resins Production:
BIS(T-BUTYLDIMETHYLSILOXY)ETHANE is used as a crosslinking agent for enhancing the mechanical properties and heat resistance of silicone materials, contributing to the production of durable and high-performance silicone elastomers and resins.
Used in Lubricant Additives:
BIS(T-BUTYLDIMETHYLSILOXY)ETHANE is utilized as a lubricant additive to improve the performance and efficiency of lubricants, providing better protection and reducing friction in various mechanical applications.
Used in Surface Treatment Agents:
BIS(T-BUTYLDIMETHYLSILOXY)ETHANE is employed as a surface treatment agent for various materials, offering improved adhesion, durability, and resistance to environmental factors.
Used in Waterproof Coatings and Sealants:
Leveraging its water repellent properties, BIS(T-BUTYLDIMETHYLSILOXY)ETHANE is used in the formulation of waterproof coatings and sealants, ensuring protection against moisture and enhancing the longevity of treated surfaces.

Upstream product

• 107-21-1 ethylene glycol 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Relevant academic research and scientific papers

Synthesis method of 1, 2-bis (alkyl-siloxy) ethane

The invention provides a synthesis method of 1, 2-bis (alkyl-siloxy) ethane, and belongs to the technical field of battery electrolytic solution additives. The method comprises the following steps: adding dichloromethane and ethylene glycol into a reaction kettle, cooling to 15 DEG C or below, adding imidazole, continuously cooling to -15 DEG C or below, starting to dropwise add vinyl dimethyl chlorosilane or tert-butyl dimethyl chlorosilane or trimethylchlorosilane, controlling the temperature in the dropwise adding process to range from -15 DEG C to -25 DEG C, after dropwise adding is completed for 1.8-2.2 h, washing the system with water, carrying out liquid separation, drying, carrying out suction filtration, collecting dichloromethane under reduced pressure, and rectifying to obtain 1, 2-bis (dimethyl vinyl siloxy) ethane or 1, 2-bis (tert-butyl dimethyl siloxy) ethane or 1, 2-bis (trimethyl siloxy) ethane. The synthesis method is simple, and the yield of the synthesized product is high.

Preparation method of everolimus intermediate

The invention discloses a preparation method of an everolimus intermediate. The preparation method comprises the following steps: reacting ethylene glycol and tert-butyldimethylsilyl chloride in inert solvents such as dichloromethane at the temperature of 35 DEG C below zero to 25 DEG C below zero in the presence of organic base to obtain 2-(tert-dimethylsiloxy)ethyl alcohol; reacting the 2-(tert-dimethylsiloxy)ethyl alcohol and trifluoromethanesulfonic anhydride in the presence of the organic base to obtain trifluoromethanesulfonic acid 2-(tert-dimethylsiloxy)ethyl ester. According to the method disclosed by the invention, the generation of a disubstituted by-product can be greatly reduced, and further a monosubstituted product 2-(tert-dimethylsiloxy) ethyl alcohol with relatively-high purity and yield is obtained.

Silicon-29 NMR spectra of tert-butyldimethylsilyl and trimethylsilyl derivatives of some non-rigid diols

29Si NMR spectra of trimethylsilyl (TMS) and tert-butyldimethylsilyl (TBDMS) derivatives of selected diols were measured under standardized conditions (i.e., in diluted CDCl3 solutions). Application of the recently reported correlation between the chemical shifts in TMS and TBDMS derivatives revealed considerable and systematic deviations which exceeded experimental errors and error estimates from the correlation. Two possible explanations of the deviations are considered: interaction between the two bulky substituent groups and invalidity of the reported correlation for simple hydroxy derivatives. An independent study of analogous derivatives of monohydroxy compounds has shown that the linear correlation holds but the slope and intercept are significantly different from those reported previously on the basis of a study of amino acid derivatives. The data obtained for the diol derivatives fit the new correlation very well and no indication of an interaction between the bulky TBDMS groups was noticed. However, deviations do occur in branched diol derivatives in which branching reduces accessibility of the oxygen atoms surface to associate with proton donors. The largest deviation was found when intramolecular hydrogen bond was formed.

Synthesis of vicinal glycols

Relatively low molecular weight primary alcohols are coupled to form relatively higher molecular weight vicinal glycols in which a trialkylsilyl protecting group is employed on the hydroxyl position of said low molecular weight primary alcohol during said coupling reaction. BACKGROUND OF THE INVENTION This invention relates to the production of vicinal glycols from starting molecules having fewer carbon atoms such as, for example, the preparation of ethylene glycol and glycerol from methanol. More particularly, this invention is concerned with the coupling of relatively low molecular weight or short chain primary alcohols to form relatively higher molecular weight or vicinal glycols by employing a trialkylsilyl protecting group on the hydroxyl position of said low molecular weight primary alcohol. In view of the fuel and mineral shortages facing the world, particularly petroleum feedstocks, there is a scarcity of vital building blocks such as ethylene and propylene used to synthesize many modern chemical entities. Consequently, alternate carbon sources for the chemical industry's basic organic chemicals must be developed for future needs from either coal or single carbon molecules such as carbon monoxide, carbon dioxide or methanol. Two major products produced from petroleum-derived feedstocks such as ethylene and propylene are, respectively, ethylene glycol and glycerol. Ethylene glycol is widely used for antifreeze and in numerous nonantifreeze outlets, including cellophane, polyester fibers and films, and polyglycols. Glycerol finds wide use in cosmetics, dentifrices, drugs and pharmaceuticals, alkyd resins, cellophane and in tobacco as a humectant and in the manufacture of plasticizers for cellulose cigarette filters. In the production of ethylene glycol, ethylene oxide is usually first prepared by direct oxidation of ethylene or by the chlorohydrin synthesis and the ethylene oxide is then reacted with water to make ethylene glycol. Although glycerol is a natural by-product of soap manufacture, a significant quantity of synthetic glycerin also is prepared from propylene. One such process involves the chlorination of propylene to allyl chloride, conversion into epichlorohydrin, and thence into glycerin. Another process involves oxidation of propylene to acrolein, conversion into allyl alcohol, then reaction with hydrogen peroxide to yield glycerin. In a third process, propylene oxide is catalytically converted into allyl alcohol, which is treated with peracetic acid to yield glycidol. Glycidol then combines with water to make glycerin. An improved method of producing vicinal glycols such as, for example, ethylene glycol and glycerol, from shorter chain molecules such as, for example, methanol, instead of employing petroleum-derived feedstocks such as ethylene and propylene, would provide significant advantages over prior methods of production. BRIEF DESCRIPTION OF THE INVENTION In accordance with the present invention, vicinal glycols are produced from starting molecules having fewer carbon atoms. In particular, relatively low molecular weight or short chain primary alcohols are coupled to form relatively higher molecular weight vicinal glycols by employing a trialkylsilyl protecting group on the hydroxyl position of said low molecular weight primary alcohol. As used herein, the term trialkylsilyl means a group containing a silicon atom bonded to three alkyl radicals, any of which can be the same as, or different than, any other. The process of this invention involves the oxidative or dehydrogenative coupling of the shorter chain primary alcohol without over-oxidation to undesirable by-products, for example, aldehydes. The initial dehydrogenation of the shorter chain primary alcohol is thus made to take place on the carbon rather than the hydroxyl group by using the trialkylsilyl blocking group on the hydroxyl. Alcoholysis of the coupled reaction product then readily yields the desired vicinal glycol. The coupling reaction of this invention is briefly illustrated by the preparation of ethylene glycol and glycerol from methanol. In order to produce ethylene glycol, two trialkylsilyl blocked methanol molecules are reacted to form 1,2-bis(trialkylsiloxy)ethane which, upon methanolysis, yields ethylene glycol. In order to produce glycerol, three trialkylsilyl blocked methanol molecules are reacted to form 1,2,3-tris(trialkylsiloxy)propane which, upon methanolysis, yields glycerol. The above process has definite advantages over the direct coupling of methanol to ethylene glycol and glycerol. This process has a higher selectivity for ethylene glycol and glycerol and less by-product is produced. That the direct coupling of methanol undesirably leads to a substantial amount of formaldehyde is seen from the work of Schwetlich et al, Angew. Chem. 72, 779 (1960); and Ladygin and Saraeva, Kinetics and Catalysis 6, 189-95 (1965) and 7, 832-39 (1966).