Silicon tetracarboxylates

Reaction of Carboxylic Acids with Tetrachlorosilane

Voronkov,M;Vlasov,A;Belousova,L;Grigor'eva,O;Vlasova,N

Russ. J. Org. Chem.
Vol.46(3) 2010 pp.318-321
DOI: 10.1134/S1070428010030024

Abstract

Tetrachlorosilane reacted with carboxylic acids RCOOH (R = Me, Bu, t-Bu) to give the corresponding acid chlorides RCOCl in 75–95% yield. The reactions of SiCl4 with trichloroacetic and 2-fluorobenzoic acids (R = Cl3C, 2-FC6H4) occurred more difficultly, presumably for steric reasons, and the yields of the corresponding acid chlorides were 11 and 22%, respectively. Tetrachlorosilane failed to react with stearic acid under analogous conditions. Products of the reactions of SiCl4 with chloroacetic and benzoic acids RCOOH (R = ClCH2, Ph) were tetraacyloxysilanes Si(OCOR)4, and tetrakis(chloroacetoxy)silane was formed in almost quantitative yield. The reaction of SiCl4 with glutaric acid led to the formation of a rubber-like polymeric material with the composition C5H6Cl2O4Si. The effect of pKa values of carboxylic acids on the direction and mechanism of the examined reaction is discussed.

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Silicon Tetrachloride as a Reagent for the Preparation of Acid Chlorides

Montonna,Ralph

J. Am. Chem. Soc.
Vol.49(8.) 1927 pp.2114–2116
DOI: 10.1021/ja01407a043
http://pubs.acs.org/doi/abs/10.1021/ja01407a043

Abstract

The action of silicon tetrachloride on organic acids has hitherto been but slightly investigated. Taurke obtained benzoyl chloride from benzoic acid by means of this reagent adn Rauter prepared butyrl chloride by heating butyric acid with silicon tetrachloride in a sealed tube at 150-160^o. These apparently constitute the only references in the literature.

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Preparation of Substituted Acetoxy Silanes

Schuyten,H;Weaver,J;Reid,J

J. Am. Chem. Soc.
1947, Vol.69(9),  pp.2110–2112
DOI: 10.1021/ja01201a011

Abstract

The use of alkyl chlorosilanes, such as dimethyldichlorosilane, to impart water repellency to cotton textiles has been patented. Unfortunately, the hydrogen chloride produced during the reaction of the silane with adsorbed moisture or cellulosic hydroxyls may seriously weaken the cloth unless elaborate and efficient equipment is employed to avoid this difficulty

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Preparation and Properties of Silicon Tetrapropionate

Lanning,J

J. Am. Chem. Soc.
Vol.75(7) 1953 p.1596
DOI: 10.1021/ja01103a023

Abstract

Silicon tetrapopionate was prepared from silicon tetrachloride and anhydrous sodium propionate. It reacted readily with water and alcohols; was unstable to heat. The thermal decomposition products were characterized. A stiff silica gel containing 69% diethyl ether was prepared. A tertiary alcohol, 3-ethylpentanol-3, and a silicone-like oil were made by reaction of silicon tetrapropionate with ethyl magnesium bromide. This is a new method of preparing tertiary alcohols.

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Silicon Tetrabenzoate

Lanning,J

J. Org. Chem.
1954, Vol.19(7),  1171–1173
DOI: 10.1021/jo01372a025

Abstract

The method for preparing silicon esters from silicon tetrachloride nad sodium salts of organic acids has been used by Schuyten, Weaver and Reid (1) to prepare silicon tetraacetate and by Lanning (2) to prepare silicon tetrapropionate.

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Note on the Action of Oxychlorides of Silicon on Sodium Salts of Fatty Acids

Zanetti,J

J. Am. Chem. Soc.
Vol.34(11) 1912 pp.1598–1600
DOI: 10.1021/ja02212a020
http://pubs.acs.org/doi/abs/10.1021/ja02212a020

Abstract

Thc action of oxych1orides of non-metals on salts of acids has long been used in the synthesis of anhydrides. As far back as 1853, Gerhardt used phosphorus oxychloride on potassium acetate and obtained acetic anhydride, potassium chloride, and potassium phosphate, according to the reaction:

6KOOCCH₃ + POCl₃ = 3KCl + 3(CH₃CO)₂O.

Keepem comming Silane chemistry is the most importing thing in the world for underground chemist from hydroamination to secondary alcohol reduction to alkane at room temperatures. Sooner or later the glory of the Silanes will shine to bright for all to not take notice.