Organosilicon ethers of ricinoleic acid
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Organosilicon ethers of ricinoleic acid* N. P. Shapkin, I. G. Khalchenko, N. V. Maslova, V. V. Gribova, and V. G. Savchenko Far Eastern Federal University, 10 pos. Ayaks, island Russian, 690922 Primorsky Krai, Russian Federation. E-mail: [email protected] Interaction of vinyl trichlorosilane with sodium salt of ricinoleic acid is investigated. It is established that the composition and structure of silicon-containing ethers depends on the content of crystallization water in sodium ricinoleate, and the concentration and nature of solvent. Thus, in the case of a mixture of absolute alcohol with ether and low content of crystallization water, the reaction proceeds by hydroxyl of alcohol to form salt-like compounds containing silicon. In the case of a salt with a high content of crystallization water, the reaction proceeds along two reaction centers with the formation of ether and ester simultaneously. The composition and structure of the obtained compounds were established using elemental analysis, IR, 1H, 13C NMR spectroscopy, and gel chromatography. It is proposed to use prepared organosilicon ethers of ricinoleic acid as additives to motor oils instead of castor oil. Key words: castor oil, sodium ricinoleate, organosilicon ether of ricinoleic acid.
Castor oil is a renewable and biodegradable product. It is a part of high-quality lubricants1 and creams2 and is also used to produce interpenetrating cross-linked polymers.3,4 In this regard, the scientific and practical interest to ricinoleic acid derivatives is increasing.5.6 So, the production of interpenetrating cross-linked polymers based on castor oil, polyurethane and polymethyl methacrylate was studied.7 The polymerization process was studied by IR spectroscopy. Nanocomposite piezoelectrical materails were obtained based on these polymers and barium titanate. Their morphology, as well as thermoelectric and mechanical properties, were studied. High molecular weight thermoplastic biodegradable polymer was synthesized upon carbonylation of castor oil with carbon dioxide in the presence of a catalyst (pyridine : octacarbonyl dicobalt) at high pressure and temperature.8 Polymer structure was investigated by gel permeation chromatography (GPC) and 13C NMR spectroscopy. The influence of a number of organic solvents and inorganic compounds on the enzymatic hydrolysis of castor oil was examined.9 It was established that the maximum depth of hydrolysis is achieved in a presence of calcium ions (С = 0.02 mmol L–1), and the introduction of various organic solvents has an ambiguous effect. New methods for the synthesis of 3R-hydroxynonanoic acid and its ester derivatives by ozonolytic cleavage * Based on the materials of the XXI Mendeleev Congress on General and Applied Chemistry (September 9—13, 2019, St. Petersburg, Russia).
of castor oil in alcohol solutions and acetic acid were reported.10 Transesterification of various vegetable oils by methanol was investigated by IR spectroscopy. It is known that this technology allows to manufacture an "ecodiesel".11 Note that
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