ISOMERS OF 3-CHLORO-N,N,N-TRIS(3-METHYLBUTYL)PROP-2-EN-1-AMMINIUM CHLORIDE AS COMPLEX OIL AND GAS FIELD REAGENTS WITH ANTIHYDRATE, ANTICORROSIVE AND BACTERICIDAL ACTION

One of the most promising classes of low-dosage hydrate inhibitors is anti-agglomerants, which are favorably characterized by high efficacy at very low working concentrations (0.1-0.5%). We have investigated the possibility of creating new anti-agglomerants with enhanced anticorrosive and bactericidal properties based on the quaternization of tris(3-methylbutyl)amine with (E)- and (Z)-1,3-dichloropropene isomers. It is well known that compounds with a 3-chloroprop-2-enyl fragment have a pronounced anticorrosive and bactericidal action. Thus, the presence in the quaternization products of isopentyl groups and 3-chloroprop-2-enyl fragments that are optimal for preventing agglomeration of the gas hydrates can contribute to the complex antihydrate, anticorrosive and bactericidal activity of these compounds. An attempt to conduct the alkylation of tris(3-methylbutyl)amine with (E)-1,3-dichloropropene in standard solvent – boiling ethanol for 3 days leads to a low yield of the target quaternary salt. Using chromatography-mass spectrometry, it was established that there are significant amounts of by-products in the reaction mixture, which are formed as a result of various nucleophilic substitutions and elimination reactions. Alkylation of tris(3-methylbutyl)amine in boiling acetonitrile proceeds faster and more selectively in 80% yield of (E)-3-chloro-N,N,N-tris(3-methylbutyl)prop-2-en-1-amminium chloride in 20 h. A quaternization with (Z)-1,3-dichlopropene under the same conditions gives an isomeric quaternary salt with a similar yield. The alkylation of tris(3-methylbutyl)amine with isomers of 1,3-dichloropropene proceeds without allyl rearrangement and with full retention of the configuration of the chlorovinyl fragment. The structure and purity of the obtained compounds was unambiguously confirmed by NMR spectroscopy data. Tests in rocking cells using tetrahydrofuran-water model systems (forming the structure sII similar to natural gas hydrates), gravimetric and microbiological methods showed high antihydrate, anticorrosive and bactericidal efficiency of the obtained compounds in concentrations of 0.5%.

Progress in the Synthesis of 2,3-unsaturated Glycosides

The substitution reaction of glycal (1,2-unsaturated cyclic carbohydrate derivative) at C1 by allyl rearrangement in the presence of a catalyst is called Ferrier type-I rearrangement. 2,3-Unsaturated glycosides are usually obtained from glycals through Ferrier type-I rearrangement, and their potential biological activities have gradually attracted widespread attention of researchers. This review summarizes recent advances (2009- present) in the application of various types of catalysts to Ferrier type-I rearrangement reactions, including their synthesis, mechanism, and application of 2, 3-unsaturated glycosides.

THEORETICAL STUDY OF THE INTERACTION OF 1,2-Ethanedithiol With 1,3-Dichloropropene in the Hydrazrazine Hydrate System

According to the results of quantum chemical studies in the framework of the electron density functional theory, the B3LYP / 6-311 ++ G (d, p) method proposed a theoretical mechanism for the interaction of 1,3-dichloropropene with 1,2-ethanedithiol in the hydrazine-hydrateKOH system. It was shown that the reaction proceeds sequentially in several stages, including the nucleophilic substitution of the chlorine atom of the sp3 hybridized carbon atom to the sulfur atom with the formation of the mono-substitution product, which undergoes prototropic allyl rearrangement, providing the double bond to the atom sulfur. Next, the dithiolan ring closes due to the nucleophilic attack of the sulfide anion of the second thiol group of the reagent on the carbon atom, which is in the γ position relative to the second chlorine atom. The resulting vinyldithiolan is isomerized to a more stable ethylidene-dithiolan as a result of prototropic allyl rearrangement