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

Abstract

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%.