Abstract

A series of polyfunctional organic compounds, 1-propenyl- and 1-allyl-2-propargyloxy-3-aminomethylbenzenes containing simultaneously an aminomethyl group and fragments with С=С and С≡С bonds, were prepared in high yield (77.6–94%) by Mannich ternary condensation of 2-propenyl- and 2-allylphenols and their p-methyl-substituted derivatives with formaldehyde and secondary amines (diethylamine, piperidine, and morpholine), followed by the reaction of the products with propargyl bromide. The structures of the compounds were confirmed by the NMR spectra. The compounds were studied as inhibitors of acid corrosion of St3 steel and as antimicrobial additives to cutting fluids. 1-Propenyl-2-propargyloxy-3-diethylaminomethylbenzene showed the highest protective performance. At its concentration of 0.01 and 0.05 g L^–1, the degree of corrosion protection of St3 steel in 0.5 М Н₂SO₄ was 92.0 and 99.6% (at 25°C) and 70.0 and 98.7% (at 60°C), respectively. 1-Propenyl- and 1-allyl-2-propargyloxy-3-aminomethylbenzenes (in 0.25–1% concentrations) showed only bactericidal properties, whereas the p-methyl-substituted derivative, 1-methyl-3-allyl-4-propargyloxy-5-morpholinomethylbenzene, showed high bactericidal and fungicidal properties simultaneously. 1-Propenyl- and 1-allyl-2-propargyloxy-3-aminomethylbenzenes surpass the known antimicrobial additive, 8-hydroxyquinoline, in the bactericidal performance at identical concentrations, and 1-methyl-3-allyl-4-propargyloxy-5-morpholinomethylbenzene surpasses it in both bactericidal and fungicidal performance.

中文翻译：

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1-烯基-2-炔丙氧基-3-氨基甲基苯作为酸蚀抑制剂和切削液抗菌添加剂的合成与研究

摘要

高收率制备了一系列多官能有机化合物，同时含有氨基甲基和具有С=С和С≡С键的片段的1-丙烯基和1-烯丙基-2-炔丙基氧基-3-氨基甲基苯（77.6–94％ ），将2-丙烯基和2-烯丙基苯酚及其对甲基取代的衍生物与甲醛和仲胺（二乙胺，哌啶和吗啉）进行曼尼希三元缩合，然后使产物与炔丙基溴反应。化合物的结构通过NMR光谱确认。研究了这些化合物作为St3钢的酸腐蚀抑制剂和切削液的抗菌添加剂。1-丙烯基-2-炔丙基氧基-3-二乙基氨基甲基苯显示出最高的保护性能。在其浓度为0.01和0.05 g L ^–1时，St3的钢的腐蚀保护的在0.5МН度₂ SO ₄分别为92.0和99.6％（在25℃）和70.0和98.7％（在60℃）。1-丙烯基和1-烯丙基-2-炔丙基氧基-3-氨基甲基苯（浓度为0.25-1％）仅显示杀菌特性，而对甲基取代的衍生物1-甲基-3-烯丙基-4-炔丙基氧基- 5-吗啉代甲基苯同时显示出高杀菌和杀真菌特性。1-丙烯基和1-烯丙基-2-炔丙基氧基-3-氨基甲基苯在相同浓度下的杀菌性能均超过了已知的抗菌添加剂8-羟基喹啉和1-甲基-3-烯丙基-4-炔丙基氧基-5-吗啉代甲基苯在杀菌和杀真菌性能上都超过了它。