Low foaming N,N'-dialkyl malic imine wetting agent
A technology of malamide and dialkyl, applied in the field of dialkyl malamide, which can solve the problems of reducing the surface tension of aqueous media
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Embodiment 1
[0046] N, N'-di-isobutyl DL-malic acid amide is prepared by reacting isobutylamine with DL-diethyl malate. To a round bottom flask was added DL-diethylmalate (5.229 g, 1 eq) and isobutylamine (14.058 g, 7 eq). The pale yellow clear solution was stirred at room temperature for 24 hours, after which time a white solid precipitated from solution. The solid was filtered, washed with hexane (3 x 25 mL) and dried under vacuum (1.96 g, 29% yield). The product was determined to be greater than 99% pure by NMR analysis.
Embodiment 2
[0048] N, N'-diisoamyl DL-malic acid amide is prepared by reacting isoamylamine with DL-diethyl malate. To a round bottom flask was added DL-diethylmalate (20.013 g, 0.1052 mole, 1 eq) and isoamylamine (27.778 g, 3.03 eq). The pale yellow clear solution was stirred at room temperature for 20 hours before heating under vacuum to remove excess amine. A white waxy solid was obtained. The solid was triturated with hexanes (4 x 100 mL) and the product was filtered through a frit after each trituration. Finally, the material was transferred to a round bottom flask and the white solid was dried under vacuum for 1 hour while heating (less than 100 °C) to remove all remaining amine and hexane (28.99 g, yield ~100 %). The product was approximately 100% pure by NMR analysis.
Embodiment 3
[0050] N, N'-di-2-ethylhexyl DL-malic acid amide is prepared by reacting 2-ethylhexylamine with DL-malic acid diethyl ester. To a round bottom flask was added DL-diethylmalate (10.009 g, 1 eq), methanol (31 ml) and 2-ethylhexylamine (13.602 g, 2.00 eq). The pale yellow clear liquid was stirred at room temperature for 7 days, then methanol and ethanol were removed in vacuo. The concentrated reaction mixture was refluxed at 70°C for 8 hours. Residual ethanol was removed under vacuum to yield a clear amber liquid (8.77 g, 47% yield). The product passes 1 H and 13 C NMR and GC / MS analysis determined the purity to be about 85-90%; other components of the product mixture included half amides / half esters.
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