N-Dimethyldodecylamine Oxide

A solution of 21.3 g. (0.10 mole) of freshly distilled N,N-dimethyldodecylamine (Note 1), 9.6 g (0.10 mole) of 94% -butyl hydroperoxide (Note 2), and 0.050 g. of vanadium oxyacetylacetonate (Note 3) in 27 g. (34 ml.) of Cbutyl alcohol is placed in a 250-ml. round-bottomed flask fitted with a. thermometer, a reflux condenser, and a heating mantle. The reaction mixture is heated to approximately 65-70°, at which point an exothermic reaction begins. The heating is discontinued until the vigorous exothermic reaction subsides (about 5 minutes) and then the reaction mixture is heated at reflux (the reaction mixture boils at 90°) for 25 minutes. After the resulting mixture has been cooled to room temperature, it is analyzed (Note 4) to establish the absence oft-butyl hydroperoxide, and then concentrated with a rotary evaporator (30-35° bath with 30-40 mm. pressure). The crude solid residue is triturated with 50 ml. of cold (0-5°), anhydrous diethyl ether and then filtered under conditions which prevent exposure of the residual amine oxide to atmospheric moisture (Note 5). The residual solid is washed with 50 ml. of cold (0-5°) anhydrous diethyl ether and then dried under reduced pressure to leave 12.9-15.5 g. of the crystalline amine oxide, m.p. 131-131.5°. Concentration of the mother liquors and trituration of the residual paste with 25 ml. of cold (0-5°) anhydrous diethyl ether separates another 4.9-3.4 g. of the amine oxide, m.]). 130-131°. The total yield of the crystalline amine oxide (Note 6) is 17.4-18.9 g. (76 83%). 

N-Dimethyldodecylamine purchased from Eastman Organic Chemicals is approximately 90% pure. This material should be fractionally distilled with a spinning band column to obtain the pure amine, b.p. 116-117° (4 mm.). 

-Butyl hydroperoxide purchased from the Lucidol Division, Wallace and Tiernan, Inc., is approximately 92% pure. A portion of the major impurity, water, can be removed by drying the commercial material over anhydrous magnesium sulfate for 2 days to leave material that is 94r-97% pure. 

Vanadium oxyacetylacetonate may be purchased from Alfa Inorganics, Inc., Beverly, Massachusetts. 

Although consumption of the hydroperoxide is normally complete, the absence of this peroxide in the reaction mixture should be established by testing with moist starch-iodide paper or by iodometric titration.2 The amine oxide content may be determined by titration with standard aqueous hydrochloric acid after any amine present has been consumed by reaction with methyl iodide for 1 hour at room temperature.3 From this volumetric analysis the submitters determined the yield of amine oxide to be 86%. The checkers found that the reaction could be followed by measuring the n.m.r. spectra in -butyl alcohol solution where the n.m.r. N-methyl signals of the amine (at S 2.03) and the amine oxide (at S 2.98) are readily observed. 

---

The silicon precursor and N, N-dimethyldodecylamine oxide exhibit different electronic properties under different pH conditions, thus the driving forces and the corresponding sample structure may be different in various pH values. We performed the synthesis process at pH<0, pH=2, pH=7, and pH>10, respectively. The silicon precursor did not condense when pH<0. Figure 2 illustrates the Figure 1. TEM image of calcined LZC... 

The most effective additives for increasing the stability of the foam produced by surfactant solutions appear to be long-chain, often water-insoluble, polar compounds with straight-chain hydrocarbon groups of approximately the same length as the hydrophobic group of the surfactant. Examples are lauryl alcohol for use with sodium dodecyl sulfate, Af,/V-bis(hydroxyethyl) lauramide for use with dodecylbenzenesulfonate, lauric acid for use with potassium laurate, and N,N-dimethyldodecylamine oxide for use with dodecylbenzenesulfonate and other anionics. 

N.N-Dimethyldodecylamine oxide, 456 16a,17a-(DimethyIenedioxy)-A1-, i-pregna-triene-3,20-dione, 172 Dimethylethynylcarbinyl chloride, 465... 

Dimethyidiphenyl siloxanes and silicones. See Phenylmethyl polysiloxane Dimethyidithiocarbamate zinc salt. See Zinc dimethyidithiocarbamate N,N-Dimethyl-1-dodecanamine-N-oxide Dimethyldodecylamine-N-oxide N,N-Dimethyldodecylamine oxide N,N-Dimethyldodecylamine-N-ox-ide. See Lauramine oxide... 

DimethyIdodecylamine-N-oxide N,N-Dimethyldodecylamine oxide N,N-Dimethyldodecylamine-N-oxide. See Lauramine oxide... 

---