reaction of decaborane with acetylene

The acetylene first passed through a sulfuric acid scrubbing tower to remove acetone, then a sodium hydroxide column and a calcium chloride colum. of diethyl ether, and 6.5 g. (9 ml.) The temperature of the reaction was maintained at 110 C. During the reaction, the mixture foamed vigorously (hydrogen evolution) for 2 to 3 hours and then subsided slowly while the color changed from colorless to burnt orange. 29. Infrared analysis showed the product to be the same as that obtained from the reaction of Example 1 using tetrahydrofuran as solvent. (0.38 mole) of diethyl ether were placed in a 250 ml. The yellow, oily residue was sublimed to give 3.5 g. of a white solid product, which was identified by mass spectrometric analysis as B H (CHCH), a 60 percent yield based on the decaborane used. 3 40 65-100 m 15 8. of diethyl sulfide, 25 ml. The method of claim 1 wherein said material is dimethyl sulfide. Excess diethylsulfide then was pumped off at room temperature and reduced pressure. The material was washed with water and filtered. 17. b Dioxane. 28, 1955, by Elmar R. Altwicker, Alfred B. Garrett, Samuel W. Harris, and Earl A. Weilmuenster and issued as US. 15. employing one of the materials produced in accordance. The equation for the reaction is summarized below (equation 2). Infrared analysis indicated the monotrimethylamine-decaborane complex plus some CH3 BlOH1QCHC=CHZ and possibly some material containing BO bonds. 7 39 b 18. The method of claim 1 wherein said borane is decaborane, wherein said acetylenic hydrocarbon is methyl acetylene and wherein said material is acetonitrile. (0.38 mole) of diethyl ether were placed in a 250 ml. 05 8. Example 18 6.15 g. 0.041 mole) of monoethyldecaborane and 40 ml. of dioxane and 120 ml. The mixture Was filtered through a filter aid (Celite), the ether was evaporated off and the remaining material was washed with concentrated H 50; and water. flask, and the ether was removed by distillation. The temperature of the reaction was maintained at C. During the reaction, the mixture foamed vigorously (hydrogen evolution) for 2 to 3 hours and then subsided slowly while the color changed from colorless to burnt orange. Duplicate chemical analyses of the product obtained from the distillation at 5 mm. The compound of the formula prepared as described in Examples 10, 73-78 and 81-123 has the same structural formula as shown in FIGURE 2 with the exception that in FIGURE 2 the hydrogen atom designated with a single asterisk is replaced by The compound of the formula prepared as described in Example 11 has the same structural formula as shown in FIGURE 2 with the exception that in FIGURE 2 the hydrogen atom designated with a single asterisk is replaced by (CH CH The compound of the formula B H CHC(CH CH prepared as described in Example 12 has the same structural formula as shown in FIGURE 2 with the exception that in FIGURE 2 the hydrogen atom designated with a single asterisk is replaced by (CH CH The compound of the formula prepared as described in Example 13 has the same structural formula as shown in FIGURE 2 with the exception that in FIGURE 2 the hydrogen atom designated with a single asterisk and the hydrogen atom designated with a double asterisk are both replaced by CH CH CH The compound of the formula H B I I OHC 47:0112. prepared as described in Example 21 has the same structural formula as shown in FIGURE 2 with the exception that in FIGURE 2 the hydrogen atom designated with a single asterisk is replaced by The compound of the formula B H CHC(CH CCH B H prepared as described in Example 14 has the structural formula shown in FIGURE 3 of the accompanying drawll'lgS. The liquid products of this invention are also of high density. The mixture was stirred and the pressure dropped to 40 p.s.i.g. Magne-Dash autoclave, which then was flushed with nitrogen. 0 i 55. 3 66. The mixture then was stirred and the pressure dropped to 40 p.s.i.g. 20. Because of their high chemical reactivity and heating values, the liquid products of this invention can be employed as fuels in ramjet engines and in afterburning and other auxiliary burning schemes for the turbojet and by pass or ducted type engines. At the end of the 3.5 hour reaction period a mass spectrometric determination of the reaction mixture indicated the presence of 3.0 mole percent of unreacted ethyldecaborane and 0.34 mole percent of the reaction product, C H B H (CHCH), a 13 percent yield.

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