Boride catalyst for epoxidizing olefinic compounds

#1. Field of the Invention

#This invention pertains to catalyst material for expediting the oxidation of an olefin to the corresponding oxirane; and, more particularly to a catalyst material of a boron containing substance for catalyzing the liquid phase epoxidation of olefins with organic hydroperoxides.

#Prior Art

#In this example, the liquid phase epoxidation of an olefinic compound with an organic hydroperoxide was carried out in the presence of a catalytic amount of a boron containing substance in accordance with the instant invention. A 250 ml. flask equipped with a stirrer, thermometer, reflux condenser and dropping funnel was charged with 84 g. octene-1 and 1 g. tungsten boride (WB). The charged mixture was heated to 90.degree. C. and 90% tertiary butyl hydroperoxide was added dropwise until a total of 25 g. had been added. The reaction mixture was then heated at reflux (108.degree.-110.degree. C. for 220 minutes with stirring. The heated mixture was allowed to cool and then the crude reaction product was analyzed. The analysis indicated a 36% yield of octene oxide based on the amount of charged hydroperoxide. The crude reaction product was filtered by conventional methods and the resulting filtrate was analyzed for metal content by atomic absorption analysis. No metals were detected in the filtrate.

#In these examples, various boron containing substances were used to catalyze the liquid phase epoxidation of octene-1 with tertiary butyl hydroperoxide by the procedure of Example 1. The results are shown in Table I.

#TABLE 1 __________________________________________________________________________ Selectivity Selectivity (based on (based on Moles Conversion hydro- converted Catalyst Moles hydro- Time, hydro- peroxide) octene) Example (wt. g) octene peroxide Hours peroxide to epoxide S.sub.2 __________________________________________________________________________ 2 LaB.sub.6 (1) 0.375 0.125 6.0 82% 20% 88% 3 CeB.sub.6 (1) 0.375 0.125 5.0 90% 87% 94% 4 TiB.sub.2 (1) 0.75 0.25 7.0 16% 18% 40% 5 ZrB.sub.2 (3) 0.75 0.125 6.0 89% 87% 92% 6 NbB(3) 0.75 0.125 7.0 89% 91% 91% 7 TaB(1) 0.375 0.125 6.0 73% 15% 90% 8 TaB.sub.2 (1) 0.375 0.125 6.0 62% 16% 78% 9 WB(2) 0.75 0.125 7.0 86% 92% 92% 10 MnB(3) 0.75 0.125 6.0 52% 27% 84% 11 Co.sub.3 B- Co.sub.2 B(1) 0.375 0.125 3.0 96% 15% 88% 12 CoB(1) 0.375 0.125 5.0 92% 29% 90% 13 NiB(1) 0.375 0.125 6.0 68% 81% 93% 14 FeB(2) 0.375 0.125 6.0 45% 22% 86% 15 AlB.sub.2 (3) 0.75 0.125 6.0 68% 88% 89% 16 AlB.sub.12 (1) 0.375 0.125 5.0 95% >90% 94% 17 B.sub.12 C.sub.3 (1) 0.375 0.125 6.0 47% 10% 74% 18 SiB.sub.4 (1) 0.75 0.125 5.0 76% 42% 83% 19 SiB.sub.6 (1) 0.375 0.125 6.0 66% 18% 92% 20 BN(1) 0.375 0.125 6.0 47% 10% 89% 21 CaB.sub.6 (1) 0.375 0.125 6.0 65% 23% 86% 22 W.sub.2 B.sub.5 (2) 0.375 0.125 6.0 75% 81% 94% 23 VB.sub.2 (1) 0.375 0.125 3.0 99% 49% 93% 24 CrB(2) 1.25 0.25 4.0 80% 14% 55% 25 CrB.sub.2 (1) 0.375 0.125 5.0 82% 21% 73% 26 Cr.sub.5 B.sub.3 (1) 0.375 0.125 6.0 86% 19% 69% 27 MoB(1) 1.50 0.50 1.75 95% 82% 87% 28 MoB.sub.2 (1) 0.75 0.25 2.0 98% 71% 94% 29 ZrB.sub.12 (2) 0.375 0.125 6.0 81% 53% 90% 30 UB.sub.2 (2) 0.375 0.125 6.0 95% 11% 67% __________________________________________________________________________