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By F. Albert, And Geoffrey Wilkinson, Cotton

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Sample text

8 mol kgcat h ). The space time yield of LO after 24 h was 425 gLO kgcat The rhenium compound methyltrioxorhenium (MTO) was first reported as an active and stable epoxidation catalyst by Herrmann et al. [156], and has been the subject of extensive investigations [132,157–160]. A problem with the catalyst is that it tends to form diols, but the addition of Lewis bases such as pyridine and particularly pyrazole hampers the formation of diols without affecting the rate. 6). The reaction is greatly accelerated by the use of CF3CH2OH as a solvent [162], likely because it polarizes the hydrogen peroxide molecule, which renders it more reactive.

15 s [99] Halcon styrene monomer process; Mo naphthenate þ K naphthenate promoter/EBHP; 90  C, 10 bar; conv. hydroperoxide 92%, select. 90%. 11 sÀ1 [101] Eniricerche process; TS-1 (Si/Ti ¼ 46)/H2O2; 30  C, 4 atm, MeOH solvent, tert-butylmethyl ether, 10 min; conv. (H2O2) 90%, (C3H6) 5%, select. 97%. 5, solvent H2O, MeOH, MTBE; conv. (H2O2) 94%, (C3H6) 19%, select. 95%. 12 sÀ1 5,400 hÀ1. Yielda ¼ 250 g kgcat [9] Space time yield (g of epoxide per kg catalyst per hour). are generally composed of silver (10–20 wt%) supported on a low–surface area (1– 2 m2 gÀ1) a-Al2O3 support with alkali metal (500–1,200 wppm) promoters [87–89], especially Cs [90–92], and may contain fluoride [93], Re [94], and other promoters (see Chapter 8).

References 30 S. Ted Oyama epoxidation of terminal alkenes, a transformation that poses synthetic challenges [255] which have not been fully addressed by catalytic systems such as Ti (tartrate) [75], Mn(salen) [220,221], and Fe(porphyrin) complexes [256]. Arnold and coworkers point out that several enzymes including cytochrome 450 [257], MMO [258], toluene monooxygenase [259], styrene monooxygenase [260], chloroperoxidase [261], as well as microbial whole-cell catalysts such as Rhodococcus rhodochrous [262], do catalyze the enantioselective epoxidation of terminal olefins, but although high optical purity is achieved in some cases, these biocatalytic systems generally only produce a single enantiomer, and can only accept a limited range of alkene substrates [263].

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