Oxo-D process

Oxo-D process (Petro-Tex),180 and a technology developed by BP applying a tin-antimony oxide catalyst.181,182 The Phillips technology produces 1,3-butadiene with 88-92% selectivity at 75-80% conversion.179 A new catalyst used in the Nippon Zeon process offers improved process characteristics.183... 

Various processes have been developed, espedally by BP Chemical, Polymer Corporation. Shell, etc., but the main industrial achievements in this area arc due to Phillips (OXD process, originally used in its Borger. Texas, plant, currently shut down) and Petrotex (Oxo —D process employed in the Tenneco fadliiies at Houston, Texas, and at the Firestone plant at Orange. Texas, etc). Figure 6.3 gives a flow sheet of the Petrotex technology. 

The Houdry Catadiene process was used extensively for the production of butadiene, either by itself (n-butane to butadiene) or in conjunction with catalytic oxydehydrogenation of n-butene to butadiene. The latter was commercialized by the Petro-Tex Chemical Corp. and was called the Oxo-D process. A similar oxydehydrogenation approach for the production of butadiene was also adopted by Phillips Petroleum in their 0-X-D process. ... 

Direct use of oxygen as a means of dehydrogenating, for example, ethane to ethylene. Oxydehydrogenation has successful commercial applications in the conversion of n-butenes to butadiene (e.g., as in the Oxo-D process referred to earlier), but not yet for the production of ethylene or propylene. 

O-X-D [Oxidative dehydrogenation] A process for converting n-butane to butadiene by selective atmospheric oxidation over a catalyst. Developed by the Phillips Petroleum Company and used by that company in Texas from 1971 to 1976. See also Oxo-D. 

Fig. 6.3. Butadiene manufacture by oxidative dehydrogenation of n-butcncs. Oxo-D Petrotex process.

D/chloro-5-Cyclohexyl-2-Oxo-2,3-D/hydro 1 H-Benzo(fj-Diazepine-1,4 fa) Process Using Sodium Hypochlorite — 40 ml of a solution of sodium hypochlorite of 14.5 British chloro-metric degrees are added to a suspension of 5.4 grams of 7 chloro-5 cyclohexyl-2 oxo-2,3-dihydro 1 H-benzo(f)diazepine-1,4 in BO ml of methylene chloride. The mixture is stirred at room temperature for 15 minutes the solid dissolves rapidly. The organic iayer is decanted, washed with water, dried over anhydrous Sodium sulfate and the solvent evaporated under reduced pressure without exceeding a temperature of 30 C. The residue is taken up in a little diisopropyl ether and the crystals which form are dried. They are recrystallized as rapidly as possible from ethyl acetate. Colorless crystals are obtained (3.9 grams yield, B5%) MP < = 163°C, with decomposition. 

Figure 5.1. The generations of oxo processes [3] (symbolized by full points).A, First generation Ruhrchemie process 1943 (diaden process [4]) B, second generation Ruhrchemie process C, second generation BASF process D, second generation Kuhlmann process E, third generation Shell process F, third generation LPO (UCC) process G, third generation BASF process H, third generation Exxon (Kuhlmann) process I, fourth generation Ruhrchemie/Rhone-Poulenc process...

P = monoalkene polymerization O = monoalkenc oligomerization X = oxo process D = alkadiene polymerization M = methyl methacrylate polymerization A = 1-alkene polymerization. b Complex unspecified. 

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