Ethylene, hydration hydrogenation

Ethylene imine Hydrazine hydrate Hydrogen sulfide. Hydroxylamme salts Inorganic Hg. compounds lodates Iodides... 

Chlorine +Sodium-Hydrate +Hydrogen Ethylen + some others... 

Tin(ll) chloride Boron trifluoride, ethylene oxide, hydrazine hydrate, nitrates, Na, K, hydrogen peroxide... 

Propanol has been manufactured by hydroformylation of ethylene (qv) (see Oxo process) followed by hydrogenation of propionaldehyde or propanal and as a by-product of vapor-phase oxidation of propane (see Hydrocarbon oxidation). Celanese operated the only commercial vapor-phase oxidation faciUty at Bishop, Texas. Since this faciUty was shut down ia 1973 (5,6), hydroformylation or 0x0 technology has been the principal process for commercial manufacture of 1-propanol ia the United States and Europe. Sasol ia South Africa makes 1-propanol by Fischer-Tropsch chemistry (7). Some attempts have been made to hydrate propylene ia an anti-Markovnikoff fashion to produce 1-propanol (8—10). However, these attempts have not been commercially successful. 

Other synthetic methods have been investigated but have not become commercial. These include, for example, the hydration of ethylene in the presence of dilute acids (weak sulfuric acid process) the conversion of acetylene to acetaldehyde, followed by hydrogenation of the aldehyde to ethyl alcohol and the Fischer-Tropsch hydrocarbon synthesis. Synthetic fuels research has resulted in a whole new look at processes to make lower molecular weight alcohols from synthesis gas. 

Other Methods of Preparation. In addition to the direct hydration process, the sulfuric acid process, and fermentation routes to manufacture ethanol, several other processes have been suggested. These include the hydration of ethylene by dilute acids, the hydrolysis of ethyl esters other than sulfates, the hydrogenation of acetaldehyde, and the use of synthesis gas. None of these methods has been successfilUy implemented on a commercial scale, but the route from synthesis gas has received a great deal of attention since the 1974 oil embargo. 

With Acyl Halides, Hydrogen Halides, and Metallic Halides. Ethylene oxide reacts with acetyl chloride at slightly elevated temperatures in the presence of hydrogen chloride to give the acetate of ethylene chlorohydrin (70). Hydrogen haUdes react to form the corresponding halohydrins (71). Aqueous solutions of ethylene oxide and a metallic haUde can result in the precipitation of the metal hydroxide (72,73). The haUdes of aluminum, chromium, iron, thorium, and zinc in dilute solution react with ethylene oxide to form sols or gels of the metal oxide hydrates and ethylene halohydrin (74). 

Direct hydration, of ethylene, 10 538 Direct hydrogenation, 6 827 Direct immunosensors, 14 154 Direct ingot (dingot) method, 25 409 Direct initiation, 14 270 Direct injection (DI) diesel engines, 12 421 Direct inlet injection, gas chromatography, 6 383, 415-416 Directional couplers, 17 446 Directional drilling techniques, in sulfur extraction, 23 572 Directive 89/107/EEC (EU), 12 36 Direct liquefaction, 6 827 Direct marketing, technical service personnel and, 24 343 Direct metal nitridation, 17 211-213 aerosol flow reactor, 17 211-212 Direct methanol fuel cells (DMFC),... 

Fries rearrangement, 18 336, 337 isomerization and transalkylation of alky-laromatics, 18 329 epoxide transformations, 18 351-352 hydration and ammonolysis of ethylene oxide, 18 351, 352 isomerization, 18 351 framework composition, 33 226-228 hydrogenation, dehydrogenation, and related reactions, 18 360-365 dehydrocyclization of s-ethylphenyl using zeolites and carbonyl sulfide, 18 364, 365... 

You may wonder why boch these processes produce isopropyl alcohol instead of (normal) propyl alcohoL With the exception of ethylene, direct or indirect hydration of an aliphatic olefin always produces an alcohol with the hydroxyl group preferentially attached to the double-bonded carbon with the least number of hydrogen atoms. 

The best-known gas hydrates are those of ethane, ethylene, propane, and isobulaue. Others include methane and I butene, most of the fluorocarbon refrigerant gases, nitrous oxide, acetylene, vinyl chloride, carbon dioxide, methyl and ethyl chloride, methyl and ethyl bromide, cyclopropane, hydrogen sulfide, methyl mercaptan, and sulfur dioxide. 

Definitive x-ray diffraction data on structure I was obtained by McMullan and Jeffrey (1965) for ethylene oxide (EO) hydrate, as presented in Table 2.2a. The crystal consists of a primitive cubic lattice, with parameters as given in Table 2.2a. The common pictorial view of structure I is presented in Figure 1.5a. In that figure, the front face of a 12 A cube is shown, with two complete 51262 (emphasizing hydrogen bonds) connecting four 512. 

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