Industrial preparation propene

An important nitrile is acrylonitrile H2C=CHCN It is prepared industrially from propene ammonia and oxygen m the presence of a special catalyst Polymers of acryl omtrile have many applications the most prominent being their use m the preparation of acrylic fibers... 

Dehydrogenation (Section 5.1) Elimination in which H2 is lost from adjacent atoms. The term is most commonly encountered in the industrial preparation of ethylene from ethane, propene from propane, 1,3-butadiene from butane, and styrene from ethylbenzene. 

Probtom 18.6 Describe an efficient industrial preparation of allylamine, HjOK HCHjNH, from propene, chlorine, and ammonia. 

Alkylation of ammonia is sometimes employed in industrial processes the resulting mixture of amines is separated by distillation. The ultimate starting materials for the industrial preparation of allylamine are propene, chlorine, and ammonia. Write a series of equations showing the industrial preparation of allylamine from these starting materials. (Allylamine has a number of uses, including the preparation of the diuretic drugs meralluride and mercaptomerin.)... 

Among other applications olefin metathesis is useful in the synthesis of cyclic alkenes, the industrial preparation of propene, and in polymerization. 

Having traversed some of the key events in the history of olefin metathesis, it is now appropriate to discuss some of the resultant fruits of that early labor in the form of practical applications in organic synthesis. Since the general reaction was bom in the industrial sector, we felt it appropriate to commence with some examples of commercial processes. Among several of the profitable industrial procedures that benefit from olefin metathesis, one of the oldest is the Phillips triolefin process (Scheme 7a) which utilizes a molybdenum-based catalyst system to convert propene (17) into a mixture of 2-butene (18) and ethene (19). These products are then used as monomers for polymer synthesis as well as for general use in petroleum-related applications. The reverse reaction can also be employed to prepare propene for alternative uses. 

One oxidation reaction that is of large industrial relevance is the oxidative dehydrogenation of light alkanes to the corresponding alkene (Scheme 3.20). This reaction has been reported to be promoted by r-GO as catalyst [29]. The importance of this reaction type is particularly high for the industrial preparation of propene from propane and butenes from butanes. Both reactions are carried out industrially in very large scale, because propene is the monomer of polypropene and also the starting material of propylene oxide, acrylonitrile, and other base chemicals. Butenes are mainly used for the preparation of 1,3-butadiene that is one of the major components of rubbers and elastomers. 

Athene formation requires that X and Y be substituents on adjacent carbon atoms By mak mg X the reference atom and identifying the carbon attached to it as the a carbon we see that atom Y is a substituent on the p carbon Carbons succeedmgly more remote from the reference atom are designated 7 8 and so on Only p elimination reactions will be dis cussed m this chapter [Beta (p) elimination reactions are also known as i 2 eliminations ] You are already familiar with one type of p elimination having seen m Section 5 1 that ethylene and propene are prepared on an industrial scale by the high temperature dehydrogenation of ethane and propane Both reactions involve (3 elimination of H2... 

Dimerization in concentrated sulfuric acid occurs mainly with those alkenes that form tertiary carbocations In some cases reaction conditions can be developed that favor the formation of higher molecular weight polymers Because these reactions proceed by way of carbocation intermediates the process is referred to as cationic polymerization We made special mention m Section 5 1 of the enormous volume of ethylene and propene production in the petrochemical industry The accompanying box summarizes the principal uses of these alkenes Most of the ethylene is converted to polyethylene, a high molecular weight polymer of ethylene Polyethylene cannot be prepared by cationic polymerization but is the simplest example of a polymer that is produced on a large scale by free radical polymerization... 

PROPENE The major use of propene is in the production of polypropylene. Two other propene-derived organic chemicals, acrylonitrile and propylene oxide, are also starting materials for polymer synthesis. Acrylonitrile is used to make acrylic fibers (see Table 6.5), and propylene oxide is one component in the preparation oi polyurethane polymers. Cumene itself has no direct uses but rather serves as the starting material in a process that yields two valuable industrial chemicals acetone and phenol. 

Before coordination polymerization was discovered by Ziegler and applied to propene by Natta, there was no polypropylene industry. Now, more than 10 ° pounds of it aie prepared each year in the United States. Ziegler and Natta shared the 1963 Nobel Prize in chemistry Ziegler for discovering novel catalytic systems for alkene polymerization and Natta for stereoregular- polymerization. 

The synthesis of aldehydes via hydroformylation of alkenes is an important industrial process used to produce in the region of 6 million tonnes a year of aldehydes. These compounds are used as intermediates in the manufacture of plasticizers, soaps, detergents and pharmaceutical products [7], While the majority of aldehydes prepared from alkene hydroformylation are done so in organic solvents, some research in 1975 showed that rhodium complexes with sulfonated phosphine ligands immobilized in water were able to hydroformylate propene with virtually complete retention of rhodium in the aqueous phase [8], Since catalyst loss is a major problem in the production of bulk chemicals of this nature, the process was scaled up, culminating in the Ruhrchemie-Rhone-Poulenc process for hydroformylation of propene, initially on a 120000 tonne per year scale [9], The development of this biphasic process represents one of the major transitions since the discovery of the hydroformylation reaction. The key transitions in this field include [10] ... 

The oxidation of propene to acrolein has been one of the most studied selective oxidation reaction. The catalysts used are usually pure bismuth molybdates owing to the fact that these phases are present in industrial catalysts and that they exhibit rather good catalytic properties (1). However the industrial catalysts also contain bivalent cation molybdates like cobalt, iron and nickel molybdates, the presence of which improves both the activity and the selectivity of the catdysts (2,3). This improvement of performances for a mixture of phases with respect to each phase component, designated synergy effect, has recently been attributed to a support effect of the bivalent cation molybdate on the bismuth molybdate (4) or to a synergy effect due to remote control (5) or to more or less strong interaction between phases (6). However, this was proposed only in view of kinetic data obtained on a prepared supported catalyst. 

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