Industrial reactions

Adiponitrile undergoes the typical nitrile reactions, eg, hydrolysis to adipamide and adipic acid and alcoholysis to substituted amides and esters. The most important industrial reaction is the catalytic hydrogenation to hexamethylenediarnine. A variety of catalysts are used for this reduction including cobalt—nickel (46), cobalt manganese (47), cobalt boride (48), copper cobalt (49), and iron oxide (50), and Raney nickel (51). An extensive review on the hydrogenation of nitriles has been recendy pubUshed (10). 

Nitration. Nitration of ben2otrifluorides is an important industrial reaction. Mononitration of ben2otrifluoride gives pronounced meta-orientation 91% meta [98-46-4]-, 6% ortho [384-22-5]-, and 3% para [402-54-0] (296). Further nitration to 3,5-dinitroben2otrifluoride [401-99-0] can be affected under forcing conditions at 100°C. 

Reactions of /l-Butane. The most important industrial reactions of / -butane are vapor-phase oxidation to form maleic anhydride (qv), thermal cracking to produce ethylene (qv), Hquid-phase oxidation to produce acetic acid (qv) and oxygenated by-products, and isomerization to form isobutane. 

General amine chemistry is appHcable to fatty amines. Many chemical reactions using fatty amines as reactive intermediates are mn on an industrial scale to produce a wide range of important products. Important industrial reactions are as follows. 

Condensation Cure. The condensation of sdanol groups to form sdoxanes is an extremely important industrial reaction and may be represented in its simplest form as follows ... 

Reactions with Esters. Ester interchange cataly2ed by titanates is an important industrial reaction (34). 

Garbonylation Reaction. The carbonylation of methyl acetate is an important industrial reaction for producing acetic anhydride ... 

The reaction is very common in pyrazolone chemistry. Since alkoxypyrazoles and tautomerizable pyrazolones undergo this reaction and 3-pyrazolin-5-ones, like antipyrine, do not, it is assumed that the reaction takes place at C-4 of the OH tautomer. Pyrazolone diazo coupling is an important industrial reaction since the resulting azo derivatives are used as dyestuffs. For instance, tartrazine (Section 4.04.4.1.3) has been prepared this way. 3,5-Pyrazolidinediones react with aryldiazonium salts resulting in the introduction of a 4-arylazo group. As has been described in Section 4.04.2.1.4(v), diazonium salts couple in the 3-position with indazole to give azo compounds. 

Some modes of heat transfer to stirred tank reacdors are shown in Fig. 23-1 and to packed bed reactors in Fig. 23-2. Temperature and composition profiles of some processes are shown in Fig. 23-3. Operating data, catalysts, and reaction times are stated for a number of industrial reaction processes in Table 23-1. 

Laboratory studies of some important industrial reactions... 

Chemical reactions obey the rules of chemical kinetics (see Chapter 2) and chemical thermodynamics, if they occur slowly and do not exhibit a significant heat of reaction in the homogeneous system (microkinetics). Thermodynamics, as reviewed in Chapter 3, has an essential role in the scale-up of reactors. It shows the form that rate equations must take in the limiting case where a reaction has attained equilibrium. Consistency is required thermodynamically before a rate equation achieves success over tlie entire range of conversion. Generally, chemical reactions do not depend on the theory of similarity rules. However, most industrial reactions occur under heterogeneous systems (e.g., liquid/solid, gas/solid, liquid/gas, and liquid/liquid), thereby generating enormous heat of reaction. Therefore, mass and heat transfer processes (macrokinetics) that are scale-dependent often accompany the chemical reaction. The path of such chemical reactions will be... 

A limiting reactant is that reactant which is present in the smallest stoichiometric amount. In industrial reactions, the reactants are not necessarily supplied in the exact proportions demanded by the stoichiometry of the equation. Under these... 

The industrial reactions involving cis- and trans-2-butene are the same and produce the same products. There are also addition reactions where both 1-butene and 2-butene give the same product. For this reason, it is economically feasible to isomerize 1-butene to 2-butene (cis and trans) and then separate the mixture. The isomerization reaction yields two streams, one of 2-butene and the other of isobutene, which are separated by fractional distillation, each with a purity of 80-90%. Table 2-3 shows the boiling points of the different butene isomers. 

Ethanol for nonbeverage use is obtained by acid-catalyzed hydration of ethylene. Approximately 110 million gallons of ethanol a year is produced in the United States for use as a solvent or as a chemical intermediate in other industrial reactions. 

This method is the most widely used because it gives a good picture of batch reactions performed in industry. Reactions are carried out in a thermostated flask fitted with constant speed stirrer, inert gaz inlet, sampling device, thermometer, distillation column, and condenser. 

Aromatic diazonium compounds became industrially very important after Griess (1866a) discovered in 1861/62 the azo coupling reaction, by which the first azo dye was made by C. A. Martius in 1865 (see review by Smith, 1907). This is still the most important industrial reaction of diazo compounds. Hantzsch and Traumann (1888) discovered that a heteroaromatic amine, namely 2-aminothiazole, can also be diazotized. Heteroaromatic diazonium compounds were, however, only used for azo dyes much later, to a small extent in the 1930 s, but intensively since the 1950 s (see Zollinger, 1991, Ch. 7). 

Although many industrial reactions are carried out in flow reactors, this procedure is not often used in mechanistic work. Most experiments in the liquid phase that are carried out for that purpose use a constant-volume batch reactor. Thus, we shall not consider the kinetics of reactions in flow reactors, which only complicate the algebraic treatments. Because the reaction volume in solution reactions is very nearly constant, the rate is expressed as the change in the concentration of a reactant or product per unit time. Reaction rates and derived constants are preferably expressed with the second as the unit of time, even when the working unit in the laboratory is an hour or a microsecond. Molarity (mol L-1 or mol dm"3, sometimes abbreviated M) is the preferred unit of concentration. Therefore, the reaction rate, or velocity, symbolized in this book as v, has the units mol L-1 s-1. 

The difference between complete segregation and maximum mixedness is largest when the reactor is a stirred tank and is zero when the reactor is a PFR. Even for the stirred tank case, it has been difficult to find experimental evidence of segregation for single-phase reactions. Real CSTRs approximate perfect mixing when observed on the time and distance scales appropriate to industrial reactions, provided that the feed is premixed. Even with unmixed... 

A few of the important reactions carboxylic acids undergo are shown above. Soap is made by reacting sodium or potassium hydroxide with long-chain acids such as C17H35COOH (stearic acid). Acid chlorides and acid anhydrides are more reactive than their corresponding carboxylic acids and are used in the chemical industry to make various acid derivatives. A very important industrial reaction is the reaction of carboxylic acids (or the chlorides or anhydrides) with alcohols to form esters. 

Nitric acid (HNO3), which is produced in the gas phase at elevated temperature and pressure, is an important chemical in the fertilizer indushy because it can be converted into ammonium nitrate. The following overall chemical equation summarizes the industrial reaction ... 

The business of the chemicai industry is to transform inexpensive substances into more valuable ones. In many cases, catalysts play important roles in these processes. Here, we describe the roles of catalysts in some important industrial reactions. Other catalyzed industrial reactions are considered in Chapter where we describe properties of chemical equilibria. 

Although most industrial catalysts are heterogeneous, a growing number of industrial reactions use homogeneous catalysts. One example is the production of acetic acid. Most of the 2.1 billion kilograms of acetic acid produced annually is used in the polymer industry. The reaction of methanol and carbon monoxide to form acetic acid is catalyzed by a rhodium compound that dissolves in methanol ... 

Many important industrial reactions rely on heterogeneous catalysts, yet there are inherent drawbacks to heterogeneous reactions. Such reactions occur only when the reactants contact the solid surface of the catalyst. Catalysis can be much more efficient when the catalyst is dissolved in the solvent where the reaction occurs. Unfortunately, the main catalysts used by industry, metals and metal oxides, are not soluble in traditional solvents. 

C21-0058. Prepare a list of the industrial reactions described In Section 21-1 that exploit the Brc )nsted acid character of sulfuric acid. 

Kinetics provides the frame vork for describing the rate at which a chemical reaction occurs and enables us to relate the rate to a reaction mechanism that describes how the molecules react via intermediates to the eventual product. It also allows us to relate the rate to macroscopic process parameters such as concentration, pressures, and temperatures. Hence, kinetics provides us with the tools to link the microscopic world of reacting molecules to the macroscopic world of industrial reaction engineering. Obviously, kinetics is a key discipline for catalysis. 

By the enzymatic esterification of diglycerol with lauric acid, the corresponding monolaurate ester is obtained [84]. This is an important industrial reaction for the cosmetic, pharmaceutical and feed industries, since this ester is used as biodegradable non-ionic surfactant. In recent years, the synthesis of this and other polyglycerols with fatty acids has attracted growing interest in industry, leading also to a demand for enantiomerically and isomerically pure products. 

Regioselective reactions belong to the most important applications of homogeneous catalysis. An example is the hydroformylation of alkenes, which is a very important industrial reaction ... 

---