Allyl chloride process

Table 2.4.1 Equipment Specificatons for the Allyl Chloride Process...

ADDITIONAL DATA AND NOTES The basic development of the allyl chloride process has been reported by Groll and Heame and Fairbairn, Cheney, and Chemiavsky. It was found that the three chief reactions were allyl chloride forrhation,... 

A schematic flow diagram indicating the essential equipment in the allyl chloride process is shown in Fig. 6-11. Propylene from wet storage flows... 

Table 5.1 Heats of Reaction and Kinetics Constants for the Allyl Chloride Process"...

Consider the HCl absorber (T-602) in the separation section of the allyl chloride process. Figure C.3 f Appendix C, on the CD). This equipment is shown in Figure E13.1. The function of the absorber is to contact counter currently Stream 10a, containing mainly propylene and hydrogen chloride, with water. Stream 11. The HCl is highly soluble in water and is almost conpletely absorbed to form 32 wt% hydrochloric acid. Stream 12. The gas leaving the top of the absorber. Stream 13, is almost pure propylene, which is cleaned and then recycled. 

For the problem in Section 19.3. it was determined that the pump in the Dowtherm A loop could handle only 5% increased flow, which allowed only 2% increased reactor operation. Within the reactor portion of the allyl chloride process, the pump is identified as the bottleneck. From the perspective of the entire process, assuming that all other units can be scaled up by more than 5%, the Dowtherm A loop is the bottleneck. In Section 19.3. it was shown that by operating the two reactor heat-exchange coils in parallel, the reactor could be scaled up by 15%. Altering configuration of the reactor heat-exchange coils is the act of debottlenecking the process. For this problem, it can be shown that additional scale-up in the reactor... 

Figure C.4 Propylene Refrigeration Loop for Allyl Chloride Process (Unit 600)...

Allyl chloride and a-phenylethyl chloride are reduced by Cr(II) sulphate in aqueous dimethyl formamide (DMF) in a simple second-order process. At 29.7... 

Examples for necessary process improvements through catalyst research are the development of one-step processes for a number of bulk products like acetaldehyde and acetic acid (from ethane), phenol (from benzene), acrolein (from propane), or allyl alcohol (from acrolein). For example, allyl alcohol, a chemical which is used in the production of plasticizers, flame resistors and fungicides, can be manufactured via gas-phase acetoxylation of propene in the Hoechst [1] or Bayer process [2], isomerization of propene oxide (BASF-Wyandotte), or by technologies involving the alkaline hydrolysis of allyl chloride (Dow and Shell) thereby producing stoichiometric amounts of unavoidable by-products. However, if there is a catalyst... 

Allylic chlorides can also be used as coupling partners, as shown by Lu and Liu [137]. In addition, the domino process could be used for the synthesis of benzylidene pyrrolidines, as shown for the reaction of 6/1-285 with benzylidene malonate... 

The substitution reaction of CP with methyl chloride, 2-chloroethyl radical, and allyl chloride has been treated by several different ab initio theoretical models. Depending on the method, the intrinsic barrier for the 5ivr2 process in allyl chloride is 7-11 kcalmoP higher than the barrier for the 5ivr2 reaction of methyl chloride. The reaction of CP with the 2-chloroethyl radical involves an intermediate complex, which is best described as an ethylene fragment flanked by a resonating chloride anion-chloride radical pair. There are many other points of interest. 

Hydrolysis of Chlorinated Hydrocarbons. The production of oxygenated aliphatics by the hydrolysis of chlorinated hydrocarbons includes the synthetic glycerol process and the amyl alcohols process. Glycerol (7) is made from propylene via allyl chloride (CH2 CHCH2C1), and competes with glycerol made from fats and oils for use in dynamite and alkyd resins, as a tobacco humectant and cellophane plasticizer, in cosmetics and pharmaceuticals, and for other applications. Amyl alcohols have been made since 1926 by the alkali hydrolysis of a mixture of amyl chlorides, made by the chlorination of pentanes from natural gasoline. Production from this source far exceeds the supply from the fusel oil by-product of fermentation processes. Amyl alcohol and its derivatives are used mainly as solvents. 

Commerciol Dichlorohydrin consists of the above two isomers, the proportions of which depend on method of prepn d 1.36-1.39, bp 175-80°, flash p 74°, Glycerol was the main source for the prepn of glycerol chloro-hydrins until the process for direct substitutive chlorination of propylene to allyl chloride paved the way for synthesis by chlorohydrination of allyl chloride. In the synthesis from glycerol, excess HCI is used in the presence of 4% acetic acid. The reaction is run at 130° to yield 90% of product which is mainly the a,y-form. Synthesis from propylene yields a mixt of approx 70% a,/8-form 8c 30% a,y-form. Addn of HCI to epichlorohydrin, CH2 CHCH> Cl, at... 

The selectivity greatly depends on the reaction temperature. Propylene,153 for example, gives allyl chloride in 25% yield at 210°C, whereas the yield is 96% at 400°C. This is explained by the reversibility of radical addition of chlorine to the double bond at high temperature, in contrast to radical substitution, which is not an equilibrium process.156... 

A variety of processes for synthesizing glycerol from propylene are shown in Figure 1. The first glycerol process, put on stream in 1948, followed the discovery that propylene could be chlorinated in high yields to allyl chloride [107-05-1] (see Cm.OROCARBONS AND chlorohydrocarbons, allylchloride). 

There are four processes for industrial production of allyl alcohol. One is alkaline hydrolysis of allyl chloride. A second process has two steps. The first step is oxidation of propylene to acrolein and the second step is reduction of acrolein to allyl alcohol by a hydrogen transfer reaction, using isopropyl alcohol. At present, neither of these two processes is being used industrially. Another process is isomerization of propylene oxide. Until 1984. all allyl alcohol manufacturers were using this process. Since 1985 Showa Denko K.K. has produced allyl alcohol industrially by a new process which they developed- This process, which was developed partly for the purpose of producing epichlorohydrin via allyl alcohol as the intermediate, has the potential to be the main process for production of allyl alcohol. The reaction scheme is as follows ... 

However, the electrochemical reduction requires a large excess of acids, which produce waste salts during work up and product isolation. This is certainly one of the reasons why the process has so far not competed successfully with the industrial syntheses based on allyl chloride. A few examples of nitrile reduction, which can also be carried... 

There are four processes for industrial production of allyl alcohol. One involves the alkaline hydrolysis of allyl chloride. 

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