Propylure

The reaction is of great value and most of the early work in the field is quoted and discussed in [203] by Block. As the allyl vinyl sulfide can be metallated and submitted to electrophilic substitution prior to rearrangement and the thiocarbonyl group hydrolysed in situ to a carbonyl group in the reaction product, the process has found considerable utility. The syntheses of propylure [488] and ris-jasmone [489] are early examples in which a thioaldehyde was intermediary formed (Y = H). A thioketone was involved [490] in the rearrangement of the allyl allenyl sulfide shown here. 

Fig. 12.17 C5-C7 olefin cracking with the Lurgi Propylur process...

Propylur A process for converting C4 and C5 hydrocarbons to propylene, using ZSM-5 catalyst in the presence of steam in a fixed bed. Developed by Lurgi in 2000 and licensed exclusively to Linde. Tested on an industrial scale in BP s plant in Worringen, Germany, in 2002. 

The female pheromone of the gypsy moth was claimed to be gyptol (A, Table 7.2), while the true pheromone was disparlure (85). Although the female pheromone of the American cockroach was claimed to be a cyclopropane compound B, the genuine and major pheromone was periplanone-B. The female pheromone of the pink bollworm moth was proposed as propylure (C), while the genuine pheromone was gossyplure as a mixture of two isomers. In these three cases, the synthetic compounds with the false... 

The isolation of the pheromone obtained from the female of the pink bollworm, Pectinophora gossypiella, and the determination of the structure and synthesis of the compound are also associated with the names of Jacobson and co-workers (Jones era/., 1966). The synthetic ( )-10-propyl-5-tridecadienyl acetate (propylure,... 

Eiter et al. (1967) synthesised propylure by another route. However, the product as biologically inactive. To elucidate the cause of this inconsistency, Jacobson... 

Modification of the propylure (4) molecule resulted in the synthesis of a mixture of geometrical isomers of 5,9-tridecadienyl acetate (20). This product has an attractant effect on several agricultural insect pests (Warthon and Jacobson, 1967). 

Among many other syntheses involving extensive use of ylides are those of lycoxanthin, /8,y- and y,y-carotene, 10,ll 10, ir-bisdehydrorhodo-xanthin, ethyl ( —)-abscisate, propylure, and of juvenile hormone. In the course of the last mentioned, the phosphonium salts (107 X = H or SiMea) were used successfully in olefin synthesis, but reactions involving the salt (107 X = CHgOH) were not successful. 

The reaction has been applied to a synthesis of propylure, the sex attractant of the pink bollworm moth. ... 

Jacobson (1969) has separated a mixture of the cis and trans forms of propylure (10-propyl-fru/is-5,9-tridecadienyl acetate) (CXXIXX the sex pheromone of the female pink bollworm moth (Pectinophora gossypiella (Saunders)), into its pure isomers by thin-layer chromatography. The infrared spectrum of the separated frans-propylure had a medium band at 965 cm trans HC=CH) that was absent in the spectrum of the cis isomer. The spectrum of cis-propylure had an inflection at 740 cm. c/s-Propylure inhibited or masked the activity of the trans isomer, as... 

Ac [10297-61-7]. l-Acetoxy-10 propyl-5y9-trideca-diene. Propylure. Sex attractant of the female pink bollworm moth Pectinophora gossypelia. Liq. Bpo 5 110-120 . 

The Propylur process converts low value light hydrocarbons enriched in olefins into petrochemicals such as propylene and is based on a shape-selective heterogeneous zeolitic catalyst of the ZSM-5 type. 

The feedstock for the Propylur process can be C4 cuts. Raffinate I, Raffinate 11 or gasoline fraction. Naturally, a feedstock with high olefin content is more favorable. Compounds such as paraffins, cycloalkanes, and aromatics are rarely converted when they pass through the reactor. The diolefm content should be limited to approximately 1.5 % in order to reduce the formation of gum and coke during the reaction. 

The Propylur reactor is an adiabatic fixed bed type, similar to that employed in a Claus unit. The operating temperature is approximately 500 "C and pressure is slightly above atmospheric. The hydrocarbon partial pressure is reduced by diluting the feedstock with steam, in order to shift the equilibrium towards the desired product (propylene). This also minimizes coking and gum formation. The reaction is endothermic and requires additional heat. 

When integrated with an ethylene plant, the Propylur plant can give increased propylene to ethylene ratios in a steam cracker. The typical yields of... 

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