N-Hexyl chloride

Problem 16.19 Prepare n-hexyl chloride from n-butylmalonic ester. ... 

C,H,CH(COOC,H,), - m-C,H.,CHXOOH This acid and n-hexyl chloride have the same number of C s. 

Hexanediol, 251,873,879 n-Hexyl alcohol, 247, 253 dehydrogenation of, 322 P n Hexylacrylic acid. 465, 466 n-Hexylbenzene, 510, 516 n-Hexyl bromide. 282 n-Hexyl chloride, 270, 274 n-Hexyl cyanide, 409 n-Hexyl fluoride, 288, 289 n-Hexyl iodide, 288 n-Hexyl magnesium bromide, 237 n-Hexyl mercaptan. 496, 497 n-Hexyl nitrite, 306 1-Hexyne, 896, 899... 

The mixture 25 g theobromine, 38 ml 4 N sodium hydroxide, 60 ml isopropanol, and 17 g n-hexyl chloride were heated 24 hours to 100°C in autoclave. The solvent was removed and the residual alkaline solution was extracted with chloroform, water layer was acidified. Yield of l-hexyl-3,7-dimethylxanthine was 88% MP 82°-83°C. The product may be prepared from theobromine sodium. 20.2 g theobromine sodium, 20 n-hexyl bromide and 100 ml toluene were ground 10 hours at 100°C in a ball mill. After above written treatment 22.3 g (84.5%) 1-hexyltheobromine was prepared MP 84°C. 

Unless modified by the presence of some other functional group, the physical properties of the aryl halides are much like those of the corresponding alkyl halides. Chlorobenzene and bromobenzene, for example, have boiling points very nearly the same as those of n-hexyl chloride and n-hexyl bromide like the alkyl halides, the aryl halides are insoluble in water and soluble in organic solvents. 

Systematic data on the relation between chemical structure or reactivity of chlorine compounds and lubricant additive performance are sparse. Table 11-11 gives some four-ball test data obtained by Mould, Silver and Syrett [35], with the additives listed in order of increasing effectiveness in terms of the wear/load index. The results show numerous departures from expectations based on chemical structure. For example, there is practically as much difference between the wear/load indices for the two primary chlorides, n-hexadecyl (16.2 kg) and n-hexyl (30.4 kg), as for n-hexyl chloride and t-butyl chloride (46.1 kg). A large difference would be expected on the basis of chemical reactivity between the additive effectiveness of primary and tertiary alkyl chlorides, but only a small difference for the two primary aliphatic chlorides. The overall trends are what would be expected in general, primary and aromatic chlorides are less efficacious than secondary chlorides, which in turn... 

The catalytic activity in DHC reactions is usually measured by passing the reactant in an N2 stream over the catalyst and then through water or NaOH solution and determination of the adsorbed HCl. In the author s and other laboratories the increase in electrical conductivity was measured. The rate of HCl production decreased in the reaction of l- -butyl chloride at 603 K in the first 2 hours, but became nearly constant for several hours thereafter, and comparison of the activities after different pretreatments of a carbon could be performed when the linear increase of conductivity with time was established [143]. A few results are shown in Table 7.9. The catalytic activity of activated carbons and carbon black also increased in this case after heat treatment under nitrogen, and became quite high after treatment with ammonia at 1173 K. The activity at 603 K increased in the order l- -butyl chloride < 1-n-hexyl chloride < 1-isobutyl chloride < 1,2-dichloroethane. The surface area of the porous carbons had decreased drastically after the reaction. 

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