N- Propyl benzene

FIGURE 3.1.1.10.1 Logarithm of mole fraction solubility (In x) versus reciprocal temperature for n-propyl benzene. 

Aliphatic Hydroxylation. Simple aliphatic molecules such as -butane, -pentane, and n-hexane, as well as alicylcic compounds such as cyclohexane, are known to be oxidized to alcohols. Likewise alkyl side chains of aromatic compounds such as cyclohexane, are known to be oxidized to alcohols, but alkyl side chains of aromatic compounds are more readily oxidized, often at more than one position, and so provide good examples of this type of oxidation. The n-propyl side chain of n-propyl benzene can be oxidized at any one of three carbons to yield 3-phenylpropan-l-ol (C6H5CH2CH2CH2OH) by -oxidation, benzylmethyl carbinol (C6H5CH2CHOHCH3) by co-1 oxidation, and ethyl-phenylcarbinol (C6H5CHOHCH2CH3) by -oxidation. Further oxidation of these alcohols is also possible. 

Another intercalation was observed in the inclusion crystals of CA with n-propylbenzene [32c], Heat treatment of a 1 1 molar ratio of CA with n-propyl-benzene gave intermediate inclusion crystals with the same guests at 2 1 stoichiometry. Comparison of both crystal structures by powder X-ray diffraction indicated that the bilayers slide past each other on the lipophilic sides by ca. 4.5 A in the horizontal direction. The 2 1 crystals can be returned to the original crystal (1 1) by soaking them in the liquid n-propy I benzene, and the bilayer can slide back to the initial position without changing to the amorphous state. 

Scheme 26 Hydrogenation of lp-henyl-1-propyne to 1 -phenyl-1-propene and n-propyl-benzene...

Off-gas analyses were done by mass spectrometry and reactor effluent samples were analyzed by glc. Most of the glc work was done with an 8-foot 1/4-inch OD column containing 10% SE-30 on acid washed Chromsorb W. However, the separation of n-propyl-benzene from cumene had to be done with a dual 3/16-inch copper column consisting of a 12-foot section having 10% Bentone 34 and 10% Dow Corning silicone gum 550 on 60-80 mesh acid washed Chromsorb W and a 6-foot section containing 20% Apiezon L on 60-80 mesh acid washed Chromsorb P. 

This is more in line with the electron impact results and with the results from the pyroloysis of n-propyl benzene. Stevenson has since stated that the electron impact work already quoted together with some unpublished results leads to D(CH3-H) Z)(G2H5 H) ==5 1 0 7 kcal. Evidence from the pyrolysis of iodides, though possibly not very reliable, gives 6 kcal for this quantity. Accordingly a value of 96 kcal for D(C2H5 -H) can be adopted with fair confidence. This is a little lower than the value commonly adopted until recently. 

Pyrolysis of n-propyl benzene gives Z)(Ph. GH2 - G2H5) as 57 5 kcal, leading to 94 kcal for Z)(Et-H) usine the known value oi... 

The major product is isopropylbenzene—approximately twice as much as n-propyl benzene. The rearrangement in this mechanism occurs because primary cations do not exist in solution (Chapter 17) so that the alkyl halide-AlCl3 complex must either react directly or rearrange to the more stable secondary carbocation. 

Note -Propylbenzene and n-butylbenzene may be prepared by the same method and with the same quantities of bromobenzene and alkyl branide. The fraction which is collected in the preparation of n-propyl-benzene boils at 156-162°. For n-butylbenzene the fraction collected is 180-186°. The yield of n-butylbenzene is about 50 per cent of theory. 

Methyl-2- n-propyl-benzene 10 Arom2 0.01-0.17 Gasoline LUFT 1988... 

Since 1-5 ring closure provides a route for the skeletal isomerization of alkanes, isomerization of substituted benzenes by a cyclic mechanism should also be possible. That was verified by Shephard and Rooney (95), who found that, on 0.5% Pt/Al2O3, interconversion of o-ethyltoluene and n-propyl-benzene accompanied dehydrocyclization to indane (Scheme 80). In these... 

In the case of the liquid phase non-catalytic oxidation of ethyl benzene and n-propyl benzene the oxygen behaves in the same manner as the... 

Studies were made of the behavior of both isomeric propylbenzenes in contact with samples of nickel-alumina catalyst containing 10, 20, and 30 % Ni. The hydrocarbons were passed over the catalysts at the rate of 0.8 hr."i with a hydrogen-hydrocarbon ratio of 5 1. The runs with n-propyl-benzene were made at 465° and 25 and 50 atmospheres hydrogen pressure. 

Under the given conditions the main reaction of n-butylbenzene is the partial or complete hydrogenolysis of the side chain to form n-propyl-benzene, ethylbenzene, toluene, and benzene. In addition hydrogenation of the benzene ring, contraction of the hexamethylene cycle to a five-membered one, hydrogen cleavage of the latter, formation of xylenes, methylpropylbenzenes, and diethylbenzenes, and dehydrocyclization of the side chain of w-butylbenzene to naphthalene are also observed. 

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