Alkane alkylation

Structure—Performance Characteristics of Surfactants in Contact with Alkanes, Alkyl Benzenes, and Stock Tank Oils... 

IUPAC Nomenclature of Alkanes, Alkyl Halides, and Alcohols... 

Open-chain alkanes, alkyl halide reduction, 29-31 Organosilicon hydrides bond strengths, 5-6 hypervalent silicon species, 9-11 ionic hydrogenation, 5 trivalent silicon species, 7-9 Orthoesters, reduction of, 97-99 Oxime reduction, 102... 

Paracrystallinity, Cu/ZnO/AIjOj, 31 295 2"-Paracyclophanes, 32 453 Paracyclophanes, macrocycles, 29 206-208 Paraffin, see also Alkanes alkylation, 10 165, 27 98 carbon selectivity, bed residence time effects, 39 249-250 cracking, 39 283 cyclization, 28 295 rates, 28 301, 302 double cyclization, 28 312-314 in exhaust gases, 24 66, 67 hydrogenolysis, 30 43-44 hydroisomerization, 39 183 oxidation, 32 118-121 solubility enhanced hydrogeolysis, 39 285 Parahydrogen conversion rate correlations, 27 48-50... 

Alkylation with Alkanes. Alkylation of aromatic hydrocarbons with alkanes, although possible, is more difficult than with other alkylating agents (alkyl halides, alkenes, alcohols, etc.).178 This is due to the unfavorable thermodynamics of the reaction in which hydrogen must be oxidatively removed. 

The alkylating ability of methyl and ethyl fluoride-antimony pentafluoride complexes has been investigated by Olah et al.,143,144 who showed the extraordinary reactivity of these systems. Self-condensation was observed as well as alkane alkylation. When CH3F-SbF5 was reacted with excess of CH3F at 0°C, at first only an exchanging complex was observed in the H NMR spectrum. After 0.5 h, the starting material was converted into the ferf-butyl cation 4 (Scheme 5.19). 

To improve the understanding of these alkane alkylation reactions, Olah and his group carried out experiments involving the alkylation of lower alkanes by stable car-benium ions under controlled superacidic stable ion conditions128 145 146 [Eq. (5.60)]. 

Propane as a degradation product of polyethylene (a byproduct in the reaction) was ruled out because ethylene alone under the same conditions does not give any propane. Under similar conditions but under hydrogen pressure, polyethylene reacts quantitatively to form C3 to C6 alkanes, 85% of which are isobutane and isopentane. These results further substantiate the direct alkane alkylation reaction and the intermediacy of the pentacoordinate carbonium ion. Siskin also found that when ethylene was allowed to react with ethane in a flow system, n-butane was obtained as the sole product, indicating that the ethyl cation is alkylating the primary C—H bond through a five-coordinate carbonium ion [Eq. (5.66)]. 

A century ago, Friedel and Crafts (32) reported that "when a small amount of anhydrous aluminum chloride was added to amyl chloride an immediate vigorous evolution of gas was observed in the cold. The gas was composed of hydrogen chloride accompanied by gaseous hydrocarbons not absorbed by bromine," The precise nature of these saturated hydrocarbons has not been well understood. In the course of our mechanistic studies on alkene-alkane alkylations we observed the direct reduction products of several alkyl chlorides. While there exists an extensive literature on the be-... 

Ainmoxidation, sometimes also termed oxidative ammonolysis, describes the process of catalytic oxidation of hydrocarbons (particularly alkenes, alkanes, alkyl-aromatics and alkyl-pyridines) to organic nitriles in the presence of ammonia, typically using mixed oxide catalysts ... 

Alkyl group (Section 4.4A) A group formed by removing one hydrogen from an alkane. Alkyl groups are named by replacing the suffix -one of the parent alkane with -yl. 

Toluene 5 to 100 1-10 acetylene -> alkane alkyl halide —> alkane... 

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