Hydrocarbons from alcohols

The higher members above heptadecane are wax-like solids at ordinary temperatures. They occur naturally in petroleum and ozokerite, and are obtained as mixtures in the higher distillation products of petroleum, viz., in paraffin oil, paraffin and vaseline. They are also obtained as distillation products from coal, wood and fish oil. The separation of individual hydrocarbons by the fractional distillation of these mixtures is a very difficult operation, so that the preparation of the pure hydrocarbons is always accomplished by means of one of the general methods of synthesis from related compounds. These methods are those for preparing the hydrocarbons from the next lower hydrocarbon, discussed on pages 16-29, and those for preparing hydrocarbons from alcohols and unsaturated hydrocarbons which will be discussed when these compounds are considered. 

The products formed vary somewhat with the catalyst and the temperature employed, but in general represent all the stages of the oxidation of aliphatic hydrocarbons from alcohols to oxygenated acids, together with hydrocarbons and oxidized bodies resulting from secondary reactions. Alcohols, ketones, aldehydes, naphthenic acids and other substances formed make up a mixture of such complexity that quantitative analysis, even, is a hopelessly complicated task. 0... 

Reduction by dissolving metals Partial hydrogenation of the nucleus Hydrocarbons from alcohols... 

It would lead us beyond the scope of this book to mention aU the processes of azeotropic distillation known at the present time, since the publications and patents on this subject are numerous the two examples selected show the wide possibilities that exist. Another field of azeotropic distillation is the dehydration of organic compoimds,. such as formic acid, acetic acid and pyridine. Further, mention may be made of the separation of hydrocarbons from alcohols, the purification of aromatic... 

Hydrazine Hydrocarbons from alcohols and ethers Preferential and selective reduction s. 17, 136 HsN NH ... 

Hydrocarbons from alcohols via bromides s. 18, 125 Replacement of hydroxyl by hydrogen via mesylates and iodides s. 19, 114 via mesylates and benzyl thioethers s. 16, 107 via ketones and cyclic mercaptals s. 16, 138 OH H... 

Hydrocarbons from alcohols and ethers Preferential and selective reduction... 

The most important reactions taking place on the hydroxy groups of alcohols are 0-H bond cleavage and C-O bond cleavage. With the O-H bond cleavage, reactions with strong acids proceed, as do oxidations of primary alcohols to aldehydes, secondary alcohols to ketones and reactions with organic acids (formation of esters). In foods the last three reactions are particularly important, and are usually enzymatically catalysed. Other important reactions are dehydration and the opposite reaction, hydration, which yield unsaturated hydrocarbons from alcohols and isomeric alcohols from unsaturated hydrocarbons, respectively. These reactions are particularly important in terpenic alcohols. In oleochemistry, oxidation and esterification reactions are used for the production of various lipid derivatives. 

Sodium trihydridocyanoborate/triphenyl phosphite methiodide Hydrocarbons from alcohols s. 27, 74... 

A soln. of Li-cw-cinnamylalkoxide, prepared by treatment of cw-cinnamyl alcohol with ethereal methyllithium at 0°, added at room temp, to a suspension of Cul in dry tetrahydrofuran, stirred an additional 0.5 hr., cooled to -78°, a soln. of n-butyllithium in hexane added during 10 min., treated with a soln. of N,N-methylphenylaminotriphenylphosphonium iodide in dimethylformamide during 0.5 hr., kept 1 hr. at -78°, then warmed to room temp, during 2 hrs. with continued stirring -> 1-phenyl-cw-l-heptene. Y 80%. F. e., regio- and stereo-specificity, also synthesis of hydrocarbons from alcohols, s. Y. Tanigawa et al., Am. Soc. 99, 2361 (1977). 

Carbonyl compounds can be primary (from radicals or hydroperoxides) or secondary (from alcohols). Thus the picture emerges of hydrocarbon oxidations occurring through compHcated series-sequential pathways as in Figure 1, where clearly other reactions could be going on as well. All possible pathways are pursued to some extent traffic along any pathway is a function of energy requirements and relative concentrations. 

Synthetic piae oil is produced by the acid-cataly2ed hydration of mainly a-piaene derived from sulfate turpentine, followed by distillation of the cmde mixture of hydrocarbons and alcohols. The predominant alcohol obtained is a-terpiueol, although under the usual conditions of the reaction, reversible and dehydration reactions lead to multiple hydrocarbon and alcohol components (Fig. 1). 

Important commercial sesquiterpenes mosdy come from essential oils, for example, cedrene and cedrol from cedarwood oil. Many sesquiterpene hydrocarbons and alcohols are important in perfumery as well as being raw materials for synthesis of new fragrance materials. There are probably over 3000 sesquiterpenes that have been isolated and identified in nature. 

Terpin hydrate [2451-01-6] (10), one of the most weU-known expectorants, is isolated from cmde pine rosin left after the distillation of volatile terpene hydrocarbons and alcohols. It is also manufactured from turpentine (a-pinene) by acid-cataly2ed hydration. Terpin hydrate may exist as cis and trans isomers, but only the cis isomer forms a stable, crystalline monohydrate. Terpin hydrate is available in the United States only in prescription products. 

Removal of unsaturated hydrocarbons, of alcohols and of ethers from saturated hydrocarbons or alkyl halides by washing with cold concentrated sulfuric acid. 

As a constituent of synthesis gas, hydrogen is a precursor for ammonia, methanol, Oxo alcohols, and hydrocarbons from Fischer Tropsch processes. The direct use of hydrogen as a clean fuel for automobiles and buses is currently being evaluated compared to fuel cell vehicles that use hydrocarbon fuels which are converted through on-board reformers to a hydrogen-rich gas. Direct use of H2 provides greater efficiency and environmental benefits. ... 

ALCOHOL represents a convenient method of converting allyl alcohol to 2-substituted 1-propanols, while a one-pot reaction sequence of alkylation (alkyl lithium) and reduction (lithium—liquid ammonia) provides excellent yields of AROMATIC HYDROCARBONS FROM AROMATIC KETONES AND ALDEHYDES. 

Alcohols, primary, 56,40 ALDEHYDES, acetylenic, 55, 52 aromatic, aromatic hydrocarbons from, 55,7... 

This method is especially valid for the preparation of gold NPs mixed with activated carbon, which are active and stable for the selective oxidation of hydrocarbons and alcohols in water. Over activated carbon gold could not be directly deposited as NPs by using the techniques described above, such as DP and even by GG. Gold colloids with mean diameters from 2.5 to lOnm stabilized by poly vinyl alcohol or poly vinyl p5rrolidone are used. 

V. E. Ignateva, A. G. Telin, N. I. Khisamutdinov, S. V. Safronov, V. N. Artemev, and Y. A. Ermilov. Composition for oil extraction—contains hydrocarbon- or alcohol-containing solvent, water and vat residue from production of glycerine or ethylene glycol. Patent RU 2065941-C, 1996. 

Fig. 9. Pulse microreactor system for use with 13C-labeled hydrocarbons. D, E, and J are microreactors J contains the catalyst to be used for hydrocarbon skeletal reaction D and E are used, when necessary, to generate the required reactant hydrocarbon from a non-hydrocarbon precursor (e.g., alcohol dehydration in D and olefin hydrogenation in E) reactant injected at C. F is a trap which allows the accumulation of products from several reaction pulses before analysis G is a G.P.C. column, K a katharometer. Traps H collect fractions separated on G for subsequent mass spectrometric study. When generating reactant hydrocarbon in D and E, a two-step process is preferable in which, with J below reaction temperature, the purified reactant hydrocarbon is collected in H, and this is recycled as reactant with D and E below reaction temperature but with J at reaction temperature. After C. Corolleur, S. Corolleur, and F. G. Gault, J. Catal. 24, 385 (1972).

A process for the manufacture of hydrocarbon oils, alcohols, fatty acids, etc., from coal. 

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