Alcohols long-chain primary

Long-chain primary alcohols, eg, triacontanol, can be prepared by the hydroboration, isomerization, and oxidation of the corresponding internal alkenes (437). The less thermodynamically stable stereoisomer can be transformed into the more stable one by heating, eg, i j -into /ra/ j -myrtanjiborane (204). 

Waxes are esters of tatty acids and long chain primary alcohols... 

Waxes are esters of fatty acids with long chain primary alcohols (Figure 12.2). The fatty acid is usually straight chain which may be saturated or mono-unsat-urated although occasionally branched chain or hydroxy acids are found. They are extremely non-polar compounds and are relatively inert chemically but they can be hydrolysed using a strong alkali, such as potassium hydroxide, a process called saponification. 

Varieties of primary and secondary alcohols are selectively oxidized to aldehyde or carbonyl compounds in moderate to excellent yields as summarized in Table 3. As can be seen, /(-substituted benzyl alcohols (e.g., -Cl, -CH3, -OCH3, and -NO2) yielded > 90% of product conversion in 3-4 h of reaction time with TOP in the range of 84-155 h (entries 2-5, Table 3), Heterocyclic alcohols with sulfur- and nitrogen-containing compoimds are found to show the best catalytic yield with TOP of 1517 and 902 h for (pyrindin-2-yl)methanol and (thiophene-2-yl) methanol, respectively (entries 9 and 10, Table 3). Some of aliphatic primary alcohols (long chain alcohols) and secondary alcohols (cyclohexanol, its methyl substituted derivatives and norboman-2-ol) are also selectively oxidized by the membrane catalyst (entries 11-14 and 15-17, Table 3) with TOP values in the window of 8-... 

Potassium hydroxide in DMSO has proved a useful reagent to promote the reaction of activated aryl and heteroaryl chlorides with long chain primary alcohols, to form the corresponding ethers (equation 16).157 The procedure failed with secondary alcohols. 

A group termed other esters includes a large variety of functionally diverse lipids. Wax esters are a typical example. The term wax is used commonly for esters of long-chain fatty acids with long-chain primary alcohols, but sometimes it is used for the entire mixture of lipids that contain waxes. Ester waxes are present in both plants and animals where they form the water-repellent surface coating (e.g., skin surface of animals and the leaf cuticle). Esters of normal alcohols with monobranched or multibranched fatty acids have been found in the preen glands of birds (2). Complex waxes (in which either the fatty acid or the alcohol component or both has a complex structure) have been isolated from some bacteria. Diesters... 

J. Sci. Research 4A, 365-71 (1951). Dielectric absorption of crystalline long-chain primary alcohols at low frequencies. 

The montmorillonite promoted alkylation of benzene with long chain primary and secondary alcohols gave mixtures of the 1- 2- and 3-phenyl alkanes. No 1-phenyl products were obtained when secondary alcohols were used. Reaction with tertiary alcohols gave a single alkylated product in better than 95% yield after about a five minute reaction at 80°C (Eqn. 22.6). ... 

A few years later the Swem laboratory then developed an activator which they claimed to be the most successful in activating dimethyl sulfoxide toward oxidation, namely, oxalyl chloride. Since oxalyl chloride reacted violently and exothermically with dimethyl sulfoxide, successful activation required the use of low temperatures to form the initial intermediate.6 Swem et al. reported the oxidation of long chain primary alcohols to aldehydes which was previously unsuccessful by first converting to the sulfonate ester (either mesylate or tosylate) and then employing the dimethyl sulfoxide-acetic anhydride procedure. They found that long-chain saturated, unsaturated, acetylenic and steroidal alcohols could all be oxidised with dimethyl sulfoxide-oxalyl chloride in high yields under mild conditions. 

Rodgman, A., L.C. Cook, and G.W. Young The analysis of cigarette smoke condensate. XVI. Normal long-chained primary alcohols RDR, 1960, No. 22, July 1, see www.rjrtdocs.com 500934833 -4847. 

Sulphosuccinic acid esters should be grouped into mono- and diesters. The first step of the monoester sulphosuccinate synthesis is the esterification of a hydroxyl-bearing stock material by maleic acid anhydride. As stock materials, long-chain primary alcohols, ethoxylated alcohols, ethoxylated alkylphenols, alkanolamides, ethoxylated alkanolamides, or monoglycerides are generally used [10, p. 405 ff 75, 76]. 

Bi Y, Zhou M, Hu H et al. (2001) Oxidation of long chain primary alcohols to acids over the quaternary ammonium peroxotungstophosphate catalyst system. React Kin Catal 72(l) 73-82... 

Oxidation of different substrates. We found (Vorobjeva, 1959) that glycerol can be used as a sole carbon source by P. jensenii only under aerobic conditions. If fumarate was added to minimal medium, then glycerol fermentation proceeded under anaerobic conditions with fumarate acting as an electron acceptor. Propionibacteria can oxidize compounds more reduced than glycerol, namely, alkanes and long-chain primary alcohols (Table 3.1). Oxidation of hydrocarbons is suppressed by the inhibitors of cytochrome oxidases, NaNa (10 M) and KCN (10" M), respectively, by 88 and 96%, which is similar to the degree of inhibition observed for glucose oxidation by P. pentosaceum. 

Reagent used in the ms detn. of the branching points in long-chain primary alcohols. Cryst. (pet. ether). V. sol. H2O, most org. solvs., spar. sol. pet. ether. Mp 24.6°. Bp 245°, Bp,2 133°. Spar, steam-volatile. Forms a... 

Method 2. Place a 3 0 g. sample of the mixture of amines in a flask, add 6g. (4-5 ml.) of benzenesulphonyl chloride (or 6 g. of p-toluenesulphonyl chloride) and 100 ml. of a 5 per cent, solution of sodium hydroxide. Stopper the flask and shake vigorously until the odour of the acid chloride has disappeared open the flask occasionally to release the pressure developed by the heat of the reaction. AUow the mixture to cool, and dissolve any insoluble material in 60-75 ml. of ether. If a solid insoluble in both the aqueous and ether layer appears at this point (it is probably the sparingly soluble salt of a primary amine, e.g., a long chain compound of the type CjH5(CH2) NHj), add 25 ml. of water and shake if it does not dissolve, filter it off. Separate the ether and aqueous layers. The ether layer will contain the unchanged tertiary amine and the sulphonamide of the secondary amine. Acidify the alkaline aqueous layer with dilute hydrochloric acid, filter off the sulphonamide of the primary amine, and recrystaUise it from dilute alcohol. Extract the ether layer with sufficient 5 per cent, hydrochloric acid to remove all the tertiary amine present. Evaporate the ether to obtain the sulphonamide of the secondary amine recrystaUise it from alcohol or dilute alcohol. FinaUy, render the hydrochloric acid extract alkaline by the addition of dilute sodium hydroxide solution, and isolate the tertiary amine. 

Primary alcohol sulfates are half esters of sulfuric acid. These substances are relatively simple organic molecules and have been known for a long time. The first alcohol sulfate was prepared by Dumas in 1836 [1] but long-chain alcohol sulfates were not used as surfactants until the 1930s [2]. 

In practice mixtures of primary and secondary esters are always obtained. A strong influence on the forming of primary esters is exerted by water in the reaction mixture which can come from traces of water in the alcohol as well as from P4O10. Long-chain alcohol also leads to a higher proportion of monoalkyl esters. 

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