Natural sulfation, alcohols

A published account of laboratory batch sulfations of Alfol 1214 SP, Alfol 1216 SP, and natural coconut alcohol using chlorosulfonic acid at atmospheric pressure and 16 L/min dry air sparged through the reaction mixture to remove HC1 is available [42], The optimal conditions and the characteristics of the triethanolamine alcohol sulfates obtained are shown in Table 1. 

Sulfates and sulfated products include alcohol sulfates, ethoxyiated and sulfated alcohols ethoxyiated and sulfated alkylphcnols and sulfated natural oils and fats. 

Gardinol Type Detergents. A mixture of the sodium salts of sulfated fatty alcohols made by reducing the mixed fatty acids of coconut oil or of cottonseed oil, and of fish oils. Sometimes natural waxes such as spermaceti, wool fat, and beeswax are sulfaied directly. The mixture of the sulfated alcohols which goes by the commercial name "lau-ryl alcohol consists of about 15% mixed C, and C1 (octyl and decyl) alcohols. 40% C (lauryl or dodecyl) alcohol, 30% Cl4 (myristyl or tetradecyl) alcohol, and 15% mixed CK and C 8 (cetyl, Stearyl, and oleyl) alcohols. 

AESs are anionic surfactants made by sulfating alcohol ethoxylates, and the degree of ethoxyl-ation typically ranges from 1 to 4, but predominantly 2-3 moles of ethoxylation (EO) are used with both natural and synthetic alcohol sources. AES provides numerous benefits such as high solubility. 

Overview of New Technology in Petroleum AND Naturally Derived Alcohol Sulfates... 

Chem. Descrip. Sulfated alcohol Ionic Nature Anionic... 

Alkyl ether sulfates, also called alcohol ethoxysulfates, are prepared by addition of one to four oxyethylene groups to an alcohol which is then sulfated. Oxyethylation enhances water solubility and foaming over the analogous alcohol sulfate, giving a product useful in shampoos and in liquid and powdered detergents. The raw material for these products can be either natural fatty alcohols or primary or secondary synthetic alcohols, usually of C12-C18 chain length. The analogous alkylphenol ether sulfates are found in industrial applications. Ether sulfates are not as sensitive to water hardness as are other anionic surfactants. 

In a widely used industnal process the mixture of ethylene and propene that is obtained by dehydrogenation of natural gas is passed into concentrated sulfunc acid Water is added and the solution IS heated to hydrolyze the alkyl hydrogen sulfate The product is almost exclusively a sin gle alcohol Is this alcohol ethanol 1 propanol or 2 propanoH Why is this particular one formed almost exclusively" ... 

Poly(vinyl acetate) emulsions can be made with a surfactant alone or with a protective coUoid alone, but the usual practice is to use a combination of the two. Normally, up to 3 wt % stabilizers may be included in the recipe, but when water sensitivity or tack of the wet film is desired, as in some adhesives, more may be included. The most commonly used surfactants are the anionic sulfates and sulfonates, but cationic emulsifiers and nonionics are also suitable. Indeed, some emulsion compounding formulas require the use of cationic or nonionic surfactants for stable formulations. The most commonly used protective coUoids are poly(vinyl alcohol) and hydroxyethyl cellulose, but there are many others, natural and synthetic, which are usable if not preferable for a given appHcation. 

In 1932 the first household detergent based on synthetic surfactants was brought into the market under the name FEWA (Feinwaschmittel). The product was produced from fatty alcohol sulfate by Bohme Fettchemie in Chemnitz. The shortage of the necessary natural raw materials caused by World War II led to the development of products based on more readily available raw materials [2],... 

Alcohols used in the manufacture of alcohol and alcohol ether sulfates are obtained either by chemical treatment of fats and oils or by petrochemical processes from natural gas or crude oil. In either case the hydrocarbon chain ranging from 8 to 18 carbon atoms corresponding to the composition of coconut oil is the most desirable. 

The reaction of olefin sulfation and its possibilities has been extensively studied [3-10] and it was used to produce alcohol sulfates. Dry distillation of spermaceti gives palmitic acid and cetene-1, which can be sulfated with sulfuric acid to give cetyl-2 sulfate [11]. Other surfactants were obtained from olefins produced from natural substances, such as alcohol sulfates by sulfation of olefins from decarboxylation of oleic acid [12], by sulfation of olefins made by dehydrating hydroabietyl alcohol, by direct sulfation of abietyl alcohol [13,14], or by sulfation of natural terpenes [15]. 

The advance of sulfur trioxide as sulfating agent largely depended on advances in sulfonation/sulfation reactor development and changes in raw material quality. Undiluted sulfur trioxide cannot be used as a sulfating agent except in special cases where suitable equipment is used because of its violent nature. Sulfur trioxide diluted in an inert gas, usually air, when used in batch processes can cause excessive dehydration and dark-colored products. However, batch processes were used years ago and inert liquid solvents were often suggested or used to moderate the reaction. Inadequate reaction conditions lead to a finished product that can contain dialkyl sulfate, dialkyl ether, isomeric alcohols, and olefins whereas inadequate neutralization conditions can increase the content of the parent alcohol due to hydrolysis of the unstable acid sulfate accompanied by an increase of mineral sulfate. 

These are two chemically different groups of products which have distinct application fields. Both product groups are obtained by reacting maleic acid anhydride (MA) with hydroxyl group(s)-carrying molecules, followed by sulfation of the intermediate product, an ester. Whereas the diester types are mainly made from a few different branched and unbranched alcohols, the monoester are derived from a wide variety of raw materials fatty alcohols, fatty acid alkanolamides, ethoxylated fatty alcohols, fatty acid alkanolamides, their etho-xylates, and others. All these raw materials—with the exception of the branched chains—may be obtained from natural renewable resources. 

Tosylate derivatives are not usually found in nature, but sulfate derivatives of alcohols are common (52). They are formed by the reaction of an alcohol with sulfate, catalyzed by a sulfotransferase enzyme. 

Since FAS can be produced either from vegetable oil based or petrochemical-based fatty alcohol (Fig. 4.9), both types have been evaluated in a life-cycle analysis with a positive overall result for the natural based product. With vegetable-based fatty alcohol sulfate, the analysis starts with the harvesting of the oil fruits (palm kernels or coconuts) and their processing to isolate the desired plant oil. Subsequent transesterification and hydrogenation of the methyl ester intermediates lead to the fatty alcohols, which are finally sulfated to produce the desired product. Based on this analysis the environmental impact of vegetable oil based fatty alcohol sulfate compared with the petrochemical based product is as follows ... 

DETAILS - Nicotine is well Imown as the alkaloid extracted f rom tobacco, where it exists in a proportion of 2% to 8%, by weight. It is soluble in water and alcohol. Nicotine is very useful as a projectile poison due to its sticky nature. It works well by itself or as a binder for powdered poisons. It is available commercially in some parts of the country, notably the South, where it is used as an insecticide. The most common form is the sulfate (Black Leaf 40), but the free base is also available. It sometimes requires some search-... 

Monolayers are best formed from water-insoluble molecules. This is expressed well by the title of Gaines s classic book Insoluble Monolayers at Liquid-Gas Interfaces [104]. Carboxylic acids (7-13 in Table 1, for example), sulfates, quaternary ammonium salts, alcohols, amides, and nitriles with carbon chains of 12 or longer meet this requirement well. Similarly, well-behaved monolayers have been formed from naturally occurring phospholipids (14-17 in Table 1, for example), as well as from their synthetic analogs (18,19 in Table 1, for example). More recently, polymerizable surfactants (1-4, 20, 21 in Table 1, for example) [55, 68, 72, 121], preformed polymers [68, 70, 72,122-127], liquid crystalline polymers [128], buckyballs [129, 130], gramicidin [131], and even silica beads [132] have been demonstrated to undergo monolayer formation on aqueous solutions. 

The shift to oleochemicals has been supported by increasing environmental concerns and a preference by some consumers, especially in Europe, for materials based on natural or renewable resources. Although linear alkylbenzenesulfonates (LASs) are petrochemically based, alcohol ethoxylates, alcohol ethoxysulfates, and primary alcohol sulfates are derived from long-chain alcohols that can be either petrochemically or oleochemically sourced. There has been debate over the relative advantages of natural (oleochemical) vs synthetic (petrochemical) based surfactants. However, detailed analyses have shown there is litde objective benefit for one over the other. 

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