Reaction of Fatty Alcohols

Fatty aldehydes are formed selectively by dehydrogenation of the corresponding fatty alcohol using copper chromite catalysts in slurries or fixed beds. Operation is at 250-350T and a pressure of 1 atm or less to give an equilibrium conversion to about 30% aldehyde. 

Comment Direct hydrogenation of the fatty acid with recycled fatty alcohol to produce ester as the first stage of reaction. Hydrogenation of the methyl ester of the fatty acid. Ester produced directly from the fatty acid or tram-esterification of the triglyceride. 

Fatty amines are formed by the dehydration of the fatty acid ammonium salts to give nitriles, which are then hydrogenated to amines. Amines are also formed by ammination of fatly alcohols. 

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A mixture of monolauryl phosphate sodium salt and triethylamine in H20 was treated with glycidol at 80°C for 8 h to give 98% lauryl 2,3-dihydro-xypropyl phosphate sodium salt [304]. Dyeing aids for polyester fibers exist of triethanolamine salts of ethoxylated phenol-styrene adduct phosphate esters [294], Fatty ethanolamide phosphate surfactant are obtained from the reaction of fatty alcohols and fatty ethanolamides with phosphorus pentoxide and neutralization of the product [295]. A double bond in the alkyl group of phosphoric acid esters alter the properties of the molecule. Diethylethanolamine salt of oleyl phosphate is effectively used as a dispersant for antimony oxide in a mixture of xylene-type solvent and water. The composition is useful as an additive for preventing functional deterioration of fluid catalytic cracking catalysts for heavy petroleum fractions. When it was allowed to stand at room temperature for 1 month it shows almost no precipitation [241]. 

Polyglycol Ethers. Polyglycol ethers, produced by the reaction of fatty alcohol with ethylene oxide, constitute the most important class of nonionic surfactants. They possess good wetting properties, produce relatively low foam, and are highly effective at low temperature and low concentration. They are used as textile auxiliaries, in dishwashing liquids, degreasing products, and hquid cleaner formulations. 

Fatty alcohol sulfate of commerce is actually a neutralized salt primarily as sodium coco fatty alcohol sulfate. It is produced by the direct reaction of fatty alcohol with sulfur trioxide and subsequently neutralized with caustic soda, according to the following reactions ... 

Alkyl phosphates, also coco based, are formed by the reaction of fatty alcohol with phosphorous pentoxide. The product is a mixture of monoesters and diesters. Its sodium salt (MAP) is reportedly mild and is used in facial wash, such as Kao s Biore. Other uses are as antistatics in textile auxiliaries, corrosion inhibitors, surfactant additives for extreme pressure (EP) lubricants, and surfactant components in alkali and acid cleaners. Coco-based alkyl polyglycosides (APG) have been successfully produced and marketed by Henkel in the United States. The alkyl polyglycoside fuUy satisfies the demand for a mild surfactant and is completely biodegradable. 

The structures of some common nonionic surfactants are shown in Figure 3.2. Ethoxylated alcohols are produced from the reaction of fatty alcohols with ethylene oxide, which results in a broad distribution in the number of EO units per molecules. These surfactants are generally excellent detergents, very mild, and less sensitive to water hardness ions, and also act as solubilizers. A typical ethoxylated alcohol used in LDLDs has approximately 9 EO units and a carbon chain length distribution centered around Cll. 

Single-chain quaternary anunonium surfactants are prepared from the reaction of fatty alcohols or fatty acids with a secondary amine. The resulting tertiary amine then reacts with methyl chloride to provide quaternary anunonium chlorides. The most important is cetyl trimethyl ammonium chloride (CTAC), which has excellent substantivity and conditioning properties. 

Description. This class of surfactants includes alkyl phosphates and alkyl ether phosphates. These surfactants are produced by the reaction of fatty alcohols with two... 

Description. This class of surfactants covers ethoxylated or propoxylated alcohols. Ethoxylated alcohols (i.e., polyethyleneglycol or PEG ethers) are produced from the reaction of fatty alcohols with ethylene oxide (EO). Similarly, propoxylated alcohols (i.e., polypropyleneglycol or PPG ethers) are obtained with propylene oxide (PO). Due to the low hydrophilicity of propylene glycol, this group does not increase (and even decreases) the water solubility of the molecule. Therefore, the same surfactant molecule generally combines EO units to compensate for the hydrophobicity of PPG chains PEG proportion can be modulated in order to control the surfactant HLB (hydrophilic-lipophilic balance). 

In the context of RR, a. is the reaction of - fatty alcohols, - fatty amines, - fatty acids, - fatty acid ethanolamides and fatty acid esters of polyhydroxy compounds such as mono/diglycerides or sorbitol, with ethylene oxide (EO) or propylene oxide (PO). 

C. are made by reaction of fatty alcohol ethoxylates with chloroacetic acid in the presence of caustic soda or by direct oxidation of the ethoxylate. 

F. are manufactured by reaction of - fatty alcohols and their ethoxylates with P2O5, POCI3 or PCI3, followed by neutralization. 

These are usually prepared by reaction of fatty alcohols or alkoxylated fatty alcohols with polyphosphoric acid or phosphoric anhydride. They resist hydrolysis in alkaline solutions, have good biodegradability, and are more compatible with hypochlorite bleach than the corresponding ethoxylated nonionics. Many members of this class have excellent skin compatibility, and are used in cosmetics as emulsifiers. Commercial processes usually give a mixture of mono- and diesters, to which the name sesquiphosphate is sometimes given. The monoesters tend to have better detergency and are better foamers, while the diesters are better emulsifiers. Specialty products based on alkylphenolethoxylates are also available for industrial applications (3). 

In the Godrej-Lurgi process, olefins are produced by dehydration of fatty alcohols on alumina in a continuous vapor-phase process. The reaction is carried out in a specially designed isothermal multitube reactor at a temperature of approximately 300°C and a pressure of 5—10 kPa (0.05—0.10 atm). As the reaction is endothermic, temperature is maintained by circulating externally heated molten salt solution around the reactor tubes. The reaction is sensitive to temperature fluctuations and gradients, hence the need to maintain an isothermal reaction regime. 

The conversion of fatty alcohols is approximately 99%. The reaction product is then condensed and sent to a distillation column to remove water and high boilers. Typically, a-olefin carbon-number distribution is controlled by the alcohol composition of the reactor feed. The process is currentiy used to produce a-olefins from fatty alcohols. A typical product composition is at <5%, at 50—70%, C g at 30—50%, C2Q at <2%,... 

Esterification is one of the most important reactions of fatty acids (25). Several types of esters are produced including those resulting from reaction with monohydric alcohols, polyhydric alcohols, ethylene or propylene oxide, and acetjiene or vinyl acetate. The principal monohydric alcohols used are methyl, ethyl, propyl, isopropyl, butyl, and isobutyl alcohols (26) (see Esterification Esters, organic). 

Oxidation of C12-C14 n-paraffms using boron trioxide catalysts was extensively studied for the production of fatty alcohols.Typical reaction conditions are 120-130°C at atmospheric pressure. ter-Butyl hydroperoxide (0.5 %) was used to initiate the reaction. The yield of the alcohols was 76.2 wt% at 30.5% conversion. Fatty acids (8.9 wt%) were also obtained. Product alcohols were essentially secondary with the same number of carbons and the same structure per molecule as the parent paraffin hydrocarbon. This shows that no cracking has occurred under the conditions used. The oxidation reaction could be represented as ... 

Chlorosulfonic acid, particularly with batch operation, is best suited for production of a range of products on a relatively small scale. Chlorosulfonic acid is still used for the sulfonation of fatty alcohols, fatty alcohol/ethoxylates, and related detergent raw materials with OH groups available for the attachment of an S03H group. For example, the reaction of lauryl alcohol with chlorosulfonic acid illustrates for example the chemistry involved ... 

TABLE 3 Reaction Scheme of Fatty Alcohol Sulfation... 

Fats are, chemically, triglycerides and can be regarded as the esters produced by the reaction of fatty acids with the trihydric alcohol... 

Despite the fact that glycolic acid has been successfully used as an acyl donor in esterification reactions with fatty alcohols, there are few reports dealing with the enzymatic ROP of glycolide [139], On the other hand, cyclic diesters based on ethylene glycol have been polymerized successfully by lipase catalysis and afford AA-BB-typepolyesters [140, 141],... 

Sulfation is the generation of an oxygen sulfur(IV) bond, where the oxygen is attached to the carbon backbone, in the most controlled manner possible, using some form of sulfur dioxide moiety. When sulfating alcohols, the reaction is strongly exothermic, Examples of feedstocks for such a process include alkenes, alcohols, or phenols. Unlike the sulfonates, which exhibit excellent stability to hydrolysis, the alcohol sulfates are readily susceptible to hydrolysis in acidic media, The sulfation of fatty alcohols and fatty polyalkoxylates has produced a substantial body of commercial detergents and emulsifiers. 

Alkyl ethers of sucrose have been prepared by reaction with long-chain alkyl halides to provide mixtures of regioisomers and products of different degree of substitution.82,83 A similar reaction with chloromethyl ethers of fatty alcohols provides formaldehyde acetals.84,85 Alkenyl ethers of various carbohydrates, and notably of sucrose, can also be obtained by palladium-catalyzed telomerization of butadiene (Scheme 6).86 88 Despite a low-selectivity control, this simple and clean alternative to other reactions can be carried out in aqueous medium when sulfonated phosphines are used as water-soluble ligands. 

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