Fatty amides alkanolamides

Hlkanolamides. The fatty acid alkanolamides are used widely ia shampoo formulations as viscosity and lather builders. They are formed by the condensation of a fatty acid with a primary or secondary alkanolamine. The early amides were compositions of 2 1 alkanolamine to fatty acid. Available technology allows the formation of amides with a 1 1 ratio of these additives. These amides are classified as superamide types. The typical amide used ia shampoo preparations usually contains the mono- or diethanolamine adduct, eg, lauric diethanolamide [120-40-1] (see Amides, fatty acid). 

Alkanolamides, a special subclass of substituted amides used as surfactants, are produced by three principal methods the reaction of fatty amides with formaldehyde, fatty acids with hydroxyalkylamines, and fatty esters with hydroxyalkylamines (37). A fatty amide and formalin can be heated in the presence of sodium hydroxide to yield 70—95% substituted alkanolamides (38,39). 

Many primary fatty amides which are available from various manufacturers are Hsted in Table 3. In 1986 approximately 55,000 metric tons of amides and bisamides were produced world wide (58), the majority of which are bisamides, followed in volume by primary amides. Most of these products are shipped in sohd form in bag or dmm quantities. Major producers of primary fatty amides are Akzo, Glyco, Humko, and Sherex. Bisamides are produced by Akzo, Milacron, and Syntex. There are over 100 producers of alkanolamides in the world, most of which are small specialized manufacturers to a specific industry. GAP, Henkel, Sherex, and Witco are among the principal producers. The most widely used alkanolamides are the Ai,Ai-bis(2-hydroxyethyl) fatty amides, mostly produced from middle-cut coco fatty acids (6% capryflc, 7% capric, 51% lauric, 19% myristic, 9% palmitic, and 2% stearic acids). An estimated 77,000 metric tons of alkanolamide was produced worldwide in 1986 (59). 

Sulfated Acids, Amides, and Esters. Reaction with sulfuric acid may be carried out on fatty acids, alkanolamides, and short-chain esters of fatty acids. The disodium salt of sulfated oleic acid is a textile additive and an effective lime soap dispersant. A typical sulfated alkanolamide stmcture is CiiH23C0NHCH2CH20S03Na. Others include the sulfates of mono and diethanolamides of fatty acids in the detergent range. The presence of... 

Alkanolamides from fatty acids are environmentally benign surfactants useful in a wide range of applications. It was found that most lipases catalyze both amidation and the esterification of alkanolamides however, normally the predominant final products are the corresponding amides, via amidation, and also by esterification and subsequent migration [15]. Recently, an interesting example for the production of novel hydroxyl-ated fatty amides in organic solvents has been carried out by Kuo et cd. [16]. 

Condensates of ethylene oxides with an amide. Fatty acid alkanolamides are amides of alkylolamines and fatty acids. Certain members of this class exhibit detergency and others do not. The nondetergent materials are converted into detergents by condensation with ethylene oxide. 

Upamide. [UPI] Fatty acid alkanolamide or ethoxylated fatty amides. 

These surfactants are produced by reacting fatty acids or fatty methyl esters with ethanolamine or diethanolamine. With fatty acids, conventional amides (sometimes called Kritchevsky alkanolamides) are obtained that consist of approximately 50% amide, 25% unreacted diethanolamine and 25% of various by-products (the amine ester the amide ester, and the amine soap). With methyl esters, higher-active (90% amide) alkanolamides are produced these are known as super amides . 

Alkanolamides can also be produced by ethoxylating fatty amides. 

CAS 27883-12-1 56863-02-6 EINECS/ELINCS 260-410-2 Synonyms (9Z,12Z)-N,N-Bis (2-hydroxyethyl) octadeca-9,12-dien-1-amide N,N-Bis (2-hydroxyethyl)-9,12-octadecadienamide Diethanolamine linoleic acid amide Linoleic acid diethanolamide Linoleic diethanolamide 9,12-Octadecadie-namide, N,N-bis (2-hydroxyethyl)-Classification Fatty acid alkanolamide Definition Mixt. of ethanolamides of linoleic acid tonic Nature Nonionic Empiricai C.jHi NO,... 

The most common examples of this class are diesters of 2-ethylhexanol. However, there are commercial products which are monoesters, diesters, or mixtures of the two. The alcohol portion of the ester may be fatty alcohol, fatty acid alkanolamide, or ethoxylated fatty amine. They are typically synthesized by forming the ester or amide with maleic anhydride, followed by reaction of the alkyl fumarate with sodium bisulfite. The monoesters are often used in cosmetics and shampoos. 

As summarized in Table 10, fatty acid ethanolamide and ethoxylated fatty ethanolamide may be quantitatively analyzed by TLC on silica, using iodine vapor for visualization of the ethanolamide and Dragendorff reagent for the ethoxylated compounds, which are separated by chain length (57,58). Either silica gel impregnated with dodecanol or alumina plates allow differentiation of mono- and dialkanolamides (7). Reversed-phase systems will differentiate alkanolamides according to alkyl chain length (14). A 3-plate system allows determination of isopropanolamine and amide, mono-and diethanolamine and amide, and polydiethanolamide in commercial fatty acid alkanolamide surfactant (59). The latroscan technique (flame ionization detection) can also be used with multiple development to analyze these compounds (60). 

C ()-Ci8 fatty acid alkanolamide determination of iso-propanolamine and amide, mono-and diethanolamine and amide, polydiethanolamide... 

Significant quantities of amine and amide esters are formed by side reactions (9). In addition, with dialkanolamines, amide diesters, morpholines, and piperazines can be obtained, depending on the starting material. Reaction of dialkanolamines with fatty acids in a 2 1 ratio, at 140—160°C, produces a second major type of alkanolamide. These products, in contrast to the 1 1 alkanolamides, are water soluble they are complex mixtures of AJ-alkanolamides, amine esters, and diesters, and still contain a considerable amount of unreacted dialkanolamine, accounting for the water solubiUty of the product. Both the 1 1 and the 2 1 alkanolamides are of commercial importance in detergents. 

Superior to fatty acids as chemical intermediates in some applications. In the production of alkanolamides, esters can produce superamides, with more than 90% purity against fatty acids, which can only produce amides with a purity of 65-70% amides. 

Early experiments in the preparation of alkanolamides were begun by Kritchevs-ky (24, 25). It involves condensation reactions of fatty acids, triglycerides, esters, amides, anhydrides, and halides with an alkanolamine. The reaction was carried out at 100-300°C at atmospheric pressure. An important improvement was made by... 

There are at least four types of alkanolamide commercially available. The first is formed by reacting monoalkanolamine or dialkanolamine with fatty acids in a 1 1 ratio at elevated temperatures of 140-160°C. Signihcant quantities of the byproducts—amine esters and amide esters—are also formed. 

Along with monoethanolamides (I), isopropanolamides (II) and diethanolamides (III), synthesized analogously, have a practical importance. Purer fatty acid mono- and diethanolamides containing some ethoxylated amides could be prepared by the reaction of fatty acid amides with controlled amounts of ethylene oxide. Ethoxylation of fatty acid amides results in mixtures of mono- and diethanolamides as well as polyethoxylated alkanolamides. 

Fatty acid ethanolamides and isopropanolamides are solid or waxy products insoluble in water. Diethanolamides are usually pastes or liquids and show better dispersibility in water. In institutional and household formulations, shampoos, bath and shower preparations, fatty alkanolamides play the role of foam stabiliser, thickener, corrosion inhibitor, and ancillary agent that improves the skin compatibility of anionic surfactants. Undecylenic ethanolamide and undecylenic diethanolamide act as fungicides also [47]. Use of diethanolamine derivatives has legislative limitations today in some countries (but not its amides) because they are proved to be precursors of carcinogenic nitrosoamines. The probability of the nitrosoamine formation is assumed to increase in the presence of formaldehyde and formaldehyde-releasing preservatives [44-46]. 

Over 50% of the consumption of traditional blooming antistatic agents consists of ethoxylated amines and glyceryl monostearate (GMS), and much of the rest consists of alkyl sulfonates, fatty alkanolamides and amide ethoxylates. Films containing amide antistats usually pass the American Mil-B-81705C (commonly known as Mil spec) test for electrostatic dissipation when the film is a few days old, but not after three or four weeks. This has been attributed to the formation of crystallites of the antistatic agent. 

Alkanolamides are the reaction products of mono- or dialkanolamines with fatty acids or their esters to form the respective secondary or tertiary amides, examples of which are depicted in Scheme 1.8. " Monoalkanolamides can be prepared by the reaction of monoalkanolamines with triglycerides such as coconut or palm kernel oil as well as from fatty acids or their methyl esters. The reaction of MEA with triglyceride at temperatures of 140-160°C liberates glycerin as a by-product, and because of the stability of the secondary amide formed, the reaction can be driven to a very low ester content with only a slightly super-stoichiometric amount of MEA. 

Alkanolamides based on DEA are tertiary amides and are not as stable as MEA amides such that a significant amount of esters can remain in equilibrium with the amide. The ester amines and esteramides of DEA have undesirable performance properties, but these components can be reduced by utilizing an excess of DEA to drive equilibrium toward the amide form. The most common version is prepared by the reaction of 2 moles of DEA with 1 mole of coconut fatty add or ester to give the Kritchevsky or Ninol-type DEA amide, which is liquid at room temperature. Products made with slightly more than a 1 1 molar ratio of DEA to fatty acid or ester are referred to as superamides and at reaction temperatures of 140-160°C, the mixture contains high level of ester components and free amine. However, with sufficient time at storage temperatures <50°C, the composition will increase in amide and decrease in ester and free-amine components and thus can be aged into specification for free DEA and ester content. 

GAF CHEMICALS CORP. ALKAMIDE Fatty Alkanolamides (Continued) Super (1 1) Amides (Continued) ... 

Early experiments in the preparation of alkanolamides were begun by Kritchevsky (20, 21). It involves condensation reactions of fatty acids, triglycerides, esters, amides, anhydrides, and halides with an alkanolamine. The reaction was carried out at 100-300°C at atmospheric pressure. An important improvement was made by Meade (22), who made use of an alkali metal alkoxide as a catalyst at 100°C at atmospheric and slightly above atmospheric pressure. Fmther refinement was made by Tesoro (23), who conducted the reaction at 55-75°C and a vacuum of 4—8 kPa. Schurman (24) patented a continuous process for making alkanolamide, which makes use of a thin film reactor. It is claimed the short contact time in the reactor produces a high-purity alkanolamide (25). 

Type 2 1 (or Kritchevsky alkanolamide) is a mixture of mono- or dialkanolamide and free mono- or dialkanolamine. It results from the reaction of a fatty acid or ester with mono- or dialkanolamine, this last component being combined at a 2 1 molar proportion. Reaction residues in type 2 1 surfactants are free alka-nolamine, unreacted fatty acid, and ester-amide. 

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