Carboxylates fatty alcohol

There are two important methods for the synthesis of ether carboxylates from ethoxylated fatty alcohols ... 

Esters of ether carboxylic acids (propylated and/or ethoxylated) and fatty alcohols or ethoxylated fatty alcohols are described [40], prepared by esterification of the ether carboxylic acid and the alcohol with an acid catalyst like H2S04 or p-toluenesulfonic acid under vacuum and at a temperature of about 130°C. The purpose of these esters is to mainly use them in cremes and lotions with better conditioning and moisture controlling properties. 

Schulze [51] described an extensive study on C12-C14 ether carboxylic acid sodium salt (4.5 mol EO) in terms of surface tension, critical micelle concentration (CMC), wetting, detergency, foam, hardness stability, and lime soap dispersing properties. He found good detergent effect compared to the etho-xylated C16-C18 fatty alcohol (25 mol EO) independent of CaCl2 concentration, there was excellent soil suspending power, low surface tension, and fewer Ca deposits than with alkylbenzenesulfonate. 

Besides the usual alkyl ether carboxylates and amidether carboxylates some special types have been developed for use in cosmetic formulations. These are based on fatty alcohol propyl ether diols [113] and fatty alcohol diols [26]. 

Ether carboxylates are used not only in powdered detergents but in liquid laundry detergents for their hard water stability, lime soap dispersibility, and electrolyte stability they improve the suspension stability and rheology of the electrolyte builder [130,131]. Formulations based particularly on lauryl ether carboxylate + 4.5 EO combined with fatty acid salt and other anionic surfactants are described [132], sometimes in combination with quaternary compounds as softeners [133,163]. Ether carboxylates show improved cleaning properties as suds-controlling agents in formulations with ethoxylated alkylphenol or fatty alcohol, alkyl phosphate esters or alkoxylate phosphate esters, and water-soluble builders [134]. 

Highly concentrated ether carboxylic acids with a low degree of ethoxylation even at room temperature can give an esterification reaction with the non-converted nonionic, especially with the fatty alcohol, to several percentage points. The result may be that a too low value is found for the ether carboxylate content. This mistake in analysis can be avoided by saponification of the formed ester [238]. Two hundred to 300 mg matter and ca 100 mg NaOH were weighed in a 50-ml Erlenmeyer glass, heated with 20 ml ethanol under reflux, and after cooling supplied with water to 100 ml. Afterward a two-phase titration was carried out. 

The development of monoalkyl phosphate as a low skin irritating anionic surfactant is accented in a review with 30 references on monoalkyl phosphate salts, including surface-active properties, cutaneous effects, and applications to paste and liquid-type skin cleansers, and also phosphorylation reactions from the viewpoint of industrial production [26]. Amine salts of acrylate ester polymers, which are physiologically acceptable and useful as surfactants, are prepared by transesterification of alkyl acrylate polymers with 4-morpholinethanol or the alkanolamines and fatty alcohols or alkoxylated alkylphenols, and neutralizing with carboxylic or phosphoric acid. The polymer salt was used as an emulsifying agent for oils and waxes [70]. Preparation of pharmaceutical liposomes with surfactants derived from phosphoric acid is described in [279]. Lipid bilayer vesicles comprise an anionic or zwitterionic surfactant which when dispersed in H20 at a temperature above the phase transition temperature is in a micellar phase and a second lipid which is a single-chain fatty acid, fatty acid ester, or fatty alcohol which is in an emulsion phase, and cholesterol or a derivative. 

The pendant hydroxy groups of ethylene oxide-propylene oxide copolymers of dihydroxy and trihydroxy alcohols may be sulfurized to obtain a sulfurized alcohol additive. This is effective as a lubricant in combination with oils and fats [387,533]. The sulfurized alcohols may be obtained by the reaction of sulfur with an unsaturated alcohol. Furthermore, fatty alcohols and their mixtures with carboxylic acid esters as lubricant components [1286] have been proposed. 

H. Muller, C. P. Herold, and S. von Tapavicza. Use of selected fatty alcohols and their mixtures with carboxylic acid esters as lubricant... 

SEC-RI/UV has also been used to analyse some 26 thioorganotin compounds, organotin carboxylates and chlorides, essentially PVC stabilisers, and some of their main by-products and related compounds (thioesters and dithioesters, n-alkanes) [803]. Not all organotin chlorides were stable in the adopted analysis conditions. N, Ai -ethylene-bis-stearamide and -oleamide in common plastics (ABS, SAN, PUR, LDPE, PA6.6) can be analysed by SEC after derivatisation with trifluo-roacetic anhydride. SEC analysis of fatty alcohol ethoxy-lates (FAE), used as nonionic surfactants, has also been described [759]. 

Sulphates or sulphuric esters of the long-chain fatty acids were the first alternative to the carboxylates. They are essentially the half esters of sulphuric acid (9.9) the ester incorporating the cetyl hydrophobe (9.10) belongs to the important class of fatty alcohol sulphates. Such sulphates, using C8-C18 hydrophobes, are common. 

Naturally occurring fatty alcohols used in the fragrance industry are produced principally by reduction of the methyl esters of the corresponding carboxylic acids, which are obtained by transesterification of natural fats and oils with methanol. Industrial reduction processes include catalytic hydrogenation in the presence of copper-chromium oxide catalysts (Adkins catalysts) and reduction with sodium (Bouveault—Blanc reduction). Unsaturated alcohols can also be prepared by the latter method. Numerous alcohols used in flavor compositions are, meantime, produced by biotechnological processes [11]. Alcohols are starting materials for aldehydes and esters. 

Fatty Acids and Fatty Alcohols Fatty acids are traditionally meant as aliphatic unbranched monocarboxylic acids, either saturated or unsaturated, but with a chain length of 4 to 28 carbon atoms. Sometimes even shorter acyclic aliphatic carboxylic acids like acetic acid are named fatty acids, although they are not found in oils and fats [19]. 

Because the terminal hydroxyl of the carboxylic group of fatty alcohols and fatty acids, respectively, can act as an anchor for further transformation, it can be used for a variety of reactions not yet commercialized but with great possibilities (Figure 2.2.7) [27],... 

Examples of common hydrophobes include alkylphenol, fatty alcohol, paraffin, olefins, and alkylbenzene. Examples of common hydrophiles include ethylene oxide (EO), sulfates, sulfonates, phosphates, and carboxylic acid groups. Depending on the charged nature of the head group, surfactants are classified as ... 

Both carbon-carbon double bonds and the carboxyl group of fatty acids can be reduced, either together or separately depending on the reaction conditions. Catalytic reduction is an important industrial route to hardened fats, fatty alcohols, and fatty amines, using well-established technologies. 

Triacylglycerols, fatty acids, and esters can be reduced to aldehydes, alcohols, or hydrocarbons, the main application being the production of fatty alcohols. On a small scale, lithium aluminum hydride (in excess of stochiometric requirement) is a convenient reducing agent for the carboxyl group without affecting polyunsaturated chains. Industrially, catalytic hydrogenation is used and has been reviewed (79, 80). 

Crude montan wax (a mixture of esters of straight-chain saturated C26-C34 carboxylic acids) is a by-product of lignite and separated from lignite by an extraction process. Oxidative bleaching of black crude montan wax with hot chromosulphuric acid produces off-white, industrial montan wax acids. Esters of mono- and polyfunctional short-chain alcohols, esters of long-chain natural or synthetic fatty alcohols as well as complex esters are synthesized starting from montan wax acid [155]. 

Keywords solid-gas reaction, fatty alcohols, carboxylic acids... 

Polyoxyethylenated (POE) Fatty Alcohol Carboxylates (Alkyl Ether Carbox-ylates), R0(CH2CH20)xCH2C00M (x = 4, usually) Products of the reaction of the terminal OH group of an alcohol ethoxylate (AE) with sodium monochlor-oacetate. Less basic than soaps of comparable chain length, ascribed to the ether oxygen atom adjacent to the carboxylate group in the molecule. 

---