Fatty acids quaternary ammonium salts

Fatty acid quaternary ammonium salts (n-Hexadecyltiimethylammonium chloride)... 

Soaps and detergents are surfactants used in cleaning.260 Soaps are salts of fatty acids (e.g., sodium stearate). Detergents are salts of sulfonic acids, quaternary ammonium salts, tertiary amine oxides, ethylene oxide adducts of alcohols, and phenols.261 Their use in cleaning to replace chlorinated solvents262 was covered in Chap. 3, Sec. VII. (See also the use of hydrogen peroxide,263 ethyl lactate,264 and ultrasound265 to clean process equipment.) Some other environmental aspects of their use will be covered here briefly. 

The only cationic surfactant (Fig. 23) found in any quantity in the environment is ditallow dimethylammonium chloride (DTDMAC), which is mainly the quaternary ammonium salt distearyldimethylammonium chloride (DSDMAC). The organic chemistry and characterization of cationic surfactants has been reported and reviewed [330 - 332 ]. The different types of cationic surfactants are fatty acid amides [333], amidoamine [334], imidazoline [335], petroleum feed stock derived surfactants [336], nitrile-derived surfactants [337], aromatic and cyclic surfactants [338], non-nitrogen containing compounds [339], polymeric cationic surfactants [340], and amine oxides [341]. 

Carnitine is a vitamin-like quaternary ammonium salt, playing an important role in the human energy metabolism by facilitating the transport of long-chained fatty acids across the mitochondrial membranes. An easy, fast, and convenient procedure for the separation of the enantiomers of carnitine and 0-acylcarnitines has been reported on a lab-made teicoplanin-containing CSP [61]. The enantioresolution of carnitine and acetyl carnitine was enhanced when tested on a TAG CSP, prepared in an identical way [45]. Higher a values were reached also in the case of A-40,926 CSP [41]. 

A relatively new field is the use of flotation in wet textile processes [73]. The ( -potential of cotton fibres in aqueous solutions is negative, therefore they are effectively floated by cationics like quaternary ammonium salts, e.g. dodecyl trimethyl ammonium chloride. Sysilia et al. [74] have established, by measuring the electrokinetic potential, a clear rule between the positive surface charge of chromite and flotation efficiency. At low pH, chromite was effectively floated by fatty acid soaps, the ions of which are negatively charged under these conditions. The surfactant adsorption is reversible which is indicative of its physical nature. 

Other compounds containing nitrogen and used as antistatic agents are quaternary ammonium salts, quaternized amines, quaternized heterocycles obtained from imidazoline and pyridine, and amides of quaternized fatty acids. Some of these compounds can be utilized for PVC for example ... 

Cocamidopropyl trimethyl ammonium chloride. See Cocamidopropyl trimonium chloride Cocamidopropyl trimonium chloride Synonyms Cocamidopropyl trimethyl ammonium chloride 1-Propanaminium, N,N,N-trimethyl-3-[(1-oxococo-alkyl) amino]-, chloride Classification Quaternary ammonium salt Formula [RCONH(CH2)3N(CH3)2CH3] Cr, RCO-rep. coconut oil fatty acids Uses Antistat, hair conditioner in cosmetics, hair conditioner rinses Trade Name Synonyms Empigen CSC t[Huntsman Surf. Sciences http //www.huntsman.com/surface sciences] Cocam ine... 

CAS 68953-64-0 EINECS/ELINCS 273-222-0 Synonyms Minkamidopropyl dimethyl 2-hydroxyethyl ammonium chloride Quaternary ammonium compds., (hydroxyethyl) dimethyl (3-mink oil amidopropyl), chlorides Classification Quaternary ammonium salt Formula [RC0-NH(CH2)3N(CH3)2CH2CH20Hrcr, RCO- rep. fatty acid groups from mink oil Properties Clear amber liq. sol. in water, 70% ethanol, glycerin, propylene glycol insol. in min. oil, IPM cationic... 

Classification Quaternary ammonium salt Formula [RCO-NH(CH2)3N(CH3)2CH3CH2] CH3CH20S03 , RCOffi rep. mixt. of lanolin and isostearic fatty acid radicals Uses Antistat in cosmetics Quaternium-61 CAS 111905-55-6... 

CAS 112324-11-5 Synonyms 1-Propanaminium, N-(oxiranylmethyl)-N,N-dimethyl-3-amino-, N-rape-oil acyl derive., chlorides Rapeseedamidopropyl dimethyl epoxypropyl ammonium chloride Classification Quaternary ammonium salt Formuia [RCONH(CH2)3N(CH3)2CH2CHOCH2] Cr, RCO- rep. fatty acids from rapeseed oil Uses Antistat in cosmetics conditioner for conditioning shampoos and hair sprays Trade Name Synonyms Schercoquat ROEP [Scher http //www.scherchem.com]... 

Classification Quaternary ammonium salt Formula [RCONH(CH2)3N(CH3)2CH2CHOCH2rcr, RCO rep. fatty acids derived from wheat germ oil Uses Antistat in cosmetics Wheatgermamidopropyl ethyidimonium ethosulfate CAS 115340-80-2... 

Fatty amines and diamines can be used for corrosion inhibition in oil-producing wells. Typically, these products are dispersed as salts of organic acids such as fatty acids or petroleum sulfonic acids. Fatty amines and diamines have also been used as corrosion inhibitors in the transportation and storage of petroleum products. Quaternary ammonium salts, including dialkyldimethy-lammonium, monoalkyltrimethylammonium and mono-alkyldimethylbenzylammonium, are good corrosion inhibitors. 

The preparation of DEQ is well known in the patent art. The reaction of about two equivalents of fatty acid (or fatty acid methyl ester) with one mole of triethanolamine (followed by quater-nization by dimethyl sulfate) results in a mixture of mono-, di-, and triesteramines quaternary ammonium salts. U.S. Patent 5750492 and U.S. Patent application 2002/0025915A exemplify that by adjusting the reaction conditions (molar ratio of fatty acid fraction to tertiary amine, temperature, ratio of cis to trans isomer in the unsaturated fatty group) to limit the amount of triesterquat content, liquid softener concentrates with as high as 22-28% actives can be produced. Some other useful examples of liquid concentrates can be found in patents U.S. 545340 and U.S. 5574179. 

The most commonly used strategy to increase the interlayer spacing (Lagaly et al. 1986) is the chemical modification of the phyllosilicate surface by cationic exchange using the quaternary ammonium salts of long fatty acid chains. From this technique, different organomodified clays can be obtained. 

However, it was suggested that if the residual anions could be completely removed from the organoclays, the primary degradation pathway would switch to an elimination-type mechanism [16]. The Hofmann elimination of ammonium compounds was most probably the source of additional amounts of vinyl-type unsaturation found in melt-processed OMMT-PE relative to both the polymer control and the Na+MMT-PE samples [28]. On the other hand, the presence of alkenes was also explained by three possible routes of decomposition (i) pyrolysis of alkanes derived from the major component of the organic part, i.e., hydrogenated tallow (HT) (ii) pyrolysis of the tallow (unsaturated fatty acids used for the preparation of the quaternary ammonium salt) and (iii) decarboxylation of RCOO and RCO radicals [17, 29]. 

Quaternary ammonium salts of fatty acids are converted to methyl ester derivatives pyrolytically in the injection port of a gas chromatograph. Of a number of reagents which have been described for the purpose, it appears that trimethylsulfonium hydroxide is the most powerful and exhibits fewer side reactions it can be used for the simultaneous transesterification of lipids and esterification of free acids [144]. 

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