Quaternary ammonium betaines

The Pt-catalyzed hydrosilylation of trimethyl silane and alkenols or alkenyl-polyethers lead to nonionic silane surfactants, whereas the addition of allylglycidyl ether to trimethylsilane results in a precursor for ionic derivatives. The epoxy group is highly reactive towards nucleophilic agents and can be easily transformed into quaternary ammonium, betaine, or sulfonate complexes. Additionally, cation-anion complexes can be formed by the transformation of two equivalents of epoxy silane with one equivalent of trialkyl ammonium hydrogen sulfite. The reaction of hydroxyalkyltrimethylsilane... 

Quaternary ammonium betaines possessing an anion moiety have emerged as Bronsted base catalysts. The C2-symmetric axially chiral ammonium betaine 177 deprotonates the a-substituted a-nitrocarboxylates (176) to form a structured ion pair that reacts with imines (173) to furnish the corresponding anti-Mannich... 

The threat of accidental misuse of quaternary ammonium compounds coupled with potential harmful effects to sensitive species of fish and invertebrates has prompted some concern. Industry has responded with an effort to replace the questionable compounds with those of a more environmentally friendly nature. Newer classes of quaternaries, eg, esters (206) and betaine esters (207), have been developed. These materials are more readily biodegraded. The mechanisms of antimicrobial activity and hydrolysis of these compounds have been studied (207). AppHcations as surface disinfectants, antimicrobials, and in vitro microbiocidals have also been reported. Examples of ester-type quaternaries are shown in Figure 1. 

Berberine, 162, 169, 170, 171, 287, 328, 329, 331, 344, 345, 631 Berberine, quaternary ammonium bases from tetrahydro-derivative, 337 Berberine and related bases, pharmacological action, 345 syntheses, 334 Berberineacetone, 333 cptBerberine, 297 profoBerberine, 336 4-Berberines, 335 Berberinium hydroxide, 333 Berberinol, 333 Berberis spp., 328, 331, 346 Berberoline, 332 Berberonic acid, 507 Berberrubine, 329, 343 Berbine, 336 Betaine, 518 Bicucine, 170, 209... 

Betaine, a quaternary ammonium compound, has been isolated... 

Therefore, a C13-AE, a cationic (quaternary ammonium) surfactant (quat), an amphoteric Ci2-alkylamido betaine, and the non-ionic fatty acid diethanol amide (FADA) as presented with their FIA-MS spectra in Fig. 2.5.12(a)-(d) were analysed as pure blends and as mixtures always obtained from two blends in FIA-MS multiple ion detection mode (MID). Mixtures as well as pure blends contained identical concentrations of surfactant homologues. For AE quantitation the mass traces of all A m/z 44 equally spaced homologues (m/z 306-966) of the C13-AE were recorded. The cationic (quaternary ammonium) surfactant, the amphoteric Ci2-alkylamido betaine, and the non-ionic FADA were quantified recording the mass traces at m/z 214 and 228, or 184, 212, 240, 268, 285, 296, 313, 324 and 341, or 232,260, 288, 316 and 344, respectively. 

To recognise ion suppression reactions, the AE blend was mixed together either (Fig. 2.5.13(a) and (b)) with the cationic quaternary ammonium surfactant, (c, d) the alkylamido betaine compound, or (e, f) the non-ionic FADA, respectively. Then the homologues of the pure blends and the constituents of the mixtures were quantified as presented in Fig. 2.5.13. Ionisation of their methanolic solutions was performed by APCI(+) in FIA-MS mode. The concentrations of the surfactants in the mixtures were identical with the surfactant concentrations of the blends in the methanolic solutions. Repeated injections of the pure AE blend (A 0-4.0 min), the selected compounds in the form of pure blends (B 4.0—8.8 min) and their mixtures (C 8.8— 14.0 min) were ionised and compounds were recorded in MID mode. For recognition and documentation of interferences, the results obtained were plotted as selected mass traces of AE blend (A b, d, f) and as selected mass traces of surfactant blends (B a, c, e). The comparison of signal heights (B vs. C and A vs. C) provides the information if a suppression or promotion has taken place and the areas under the signals allow semi-quantitative estimations of these effects. In this way the ionisation efficiencies for the pure blends and for the mixture of blends that had been determined by selected ion mass trace analysis as reproduced in Fig. 2.5.13, could be compared and estimated quite easily. 

Polyethers, alkanolamides, alkyls, alkylethoxylates, amines, benzyls, carbohydrates, esters, perfluoroalkyls Alkyl-, amidoimidazoline- and carboxy-quaternary ammonium salts Betaines, phosphobetaines, sulfobetaines... 

A broad range of information pertaining to the toxicity of several classes of surfactants including anionic (linear alkylbenzene sulfonates (LAS), alkylether sulfates (AES), alkyl sulfates (AS), non-ionic (alkylphenol ethoxylates (APEO)), cationic (ditallow dimethyl ammonium chloride (DTDMAC)—a group of quaternary ammonium salts of distearyl ammonium chloride (DSDMAC)) and amphoteric surfactants (alkyl-betaines) is available. Several reviews of the scientific literature have been published [3-5,20]. 

A compound prepared and first described as nicotinium dichromate (NDC) by Palomo et al.,379 was later shown by X-ray-crystal analysis380 to be a betainic mixed anhydride of nicotinic and chromic acid (NACAA). Because of its unique structure, it deserves a close scrutiny of its oxidative properties.381 Replacement of the chloride anion in the quaternary ammonium resin, Dowex 1-X8, for the dichromate anion, leads to a polymer supported dichromate, which is able to make selective benzylic oxidations.382 Finally, poly[vinyl(pyridinium dichromate)] (PVPDC), a polymeric analogue of PDC, must be mentioned whose use in the oxidation of alcohols allows for a very easy work-up.383... 

Sulphate Sulphonate Ether sulphate Ether phosphate Ether carboxylate Carboxylate Primary ammonium Secondary ammonium Tertiary ammonium Quaternary ammonium Amine oxide Betaine... 

Tank additives Quaternary ammonium compounds Betaines Dispersants/emulsifiers... 

Quaternary ammonium compounds are important as osmoprotectants in times of water deficiency and cold stress, as well as being constituents of membrane phospholipids, p-Alanine and phosphoethanolamine are each methylated three times on their nitrogens to produce the products P-alanine betaine and phosphocholine, respectively (Fig. ll.l).24"27 An example of O-methylation and N-methylation occurring on the same molecule can be found in the indole alkaloid vindoline from Catharanthus roseus (Fig. 11.1) 28,29... 

Amine products 63 amines, oxides, betaines, quaternary ammonium compounds,... 

Tertiary amines, such as trimethylamine or pyridine, react at low temperature to give the quaternary ammonium derivatives, which may result in the formation of stable betaines, e.g. 3 and 4. ... 

Treatment of the quaternary ammonium salt PhC=CCH2NMe2CH2COPh Br" with sodium hydroxide gives, inter alia, the betaine (98). Controlled-potential electrolysis of 7-nitro-ketones on a mercury cathode yields 1-pyrroline 1-oxides, pyrrolines, or pyrrolidines, according to conditions thus the oxide (99) is obtained from the compound 02NCMe2CHPhCH2C0Ph. The pyrrolinone (101) results from autoxidation of the furan derivative (100). Irradiation of the amide (102) leads to the pyrrolidinone (103) by an unprecedented [1,6] shift of hydrogen. " ... 

FMB. [Huntington Labs] Quaternary ammonium chlorides, fatty alkanol-amides, or betaines for fornuilation of disinfectants, sanitizers, fungicides, water treatment microbiocides, swimming pool algicides preservative for pharmaceuticals. 

Adma . [Ed I] AO l dimethyl amines intenneidiates for quaternary ammonium compds., amine oxides and betaines. 

The basic nitrogen atom (Nb) of strychnine is tertiary for quaternary alkylstrychninium salts result from reaction with molar proportions of alkyl halides (18, 208). The alkylstrychnines (2, 4, 47, 208, 256) result from fission of the lactam grouping and betaine formation with the quaternary ammonium hydroxide grouping. The secondary amine (NgH) of methylstrychnine (C2oH220(Nb CH3) (NaH) (CO2") may be further methylated with the formation of dimethylstrychnine (C20H22O) (NaCHa) (Nb CHa) (C02 ) (2, 47), or if it is heated with mineral acid lactamization results in the formation of methylstrychninium salts (47). 

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