N-alkyl-betaine

Three homologues in which n = 8 (CsBMT), 10 (CioBMT), and 12 (C12BMT) were synthesized by a procedure similar to that for the N-alkyl-betaines. Here, the N-methyl benzyl amine and sodium salt of 2-chloro-ethanesulfonic acid were refluxed in 95% methanol for two days. 

In Figure 1, the log of the cmc is shown as a function of the number of carbon atoms in the hydrocarbon chain, n, . It is clear that the nonionic surfactants (hexaethyleneglycol alkyl ethers) and the zwitterionic surfactants (N-alkyl betaines) exhibit linear relations with similar slopes of about -0.5... 

G(CH2) thus calculated is -705 cal/mol and -657 cal/mol for hexaethyleneglycol alkyl ethers and N-alkyl betaines, respectively, as shown in Table 1. 

These are surfactants containing both cationic and anionic groups [10]. The most common amphoterics are the N-alkyl betaines, which are derivatives of trimethyl glycine (CH3)3NCH2COOH (thatwas described as betaine). An example of a betaine... 

Fig. 4. Variation of In(cmc) versus hydrocarbon chain length at 25 °C for various surfactants in aqueous media (A) n-alkyl hexa-oxyethylene glycol monoethers [19]. (B) n-alkylsulfinyl alcohols [20], (C) n-alkyl glycosides [19], (D) n-alkyltrimethylammoniurn bromides in 0.5 M NaBr [17,21], (E) n-alkyl betaines [221, (F) alkyl sulfates in pure water [2]. (Redrawn with changes)...

The tertiary amine thus obtained was dissolved in absolute ethanol and was refluxed for two days with five molar percent excess of the appropriate bromoalkane (97% Humphrey Chemical, North Haven, Conn.). Solvent was removed and the residue in aqueous Na2C03 solution was extracted with hexane to remove any unreacted bromoalkane. Next, the N-alkyl N-benzyl N-methylglycine was extracted into chloroform from the aqueous layer. Solvent was stripped off and the crude material was recrystallized thrice from carbon tetrachloride and twice from THF/CHCl3 (60 40 v/v) mixture. The yields of the purified betaines were about 75% of the theoretical. 

The methyl and benzyl derivatives (289 R = Me, PhCH2 R = H) were described by Claus and Howitz in 1891. Their preparation involves N-alkylation of 6-hydroxyquinoline and base hydrolysis to the quaternary hydroxide which is then desiccated, giving the hygroscopic betaines 289. ° The 2-phenyl derivative (289 R = Me, R = Ph) has been similarly prepared. With methyl iodide, the phenol betaine (289 R = Me, R = H) gives Af-methyl-6-methoxyquinolinium iodide. ... 

During investigations on the carbonyl-assisted decarboxylation of N-alkylated ot-amino acids, Rizzi found that azomethine ylide intermediates are involved in the decarboxylative condensation (70JOC2069). Heating sarcosine and benzophenone at 170°C (or benzaldehyde at 150-170°C) gave 3-methyl-2,2,5,5-tetraphenyloxazolidine, which corresponds to the cycloadduct of azomethine ylide 98 to the carbonyl compound. This sequence may involve the initial formation of iminium carboxylate betaines and subsequent decarboxylation to generate nonstabilized azomethine ylides [Eq. (15)]. This... 

Beichardt (1965). Molar trmisition energies from the visible spectrum of pyridinium N-phenol betaines in solvents. Dimroth et al. (1963). Molar transition energies from spectrum of l-ethyl-4-methoxycarbonyl pyridinium iodide (Koso rer, 1958). From rates of Sj l solvolyses of alkyl halides and tosylates (Grunwald and Winstein, 1948). From ratio of endo to exo products in the Siels-Alder addition of cyclopentadiene to... 

Few investigations have been devoted to the degradation of alkylamines although there has been considerable interest in the metabolism of trimethy-lamine, choline, and glycine betaine as a source of methane in marine sediments (King 1984). Two aspects of the metabolism of N-alkyl compounds may be used as illustration. 

N-(3-Cocoamidopropyl)-N,N-dimethyl-N-carboxymethyl betaine. Alkateric Cab-A Coco Amido pine Cocoamido-propylbetaine N-(3-Cocoamktopropyl)-N,N-dimethyl-N-carboxymethyl betaine N-(3-Cocoamidopropyl)-N,N-dimethyl-N-carboxymethylammonium hydroxide, inner salt N-(Coco alkyl) amido propyl dimethyl betaine N Cocoamidopiopyl)-N,N-dimethyl-N-carb-oxymethyl ammonium. 

Alkyl (C12-C14) acrylate. See Lauryl acrylate Alkyl (C12-C14) amine. See Lauramine Alkyl (C13-C15) amine. See C13-15 amine Alkyl (CsCis) dimethyl-3,4-dichlorobenzyl ammonium chloride. See Alkyl dimethyl, dichlorobenzyl ammonium chloride N-(Alkyl C10-C16)-N,N-dimethylglycine betaine. See Cl 2-14 alkyl dimethyl betaine Alkyl (C8, CIO) glycidyl ether. See Alkyl (C8-10) glycidyl ether... 

N, N-Dimethyl-N-dodecylglycine betaine. See C12-14 alkyl dimethyl betaine... 

Soyamidopropyl dimethyl glycine. See Soyamidopropyl betaine Soyamidopropyl ethyidimonium ethosulfate CAS 90529-57-0 EINECS/ELINCS 291-990-5 Synonyms N-Alkyl-(3-amidopropyl)-N,N-dimethyl-N-ethyl ammonium ethyl sulfate 1-Propanaminium, 3-amino-N-ethyl-N,N-dimethyl-, N-soya acyl derivs., ethyl sulfates Classification Quaternary ammonium salt Formula [RCO-... 

The sulfonamide betaine 26 was usefiil for the preparation of N-alkylated l,2,4-dithiazolidine-3,5-diones in cases were the traditional Mitsunobu conditions failed. ... 

Alkyl betaines (RCH2N (CH3)2COj), popular personal product surfactants owing to their mildness, show a characteristic doublet at 1640 and 1610 cm" due to the carboxylate group (Figure 10.26). There are also shifts in the CH3 stretching frequency owing to N. ... 

Amidopropyl betaines exhibit features that include all the bands referred to for alkyl betaines, plus typical secondary amide bands at 1640 and 1550 cm" (amide II). The spectrum also contains N-H stretches at 3300 and 3100 cm" (Figure 10.27). 

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