Imidazoline-type

The incorporation of metal salts of amphoteric surface active agents (Mostat Series) as internal antistatic agents in polypropylene fibers has been reported (95). Metal salts of alanine, amidoamine, and imidazoline-type amphoteric surface-active agents show excellent performance as internal antistatic agents and also improve the dyeing ability of the fibers with acid dyes. 

The direct reaction of long-chain carboxylic acids and ethylenediamine or polyamines catalysed by sulphuric or toluenesulphonic acid gives a mixture of amidoamine, diamide and imidazoline-type compounds of the formula ... 

Here the alkyl part originates generally of coconut or tallow fatty acids. If methyl fatty acids or glycerides are the precursors, the liberated methanol is separated whereas glycerol is generally retained in the final product. Similar betainic structures, along with imidazoline-type amphoterics, occur as condensation products of fatty imidazolines and chloroacetic acid, as mentioned above. 

The separation of imidazoline-type cationics on a column (150x4.6 mm i.d.) of 3 micron Develosil ODS-3 with 0.1 M sodium perchlorate in methanol/acetonitrile/deionised water (60 60 5 by volume) as mobile phase and UV detection at 240 nm is described in [33]. Separation of different chain length alkyl substitution is demonstrated. 

In water flooding, the same types of inhibitors as described for primary production are currently used. The most effective and most frequently used are the quaternary ions of the fatty or the imidazoline types. They are also good bactericides and dispersive agents. Combination of amino-methylene phosphonate and zinc salts have been used successftdly in circulating water systems and have provided more effective protection than the inorganic phosphate-zinc salts. Organic sulfonates have recently been introduced into practice. 

Cation SF-10 [Sanyo Chem. Ind.j Chem. Descrip. Alkyl imidazoline type quat. compd. 

Kawase, J., K. Tsuji, Y. Yasuda, K. Yashima, Amphoteric surfactants by LC with post-column detection. II Imidazoline-type amphoteric surfactants derived from sodium chloroacetate, J. 

Although acetonitrile is one of the more stable nitriles, it undergoes typical nitrile reactions and is used to produce many types of nitrogen-containing compounds, eg, amides (15), amines (16,17) higher molecular weight mono- and dinitriles (18,19) halogenated nitriles (20) ketones (21) isocyanates (22) heterocycles, eg, pyridines (23), and imidazolines (24). It can be trimerized to. f-trimethyltriazine (25) and has been telomerized with ethylene (26) and copolymerized with a-epoxides (27). 

Many of the surfactants made from ethyleneamines contain the imidazoline stmcture or are prepared through an imidazoline intermediate. Various 2-alkyl-imidazolines and their salts prepared mainly from EDA or monoethoxylated EDA are reported to have good foaming properties (292—295). Ethyleneamine-based imida zolines are also important intermediates for surfactants used in shampoos by virtue of their mildness and good foaming characteristics. 2- Alkyl imidazolines made from DETA or monoethoxylated EDA and fatty acids or their methyl esters are the principal commercial intermediates (296—298). They are converted into shampoo surfactants commonly by reaction with one or two moles of sodium chloroacetate to yield amphoteric surfactants (299—301). The ease with which the imidazoline intermediates are hydrolyzed leads to arnidoamine-type stmctures when these derivatives are prepared under aqueous alkaline conditions. However, reaction of the imidazoline under anhydrous conditions with acryflc acid [79-10-7] to make salt-free, amphoteric products, leaves the imidazoline stmcture essentially intact. Certain polyamine derivatives also function as water-in-oil or od-in-water emulsifiers. These include the products of a reaction between DETA, TETA, or TEPA and fatty acids (302) or oxidized hydrocarbon wax (303). The amidoamine made from lauric acid [143-07-7] and DETA mono- and bis(2-ethylhexyl) phosphate is a very effective water-in-od emulsifier (304). 

Many mercaptoazoles exist predominantly as thiones. This behavior is analogous to that of the corresponding hydroxyazoles (c/. Section 4.02.3.7). Thus oxazoline-, thiazoline- and imidazoline-2-thiones (521) all exist as such, as do compounds of type (522). However, again analogously to the corresponding hydroxyl derivatives, other mercaptoazoles exist as such. 5-Mercaptothiazoles and 5-mercapto-l,2,3-triazoles (523), for example, are true SH compounds. 

Improved high-pressure liquid chromatography (HPLC) methods have been developed for the analysis of quaternary salt type corrosion inhibitors in brine waters [400]. However, these methods are not suitable for imidazolines and amido-amines. A method based on fluorescence detection has been described for the quantitative analysis of the imidazoline- and amido-amine-type corrosion inhibitors in both oil field water and crude oil samples by HPLC [1174]. 

Water-soluble corrosion inhibitors are necessary to prevent corrosion of the pipe walls, joints, pumps, and collection stations. An ampholytic, substituted imidazoline has been described for inhibiting corrosion in such systems [297]. This type of corrosion inhibitor is intended for continuous treatment. 

R. M. Matherly, J. Jiao, J. S. Ryman, and D. J. Blumer. Determination of imidazoline and amido-amine type corrosion inhibitors in both crude oil and produced brine from oilfield production. In Proceedings Volume. 50th Annu NACE Int Corrosion Conf (Corrosion 95) (Orlando, FL, 3/26-3/31), 1995. 

Some amphoteric softeners such as amino acids (10.237) and sulphobetaines (10.238) are more effective and durable than the nonionic types but less durable than the cationics moreover, they tend to be expensive. Other amphoteric types include the zwitterionic forms of quaternised imidazolines (10.239) long-chain amine oxides (10.240) also exhibit softening properties. 

Phosphino-imidazoline ligands of this type were originally synthesized by Bu-sacca and coworkers and used in an enantioselective Heck reaction [28]. 

In many applications nowadays it is essential to link a mass spectrometer to the gas chromatography in order to achieve positive identification and sensitivity of analysis. Some 12 types of compounds are listed in Table 1.11(a) which are based on the application of this technique, viz. polyaromatic hydrocarbons, polychlorobenphenyls, dioxins, chloro, carbamate and triazine types of herbicides and pesticides, Diazinon, Dicamba, Imidazoline and Cyperquat herbicides and herbicide pesticide mixtures. 

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]. 

One type of cationic surfactant was the fatty acid derivatives of polyamines. The properties of the derivatives of fatty acids and ethylenediamine have been described in the literature (7-9). It appeared from these reports that the 2-alkyl-2-imidazolines would not impart sufficient hydrophobicity to soils. However, the analogous series of homologous compounds from the fatty acids and diethylene-triamine (BETA) appeared likely to do so because of their higher molecular weight. 

Imidazolin-2-ylidenes of type 5 are normally obtained as colorless, diamagnetic, crystalline solids with surprisingly high melting points. In the absence of air and moisture, they exhibit a remarkable stability and even some air-stable derivatives... 

Additional factors which lead to an increased stability of the carbene complexes towards reductive ehmination are the type of NHC ligand and the NA -substitution pattern. The stability of NHC complexes depends strongly on the electronic situation at the carbene center. The oxidative addition of p-tolyl chloride to linear Pd° complexes bearing two unsaturated imidazolin-2-ylidenes (type 5, Fig. 6) or two saturated imidazolidin-2-ylidenes (t3q>e 7, Fig. 6) proceeds readily. The Pd complex with the imidazolin-2-yhdene ligands is stable, while the one with the imida-zolidin-2-ylidene ligands reductively ehminates the C2-arylated imidazolidinium salt [134]. 

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