Alkylamines, oxidation

Wetting times of /V,/V-dimethy1-/ -alkyl amine oxides as a function of the alkyl chain length show a minimum with dimethyl dodecyl amine oxide (Table 3). Foam generation of dimethyl-/ -alkylamine oxides solutions show a maximum when the alkyl group contains 14 carbons. 

A liquid detergent for dishes, vegetables, and fruit comprises the sodium salt of a-sulfo coconut acid ethyl ester (20%), an alkylamine oxide (5%), citric acid (0.5%), ethanol (50%), and water [78]. 

Suds stabilizers (DW, HC) Give more suds when suds level is an important indicator of cleaning power Ability to lower the CMC of the surfactant system Alkanolamides Alkylamine oxides 0-5% 0-5%... 

Stereochemical control in the addition of Grignard reagents to chiral racemic lV-(2-phenylpr( yl-idene)alkylamine /-oxides (215) has been observed (equation 27). Diastereoselectivity is modest (216 217 = 2 1-5 1). The formation of hydroxylamines (216) as the major products is consistent with Felkin-Ahn Grignard addition (Figure 11). 

Rewominox. [RewoGmbH] Alkylamine oxide foam booster, antistat fw personal care i ods. 

Suds control agents. Components in the formulation that act to stabilize or suppress sudsing (foaming). For examples, alkylamine oxides can be added to promote or stabilize sudsing, whereas silicones can be added to suppress sudsing (defoaming). 

Highly ethoxylated amines and diamines have been recommended for demulsification of crude oil. Combinations of quaternary ammonium salts and amines oxides are useful for foaming and silt suspension. Coco alkyltrimethylammonium chloride and bis(2-hydroxy-ethyljcoco alkylamine oxide comprise the preferred combinations. Quaternary ammonium salts, including coco alkyltrimethylammonium chloride, are useful for preparing foamed oil-in-water emulsions, which can dissolve paraffins and asphaltenes without formation damage. The pyrolized amine salts of humic acid have been used in filtrate control additives. 

Ethoxylated alcohol Cij., Alcohol ether sulfate Fatty acid glucoamide Alkylamine oxide Betaine... 

CU2 (NH2CH2CH2)2N(0)CH3 2](C104)4 298 56 0.36 bridging alkylamine oxide suggested 74T9... 

Chem. Descrip. Alkylamine oxide Ionic Nature Cationic... 

Chem. Descrip. Cocoyl amido-alkylamine oxide Ionic Nature Nonionic/cationic... 

Acetaldehyde, first used extensively during World War I as a starting material for making acetone [67-64-1] from acetic acid [64-19-7] is currendy an important intermediate in the production of acetic acid, acetic anhydride [108-24-7] ethyl acetate [141-78-6] peracetic acid [79-21 -0] pentaerythritol [115-77-5] chloral [302-17-0], glyoxal [107-22-2], aLkylamines, and pyridines. Commercial processes for acetaldehyde production include the oxidation or dehydrogenation of ethanol, the addition of water to acetylene, the partial oxidation of hydrocarbons, and the direct oxidation of ethylene [74-85-1]. In 1989, it was estimated that 28 companies having more than 98% of the wodd s 2.5 megaton per year plant capacity used the Wacker-Hoechst processes for the direct oxidation of ethylene. 

Oxygen-Cont iiningAmines. This group includes amine oxides, ethoxylated alkylamines, l-(2-hydroxyethyl)-2-imidazolines, and alkoxylates of ethylenediamine. Oxygen-containing amines are steadily increasing in economic importance. 

Alkylamines react with leucoquinizarin in a stepwise manner to give l-alh anaino-4-hydroxyanthraquinone, and 1,4-diaLkylamino derivatives after air oxidation. Aromatic amines react similarly in the presence of boric acid as a catalyst. The complex formed (129) causes the less nucleophilic aromatic amines to attack at the 1-, and 4-positions. 

Complex nitrogen compounds are formed from the reaction of aLkylamines with ethylene oxide (61). Thus diethylamine and ethylene oxide react to yield diethylaminoethanol. The diaLkylarninoethanols can react with ethylene oxide to give amino poly(ethylene glycols) ... 

Intramolecular alkylnitrene addition to an alkenic moiety situated S,e to the electron deficient center has been utilized for the preparation of bi- and tri-cyclic aziridines (Scheme 11) (68JA1650). Oxidation of the primary alkylamine can be effected cleanly with NCS, LTA or mercury(II) oxide. 

Even the trivial decomposition of oxaziridines may have some importance. In the oxidation of s-alkylamines to ketones conversion to the Schiff base of 2-pyridinealdehyde was proposed, followed by peracid oxidation to the oxaziridine (295). Decomposition by alkali yields the ketone added excess acetone suppresses condensation of pyridinealdehyde with dialkyl ketone (75AJC2547). 

Other examples of nucleophilic attack on a furoxan ring leading to ring opening/recyclization are the formation of 1,2,3-triazole 1-oxides 198 from 4-alkylamino-3-nitrofuroxans 197 and alkylamines (Scheme 129). 3-Amino-4-nitrofurazan was observed as by-product (95MC194, 96CHE580, 96KGS675). 

It was clearly shown by NMR spectroscopy that the addition of ammonia or primary or secondary alkylamines at position 5 of the 1,2,4-triazine 4-oxides to give the adducts 89 is a kinetically controlled process, while addition at position 3 to form the ring-opening products 85 is a thermodynamically controlled process. 

Grignard reagents add to racemic AT-(2-phcnylpropylidene)alkylamine A-oxides 2 to afford hydroxylamines 3a and 3b in good yield (68-90%) but modest diastereoselectivity (d.r. 67 33 — 83 17)7. The major product 3a is the diastereomer predicted by Cram s rule. 1 shows the attack of the Grignard reagent according to the T elkin-Anh explanation of Cram s rule. 

RATE DATA FOR TFIE PERMANGANATE OXIDATION OF SOME ALKYLAMINES... 

The alkylamination of quinizarin (22) in the presence of copper salts has been studied by Matsuoka and co-workers.16 The reaction proceeds via oxidation by copper ion of 22 to quinizarinoquinone (29). 2-Alkylamino-quinizarin (25) was obtained in quantitative yield. The 1,2-ring-closure product (30) is obtained by the reaction of 22 with ethylenediamines in the presence of copper ions17 (Scheme 9). 

By contrast, alkylamination of naphthazarin (7) in the presence of sodium dithionite followed by oxidation gives l,4-bis(alkylamino)-5,8-naphthoquinone (31).18,19 However, Kikuchi and co-workers20 obtained isomeric l,5-bis(alkylamino)-4,8-naphthoquinone (32) from the reaction of leuco naphthazarin (33) with alkylamine They also isolated 5-alkylamino-leuco-naphthazarin (34) as an intermediate, which is further aminated at the 1-position to give 32. Bloom and Dudek21 have studied the structure of leuco aminonaphthoquinones and their tautomeric equilibria in solution. They concluded that the reaction of leuco naphthazarin (33) or the leuco compound (35) derived from l,5-diamino-4,8-naphthoquinone (36) with methylamine gives mixtures of l,4-bis(methylamino)-31 (R = Me) and 1,5-bis(methylamino)naphthoquinones 32 (R = Me) after oxidation of leuco aminonaphthoquinones (Scheme 10). Some of the structures of leuco aminonaphthoquinones are shown in Scheme ll.20... 

On 100% acrylic materials the quaternary ammonium retarders are used almost exclusively. Other types have been evaluated, however. For example, saturated alkylamines (RNH2 R = C10, C12, C14 and C16 hydrophobes) were found to be just as effective as the quaternary types although other factors, such as aqueous solubility at the optimal dyebath pH and resistance to subsequent discoloration, favour the quaternary compounds [34]- On the other hand, bis (hydroxyethyl) coco amine (12.10) had relatively little effect and the amphoteric carboxymethyldimethylcocoamine (12.11) none at all, although dimethyl-cocoamine oxide (12.12) was quite an effective retarder [34]- Other cationic compounds used [43,44] have included alkylpyridinium salts, imidazoles and imidazolinium salts, alkyldiamines, alkylpolyamines, as well as sulphonium and phosphonium derivatives. 

Alkylnickel amido complexes ligated by bipyridine have been prepared that undergo reductive elimination of V-alkyl amines (Equation (54)).207,208 Unlike the phosphine-ligated palladium arylamides, these complexes underwent reductive elimination only after oxidation to nickel(III). Thermally induced reductive elimination of alkylamines from phosphine-ligated nickel complexes appears to occur after consumption of phosphine by arylazides 209... 

More recently, reductive elimination of aryl ethers has been reported from complexes that lack the activating substituent on the palladium-bound aryl group (Equation (55)). These complexes contain sterically hindered phosphine ligands, and these results demonstrate how steric effects of the dative ligand can overcome the electronic constraints of the reaction.112,113 Reductive elimination of oxygen heterocycles upon oxidation of nickel oxametallacycles has also been reported, but yields of the organic product were lower than they were for oxidatively induced reductive eliminations of alkylamines from nickel(II) mentioned above 215-217... 

Arylidene alkylamines and diphenyl cyclopropenone gave rise to products 397-399, whose formation can be interpreted by means of oxidative secondary reactions of the 5 H-A2-pyrrolin-4-one 396 (R2 = H) initially generated252. ... 

Sydnonimines with alkylamine substituents at position N3 were shown to be considerably more potent donors of nitric oxide compared with analogs having alkyl or aralkyl groups at the same position <2004RCB2840>. 

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