Ammonia sulfonates

Feuer and co-workers also nitrated ring-substituted toluenes to the corresponding arylnitromethanes with potassium amide in liquid ammonia. Sulfonate esters and NJ -dialkylamides undergo similar nitration the latter isolated as their a-bromo derivatives. Alkaline nitration of ethyl and ferf-butyl carboxylic esters with potassium amide in liquid ammonia yields both the a-nitroester and the corresponding nitroalkane from decarboxylation. ... 

The ratio of reactants had to be controlled very closely to suppress these impurities. Recovery of the acrylamide product from the acid process was the most expensive and difficult part of the process. Large scale production depended on two different methods. If soHd crystalline monomer was desired, the acrylamide sulfate was neutralized with ammonia to yield ammonium sulfate. The acrylamide crystallized on cooling, leaving ammonium sulfate, which had to be disposed of in some way. The second method of purification involved ion exclusion (68), which utilized a sulfonic acid ion-exchange resin and produced a dilute solution of acrylamide in water. A dilute sulfuric acid waste stream was again produced, and, in either case, the waste stream represented a... 

Propionic acid, C2H 02, and ammonia [7664-41-7], NH, are additives used to prevent mol ding of feed (5). Bentonite, hemiceUulose extracts, and lignin sulfonate are used to hold feed pellets together. 

All the sulfonic acid hydrazides are made from hydrazine or semicarbazide and the appropriate sulfonyl chloride in the presence of an HCl acceptor such as ammonia. 

Resorcinol Derivatives. Aminophenols (qv) are important intermediates for the syntheses of dyes or active molecules for agrochemistry and pharmacy. Syntheses have been described involving resorcinol reacting with amines (91). For these reactions, a number of catalysts have been used / -toluene sulfonic acid (92), zinc chloride (93), zeoHtes and clays (94), and oxides supported on siUca (95). In particular, catalysts performing the condensation of ammonia with resorcinol have been described gadolinium oxide on siUca (96), nickel, or zinc phosphates (97), and iron phosphate (98). 

An exception exists to the monobasic nature of sulfamic acid when it dissolves ia Hquid ammonia. Sodium, potassium, etc. add both to the amido and sulfonic portions of the molecule to give salts, such as NaSO NHNa. 

Sulfation andSulfamation. Sulfamic acid can be regarded as an ammonia—SO. complex and has been used thus commercially, always in anhydrous systems. Sulfation of mono-, ie, primary and secondary, alcohols polyhydric alcohols unsaturated alcohols phenols and phenolethylene oxide condensation products has been performed with sulfamic acid (see Sulfonation and sulfation). The best-known appHcation of sulfamic acid for sulfamation is the preparation of sodium cyclohexylsulfamate [139-05-9] which is a synthetic sweetener (see Sweeteners). 

The cleavage products of several sulfonates are utilized on an industrial scale (Fig. 3). The fusion of aromatic sulfonates with sodium hydroxide [1310-73-2J and other caustic alkalies produces phenohc salts (see Alkylphenols Phenol). Chlorinated aromatics are produced by treatment of an aromatic sulfonate with hydrochloric acid and sodium chlorate [7775-09-9J. Nitriles (qv) (see Supplement) can be produced by reaction of a sulfonate with a cyanide salt. Arenesulfonates can be converted to amines with the use of ammonia. This transformation is also rather facile using mono- and dialkylamines. 

Chemical and physical solvent losses can render a process uneconomical. Desirable solvents are good solvents for urea, poor solvents for CA, high boiling, and stable to pyrolysis intermediates, ammonia, oxygen, and heat. Although no perfect solvent has been identified, some solvents, eg, dinitriles (94), pyrrohdinones (95,96), and sulfones (97) largely meet these requirements. 

A.mina.tlon. Amination describes the introduction of amino groups into aromatic molecules by reaction of ammonia or an amine with suitably substituted halogeno, hydroxy, or sulfonated derivatives by nucleophilic displacement. Although reaction and operational conditions vary, the process always involves the heating of the appropriate precursor with excess aqueous ammonia or amine under pressure. 

Aminoanthraquinone and Related Compounds. l-Amiuoanthraquiuone [82-45-1] (17) is the most important iatermediate for manufacturiag acid, reactive, disperse, and vat dyes. It has been manufactured from anthraquiaone-l-sulfonic acid [82-49-5] (16) by ammonolysis of the sulfo group with aqueous ammonia ia the presence of an oxidising agent such as nitroben2ene-3-sulfonic acid. 

Instead of Hquid ammonia, aqueous ammonia is also used together with a polar aprotic solvent such as formamide (48). It is also prepared by sulfonating... 

Two substituents on two N atoms increase the number of diaziridine structures as compared with oxaziridines, while some limitations as to the nature of substituents on N and C decrease it. Favored starting materials are formaldehyde, aliphatic aldehydes and ketones, together with ammonia and simple aliphatic amines. Aromatic amines do not react. Suitable aminating agents are chloramine, N-chloroalkylamines, hydroxylamine-O-sulfonic acid and their simple alkyl derivatives, but also oxaziridines unsubstituted at nitrogen. Combination of a carbonyl compound, an amine and an aminating agent leads to the standard procedures of diaziridine synthesis. 

This sulfonate is cleaved with Bu4N 1 or ammonia. The group has been reported to suffer from stability problems upon storage and use. ... 

In conclusion, all results obtained thus far on this reaetion show that it is espeeially the 4-position in the 3-nitro-l,8-naphthyridines whieh is strongly favored toward the attaek of the earbanion of ehloromethyl phenyl sulfone. When position 4 is oeeupied by a substituent no reaetion oeeurs. Tliis behavior is in aeeordanee with the behavior observed in reaetions with liquid ammonia and liquid methylamine. 

A simple chemical proof of structure of the diaziridines is given by the synthesis of the same diaziridine 42 from cyclohexanone either using methylamine and hydroxylamine-O-sulfonic acid or using ammonia and methylhydroxylamine-O-sulfonic acid. ... 

Naphthol 1 is initially protonated at a carbon center of high electron density (C-2 or C-4). The cationic species 3 thus formed is stabilized by resonance it can add a bisulfite anion at C-3. The addition product can tautomerize to give the more stable tetralone sulfonate 4 the tetralone carbonyl group is then attacked by a nucleophilic amine (e.g. ammonia). Subsequent dehydration leads to the cation... 

Yosida et al. [41] found that p-t< rr-butylcalix[6]ar-ene can extract Cu from the alkaline-ammonia solution to the organic solvent. Nagasaki and Shinkai [42] described the synthesis of carboxyl, derivatives of calix-[n]arenes ( = 4 and 6) and their selective extraction capacity of transition metal cations from aqueous phase to the organic phase. Gutsche and Nam [43] have synthesized various substituted calix[n]arenes and examined the complexes of the p-bromo benzene sulfonate of p-(2-aminoethyl)calix[4]arene with Ni, Cu , Co-, and Fe. ... 

Rossi and Bunnett64 studied the chemical reductive cleavage of diphenyl sulfoxide, diphenyl sulfone and methyl phenyl sulfone under the action of potassium metal in liquid ammonia in the presence of acetone. The enolate ion is used to trap phenyl radicals formed eventually during the process, in order to determine whether one or two electrons are required for the mechanism of cleavage (Scheme 7). In all the runs, phenyl anion is... 

Finally, ion chromatography can be used to determine the a-sulfo fatty acid esters. The chromatographic column is a nonpolar poly sty rene/divinylbenzene column and the ion pair reagent is 0.005 M ammonia. In order to reduce the elution time, acetonitrile is added as a modifier with increasing concentration. This gradient technique makes it possible to separate simultaneously ester sulfonates and disalts by chain length. Determination is achieved by standards with defined chain length [107]. 

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