Ammonium sulfonate

Figure 5. Sulfonium and ammonium sulfonates showing Preferential Enrichment or failing to show it. The superscripts on the compound names indicate the reference number.

Solubility of Phenolated Lignin Sulfonates. Since the presence of ammonium sulfonate moieties tends to confer water solubility, their disappearance should be reflected in a reduction of this characteristic. The extent of this effect was assessed by measuring the solubility of a stirred aliquot (1-4 g) of the 200 °C phenolysis product in water (200 mL). The resultant suspension was filtered and the residue dried for about 2 days at 22 °C to constant weight. The results obtained under a variety of reaction conditions are summarized in Table III. 

The use of aromatic sulfonates stems from their ability to assist the solution of organic substrates in an aqueous medium. This hydrotropic effect [270,450,451] is accentuated if a quarternary ammonium sulfonate, rather than an alkali metal sulfonate, is used. 

The sultone cycloadducts could be further manipulated by ring-opening with various nucleophiles, such as alcohols and amines, at the y-position [41]. When optically active (S)-(-)-a-methylbenzylamine reacted with the racemic sultone cycloadduct 76 in ethanol at room temperature, one of the diastereomeric ammonium sulfonates precipitated from the reaction mixture (Scheme 17). Although the absolute stereochemistry of 77 had not been determined, cyclization of optically pure 77 with phosphorus oxychloride gave an optically pure sultam 78. Formic acid debenzylation followed by base hydrolysis of the N-formyl group afforded the optically pure sultam 80 in good yield [40]. 

Compared to the metal salts the free polymeric acids are not highly or strongly associated. In fact, they can be dissolved in aliphatic and aromatic hydrocarbons in the absence of a polar cosolvent. The free acids tend to possess low strength and to be less stable thermally. In order to obtain useful products the free acids must be converted to their corresponding metal or ammonium sulfonates. 

N-Arylamidinium sulfonates (s. 2, 326) give almost quantitatively un-subst. amidinium sulfonates by heating in an atmosphere of NHg at 100-160°, with or without a solvent. This is a valuable method of preparation when poor yields are obtained directly from a cyanide and an ammonium sulfonate.—E N-o-Chlorophenylbenzamidinium benzene-sulfonate heated 5 hrs. in nitrobenzene at 140° — benzamidinium ben-zenesulfonate. Y 91.5%. (Many e. s. P. Oxley and W. F. Short, Soc. 1949, 449.)... 

Sulfonamides can in general be obtained very smoothly by treating sulfonyl chlorides with ammonia694 or dry, powdered ammonium carbonate.217,695 The reaction with ammonia is carried out in aqueous solution or better in an inert organic solvent in the cold it is advisable to use an excess of ammonia so as to avoid hydrolysis to the ammonium sulfonate or formation of the disulfonylamide, (RSC NH. 

Acid-catalysed esterification reactions in ILs have been extensively studied, and will be the main focus of this section. In 2001, Deng et al. first reported the synthesis of allq l acetate esters in an IL with concentrated sulfuric acid as the acid catalyst (Scheme 3.7). The majority of subsequent studies, however, have switched away from an IL with an added acid catalyst and towards Bronsted acid ionic liquids (BAILs) - a type of task-specific ionic liquid. BAILS incorporate an acidic moiety (typically either a sulfonic acid or a protonated nitrogen) on the cation allowing the BAILS to have dual functionality as both a solvent and a catalyst. There are several different classes of BAILs that have been applied to esterifications such as imidazo-lium 1, imidazolium sulfonic 2, phosphonium sulfonic 3, pyridinium sulfonic 4, quaternary ammonium 5, quaternary ammonium sulfonic 6 and lactam 7 based-BAILs (Scheme 3.8). 

Recently, Sirit and co-workers [45] developed calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids successfully used for alkylation of glycine-imine esters. In 2010, Itsuno et al. [46] published quartemary ammonium sulfonate polymers used for a-alkylation reaction of a glycine imine ester with high yields and enantioselectivity. 

Poole SK, Shetty PH, Poole CF (1989) Chromatographic and spectroscopic... tetraalkyl-ammonium sulfonates. Anal Chim Acta 218 241-264... 

Tabie 2.1 Improvement of hydrolysis stability due to ammonium sulfonate groups. 

A chiral quaternary ammonium sulfonate could be easily prepared from cinchonidine and a styrene sulfonate monomer was prepared from this... 

M, methanol A, acetonitrile T, tetrahydrofuran H, heptane ammonium sulfonic acid sodium salt P, NaH2P04 s, streaking. 

Class 4. Quaternary ammonium/sulfonic acids (or sulfate esters). Possessing both the permanent cationic charge of the quaternary ammonium group and... 

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