Sulfate amides

Glucuronidation Esterification with sulfate Amidation with Gly and Glu... 

Anionics Carboxylates Sulfates Acyi sarcosinates Sulfated amides Acyiated peptides Aikyl suifates Aikyl ether suifates Suifated aicohois Suifated esters Sulfonates Aikyibenzene suifonates Diaikyisuifosuccinates Oiefin and aikane suifonates Suifonates amides Suifonated esters Suifonates fatty esters Metai aikyiphosphates Soaps... 

Organic azides can be obtained from cyclic sulfates and from cyclic sulfiles (Schane 3.4). Avenoza et al. studied the nucleophilic ring-opening reactions of gm-disubstituted cyclic sulfates with sodium azide, which lead to the synthesis of azido alcohols 37 and 38. They observed that the legioselectivity depends on the substiment present on the cyclic sulfate. Amide substituents lead preferentially to products arising from nucleophilic attack at the least substituted Cp position, whereas reverse regioselectivity is obtained... 

Chem. Descrip. Sulfated amide Ionic Nature Anionic... 

To a vigorously stirred suspension of 2 mol of lithium amide in 2 1 of liquid atimonia (see II, Exp. 11) was added in 15 min 1 mol of propargyl alcohol (commercial product, distilled in a partial vacuum before use). Subsequently, 1 mol of butyl bromide was added dropwise in 75 min. After an additional 1.5 h, stirring was stopped and the ammonia was allovied to evaporate. To the solid residue were added 500 ml of ice-water. After the solid mass had dissolved, six extractions with diethyl ether were performed. The (unwashed) combined extracts were dried over magnesium sulfate and then concentrated in a water-pump vacuum. Distillation of the residue through a 40-cm Vigreux column afforded 2-heptyn-l-ol, b.p. 

Terminal alkynes are only reduced in the presence of proton donors, e.g. ammonium sulfate, because the acetylide anion does not take up further electrons. If, however, an internal C—C triple bond is to be hydrogenated without any reduction of terminal, it is advisable to add sodium amide to the alkyne solution Hrst. On catalytic hydrogenation the less hindered triple bonds are reduced first (N.A. Dobson, 1955, 1961). 

AMIDES, FATTY ACID] (Vol 2) n-Tetradecyl hydrogen sulfate [4754-44-3]... 

Nitdles may be prepared by several methods (1). The first nitrile to be prepared was propionitdle, which was obtained in 1834 by distilling barium ethyl sulfate with potassium cyanide. This is a general preparation of nitriles from sulfonate salts and is referred to as the Pelou2e reaction (2). Although not commonly practiced today, dehydration of amides has been widely used to produce nitriles and was the first commercial synthesis of a nitrile. The reaction of alkyl hahdes with sodium cyanide to produce nitriles (eq. 1) also is a general reaction with wide appHcabiUty ... 

The amide group is readily hydrolyzed to acrylic acid, and this reaction is kinetically faster in base than in acid solutions (5,32,33). However, hydrolysis of N-alkyl derivatives proceeds at slower rates. The presence of an electron-with-drawing group on nitrogen not only facilitates hydrolysis but also affects the polymerization behavior of these derivatives (34,35). With concentrated sulfuric acid, acrylamide forms acrylamide sulfate salt, the intermediate of the former sulfuric acid process for producing acrylamide commercially. Further reaction of the salt with alcohols produces acrylate esters (5). In strongly alkaline anhydrous solutions a potassium salt can be formed by reaction with potassium / /-butoxide in tert-huty alcohol at room temperature (36). 

The hydroxyl groups on glycols undergo the usual alcohol chemistry giving a wide variety of possible derivatives. Hydroxyls can be converted to aldehydes, alkyl hahdes, amides, amines, a2ides, carboxyUc acids, ethers, mercaptans, nitrate esters, nitriles, nitrite esters, organic esters, peroxides, phosphate esters, and sulfate esters (6,7). 

Naphthalenediol. This diol is prepared by the alkah fusion of 2-hydroxynaphthalene-6-sulfonic acid (Schaffer acid) at 290—295°C. Schaffer acid is usually produced by sulfonation of 2-naphthol with the addition of sodium sulfate at 85—105°C. This acid is also used as a coupling component in the production of a2o dyes such as Acid Black 26. 2,6-Naphthalenediol is used as a component in the manufacture of aromatic polyesters which, as is also tme of the corresponding amides, display Hquid crystal characteristics (52). 

Although soaps have many physical properties in common with the broader class of surfactants, they also have several distinguishing factors. First, soaps are most often derived direcdy from natural sources of fats and oils (see Fats and fatty oils). Fats and oils are triglycerides, ie, molecules comprised of a glycerol backbone and three ester-linked fatty oils. Other synthetic surfactants may use fats and oils or petrochemicals as initial building blocks, but generally require additional chemical manipulations such as sulfonation, esterification, sulfation, and amidation. 

Sulfation by sulfamic acid has been used ia the preparation of detergents from dodecyl, oleyl, and other higher alcohols. It is also used ia sulfating phenols and phenol—ethylene oxide condensation products. Secondary alcohols react ia the presence of an amide catalyst, eg, acetamide or urea (24). Pyridine has also been used. Tertiary alcohols do not react. Reactions with phenols yield phenyl ammonium sulfates. These reactions iaclude those of naphthols, cresol, anisole, anethole, pyrocatechol, and hydroquinone. Ammonium aryl sulfates are formed as iatermediates and sulfonates are formed by subsequent rearrangement (25,26). 

Amide-Based Sulfonic Acids. The most important amide-based sulfonic acids are the alkenylarnidoalkanesulfoiiic acids. These materials have been extensively described ia the Hterature. A variety of examples are given ia Table 5. Acrylarnidoalkanesulfoiiic acids are typically prepared usiag technology originally disclosed by Lubrizol Corporation ia 1970 (80). The chemistry iavolves an initial reaction of an olefin, which contains at least one aHyhc proton, with an acyl hydrogen sulfate source, to produce a sulfonated intermediate. This intermediate subsequendy reacts with water, acrylonitrile, and sulfuric acid. 

Other Applications. Hydroxylamine-O-sulfonic acid [2950-43-8] h.2is many applications in the area of organic synthesis. The use of this material for organic transformations has been thoroughly reviewed (125,126). The preparation of the acid involves the reaction of hydroxjlamine [5470-11-1] with oleum in the presence of ammonium sulfate [7783-20-2] (127). The acid has found appHcation in the preparation of hydra2ines from amines, aUphatic amines from activated methylene compounds, aromatic amines from activated aromatic compounds, amides from esters, and oximes. It is also an important reagent in reductive deamination and specialty nitrile production. 

Because phenoHc compounds are easily sulfonated, their sulfation must be accompHshed with mil der sulfating agents, eg, complexes of sulfur thoxide or chlorosulfonic acid with trimethyl amine, dimethylform amide, pyhdine, or dim ethyl a n i1 in e, in anhydrous or aqueous medium below 100°C (86-89). 

Sulfated Acids, Amides, and Esters. Reaction with sulfuric acid may be carried out on fatty acids, alkanolamides, and short-chain esters of fatty acids. The disodium salt of sulfated oleic acid is a textile additive and an effective lime soap dispersant. A typical sulfated alkanolamide stmcture is CiiH23C0NHCH2CH20S03Na. Others include the sulfates of mono and diethanolamides of fatty acids in the detergent range. The presence of... 

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