Sulfo acids

A purified fatty acid is recommended for the preparation of a pure a-sulfo acid. Purified palmitic acid (m.p. 60.8-61.4°, neutralization equivalent 256.2) is prepared by twice recrystallizing a good commercial grade of palmitic acid from acetone at 0°, using a solvent ratio of 10 ml. to 1 g. However, the reaction may be applied to commercial saturated higher fatty acids, if the iodine number is sufficiently low. The checkers obtained similar results with recrystaUized Neo-Fat 1-56 (Armour and Company, Chicago, 111.) or Eastman white label palmitic acid. 

A)J.P.Gray,USP 1438759(1922) St CA 17,882 (1923)(Rosin 2-12% is added to BkPdr as retarder) B)Lignosa S.Akcyjna.FrP 641442 (1927) CA 23,1272(1929)(Charcoal in BkPdr is replaced by hydrocarbons such as C10Hg sulfo acids of C10Hg or phenols, nitrosulfo acids of phenols, nitrosulfo acids of phenols. Carbohydrates, such as cellulose, starch or sawdust also may be used) C)Dynamit A—G, PhrNaoum... 

Thiosulfuric acid is representative of a general class of acids, called thio acids or sulfo acids, in vhich one or more oxygen atoms of an oxygen add are replaced by sulfur atoms. For example, arsenic penta-sulfide dissolves in a sodium sulfide solution to form the thioarsenate ion, AsS -----, completely analogous to the arsenate ion, AsO ------- ... 

But other sulfo acids, such as sulfarsenic acid, H AsS, are stable, and are of use in analytical chemistry and in chemical industry,... 

Effect of Sulfuric Acid on Organic Compounds. The continuing controversy regarding the constitution and formation of the so-called sulfo acids, etc., makes it appropriate to discuss in somewhat more detail those reactions of sulfuric acid on organic compounds in which so-called copulated compounds are formed. 

It should be noted that the key passage of my earlier article referred, as can be easily seen from the context, not so much to views concerning sulfo acids, as to the views often expressed in recent times about amide acids of monobasic acids and some other amide-like substances. 

Sulfur trioxide and its hydrates are generally unsuitable for sulfonating saturated aliphatic compounds. Either no reaction occurs, or oxidative decomposition takes place, yielding a complex mixture. Long-chain saturated fatty acids can, however, be smoothly sulfonated with SO3 (liquid or vapor) to give good yields of a-sulfo acids as follows ... 

Sulfuric acid, or sulfur trioxid, converts the nitrils into sulfo-acids and inonoammonio sulfate ... 

As a new approach to sulfonated poljnners, sulfonation of oligo(2-propenyloxy)methyloxyirane by SO2 in presence of amines has been studied (163). It was shown that, depending on the reaction conditions, oligomeric sulfo acid or its derivatives (58) as well as crown polysulfonic acid (59) can be synthesized. Crown polysulfonic acid is produced by the copolymerization of SO2 with double bonds of unsaturated oligomer. 

Ammonium nitrate granules and fertilizers based on these are coated with a layer consisting of sodium phosphates (trimetaphosphate and polyphosphate) and salts of alkylaryl sulfo-acids. These reagents may be added either both together to the ammonium nitrate melt or separately the sodium phosphates to the melt and the sodium salts of the alkylaryl sulfo-acids to the granules. The granules with added polyphosphates are then powdered with diatomite [538]. 

Of minor importance are the sulfobetains (the anionic group is a sulfo acid instead of a carboxylic acid). More important are imidazolinium betains, which are made by reaction of imidazolines (- imidazoline derivatives) with chloroacetic acid. The ring is hydrolized during the process and leaves a mixture of N-substituted fatty acid amides with -CH2-CH2-OH and -CH2COONa in varying number and arrangement. 

This reaction is effected by heating a suspension of beta-naphthol in water vitli equivalent quantities of formaldehyde and sodium bisulfite. The sulfo acid is reported to ciystallize from solution on cooling after acidifica tion with acetic acid. The formation of this sulfonate of a naphthol analogue of saligenin is of particular interest, since monomethylolnaphthols haw never been isolated. 

Esterification is not the only method of derivatizing the carboxyl functionality, and it is not surprising that amides and A -aUtylamides of the ot-sulfo acids have also received extensive attention in the surfactant patent literature. The ot-sulfoalkanolamides have the general structure... 

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