Naphthalene trisulfonic acid

A munber of organic compounds are suitable for use as tracers in a process for monitoring the flow of subterranean fluids. The following traces have been proposed benzene tetracarboxylic acid, methylbenzoic acid, naphthalenesulfonic acid, naphthalenedisulfonic acid, naphthalene-trisulfonic acid, alkyl benzene sulfonic acid, alkyl toluene sulfonic acid, alkyl xylene sulfonic acid, a-olefin sulfonic acid, salts of the foregoing acids, naphthalenediol, aniline, substituted aniline, pyridine, substituted pyridines [883]. 

In the first reaction stage, naphthalene is sulfonated with sulfuric acid. Subsequent nitration and neutralization of the naphthalene-trisulfonic acid with lime yields the calcium salt of l-nitronaphthalene-3,6,8-trisulfonic add, which is traditionally reduced to T-add (Koch-add) with iron filings and hydrochloric acid modem processes use continuous catalytic hydrogenation with a nickel catalyst. The H-acid is obtained by subsequent fusion of the T-acid with sodium hydroxide and neutralization with sulfuric acid. It serves as a coupling component in the production of azo dyes such as Direct Blue 15 or Acid Black 1. 

Both Watts and sulfamate baths are used for engineering appHcation. The principal difference in the deposits is in the much lower internal stress obtained, without additives, from the sulfamate solution. Tensile stress can be reduced through zero to a high compressive stress with the addition of proprietary sulfur-bearing organic chemicals which may also contain saccharin or the sodium salt of naphthalene-1,3,6-trisulfonic acid. These materials can be very effective in small amounts, and difficult to remove if overadded, eg, about 100 mg/L of saccharin reduced stress of a Watts bath from 240 MPa (34,800 psi) tensile to about 10 MPa (1450 psi) compressive. Internal stress value vary with many factors (22,71) and numbers should only be compared when derived under the same conditions. 

There is surprisingly little reliable information on the sulfonation of benzo[6]thiophene or its derivatives. Benzo[6]thiophene is more readily sulfonated than naphthalene.699 Reaction with concentrated sulfuric acid at 80° gives a mixture of mono-, di-, and trisulfonic acids, reaction with 70% sulfuric acid at 80° gives a monosulfonic acid,699 and reaction with 18% oleum gives a disulfonic acid 86 in each case the orientation of the products is unknown. Treatment of benzo[6]thiophene with concentrated sulfuric acid in acetic anhydride at 20° gives 3-acetylbenzo[6]thiophene (ca. 10%) and a sulfonation product (isolated as the potassium salt), which was believed to be the 3-sulfonic acid.660 Recently, the sulfonation product has been shown to contain the 2- (8%) and 3-isomer (92%), by conversion into the sulfonyl chlorides and reduction to a separable mixture of 2- and 3-mercaptobenzo[6]thiophene.84... 

AR08 CioHa0gS3 naphthalene-1,3,6-trisulfonic acid L66J bswq dswq hswq HgO PY KCI 0.1 20 DME/SCE OA- C=lr... 

At low temperatures naphthalene-1-sulfonic acid predominates whereas at higher temperatures (up to 160°C) the 2-product is formed in higher yields (85 percent). Further sulfonation at 150 to 160°C gives rise to di-, tri-, and tetra-sulfonic acids. The important naphthalene-1, 3,6-trisulfonic acid can be obtained directly from naphthalene by progressive sulfonation with fuming sulfuric acid first at 40°C, then at 60°C, and finally at 150 to 155°C [11]. 

The intermediate derived from naphthalene-1,3,6-trisulfonic acid along with the class of derived dyes are shown in Table 8.3 [11]. 

Derivation Naphthalcnc-(i-sutonic acid is sulfonat-ed with 60% oleum at 165C, the resulting naphthalene-1,3,6-trisulfonic acid is nitrated and the product reduced with iron. 

F Antrypol BAY 205 Bayer 205 1-(3-Benzamido-4-methylbenzamido)naphthalene-4,6.8-trisulfonic acid EINECS 204-949-3 Fourneau 309 Germanin Moranyl Naganin Naganine Naganinum Naganol Naphuride sodium 1,3,5-... 

The FD mass spectra of the di-n-butylammonium salts of a few naphthalene- and anthraquinonesulfonic acids have been reported38. The spectra were dominated by the [Bu2NH2] + ion ([Cat]+). Naphthalene-1-sulfonic acid dibutylammonium salt showed a major [M + Cat] + ion while more abundant ions were [M + H] + in the spectrum of naphthalene-2,6-disulfonic acid di-dibutylammonium salt and [M — Cat + 2H] + in the spectrum of naphthalene-1,3,6-trisulfonic acid tri-dibutylammonium salt. 

Acid blue 92 [4-((4-anilino-5-sulfo-l-naphthyl)azo-5-hydroxy-2,7-naphthalene-disulfonic acid trisodium salt, trisodium 4 -anilino-8-hydroxy-1,1 -azonaphthalene-3,6,5-trisulfonate, benzyl blue R, Cl 13390] [3861-73-2]... 

Naphthalene-2-thiol P-Naphthalenethiol. See 2-Naphthalenethiol Naphthalene-1,3,6-trisulfonic acid... 

In the polysubstitution of naphthalene the sulfo groups are never found ortho, para, or peri (1,8) to one another even so, six disulfonic acids, three trisulfonic acids, and one tetrasulfonic acid are obtainable by sulfonation reactions. Seventy-three polysulfonic acids are theoretically possible. The acids obtainable from naphthalene by sulfonation are indicated in the chart the symbol S used in the formulas represents the sulfonic acid group. 

Direct high-temperature (180 ) sulfonation of naphthalene with 24% oleum gives the 1,3,6-trisulfonic acid the 1,3,5-trisulfonic acid is made by treating the 1,5-diacid with 67% oleum at 90 the 1,3,7-triacid is obtained by further sulfonation of the 2,6-diacid by oleum at 100 . Both the 1,3,5- and 1,3,7-ttisulfonic acids yield the 1,3,5,7-tetrasulfonic acid on treatment with oleum. A fourth sulfonic acid group is not introduced into the 1,3,6-trisulfonic acid, even by treatment with sulfur trioxide. 

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