2-Hydroxynaphthalene-6 sulfonic

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). 

Synonyms Cl 15985 Food yellow 3 Food yellow 3 disodium salt 6-Hydroxy-5-[(4-sulfophenyl) azo]-2-naphthalenesulfonic acid, disodium salt 6-Hydroxy-5-((p-sulfophenyl) azo)-2-naphthalenesulfonic acid, disodium salt Orange yellow S 1-p-Sulfophenylazo-2-hydroxynaphthalene-6-sulfonate, disodium salt Sunset yellow Sunset yellow FCF... 

See 4,4 -Diaminodiphenyl sulfone 3,3 -Sulfonyldi-(benzenesulfonyl hydrazine). SeeDiphenyl-sulfon-3,3 -disulfohydrazide 4,4 -Sulfonyldiphenol. See 4,4 -Dihydroxydiphenyl sulfone Sulfooctadecanoic acid, sodium salt. See Sodium oleic sulfonate 18-Sulfooleic acid, compd. with 2,2, 2"-nitrilotriethanol (1 1). See TEA-oleyl sulfate 9-(Sulfooxy) octadecanoate acid, disodium salt. See Sodium oleic sulfate 1-p-Sulfophenylazo-2-hydroxynaphthalene-6-sulfonate, disodium salt. See FD C Yellow No. 6... 

The oxidation of alkanes by r-butyl hydroperoxide (TBHP) has been catalysed by titanium alkoxides, producing the corresponding alcohols and ketones. A radical mechanism is proposed in which r-butoxyl radical formed from TBHP and titanium alkoxide initiates the reaction. The evolution of oxygen (from the decomposition of peroxide) and the abstraction of hydrogen from alkane to form alkyl radical occur competitively. A method for the determination of both the primary and secondary KIEs at a reactive centre based on starting-material reactivities allows the determination of the separate KIEs in reactions for which neither product analysis nor absolute rate measurements are applicable. It has been applied to the FeCls-catalysed oxidation of ethylbenzene with TBHP, which exhibits both a primary KIE and a substantial secondary KIE the findings are in accordance with previous mechanistic studies of this reaction. The oxidation of two l-arylazo-2-hydroxynaphthalene-6-sulfonate dyes by peroxy-acids and TBHP catalysed by iron(III) 5,10,15,20-tetra(2,6-dichloro-2-sulfonatophenyl)porphyrin [Fe(ni)P] is a two-step process. In single turnover reactions, dye and Fe(in)P compete for the initially formed OFe(IV)P+ in a fast reaction and OFe(IV)P is produced the peroxy acid dye stoichiometry is 1 1. This is followed by a slow phase with 2 1 peroxy acid dye stoichiometry [equivalent to a... 

Other Names 2-Naphthalenesulfonic acid, 6-hydroxy-5-[(4-sulfophenyl)azo]-, disodium salt C.l. Food Yellow 3 C.L Food Yellow 3, disodium salt Sunset Yellow FCF l-p-Sulfophenylazo-2-hydroxynaphthalene-6-sulfonate disodium salt 1351 Yellow 1899 Yellow Acid Food Yellow 3 Acid Yellow TRA Aizen Food Yellow 5 Alabaster No. 3 Atul Sunset Yellow FCF C Orange 10 C.L 15985 Canacert Sunset Yellow FCF Certicol Sunset Yellow CFS Cilefa Orange S Cogilor Orange 213.11 D and C Yellow No. 6 Dolkwal Sunset Yellow E 110 E 110 (dye) Edicol Supra Yellow FC Eniacid Sunset Yellow Eurocert Orange FCE ED C Yellow 6 ED and C Yellow 6 FD and C Yellow No. 6 FD C Yellow No. 6 Food Yellow 3 Food Yellow 5 Food Yellow No. 5 HD Sunset Yellow FCF HD Sunset Yellow FCF Supra Hex-acol Sunset Yellow FCF Hexacol Sunset Yellow FCF Supra INS 110 Japan Food Yellow No. 5 Japan Yellow 5 Japan Yellow No. 5 KCA Foodcol Sunset Yellow FCF L... 

However, when using hydrophilic counter-ions (e.g. Hydroxynaphthalene, sulfonic acids) 30) a decrease in retention is observed, because the ion pair becomes more hydrophilic in respect to the uncomplexed amine. Furthermore increased counter-ion concentration as well as a pH change prevent the dissociation of the ion pair. 

Supplement to b) 2-Hydroxynaphthalene ((3-naphthol) is obtained from naphthalene. The reaction sequence includes sulfonation of the starting material at 150-160°C and subsequent alkaline baking of the intermediate sodium naphthalene-2-sulfonate with sodium hydroxide at 300 to 320°C for 6 to 8 hours. After the reac-... 

Lower-sulfonated subsidiary colors of sunset yellow, among them 5-(phenylazo)-6-hydroxy-naphthalene-2-sulfonic acid (ANSC) and 4-[(2-hydroxynaphthalene-l-yl)azo]benzenesulfonic acid (BNSC), were determined by reverse-phase HPLC using Novapak Cl 8 and gradient elution with a water-tetrahydrofuran solvent system buffered with ammonium acetate (192). 

A particularly important class of coupling components are the aminohydroxy-naphthalenesulfonic acids. Appropriate variation of the disazo component permits the development of shades ranging from orange to black. Orange and scarlet are achieved with I-acid (6-amino-l-hydroxy-naphthalene-3-sulfonic acid) and y-acid (7-amino-1-hydroxynaphthaIcne-3-sulfonic acid), whereas H-acid (8-amino-l-hydroxynaphthalene-3,6-disulfonic acid) and K-acid (8-amino-l-hydroxy-naphthalene-3,5-disulfonic acid) derivatives are useful for red to bluish-red hues. Extremely lightfast red shades are also accessible with disazo dyes ( brown dyes ). For chemical structures see Section 3.1.5). 

The most important coupling component for the Di—D and D 1- K<-D2 types is 6, which is produced by treatment of 6-amino-l-hydroxynaphthalene-3-sulfonic acid (I acid) with phosgene. 

Anilinesulfonic acids are chiefly used as starting component D, naphthylamine and Cleve acids as middle components Mi and M2, and I acid, its /V-phenyl derivatives, H acid, 2-amino-8-hydroxynaphthalene-6-sulfonic acid (y acid), and their derivatives as final component K. This type mainly possesses blue and green shades. Example C. I. DirectBlue 78, 34200 (16) [2503-73-3],... 

The synthesis of the 1 1 complex 8 is an example of [10] demethylative chroma-tion. It is prepared by diazotization of 5-amino-2-chlorohydroquinone dimethyl ether and coupling onto 1-hydroxynaphthalene-5-sulfonic acid. The reaction product and Cr203 in formic acid are heated in an autoclave at 130 °C. The chromium complex 8 [80004-31-5] is obtained as a black powder that gives grayish blue dyeings on wool and leather. 

In the stepwise synthesis of the unsymmetrical complex dye 13 [ 70236-60-1] [10], the azo dye made from diazotized l-amino-2-hydroxy-5-nitrobenzene and 1-phenyl-3-methyl-5-pyrazolone and the 1 1 chromium complex obtained from 6-nitro-l-diazo-2-hydroxynaphthalene-4-sulfonic acid and 2-naphthol are heated together at 80 °C for 5 h. The adduct is salted out with NaCl. A black powder is obtained that dyes wool and leather in dark brown shades. The resulting colors are fast, particularly on shrink-resistant wool. 

Alkaline glucose converts the diazonium salts of l-amino-2-hydroxy-naphthalene-4-sulfonic acid and its halogen, nitro, carboxyl, or sulfonic acid derivatives into the corresponding 2-hydroxynaphthalene-4-sul-fonic acids.126 According to this patent, the yields are nearly quantitative. 

The azo compounds are important chromophores because of extended electronic delocalisation between the two aromatic rings via the azo bond. The darkness of the dye is enhanced by extensive delocalisation combined with several sulfonic acid groups which function as auxochromes. An example is provided by Naphthol Blue Black B (10), prepared from 8-amino-l-hydroxynaphthalene-3,6-disulfonic acid (H-acid) (11) by coupling it in the 7-position with diazotised p-nitroaniline in acidic solution and subsequently coupling in the 2-position with diazotised aniline in alkaline solution (Scheme 3). The H-acid (11) is a very versatile component in dye manufacture because it can couple with diazonium salts in either the 2-position or 7-position depending on the pH of the reaction medium, as indicated in Scheme 3. 

Calmagite [l-(l-hydroxy-4-metbyl-2-phenylazo)-2-hydroxynaphthalene-4-sulfonic acid]... 

Naphthol. 6,8-disulfonic Acid. 7-Hydtox,y-1,3-naphthalenedisuljonic acid 2-hydroxynaphthalene-6,8-di-sulfonic acid G acid, Cl0H,O,S, mol wt 304,30. C 39.47%, H 2.65%, O 36.81%. S 21,0851), Prepd by heating 0 -naphthol with coned HjSCV 2 -naphthoi -3,6 -disulfonic acid (R acid) being obtained as a byproduct Fierz-David, Blangey ... 

Cassella s acid EINECS 202-153-0 F Acid 2-Hydroxynaphthalene-7-sulfonic acid 7-Hydroxy-2-naphthalenesulfonic acid 7-Hydroxynaphthalene-2-sulphonic acid Mono Acid F Mono F Acid Monosuifonic acid F p-Naphthol-7-sulfonic acid 2-Naphthalenesulfonic acid, 7-hydroxy- 2-Naphthol-7-sulfonic acid 2-Naphthol, 7-sulfo- NSC 1704. Used as an intermediate for azo dyes. Crystals mp 89° soluble in H2O, EtOH, insoluble in CsHe, Et20. 

Naphthalenediamine and its derivatives are obtained by heating 4-aminonaphthalene-2-sulfonic acid with ammonia or an amine at 160-180° under pressure any sulfo groups in the other ring are unaffected. 4-Hydroxynaphthalene-2-sulfonic acid exchanges both its sulfo and its hydroxyl group.1198... 

Isolation of the sulfonic acids as salts is usually carried out in one of two ways. In one the sulfonation mixture is taken up in water, neutralized with slaked lime, and filtered from the precipitated calcium sulfate, whereafter the filtrate, which contains the calcium salt of the sulfonic acid, is treated with sodium carbonate which converts the calcium into the sodium salt after filtration from calcium carbonate the solution is concentrated until crystallization occurs or, if necessary, evaporated to dryness. This procedure, termed chalking in industry, can be applied to all sulfonic acids except for the few cases such as l-amino-4-hydroxynaphthalene-2-sulfonic acid that give sparingly soluble calcium salts however, it is inconvenient because of the large volumes of liquid that must later be evaporated to avoid this precipitation of... 

A dye component that is used frequently is H acid (l-amino-8-hydroxynaphthalene-3,6-disulfonic acid). Production of this comparatively complex substitution pattern requires a series of different chemical reactions. The known side reactions and subsequent reactions on sulfonation and nitration of the naphthalene system and high-pressure hydrolysis of its substituents reduce the yield of the target product. If, as a consequence, intermediate isolations are unavoidable during the course of the process to prevent a gradual increase in the amount of by-products, additional product losses in mother and wash liquors will occur. Management of the often considerable quantities of solid waste and wastewater is therefore an important consideration in the production of H acid. 

Transferrin Is believed (17) to bind iron(III) with three phenolate (tyrosine) residues and, being weakly acidic, proton interference Is responsible for the significant difference between 3 (10 ) and K ff (10 ). The phenolate group Is also present In seven of the fourteen structures In Figure 1, which is testimony to the particularly strong and selective affinity of this group for iron(III). Proton interference increases with the number of phenolate groups and in the case of the trls complex of 2,3-di-hydroxynaphthalene-6-sulfonic acid, proton interference reduces 33 by a factor of 10 . 

Calmagite [l-(l-hydroxy-4-methyl-2-phenylazo)-2-hydroxynaphthalene-4-sulfonic acid] [3147-14-6] M 358.4, m 300", pKi 8.1, pK2 12.4. A erode dye is extracted with anhydrous diethyl ether and forms red crystals from M62CO. It gives a red colom in H2O at pH 7—9 and a blue colom at pH 9—11 which turns red on addition of Ca + or Mg + ions. [Lindstrom Diehl Chem 32 1123 I960]. Complexes with Ca, Mg and Th. 

CAS 1658-56-6 EINECS/ELINCS 216-760-3 Synonyms Cl 15620 Ext. D C Red. no. 8 Fast red A 4-(2-Hydroxynaphthalen-1-ylazo) naphthalene-1-sulfonic acid, sodium salt 4-((2-Hydroxy-1 -naphthalenyl) azo)-1 -naphthalene sulfonic acid sodium salt 1-Naphthalenesulfonic acid, 4-((2-hydroxy-1-naphthalenyl) azo)-, monosodium salt Red no. 506 Rocceline Roccelline Solid red A Classification Azobenzene Empiricai C2oHi4N2Na04S Properties M.w. 401.41 m.p. 280 C Toxicoiogy Mutagen TSCA listed Storage Store in cool, dry place keep container closed when not in use... 

Azo fuchsine. See Acid red 33 Cl 17200 Azogene fast orange GR. See o-Nitroaniline Azo grenadine. See Acid red 33 4,4 -Azo-3-hydroxynaphthalene-1-sulfonate. 

CAS 4548-53-2 EINECS/ELINCS 224-909-9 Synonyms 3-[(2,4-Dimethyl-5-sulfophenyl) azo]-4-hydroxy-1-naphthalenesulfonic acid disodium salt Disodium 3-[(2,4-dimethyl-5-sulfonatophenyl) azo]-4-hydroxynaphthalene-1-sulfonate Food red 1 Ponceau SX Classification Monoazo color Empirical Ci8Hi6N2Na207S2 Formula C18H16N2O7S2 2Na Properties M.w. 480.14 Toxicology TSCA listed... 

Diazon-8. See Polymethylene p-diazodiphenylamine sulfate 1 -Diazo-2-naphthol-4-sulfonic acid CAS 887-76-3 EINECS/ELINCS 212-958-9 Synonyms 4,4 -Azo-3-hydroxynaphthalene-1 -sulfonate 1-Naphthalenediazonium, 2-hydroxy-4-sulfo-, inner salt Empirical C10H6N2O4S Formula C10H5N2OSO3H Properties Yel. to brn. needles in paste or dry form si. sol in water m.w. 250.23 m.p. 160 C (dec.)... 

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