Sodium 3-naphthalenesulfonate

Naphthalenol. 2-Naphthol or p-naphthol or 2-hydroxynaphthalene/7i3 -/5 -i7 melts at 122°C and boils at 295°C, and forms colorless crystals of characteristic, phenoHc odor which darken on exposure to air or light. 2-Naphthol [135-19-3] is manufactured by fusion of sodium 2-naphthalenesulfonate with sodium hydroxide at ca 325°C, acidification of the drowned fusion mass which is quenched ia water, isolation and water-washing of the 2-naphthalenol, and vacuum distillation and flaking of the product. A continuous process of this type has been patented (69). The high sulfate content ia the primary effluent from 2-naphthol production is greatiy reduced ia modem production plants by the recovery of sodium sulfate. 

Sodium 2-naphthalenesulfonate [532-02-5] M 230.2. Crystd from hot 10% aqueous NaOH or water, and dried in a steam oven. 

S Hamai, H Sakurai. 2H20 effects on the inclusional complexation of cyclodextrin with sodium 2-naphthalenesulfonate in capillary electrophoresis and UV spectrometry. J Chromatogr A 800 327-332, 1998. 

Sodium 2-naphthalenesulfonate reacts with piperidine in the presence of sodium amide to give N-(2-naphthyl)piperidine in 71% isolated yield4 (equation 3). By the... 

FIGURE 9.3 Structures of benzene, naphthalene, and anthracene derivatives analyzed sodium benzenesulfonate (1), 4-chloroaniline (2), 3,4-dichloroaniline (3), 2-naphthylamine (4), sodium 2-naphthalenesulfonate (5), sodium anthraquinone 2-sulfonate monohydrate (6), 1,2-diamineanthraquinone (7), 2-anthraceencarboxilic acid (8), and 2-anthramine (9). 

Li, Y. An improved process for preparing sodium 2-naphthalenesulfonate and production of 2-naphthol. Faming Zhuanli Shenqing Gongkai Shuomingshu CN 1557807, 2004 Chem. Abstr. 2005, 143, 231758. 

The onset of the triplet-state phosphorescence emission of several p-hydroxyphenacyl esters indicated triplet energies of 68.9 to 70.6 kcal/mol. The phosphorescence emissions were quenched by sodium 2-naphthalenesulfonate or potassium sorbate. Quenching studies confirmed the reactivity of the triplet state and further provided a lifetime of 5.5 ns for the triplet with a release rate of 1.82 X 10 s in later studies (vide infra). 

Sodium / -naphthalenesulfonate was chosen as the surface-active electrolyte because its structure is simple and rigid. It does not form micelles, so there is no question as to the species adsorbed on the surface. It is a strong electrolyte and is expected to be essentially completely ionized at saturation coverage. SNS stabilized dispersions flocculate over periods of minutes to months depending on the concentration of SNS. Sterling FTG has a non-polar, non-ionic, hydrophobic surface. The ultimate particles have large, flat, polyhedral surfaces. The particle size distribution of the dry carbon is narrower than that of most colloidal carbons (2). 

Alkali fusion of sodium naphthalenesulfonate is one of the most important organic-technical operations. With the low price of naphthol, it is not surprising that only a few manufacturers undertake the preparation. Very cheap materials, such as coal, soda, and sulfuric acid, are essential. 

The yield of sodium naphthalenesulfonate is 165 per cent, or 429 kilograms, costing 47.66 frs. Hence, 100 kilograms costs 11.10 frs. 

Naphthalenesulfonyl chloride, m.p. 76°, is prepared in similar manner and 73% yield from 2 kg. of sodium / -naphthalenesulfonate. 

Brown, W., Johansson, K., Ahngren, M. Threadlike micelles fiorn cetyltrimethylammonium bromide in aqueous sodium naphthalenesulfonate solutions studied by static and dynamic hght scattering. J. Phys. Chem. 1989, 93(15), 5888-5894. 

Naphthalenesulfonic Acid. The sulfonation of naphthalene with excess 96 wt % sulfuric acid at < 80°C gives > 85 wt % 1-naphthalenesulfonic acid (a-acid) the balance is mainly the 2-isomer (P-acid). An older German commercial process is based on the reaction of naphthalene with 96 wt % sulfuric acid at 20—50°C (13). The product can be used unpurifted to make dyestuff intermediates by nitration or can be sulfonated further. The sodium salt of 1-naphthalenesulfonic acid is required, for example, for the conversion of 1-naphthalenol (1-naphthol) by caustic fusion. In this case, the excess sulfuric acid first is separated by the addition of lime and is filtered to remove the insoluble calcium sulfate the filtrate is treated with sodium carbonate to precipitate calcium carbonate and leave the sodium l-naphthalenesulfonate/7J(9-/4-J7 in solution. The dry salt then is recovered, typically, by spray-drying the solution. 

In the manufacture of 2-naphthalenol, 2-naphthalenesulfonic acid must be converted to its sodium salt this can be done by adding sodium chloride to the acid, and by neutralizing with aqueous sodium hydroxide or neutralizing with the sodium sulfite by-product obtained in the caustic fusion of the sulfonate. The cmde sulfonation product, without isolation or purification of 2-naphthalenesulfonic acid, is used to make 1,6-, 2,6-, and 2,7-naphthalenedisulfonic acids and 1,3,6-naphthalenetrisulfonic acid by further sulfonation. By nitration, 5- and 8-nitro-2-naphthalenesulfonic acids, [89-69-1] and [117-41-9] respectively, are obtained, which are intermediates for Cleve s acid. All are dye intermediates. The cmde sulfonation product can be condensed with formaldehyde or alcohols or olefins to make valuable wetting, dispersing, and tanning agents. 

All lnaphthalenesulfonic Acids. The aLkyLnaphthalenesulfonic acids can be made by sulfonation of aLkyLnaphthalenes, eg, with sulfuric acid at 160°C, or by alkylation of naphthalenesulfonic acids with alcohols or olefins. These products, as the acids or their sodium salts, are commercially important as textile auxiUaries, surfactants (qv), wetting agents, dispersants (qv), and emulsifying aids, eg, for dyes (qv), wettable powder pesticides, tars, clays (qv), and hydrotropes. 

Naphthalenesulfonic Acid—Formaldehyde Condensates. The sodium salts of the condensation products of naphthalenesulfonic acid with formaldehyde constitute an important class of compounds which are mainly used in the area of concrete additives (32,33), agricultural formulations, mbber formulations, and synthetic tanning agents. They are also used in photographic materials (34). Hampshire Chemical Co. and Henkel of America, Inc., are the largest suppHers of naphthalene sulfonate in concrete additives (superplasticizer) and reportedly hold 75—80% of this market. It was estimated that naphthalene sulfonate demand from U.S. producers would reach approximately... 

Acid-cataly2ed hydroxylation of naphthalene with 90% hydrogen peroxide gives either 1-naphthol or 2-naphthiol at a 98% yield, depending on the acidity of the system and the solvent used. In anhydrous hydrogen fluoride or 70% HF—30% pyridine solution at — 10 to + 20°C, 1-naphthol is the product formed in > 98% selectivity. In contrast, 2-naphthol is obtained in hydroxylation in super acid (HF—BF, HF—SbF, HF—TaF, FSO H—SbF ) solution at — 60 to — 78°C in > 98% selectivity (57). Of the three commercial methods of manufacture, the pressure hydrolysis of 1-naphthaleneamine with aqueous sulfuric acid at 180°C has been abandoned, at least in the United States. The caustic fusion of sodium 1-naphthalenesulfonate with 50 wt % aqueous sodium hydroxide at ca 290°C followed by the neutralization gives 1-naphthalenol in a ca 90% yield. 

Naphthalenediol. This compound darkens rapidly in air. It can be made by fusion of the sultone of 8-hydroxy-1-naphthaIenesulfonic acid with 50 wt % sodium hydroxide at 200—230°C, or by the hydrolytic desulfonation of l,8-dihydroxy-4-naphthalenesulfonic acid. The diol also reacts with ammonia to give 1,8-naphthalenediamine. 

By the nitrosation of 2-naphthalenol and the reaction of the nitroso compound with sodium bisulfite. By nitrosation/reduction of 6-hydroxy-2-naphthalenesulfonic acid. 

Sodium Bisulfite. Sodium bisulfite [7631-90-5] NaHSO, is occasionally used to perform simultaneous reduction of a nitro group to an amine and the addition of a sulfonic acid group. For example, 4-amino-3-hydroxyl-l-naphthalenesulfonic acid [116-63-2] C qH NO S, is manufactured from 2-naphthol in a process which uses sodium bisulfite (59). The process involves nitrosation of 2-naphthol in aqueous medium, followed by addition of sodium bisulfite and acidification with sulfuric acid. 

The most commonly used emulsifiers are sodium, potassium, or ammonium salts of oleic acid, stearic acid, or rosin acids, or disproportionate rosin acids, either singly or in mixture. An aLkylsulfate or aLkylarenesulfonate can also be used or be present as a stabilizer. A useful stabilizer of this class is the condensation product of formaldehyde with the sodium salt of P-naphthalenesulfonic acid. AH these primary emulsifiers and stabilizers are anionic and on adsorption they confer a negative charge to the polymer particles. Latices stabilized with cationic or nonionic surfactants have been developed for special apphcations. Despite the high concentration of emulsifiers in most synthetic latices, only a small proportion is present in the aqueous phase nearly all of it is adsorbed on the polymer particles. 

Sodium 1-naphthalenesulfonate [130-14-3] M 230.2. Recrystd from water or aqueous acetone [Okadata et al. 7 Am Chem Soc 108 2863 1986]. 

Sodium /3-naphthalenesulfonate, technical grade, from Matheson, Coleman and Bell was dried in an oven and then used directly. 

Sodium a-naphthalenesulfonate, reaction with piperidine to form N-a-naphthyipiperidine, 40, 75 Sodium 0-naphthalenesulfonate, reaction with piperidine to form N-/3-naphthylpiperidine, 40, 74 Sodium nitrite in conversion of diethyl malonate to diethyl isonitroso-malonate, 40, 21... 

CN 1,2,3,4-tetrahydro-2-methyl-1,4-dioxo-2-naphthalenesulfonic acid sodium salt... 

Abbreviations. aT = a-tocopherol, AC = aminocoumarin, ANS = l-anilino-8-naphthalenesulfonic acid, CTAB = cetyltrimethylammonium bromide, DPPC = dipalmitoylphosphatidylcholine, DPPH — l,l-diphenyl-2-picrylhydrazyl, DSHA = Ai-dansylhexadecylamine, GMO = glycerol monooleate, HC = hydrocoumarin, N,N -DOC = JV,JV -di(octadecyl)oxacarbocyanine, PC = phosphatidylcholine, p-CUO = pyrene caroboxaldehyde, SDES — sodium decyl sulfate, SDS — sodium dodecyl sulfate, STS = sodium tetradecyl sulfate. 

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