Naphthalene sulfonate

POPOP p-bis[2-(5-phenyloxazoyl)]benzene. t ANS, anilino-8-naphthalene sulfonic acid. t TNS, 2-p-toluidinylnaphthalene-6-sulfonate. 

Amino-3-hydroxy-7-nitro-l-naphthalene-sulfonic acid [6259-63-8]... 

Naphthalenesulfonic acids are important chemical precursors for dye intermediates, wetting agents and dispersants, naphthols, and air-entrainment agents for concrete. The production of many intermediates used for making a2o, a2oic, and triphenylmethane dyes (qv) involves naphthalene sulfonation and one or more unit operations, eg, caustic fusion, nitration, reduction, or amination. 

Generally, the sulfonation of naphthalene leads to a mixture of products. Naphthalene sulfonation at less than ca 100°C is kineticaHy controlled and produces predominandy 1-naphthalenesulfonic acid (4). Sulfonation of naphthalene at above ca 150°C provides thermodynamic control of the reaction and 2-naphthalenesulfonic acid as the main product. Reaction conditions for the sulfonation of naphthalene to yield desired products are given in Figure 1 alternative paths are possible. A Hst of naphthalenesulfonic acids and some of their properties is given in Table 1. 

A naphthalene sulfonation product that is rich in the 2,6-isomer and low in sulfuric acid is formed by the reaction of naphthalene with excess sulfuric acid at 125°C and by passing the resultant solution through a continuous wiped-film evaporator at 245°C at 400 Pa (3 mm Hg) (26). The separation in high yield of 99% pure 2,6-naphthalenedisulfonate, as its anilinium salt from a cmde sulfonation product, has been claimed (27). A process has been patented for the separation of 2,6-naphthalenedisulfonic acid from its isomers by treatment with phenylenediarnine (28). 

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... 

In 1994 estimated naphthalene consumption in western Europe and Japan for the production of alkylnaphthalene sulfonates, naphthalene sulfonate formaldehyde condensates, and synthetic tanning agents was... 

NaOH solution is added dropwise to an aqueous suspension of this ester at 40—70°C over 1 h and the reaction mixture kept for 2 h to give 86.6% DHNA of 98.7% purity (74), which is then esterified with (CgH O) to obtain PDNA. The esterification process is dramatically improved by adding a small amount of inorganic or organic acid, preferably methanesulfonic acid, benzene sulfonic acid, or naphthalene sulfonic acid subsequent isolation and crystallisation gives a pure product (75). 

The most widely used pitch control method is the addition of pitch dispersants, which can be either organic, ie, typically anionic polymers such as naphthalene sulfonates, ligninsulfonates, and polyacrylates (33,34), or inorganic, ie, typically clay or talc. The polymers maintain the pitch as a fine dispersion in the pulp, preventing agglomeration and potential deposition on the paper machine or the sheet. When talc, clay, or other adsorbent fillers are added to the furnish, moderate amounts of pitch can adsorb on these materials, producing a nontacky soHd that can be retained in the sheet. 

Dispersants (qv) have been added to the pulper to maintain stickies in a colloidal state. The small particle size reduces the problems stickies cause on the paper machine and in paper products. Among the chemicals that have been used are fatty alcohol ethoxylates, alkylphenol ethoxylates, lignosulfonates, and naphthalene sulfonates (18). 

Includes naphthalene sulfonates and naphthalene sulfonate formaldehyde condensates. 

There are three main uses for naphthalene sulfonic acid derivatives (75—79) as naphthalenic tanning material alkyl naphthalene sulfonates for industrial appHcations as nondetergent wetting agents and as dye intermediates. Consumption of naphthalene sulfonates as surfactants accounts for a large portion of usage. Naphthalene sulfonate—formaldehyde condensates are also used as concrete additives to enhance flow properties. Demand for naphthalene sulfonates in surfactants and dispersent appHcations, particularly in concrete, was expected to increase into the twenty-first century. Consumption as of 1995 was 16 x 10 kg/yr. 

The material, made by a two-step diazotization of each naphthalenic sulfonic acid derivative, is typically used in the form of the neutralized sodium salt. A similar sulfonic acid-based azo dye (4) which falls into the class of reactive dyes is also shown (76). This compound, made similarly to (3), is used as a blue dyestuff for cotton and wool. 

In more recent times, naphthalene has been used in condensation products from naphthalene sulfonic acids, utili2ing formaldehyde as additives to improve the flow properties of concrete these are referred to as superplastici2ers. Another newer appHcation is the production of diisopropylnaphthalenes. The mutual depression of the melting points in the mixture gives a Hquid which is used as a solvent for dyes in the production of carbonless copy paper. 

As in the nitration of naphthalene, sulfonation gives the 1-substituted naphthalene. However, because the reverse reaction (desulfonation) is appreciably fast at higher temperatures, the thermodynamically controlled product, naphthalene-2-sulfonic acid, can also be obtained. Thus it is possible to obtain either of the two possible isomers of naphthalene sulfonic acid. Under kineticaHy controlled conditions naphthalene-l-sulfonic acid [85-47-2] (82) is obtained thermodynamic control gives naphthalene-2-sulfonic acid [120-18-3] (83). 

Naphthoic acid has been prepared principally by the hydrolj sis of d-naphthonitriled the overall yields from (3-naph-thylamine, from sodinm-/3-naphthalene sulfonate, and from calcium d-naphthalene sulfonate being given as (approximately) 20 per cent, 21 per cent, and 50 per cent, respectively. The acid has been prepared also by the carbonation of the Grignard reagent from the less accessible /3-bromo derivative and. more recendy, from the readily available methyl ketone. ... 

To this mixture there is then added slowly over a period of 30 minutes 10 grams of - -)-a-aminobenzylpenicillin beta-naphthalene sulfonate. The mixture is agitated for 3 hours at 25°-30°C. The product, D- -)-o -aminobenzylpenicillin trihydrate precipitates and is collected by filtration. The filter cake of the product is washed several times with methyl isobutyl ketone and is dried at 40°C. The product is obtained in about a 90% yield and has a potency of 865 mcg/mg. It is determined by Karl Fischer analysis to have a moisture content of 13.4% by weight. 

Ampicillin beta naphthalene sulfonate Ampicillin trihydrate 3,17-Androstandione Stanolone... 

White monoclinic leaflets, mp 123—24°, bp 295°, d 1.28g/cc at 20°. Sol in ale, eth, chlf, glye, oils alkaline solns. Prepn from 2-naphthalene sulfonate by fusing with caustic soda, decomposing the melt with hydrochloric acid distilling off the 2-naphthol in vacuo. Flash point is 307°F, Qc 8213cal/g, Qf 34.2kcal/mole Refs 1) Beil 6,627, (310) [591] 2)A. 

Participation by cumulative double bonds and vinyl cation intermediates has been suggested in the solvolyses of a number of homoallenyl systems. Hanack and Haffner (87) reported the solvolyses of 3,4-pentadienyl jS-naphthalene sulfonate, 110 (R = H) under a variety of conditions. The products... 

Toluidino-2-naphthalene sulfonic acid (TNS reagent) cholesterol [180] phospho- and glycolipids [181] neutral lipids [182]... 

Abbreviations EPR, electron paramagnetic resonance FITC, fluorescein-5 -isothiocyanate lAEDANS, iV-iodoacetyl-N -(5-sulfo-l-naphthyl)ethylenediamine NCD, fluorescent yV-cyclohexyl-N -(4-dimethyl-amino-a-naphthyl)carbodiimide RITC, rhodamine-5 -isothiocyanate DPPE, dipalmitoylphosphatidyl-ethanolamine PE, egg phosphatidyl-ethanolamine ANS, 8-anilino-l-naphthalene sulfonate DPH, diphenylhexatriene e-ADP, l,iV -ethanoadenosine-5 -diphosphate TNP-ADP, 2 [3 ]-0-(2,4,6-trinitrophe-nyl)adenosine-5 -diphosphate. 

C subfamily of type 1 extradiol dioxygenases (Mars et al. 1999). The alternative extradiol fission of 3-chlorocatechol may take place between the 1 and 6 positions (distal fission), and this has been shown for the 2,3-dihydroxybiphenyl 1,2-dioxygenase from the naphthalene sulfonate degrading Sphingomonas sp. strain BN6 (Riegert et al. 1998). 

A water-soluble polymer of monoallylamine can be used in conjunction with a sulfonated polymer, such as a water-soluble lignosulfonate, condensed naphthalene sulfonate, or sulfonated vinyl aromatic polymer, to minimize fluid loss from the slurry during well cementing operations [1510,1511]. The polymer... 

The fluid loss and thickening time characteristics of the cement slurry is altered, either by increasing the molecular weight of the lignin by cross-linking with formaldehyde or epichlorohydrin or by adding agents such as sodium sulfite, sodium metasilicate, sodium phosphate, and sodium naphthalene sulfonate. 

Another method is amination with a polyamine and an aldehyde [1567]. The formulation also contains sodium carbonate, sodium phosphate, sodium sulfite, sodium metasilicate, or naphthalene sulfonate. The sulfonated or sulfomethyl-ated aminated lignin shows less retardation (shorter thickening time) than a sulfonated or sulfomethylated lignin without the attached amine. 

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