Mon compte

connexion

inscription

   Publicité R▼


 » 
allemand anglais arabe bulgare chinois coréen croate danois espagnol espéranto estonien finnois français grec hébreu hindi hongrois islandais indonésien italien japonais letton lituanien malgache néerlandais norvégien persan polonais portugais roumain russe serbe slovaque slovène suédois tchèque thai turc vietnamien
allemand anglais arabe bulgare chinois coréen croate danois espagnol espéranto estonien finnois français grec hébreu hindi hongrois islandais indonésien italien japonais letton lituanien malgache néerlandais norvégien persan polonais portugais roumain russe serbe slovaque slovène suédois tchèque thai turc vietnamien

Significations et usages de Sulfonic_acid

Définition

sulfonic acid (n.)

1.an acid derived from sulphuric acid

   Publicité ▼

Définition (complément)

⇨ voir la définition de Wikipedia

Synonymes

sulfonic acid (n.)

sulphonic acid

   Publicité ▼

Dictionnaire analogique

sulfonic acid (n.)

chemistry[Domaine]

CompoundSubstance[Domaine]

sulfone (fr)[Dérivé]

acid[Hyper.]


Wikipedia

Sulfonic acid

                   
  General structure of sulfonic acid.

A sulfonic acid (sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula RS(=O)2–OH, where R is an organic alkyl or aryl group and the S(=O)2–OH group a sulfonyl hydroxide.[1] A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the hypothetical compound sulfurous acid. Salts or esters of sulfonic acids are called sulfonates.

Contents

  Preparation

Sulfonic acid is produced by the process of sulfonation. Usually the sulfonating agent is sulfur trioxide. A particularly large scale application of this method is the production of alkylbenzenesulfonic acids:

RC6H5 + SO3 → RC6H4SO3H

In this reaction, sulfur trioxide is an electrophile and the arene undergoes electrophilic aromatic substitution.[1]

Thiols can be oxidized to sulfonic acids:

RSH + 3/2 O2 → RSO3H

Certain sulfonic acids, such as perfluorooctanesulfonic acid are prepared by electrophilic fluorination of preformed sulfonic acids. The net conversion can be represented simplistically:

C8H17SO3H + 17 F2 → C8F17SO3H + 17 HF
  Ball-and-stick model of methanesulfonic acid.

  Properties

Sulfonic acids are much stronger acids than the corresponding carboxylic acids. p-Toluenesulfonic acid, with a pKa of -2.8, is about a million times stronger acid than benzoic acid, with a pKa of 4.2. Similarly, methanesulfonic acid, pKa = -1.9, is also about one million times stronger acid than acetic acid. Because of their polarity, sulfonic acids tend to be crystalline solids. They are also usually colourless and nonoxidizing, which is convenient. Because of their high acidity, sulfonic acids are often soluble in water or exhibit detergent-like properties.

The structure of sulfonic acids is illustrated by the prototype, methanesulfonic acid. The sulfonic acid group, RSO2OH features a tetrahedral sulfur centre, meaning that sulfur is at the center of four atoms: three oxygens and one carbon. The overall geometry of the sulfur centre is reminiscent of the shape of sulfuric acid.

  Applications

Although both alkyl and aryl sulfonic acids are known, most of the applications are associated with the aromatic derivatives.

  Detergents and surfactants

Detergents and surfactants are molecules that combine highly nonpolar and highly polar groups. Traditionally, soaps are the popular surfactants, being derived from fatty acids. Since the mid-20th century, the usage of sulfonic acids has surpassed soap in advanced societies. For example, an estimated 2 billion kilograms of alkylbenzenesulfonates are produced annually for diverse purposes. Lignin sulfonates, produced by sulfonation of lignin are components of drilling fluids and additives in certain kinds of concrete.[2]

  Dyes

Many if not most of the anthroquinone dyes are produced or processed via sulfonation.[3] Sulfonic acids tend to bind tightly to proteins and carbohydrates. Most "washable" dyes are sulfonic acids (or have the functional sulfonyl group in them) for this reason. p-Cresidinesulfonic acid is used to make food dyes.

  Acid catalysts

Being strong acids, sulfonic acids are also used as catalysts. The simplest examples are methanesulfonic acid, CH3SO2OH and p-toluenesulfonic acid, which are regularly used in organic chemistry as acids that are lipophilic (soluble in organic solvents). Polymeric sulfonic acids are also useful. Dowex resin are sulfonic acid derivatives of polystyrene and is used as catalysts and for ion exchange (water softening).Nafion, a fluorinated polymeric sulfonic acid is a component of proton exchange membranes in fuel cells.[4]

  Drugs

Antibacterial drugs sulfa drugs are produced from sulfonic acids.

  Reactions

  Esterification

Sulfonic acids can be converted to esters. This class of organic compounds has the general formula R-SO2-OR. Sulfonic esters such as methyl triflate are considered good alkylating agents in organic synthesis. Such sulfonate esters are often prepared by alcoholysis of the sulfonyl chlorides:

RSO2Cl + R'OH → RSO2OR' + HCl
  Methyl triflate

  Chlorination

Sulfonyl halide groups occur when a sulfonyl functional group is singly bonded to a halogen atom. They have the general formula R-SO2-X where X is a halide, almost invariably chloride. They are produced by chlorination of sulfonic acids using thionyl chloride and related reagents.

  Displacement

Although the C-SO3H bond is strong, the (aryl)C-SO3 bond can be cleaved by certain nucleophiles. Of historic and continuing significance is the α-sulfonation of anthroquinone followed by displacement of the sulfonate group by other nucleophiles, which cannot be installed directly.[3] An early method for producing phenol involved the base hydrolysis of sodium benzenesulfonate, which can be generated readily from benzene.[5]

C6H5SO3Na + 2 NaOH → C6H5ONa + Na2SO3 + H2O

  Environmental concerns

Sulfonic acid derivatives are generally not derived from natural precursors and tend to biodegrade slowly. Some, such as perfluorooctane sulfonic acid, have been detected in the serum of humans. This should be not surprising as all organic fluorine compounds have extreme stability, and low to zero biodegradability. Many are intended to withstand harshest chemical conditions, for example teflon.[6] The nonfluorinated sulfonic acids tend to have low toxicities.[7]

  References

  1. ^ a b March, J. “Advanced Organic Chemistry” 4th Ed. J. Wiley and Sons, 1992: New York. ISBN 0-471-60180-2.
  2. ^ Kosswig, K. “Surfactants” in Ullmann’s Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a25_747.
  3. ^ a b Hans-Samuel Bien, Josef Stawitz, Klaus Wunderlich “Anthraquinone Dyes and Intermediates” Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinhem. doi:10.1002/14356007.a02_355
  4. ^ Guido Busca "Acid Catalysts in Industrial Hydrocarbon Chemistry" Chem. Rev. 2007, 107, 5366-5410. doi:10.1021/cr068042e
  5. ^ Manfred Weber, Markus Weber, Michael Kleine-Boymann "Phenol" in Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH. doi:10.1002/14356007.a19_299.pub2.
  6. ^ Bin Wang, Fukuya Iino, Gang Yu, Jun Huang, Masatoshi Morita "The Pollution Status of Emerging Persistent Organic Pollutants in China" Environmental Engineering Science. 2010, volume 27, p. 215-225. doi:10.1089/ees.2009.0337
  7. ^ Greim H., J. Ahlers, R. Bias, B. Broecker, H. Hollander, H.-P. Gelbke, H.-J. Klimisch, I. Mangelsdorf, A. Paetz, N Schön, G. Stropp, R. Vogel, C. Weber, K. Ziegler-Skylakakis, E. Bayer "Toxicity and ecotoxicity of sulfonic acids: Structure-activity relationship" Chemosphere Volume 28, Issue 12, June 1994, Pages 2203-2236. doi:10.1016/0045-6535(94)90188-0

  Other reading

  • J.A. Titus, R. Haugland, S.O. Sharrow and D.M. Segal, Texas red, a hydrophilic, red-emitting fluorophore for use with fluorescein in dual parameter flow microfluorometric and fluorescence microscopic studies. J. Immunol. Methods 50 (1982), pp. 193–204. doi:10.1016/0022-1759(82)90225-3 PMID 6806389
  • C. Lefevre, H.C. Kang, R.P. Haugland, N. Malekzadeh, S. Arttamangkul, and R. P. Haugland, Texas Red-X and Rhodamine Red-X, New Derivatives of Sulforhodamine 101 and Lissamine Rhodamine B with Improved Labeling and Fluorescence Properties, Bioconj Chem 1996, 7(4):482-9 doi:10.1021/bc960034p
   
               

 

Toutes les traductions de Sulfonic_acid


Contenu de sensagent

  • définitions
  • synonymes
  • antonymes
  • encyclopédie

dictionnaire et traducteur pour sites web

Alexandria

Une fenêtre (pop-into) d'information (contenu principal de Sensagent) est invoquée un double-clic sur n'importe quel mot de votre page web. LA fenêtre fournit des explications et des traductions contextuelles, c'est-à-dire sans obliger votre visiteur à quitter votre page web !

Essayer ici, télécharger le code;

SensagentBox

Avec la boîte de recherches Sensagent, les visiteurs de votre site peuvent également accéder à une information de référence pertinente parmi plus de 5 millions de pages web indexées sur Sensagent.com. Vous pouvez Choisir la taille qui convient le mieux à votre site et adapter la charte graphique.

Solution commerce électronique

Augmenter le contenu de votre site

Ajouter de nouveaux contenus Add à votre site depuis Sensagent par XML.

Parcourir les produits et les annonces

Obtenir des informations en XML pour filtrer le meilleur contenu.

Indexer des images et définir des méta-données

Fixer la signification de chaque méta-donnée (multilingue).


Renseignements suite à un email de description de votre projet.

Jeux de lettres

Les jeux de lettre français sont :
○   Anagrammes
○   jokers, mots-croisés
○   Lettris
○   Boggle.

Lettris

Lettris est un jeu de lettres gravitationnelles proche de Tetris. Chaque lettre qui apparaît descend ; il faut placer les lettres de telle manière que des mots se forment (gauche, droit, haut et bas) et que de la place soit libérée.

boggle

Il s'agit en 3 minutes de trouver le plus grand nombre de mots possibles de trois lettres et plus dans une grille de 16 lettres. Il est aussi possible de jouer avec la grille de 25 cases. Les lettres doivent être adjacentes et les mots les plus longs sont les meilleurs. Participer au concours et enregistrer votre nom dans la liste de meilleurs joueurs ! Jouer

Dictionnaire de la langue française
Principales Références

La plupart des définitions du français sont proposées par SenseGates et comportent un approfondissement avec Littré et plusieurs auteurs techniques spécialisés.
Le dictionnaire des synonymes est surtout dérivé du dictionnaire intégral (TID).
L'encyclopédie française bénéficie de la licence Wikipedia (GNU).

Copyright

Les jeux de lettres anagramme, mot-croisé, joker, Lettris et Boggle sont proposés par Memodata.
Le service web Alexandria est motorisé par Memodata pour faciliter les recherches sur Ebay.
La SensagentBox est offerte par sensAgent.

Traduction

Changer la langue cible pour obtenir des traductions.
Astuce: parcourir les champs sémantiques du dictionnaire analogique en plusieurs langues pour mieux apprendre avec sensagent.

 

4212 visiteurs en ligne

calculé en 0,031s


Je voudrais signaler :
section :
une faute d'orthographe ou de grammaire
un contenu abusif (raciste, pornographique, diffamatoire)
une violation de copyright
une erreur
un manque
autre
merci de préciser :