Sulfuric acid, reaction with sulfonic acids

Zinc chloride is a Lewis acid catalyst that promotes cellulose esterification. However, because of the large quantities required, this type of catalyst would be uneconomical for commercial use. Other compounds such as titanium alkoxides, eg, tetrabutoxytitanium (80), sulfate salts containing cadmium, aluminum, and ammonium ions (81), sulfamic acid, and ammonium sulfate (82) have been reported as catalysts for cellulose acetate production. In general, they require reaction temperatures above 50°C for complete esterification. Relatively small amounts (<0.5%) of sulfuric acid combined with phosphoric acid (83), sulfonic acids, eg, methanesulfonic, or alkyl phosphites (84) have been reported as good acetylation catalysts, especially at reaction temperatures above 90°C. 

Alkylphenol. Alkylphenol is a common surfactant intermediate used to produce alkylphenol ethoxylates. Phenol reacts with an olefin thermally without a catalyst but with relatively poor yields. Catalysts for the reaction include sulfuric acid p-toluene sulfonic acid (PTSA), strong acid resins, and boron trifluoride (BF3). Of these, strong acid resins and BF3 are mostly widely used for the production of surfactant-grade alkylphenols. The most common alkylphenols are octylphenol, nonylphenol, and dodecylphe-nol. Mono nonylphenol (MNP) is by far the most common hydrophobe. It is produced by the alkylation of phenol with nonene under acid conditions. All commercially produced MNP is made with nonene based on propylene trimer. Because of the skeletal rearrangements that occur during propylene oligomerization, MNP is a complex mixture of branched isomers. 

Benzene and toluene are insoluble in sulfuric acid, whereas the sulfonic acids are readily soluble completion of reaction is indicated simply by disappearance of the hydrocarbon layer. When shaken with fuming sulfuric acid at room temperature, benzene reacts completely within 20 to 30 minutes, whereas toluene is found to react within only a minute or two. 

The hydrolysis of epoxidised soybean oil was investigated in the presence of acidic catalysts (sulfuric acid, p-toluene sulfonic acid, phosphoric acid). The objective was to obtain a maximum hydroxyl number with a minimum hydrolysis of the ester bonds [58]. The idealised reaction for epoxidised soybean oil hydrolysis is presented in reaction 17.20. 

A mixture of ester is obtained, and the ratio of monoester to diester is controlled by ratios of the compounds charged to the reactor. Excess polyoxyethylene is used to maximize monoester production (5), and excess fatty acid is used to maximize diester formation (6). Because of the existing equilibrium, it is important that water be removed with an azeotroping agent such as toluene, xylene, etc., and/or by use of an inert-gas sparge to carry off water as it is formed to force the equilibrium toward the desired product. Catalysts such as sulfuric acid (7), benzene sulfonic acid, and other aromatic sulfonic acids (5, 8, 9), as well as cationic ion-exchange resins such as polystyrene-sulfonic acids (5, 9), are used. The latter compounds have the advantage of easy removal from batch reactions and of use in a fixed bed for continuous processes. Metals such as tin, iron, and zinc, as well as their salts in powdered form, have been used as catalysts (10,11). Catalysts can improve the yield of monoester. Of course, use of a monohydroxyl-functional polyoxyethylene, such as that from methanol-started ethylene oxide polymers (methoxy-polyoxyethylene), can be esterified with fatty acids to yield effectively all monoester. 

Reaction of myrcene and sulfur dioxide under pressure produces myrcene sulfone. This adduct is stable under ordinary temperatures and provides a way to stabilize the conjugated diene system in order to hydrate it with sulfuric acid. The myrcene sulfone hydrate produced is pyrolyzed in the vapor phase in order to regenerate the diene system to produce myrcenol [543-39-5] (50). 

Sulfinic esters, aromatic, by oxidation of disulfides in alcohols, 46, 64 Sulfonation ot d,l camphor to d,l-10-camphorsulfomc acid, 45,12 Sulfoxides, table of examples of preparation from sulfides with sodium metapenodate, 46,79 Sulfur dioxide, reaction with styrene phosphorus pentachlonde to give styrylphosphomc diclilonde, 46,... 

Sulfonation of an aromatic substrate to produce ArSOaH is usually brought about by reaction of the aromatic with concentrated sulfuric acid or with sulfur... 

The hydrocarbon base is petroleum derived and does, in fact, contain a distribution of chain lengths with the predominant species being C. In addition, there can be a greater or lesser degree of chain branching. The sulfonation process utilized can vary from direct reaction with sulfuric acid to SO /SO mixtures, but always results in some excess sulfuric acid. On neutralization, a proportion of sodium sulfate is produced which is preferably kept to a minimum for admixture formulations. 

Two of the reactions that are used in the industrial preparation of detergents are electrophilic aromatic substitution reactions. First, a large hydrocarbon group is attached to a benzene ring by a Friedel-Crafts alkylation reaction employing tetrapropene as the source of the carbocation electrophile. The resulting alkylbenzene is then sulfonated by reaction with sulfuric acid. Deprotonation of the sulfonic acid with sodium hydroxide produces the detergent. 

In sulfonation reactions with chlorosulfonic acid, as well as with sulfuric acid and oleum, small amounts of sulfones are often formed as by-products. The sulfone is formed by the reaction of the sulfonic acid with unchanged starting material under the influence of the dehydrating action of the sulfonation reagent, according to the equation ... 

Frequently, the 1,5- and 1,8-disulfonic acids are not isolated separately, but are taken out of the reaction mixture together. For this purpase, the sulfonation mixture is first diluted with concentrated sulfuric acid, then with sufBcient water to make the solution 60 per cent with respect to sulfuric acid. 

Sulfones are often produced as by-products in the sulfonation of aromatic hydrocarbons (method 540). Aromatic hydrocarbons react with sulfonic acids less readily than with sulfuric acid. The success of the reaction depends upon the removal of the water as it is formed. An automatic water separator is used in the conversion of a refluxing mixture of benzene and sulfuric acid to diphenyl sulfone (80%). A similar technique has been employed in the preparation of unsymmetrical sulfones. 

Introduction. It will be recalled that one of the most common methods of distinguishing between aromatic and aliphatic hydrocarbons is the difference in the rates of their reactions with sulfuric acid. Aromatic hydrocarbons readily form sulfonic acids when heated with concentrated sulfuric acid at temperatures varying from 80 to 200 . Saturated paraffin hydrocarbons, on the other hand, do not react with sulfuric acid under comparable conditions. A number of saturated paraffins are sulfonated directly by using fuming sulfuric acid and heating under pressure, but the sulfonic acids of the lower paraffin hydrocarbons are prepared by reacting alkyl halides with alkali sulfites. The sulfonic acids of the aromatic hydrocarbons are of much greater importance than the sulfonic acids of paraffins. 

Preferably the reaction in accordance with the invention is performed in the presence of a suitable catalyst, proton acids such as for instance haloid acids, sulfuric acid, phosphoric acid, perchloric acid, organic sulfonic acids, such as for instance methanesulfonic acid and p-toluenesulfonic acid, carboxylic acids, such as for instance oxalic acid, trifluoroacetic acid and other Lewis acids, such for instance boron trifluoride, ferric chloride, zinc chloride, zinc bromide, stannic chloride, titanium chloride or iodine having proved to be suitable. Furthermore mixtures of the individual catalysts may be used in certain cases. 

Properties Pinkish-white to gray needles. Soluble in hot water but almost insoluble in cold water. Derivation (3-naphthol is nitrated to mtroso-ji-naphthol by reaction with nitrous acid and the product treated with sodium bisulfite. Upon acidification the free sulfurous acid effects simultaneous reduction and sulfonation. 

Sommelet reaction, 33, 93 Sorbic acid, 5-hydroxy-/3-methyl, J-lactone, 32, 57 Stannic chloride, 33, 91 Stearic acid, 34, 15 Stearone, 33, 84 cis-Stilbene, 33, 88 fraws-Stilbene, 33, 89 Stirrer, for caustic fusion, 30, 104, 105 seal for, 30, 54 Stobbe condensation, 30, 18 Styrene, 33, 72 34, 85 reaction with sulfuric acid, 35, 83 Styrene dibromide, 30, 73 Styrene oxide, 31, 3 0-Styrenesulfonyl chloride, 34, 85 Succinic acid, 34, 44 Succinic acid, < -benzhydrylidene-, a-ETHYL ESTER, 30, 18 CLNNAMYL-, 31, 85 DIPHENYL ESTER, 34, 44 HEPTANOYL-, DIETHYL ESTER, 34, 51 PHENYL-, 30, 83 Succinic anhydride, 34, 40 SUCCINONITRILE, a, -DIPHENYL-, 32, 63 Sulfide, methyl 2-thienyl, 35, 85 Sulfonation of styrene, 34, 85 Sulfonyl chloride, from sodium sulfonate, 34, 85... 

ESTANO (Spanish) (7440-31-5) Finely divided material is combustible and forms explosive mixture with air. Contact with moisture in air forms tin dioxide. Violent reaction with strong acids, strong oxidizers, ammonium perchlorate, ammonium nitrate, bis-o-azido benzoyl peroxide, bromates, bromine, bromine pentafluoride, bromine trifluoride, bromine azide, cadmium, carbon tetrachloride, chlorine, chlorine monofluoride, chlorine nitrate, chlorine pentafluoride, chlorites, copper(II) nitrate, fluorine, hydriodic acid, dimethylarsinic acid, ni-trosyl fluoride, oxygen difluoride, perchlorates, perchloroethylene, potassium dioxide, phosphorus pentoxide, sulfur, sulfur dichloride. Reacts with alkalis, forming flammable hydrogen gas. Incompatible with arsenic compounds, azochloramide, benzene diazonium-4-sulfonate, benzyl chloride, chloric acid, cobalt chloride, copper oxide, 3,3 -dichloro-4,4 -diamin-odiphenylmethane, hexafluorobenzene, hydrazinium nitrate, glicidol, iodine heptafluoride, iodine monochloride, iodine pentafluoride, lead monoxide, mercuric oxide, nitryl fluoride, peroxyformic acid, phosphorus, phosphorus trichloride, tellurium, turpentine, sodium acetylide, sodium peroxide, titanium dioxide. Contact with acetaldehyde may cause polymerization. May form explosive compounds with hexachloroethane, pentachloroethane, picric acid, potassium iodate, potassium peroxide, 2,4,6-trinitrobenzene-1,3,5-triol. 

Reactions 3, 4, 5, and 6 would then ensue with sulfonic acid being the catalytic peroxide decomposer, and the major source of H+ for the induced decomposition of the thiolsulfinate. The disproportionation of thiolsul-finates is accelerated markedly by the addition of substances such as alkyl sulfides that contain a more nucleophilic sulfur atom than found in thiolsulfinates. 

EXPLOSION and FIRE CONCERNS not combustible, but extremely irritating if involved in a fire combination with water evolves heat NFPA rating Health 4, Flammability 0, Reactivity 1 reacts explosively with cyanogen fluoride, glycerol and nitric acid, and methane-sulfonic acid violent reaction with acetic anhydride, 2-aminoethanol, chlorosulfonic acid, ethylene diamine, propylene oxide, vinyl acetate, sodium hydroxide, and sulfuric acid liquid hydrogen fluoride reacts incandescently with arsenic trioxide and calcium oxide reacts with water or steam to produce toxic and corrosive fumes incompatible with most metals, water and alkali... 

Nafion is a perfluorinated polymer with sulfonic acid groups grafted to side chains, yielding acidity similar to that of sulfuric acid [5]. Nafion has not been extensively studied as a catalyst for isoparaffin alkylation, although it has shown good activity for a number of acid catalyzed reactions [6-9]. Nafion is available in both unsupported and supported forms. In the supported form, the polymer is impregnated on high surface area silica supports, which has been shown to improve accessibility to acid sites [10,11]. 

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