Paraffin sulfonic acid

Trimellitates, paraffinic sulfonic acid and phenyl esters, poly(es-ter)s, chlorinated hydrocarbons, aliphatic or aromatic monocarbox-ylic acid esters such as benzoates, and a variety of elastomers are common plasticizers. 

Surfactants are prepared which contain carboxylic acid ester or amide chains and terminal acid groups selected from phosphoric acid, carboxymethyl, sulfuric acid, sulfonic acid, and phosphonic acid. These surfactants can be obtained by reaction of phosphoric acid or phosphorus pentoxide with polyhydroxystearic acid or polycaprolactone at 180-190°C under an inert gas. They are useful as polymerization catalysts and as dispersing agents for fuel, diesel, and paraffin oils [69]. 

The sulfoxidation of aliphatic hydrocarbons is the easiest method for the synthesis of alkylsulfonic acids. Their sodium salts are widely used as surfactive reactants in technology and housekeeping. Platz and Schimmelschmidt [1] were the first to invent this synthetic method. Normal paraffins (Ci4-Cig) are used for the industrial production of alkylsulfonic acids [2-4]. Olefins and alkylaromatic hydrocarbons do not produce sulfonic acids under the action of sulfur dioxide and dioxygen and retard the sulfoxidation of alkanes [5-9],... 

A wide range of anionic surfactants (Fig. 23) has been classified into groups, including alkyl benzene sulfonates (ABS), linear alkyl benzene sulfonates (LAS), alcohol sulfates (AS), alcohol ether sulfates (AES), alkyl phenol ether sulfates (APES), fatty acid amide ether sulfates (FAES), alpha-olefin sulfates (AOS), paraffin sulfonates, alpha sulfonated fatty acids and esters, sulfonated fatty acids and esters, mono- and di-ester sulfosuccinates, sulfosuccinamates, petroleum sulfonates, phosphate esters, and ligno-sulfonates. Of the anionic surfactants, ABS and LAS continue to be the major products of anionic surfactants [314, 324]. Anionic surfactants have been extensively monitored and characterized in various environmental matrices [34,35,45,325-329]. 

Some work [5] has been performed on the photochemical reaction between sulfur dioxide and hydrocarbons, both paraffins and olefins. In all cases, mists were found, and these mists settled out in the reaction vessels as oils with the characteristics of sulfuric acids. Because of the small amounts of materials formed, great problems arise in elucidating particular steps. When NO and O2 are added to this system, the situation is most complex. Bufalini [3] sums up the status in this way The aerosol formed from mixtures of the lower hydrocarbons with NO , and SO2 is predominantly sulfuric acid, whereas the higher olefin hydrocarbons appear to produce carbonaceous aerosols also, possibly organic acids, sulfuric or sulfonic acids, nitrate-esters, etc. ... 

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. 

N,N -Dimethylacetamide (DMAc) (Aldrich, HPLC grade) was used without further purification. Acetic anhydride (BDH) was pre-dried over anhydrous sodium acetate. Pyridine (Aldrich, anhydrous) was distilled from KOH prior to use. Poly(maleic anhydride-co-octadec-l-eneXl l) (Polysciences), as a polymeric stabilizer, was used as supplied. Paraffin oil (A.J. Beveridge Ltd., liquid paraffin 5LT) was used as a suspending medium. Pyromellitic dianhydride (1,2,4,5-benzenetetracarboxylic dianhydride) (Aldrich) was recrystallized from butan-2-one before use. p-Phenylenediamine (Aldrich) and 2,6-diaminopyridine (Aldrich) were recrystallized from ethanol. 3,5-Diaminobenzoic acid (Aldrich) and 2,5-diaminobenzene sulfonic acid (Aldrich) were recrystallized from water and heated at HOT) under vacuum to remove water. 3,5-Diamino-l,2,4-triazole (Aldrich) and tris(2-aminoethyl)amine (Tokyo Kasei) were without further purification. 

N,N -dimethylacetamide was prepared from pyromellitic dianhydride and the functional diamines, 3,S-diamino-l,2,4-triazole 2,5-diaminobenzoic acid 2,5-diaminobenzene sulfonic acid or 2,6-diaminopyridine. Each pre-polymer solution was then dispersed as droplets in paraffin oil containing poly(maleic anhydride-co-octadec-l-eneXl l) as a suspension stabilizer, and imidization induced at 60C by addition of a mixture of acetic anhydride and pyridine (Figure 1). 

The traditional method of manufacturing is by a separation method (like most traditional methods) with a solvent extracted and dewaxed base oil as the usual feedstock. By reaction of either a paraffinic or a naphthenic base oil with oleum, aromatics are converted to the corresponding sulfonic acids and separate out. This may require several mixing steps to complete reaction of all the aromatics. Paraffins and naphthenes are essentially unaffected by the acid treatment.7 After separation of the sulfonic acids, the remaining oil, now free of aromatics, is neutralized with caustic, washed with alcohol, and finally treated with bauxite or clay. Figure 11.1 provides a schematic for this type of process. 

KC-Q KC-X KC-Z1 KC-Z2-Z3 KC-Z4 KC-Z5-Z6. See Linseed (Linum usitatissimum) oil K-Cellsy. See Cellulose K-Cure 1040W. See p-Toluene sulfonic acid KCW46-150. See Paraffin, chlorinated KD-61. See Petrolatum KD-96. See 1,1,1-Trimethylolpropane trimethacrylate... 

Monurox Monuruon. See Monuron Moorelube 165, Moorelube 165AW, Moorelube 165P. See Paraffin 5-MOP. See 5-Methoxypsoralen MOPA. See p-Methoxyphenylacetic acid MOPS MOPS. See 3-(N-Morpholino)-propane sulfonic acid... 

Petroleum sulfonates, sodium salts Petroleum sulfonic acid, monosodium salt. See Sodium petroleum sulfonate Petroleum thinner. See VM P naphtha Petroleum wax CAS 977051-70-9 UN 1223 (DOT) INS905c Synonyms Microcrystalline wax Petroleum wax, synthetic Refined petroleum wax Classification Petroleum hydrocarbon Definition Hydrocarbon derived from petroleum three types paraffin waxes, microcrystalline waxes, and petrolatum waxes Properties Translucent wax, odorless, tasteless very si. sol. in org. soivs. insol. in water m.p. 48-93 C... 

Surfactant alkylbenzene sulfonate, paraffin sulfonate, alkyl sulfate, ethoxylated alcohol sulfate, ethoxylated alcohol, alkanol amide fatty acid, carbamates, amine oxide, ethoxylated alcohols, betaines Builder carbonates, citrates (Tielator EDTA Alkalinity sodium hydroxide, alkanolamines, sodium carbonate Acid phosphoric, dicarboxylic (like glutaric), citric, sulfamic, acetic Solvent alcohols, glycol ether Disinfectant quaternary ammonium surfactants... 

The other way to functionalize n-paraffins by introducing a sulfonic group is photosulfoxidation. The free-radical mechanism involves the direct replacement of a hydrogen atom by a sulfonic acid group, SO3H. The global sulfoxidation reaction is strongly exothermic. 

In (2), the heavier sulfonic acid-rich phase is separated from part of the residual hydrocarbon, which is recycled (13). The remaining paraffin is solubilized in sulfonic acid aggregates. In (3), the sulfur dioxide dissolved in the lower phase is expelled (10) by means of air (16). Water is then distilled off in vacuo (4), together with some paraffin, and on such concentration of the aqueous... 

FIGURE 7.5 Flowchart of the light-water sulfoxidation process. Photoreactor (1), separators (2,5,8,9), SOj stripper (3), evaporating column (4), neutralization reactor (6), evaporator (7), exhaust gas (10), fresh paraffin (11), sulfonic acid (12), recycle paraffin (13), recycle gas (14), acid phase (15), air (Oj) (16), back paraffin (17). (After Falbe, J., ed., Surfactants in Consumer Products Theory, Technology and Application, Springer, Berlin, 1986. With permission.)... 

Additives used in final products Fillers calcium carbonate, calcium hydroxide, calcium oxide, carbon black, polymeric beads, polystyrene particles, zinc oxide Plasticizers 1-isobutyrate benzyl phthalate, 2,2,4-tri-methyl-1,3-pentanediol, alkyl sulfonic acid esters of phenol and/or cresol, benzyl butyl phthalate, chlorinated paraffins, hydrogenated perphenyl, isooctyl benzyl phthalate Curatives metal peroxides, oxy salts (e.g., dioxides of lead, manganese, calcium, etc.) ... 

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