Sulfones, vinyl Sulfonic acids

Ethyl /m s -2-butenyl sulfone (86) together with some ethyl vinyl sulfone are obtained by the reaction of ethylene and. SO2 in wet benzene using PdCl2. SO2 behaves mechanistically similarly to CO in this reaction[66]. Hydrosulfination of alkenes with SO2 and H2 is catalyzed by the Pd(dppp) complex. The sulfinic acid 87 is a primary product, which reacts further to give the. S-alkyl alkanethiosulfonates 88 as the major product, and 89 and the sulfonic acid 90 as minor products[67]. 

The simplest monomer, ethylenesulfonic acid, is made by elimination from sodium hydroxyethyl sulfonate and polyphosphoric acid. Ethylenesulfonic acid is readily polymerized alone or can be incorporated as a copolymer using such monomers as acrylamide, aHyl acrylamide, sodium acrylate, acrylonitrile, methylacrylic acid, and vinyl acetate (222). Styrene and isobutene fail to copolymerize with ethylene sulfonic acid. 

Poly(vinyl alcohol) is readily cross-linked with low molecular weight dialdehydes such as glutaraldehyde or glyoxal (163). Alkanol sulfonic acid and poly(vinyl alcohol) yield a sulfonic acid-modified product (164). 

S824). More recently, this method was employed for the synthesis of 3-methyl-5-vinyl isotellurazole If (87H1587). It was assumed that the reaction occurs through the intermediate oxime-O-sulfonic acids 2. 

Homopolymers and copolymers from amido-sulfonic acid or salt containing monomers can be prepared by reactive extrusion, preferably in a twin screw extruder [1660]. The process produces a solid polymer. Copolymers of acrylamide, N-vinyl-2-pyrrolidone, and sodium-2-acrylamido-2-methyl-propane sulfonate have been proposed to be active as fluid loss agents. Another component of the formulations is the sodium salt of naphthalene formaldehyde sulfonate [207]. The fluid loss additive is mixed with hydraulic cements in suitable amounts. 

N-vinyl acetamide, or dimethylamino ethyl methacrylate, 2-acrylamido-2-methylpropane sulfonic acid, sodium vinyl sulfonate, and vinylbenzene sulfonate... 

Lignin, brown coal polymer of methacrylic acid, methacrylamide, hydroxyethyl acrylate, hydroxypropyl acrylate, vinyl acetate, methyl vinyl ether, ethyl vinyl ether, N-methylmeth-acrylamide, N,N-dimethylmethacrylamide, vinyl sulfonate, or 2-acrylamido-N-methylpropane sulfonic acid free radical polymerization of a water-soluble vinyl monomer in an aqueous suspension of coals [705,1847]... 

However, the mechanism of action of filtration control additives is not yet completely understood. Examples are bentonite, latex, various organic polymers, and copolymers. Many additives for fluid loss are water-soluble polymers. Vinyl sulfonate fluid loss additives based on the 2-acrylamido-2-methyl-propane sulfonic acid (AMPS) monomer are in common use in field cementing operations [363]. The copolymerization of AMPS with conjugate monomers yields a fluid loss agent whose properties include minimal retardation, salt tolerance, high efficiency, thermal stability, and excellent solids support. 

Figure 17-4. Vinyl modifiers for guar gum 2-acrylamido-2-methylpropane sulfonic acid, 1 -allyloxy-2-hydroxypropyl sulfonic acid.

Vinyl phosphonic acid N-Vinylpyrrolidone Vinyl sulfonic acid... 

Figure 17-8. Monomers for synthetic thickeners vinyl phosphonic acid, N-vinyl-2-pyrrolidone, vinyl sulfonic acid.

A dispersant that can be used in drilling fluids, spacer fluids, cement slurries, completion fluids, and mixtures of drilling fluids and cement slurries controls the rheologic properties of and enhances the filtrate control in these fluids. The dispersant consists of polymers derived from monomeric residues, including low-molecular-weight olefins that may be sulfonated or phosphonated, unsaturated dicarboxylic acids, ethylenically unsaturated anhydrides, unsaturated aliphatic monocarboxylic acids, vinyl alcohols and diols, and sulfonated or phosphonated styrene. The sulfonic acid, phosphonic acid, and carboxylic acid groups on the polymers may be present in neutralized form as alkali metal or ammonium salts [192,193]. 

Copolymers of Acrylic Acid and Vinyl Sulfonic Acid... 

Excess acidity correlations have been used to show that some aromatic sulfonic acid desulfonations have an A-SE2 mechanism.188,189 This mechanism (alternative terminologies are Ad-E2 and A(E) +A(N))190 has also been found to apply to the hydration of acetylene itself,191 to ynamines192 and to many other alkynes,193-195 as well as to many different alkenes196-199 and vinyl ethers.200-203 The excess acidity method has been used to evaluate aA values for several alkene hydrations.204 205... 

Most immobilization methods require modification of the ligands for anchoring to the support by introducing functional groups such as vinyl, trialkoxysilyl, sulfonic acid, and amino groups. The consequence is often a more elaborate synthesis of the ligand, which adds to the costs of an immobilized catalyst. However, two interesting approaches were developed in recent years, when unmodi-... 

Since PTFE was first synthesized more than 50 years ago, fluoropolymers have been produced by radical polymerization and copolymerizaton processes, but without any functional groups, for several reasons. First, the synthesis of functional vinyl compounds suitable for radical polymerization is much more complicated and expensive in comparison with common fluoroolefins. In radical polymerization of one of the simplest possible candidates—perfluorovinyl sulfonic acid (or sulfonyl fluoride—there was not enough reactivity to provide high-molecular-weight polymers or even perfluorinated copolymers with considerable functional comonomer content. Several methods for the synthesis of the other simplest monomer—trifluoroacrylic acid or its esters—were reported,1 but convenient improved synthesis of these compounds as well as radical copolymerization with TFE induced by y-irradiation were not described until 1980.2... 

For instance, the Dow experimental membrane and the recently introduced Hyflon Ion E83 membrane by Solvay-Solexis are "short side chain" (SSC) fluoropolymers, which exhibit increased water uptake, significantly enhanced proton conductivity, and better stability at T > 100°C due to higher glass transition temperatures in comparison to Nafion. The membrane morphology and the basic mechanisms of proton transport are, however, similar for all PFSA ionomers mentioned. The base polymer of Nation, depicted schematically in Figure 6.3, consists of a copolymer of tetrafluoro-ethylene, forming the backbone, and randomly attached pendant side chains of perfluorinated vinyl ethers, terminated by sulfonic acid head groups. °... 

Nafion is a copolymer of poly(tetrafluoroethylene) and polysulfonyl fluoride vinyl ether. It has fixed anions, which are sulfonic acid sites, and consequently, by electroneutrality, the concentration of positive ions is fixed. Furthermore, the transference number of protons in this system is 1, which greatly simplifies the governing transport equations, as seen below. There can be different forms of Nafion in terms of the positive counterion (e.g., proton, sodium, etc.). Most models deal only with the proton or acid form of Nafion, which is the most common form used in polymer-electrolyte fuel cells due to its high proton conductivity. 

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