Oxidation of Aliphatic and Aromatic Sulfides Using Sulfuric Acid

Nehlsen, James; Benziger, and Jay; Kevrekidis, Ioannis G.

doi:10.1021/ie050901m

Cited by 21 publications

(10 citation statements)

References 13 publications

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“…Sulfuric acid and SO 3 , on the other hand, has been reported to be able to oxidize thiophenes at elevated temperatures, itself being reduced to H 2 SO 3 or SO 2 , respectively. 26,27 For SO 3 and TTh:…”

Section: Resultsmentioning

confidence: 99%

Toward a trace-free oxidant—insight into unexpected high yields of vapor phase polymerized polyterthiophene

Ong

Bayley

Winther‐Jensen

et al. 2012

Polym J

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Vapor phase polymerization (VPP) of conducting polymers has been widely reported as a versatile technique to obtain thin films with high conductivity and order. One oxidant commonly used for VPP is iron(III) para-toluenesulfonate (Fe(III)PTS) owing to its outstanding film-forming properties. The polymerization mechanism using Fe(III)PTS has been believed to follow the normal route, where (at least) two Fe(III) is needed for oxidizing one monomer unit to form the polymer. Surprisingly, when polymerizing terthiophene (TTh) monomers at 100 1C using Fe(III)PTS, it was found that B2.3 times more the expected amount of PTTh was produced, when long polymerization times were used. An explanation for the phenomenon was found when VPP of TTh was successful using only para-toluenesulfonic acid (PTSa) as oxidant. It is believed that PTSa is gradually converted to SO 3 and toluene at elevated temperature and that reduction of SO 3 is driving the oxidation of the TTh monomers. This finding also opens a useful oxidative polymerization route where the oxidant can be converted to volatile compounds leaving no trace in the end product.

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Section: Resultsmentioning

confidence: 99%

Toward a trace-free oxidant—insight into unexpected high yields of vapor phase polymerized polyterthiophene

Ong

Bayley

Winther‐Jensen

et al. 2012

Polym J

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“…Alcohols, the organic function present in the glucose molecule, are oxidized to ethers under action of this acid and heating (Solomons and Fryhle, 2001). In addition, Nehlsen et al (2006) found synergism between sulfuric acid and heating as oxidizing agents of aliphatic and aromatic sulfides, reducing the Gibbs free energy value for these reactions.…”

Section: Spectrophotometric Alternatives For Embrapa and Walkley-blacmentioning

confidence: 99%

Development of Alternative Methods for Determining Soil Organic Matter

Souza

Morais

Matsushige

et al. 2016

Rev. Bras. Ciênc. Solo

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Soil organic matter (SOM) is important to fertility, since it performs several functions such as cycling, water and nutrient retention and soil aggregation, in addition to being an energy requirement for biological activity. This study proposes new trends to the Embrapa, Walkley-Black, and Mebius methods that allowed the determination of SOM by spectrophotometry, increasing functionality. The mass of 500 mg was reduced to 200 mg, generating a mean of 60 % saving of reagents and a decrease of 91 % in the volume of residue generated for the three methods without compromising accuracy and precision. We were able to optimize conditions for the Mebius method and establish the digestion time of maximum recovery of SOM by factorial design and response surface. The methods were validated by the estimate of figures of merits. Between the methods investigated, the optimized Mebius method was best suited for determining SOM, showing near 100 % recovery.

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“…Oxidation of sulfides is a direct method to synthesize sulfoxides which play important roles in pharmaceutical, biologically active compounds, organic synthesis, and solvent extraction, − etc. Numerous studies about the oxidation of sulfides have been done over the years. − Aqueous H 2 O 2 is considered as an excellent oxidant for the oxidation of sulfides because it is cheap, efficient, highly chemoselective, and environmentally friendly. − Oxidation of sulfides with aqueous H 2 O 2 is a heterogeneous liquid–liquid reaction because of the immiscibility of organic sulfides and aqueous H 2 O 2 . In order to enhance the mass transfer between the two phases, organic solvents are always used. , The organic solvents used in the process are usually toxic and environmentally hazardous, which limit its scale-up.…”

Section: Introductionmentioning

confidence: 99%

Mechanism and Kinetic Model for Autocatalysis in Liquid–Liquid System: Oxidation of Dibutyl Sulfide with Aqueous Hydrogen Peroxide

Chen

Jin

et al. 2017

Ind. Eng. Chem. Res.

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The oxidation of dibutyl sulfide with aqueous hydrogen peroxide as a liquid−liquid reaction was investigated. The autocatalysis, solubility of H 2 O 2 in organic phase, and effects of temperature, stirring speed, initial organic DBSO concentration, and initial aqueous H 2 O 2 concentration were studied. Solvent effect of dibutyl sulfoxide was proposed for liquid−liquid autocatalysis. The intrinsic reaction was considered as the determining step, and all the other steps were considered as equilibrium processes. Considering interfacial reaction and dynamic equilibrium of hydrogen peroxide between the two phases, the reaction was divided into exterior and interior stages. Exterior and interior mechanisms were proposed for the corresponding stages, and kinetic models were established. The parameters of kinetic model were estimated with the experimental data, and the activation energies of exterior and interior reaction were 30.62 and 73.50 kJ/ mol. The validity of the kinetic models with estimated parameters was studied, and good agreements were observed between the experimental results and the model results.

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Oxidation of Aliphatic and Aromatic Sulfides Using Sulfuric Acid

Cited by 21 publications

References 13 publications

Toward a trace-free oxidant—insight into unexpected high yields of vapor phase polymerized polyterthiophene

Toward a trace-free oxidant—insight into unexpected high yields of vapor phase polymerized polyterthiophene

Development of Alternative Methods for Determining Soil Organic Matter

Mechanism and Kinetic Model for Autocatalysis in Liquid–Liquid System: Oxidation of Dibutyl Sulfide with Aqueous Hydrogen Peroxide

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