Methyl polarity reversal

Commercially available water soluble copolymers of maleic anhydride with ethylene and methyl vinyl ether (presumably partially hydrolyzed to vicinal carboxylic acids) and triphenylsulfonium triflate were dissolved in water as a casting solvent. Spin-cast films were baked at 130 °C for 10 s, exposed to 254 nm radiation, and postexposure-baked at 130 °C for 40 s. Development with pure water provided negative tone images, presumably due to acid-catalyzed dehydration between vicinal carboxylic acids to form less polar anhydride, as was demonstrated for polarity reversal (4.3.1). However, a copolymer of maleic acid with methyl vinyl ether failed to provide any negative images,... 

In 1994, only 15% of EPA method validations (tolerance method validation and environmental chemistry method validations) that involved GC were carried out using GC/MS. In 2002, this number is reversed in that 85% of the GC methods that were validated by both programs used GC/MS. Many of the compounds investigated in these method trials were polar compounds, and hence these compounds required derivatization in order to be amenable to GC. One common methylating agent is (trimethylsilyl)diazomethane, which is used, for example, to methylate the sulfonamide flumetsulam. As opposed to HPLC/MS, where derivatization is often not necessary, the GC/MS procedure involves an extra step to methylate this compound, under dry conditions, prior to determination by GC/MS. 

In this experiment, a mixture of methyl, propyl, and butyl paraben (structures shown in Figure 13.14) in methanol solvent will be separated by reverse phase HPLC. Mobile phase compositions of varying polarities will first be tested to see which one gives the optimum resolution of this mixture, and following this, a standard curve for methyl paraben will be constructed and its concentration in this solution determined. 

If solutes dissolve only in nonpolar or weakly polar solvents, the decision tree suggests that we try reversed-phase chromatography. Our choices include bonded phases containing octadecyl (CJg), octyl, butyl, ethyl, methyl, phenyl, and cyano groups. 

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