Alcohol ozonization

Chemical/Physical. The gas-phase reaction of ozone with pyridine in synthetic air at 23 °C yielded a nitrated salt having the formula [CeHsNHJ NOs (Atkinson et al., 1987). Ozonation of pyridine in aqueous solutions at 25 °C was studied with and without the addition of ferf-butyl alcohol (20 mM) as a radical scavenger. With tert-hniyX alcohol, ozonation of pyridine yielded mainly pyridine W-oxide (80% yield), which was very stable towards ozone. Without terf-butyl alcohol, the heterocyclic ring is rapidly cleaved forming ammonia, nitrate, and the amidic compound W-formyl oxamic acid (Andreozzi et al., 1991). 

Nhrobutanol (2-) Nitrogen Tetraoxlde Nitfo methane Octadecyl Alcohol Ozone Pentachlorobenzamlde Up lo the bailing point up 10 boiling pi. up to Ihe boiling point u a a 8 8 8 DuPont TofJon FEP 44 tf a... 

NItrobutanol (2-) Nitrogen Tetraoxide Nltrom ethane Octadecyl Alcohol Ozone... 

Nitrogen Tetraoxlde NItromettiane Octadecyl Alcohol Ozone... 

EPDM has a generally acceptable resistance to most moderate chemicals, alcohol, ozone, and organic acids. It is, however, attacked by strong acids, solvents, most hydrocarbons, chloroform, and aromatic solvents. The minimum temperature for use is -51°C (-60°F) and its maximum temperature is 177°C or 350°F. FPDM offers better abrasion resistance than butyl rubber. It is also used as a high-temperature gasket. Mechanical properties are presented in Table 10-13. 

Because the protonation of ozone removes its dipolar nature, the electrophilic chemistry of HOs, a very efficient oxygenating electrophile, has no relevance to conventional ozone chemistry. The superacid-catalyzed reaction of isobutane with ozone giving acetone and methyl alcohol, the aliphatic equivalent of the industrially significant Hock-reaction of cumene, is illustrative. 

Other Hydroperoxides. Several hydrotrioxides including alkyl hydrotrioxides, R—OOOH, have been reported (63,64). There is strong spectroscopic evidence that a-cumyl hydrotrioxide [82951-48-2] is produced in the low temperature ozonization of cumene. Homolytic decomposition of a-cumyl hydrotrioxide in cumene/acetone-hindered phenol resulted in cumyl alcohol as the only organic product (65). Based on the... 

Alkoxyall l Hydroperoxides. These compounds (1, X = OR , R = H) have been prepared by the ozonization of certain unsaturated compounds in alcohol solvents (10,125,126). 2-Methoxy-2-hydroperoxypropane [10027-74 ] (1, X = OR , R" = methyl), has been generated in methanol solution and spectral data obtained (127). A rapid exothermic decomposition upon concentration of this peroxide in a methylene chloride—methanol solution at 0°C has been reported (128). 2-Bromo-l-methoxy-l-methylethylhydroperoxide [98821-14-8]has been distilled (bp 60°C (bath temp.), 0.013 kPa) (129). Two cycHc alkoxyaLkyl hydroperoxides from cyclodecanone have been reported (1, where X = OR R, R = 5-oxo-l, 9-nonanediyl) with mp 94—95°C (R" = methyl) and mp 66—68°C (R" = ethyl) (130). Like other hydroperoxides, alkoxyaLkyl hydroperoxides can be acylated or alkylated (130,131). 

Vitamin D2 reacted with maleic anhydride to give a mono Diels-Alder adduct, which hydrolyzed to yield a dicarboxyhc acid. Acetylation of the alcohols, esterification of carboxyHc acids, and hydrogenation gave a compound that, when ozonized, gave a saturated ketone, This molecule... 

Ozone can be used to completely oxidize low concentrations of organics in aqueous streams or partially degrade compounds that are refractory or difficult to treat by other methods. Compounds that can be treated with ozone include alkanes, alcohols, ketones, aldehydes, phenols, benzene and its derivatives, and cyanide. Ozone readHy oxidizes cyanide to cyanate, however, further oxidation of the cyanate by ozone proceeds rather slowly and may require other oxidation treatment like alkaline chlorination to complete the degradation process. 

The resistance to heat and aging of optimized EPM/EPDM vulcanizates is better than that of SBR and NR. Peroxide-cured EPM can, for instance, be exposed for 1000 h at 150°C without significant hardening. Particularly noteworthy is the ozone resistance of EPM/EPDM vulcanizates. Even after exposure for many months to ozone-rich air of 100 pphm, the vulcanizates will not be seriously harmed. EPM/EPDM vulcanizates have an excellent resistance to chemicals, such as dilute acids, alkaUes, alcohol, etc. This is in contrast to the resistance to aUphatic, aromatic, or chlorinated hydrocarbons. EPM/EPDM vulcanizates swell considerably in these nonpolar media. 

This ether was prepared from an alcohol and 2-(phenylselenyl)ethyl bromide (AgN03, CH3CN, 20°, 10-15 min, 80-90% yield) it is cleaved by oxidation (H2O2, 1 h ozone or NaI04), followed by acidic hydrolysis of the intermediate vinyl ether (dil. HCl, 65-70% yield). ... 

Nickel peroxide is a solid, insoluble oxidant prepared by reaction of nickel (II) salts with hypochlorite or ozone in aqueous alkaline solution. This reagent when used in nonpolar medium is similar to, but more reactive than, activated manganese dioxide in selectively oxidizing allylic or acetylenic alcohols. It also reacts rapidly with amines, phenols, hydrazones and sulfides so that selective oxidation of allylic alcohols in the presence of these functionalities may not be possible. In basic media the oxidizing power of nickel peroxide is increased and saturated primary alcohols can be oxidized directly to carboxylic acids. In the presence of ammonia at —20°, primary allylic alcohols give amides while at elevated temperatures nitriles are formed. At elevated temperatures efficient cleavage of a-glycols, a-ketols... 

CFCs have been widely used as cleaning solvents, as they are nonflammable and their toxicity is low. Now, flammable solvents are coming back into favor. A news item from a manufacturer described "a new ozone-friendly cleaning process for the electronics industry, which "uses a unique hydrocarbon-alcohol formulation. It did not remind readers that the mixture is flammable and that they should check that their equipment and procedures are suitable. 

Compounds containing susceptible C—H bonds can be oxidized to alcohols. " Nearly always, the C—H bond involved is tertiary, so the product is a tertiary alcohol. This is partly because tertiary C—H bonds are more susceptible to free-radical attack than primary and secondary bonds and partly because the reagents involved would oxidize primary and secondary alcohols further. In the best method, the reagent is ozone and the substrate is absorbed on silica gel. Yields as high as 99% have been... 

TERTIARY ALCOHOLS FROM HYDROCARBONS BY OZONATION ON SILICA GEL 1-ADAMANTANOL... 

This dry ozonation procedure is a general method for hydrox-ylation of tertiary carbon atoms in saturated compounds (Table 1). The substitution reaction occurs with predominant retention of configuration. Thus cis-decalin gives the cis-l-decalol, whereas cis- and frans-l,4-dimethylcyclohexane afford cis- and trans-1,4-dimethylcyclohexanol, respectively. The amount of epimeric alcohol formed in these ozonation reactions is usually less than 1%. The tertiary alcohols may be further oxidized to diols by repeating the ozonation however, the yields in these reactions are poorer. For instance, 1-adamantanol is oxidized to 1,3-adamantane-diol in 43% yield. Secondary alcohols are converted to the corresponding ketone. This method has been employed for the hydroxylation of tertiary positions in saturated acetates and bromides. 

Tertiary Alcohols from Hydrocarbons by Ozonation on Siuca Gel ... 

Preparation of Tertiary Alcohols from Hydrocarbons with Ozone on Silica Ge... 

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