Ozonolysis of vinyl chloride in methanol: a convenient entry to methoxymethylhydroperoxide and its chemistry

Meister, Martin; Zwick, G.; Griesbaum, Karl

doi:10.1139/v83-413

Cited by 15 publications

(6 citation statements)

References 4 publications

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“…The above observations [22,24] suggest that CH,-0-CHO observed in this study is due to a heterogeneous reaction. Through the course of this study, it was observed that HCOOH, either formed as a product or added as a reactant, tended to adhere to the reactor wall.…”

Section: Formation Of Compound Z a N D Formic Acetic Anhydride With Tsupporting

confidence: 61%

“…Through the course of this study, it was observed that HCOOH, either formed as a product or added as a reactant, tended to adhere to the reactor wall. It is possible, therefore, that the adsorbed HCOOH acted as a proton donor in the CH, -0-CH,OOH conversion mechanism, as described by Meister et al [24].…”

Section: Formation Of Compound Z a N D Formic Acetic Anhydride With Tmentioning

confidence: 95%

“…Meister et al [24] found that CH,-0-CH,OOH, which was formed with high yield in the ozonolysis of vinyl chloride in CH,OH at 195 K, was readily converted to a mixture of 89% CH,-0-CHO and 11% CH,O(CH,), when treated -in a 1 : 10 mixture of anhydrous HCI in CH,OH at 313 K. Similar results were observed at ambient temperature, albeit at a considerably slower rate.…”

Section: Formation Of Compound Z a N D Formic Acetic Anhydride With Tmentioning

confidence: 99%

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Gas-phase ozonolysis of ethene in the presence of hydroxylic compounds

Neeb

Horie

Moortgat

1996

Int. J. Chem. Kinet.

125

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Ozonolysis of C2H4 was carried out at 295 K in 730 torr synthetic air in the concentration ranges of [O3]0 = 1.9–8.2 ppm and [C2H4]0 = 4.0–15.0 ppm, in the absence and presence of the added HCOOH (1 ppm), CH3COOH (1–10 ppm), and CH3OH (36–100 ppm). In the absence of the added compounds, a nearly complete analysis of the reaction products was achieved, with the yields expressed relative to the converted C2H4: HCHO 0.98, CO 0.26, CO2 0.18, HCOOH 0.05, and the sum of formic acid anhydride (FAN) and hydroperoxymethyl formate (HPMF), CHO(SINGLE BOND)O(SINGLE BOND)CH2OOH, 0.19. In the presence of the added HCOOH, the yield of [FAN + HPMF] increased. The addition of CH3COOH suppressed the formation of FAN and HPMF completely. The addition of large excesses of CH3OH also decreased the yield of [FAN + HPMF] significantly. In both cases, new products with the formula R(SINGLE BOND)O(SINGLE BOND)CH2OOH where R = CH3CO and CH3 for CH3COOH and CH3OH, respectively, were formed. The present results, together with the formation of hydroxymethyl hydroperoxide, HO(SINGLE BOND)CH2OOH, with added water vapor (Horie et al., Geophys. Res. Lett., 21, 1523, (1994)) were explained by the reaction of the Criegee biradical CH2OO with the added hydroxy compounds ROH. Formation of the products with the general formula R(SINGLE BOND)O(SINGLE BOND)CH2OOH indicates that the RO(SINGLE BOND)H bond fission has taken place. © 1996 John Wiley & Sons, Inc.

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Section: Formation Of Compound Z a N D Formic Acetic Anhydride With Tsupporting

confidence: 61%

Section: Formation Of Compound Z a N D Formic Acetic Anhydride With Tmentioning

confidence: 95%

Section: Formation Of Compound Z a N D Formic Acetic Anhydride With Tmentioning

confidence: 99%

See 1 more Smart Citation

Gas-phase ozonolysis of ethene in the presence of hydroxylic compounds

Neeb

Horie

Moortgat

1996

Int. J. Chem. Kinet.

125

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“…For accurate spectral measurements to be made, experiments must be performed under conditions where F atoms are converted stoichiometrically into CH30CH202 radicals by the reaction sequence (10) followed by (2): F + CH3OCH3 -CH3OCH2 + HF (10) CH3OCH2 + 02 (+M) -CH30CH202 (+M) (2) Several potentially interfering reactions may be identified, and their possible effect must be considered; F + Oz (+M) -F02 (+M) (14) F + CH3OCH2products (15)…”

Section: Self Reaction Kinetics and Uv Absorptionmentioning

confidence: 99%

Kinetic and mechanistic study of the self-reaction of methoxymethylperoxy radicals at room temperature

Jenkin¹,

Hayman²,

Wallington³

et al. 1993

J. Phys. Chem.

136

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The UV absorption spectrum and kinetics of the self reaction of CH3OCH202 at 298 K have been studied using both the modulated photolysis of C12/CHsOCH3/02/N2 mixtures and the pulse radiolysis of SFs/CH3OCHp/ 0 2 mixtures. The spectrum, characterized in the range 200-290 nm, is in good agreement with the single published determinatiom8 The observed second-order removal kinetics of CH30CH202, ks,a, were found to be sensitive to both the variation of total pressure (1 7-760 Torr) and the composition of the reaction mixtures:2CH3OCH202 -2CH3OCH20 + 0 2 (sa); -CH3OCHO + CH3OCH20H + 0 2 (5b). The kinetic studies and a detailed product investigation using long path length FTIR spectroscopy (T = 295 K, C12/CHoOCHs/ 0 2 / N 2 system) provide evidence to support a mechanism involving the rapid thermal decomposition of CH3-OCH2O by H atom ejection occurring in competition with thereaction with 0 2 : CHsOCHtO (+M) -CH30CHO + H (+M) (6); CH3OCH20 + 0 2 -CH30CHO + HO2 (4). The complications in the measured values of ksoh in the present studies, and those reported previously,8 are believed to occur as a direct result of formation of H atoms from reaction 6. Accordingly, a pressure-independent value of k5 = (2.1 f 0.3) X 1@l2 cm3 molecule-' s-I is derived for the elementary rate coefficient at 298 K, with identical values of the branching ratio a = ksa/ks = 0.7 f 0.1 determined independently from the FTIR product studies and the modulated photolysis experiments. As part of this work, the rate coefficient for the reaction of C1 atoms with CH3OCHzCl was found to be (2.9 f 0.2) X 10-l' cm3 molecule-l s-l.

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“…The salts were filtered off and the filtrate was concentrated at room temperature and 12 Tom; 'H nmr analysis (CDC13, TMS) of the liquid residue (2 mL) showed the presence of 21 and 22 (6 4.98, s, CHI) (14) in a ratio of 1:0.9. By flash chromatography (column 2 X 30 cm, 50 g silica gel, dichloromethane), 60 mg (31%) of 21 was isolated.…”

Section: Ozonolysis Of Z2b In Ch30dmentioning

confidence: 99%

Monoozonides of chloro-substituted conjugated dienes: preparation, stability, and some chemical reactions

Griesbaum¹,

Bandyopadhyay²,

Meister³

1986

Can. J. Chem.

Self Cite

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The chlorodienes (E)-4-chloro-3-methyl-1,3-hexadiene (5a), (E)- and (Z)-4-chloro-2,3-dimethyl-1,3-hexadiene (5b/6b), (E,E)-5-chloro-4-methyl-2,4-heptadiene (5c), (4E)- and (4Z)-5-chloro-3,4-dimethyl-2,4-heptadiene (5d/6d), chloroprene (11a), and 2-chloro-3-methyl-1,3-butadiene (11b) are selectively ozonized at the non-chlorinated double bonds to give the corresponding monoozonides 7, 8, and 12. Further ozonolyses of the monoozonides of 5b and of 11b in methanol as well as epoxidation of the monoozonide of 5b and subsequent reaction of the resulting chloroepoxide with AgBF4 are described.

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Ozonolysis of vinyl chloride in methanol: a convenient entry to methoxymethylhydroperoxide and its chemistry

Cited by 15 publications

References 4 publications

Gas-phase ozonolysis of ethene in the presence of hydroxylic compounds

Gas-phase ozonolysis of ethene in the presence of hydroxylic compounds

Kinetic and mechanistic study of the self-reaction of methoxymethylperoxy radicals at room temperature

Monoozonides of chloro-substituted conjugated dienes: preparation, stability, and some chemical reactions

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