The Tetrahydrophphalic Acids

Buckles, Robert E.

doi:10.1021/cr50016a003

Cited by 8 publications

(3 citation statements)

References 43 publications

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“…(7) Moelwyn-Hughes, E.A., "Physical Chemistry," p. 56, Pergamon Press, New York, 1957. ) are readily available commercial materials finding use as alkyd, polyester, and epoxy resin intermediates (2,3,16). The former is prepared by hydrogenating the latter (13), which is made by adding maleic anhydride to butadiene (4,6).…”

Section: Acknowledgmentmentioning

confidence: 99%

“…where d is the partition coefficient (concentration of iodomethane in liquid per concentration of iodomethane in gas phase), D is the diffusivity of iodomethane in the liquid (square centimeters per second), and the other quantities have already been defined. 103-4" C.) are readily Although many miscellaneous half amides and imides available commercial materials finding use as alkyd, poly-have been prepared from these anhydrides, only the N-alkyl ester, and epoxy resin intermediates (2,3, 16). for very dilute solutions of iodomethane.…”

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“…103-4" C.) are readily Although many miscellaneous half amides and imides available commercial materials finding use as alkyd, poly-have been prepared from these anhydrides, only the N-alkyl ester, and epoxy resin intermediates (2,3, 16). ; b.p.…”

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Half amides and imides of cis-cyclohexane-1,2-dicarboxylic acid and cis-4-cyclohexene-1,2-dicarboxylic acid

Godt¹,

Anzenberger²,

Freerks³

1968

J. Chem. Eng. Data

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A obsd which by rearranging and squaring results in Equation 11.) where d is the partition coefficient (concentration of iodomethane in liquid per concentration of iodomethane in gas phase), D is the diffusivity of iodomethane in the liquid (square centimeters per second), and the other quantities have already been defined. The partition coefficient of iodomethane between water and air has been determined in this laboratory to be 1.5 a t 50°C. for very dilute solutions of iodomethane. The diffusivity of iodomethane was assumed to be 2.5 x lo-' sq. cm. per second, which is of a correct order-of-magnitude value when compared with the diffusivity of various haloalkanes ( 5 ) .The liquid reaction rate constant which is calculated from the data in Table I1 is proportional to the square of the mole fraction of hydrazine hydrate in the solution (Equation 11 and Figure 2) for the concentration range which was studied. The calculated liquid reaction rate for a 5.1-mole per liter solution-Le., 0.11 mole fraction-is 0.34 second-' which corresponds to a second order rate constant of 0.07 liter moleThe liquid reaction rate constant is estimated to be ca. 0.3 liter mole-' second-' which is a factor of four faster than that calculated by use of Equation 11. (The liquid reaction rate constant has been determined directly in this laboratory to be 0.02 liter mole-' second-' a t 21°C. for 0.03 to 0.1M hydrazine solutions which are 0.05M in sodium hydroxide. With the assumption of an activation energy of 18 kcal. per mole, the reaction rate constant a t 50°C. is calculated to be 0.3 liter mole-' second-'.) The experimental dependence of hl calculated by Equation 11 on the square of the mole fraction of hydrazine hydrate is quite unexpected and is difficult to rationalize with respect to the second order kinetics which were found for dilute (ca. 0.1M) hydrazine solutions. The application of Equation 10 to prediction of rates of iodomethane removal appears to be more reliable than the predicted rate from the diffusion-reaction model.Treatment of the data in Table I11 according to the Arrhenius relationship yields an energy of activation of between 5 and 6 kcal. per mole. The energy of activation second-'. appears to increase as the temperature is increased. Winning (1 1 ), in studying the heterogeneous reaction of hydrazine and oxygen, found an energy of activation of 6.4 kcal. per mole which increased as the temperature was increased. Winning suggested that this effect, the increase in energy of activation, was due to the increasing importance of the gas phase reaction. Bowen has reported the energy of activation of the gas phase reaction of hydrazine and oxygen to be 38 kcal. per mole ( 2 ) . This reasoning could be applied to the reaction between hydrazine and iodomethane, and the rate of the gas phase reaction would be predicted to become an increasingly important term as the temperature is increased. (If 5 and 38 kcal. per mole are assumed to be the energy of activation of the first and second terms, and if a t 50"C., the cont...

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Section: Acknowledgmentmentioning

confidence: 99%

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Half amides and imides of cis-cyclohexane-1,2-dicarboxylic acid and cis-4-cyclohexene-1,2-dicarboxylic acid

Godt¹,

Anzenberger²,

Freerks³

1968

J. Chem. Eng. Data

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Investigations on pyrazine derivatives. V. A more detailed investigation on the catalytic hydrogenation of esters of pyrazine carboxylic acids

Mager

Berends

1959

Recl. Trav. Chim. Pays‐Bas

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In the first publication in this series it was shown that only partial reduction of the pyrazine ring occurs in the catalytic hydrogenation of tetra‐carbethoxypyrazine. The remaining double bonds in the resultant reaction product are apparently stabilised. In agreement with the hypotheses put forward to explain this result, esters of other pyrazine carboxylic acids also are only partially reducible with palladium on carbon at room temperatures. The conclusion must be drawn that a carbalkoxy group attached to a pyrazine ring protects an adjacent double bond in the ring against catalytic hydrogenation. The partially hydrogenated products from the esters of some pyrazine carboxylic acids are extraordinarily labile. Dehydrogenation by dismutation or reoxidation, which occurs to some extent, can be followed from the spectra. Similar phenomena have been encountered in the pyridine series, which may be put forward as supporting the conclusions reached.

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The synthesis and properties of dialkyl epoxyhexahydrophthalates

Baiburova

Malyshko

et al. 1962

Petroleum Chemistry U.S.S.R.

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The Tetrahydrophphalic Acids

Cited by 8 publications

References 43 publications

Half amides and imides of cis-cyclohexane-1,2-dicarboxylic acid and cis-4-cyclohexene-1,2-dicarboxylic acid

Half amides and imides of cis-cyclohexane-1,2-dicarboxylic acid and cis-4-cyclohexene-1,2-dicarboxylic acid

Investigations on pyrazine derivatives. V. A more detailed investigation on the catalytic hydrogenation of esters of pyrazine carboxylic acids

The synthesis and properties of dialkyl epoxyhexahydrophthalates

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