Acetaldehyde is shown to undergo a reversible Brønsted acid-catalyzed cyclotrimerization reaction, with 100%
selectivity, at ambient temperature within the zeolite host material ferrierite. It is shown by in situ solid-state
13C NMR spectroscopy and other techniques that the cyclic trimer is the only product formed in this reaction.
The equilibrium proportions of acetaldehyde and the cyclic trimer at ambient temperature correspond to a
conversion greater than 90%. In contrast, in the corresponding acid-catalyzed transformation of acetaldehyde
in the liquid state, a broad distribution of products is obtained. The reversibility of the cyclotrimerization
reaction in ferrierite is confirmed from the fact that, on adsorption of a pure sample of the cyclic trimer
within ferrierite, a reaction occurs to produce acetaldehyde as the only product with the same equilibrium
distribution of the cyclic trimer and acetaldehyde as that obtained from the reaction of acetaldehyde in ferrierite.
The role of Brønsted acid catalysis in the transformation between acetaldehyde and the cyclic trimer in ferrierite
is confirmed from the fact that no reaction occurs on adsorption of acetaldehyde within sodium-exchanged
ferrierite.
Nitrobenzene is a pale yellow to yellowish brown liquid with a boiling point of 207–212°C, depending on its purity. It is a very toxic substance with a maximum allowable concentration (PEL) of 1 ppm. The commercial production of nitrobenzene involves the direct nitration of benzene using a mixture of nitric and sulfuric acids, with typical yields of 96–99%. The main derivatives of nitrobenzene are
ortho
‐,
meta
‐, and
para
‐nitrochlorobenzene. These are toxic, with a PEL of 0.1 ppm for
p
‐nitrochlorobenzene.
Nitrotoluene exists as three isomers:
o
‐,
m
‐, and
p
‐nitrotoluene. The
o
‐ and
m
‐nitrotoluenes are clear yellow liquids at 25°C, whereas
p
‐nitrotoluene is a crystalline solid (mp 53.5°C). The nitrotoluenes are fairly toxic, with a PEL of 2 ppm.
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