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diazomethane synthesis 13 years 4 months ago #949

Hello.
How is diazomethane produced in the laboratory efficiently?
How is it produced at an industrial level?
I say this because in Arndt Eistert's synthesis it is used and this synthesis is seen to be widely used and very elegant. By the way, this reaction of the Arndt Eistert synthesis is easy to carry out in the laboratory.

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Re: synthesis of diazomethane 13 years 4 months ago #952

Well it seems that working with diazomethane is quite dangerous, here I got something on it.
In liquid or gaseous state, Diazomethane explodes with flame and the liquid can detonate even at -80°C.
However, these explosions do not occur when diazomethane is prepared and stored in solvents such as ethyl ether. Diazomethane toxicity has been attributed to the intracellular formation of formaldehyde.
Diazomethane slowly reacts with water to form methyl alcohol and release nitrogen. Formaldehyde, on the other hand, is formed by oxidation of methyl alcohol. Diazomethane has been shown to be a lung carcinogen in mice and rats.
Skin application and subcutaneous injection, as well as inhalation of this compound have also been shown to promote tumor development in experimental animals. Studies in bacteria have shown mutagenic effects. However, the International Agency for Research on Cancer (IARC) has placed it in Group 3, that is, it cannot be classified as a human carcinogen. Diazomethane is an effective insecticide for chemical control of Triatoma pests. It is also useful as an algaecide. When the ichthyotoxic component of the green algae Chaetomorpha minima is methylated with diazomethane, a solid is obtained that retains its lethal toxicity to fish. It is significant that in the metabolism of the carcinogens dimethylnitrosamine and circasin, one of the intermediate products is diazomethane.

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Re: synthesis of diazomethane 13 years 4 months ago #954

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Re: synthesis of diazomethane 13 years 4 months ago #955

Arndt-Eistert reaction
A very interesting compound intervenes in this reaction, diazomethane, a yellow gas with the formula CH2N2 , was discovered by Hans Baron Von Pechmann.
He discovered that diazomethane reacts with hydrochloric acid, giving off nitrogen and forming methyl chloride. Diazomethane also reacts with carboxylic acid providing an elegant method for preparing methyl esters. If an ethereal solution of diazomethane (yellow in color) is added little by little to a solution or suspension of the acid in ether, nitrogen evolution occurs, at the same time that the yellow color disappears; when the yellow color does not disappear when adding a new portion of the reagent, it indicates that the reaction is complete; the solution is then heated in a water bath, to eliminate the excess of reagent, thus having a colorless solution of the resulting ester. It should be noted as a curious fact that if you heat the diazoketone with water in the presence of colloidal silver as a catalyst, methylene will insert itself between the carbonyl carbon and the carbon next to it, giving this reaction by rearrangements.

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