The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry


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In accordance with the invention, ketene is condensed with dry hydrocyanic acid, at temperatures between about C. The use of the higher temperatures, for example those around 10 C. The condensation reaction preferably is conducted in the presence of an anhydrous volatile organic solvent or diluent for the reactants and the catalyst. A suitable solvent desirably is one that is inert to the reactants and to the catalyst;. Among solvents advantageously employed in the process may be mentioned organic acid anhydrides such as acetic anhydride; the aliphatic others, such as diethyl ether and dioxane; esters of carboxylic acids such as methyl acetate, ethylacetate and l-cyanovinyl acetate;.

The use of acetic anhydride alone as a solvent or diluent in the reaction mixture is particularly advantageous and tends to provide almost quantitative yields of the l-cyanovinyl acetate. Similarly, an excess of hydrocyanic acid may be employed, in which case the excess acid functions as a volatile solvent or diluent. The condensation reaction between the ketene and hydrocyanic acid may be effected by slowly introducing a stream of ketene vapors into an agitated body of anhydrous hydrocyanic acid which contains the catalyst, and which preferably is in solution in a volatile solvent for the reactants and catalysts.

After the absorption of the requisite amount of ketene, the reaction mixture may be fractionally distilled under subatmospheric pressure in a suitable column still.

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The ketene and hydrocyanic acid may very advantageously be introduced concurrently, preferably in a ratio of between 2 and 3 mols of the former to one mol of the latter, into a solution of the catalyst in a volatile solvent for the reactants. The resultant reaction mixture, after absorption of the required amount of ketene, is fractionally distilled under vacuum in the manner previously indicated for the isolation and recovery of the decyanic acid and solvent. By neutralizing the condensation reaction mix- Example 1 One hundred and seventy eight grams of ketene were slowly introduced into 81 grams of anhydrous hydrocyanic acid containing 3 cc.

After absorption of the ketene was completed, the reaction mixture was fractionally distilled under vacuum through a short column. Example 2 Following the general procedure described in Example 1, grams of ketene were introduced into a mixture of 81 grams of anhydrous hydrocyanic acid, 3 cc. Example 3 During a 4. The reaction mixture and basic catalyst were then neutralized by adding thereto one gram of glacial acetic acid. Example 4 Example 5 Ketene and anhydrous hydrocyanic acid were are based I I concurrently introduced slowly over a.

From grams of ketene and From grams'oi ketene and 81 grams of hydrocyanic acid introduced over a periodoi flve hours, there were secured,. Under similar operating conditions but using 3 cc..

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Upon fractional distillation under vacuum 01 the reaction mixture thus obtained from grams of ketene and 81 grams of hydrocyanic acid, grams 40 01 l-cyanovinyl acetate were recovered, establishing that grams thereof had been produced in the process. Seven grams of unreacted hydrocyanic acid were recovered.

Under generally similar operating conditions but using 1 cc. The reaction mixture was fractionated in the manner indicated inv Example 1. From grams of ketene and 54 grams of hydrocyanic acid there but using sodium phenate as the catalyst, similar results are obtained. During a period of 1. During 2. N,2-cyanoethyl morphoiine maintained at approximately 45 0. Example 13 During a period of one grams oi ketene and 54 grams of dry'hydrocyanic acid were added to a mixture'oi cc. Under substantially the same conditions described-in Example 9, but substituting 3 grams of potassium naphthalene for the one gram of sodiacetate was secured.

The results of extensive experimental work hasestablished that neither l-"cyanovinyl acetate nor dimolecular acetyl cyanide can be produced by'reacting ketene and hydrccyanic acid in the;. Incr a in slowly added over 1. Compare the catalyzed reaction of Example. The l-cyanovinyl acetate produced by this invention -is a water-white, mobile liquid with a sharp'odor. It boilsbetween C. The dimolecular acetyl cyanideis a white, I crystalline solid melting at 70 C.

Process which comprises introducing successive portions of ketene into a liquid body maintained at a temperature within the range between about C.

The dimo ecular acetyl cyanide has apparent value in the rently introducing successive portions of ketene and dry hydrocyanic acid in the ratio of between 2 and 3 mols of the ketene per mol of the said acid into a solution of a basic alkali metal compound in an anhydrous volatile solvent for the ketene and hydrocyanic acid; which basic compound does not substantially reactwith ketene I to form non-basic reaction products under the conditions of the resultant reaction between the ketene and hydrocyanic acid, said solution being maintained at a temperature within the range between about '50 C.

Process which comprisesintroducing successive portions of ketene into-a liquid body containing dry hydrocyanic acid, a quaternary ammonium base, and an anhydrous volatile solvent for the reactants, and maintained at a temperature between around C.

Process which comprises introducing successive. Process which comprises slowlyv and concurrently introducing successive portions of ketene and dry hydrocyanic acid into a solution in an anhydrous volatile solvent for the ketene and hydrocyanic acid of a basic catalyst for the resultant condensation between the ketene and hydrocyanic acid, which catalyst does not substantially react with ketene to form non-basic reaction products under the conditions of the said condensation reaction, while maintaining said tion mixture at least one of the resultant reac-- tion products selected from the group consisting of l-cyanovinyl acetate and dimolecular acetyl cyanide.

The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry
The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry
The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry
The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry
The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry
The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry

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