Preparation method of acetoacetanilide compound

Abstract

The invention provides a preparation method of an acetoacetanilide compound. The method comprises the steps of performing diacetylation reaction on aniline compounds and diketene in an organic solvent under anaerobic conditions to obtain the acetoacetanilide compound. The acetoacetanilide compound is prepared under the anaerobic conditions; the acetoacetanilide compound prepared by using the method has a relatively high melting point, thereby being beneficial for applications of the acetoacetanilide compound. In addition, the acetoacetanilide compound prepared by using the method provided by the invention is not easy to agglomerate, and the preparation method of the acetoacetanilide compound, provided by the invention, is relatively low in energy consumption. Experimental results show that the melting point of the acetoacetanilide compound prepared by using the method provided by the invention is 82.5-103 DEG C.

Description

technical field

[0001] The invention relates to the technical field of compound preparation, in particular to a preparation method of acetoacetanilide compounds. Background technique

[0002] Acetoacetanilide is a white crystalline powder, slightly soluble in water and easily soluble in organic solvents such as ethanol, ether, and chloroform. Acetoacetanilide can be used as an intermediate for organic pigments, dyes, and pesticides, and can be used to manufacture pyrazolone, bright yellow 5G, acid complex yellow GR, neutral deep yellow GL, neutral orange RL, sweat sand yellow G, pigment resistant Tanhuang G and the pesticide wilting, etc.

[0003] Acetoacetanilide is generally prepared by reacting diketene and aniline. The specific method is to put 46g of anhydrous aniline and 125mL of anhydrous benzene in a 500mL three-necked flask; Add 42g of diketene benzene solution dropwise in the flask, the molar concentration of the diketene benzene solution is 0.006mol / mL; the mate...

Examples

preparation example Construction

[0020] The invention provides a kind of preparation method of acetoacetanilide compound, comprising:

[0021] Under oxygen-free conditions, aniline compounds and diketene are subjected to a diacetylation reaction in an organic solvent to obtain acetoacetanilide compounds.

[0022] The acetoacetanilide compound prepared by the method provided by the invention has a relatively high melting point, which is beneficial to the application of the acetoacetanilide compound. In addition, the acetoacetanilide compounds prepared by the method provided by the invention are not easy to agglomerate, and the preparation method of the acetoacetanilide compounds provided by the invention has low energy consumption.

[0023] In the present invention, the aniline compound and diketene are subjected to a diacetylation reaction in an organic solvent under an oxygen-free condition to obtain the acetoacetanilide compound. In the present invention, the aniline compound is preferably mixed with an or...

Embodiment 1

[0036] After replacing the air in the reactor with nitrogen, seal the reactor, add 2000L of ethanol and 400kg of 2,4-dimethylaniline to the reactor at 23°C and a stirring speed of 80 rpm After mixing, add 292kg of diketene to the obtained mixture within 1.5 hours for diacetylation reaction; heat the obtained reaction product at 40°C for 3 hours; cool the obtained heat-preserved product to 6°C, filter and dry , to obtain acetoacetyl 2,4-xylaniline.

[0037] The appearance, melting point, product content and agglomeration time of the acetoacetyl 2,4-xylaniline obtained in Example 1 of the present invention were tested according to the method described in the above technical scheme. The test results are shown in Table 1, which is the embodiment of the present invention. The test results of the appearance, melting point, product content and caking time of the acetoacetanilide compounds obtained in Examples and Comparative Examples.

[0038] Test the yield of the acetoacetyl 2,4-x...

Embodiment 2

[0040] After replacing the air in the reactor with nitrogen, seal the reactor, add 2000 L of ethanol and 400 kg of aniline to the reactor at 23° C. and a stirring speed of 80 rpm, and mix them within 1.5 hours. 380 kg of diketene was added to the obtained mixture to carry out diacetylation reaction; the obtained reaction product was subjected to heat preservation treatment at 40° C. for 3 hours; the obtained heat preservation treatment product was cooled to 6° C., filtered and dried to obtain acetoacetanilide.

[0041] The appearance, melting point, product content and caking time of the acetoacetanilide obtained in Example 2 of the present invention were tested according to the method described in the above technical solution, and the test results are shown in Table 1.

[0042] The yield of the method for preparing acetoacetanilide provided in Example 2 of the present invention was tested according to the method described in the above technical solution, and the test result sh...

technical field

[0001] The invention relates to the technical field of compound preparation, in particular to a preparation method of acetoacetanilide compounds. Background technique

[0002] Acetoacetanilide is a white crystalline powder, slightly soluble in water and easily soluble in organic solvents such as ethanol, ether, and chloroform. Acetoacetanilide can be used as an intermediate for organic pigments, dyes, and pesticides, and can be used to manufacture pyrazolone, bright yellow 5G, acid complex yellow GR, neutral deep yellow GL, neutral orange RL, sweat sand yellow G, pigment resistant Tanhuang G and the pesticide wilting, etc.

[0003] Acetoacetanilide is generally prepared by reacting diketene and aniline. The specific method is to put 46g of anhydrous aniline and 125mL of anhydrous benzene in a 500mL three-necked flask; Add 42g of diketene benzene solution dropwise in the flask, the molar concentration of the diketene benzene solution is 0.006mol / mL; the mate...

Examples

preparation example Construction

[0020] The invention provides a kind of preparation method of acetoacetanilide compound, comprising:

[0021] Under oxygen-free conditions, aniline compounds and diketene are subjected to a diacetylation reaction in an organic solvent to obtain acetoacetanilide compounds.

[0022] The acetoacetanilide compound prepared by the method provided by the invention has a relatively high melting point, which is beneficial to the application of the acetoacetanilide compound. In addition, the acetoacetanilide compounds prepared by the method provided by the invention are not easy to agglomerate, and the preparation method of the acetoacetanilide compounds provided by the invention has low energy consumption.

[0023] In the present invention, the aniline compound and diketene are subjected to a diacetylation reaction in an organic solvent under an oxygen-free condition to obtain the acetoacetanilide compound. In the present invention, the aniline compound is preferably mixed with an or...

Embodiment 1

[0036] After replacing the air in the reactor with nitrogen, seal the reactor, add 2000L of ethanol and 400kg of 2,4-dimethylaniline to the reactor at 23°C and a stirring speed of 80 rpm After mixing, add 292kg of diketene to the obtained mixture within 1.5 hours for diacetylation reaction; heat the obtained reaction product at 40°C for 3 hours; cool the obtained heat-preserved product to 6°C, filter and dry , to obtain acetoacetyl 2,4-xylaniline.

[0037] The appearance, melting point, product content and agglomeration time of the acetoacetyl 2,4-xylaniline obtained in Example 1 of the present invention were tested according to the method described in the above technical scheme. The test results are shown in Table 1, which is the embodiment of the present invention. The test results of the appearance, melting point, product content and caking time of the acetoacetanilide compounds obtained in Examples and Comparative Examples.

[0038] Test the yield of the acetoacetyl 2,4-x...

Embodiment 2

[0040] After replacing the air in the reactor with nitrogen, seal the reactor, add 2000 L of ethanol and 400 kg of aniline to the reactor at 23° C. and a stirring speed of 80 rpm, and mix them within 1.5 hours. 380 kg of diketene was added to the obtained mixture to carry out diacetylation reaction; the obtained reaction product was subjected to heat preservation treatment at 40° C. for 3 hours; the obtained heat preservation treatment product was cooled to 6° C., filtered and dried to obtain acetoacetanilide.

[0041] The appearance, melting point, product content and caking time of the acetoacetanilide obtained in Example 2 of the present invention were tested according to the method described in the above technical solution, and the test results are shown in Table 1.

[0042] The yield of the method for preparing acetoacetanilide provided in Example 2 of the present invention was tested according to the method described in the above technical solution, and the test result sh...

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