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Acetoacetanilide: Aniline in Ether with Diketene Added Slowly (Gleason, Standard Oil Development, US 2,174,239)
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31. uMfumfu 2026DE
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Acetoacetanilide: Aniline in Ether with Diketene Added Slowly (Gleason, Standard Oil Development, US 2,174,239)

Diketene and aniline join into acetoacetanilide, the coupling component of Hansa yellow, but neat they react so violently that the product is poor. Gleason tamed the reaction by diluting both in ether and adding the diketene slowly; the anilide simply crystallises out. Result: crystals of acetoacetanilide. Source: Gleason, US 2,174,239 (Standard Oil Development, 1939). Not given: yield. Picture drawn by Youblob.
Ophakathi
1 day

Imiyalelo

1

Dissolve the aniline

Dissolve 1 part by weight of aniline in about 5 parts of ether at room temperature.

Izinto zokwakha zalesi sinyathelo:

I-anilineI-aniline1 part by weight

Amathuluzi adingekayo:

I-diethyl etherI-diethyl ether
Ibhodlela elinesisekelo esiyindilingaIbhodlela elinesisekelo esiyindilinga
Isikali sesilinganisoIsikali sesilinganiso
2

Add diketene slowly

Add 1 part of diketene slowly with stirring. Keep it at room temperature or a little above, never even locally above 80-100 C; cool if needed.

Izinto zokwakha zalesi sinyathelo:

I-ketene dimerI-ketene dimer1 part by weight

Amathuluzi adingekayo:

Ifasitela lokwehlukanisaIfasitela lokwehlukanisa
IthemomithaIthemomitha
3

Let it crystallise

When the reaction is over, let the liquid stand; acetoacetanilide crystallises.

Amathuluzi adingekayo:

Ibhodlela elinesisekelo esiyindilingaIbhodlela elinesisekelo esiyindilinga
4

Collect and wash

Decant or filter off the crystals and wash them with a little cold ether.

Amathuluzi adingekayo:

I-funnel ye-Büchner (i-porcelain)I-funnel ye-Büchner (i-porcelain)
Iphepha LokuhluzaIphepha Lokuhluza
I-diethyl etherI-diethyl ether

Izinto

2
  • 1
    I-aniline
    1 part by weight
    Isibambeli
  • 2
    I-ketene dimer
    1 part by weight
    Isibambeli

Amathuluzi Adingekayo

7

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I-acetoacetanilide

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Diketene: Acetone Pyrolysed in Copper at 650 C, Ketene Caught Cold in Acetone and Left to Dimerise (Law, Carbide, US 2,019,983)
Yingozi

Diketene: Acetone Pyrolysed in Copper at 650 C, Ketene Caught Cold in Acetone and Left to Dimerise (Law, Carbide, US 2,019,983)

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