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Acetoacetanilide: Aniline in Ether with Diketene Added Slowly (Gleason, Standard Oil Development, US 2,174,239)
Charlie

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Charlie

31. Ukwakira 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.
Hagati
1 day

Amabwiriza

1

Dissolve the aniline

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

Ibikoresho by'iyi ntambwe:

AniliniAnilini1 part by weight

Ibikoresho bikenewe:

Dietili etereDietili etere
Icupa rifite igituza kizengurutseIcupa rifite igituza kizengurutse
Umunzani w'ibiroUmunzani w'ibiro
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.

Ibikoresho by'iyi ntambwe:

Dimeri ya keteneDimeri ya ketene1 part by weight

Ibikoresho bikenewe:

Igifuniko gitandukanyaIgifuniko gitandukanya
Igipima UbushyuheIgipima Ubushyuhe
3

Let it crystallise

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

Ibikoresho bikenewe:

Icupa rifite igituza kizengurutseIcupa rifite igituza kizengurutse
4

Collect and wash

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

Ibikoresho bikenewe:

Ifonelo ya Büchner (ya porcelaine)Ifonelo ya Büchner (ya porcelaine)
Urupapuro rwo KuyungururaUrupapuro rwo Kuyungurura
Dietili etereDietili etere

Ibikoresho

2
  • 1
    Anilini
    1 part by weight
    Umwanya
  • 2
    Dimeri ya ketene
    1 part by weight
    Umwanya

Ibikoresho bikenewe

7

Iki gishushanyo gikora

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Agateganyo

Asetoasetanilide

Free

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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)
Akaga

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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