BE558574A - - Google Patents
Info
- Publication number
- BE558574A BE558574A BE558574DA BE558574A BE 558574 A BE558574 A BE 558574A BE 558574D A BE558574D A BE 558574DA BE 558574 A BE558574 A BE 558574A
- Authority
- BE
- Belgium
- Prior art keywords
- nitro
- furfural
- diacetate
- semicarbazide
- reaction
- Prior art date
Links
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 3
- IAIWVQXQOWNYOU-UHFFFAOYSA-N nitrofurazone Chemical compound NC(=O)NN=CC1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000007659 semicarbazones Chemical class 0.000 description 3
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/70—Nitro radicals
- C07D307/71—Nitro radicals attached in position 5
- C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
- C07D307/74—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals
- C07D307/76—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals having carbonic acyl radicals or their thio or nitrogen analogues directly attached to the hydrazino or hydrazono radical, e.g. semicarbazides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Il est connu de préparer des semicarbazones par addition à un aldéhyde de chlorhydrate de semicarbazide en solutions tamponnées. Cette réaction générale exige la présence de l'aldéhyde à l'état pur. Comme on pouvait s'y attendre, cette réaction générale peut aussi être appli- quée à la préparation de la semicarbazone du nitro-5 furfural-2, pour laquelle on a donc besoin de nitro-5 furaldéhyde-2 à l'état pur.
Par la demande de brevet néerlandais n 138.175 publiée le 15 avril 1954, il est.connu de préparer de la semicarbazone du nitro-5 furfural-2 au départ de diacétate de nitro-5 furfural-2 et de chlorhydrate de semicarbazide par réaction directe de ces deux matières dans une solu- tion aqueuse d'un acide minéral fort à u n pH inférieur à 4,5 et par apport de chaleur jusqu'à ce que la réaction soit amorcée.
Lors de l'exécution de ce procédé, on doit par- tir de diacétate de nitro-5-furfural-2 pur, car sinon le produit finalement obtenu est de teinte brune. Par ail- leurs, on obtient le produit .désiré sous forme de cristaux relativement grands,, alors qu'il est précisément souhaita- ble de préparer de petits cristaux, parce que ceux-ci se mélangent de manière beaucoup plus homogène aux aliments pour le bétail, ceci constituant une des applications les plus importantes du composé en question.
Un autre inconvénient du procédé en question réside dans le fait que celui-ci doit être exécuté dans des récipients en émail ou en verre, c'est-à-dire dans des appareils coûteux ou fragiles.
<Desc/Clms Page number 2>
La présente invention résoud ces problèmes et permet d'obtenir le composé sous forme de cristaux très fins. Toute la réaction peut s'exécuter, sans aucun in- convénient, dans des appareils en acier inoxydable.
Le procédé suivant l'invention se caractérise par le fait que le diacétate de nitro-5 furfural-2 est hydrolysé et par le fait qu'on ajoute de la semicarbazide sans séparation de l'aldéhyde formée.
L'exemple d'exécution suivant illustrera l'in- vention.
On mélange 243 gr de diacétate de nitro-5 fur- fural-2, 200 cc de méthanol, 500 cc d'eau et 100 cc d'aci- de sulfurique concentré commercial et on fait bouillir sous reflux pendant 20 minutes. Après cela, on laisse refroidir le mélange réactionnel et on y ajoute une solu- tion de 76 gr de semicarbazide (sous forme de base) dans 250 cc d'eau. Il se forme un fin précipité de semicarba- zone du nitro-5 furfural-2, qui pèse 192 gr aprèéchage.
Rendement : 97 % de la théorie. Point de fusion : 224 - 226 C (avec décomposition).
<Desc / Clms Page number 1>
It is known to prepare semicarbazones by addition to an aldehyde of semicarbazide hydrochloride in buffered solutions. This general reaction requires the presence of the aldehyde in its pure state. As might be expected, this general reaction can also be applied to the preparation of the semicarbazone of 5-nitro-furfural-2, for which therefore pure 5-nitro-furaldehyde-2 is needed.
From Dutch patent application No. 138,175 published April 15, 1954, it is known to prepare 5-nitro-furfural-2 semicarbazone starting from 5-nitro-furfural-2 diacetate and semicarbazide hydrochloride by direct reaction of these two materials in an aqueous solution of a strong mineral acid at a pH below 4.5 and adding heat until the reaction is initiated.
In carrying out this process, one must start with pure 5-nitro-furfural-2 diacetate, otherwise the product finally obtained is brown in color. On the other hand, the desired product is obtained in the form of relatively large crystals, whereas it is precisely desirable to prepare small crystals, because these mix much more homogeneously with the food for the preparation. cattle, this being one of the most important applications of the compound in question.
Another drawback of the method in question lies in the fact that it must be carried out in enamel or glass containers, that is to say in expensive or fragile devices.
<Desc / Clms Page number 2>
The present invention solves these problems and enables the compound to be obtained in the form of very fine crystals. The entire reaction can be carried out without any inconvenience in stainless steel apparatus.
The process according to the invention is characterized in that the 5-nitro-furfural-2 diacetate is hydrolyzed and in the fact that semicarbazide is added without separation of the aldehyde formed.
The following execution example will illustrate the invention.
243 g of nitro-5-furfural-2 diacetate, 200 cc of methanol, 500 cc of water and 100 cc of concentrated commercial sulfuric acid are mixed and boiled under reflux for 20 minutes. After that, the reaction mixture is allowed to cool and a solution of 76 g of semicarbazide (as base) in 250 cc of water is added thereto. A fine precipitate of a semicarba- zone of 5-nitro-furfural-2 forms, which weighs 192 g after drying.
Yield: 97% of theory. Melting point: 224 - 226 C (with decomposition).
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE558574A true BE558574A (en) |
Family
ID=181588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE558574D BE558574A (en) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE558574A (en) |
-
0
- BE BE558574D patent/BE558574A/fr unknown
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