BE434697A - - Google Patents
Info
- Publication number
- BE434697A BE434697A BE434697DA BE434697A BE 434697 A BE434697 A BE 434697A BE 434697D A BE434697D A BE 434697DA BE 434697 A BE434697 A BE 434697A
- Authority
- BE
- Belgium
- Prior art keywords
- diphenylene oxide
- dioxydiphenyl
- caustic potash
- water
- compound
- Prior art date
Links
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 25
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 12
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 230000009466 transformation Effects 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- GZSUIHUAFPHZSU-UHFFFAOYSA-N 9-ethyl-2,3-dihydro-1h-carbazol-4-one Chemical compound C12=CC=CC=C2N(CC)C2=C1C(=O)CCC2 GZSUIHUAFPHZSU-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
" Procédé d'obtention de o,o'-dioxydiphényle à partir d'oxy- de de diphénylène ".
Dans des passages anciens de la littérature (Krmer und Weissgerber, Ber. 34,1665 (1901), on trouve l'indication qu'il est possible de transformer en biphénol l'oxyde de diphénylène, par fusion avec de la potasse caustique. foute- fois, cette indication a été contredite ultérieurement sur la base de travaux plus récents, en partie par le même au- teur, et contrairement à cela, on a établi qu'il n'est pas possible de décomposer l'oxyde de diphénylène, par traitement avec de la potasse caustique, même pas, comme on l'avait proposé antérieurement, en réalisant la fusion à la potasse en présence de phénanthrène (Bothe, Diss, Gttingen,1908; Weissgerber und Seidler, Ber. 60, 2090 (1927)).
On a trouvé, conformément à la présente invention, que l'on réussit dtemblée et avec un rendement satisfaisant, à effectuer la décomposition de l'oxyde diphénylène au moyen de potasse caustique lorsque l'on opère en présence de com-
<Desc/Clms Page number 2>
posés cycliques qui renferment de l'hydrogène actif, lié au carbone ou à l'azote, et qui peut être remplacé par un mé- tal, par exemple du potassium. Ainsi que cela est connu, ces composés sont, par exemple, le cyclopentadiène, l'indène,le fluorène, le pyrrol, l'indol et le carbazol. En ohauffant avec de la potasse caustique, ces matières donnent,avec sépa- ration d'eau, le composé de potassium correspondant; on doit admettre que ce composé permet l'action de l'alcali sur lloxyde de diphénylène.
Une fois la transformation effectuée, on peut, par simple traitement au moyen d'eau, récupérer du composé alcalin, pratiquement sans perte, la substance intermédiaire et l'utiliser pour d'autres transformations .
Exemple 1
On chauffe pendant une heure 3/4 à 250-270 , 200 gr. d'oxyde de diphénylène, avec 20 gr. de oarbazol et 200 gr. de potasse caustique . On utilise une chaudière en cuivre munie d'un agitateur, avec réfrigérant à reflux qui laisse s'échapper la vapeur d'eau formée mais condense autant que possible l'oxyde de diphénylène vaporisé. On peut récupérer facilement l'oxyde de diphénylène se dégageant du réfrigé- rant. Une fois la réaction terminée, on broie la matière fondue et on la dissout dans l'eau, le earbazol restant sous forme de boue. Par acidification de la solution alcaline et recristallisation du précipité è partir de benzol, on ob- tient facilement 145 gr. d'o,o'-dioxydiphényle pur.- Exemple 2.
On chauffe pendant deux heures, à environ 275 , 10 kg d'oxyde de diphénylène avec 2,5 kg. de fluorène et 10 kg de potasse caustique . On traite par de l'eau et du benzol la masse fondue, broyée. L'eau dissout le composé de dioxy- diphényle et de potassium et décompose celui de fluorène et de potassium. Le fluorène libéré et l'oxyde de diphénylè- ne non modifié sont absorbés par le benzol ; traite la solution aqueuse comme dans l'exemple 1 et l'on obtient 7,2 kg de o,o'-dioxydiphênyle pur.
-2-
<Desc/Clms Page number 3>
Exemple 3.
On chauffe pendant trois heures, à 250 , 200 gr. d'oxy- de de diphénylène et 20 gr. d'indol avec 200 gr. de potasse caustique . Comme dans l'exemple 2, on obtient 115 gr. de o,o'-dioxydiphényle pur.
Le o,o'-dioxydiphényle est un fort désinfectant. De plus, on peut l'utiliser comme matière première dans un certain nombre de fabrications chimiques.
<Desc / Clms Page number 1>
"Process for obtaining o, o'-dioxydiphenyl from diphenylene oxide".
In old passages of the literature (Krmer und Weissgerber, Ber. 34,1665 (1901), we find the indication that it is possible to transform diphenylene oxide into biphenol, by fusion with caustic potash. - times, this indication was subsequently contradicted on the basis of more recent work, in part by the same author, and contrary to that, it was established that it is not possible to decompose diphenylene oxide, by treatment with caustic potash, not even, as had previously been proposed, by performing the potash smelting in the presence of phenanthrene (Bothe, Diss, Gttingen, 1908; Weissgerber und Seidler, Ber. 60, 2090 (1927 )).
It has been found, in accordance with the present invention, that it is immediately successful and with a satisfactory yield, to effect the decomposition of diphenylene oxide by means of caustic potassium hydroxide when the operation is carried out in the presence of compound.
<Desc / Clms Page number 2>
cyclic layers which contain active hydrogen, bound to carbon or nitrogen, and which can be replaced by a metal, for example potassium. As is known, these compounds are, for example, cyclopentadiene, indene, fluorene, pyrrol, indol and carbazol. On heating with caustic potash, these substances give, with separation of water, the corresponding potassium compound; it must be admitted that this compound allows the action of the alkali on the diphenylene oxide.
Once the transformation has been carried out, it is possible, by simple treatment with water, to recover the alkaline compound, practically without loss, the intermediate substance and to use it for other transformations.
Example 1
Heated for a 3/4 hour at 250-270, 200 gr. of diphenylene oxide, with 20 gr. of oarbazol and 200 gr. of caustic potash. A copper boiler equipped with a stirrer is used with a reflux condenser which allows the water vapor formed to escape but condenses as much as possible the vaporized diphenylene oxide. The diphenylene oxide evolving from the refrigerant can be easily recovered. When the reaction is complete, the molten material is crushed and dissolved in water, the earbazol remaining as a slurry. By acidification of the alkaline solution and recrystallization of the precipitate from benzol, 145 g are readily obtained. pure o, o'-dioxydiphenyl. Example 2.
Heated for two hours, to about 275, 10 kg of diphenylene oxide with 2.5 kg. of fluorene and 10 kg of caustic potash. The molten, ground mass is treated with water and benzol. Water dissolves the compound of dioxydiphenyl and potassium and decomposes that of fluorene and potassium. The liberated fluorene and the unmodified diphenylene oxide are absorbed by the benzol; the aqueous solution is treated as in Example 1 and 7.2 kg of pure o, o'-dioxydiphenyl are obtained.
-2-
<Desc / Clms Page number 3>
Example 3.
Heated for three hours at 250, 200 g. of diphenylene oxide and 20 gr. of indol with 200 gr. of caustic potash. As in Example 2, 115 g are obtained. of pure o, o'-dioxydiphenyl.
O, o'-dioxydiphenyl is a strong disinfectant. In addition, it can be used as a raw material in a number of chemical manufactures.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE434697A true BE434697A (en) |
Family
ID=93781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE434697D BE434697A (en) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE434697A (en) |
-
0
- BE BE434697D patent/BE434697A/fr unknown
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