AT28076B - Process for the preparation of formaldehyde sulfoxylates. - Google Patents
Process for the preparation of formaldehyde sulfoxylates.Info
- Publication number
- AT28076B AT28076B AT28076DA AT28076B AT 28076 B AT28076 B AT 28076B AT 28076D A AT28076D A AT 28076DA AT 28076 B AT28076 B AT 28076B
- Authority
- AT
- Austria
- Prior art keywords
- formaldehyde
- sulfoxylates
- ketone
- preparation
- acetone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- QJQZEJFUIOWFMS-UHFFFAOYSA-N formaldehyde;sulfanediol Chemical class O=C.OSO QJQZEJFUIOWFMS-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 150000002576 ketones Chemical class 0.000 claims description 3
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical class OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims 1
- -1 ketone sulfoxylates Chemical class 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- ZQRIKJMJOWMJGA-UHFFFAOYSA-L S([O-])[O-].CC(=O)C.[Na+].[Na+] Chemical compound S([O-])[O-].CC(=O)C.[Na+].[Na+] ZQRIKJMJOWMJGA-UHFFFAOYSA-L 0.000 description 3
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- BNPMFMACWNHVFE-UHFFFAOYSA-L S([O-])[O-].CC(=O)C.[Zn+2] Chemical compound S([O-])[O-].CC(=O)C.[Zn+2] BNPMFMACWNHVFE-UHFFFAOYSA-L 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 1
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Formaldehydsulfoxylaten.
Wie bei der Einwirkung von Formaldehyd auf Hydrosulfit, so entstehen auch bei der Einwirkung von Azeton oder Athylmethylketon auf alkalische Hydrosulfit Ketonsulfoxylate (vgl. D. R. P. Nr. 162875), die man durch Kristallisieren abtrennen kann.
Diese Ketonsulfoxylate werden auch erhalten, wenn man die Einwirkungsprodukte von Bisulfit, Schwefligsäure oder Hydrosulfit auf Azeton oder Äthylmethylketon bzw. jene Verbindung in Gegenwart der genannten Ketone der Reduktion unterwirft. Zur Darstellung der Ketonsulfoxylate verfährt man beispielsweise wie folgt : In eine Lösung von 65 Teilen Azeton in 1000 Teilen Wasser leitet man 64 Teile Schwefeldioxyd ein. Unter Umrühren und gutem Kühlen werden sodann 120 Teile Zinkstaub eingetragen und, wenn keine freiwillige Erwärmung mehr eintritt, die Temperatur auf 50-600 gesteigert. Nach mehrstündigem Erwärmen erhalt man eine Lösung des Azetonzinksulfoxylates. durch dessen Umsetzen mit Soda das Azetonnatriumsulfoxylat zu gewinnen ist.
Es wurde nun gefunden, dass die Ketonsulfoxylate in die beständigeren Formaldehyd- su ! foxylat. e übergeführt werden können, indem man jene mit Formaldehyd versetzt. Bei der Einwirkung von Formaldehyd auf die Ketonsulfoxylate wird das Keton aus der Verbindung verdrängt unter Bildung des Formaldehydsulfoxylates ; dies gibt sich dadurch zu erkennen, dass die mit der äquivalenten Menge Formaldehyd versetzte Lösung des Ketonsulfoxylates in der Kälte Indigcsulfosäure nicht mehr reduziert. Das Verfahren zur Gewinnung der Formaldohydsulfoxylate aus den Ketonsulfoxylaten gestaltet sich beispielsweise wie folgt :
Eine Lösung von 140 Teilen Azetonnatriumsulfoxylat (1000/0) in 1 l Wasser wird mit 75 Teilen Formaldehyd (400/0) versetzt und verrührt.
Die Umsetzung erfolgt sehr schnell und durch Eindampfen im Vakuum gewinnt man dann das Formaldehydnatriumsulfoxylat, während das Azeton abdestilliert.
An Stelle des Azetonnatriumsulfoxylates können andere Salze, z. B. das Zinksalz in gleicher Weise zur Verwendung gelangen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of formaldehyde sulfoxylates.
As with the action of formaldehyde on hydrosulfite, the action of acetone or ethyl methyl ketone on alkaline hydrosulfite also produces ketone sulfoxylates (see D. R. P. No. 162875), which can be separated off by crystallization.
These ketone sulfoxylates are also obtained when the action products of bisulfite, sulfurous acid or hydrosulfite on acetone or ethyl methyl ketone or that compound are subjected to reduction in the presence of the ketones mentioned. The procedure for preparing the ketone sulfoxylates is as follows: 64 parts of sulfur dioxide are introduced into a solution of 65 parts of acetone in 1000 parts of water. With stirring and good cooling, 120 parts of zinc dust are then introduced and, when voluntary heating no longer occurs, the temperature is increased to 50-600. After several hours of heating, a solution of the acetone zinc sulfoxylate is obtained. the acetone sodium sulfoxylate can be obtained by reacting it with soda.
It has now been found that the ketone sulfoxylates convert into the more stable formaldehyde su! foxylate. e can be converted by adding formaldehyde to them. When formaldehyde acts on the ketone sulfoxylates, the ketone is displaced from the compound with the formation of the formaldehyde sulfoxylate; This is evident from the fact that the solution of the ketone sulfoxylate to which the equivalent amount of formaldehyde has been added in the cold no longer reduces indigo sulfonic acid. The process for obtaining the formaldehyde sulfoxylates from the ketone sulfoxylates is as follows:
A solution of 140 parts of acetone sodium sulfoxylate (1000/0) in 1 l of water is mixed with 75 parts of formaldehyde (400/0) and stirred.
The reaction takes place very quickly and the sodium formaldehyde sulfoxylate is then obtained by evaporation in vacuo, while the acetone is distilled off.
Instead of the acetone sodium sulfoxylate, other salts, e.g. B. the zinc salt can be used in the same way.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT28076T | 1906-02-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT28076B true AT28076B (en) | 1907-04-10 |
Family
ID=3540605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT28076D AT28076B (en) | 1906-02-17 | 1906-02-17 | Process for the preparation of formaldehyde sulfoxylates. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT28076B (en) |
-
1906
- 1906-02-17 AT AT28076D patent/AT28076B/en active
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