DE362743C - Process for the preparation of glyoxal sulfate and glyoxal - Google Patents
Process for the preparation of glyoxal sulfate and glyoxalInfo
- Publication number
- DE362743C DE362743C DEC28503D DEC0028503D DE362743C DE 362743 C DE362743 C DE 362743C DE C28503 D DEC28503 D DE C28503D DE C0028503 D DEC0028503 D DE C0028503D DE 362743 C DE362743 C DE 362743C
- Authority
- DE
- Germany
- Prior art keywords
- glyoxal
- sulfate
- preparation
- sulfuric acid
- tetrahaloethanes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 title claims description 34
- 229940015043 glyoxal Drugs 0.000 title claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910001385 heavy metal Inorganic materials 0.000 claims description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910000370 mercury sulfate Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- -1 bisulfite compound Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Glyoxalsulfat und Glyoxal. Die mehrfach halogenierten Kohlenwasserstoffe der Paraffinreihe sind in der Regel sehr reaktionsträge Körper. Es wurde nun die überraschende Beobachtung gemacht, daß symmetrische Tetrahalogenäthane durch Behandlung mit rauchender Schwefelsäure, vorteilhaft bei Gegenwart von Schwermetallverbindungen, sich in ein Sulfat des Glyoxals umwandeln lassen. Die Konzentration des Oleums sowie die Temperatur können dabei in weiten Grenzen-schwanken. Die Reaktion verläuft vermutlich nach der Gleichung: Das so entstehende Glyoxalsulfat.kristallisiert größtenteils aus der zurückbleibenden Chlorsulfonsäure aus. Es bildet farblose Nädelchen, die unter Zersetzung bei 176 bis i77° schmelzen und sich durch sehr große Reaktionsfähigkeit auszeichnen. Beim Erhitzen mit Wasser findet Abspaltung von Schwefelsäure statt; durch Ausfällen mit Barythydrat oder Kalk gelingt es dann leicht, eine wässerige Lösung von Glyoxal zu erhalten.Process for the preparation of glyoxal sulfate and glyoxal. The multiply halogenated hydrocarbons of the paraffin series are usually very inert bodies. The surprising observation has now been made that symmetrical tetrahaloethanes can be converted into a sulfate of glyoxal by treatment with fuming sulfuric acid, advantageously in the presence of heavy metal compounds. The concentration of the oleum and the temperature can fluctuate within wide limits. The reaction probably proceeds according to the equation: The resulting glyoxal sulfate largely crystallizes out of the remaining chlorosulfonic acid. It forms colorless needles which melt with decomposition at 176 to 177 ° and are characterized by their very high reactivity. When heated with water, sulfuric acid is split off; by precipitation with baryta hydrate or lime it is easy to obtain an aqueous solution of glyoxal.
Damit ist die Möglichkeit gegeben, das bisher schwer zugängliche Glyoxal bequem darzustellen und es für technische Zwecke nutzbar zu machen.This gives the opportunity to use glyoxal, which was previously difficult to access easy to represent and make it usable for technical purposes.
Beispiel r. Darstellung von Glyoxalsulfat.Example r. Representation of glyoxal sulfate.
Zu 5o Teilen Tetrachloräthan, in dem z Teil Quecksilbersulfat suspendiert ist, läßt man t2o Gewichtsteile Oleum von 65 Prozent unter Rühren zulaufen, wobei die Temperatur zweckmäßig bei So bis 6o° gehalten wird. Wenn beim Abkühlen keine Zunahme der Kristallabscheidung erfolgt, ist die Reaktion beendet; man kühlt dann ab und nutscht die ausgeschiedenen Kristalle ab. Aus dem Filtrat wird im Vakuum die Chlorsulfonsäure abdestilliert, wobei noch etwas Glyoxal bzw. Glyoxalsulfat erhalten wird. Die Kristalle selbst werden erst mit Schwefelsäure, dann mit Eiswasser gewaschen und vorsichtig getrocknet.To 50 parts of tetrachloroethane, in which z part of mercury sulfate is suspended t2o parts by weight of 65 percent oleum are allowed to run in with stirring, with the temperature is expediently kept at 50 to 60 °. If there is no when it cools down If there is an increase in crystal deposition, the reaction has ended; one then cools and sucks off the precipitated crystals. The filtrate becomes in vacuo the chlorosulfonic acid is distilled off, with some glyoxal or glyoxal sulfate is obtained. The crystals themselves are first made with sulfuric acid, then with ice water washed and carefully dried.
An Stelle des Quecksilbersulfates kann Kupfersulfat oder ein anderes Schwermetallsalz verwendet werden. Man kann auch auf den Zusatz eines solchen ganz verzichten.In place of the mercury sulfate can be copper sulfate or another Heavy metal salt can be used. One can also rely entirely on the addition of such waive.
Beispiel e. Darstellung von Glyoxal.Example e. Representation of glyoxal.
Die nach Beispiel z erhaltenen Kristalle von Glyoxalsulfat werden mit Wasser erwärmt, bis völlige Lösung eingetreten ist. Hierauf wird mit Baryumhydroxyd die Schwefelsäure ausgefällt und filtriert. Das Filtrat enthält das Glyoxal, das durch vorteilhaft möglichst rasches Eindampfen im Vakuum in konzentrierter Form erhalten oder in bekannter Weise in die Bisulfitverbindung iibergeführt werden kann.The crystals of glyoxal sulfate obtained according to Example z are heated with water until complete solution has occurred. On that the sulfuric acid is precipitated with barium hydroxide and filtered. The filtrate contains the glyoxal, which is advantageous by evaporation as quickly as possible in a vacuum obtained in concentrated form or in a known manner into the bisulfite compound can be transferred.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC28503D DE362743C (en) | 1919-11-12 | 1919-11-12 | Process for the preparation of glyoxal sulfate and glyoxal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC28503D DE362743C (en) | 1919-11-12 | 1919-11-12 | Process for the preparation of glyoxal sulfate and glyoxal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE362743C true DE362743C (en) | 1922-11-02 |
Family
ID=7018661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC28503D Expired DE362743C (en) | 1919-11-12 | 1919-11-12 | Process for the preparation of glyoxal sulfate and glyoxal |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE362743C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2415397A (en) * | 1944-12-06 | 1947-02-04 | Gen Aniline & Film Corp | Method of preparing glyoxal sulphate |
-
1919
- 1919-11-12 DE DEC28503D patent/DE362743C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2415397A (en) * | 1944-12-06 | 1947-02-04 | Gen Aniline & Film Corp | Method of preparing glyoxal sulphate |
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