DE832146C - Process for the stabilization of technical chloral - Google Patents
Process for the stabilization of technical chloralInfo
- Publication number
- DE832146C DE832146C DEP26019A DEP0026019A DE832146C DE 832146 C DE832146 C DE 832146C DE P26019 A DEP26019 A DE P26019A DE P0026019 A DEP0026019 A DE P0026019A DE 832146 C DE832146 C DE 832146C
- Authority
- DE
- Germany
- Prior art keywords
- chloral
- stabilization
- technical
- technical chloral
- formula
- 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
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims 2
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 150000003851 azoles Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000003585 thioureas Chemical class 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- -1 chloral dithiocarbamic acid ester Chemical class 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims 1
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 3
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 1
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/86—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Farbwerke Hoechst, vormals Meister Lucius & Brüning, Frankfurt/M.-Höchst Es ist bekannt, daß Chloral in nicht ganz reinem Zustand sich allmählich in eine feste weiße Masse verwandelt, welche ein polymeres Produkt darstellt (Metachloral). Vor allem wirken kleine Mengen von Schwefelsäure und Eisensalzen, die im technischen Chloral enthalten sein können, beschleunigend auf diese Polymerisation.Farbwerke Hoechst, formerly Master Lucius & Brüning, Frankfurt / M.-Höchst It is known that chloral in a not entirely pure state gradually turns into a transformed into a solid white mass, which is a polymeric product (metachloral). Mainly act small amounts of sulfuric acid and iron salts, which in the technical Chloral may be contained, accelerating this polymerization.
Es wurde nun gefunden, daß man die Polymerisation des Chlorals verhindern kann, wenn man ihm Dithiocarbaminsäureester, Thioharnstoffe oder schwefelhaltige Azole der Benzol- und Naphthalinreihe zusetzt.It has now been found that the polymerization of chloral can be prevented can, if you give him dithiocarbamic acid esters, thioureas or sulfur-containing Adds azoles of the benzene and naphthalene series.
Es sind i>eisl)iels«-eisel>rauchbarDith,iocanbaminsäureester der allgemeinen Formel: worin R, R', R" H, C H3, C2 Hs und andere APkylreste sein können.There are i> eisl) iels «-isel> smokable dith, iocanbamic acid ester of the general formula: where R, R ', R "can be H, C H3, C2 Hs and other A-alkyl radicals.
Als brauchbare Azole seien genannt Verbindungen der Formel worin `Y = O, N H, S, Se bedeuten ,können, ferner 2-Alkyl- oder 2-Halogenbenzthiazole. Das 2-Mercaptobenzthiazol hat sich als ganz besonders brauchbar erwiesen. Endlich sind substituierte Thioharnstoffe vom Typus worin R=H, CH., C2 HS,Cg H5 und R' = Phenyl, Äthyl, Methyl, usw. bedeuten 'können, wirksam. Von ihnen zeigt der Phenylthioharnstoff eine besonders gute Wirkung.Compounds of the formula may be mentioned as useful azoles where `Y = O, NH, S, Se can, furthermore 2-alkyl- or 2-halobenzothiazoles. The 2-mercaptobenzothiazole has proven to be particularly useful. Finally, substituted thioureas are of the type where R = H, CH., C2 HS, Cg H5 and R '= phenyl, ethyl, methyl, etc.' can be effective. Of these, the phenylthiourea shows a particularly good effect.
Es brauchen dem Chloral nur geringe Mengen dieser Stakili.satoren zugesetzt @zu werden. Sie lassen sich im Einzelfall leicht feststellen.Only small quantities of these stabilizers are needed for chloral to be added @to. They can easily be determined in individual cases.
Derart behandeltes technisches Chloral zeigt, sich selbst überlassen, auch nach neunmonatigem Stehen keinerlei Polymerisation, gleichgültig, welche Verunreinigungen es enthält. Beispiele i. In einem Kessel mit Rührwerk werden in ioo Teile technisches Chloral o,i Teil Phenylthioharnstoff der Formel eingetragen. Nach beendeter Lösung kann das Chloral gelagert werden und ist so viele Monate beständig.Technical chloral treated in this way shows, left to its own devices, no polymerization whatsoever, even after standing for nine months, regardless of the impurities it contains. Examples i. In a kettle with a stirrer, 100 parts technical chloral are o, i part phenylthiourea of the formula registered. Once the solution is complete, the chloral can be stored and is stable for many months.
2. ioo Teile Chlorar werden bei Raumtemperatur mit 0,05 Teilen
2-Mercaptobenzthiazol der Formel
versetzt. Nach beendeter Lösung des Stabilisators ist das Chloral völlig beständig.
3. Ioo Teile Chloral mit o, r Teil Dithiocarbaminsäureester der Formel
versetzt, ergeben ein weitgehend beständiges Chloral. In gleicher Weise können auch
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP26019A DE832146C (en) | 1948-12-22 | 1948-12-22 | Process for the stabilization of technical chloral |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP26019A DE832146C (en) | 1948-12-22 | 1948-12-22 | Process for the stabilization of technical chloral |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE832146C true DE832146C (en) | 1952-02-21 |
Family
ID=7370308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP26019A Expired DE832146C (en) | 1948-12-22 | 1948-12-22 | Process for the stabilization of technical chloral |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE832146C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1239688B (en) * | 1960-05-13 | 1967-05-03 | Geigy Ag J R | Stabilization of oxidation-sensitive organic substances |
-
1948
- 1948-12-22 DE DEP26019A patent/DE832146C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1239688B (en) * | 1960-05-13 | 1967-05-03 | Geigy Ag J R | Stabilization of oxidation-sensitive organic substances |
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