DE880298C - Process for stabilizing and improving the dissolving properties of formylated or acetylated amines - Google Patents
Process for stabilizing and improving the dissolving properties of formylated or acetylated aminesInfo
- Publication number
- DE880298C DE880298C DEP5394A DEP0005394A DE880298C DE 880298 C DE880298 C DE 880298C DE P5394 A DEP5394 A DE P5394A DE P0005394 A DEP0005394 A DE P0005394A DE 880298 C DE880298 C DE 880298C
- Authority
- DE
- Germany
- Prior art keywords
- formylated
- stabilizing
- improving
- amines
- dissolving properties
- 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
- 150000001412 amines Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 4
- 230000000087 stabilizing effect Effects 0.000 title claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- -1 aromatic oxy compound Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 2
- 229960001553 phloroglucinol Drugs 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zum Stabilisieren und Verbessern der Löseeigenschaften von formylierten oder acetylierten Aminen Das durch seine hervorragenden Eigenschaften als Lösungs- und Extraktionsmittel vielfach anwendbare Dimethylformamid und ähnliche formylierte oder acetylierte Amine sind in ihrer Verwendbarkeit dadurch stark beschränkt, daß sie bei höherer Temperatur leicht gespalten werden und die dabei auftretenden Spaltungsprodukte, insbesondere Ammoniak und Amine, durch ihren unangenehmen Geruch stören. Diese Verunreinigungen können ebenfalls die Lösefähigkeit nachteilig beeinflussen und ungünstig auf die Farbe der gelösten Stoffe einwirken.Process for stabilizing and improving the dissolving properties of formylated or acetylated amines that by its excellent properties Dimethylformamide and the like, which are widely used as solvents and extractants formylated or acetylated amines are very limited in their usability, that they are easily split at a higher temperature and the resulting Cleavage products, especially ammonia and amines, due to their unpleasant odor disturb. These impurities can also adversely affect the solvency and have an unfavorable effect on the color of the dissolved substances.
Besonders nachteilig ist, daß die Zersetzung unter Wärmeeinwirkung schon bei etwa 1a5°, also erheblich unter dem Siedepunkt, wenn auch nur in geringem Maße, so doch merklich beginnt. Zur Beseitigung dieses >,Übelstandes hat man bei der Herstellung von Polyacrylnitrillösungen in formylierten Aminen bereits vorgeschlagen, dem Lösungsmittel aminbindende Stoffe, wie Säuren, Säureanhydride, Ketone oder Aldehyde, zuzusetzen. Dadurch werden jedoch in das Lösungsmittel Fremdstoffe hineingebracht, deren Anwesenheit oft unerwünscht ist und die sich meist nur schwer entfernen lassen.It is particularly disadvantageous that decomposition occurs under the action of heat already at about 1a5 °, i.e. considerably below the boiling point, even if only slightly Dimensions, so it begins noticeably. To eliminate this>, deficiency one has at the production of polyacrylonitrile solutions in formylated amines has already been proposed, substances that bind amine to the solvent, such as acids, acid anhydrides, ketones or aldehydes, to add. However, this will bring foreign matter into the solvent, whose presence is often undesirable and which are usually difficult to remove.
Es wurde nun gefunden, daß die bei der Zersetzung gebildeten Amine bzw. das Ammoniak leicht beseitigt werden und eine weitere Zersetzung des Lösungsmittels weitgehend vermieden wird, wenn man dem Dimethylformamid bzw. einem ähnlichen Formyl-oder Acetylamin eine aromatische Oxyverbindung mit phenolischer Hydroxylgruppe zusetzt. Hierzu genügen Zusätze von o,oi bis o,1 °/o des Dimethylformamidgewichtes. Zweckmäßig werden als aromatische Oxyverbindungen die Di- und Trioxybenzole sowie die Oxyverbindungen mehrkerniger aromatischer Kohlenwasserstoffe verwandt, da diese einen relativ hohen Siedepunkt besitzen, so daß das behandelte Lösungsmittel durch Destillation bei normalem oder vermindertem Druck von den Reinigungszusätzen befreit werden kann. Man erhält also in einfachster Weise ein DimethyMormamid od. dgl., das sowohl frei von Ammoniak und Aminen als auch frei von den zur Reinigung benutzten Oxyaromaten ist.It has now been found that the amines formed during the decomposition or the ammonia can be easily removed and a further decomposition of the solvent is largely avoided if one of the dimethylformamide or a similar formyl or Acetylamine adds an aromatic oxy compound with a phenolic hydroxyl group. Additions of 0.1 to 0.1 percent of the weight of dimethylformamide are sufficient for this purpose. Appropriate Di- and trioxybenzenes as well as the oxy compounds are used as aromatic oxy compounds related to polynuclear aromatic hydrocarbons, as these have a relatively high Have boiling point, so that the treated solvent by distillation at normal or reduced pressure can be freed from the cleaning additives. So you get in the simplest way a DimethyMormamid or the like. That both free from ammonia and amines as well as free from the oxyaromatics used for cleaning is.
Beispiel Technisches Dimethylformamid wird nach Zusatz von o,i % Phloroglucin unter Atmosphärendruck bei 15o bis i53° destilliert. Das Destillat zeigt keinen störenden Fremdgeruch und ist praktisch frei von Ammoniak und Aminen. Es bleibt auch bei längerem Stehen vollkommen stabil und ergibt z. B. bei der Verwendung als Lösungsmittel für Polyacrylnitril bei Temperaturen unter ioo° auch nach mehrtägigem Stehenlassen keine Verfärbung.Example Technical dimethylformamide is distilled after the addition of 0.1% phloroglucinol under atmospheric pressure at 150 to 153 °. The distillate has no unpleasant foreign odor and is practically free of ammonia and amines. It remains completely stable even when you stand for a long time. B. when used as a solvent for polyacrylonitrile at temperatures below ioo ° no discoloration even after standing for several days.
An Stelle von Phloroglucin kann mit gleichem Erfolg Hydrochinon oder ß-Naphthol in Mengen von etwa 0,04 °/o genommen werden.Instead of phloroglucine, hydroquinone or β-naphthol can be taken in amounts of about 0.04 per cent.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP5394A DE880298C (en) | 1951-04-15 | 1951-04-15 | Process for stabilizing and improving the dissolving properties of formylated or acetylated amines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP5394A DE880298C (en) | 1951-04-15 | 1951-04-15 | Process for stabilizing and improving the dissolving properties of formylated or acetylated amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE880298C true DE880298C (en) | 1953-06-22 |
Family
ID=7359975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP5394A Expired DE880298C (en) | 1951-04-15 | 1951-04-15 | Process for stabilizing and improving the dissolving properties of formylated or acetylated amines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE880298C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1014998B (en) * | 1954-10-09 | 1957-09-05 | Boehringer Sohn Ingelheim | Process for the N-alkylation of compounds with nitrogen-containing ring systems |
-
1951
- 1951-04-15 DE DEP5394A patent/DE880298C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1014998B (en) * | 1954-10-09 | 1957-09-05 | Boehringer Sohn Ingelheim | Process for the N-alkylation of compounds with nitrogen-containing ring systems |
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