CH247990A - Process for the production of a high molecular weight product containing sulfur and nitrogen. - Google Patents
Process for the production of a high molecular weight product containing sulfur and nitrogen.Info
- Publication number
- CH247990A CH247990A CH247990DA CH247990A CH 247990 A CH247990 A CH 247990A CH 247990D A CH247990D A CH 247990DA CH 247990 A CH247990 A CH 247990A
- Authority
- CH
- Switzerland
- Prior art keywords
- molecular weight
- high molecular
- production
- nitrogen
- melt
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 2
- 229910052717 sulfur Inorganic materials 0.000 title description 2
- 239000011593 sulfur Substances 0.000 title description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title 2
- 229910052757 nitrogen Inorganic materials 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 239000007859 condensation product Substances 0.000 claims description 7
- 239000000155 melt Substances 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 239000001361 adipic acid Substances 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines hochmolekularen schwefel- und stickstoffhaltigen Produktes. Es wurde gefunden, dass man ein hoch molekulares Kondensationsprodukt herstel len kann, wenn man Adipinsäuredithioamid auf 1.8 - Dichlor - oetandion - 2.7 einwirken lässt; dabei wird vorzugsweise in Gegenwart von Lösungsmitteln und/oder Kondensations- mitteln gearbeitet.
Man kann auch vom Adipinsäuredinitril ausgehen und auf dieses Schwefelwasserstoff und 1.8-Dichlor-octan- dion-2.7 einwirken lassen; dabei bildet sich intermediär Adipinsäuredithioamid.
Das neue Kondensationsprodukt bildet ein schwach bräunlich gefärbtes Pulver, das bei 105 zu schmelzen beginnt und bei 145 ohne Zersetzung klar schmilzt. Es ist gut löslich in Eisessig und verdünnten Mineral säuren. Durch weiteres Erwärmen auf 130 bis 170 wird der Schmelzpunkt auf 130 bis 145 erhöht; aus der Schmelze lässt sich bei einer Temperatur von 130-170 ein unend licher Faden ziehen. Das Kondensationsprodukt soll in der Kunststoffindustrie Verwendung finden.
Beispiel <I>Z:</I> 0,5g Adipinsäuredithioamid und 0,6 g 1.8-Dichlor-octandion-2.7 werden in 10 cm3 Eisessig gelöst und während drei Stunden unter Rückfluss zum Sieden erhitzt. Nach einer halben Stunde beginnt sich die vorher klare Lösung zu trüben. Nach beendeter Re <B>i</B> aktion <B>-</B> wird die Lösung mit verdünntem Ammoniak bis zur neutralen Reaktion ver setzt.
Dabei fällt eine zähflüssige Masse aus. Unter Äther aufbewahrt, wird sie fest und bildet .ein schwach bräunlich gefärbtes Pul ver, das bei 105 zu schmelzen beginnt und bei 145 ohne Zersetzung klar schmilzt.
Das Kondensationsprodukt ist gut löslich in Eisessig und verdünnten Mineralsäuren. Aus diesen Lösungen kann es mit verdünn tem Ammoniak, nicht aber mit Alkohol aus gefällt werden. Es ist ziemlich löslich in Methanol, Athanol, Benzol, Toluol, Pyridin, Diogan. Nach einigem Stehen scheidet es sich aus diesen Lösungen wieder als zähe Masse ab. Die Lösung in Benzol erstarrt beim Er kalten zu einem Gel. Die Kondensation lässt sich auch in Phe nol als Lösungsmittel durchführen.
Durch weiteres Erwärmen des Konden sationsproduktes auf 130-170 wird der Schmelzpunkt des Produktes auf 130-145 erhöht: in dieser. Phase ist das Produkt in Benzol noch löslich und lässt sich daraus durch Äther ausfällen. Aus der benzolischen Lösung kann ein Film gewonnen werden. Aus der Schmelze des Produktes lässt sich bei einer Temperatur von 130-170 ein un endlicher Faden ziehen, der je nach den Her stellungsbedingungen irreversibel dehnbar ist oder eine ausgesprochene kautschukähn liche Elastizität aufweist.
<I>Beispiel 2:</I> 1 Teil Adipinsäure-dinitril und 1,2 Teile 1.8-Dicblor-octandion-2.7 _werden in 5 Teilen Eisessig gelöst. In die erwärmte Lösung wird während längerer Zeit Schwefelwasser stoff eingeleitet, wobei die Lösung nach kur zer Zeit trübe wird. Nach dem Erkalten, Entfernung des Lösungsmittels und der Neutralisation mit Ammoniak erhält man ein Reaktionsprodukt, das sieh in Benzol lösen lässt und auf Zusatz von Äther wieder gefällt werden kann.
Das geschmolzene Pro= dukt zeigt fadenziehende Eigenschaften.
<I>Beispiel 3:</I> In die auf 100 erwärmte Lösung von 1 Teil Adipinsäuredinitril und 1,2 Teilen 1.8- Dichlor-octandion-2.7 in 6 Teilen Phenol wird Schwefelwasserstoff eingeleitet. Nach 5 Stunden wird die Temperatur während einer halben Stunde auf 130 erhöht. Nach der Entfernung des Phenols erhält man einen Rückstand, der sieh in Benzol löst und daraus mit Äther wieder abgeschieden werden kann, wobei ein Präparat resultiert, das in ge schmolzenem Zustande fadenziehende Eigen schaften aufweist.
Process for the production of a high molecular weight sulfur and nitrogen containing product. It has been found that a high molecular weight condensation product can be produced if adipic dithioamide is allowed to act on 1.8 - dichloro - oetanedione - 2.7; it is preferably carried out in the presence of solvents and / or condensation agents.
You can also start from adipic dinitrile and allow this hydrogen sulfide and 1.8-dichloro-octanedione-2.7 to act; adipic dithioamide is formed as an intermediate.
The new condensation product forms a pale brownish colored powder that begins to melt at 105 and melts clear at 145 without decomposition. It is easily soluble in glacial acetic acid and diluted mineral acids. Further heating to 130 to 170 increases the melting point to 130 to 145; An infinite thread can be drawn from the melt at a temperature of 130-170. The condensation product is to be used in the plastics industry.
Example <I> Z: </I> 0.5 g of adipic dithioamide and 0.6 g of 1.8-dichloro-octanedione-2.7 are dissolved in 10 cm3 of glacial acetic acid and heated to boiling under reflux for three hours. After half an hour, the previously clear solution begins to become cloudy. After the reaction has ended, the solution is mixed with dilute ammonia until a neutral reaction is achieved.
A viscous mass precipitates out. When stored under ether, it solidifies and forms a pale brownish powder that begins to melt at 105 and melts clear at 145 without decomposition.
The condensation product is readily soluble in glacial acetic acid and dilute mineral acids. It can be precipitated from these solutions with dilute ammonia, but not with alcohol. It is quite soluble in methanol, ethanol, benzene, toluene, pyridine, diogan. After standing for a while, it separates out of these solutions as a viscous mass. The solution in benzene solidifies to a gel when cold. The condensation can also be carried out in phenol as a solvent.
By further heating the condensation product to 130-170, the melting point of the product is increased to 130-145: in this. Phase, the product is still soluble in benzene and can be precipitated from it by ether. A film can be obtained from the benzene solution. An infinite thread can be drawn from the melt of the product at a temperature of 130-170, which, depending on the manufacturing conditions, can be irreversibly stretchable or has a pronounced rubber-like elasticity.
<I> Example 2: </I> 1 part of adipic acid dinitrile and 1.2 parts of 1.8-dicloro-octanedione-2.7 are dissolved in 5 parts of glacial acetic acid. Hydrogen sulphide is introduced into the heated solution for a long time, the solution becoming cloudy after a short time. After cooling, removal of the solvent and neutralization with ammonia, a reaction product is obtained which can be dissolved in benzene and which can be precipitated again with the addition of ether.
The melted product shows string-pulling properties.
<I> Example 3: </I> Hydrogen sulfide is passed into the heated to 100 solution of 1 part of adipic dinitrile and 1.2 parts of 1.8-dichloro-octanedione-2.7 in 6 parts of phenol. After 5 hours, the temperature is increased to 130 over half an hour. After the phenol has been removed, a residue is obtained which dissolves in benzene and can be separated out again with ether, the result being a preparation which, when melted, has stringy properties.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH247990T | 1945-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH247990A true CH247990A (en) | 1947-04-15 |
Family
ID=4466585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH247990D CH247990A (en) | 1945-07-18 | 1945-07-18 | Process for the production of a high molecular weight product containing sulfur and nitrogen. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH247990A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3065240A (en) * | 1960-08-03 | 1962-11-20 | Olin Mathieson | Thiazoles |
-
1945
- 1945-07-18 CH CH247990D patent/CH247990A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3065240A (en) * | 1960-08-03 | 1962-11-20 | Olin Mathieson | Thiazoles |
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