DE2207379B2 - Process for the recovery of polyethers from polyether urethane plastics - Google Patents
Process for the recovery of polyethers from polyether urethane plasticsInfo
- Publication number
- DE2207379B2 DE2207379B2 DE2207379A DE2207379A DE2207379B2 DE 2207379 B2 DE2207379 B2 DE 2207379B2 DE 2207379 A DE2207379 A DE 2207379A DE 2207379 A DE2207379 A DE 2207379A DE 2207379 B2 DE2207379 B2 DE 2207379B2
- Authority
- DE
- Germany
- Prior art keywords
- recovery
- polyether
- polyether urethane
- polyethers
- urethane
- 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.)
- Granted
Links
- 229920000570 polyether Polymers 0.000 title claims description 19
- 239000004721 Polyphenylene oxide Substances 0.000 title claims description 17
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 238000011084 recovery Methods 0.000 title claims description 8
- 239000004033 plastic Substances 0.000 title claims description 4
- 229920003023 plastic Polymers 0.000 title claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 230000029087 digestion Effects 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000002035 prolonged effect Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/14—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with steam or water
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/08—Polyurethanes from polyethers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/141—Feedstock
- Y02P20/143—Feedstock the feedstock being recycled material, e.g. plastics
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Description
Die Erfindung bezieht sich auf ein Verfahren zur Rückgewinnung von Polyäthem aus Polyätherurethan-Kunststoffen. The invention relates to a method for recovering polyether from polyether urethane plastics.
Polyurethane fallen bei der Herstellung von Schaumkörpern und anderen Formkörpern in verhältnismäßig großen Mengen an. Die Wiederverwendung dieser Abfallstoffe stößt auf Schwierigkeiten. Zur Rückgewinnung der Ausgangsstoffe ist es bereits bekanntgeworden, die Polyurethane einer Erhitzung unter Druck zu unterwerfen. Eine derartige Methode konnte sich in der Praxis jedoch nicht durchsetzen, weil die dabei erhaltenen Spaltprodukte eine umständliche Rückgewinnung notwendig machen, da sowohl die Urethanbindung als auch die Esterbindung dabei verseift werden.Polyurethanes are relatively common in the production of foam bodies and other molded bodies large amounts of. There are difficulties in reusing this waste material. For recovery of the starting materials, it has already become known to heat the polyurethanes under pressure subject. However, such a method could not prevail in practice because it was resulting cleavage products make a cumbersome recovery necessary, since both the urethane bond as well as the ester bond are saponified in the process.
Die anfallenden Glykole und Säuren müssen einer sorgfältigen Vakuumdestillation unterworfen werden, um brauchbare Produkte daraus zu gewinnen. Der Aufwand ist jedoch in der Regel größer als die erhaltenen Produkte dem Wert nach entsprechen.The resulting glycols and acids must be subjected to careful vacuum distillation, in order to obtain useful products from it. However, the effort is usually greater than that products received in terms of value.
Insbesondere bei Schaumstoffen werden in der jüngeren Zeit in großer Zahl Polyätherurethane verwendet. Ein thermischer Aufschluß ist bei diesen Erzeugnissen bisher nicht durchgeführt worden, wohl weil die Erfahrungen aus den bisherigen Rückgewinnungsvorgängen ungünstig waren.Polyether urethanes have recently been used in large numbers in the case of foams in particular used. A thermal digestion has so far not been carried out on these products because the experiences from the previous recovery processes were unfavorable.
Aus der deutschen Patentschrift 8 61 926 ist ein Verfahren zum Behandeln von Polyurethanabfällen bekannt, bei dem ein Aufschluß mit viel Wasser bei einer Temperatur von über 2500C und bei hohem Druck über mehrere Stunden erfolgt. Hierbei tritt wie vorgesehen eine totale Zerlegung der Polyurethanausgangsmasse in Diole und Diamine ein. Dieser Aufschluß führt nur zu Monomeren und läßt sich für eine Rückgewinnung von Polyäthem aus entsprechenden Polyätherurethan nicht anwenden. Fin solches Polymerer würde, wenn es in dem Ausgangsmaterial enthalten wäre, über die genannten Bedingungen ebenfalls in Monomers aufgespalten. A method for treating polyurethane waste is known from German patent specification 8 61 926, in which digestion takes place with a lot of water at a temperature of over 250 ° C. and at high pressure for several hours. Here, as intended, the polyurethane starting material is completely broken down into diols and diamines. This digestion only leads to monomers and cannot be used for the recovery of polyether from the corresponding polyether urethane. Such a polymer, if it were contained in the starting material, would also be split into monomers via the conditions mentioned.
Auch nach der deutschen Patentschrift 9 67 601 tritt durch die alkalische Verseifung bei hoher Temperatur und bei hohem Druck in wäßriger Phase ein vollständiger Abbau zu Dioden und Diaminen ein. Auch auf diesem Wege konnten die Polyäther aus entsprechenden Polyätherurethan ebenfalls nicht zurückgewonnen werden, weil die Arbeitsbedingungen für die Rückgewinnung zu hart sind. Darüber hinaus führt ein alkalischer Aufschluß zu erheblichen Nachteilen bei der späteren Isolierung von Polyäthem.Also according to the German patent 9 67 601 occurs through the alkaline saponification at high temperature and complete degradation to diodes and diamines occurs at high pressure in the aqueous phase. Even In this way, the polyethers could not be recovered from the corresponding polyether urethane either because the working conditions are too harsh for recovery. It also introduces alkaline digestion leads to considerable disadvantages in the subsequent isolation of polyether.
Die Erfindung besteht in einem Verfahren zur Rückgewinnung von Polyäthem aus Kunststoffen auf Basis Polyätherurethan durch längeres Erhitzen auf 150 bis 220° C in einem geschlossenen Behälter in Gegenwart von Wasser bei einem Druck von ca. 20 atü, das dadurch gekennzeichnet ist, daß der Aufschluß bei einer Dauer von ca. 100 Minuten in Wasserdampf erfolgt, die Spaltprodukte in Toluol oder einem anderen organischen Lösungsmittel aufgenommen, mit 5%iger SaIzsäure behandelt werden und nach dem Dekantieren der wäßrigen Phase das Lösungsmittel abgedampft wird.The invention consists in a method for the recovery of polyether from plastics Based on polyether urethane by prolonged heating to 150 to 220 ° C in a closed container in the presence of water at a pressure of about 20 atmospheres, which is characterized in that the digestion at a Duration of about 100 minutes in steam that takes place Cleavage products taken up in toluene or another organic solvent, with 5% hydrochloric acid are treated and, after decanting the aqueous phase, the solvent is evaporated.
In dem angegebenen Temperaturinterval wird zwar ebenfalls die Urethangruppe gespalten, jedoch bleibt die Äthergruppe der Polyätherurethane weitgehend unverändert erhalten. Es ist nur eine geringfügige Erhöhung der Hydroxylzahl festzustellen. Der auf diese Weise erhaltene Polyäther kann in kontinuierlicher Arbeitsweise aufgearbeitet und wieder verwendet werden. Auch die erhaltenen Amine können als Ausgangsstoffe für die Diisocyanate auf bekannte Weise wiederIn the specified temperature interval, also split the urethane group, but the ether group of the polyether urethanes remains largely unchanged obtain. There is only a slight increase in the hydroxyl number. That way Polyether obtained can be worked up and reused in a continuous procedure. The amines obtained can also be used as starting materials for the diisocyanates in a known manner
verwendet werden.be used.
In einen Autoklav von 501 Inhalt werden 5 kg Polyätherurethan gegeben. Unter direktem Dampfdruck von 20 atü wird das Polyätherurethan auf 180° für ca. 100 Minuten erwärmt. Nachdem die so behandelte Masse aus dem Autoklaven entnommen ist, wird sie in organische Lösungsmittel, wie z. B. Toluol gelöst, mit 5%iger Salzsäure versetzt, so daß die aus der Urethangruppenspaltung enstandenen Amine durch Dekantieren entfernt werden können. Die organische Lösung wird eingedampft, filtriert und als Rückstand ein Polyäther erhalten, der ein Molgewicht von ca. 3000 und eine Hydroxylzahl von ca. 40 aufweist.5 kg of polyether urethane are placed in an autoclave with a capacity of 50 liters. Under direct steam pressure The polyether urethane is heated from 20 atmospheres to 180 ° for approx. 100 minutes. After being so treated Mass is removed from the autoclave, it is in organic solvents, such as. B. toluene dissolved with 5% hydrochloric acid added, so that the amines formed from the cleavage of urethane groups through Decanting can be removed. The organic solution is evaporated, filtered and concentrated as a residue Polyether obtained which has a molecular weight of about 3000 and a hydroxyl number of about 40.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2207379A DE2207379B2 (en) | 1972-02-17 | 1972-02-17 | Process for the recovery of polyethers from polyether urethane plastics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2207379A DE2207379B2 (en) | 1972-02-17 | 1972-02-17 | Process for the recovery of polyethers from polyether urethane plastics |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2207379A1 DE2207379A1 (en) | 1973-08-30 |
| DE2207379B2 true DE2207379B2 (en) | 1978-06-22 |
| DE2207379C3 DE2207379C3 (en) | 1979-03-22 |
Family
ID=5836183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2207379A Granted DE2207379B2 (en) | 1972-02-17 | 1972-02-17 | Process for the recovery of polyethers from polyether urethane plastics |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2207379B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013350A1 (en) * | 1978-12-20 | 1980-07-23 | Bayer Ag | Process for splitting up polyurethane hydrolysis products into polyol and polyamine |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1601787A (en) * | 1977-08-22 | 1981-11-04 | Ford Motor Co | Hydrolytic decomposition method and apparatus |
| DE3034680A1 (en) | 1980-09-13 | 1982-04-29 | Bayer Ag, 5090 Leverkusen | IMPROVED METHOD FOR SEPARATING POLYURETHANE HYDROLYSATES IN POLYETHER AND DIAMINE |
| DE4028724C2 (en) * | 1990-09-10 | 1997-04-30 | Eisenmann Kg Maschbau | Process and device for the disposal and incineration of production residues from polyurethane foams |
| JP2024544908A (en) | 2021-11-12 | 2024-12-05 | コベストロ、ドイチュラント、アクチエンゲゼルシャフト | Method for recovering raw materials from polyurethane products |
| WO2025125285A1 (en) | 2023-12-14 | 2025-06-19 | Covestro Deutschland Ag | Method for recovering valuable substances from polyurethane foams |
| WO2025125284A1 (en) | 2023-12-14 | 2025-06-19 | Covestro Deutschland Ag | Method for recovering valuable substances from polyurethane foams |
-
1972
- 1972-02-17 DE DE2207379A patent/DE2207379B2/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013350A1 (en) * | 1978-12-20 | 1980-07-23 | Bayer Ag | Process for splitting up polyurethane hydrolysis products into polyol and polyamine |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2207379A1 (en) | 1973-08-30 |
| DE2207379C3 (en) | 1979-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |