EP0468087A1 - Process for working up used hydraulic fluids containing ethers of glycol as base material and borates of glycol ethers - Google Patents
Process for working up used hydraulic fluids containing ethers of glycol as base material and borates of glycol ethers Download PDFInfo
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- EP0468087A1 EP0468087A1 EP90119391A EP90119391A EP0468087A1 EP 0468087 A1 EP0468087 A1 EP 0468087A1 EP 90119391 A EP90119391 A EP 90119391A EP 90119391 A EP90119391 A EP 90119391A EP 0468087 A1 EP0468087 A1 EP 0468087A1
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- Prior art keywords
- borates
- glycol ethers
- glycol
- transesterification
- trialkyl
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M175/00—Working-up used lubricants to recover useful products ; Cleaning
- C10M175/0075—Working-up used lubricants to recover useful products ; Cleaning synthetic oil based
Definitions
- the invention relates to a method for the preparation of used hydraulic fluids based on glycol ethers containing glycol ether borates.
- Hydraulic fluids of the aforementioned type are used in particular as brake fluids in the hydraulic brake systems of vehicles in order to transmit the brake pressure to the brake cylinders.
- Such hydraulic fluids are subject to special requirements, for example they should be cold and heat resistant, non-corrosive and resistant to aging.
- commercially available hydraulic fluids which are well suited as brake fluids also contain high proportions, e.g. 50 to 70% by weight of glycol ether borates.
- These boric acid esters can bind water penetrating into the brake fluid considerably more than the pure glycol ethers. This is extremely important for the maintenance of a reliable hydraulic brake system, because if the water entering does not bind effectively enough, the boiling point of the brake fluid will drop to that of the water, with the result that it will be at a temperature of 100 ° C or more Vapor bubbles form in the wheel cylinders, which inevitably lead to a total failure of the braking system.
- the glycol ether borates bring about a significant reduction in the water partial pressure and thus ensure an increased wet boiling point of the hydraulic fluid used as the brake fluid.
- the invention is therefore based on the object of providing a process for the preparation of used hydraulic fluids based on glycol ethers with a content of glycol ether borates which can be carried out economically advantageously under mild conditions and which enables the glycol ether products to be cleaned to such an extent that they produce fresh hydraulic fluids can be used for hydraulic brake systems.
- the transesterification converts the glycol ether borates, which cannot be distilled under mild conditions, to trialkyl borates, which boil significantly lower than the glycol ethers present in the hydraulic fluid and formed during the transesterification. They can therefore be separated from the latter without difficulty, preferably by distillation under normal pressure or slightly elevated pressure, for example from 1.2 to 10 bar.
- the process according to the invention can be carried out in this way under mild conditions and, in addition to the glycol ethers purified by fractional distillation, provides high-purity trialkyl borates, which are reacted to glycol ether borates either by re-esterification with glycol ethers, in particular with methyl triglycol, and mixed with a corresponding amount of glycol ether to form a fresh hydraulic fluid or can be further processed in a manner known per se to pure boric acid esters and / or pure boric acid.
- Monohydric alcohols having 1 to 3 carbon atoms are preferably used for the transesterification as short-chain aliphatic alcohols.
- Methanol is very particularly preferably used for the transesterification.
- the transesterification of the glycol ether borates is carried out by the process according to the invention with an excess of at least 38% by weight of one or more short-chain aliphatic alcohols, based on the amount required for the stoichiometric transesterification of the glycol ether borates, preferably an alcohol excess in the range from 38 to 150% by weight. %, very particularly preferably in the range from 38 to 100% by weight.
- the trialkylborates formed are separated from the reaction mixture together with excess alcohol by distillation, if appropriate as an azeotropic mixture.
- An embodiment is particularly preferred in which the trialkyl borates formed are distilled off together with excess methanol as an azeotrope at 54 to 55 ° C. under normal pressure continuously from the reaction mixture.
- the azeotrope has a composition of 73% by weight of boric acid ester and 27% by weight of methanol.
- an azeotropic mixture of trialkyl borates and an aliphatic alcohol together with glycol ethers and water is heated to boiling under atmospheric pressure, alcohol and water being distilled off and the trialkyl borates being esterified with the glycol ethers to give the desired glycol ether borates.
- the recovered glycol ether fractions correspond in their purity to the requirements placed on raw materials for the production of new brake fluids, in particular because the process according to the invention can substantially reduce the thermal load compared to alkaline hydrolysis.
- boric acid instead of boric acid, boric anhydride can also be used.
- Another part of the azeotrope obtained from trimethyl borate and methanol was washed with Was hydrolytically decomposed, the methanol being recovered and pure boric acid being obtained.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
Description
Die Erfindung betrifft ein Verfahren zur Aufbereitung gebrauchter Hydraulikflüssigkeiten auf der Basis von Glykolethern mit einem Gehalt an Glykoletherboraten.The invention relates to a method for the preparation of used hydraulic fluids based on glycol ethers containing glycol ether borates.
Hydraulikflüssigkeiten der vorbezeichneten Art werden insbesondere als Bremsflüssigkeiten in den hydraulischen Bremssystemen von Fahrzeugen benutzt, um den Bremsdruck zu den Bremszylindern weiterzuleiten. An solche Hydraulikflüssigkeiten werden besondere Anforderungen gestellt, beispielsweise sollen sie kälte- und wärmebeständig, nicht korrodierend und alterungsbeständig sein.Hydraulic fluids of the aforementioned type are used in particular as brake fluids in the hydraulic brake systems of vehicles in order to transmit the brake pressure to the brake cylinders. Such hydraulic fluids are subject to special requirements, for example they should be cold and heat resistant, non-corrosive and resistant to aging.
Als Bremsflüssigkeiten gut geeignete handelsübliche Hydraulikflüssigkeiten enthalten neben Glykolethern wie Triethylenglykol-monomethyether (= Methyltriglykol) auch hohe Anteile, z.B. 50 bis 70 Gew.-%, an Glykoletherboraten. Diese Borsäureester können in die Bremsflüssigkeit eindringendes Wasser erheblich stärker binden als die reinen Glykolether. Dies ist für die Aufrechterhaltung eines zuverlässig wirkenden hydraulischen Bremssystems außerordentlich wichtig, weil das eindringende Wasser, wenn es nicht wirksam genug gebunden wird, den Siedepunkt der Bremsflüssigkeit auf den des Wassers herabdrückt mit der Folge, daß sich bei einer Temperatur von 100° C oder mehr in den Radzylindern Dampfblasen bilden, die Zwangsläufig zu einem Totalausfall des Bremssystems führen. Die Glykoletherborate bewirken eine deutliche Herabsetzung des Wasserpartialdruckes und sorgen dadurch für einen erhöhten Naßsiedepunkt der als Bremsflüssigkeit verwendeten Hydraulikflüssigkeit.In addition to glycol ethers such as triethylene glycol monomethyl ether (= methyltriglycol), commercially available hydraulic fluids which are well suited as brake fluids also contain high proportions, e.g. 50 to 70% by weight of glycol ether borates. These boric acid esters can bind water penetrating into the brake fluid considerably more than the pure glycol ethers. This is extremely important for the maintenance of a reliable hydraulic brake system, because if the water entering does not bind effectively enough, the boiling point of the brake fluid will drop to that of the water, with the result that it will be at a temperature of 100 ° C or more Vapor bubbles form in the wheel cylinders, which inevitably lead to a total failure of the braking system. The glycol ether borates bring about a significant reduction in the water partial pressure and thus ensure an increased wet boiling point of the hydraulic fluid used as the brake fluid.
Trotz dieser Vorkehrungen ist das Wasseraufnahmevermögen derartiger Hydraulikflüssigkeiten begrenzt. Beim Überschreiten dieser Grenze fällt der Siedepunkt der Hydraulikflüssigkeit bei weiterer Wasseraufnahme unter einen noch akzeptierbaren Wert, wodurch die Hydraulikflüssigkeit die für eine Bremsflüssigkeit erforderlichen Mindestanforderungen nicht mehr erfüllt und gegen unverbrauchte Hydraulikflüssigkeit ausgewechselt werden muß. Da es sich nicht vermeiden läßt, daß die Bremsanlagen von Fahrzeugen aller Art mehr oder weniger häufig der Nässe ausgesetzt sind, bedeutet dies, daß die Hydraulikflüssigkeiten nach einiger Zeit die Grenze ihres Wasseraufnahmevermögens erreichen und damit verbraucht sind. Ein regelmäßiger Wechsel der Hydraulikflüssigkeit in den hydraulischen Bremsanlagen ist daher erforderlich, wodurch allein im Inland derzeit pro Jahr etwa 8000 t verbrauchte Hydraulikflüssigkeiten der oben beschriebenen Art anfallen.Despite these precautions, the water absorption capacity of such hydraulic fluids is limited. If this limit is exceeded, the boiling point of the hydraulic fluid falls below a still acceptable value when water is absorbed further, as a result of which the hydraulic fluid no longer meets the minimum requirements required for a brake fluid and must be replaced with unused hydraulic fluid. Since it cannot be avoided that the brake systems of vehicles of all kinds are more or less frequently exposed to the wet, this means that the hydraulic fluids reach the limit of their water absorption capacity after some time and are therefore used up. A regular change of the hydraulic fluid in the hydraulic brake systems is therefore necessary, which means that around 8000 t of hydraulic fluids of the type described above are currently generated annually in Germany alone.
Versuche, verbrauchte Hydraulikflüssigkeiten der vorbeschriebenen Art durch destillative Rückgewinnung der in ihnen enthaltenen Rohstoffe zu verwerten, wie das beispielsweise bei verbrauchtem Motorenöl seit langem praktisch durchgeführt wird, erwiesen sich als technisch nicht praktikabel und scheiterten insbesondere daran, daß die Glykoletherborate einen Siedepunkt von über 300 C haben und sich auch in der Vakuumdestillation partiell zersetzen.Attempts to utilize used hydraulic fluids of the type described above by recovering the raw materials contained in them by distillation, such as has been practiced for a long time, for example, in the case of used motor oil, proved to be technically impractical and failed in particular because the glycol ether borates boiled over 300 ° C have and also decompose partially in vacuum distillation.
Ein Verfahren zur Wiederaufbereitung verbrauchter Hydraulikflüssigkeiten der vorbezeichneten Art wird in der als älteres Recht in der Bundesrepublik Deutschland eingereichten Patentanmeldung P 39 10 932.1 vorgeschlagen. Die wesentlichen Stufen dieses Verfahrens bestehen in einer alkalischen Hydrolyse der gegebenenfalls vorgereinigten Glykoletherborate durch Erhitzen mit wäßrigen Alkali- und/oder Erdalkalioxiden bzw. - hydroxiden oder -carbonaten und Rückveresterung der aus der Hydrolyse destillativ gewonnenen Glykolether mit Borsäure oder Borsäureanhydrid zu Glykoletherboraten, die als gereinigte Basisprodukte erneut einer Verwendung in Hydraulikflüssigkeiten zugeführt werden können. Das Verfahren ist zwar zur Wiederaufbereitung von verbrauchten Hydraulikflüssigkeiten auf der Basis von Glykoletherboraten geeignet, die wirtschaftliche Durchführung eines solchen Verfahrens wird jedoch durch einen erheblichen Aufwand an Zeit und Energiekosten sowie durch den Umstand beeinträchtigt, daß die Verfahrensbedingungen naturgemäß nicht schonend sind und am Ende des Wiederaufbereitungsverfahrens erhebliche Mengen an nicht weiterverwendbaren Hydrolyserückständen anfallen.A process for the reprocessing of used hydraulic fluids of the aforementioned type is proposed in patent application P 39 10 932.1, which was filed as prior law in the Federal Republic of Germany. The essential stages of this process consist in an alkaline hydrolysis of the optionally prepurified glycol ether borates by heating with aqueous alkali and / or alkaline earth oxides or hydroxides or carbonates and re-esterification of the glycol ethers obtained by hydrolysis with boric acid or boric anhydride to give glycol ether borates, which are purified Basic products can be reused for use in hydraulic fluids. Although the process is suitable for the reprocessing of used hydraulic fluids based on glycol ether borates, the economical implementation of such a process is impaired by a considerable expenditure of time and energy costs and by the fact that the process conditions are naturally not gentle and at the end of the reprocessing process considerable amounts of hydrolysis residues no longer usable arise.
Der Erfindung liegt daher die Aufgabe zugrunde, ein Verfahren zur Aufbereitung gebrauchter Hydraulikflüssigkeiten auf der Basis von Glykolethern mit einem Gehalt an Glykoletherboraten bereitzustellen, das unter schonenden Bedingungen wirtschaftlich vorteilhaft durchführbar ist und eine so weitgehende Reinigung der Glykoletherprodukte ermöglicht, daß diese zur Herstellung von frischen Hydraulikflüssigkeiten für hydraulische Bremsanlagen verwendet werden können.The invention is therefore based on the object of providing a process for the preparation of used hydraulic fluids based on glycol ethers with a content of glycol ether borates which can be carried out economically advantageously under mild conditions and which enables the glycol ether products to be cleaned to such an extent that they produce fresh hydraulic fluids can be used for hydraulic brake systems.
Die gestellte Aufgabe wird erfindungsgemäß dadurch gelöst, daß die aufzubereitende Hydraulikflüssigkeit, gegebenenfalls nach vorheriger Entwässerung, mit einem Überschuß von mindestens 38 Gew.-%, bezogen auf die zur stöchiometrischen Umesterung der Glykoletherborate erforderliche Menge, an einem oder mehreren kurzkettigen aliphatischen Alkoholen bei Normaldruck oder erhöhtem Druck auf eine Temperatur erhitzt wird, bei der eine Umesterung der Glykoletherborate entsprechend der allgemeinen Reaktionsgleichung
Durch die Umesterung werden die unter schonenden Bedingungen nicht destillierbaren Glykoletherborate in Trialkylborate übergeführt, die deutlich niedriger sieden als die in der Hydraulikflüssigkeit vorliegenden und bei der Umesterung gebildeten Glykolether. Sie können deshalb von letzteren ohne Schwierigkeiten abgetrennt werden, vorzugsweise durch Destillation unter Normaldruck oder leicht erhöhtem Druck, beispielsweise von 1,2 bis 10 bar.The transesterification converts the glycol ether borates, which cannot be distilled under mild conditions, to trialkyl borates, which boil significantly lower than the glycol ethers present in the hydraulic fluid and formed during the transesterification. They can therefore be separated from the latter without difficulty, preferably by distillation under normal pressure or slightly elevated pressure, for example from 1.2 to 10 bar.
Das erfindungsgemäße Verfahren kann auf diese Weise unter schonenden Bedingungen durchgeführt werden und liefert neben den durch fraktionierte Destillation gereinigten Glykolethern hochreine Trialkylborate, die entweder durch Rückveresterung mit Glykolethern, insbesondere mit Methyltriglykol, erneut zu Glykoletherboraten umgesetzt und mit einer entsprechenden Menge Glykolether zu einer frischen Hydraulikflüssigkeit vermischt oder in an sich bekannter Weise zu reinen Borsäureestern und/oder reiner Borsäure weiterverarbeitet werden können.The process according to the invention can be carried out in this way under mild conditions and, in addition to the glycol ethers purified by fractional distillation, provides high-purity trialkyl borates, which are reacted to glycol ether borates either by re-esterification with glycol ethers, in particular with methyl triglycol, and mixed with a corresponding amount of glycol ether to form a fresh hydraulic fluid or can be further processed in a manner known per se to pure boric acid esters and / or pure boric acid.
Aufgrund der erfindungsgemäß angewandten schonenden Verfahrensbedingungen verbleibt nach der fraktionierten Destillation lediglich ein nicht weiter verwertbarer Rückstand von etwa 5 bis 8 Gew.- %, bezogen auf die eingesetzte Menge an verbrauchter Hydraulikflüssigkeit.Because of the gentle process conditions used according to the invention, only a residue of about 5 to 8% by weight, based on the amount of hydraulic fluid used, remains after the fractional distillation.
Vorzugsweise werden für die Umesterung als kurzkettige aliphatische Alkohole einwertige Alkohole mit 1 bis 3 C-Atomen eingesetzt. Ganz besonders bevorzugt wird Methanol für die Umesterung eingesetzt.Monohydric alcohols having 1 to 3 carbon atoms are preferably used for the transesterification as short-chain aliphatic alcohols. Methanol is very particularly preferably used for the transesterification.
Die Umesterung der Glykoletherborate erfolgt nach dem erfindungsgemäßen Verfahren mit einem Überschuß von mindestens 38 Gew.-% eines oder mehrerer kurzkettiger aliphatischer Alkohole, bezogen auf die zur stöchiometrischen Umesterung der Glykoletherborate erforderliche Menge, wobei vorzugsweise ein Alkoholüberschuß im Bereich von 38 bis 150 Gew.-%, ganz besonders bevorzugt im Bereich von 38 bis 100 Gew.-% eingesetzt wird.The transesterification of the glycol ether borates is carried out by the process according to the invention with an excess of at least 38% by weight of one or more short-chain aliphatic alcohols, based on the amount required for the stoichiometric transesterification of the glycol ether borates, preferably an alcohol excess in the range from 38 to 150% by weight. %, very particularly preferably in the range from 38 to 100% by weight.
In einer besonders bevorzugten Ausführungsform des erfindungsgemäßen Verfahrens erfolgt die Abtrennung der gebildeten Trialkylborate aus dem Reaktionsgemisch zusammen mit überschüssigem Alkohol durch Destillation, gegebenenfalls als azeotrope Mischung. Besonders bevorzugt ist eine Ausführungsform, bei der die gebildeten Trialkylborate zusammen mit überschüssigem Methanol als Azeotrop bei 54 bis 55 C kontinuierlich unter Normaldruck aus dem Reaktionsgemisch abdestilliert werden. Das Azeotrop weist hierbei eine Zusammensetzung von 73 Gew.-% Borsäureester und 27 Gew.-% Methanol auf.In a particularly preferred embodiment of the process according to the invention, the trialkylborates formed are separated from the reaction mixture together with excess alcohol by distillation, if appropriate as an azeotropic mixture. An embodiment is particularly preferred in which the trialkyl borates formed are distilled off together with excess methanol as an azeotrope at 54 to 55 ° C. under normal pressure continuously from the reaction mixture. The azeotrope has a composition of 73% by weight of boric acid ester and 27% by weight of methanol.
In einer weiteren bevorzugten Ausführungsform des erfindungsgemäßen Verfahrens wird eine azeotrope Mischung aus Trialkylboraten und einem aliphatischen Alkohol zusammen mit Glykolethern und Wasser unter Normaldruck zum Sieden erhitzt, wobei Alkohol und Wasser abdestilliert und die Trialkylborate mit den Glykolethern zu den gewünschten Glykoletherboraten verestert werden.In a further preferred embodiment of the process according to the invention, an azeotropic mixture of trialkyl borates and an aliphatic alcohol together with glycol ethers and water is heated to boiling under atmospheric pressure, alcohol and water being distilled off and the trialkyl borates being esterified with the glycol ethers to give the desired glycol ether borates.
Die wiedergewonnenen Glykoletherfraktionen entsprechen in ihrer Reinheit den Anforderungen, die an Rohstoffe für die Neuherstellung von Bremsflüssigkeiten gestellt werden, insbesondere deshalb, weil durch das erfindungsgemäße Verfahren die thermische Belastung gegenüber einer alkalischen Hydrolyse wesentlich reduziert werden kann.The recovered glycol ether fractions correspond in their purity to the requirements placed on raw materials for the production of new brake fluids, in particular because the process according to the invention can substantially reduce the thermal load compared to alkaline hydrolysis.
Die Erfindung wird nachfolgend anhand von zwei Verfahrensbeispielen weiter erläutert.The invention is explained in more detail below with the aid of two process examples.
1 kg verbrauchte, vorher im Vakuum entwässerte Bremsflüssigkeit, die sich aus 50 Gew.-% Triethylenglykolmonomethylether und 50 Gew.-% Tris(triethylenglykolmonomethylether)borat zusammensetzte und einen Borgehalt von 1,3 % aufwies, wurde mit 170 g Methanol vermischt und die Mischung zum Sieden erhitzt. Das bei der Umesterung entstandene Trimethylborat bildete mit Methanol ein azeotropes Gemisch, das bei 54 bis 55 C kontinuierlich aus der Reaktionsmischung unter Normaldruck abdestillierte. Gegen Ende der Umsetzung wurden überschüssiges Methanol und Reste des Borsäureesters durch Erhöhung der Destillationstemperatur auf 65 C destillativ entfernt. Die aus der ursprünglichen Bremsflüssigkeit stammenden und durch die Umesterung neu gebildeten Glykolether wurden anschließend im Vakuum fraktioniert destilliert.1 kg of used brake fluid, previously dewatered in vacuo, which was composed of 50% by weight of triethylene glycol monomethyl ether and 50% by weight of tris (triethylene glycol monomethyl ether) and had a boron content of 1.3%, was mixed with 170 g of methanol and the mixture heated to boiling. The trimethyl borate formed during the transesterification formed an azeotropic mixture with methanol, which continuously distilled off from the reaction mixture at 54 to 55 ° C. under normal pressure. Towards the end of the reaction, excess methanol and residues of the boric acid ester were removed by distillation by increasing the distillation temperature to 65 ° C. The glycol ethers originating from the original brake fluid and newly formed by the transesterification were then fractionally distilled in vacuo.
Es verblieb ein nicht weiter verarbeitbarer Rückstand von etwa 6 Gew.-%, bezogen auf die eingesetzte Menge an Bremsflüssigkeit.What remained was a residue of about 6% by weight, which could not be processed further, based on the amount of brake fluid used.
Ein Teil des erhaltenen Azeotrops aus Trimethylborat und Methanol wurde mit Borsäure zu einem reinen Borsäureester umgesetzt. Anstelle von Borsäure kann auch Borsäureanhydrid verwendet werden. Ein anderer Teil des erhaltenen Azeotrops aus Trimethylborat und Methanol wurde mit Wasser hydrolytisch zersetzt, wobei das Methanol zurückgewonnen und reine Borsäure erhalten wurde.Part of the azeotrope obtained from trimethyl borate and methanol was reacted with boric acid to give a pure boric acid ester. Instead of boric acid, boric anhydride can also be used. Another part of the azeotrope obtained from trimethyl borate and methanol was washed with Was hydrolytically decomposed, the methanol being recovered and pure boric acid being obtained.
150 g des aus Beispiel 1 gewonnenen Azeotrops wurden mit 550 g Triethylenglykolmonomethylether und 100 ml Wasser zum Sieden erhitzt. Dabei destillierte zunächst Methanol ab, wobei Borsäure aus dem Trimethylborat des Azeotrops freigesetzt wurde. Durch Erhöhung der Destillationstemperatur wurde als nächste Fraktion Wasser abdestilliert, bis die Veresterung des Triethylenglykolmonomethylethers mit Borsäure abgeschlossen war. Die letzten 5 % Wasser wurden unter Ölpumpenvakuum bei einer Sumpftemperatur bis zu 140°C aus der Reaktionsmischung abdestilliert, wobei lediglich ein Restgehalt von weniger als 0,1 Gew.-% Wasser in der Reaktionsmischung verblieb. Es wurde Tris-(triethylenglykolmonomethylether)borat in 100 % Ausbeute erhalten, das sich als Rohstoff für die Herstellung von Hydraulikflüssigkeiten als gut geeignet erwies.150 g of the azeotrope obtained from Example 1 were heated to boiling with 550 g of triethylene glycol monomethyl ether and 100 ml of water. In the process, methanol first distilled off, with boric acid being released from the trimethyl borate of the azeotrope. As the next fraction, water was distilled off by increasing the distillation temperature until the esterification of the triethylene glycol monomethyl ether with boric acid was complete. The last 5% of water were distilled off from the reaction mixture under an oil pump vacuum at a bottom temperature of up to 140 ° C., only a residual content of less than 0.1% by weight of water remaining in the reaction mixture. Tris (triethylene glycol monomethyl ether) borate was obtained in 100% yield, which proved to be a suitable raw material for the production of hydraulic fluids.
Claims (7)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4023579A DE4023579A1 (en) | 1990-07-25 | 1990-07-25 | TREATMENT OF USED HYDRAULIC LIQUIDS ON A GLYCOLETHER AND BORESTER BASE AFTER RESTORING THE GLYCOLETHERBORATES WITH SHORT-CHAIN ALIPATIC ALCOHOLS |
DE4023579 | 1990-07-25 |
Publications (2)
Publication Number | Publication Date |
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EP0468087A1 true EP0468087A1 (en) | 1992-01-29 |
EP0468087B1 EP0468087B1 (en) | 1993-10-20 |
Family
ID=6410964
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90119391A Expired - Lifetime EP0468087B1 (en) | 1990-07-25 | 1990-10-10 | Process for working up used hydraulic fluids containing ethers of glycol as base material and borates of glycol ethers |
Country Status (2)
Country | Link |
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EP (1) | EP0468087B1 (en) |
DE (2) | DE4023579A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4405622A1 (en) * | 1994-02-22 | 1995-08-24 | Basf Ag | Reprocessing hydraulic fluids contg. glycol ether borate(s) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0632126A3 (en) * | 1993-10-25 | 1995-05-17 | Scherle Johann | Process for working up used break and hydraulic fluids. |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2088935A (en) * | 1935-08-14 | 1937-08-03 | Union Carbide & Carbon Corp | Manufacture of alkyl borates |
US4066682A (en) * | 1976-07-06 | 1978-01-03 | Continental Oil Company | Transesterification of borate esters for producing secondary alcohols |
-
1990
- 1990-07-25 DE DE4023579A patent/DE4023579A1/en not_active Withdrawn
- 1990-10-10 EP EP90119391A patent/EP0468087B1/en not_active Expired - Lifetime
- 1990-10-10 DE DE90119391T patent/DE59003164D1/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2088935A (en) * | 1935-08-14 | 1937-08-03 | Union Carbide & Carbon Corp | Manufacture of alkyl borates |
US4066682A (en) * | 1976-07-06 | 1978-01-03 | Continental Oil Company | Transesterification of borate esters for producing secondary alcohols |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4405622A1 (en) * | 1994-02-22 | 1995-08-24 | Basf Ag | Reprocessing hydraulic fluids contg. glycol ether borate(s) |
Also Published As
Publication number | Publication date |
---|---|
DE4023579A1 (en) | 1992-02-20 |
DE59003164D1 (en) | 1993-11-25 |
EP0468087B1 (en) | 1993-10-20 |
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