EP0642651B1 - Process for dehydrating finely divided solid suspensions - Google Patents
Process for dehydrating finely divided solid suspensions Download PDFInfo
- Publication number
- EP0642651B1 EP0642651B1 EP93912772A EP93912772A EP0642651B1 EP 0642651 B1 EP0642651 B1 EP 0642651B1 EP 93912772 A EP93912772 A EP 93912772A EP 93912772 A EP93912772 A EP 93912772A EP 0642651 B1 EP0642651 B1 EP 0642651B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dialkyl carbonates
- suspensions
- auxiliaries
- dewatering
- 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 - Lifetime
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Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F26—DRYING
- F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
- F26B5/00—Drying solid materials or objects by processes not involving the application of heat
- F26B5/005—Drying solid materials or objects by processes not involving the application of heat by dipping them into or mixing them with a chemical liquid, e.g. organic; chemical, e.g. organic, dewatering aids
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S210/00—Liquid purification or separation
- Y10S210/928—Paper mill waste, e.g. white water, black liquor treated
Definitions
- the invention relates to a process for dewatering finely divided solid dispersions, in which dialkyl carbonates are used as auxiliaries.
- suspensions are suitable as auxiliaries for the dewatering of water-containing fine-particle solid suspensions, in particular iron ore concentrates, quartz sands or hard coal, by means of which the residual moisture can be reduced.
- Dialkylsulfosuccinates [US Pat. No. 2,266,954 ] and nonionic surfactants of the fatty alcohol polyglycol ether type [Erzmetall 30, 292 (1977)] have been described, for example, as surfactant dewatering aids of the type mentioned above.
- these surfactants have the disadvantage of considerable foam formation, which leads to considerable problems in the processing plants, in particular when water is circulated in the usual way.
- German published patent application DE-A1-39 18 274 discloses alkyl-end group-capped ⁇ -hydroxyalkyl ethers, so-called hydroxy mixed ethers, which are prepared by ring opening of alpha-olefin epoxides with fatty alcohol ethoxylates and are used as low-foaming auxiliaries in the dewatering of solid suspensions. Although good results are obtained with these agents in solids dewatering, they have the disadvantage of unsatisfactory cold behavior. Particularly when stored outdoors, crystals can form at temperatures of 10 to 15 ° C, which significantly impairs the pumping and flow behavior of these products and thus their intended use.
- EP-A-0 444 760 discloses a drainage agent which releases a polyethylene carbonate of the following structural formula: where R3 is an ackyl radical with 7 to 16 carbon atoms and q is a number from 7 to 16.
- the object of the invention was therefore to provide a process for the dewatering of solid suspensions which is free from the disadvantages described.
- dialkyl carbonates to be used according to the invention have a significantly better foaming and cooling behavior, in particular lower pour points, with comparably good, e.g. T. even have slightly improved application properties.
- Dialkyl carbonates are known substances which can be obtained by the relevant methods of preparative organic chemistry. For their preparation, it is possible, for example, to start from dimethyl carbonate, but preferably diethyl carbonate, and subject them to a transesterification with an appropriate alcohol or alcohol ethoxylate in the presence of basic catalysts [ see. Houben-Weyl, Methods of Organic Chemistry, 4. Ed., Vol.E4, p.66ff].
- Suitable dialkyl carbonates for the purposes of the invention are, for example, mono- and di-transesterification products of dimethyl carbonate and in particular diethyl carbonate with saturated and / or unsaturated primary alcohols with 6 to 22 carbon atoms and their adducts with 1 to 10 moles of ethylene oxide.
- dialkyl carbonates of the formula (I) are preferred in which R 1 is alkyl radicals having 8 to 18 carbon atoms, R is alkyl radicals having 2 or 8 to 18 carbon atoms and n and m are 0 or numbers from 2 to 7 stand.
- Dialkyl carbonates which have a short and a long alkyl group for example mono-transesterification products of diethyl carbonate, have proven to be particularly advantageous.
- the dialkyl carbonates of the formula (I) must be water-dispersible. It is possible that there is no satisfactory water dispersibility in cases in which low values of the degree of ethoxylation are opposed by n or m long-chain radicals R 1 and / or R. However, the required water dispersibility can be easily achieved by using the Value for n or m increased within the above range.
- dialkyl carbonates to be used according to the invention can be used individually; for the dewatering of certain solids, however, it can be advantageous to combine products of different chain lengths or different degrees of ethoxylation with one another in order to exploit synergies in their physicochemical properties. In the same way, it can be advantageous to use the internal hydroxy mixed ethers in combination with other known ionic and / or nonionic drainage aids.
- dialkyl carbonates to be used according to the invention support the dewatering of solid suspensions, are readily biodegradable, have little foam and are characterized by low pour points. They are therefore suitable for dewatering suspensions of various solids, such as iron ore concentrates, quartz sand, hard coal or coke. Another important area of application is the use of the dialkyl carbonates to be used according to the invention as aids in the dewatering of solid suspensions which are used in waste paper processing, e.g. B. in the deinking process or filler flotation.
- the dialkyl carbonates are used in amounts of 10 to 500, preferably 100 to 400 and in particular 150 to 350 g, based on solids content, per ton of solid.
- DAC Dialkyl carbonates
- composition DAC R1 n R m A1 n-C8 2nd n-C8 2nd A2 n-C8 4th n-C8 4th A3 n-C8 4th C2 0 A4 nC 12/14 2nd nC 12/14 2nd A5 nC 12/14 4th nC 12/14 4th A6 nC 12/18 2nd nC 12/18 2nd A7 nC 12/18 7 nC 12/18 7 A8 i-C13 3rd i-C13 3rd A9 nC 16/18 5 nC 16/18 5 A10 nC 16/18 * 5 nC 16/18 * 5 nC 16/18 * 5 nC 16/18 * 5
- the tests were carried out in a cup centrifuge, with which centrifuge parameters from 15 to 2000 can be achieved.
- Perforated plates with sieve openings of 0.1 x 2 mm were used as the sieve covering.
- the drainage aids were used in aqueous solutions; all concentration data are based on the solids content of these solutions.
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
Die Erfindung betrifft ein Verfahren zur Entwässerung feinteiliger Feststoffdispersionen, bei dem man Dialkylcarbonate als Hilfsmittel einsetzt.The invention relates to a process for dewatering finely divided solid dispersions, in which dialkyl carbonates are used as auxiliaries.
In zahlreichen Industriezweigen, z.B. im Bergbau oder in Klärwerken, fallen große Mengen an stark wasserhaltigen, feinteiligen Feststoffen an, die vor der Weiterverarbeitung oder Deponierung entwässert werden müssen. So ist z.B. die Entwässerung von Steinkohle bzw. Koks ein zentraler Prozeß innerhalb der Aufbereitung von Brennstoffen auf Kohlebasis. Dabei können die vom Markt geforderten oberen Grenzwerte für den Wassergehalt dieser Materialien oft nur schwer eingehalten werden, da z.B. geförderte Steinkohle aufgrund der weitgehenden Mechanisierung des untertägigen Kohleabbaus sehr feinkörnig anfällt. Zur Zeit bestehen etwa 38 % der Rohförderung aus Feinkohle mit einem Teilchendurchmesser im Bereich von 0,5 bis 10 mm; weitere 14 % bestehen aus Feinstkohle mit einem darunter liegenden Teilchendurchmesser.In numerous branches of industry, for example in mining or sewage treatment plants, large amounts of highly water-containing, fine-particle solids are produced, which have to be dewatered before further processing or landfilling. For example, the drainage of hard coal or coke is a central process in the processing of coal-based fuels. The upper limit values for the water content of these materials required by the market are often difficult to adhere to, since hard coal, for example, is very fine-grained due to the extensive mechanization of underground coal mining. Around 38% of the raw production currently consists of fine coal with a particle diameter in the range from 0.5 to 10 mm; a further 14% consist of fine coal with an underlying particle diameter.
Es ist bekannt, daß als Hilfsmittel zur Entwässerung von wasserhaltigen feinteiligen Feststoff suspensionen, insbesondere Eisenerzkonzentraten, Quarzsanden oder Steinkohlen, durch die die Restfeuchte herabgesetzt werden kann, manche Tenside geeignet sind. Als tensidische Entwässerungshilfsmittel der vorstehend genannten Art sind beispielsweise Dialkylsulfosuccinate [US-A-2 266 954] und nichtionische Tenside vom Typ der Fettalkoholpolyglycolether [Erzmetall 30, 292 (1977)] beschrieben worden. Diese Tenside sind jedoch mit dem Nachteil einer erheblichen Schaumbildung behaftet, die insbesondere bei der üblicherweise angewendeten Kreislaufführung des Wassers in den Aufbereitungsbetrieben zu erheblichen Problemen führt.It is known that suspensions are suitable as auxiliaries for the dewatering of water-containing fine-particle solid suspensions, in particular iron ore concentrates, quartz sands or hard coal, by means of which the residual moisture can be reduced. Dialkylsulfosuccinates [US Pat. No. 2,266,954 ] and nonionic surfactants of the fatty alcohol polyglycol ether type [Erzmetall 30, 292 (1977)] have been described, for example, as surfactant dewatering aids of the type mentioned above. However, these surfactants have the disadvantage of considerable foam formation, which leads to considerable problems in the processing plants, in particular when water is circulated in the usual way.
Aus der Deutschen Offenlegungsschrift DE-A1-39 18 274 (Henkel) sind alkyl-endgruppenverschlossene β-Hydroxyalkylether, sogenannte Hydroxymischether, bekannt, die durch Ringöffnung von alpha-Olefinepoxiden mit Fettalkoholethoxylaten hergestellt und als schaumarme Hilfsmittel in der Entwässerung von Feststoffsuspensionen eingesetzt werden. Obschon mit diesen Mitteln in der Feststoffentwässerung gute Ergebnisse erzielt werden, weisen sie den Nachteil eines unbefriedigenden Kälteverhaltens auf. Insbesondere bei Außenlagerung kann es schon bei Temperaturen von 10 bis 15°C zur Bildung von Kristallen kommen, wodurch das Pump- und Fließverhalten dieser Produkte und damit ihre bestimmungsgemäße Verwendung erheblich beeinträchtigt wird. Die EP-A-0 444 760 offenbart ein Entwässerungsmittel, das ein Polyethylencarbonat der folgenden struktur formel entlicht :
Die Aufgabe der Erfindung bestand somit darin, ein Verfahren zur Entwässerung von Feststoffsuspensionen zur Verfügang zu stellen, das frei von den geschilderten Nachteilen ist.The object of the invention was therefore to provide a process for the dewatering of solid suspensions which is free from the disadvantages described.
Gegenstand der Erfindung ist ein Verfahren zur Entwässerung von feinteiligen Feststoffsuspensionen, bei dem man als Hilfsmittel Dialkylcarbonate der Formel (I) einsetzt,
- R¹ und R
- unabhängig voneinander für Alkyl- und/oder Alkenylreste mit 1 bis 22 Kohlenstoffatome und
- m und n
- unabhängig voneinander für 0 oder Zahlen von 1 bis 10
- R¹ and R
- independently of one another for alkyl and / or alkenyl radicals having 1 to 22 carbon atoms and
- m and n
- independently for 0 or numbers from 1 to 10
Überraschenderweise wurde gefunden, daß die erfindungsgemäß zu verwendenden Dialkylcarbonate gegenüber den Hilfsmitteln des Stands der Technik ein deutlich besseres Schaum- und Kälteverhalten, insbesondere niedrigere Stockpunkte, bei vergleichbar guten, z. T. sogar leicht verbesserten anwendungstechnischen Eigenschaften aufweisen.Surprisingly, it was found that the dialkyl carbonates to be used according to the invention have a significantly better foaming and cooling behavior, in particular lower pour points, with comparably good, e.g. T. even have slightly improved application properties.
Dialkylcarbonate stellen bekannte Stoffe dar, die nach den einschlägigen Methoden der präparativen organischen Chemie erhalten werden können, Zu ihrer Herstellung kann man beispielsweise von Dimethyl-, vorzugsweise aber Diethylcarbonat ausgehen und dieses einer Umesterung mit einem entsprechenden Alkohol bzw. Alkoholethoxylat in Gegenwart basischer Katalysatoren unterwerfen [vgl. Houben-Weyl, Methoden der Organischen Chemie, 4 . Aufl., Bd.E4, s.66ff]. Dialkyl carbonates are known substances which can be obtained by the relevant methods of preparative organic chemistry. For their preparation, it is possible, for example, to start from dimethyl carbonate, but preferably diethyl carbonate, and subject them to a transesterification with an appropriate alcohol or alcohol ethoxylate in the presence of basic catalysts [ see. Houben-Weyl, Methods of Organic Chemistry, 4. Ed., Vol.E4, p.66ff].
Als Dialkylcarbonate, die im Sinne der Erfindung eingesetzt werden können, kommen beispielsweise Mono- und Di-Umesterungsprodukte von Dimethylcarbonat und insbesondere Diethylcarbonat mit gesättigten und/oder ungesättigten primären Alkoholen mit 6 bis 22 Kohlenstoffatomen sowie deren Addukte mit 1 bis 10 Mol Ethylenoxid in Betracht. Im Hinblick auf geringe Schaumentwicklung und niedrige Stockpunkte sind Dialkylcarbonate der Formel (I) bevorzugt, in der R¹ für Alkylreste mit 8 bis 18 Kohlenstoffatome, R für Alkylreste mit 2 oder 8 bis 18 Kohlenstoffatomen und n und m für 0 oder Zahlen von 2 bis 7 stehen. Als besonders vorteilhaft haben sich solche Dialkylcarbonate erwiesen, die über eine kurze und eine lange Alkylgruppe verfügen, beispielsweise Mono-Umesterungsprodukte des Diethylcarbonats.Suitable dialkyl carbonates for the purposes of the invention are, for example, mono- and di-transesterification products of dimethyl carbonate and in particular diethyl carbonate with saturated and / or unsaturated primary alcohols with 6 to 22 carbon atoms and their adducts with 1 to 10 moles of ethylene oxide. In view of low foaming and low pour points, dialkyl carbonates of the formula (I) are preferred in which R 1 is alkyl radicals having 8 to 18 carbon atoms, R is alkyl radicals having 2 or 8 to 18 carbon atoms and n and m are 0 or numbers from 2 to 7 stand. Dialkyl carbonates which have a short and a long alkyl group, for example mono-transesterification products of diethyl carbonate, have proven to be particularly advantageous.
Entsprechend ihrer erfindungsgemäßen Verwendung müssen die Dialkylcarbonate der Formel (I) wasserdispergierbar sein. Es ist möglich, daß eine befriedigende Wasserdispergierbarkeit in den Fällen nicht gegeben ist, in denen niedrigen Werten des Ethoxylierungsgrades n bzw. m langkettige Reste R¹ und/ oder R gegenüberstehen. Die geforderte Wasserdispergierbarkeit läßt sich jedoch problemlos erreichen, indem man den Wert für n bzw. m innerhalb des vorstehend genannten Bereiches erhöht.According to their use according to the invention, the dialkyl carbonates of the formula (I) must be water-dispersible. It is possible that there is no satisfactory water dispersibility in cases in which low values of the degree of ethoxylation are opposed by n or m long-chain radicals R 1 and / or R. However, the required water dispersibility can be easily achieved by using the Value for n or m increased within the above range.
Die erfindungsgemäß zu verwendenden Dialkylcarbonate können einzeln eingesetzt werden; für die Entwässerung bestimmter Feststoffe kann es jedoch vorteilhaft sein, Produkte unterschiedlicher Kettenlänge bzw. unterschiedlichen Ethoxylierungsgrades miteinander zu kombinieren, um Synergien ihrer physikochemischen Eigenschaften auszunutzen. In gleicher Weise kann es vorteilhaft sein, die innenständigen Hydroxymischether in Kombination mit weiteren bekannten ionischen und/oder nichtionischen Entwässerungshilfsmitteln einzusetzen.The dialkyl carbonates to be used according to the invention can be used individually; for the dewatering of certain solids, however, it can be advantageous to combine products of different chain lengths or different degrees of ethoxylation with one another in order to exploit synergies in their physicochemical properties. In the same way, it can be advantageous to use the internal hydroxy mixed ethers in combination with other known ionic and / or nonionic drainage aids.
Die erfindungsgemäß einzusetzenden Dialkylcarbonate unterstützen die Entwässerung von Feststoffsuspensionen, sind biologisch leicht abbaubar, schaumarm und zeichnen sich durch niedrige Stockpunkte aus. Sie eignen sich daher zur Entwässerung von Suspensionen verschiedenster Feststoffe, wie beispielsweise Eisenerzkonzentrate, Quarzsand, Steinkohle oder Koks. Ein weiteres wichtiges Einsatzgebiet stellt die Verwendung der erfindungsgemäß einzusetzenden Dialkylcarbonate als Hilfsmittel bei der Entwässerung von Feststoffsuspensionen dar, die bei der Altpapieraufbereitung, z. B. beim Deinking-Prozeß oder der Füllstoffflotation anfallen.The dialkyl carbonates to be used according to the invention support the dewatering of solid suspensions, are readily biodegradable, have little foam and are characterized by low pour points. They are therefore suitable for dewatering suspensions of various solids, such as iron ore concentrates, quartz sand, hard coal or coke. Another important area of application is the use of the dialkyl carbonates to be used according to the invention as aids in the dewatering of solid suspensions which are used in waste paper processing, e.g. B. in the deinking process or filler flotation.
Gemäß einer vorteilhaften Ausführungsform des erfindungsgemäßen Verfahrens setzt man die Dialkylcarbonate in Mengen von 10 bis 500, vorzugsweise 100 bis 400 und insbesondere 150 bis 350 g - bezogen auf Feststoffgehalt - pro Tonne Feststoff ein.According to an advantageous embodiment of the process according to the invention, the dialkyl carbonates are used in amounts of 10 to 500, preferably 100 to 400 and in particular 150 to 350 g, based on solids content, per ton of solid.
Die folgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn darauf einzuschränken.The following examples are intended to explain the subject matter of the invention in more detail without restricting it.
A9 wurde auf Basis eines technischen, gesättigten C16/18-Talgfettalkohols (Lorol(R) T, Iodzahl < 5, Fa.Henkel KGaA, Düsseldorf, FRG), A10 auf Basis eines technischen, ungesättigten Fettalkohols gleicher Kettenlänge (HD-Ocenol(R) 50/55, Iodzahl = 52, Fa.Henkel KGaA, Düsseldorf, FRG) hergestellt.A9 was based on a technical, saturated C 16/18 tallow fatty alcohol (Lorol (R) T, iodine number <5, Fa.Henkel KGaA, Düsseldorf, FRG), A10 on the basis of a technical, unsaturated fatty alcohol of the same chain length (HD-ocenol ( R) 50/55, iodine number = 52, manufactured by Henkel KGaA, Düsseldorf, FRG).
Für die Entwässerungsversuche wurde Quarzsand der folgenden Körnung verwendet:
- < 125 µm : 2,8 Gew.-%
- 125 bis 200 µm : 26,4 Gew.-%
- 200 bis 315 µm : 60,1 Gew.-%
- > 315 µm : 10,7 Gew.-%
- <125 µm: 2.8% by weight
- 125 to 200 µm: 26.4% by weight
- 200 to 315 µm: 60.1% by weight
- > 315 µm: 10.7% by weight
Durchgeführt wurden die Versuche in einer Becherzentrifuge, mit der Zentrifugenkennwerte von 15 bis 2000 realisierbar sind. Als Siebbelag wurden Lochplatten mit Sieböffnungen von 0,1 x 2 mm verwendet. Die Entwässerungshilfsmittel wurden in wäßrigen Lösungen eingesetzt; alle Konzentrationsangaben verstehen sich bezogen auf den Feststoffgehalt dieser Lösungen.The tests were carried out in a cup centrifuge, with which centrifuge parameters from 15 to 2000 can be achieved. Perforated plates with sieve openings of 0.1 x 2 mm were used as the sieve covering. The drainage aids were used in aqueous solutions; all concentration data are based on the solids content of these solutions.
Nach Einwaage des Quarzsandes in die Zentrifugenbecher wurden die wäßrigen Lösungen der Entwässerungshilfsmittel zugegeben und gleichmäßig verteilt. Nach einer Abtropfzeit von 1 min wurde der Feststoff über einen Zeitraum von 30 s bei einer Drehzahl von 500 Upm entwässert. Anschließend wurden die feuchten Feststoffe ausgewogen, bei 100°C bis zur Gewichtskonstanz getrocknet und die Restfeuchte in %-rel. bestimmt. Alle Versuchsergebnisse stellen Mittel von Doppelbestimmungen dar. Die Ergebnisse sind in Tab.2 zusammengefaßt.
Claims (5)
- A process for dewatering fine-particle solids suspensions, in which dialkyl carbonates corresponding to formula (I):
- A process as claimed in claim 1, characterized in that dialkyl carbonates corresponding to formula (I), in which R¹ represents C₈₋₁₈ alkyl groups, R represents C₂ or C₈₋₁₈ alkyl groups and n and m stand for 0 or numbers of 2 to 7, are used.
- A process as claimed in claim 1, characterized in that suspensions of iron ore concentrates, quartz sand, coal or coke are dewatered.
- A process as claimed in claim 1, characterized in that the dialkyl carbonates are used in quantities of 10 to 500 g per tonne of solids.
- The use of dialkyl carbonates corresponding to formula (I) as auxiliaries in the dewatering of fine-particle solids suspensions, particularly in the recycling of wastepaper.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4218074A DE4218074A1 (en) | 1992-06-01 | 1992-06-01 | Process for dewatering fine particulate suspensions |
| DE4218074 | 1992-06-01 | ||
| PCT/EP1993/001298 WO1993024799A1 (en) | 1992-06-01 | 1993-05-24 | Process for dehydrating finely divided solid suspensions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0642651A1 EP0642651A1 (en) | 1995-03-15 |
| EP0642651B1 true EP0642651B1 (en) | 1996-02-14 |
Family
ID=6460165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP93912772A Expired - Lifetime EP0642651B1 (en) | 1992-06-01 | 1993-05-24 | Process for dehydrating finely divided solid suspensions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5492631A (en) |
| EP (1) | EP0642651B1 (en) |
| CA (1) | CA2137139A1 (en) |
| DE (2) | DE4218074A1 (en) |
| FI (1) | FI945644A0 (en) |
| WO (1) | WO1993024799A1 (en) |
| ZA (1) | ZA933798B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5777178A (en) * | 1996-12-18 | 1998-07-07 | Olin Corporation | Process for the preparation of polyoxyalkylene ether surfactant compositions |
| US6375853B1 (en) * | 2000-03-17 | 2002-04-23 | Roe-Hoan Yoon | Methods of using modified natural products as dewatering aids for fine particles |
| DE102007027372A1 (en) * | 2007-06-11 | 2008-12-18 | Cognis Oleochemicals Gmbh | Process for the hydrogenation of glycerol |
| DE102007027371A1 (en) * | 2007-06-11 | 2008-12-18 | Cognis Oleochemicals Gmbh | A process for preparing a compound having at least one ester group |
| CN102596350B (en) | 2009-09-15 | 2015-07-29 | 顺科能源公司 | Dry method is carried out to the thin mine tailing of oil-sand slaking |
| CA2701317C (en) | 2009-09-15 | 2016-08-23 | Suncor Energy Inc. | Process for flocculating and dewatering oil sand mature fine tailings |
| CA2735330C (en) | 2009-10-30 | 2015-06-02 | Suncor Energy Inc. | Depositing and farming methods for drying fine tailings |
| PL3116314T3 (en) * | 2014-03-12 | 2021-11-22 | Basf Se | Carbonates of alcohol alkoxylates as adjuvants for crop protection |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2266954A (en) * | 1939-08-26 | 1941-12-23 | American Cyanamid Co | Wetting agent in settling of oe pulps |
| US4098686A (en) * | 1976-03-19 | 1978-07-04 | Vojislav Petrovich | Froth flotation method for recovering of minerals |
| DE3723323C2 (en) * | 1987-07-15 | 1998-03-12 | Henkel Kgaa | Hydroxy mixed ethers, processes for their preparation and their use |
| EP0417358A1 (en) * | 1989-09-12 | 1991-03-20 | Du Pont-Mitsui Fluorochemicals Co., Ltd | Solvent composition for dehydration |
| DE3918274A1 (en) * | 1989-06-05 | 1990-12-06 | Henkel Kgaa | USE OF HYDROXYMISCHETHERS AS A SOLVENT FOR SOLIDS HEATING |
| US5229017A (en) * | 1990-03-01 | 1993-07-20 | Dowell Schlumberger Incorporated | Method of enhancing methane production from coal seams by dewatering |
-
1992
- 1992-06-01 DE DE4218074A patent/DE4218074A1/en not_active Withdrawn
-
1993
- 1993-05-24 WO PCT/EP1993/001298 patent/WO1993024799A1/en not_active Ceased
- 1993-05-24 FI FI945644A patent/FI945644A0/en unknown
- 1993-05-24 EP EP93912772A patent/EP0642651B1/en not_active Expired - Lifetime
- 1993-05-24 CA CA002137139A patent/CA2137139A1/en not_active Abandoned
- 1993-05-24 DE DE59301648T patent/DE59301648D1/en not_active Expired - Fee Related
- 1993-05-28 ZA ZA933798A patent/ZA933798B/en unknown
-
1994
- 1994-12-01 US US08/343,590 patent/US5492631A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE4218074A1 (en) | 1993-12-02 |
| EP0642651A1 (en) | 1995-03-15 |
| WO1993024799A1 (en) | 1993-12-09 |
| FI945644L (en) | 1994-11-30 |
| CA2137139A1 (en) | 1993-12-02 |
| FI945644A7 (en) | 1994-11-30 |
| ZA933798B (en) | 1993-12-22 |
| DE59301648D1 (en) | 1996-03-28 |
| FI945644A0 (en) | 1994-11-30 |
| US5492631A (en) | 1996-02-20 |
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