EP1123263A1 - Processing of contaminated fatty alcohol mixtures - Google Patents
Processing of contaminated fatty alcohol mixturesInfo
- Publication number
- EP1123263A1 EP1123263A1 EP99953786A EP99953786A EP1123263A1 EP 1123263 A1 EP1123263 A1 EP 1123263A1 EP 99953786 A EP99953786 A EP 99953786A EP 99953786 A EP99953786 A EP 99953786A EP 1123263 A1 EP1123263 A1 EP 1123263A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fatty alcohol
- alcohol
- fatty
- alcohol mixtures
- contaminated
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/94—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
Definitions
- the invention relates to a process for working up contaminated fatty alcohol mixtures, in which
- the invention relates to a process for working up contaminated fatty alcohol mixtures, in which
- Fatty alcohols which serve as a further feed component, are to be understood as primary aliphatic alcohols of the formula (I)
- R 1 represents an aliphatic, linear or branched hydrocarbon radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds.
- Typical examples are capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolenyl alcohol, linolyl alcohol, linoleyl alcohol, linoleyl alcohol Technical mixtures which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols.
- acids are used in amounts of 0.1 to 10, preferably 0.5 to 5 and in particular 1% by weight, based on the fatty alcohol.
- Organic acids such as, for example, sulfosuccinic acid or alkylbenzenesulfonic acids are preferably used, the alkyl radical representing 1 to 14, preferably 1 or 12, carbon atoms.
- the use of dodecylbenzenesulfonic acid or p-toluenesulfonic acid is preferred.
- the acid treatment is usually carried out with stirring at pressures from 1 to 200, preferably 20 to 30 mbar and at temperatures from 50 to 120, preferably around 105 ° C.
- the reaction time is usually 30 minutes to 2 hours.
- Existing or formed water is distilled off under the conditions mentioned above.
- the purified fatty alcohol is generally distilled from the residue at a pressure of 1 to 50 mbar, preferably 10 mbar and in a temperature range of 50 to 250, preferably 150 ° C. A residue of 1 to 10% remains in the bladder.
- Glucose was acetalized with technical C. 4 4 coconut fatty alcohol in a molar ratio of 1: 4 and with the addition of 1% by weight of dodecylbenzenesulfonic acid at 112 ° C. and 20 mbar to the alkyl oligoglycocoside.
- the water of condensation was continuously removed from the equilibrium.
- the reaction was complete and the excess fatty alcohol was separated from the reaction product in a combination of a falling film and a thin film evaporator. The fatty alcohol was worked up separately.
- the alcohol separated from the acetalization was, as described in EP 0387912 B1, washed with an aqueous solution of 42% by weight NaOH and 12% by weight sodium borohydride, distilled and then returned to the reaction mixture. When returned to the acetalization, the reaction time increased from 6.5 to 7.5 hours.
- the fatty alcohol separated from the reaction mixture was mixed with 1% by weight of dodecylbenzenesulfonic acid and stirred at 105 ° C. and 30 mbar for 1 hour. The pressure was then reduced to 1 mbar and the temperature increased to 150 ° C., so that the fatty alcohol distilled over into the receiver. A 5% residue remained in the bladder. When returned to the acetalization, the reaction time was reduced from 6.5 to 5.1 hours.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for processing contaminated fatty alcohol mixtures, wherein: (b) the mixture is treated with an acid and (d) the fatty alcohol is then distilled from the residues. One particular advantage is that production costs can be lowered since fatty alcohol mixtures need not be disposed of and the purified fatty alcohol can be reintroduced into the reaction circuit.
Description
Aufarbeitung verunreinigter Fettalkohol-GemischeProcessing contaminated fatty alcohol mixtures
Gebiet der ErfindungField of the Invention
Die Erfindung betrifft ein Verfahren zur Aufarbeitung verunreinigter Fettalkohol-Gemische, bei dem manThe invention relates to a process for working up contaminated fatty alcohol mixtures, in which
(a) das Gemisch mit einer Säure behandelt,(a) treating the mixture with an acid,
(b) und anschließend den Fettalkohol vom Rückstand destilliert.(b) and then distilled the fatty alcohol from the residue.
Stand der TechnikState of the art
In der oleochemischen Industrie stellt die Aufarbeitung verunreinigter Fettalkohole, die aus unterschiedlichen Prozessen stammen können, ein erhebliches Problem dar. Ein Beispiel hierfür ist die Herstellung von Alkyloligoglykosiden aus Glykosen und Fettalkoholen, bei der besonders große Mengen an verunreinigten Fettalkohol-Gemischen anfallen. Aus dem Stand der Technik geht hervor, daß die Fettalkohol-Gemische zur Reinigung mit Basen behandelt und anschließend abdestilliert werden (EP 10387912 B). Diese gereinigten Fettalkohol-Gemische werden in den Kreislauf zurückgeführt und zur Gewinnung weiterer Alkyloligoglykoside eingesetzt. Durch die basische Aufarbeitung können die bei dem Verfahren entstehenden Nebenprodukte nicht beseitigt werden. Außerdem wurde festgestellt, daß die Reaktionszeiten bei der Alkyloligoglykoside - Herstellung deutlich steigen, was auf die Anreicherung dieser Nebenprodukte beim mehrmaligen Einsatz des gleichen Fettalkohol-Gemisches zurückzuführen ist. Durch eine Steigerung der Katalysatormenge können die niedrigen Reaktionszeiten zwar aufrechterhalten werden, der Zusatz an weiterem Katalysator ist jedoch nur begrenzt möglich, da es zu unerwünschten Nebenreaktionen, wie beispielsweise starker Schaumbildung, kommt. Demzufolge müssen zu stark verunreinigte Fettalkohol-Gemische bislang kostenintensiv vernichtet werden. Die Aufgabe der Erfindung bestand somit darin, ein Verfahren zur Aufarbeitung verunreinigter Fettalkohol-Gemische zur Verfügung zu stellen, welches die Fettalkohole quantitativ von den Verunreinigungen trennt.
Beschreibung der ErfindungIn the oleochemical industry, the processing of contaminated fatty alcohols, which can originate from different processes, is a considerable problem. An example of this is the production of alkyl oligoglycosides from glycoses and fatty alcohols, in which particularly large amounts of contaminated fatty alcohol mixtures are obtained. The prior art shows that the fatty alcohol mixtures are treated with bases for cleaning and then distilled off (EP 10387912 B). These purified fatty alcohol mixtures are recycled and used to obtain further alkyl oligoglycosides. The by-products produced in the process cannot be eliminated by the basic work-up. It was also found that the reaction times in alkyl oligoglycoside production increase significantly, which is due to the accumulation of these by-products when the same fatty alcohol mixture is used several times. Although the low reaction times can be maintained by increasing the amount of catalyst, the addition of further catalyst is only possible to a limited extent, since undesirable side reactions, such as excessive foaming, occur. As a result, excessively contaminated fatty alcohol mixtures have so far been costly to destroy. The object of the invention was therefore to provide a process for working up contaminated fatty alcohol mixtures which quantitatively separates the fatty alcohols from the contaminants. Description of the invention
Gegenstand der Erfindung ist ein Verfahren zur Aufarbeitung verunreinigter Fettalkohol-Gemische, bei dem manThe invention relates to a process for working up contaminated fatty alcohol mixtures, in which
(a) das Gemisch mit einer Säure behandelt,(a) treating the mixture with an acid,
(b) und anschließend den Fettalkohol vom Rückstand destilliert.(b) and then distilled the fatty alcohol from the residue.
Überraschenderweise wurde gefunden, daß verunreinigte Fettalkohol-Gemische, wie sie beispielsweise bei der Produktion von Alkyloligoglykosiden anfallen, nahezu vollständig durch Säurebehandlung mit nachfolgender Destillation aufgearbeitet werden können. Bei Rückführung, beispielsweise in die Acetalisierung von Zuckern, werden nicht nur gleiche, sondern teilweise sogar verbesserte Reaktionszeiten als vor der Aufarbeitung erzielt. Dieses ermöglicht eine Verringerung der Herstellungskosten, da der gereinigte Fettalkohol wieder in den Kreislauf zurückgeführt werden kann. Zusätzlich werden Kosten für die Entsorgung der für die Produktion unbrauchbaren Fettalkohol-Gemische eingespart.Surprisingly, it was found that contaminated fatty alcohol mixtures, such as those obtained in the production of alkyl oligoglycosides, can be worked up almost completely by acid treatment with subsequent distillation. In the case of recycling, for example in the acetalization of sugars, not only the same, but sometimes even improved reaction times are achieved than before the workup. This enables the manufacturing costs to be reduced since the purified fatty alcohol can be returned to the cycle. In addition, costs for the disposal of the fatty alcohol mixtures that are unusable for production are saved.
FettalkoholeFatty alcohols
Unter Fettalkoholen, die als weitere Einsatzkomponente dienen, sind primäre aliphatische Alkohole der Formel (I) zu verstehen,Fatty alcohols, which serve as a further feed component, are to be understood as primary aliphatic alcohols of the formula (I)
R1OH (I)R 1 OH (I)
in der R1 für einen aliphatischen, linearen oder verzweigten Kohlenwasserstoffrest mit 6 bis 22 Kohlenstoffatomen und 0 und/oder 1 , 2 oder 3 Doppelbindungen steht. Typische Beispiele sind Capronalkohol, Caprylalkohol, 2-Ethylhexylalkohol, Caprinalkohol, Laurylalkohol, Isotridecylalkohol, Myristylalkohol, Cetylalkohol, Palmoleylalkohol, Stearylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselinylalkohol, Linolylalkohol, Linolenylalkohol, Elaeostearylalkohol, Arachylalkohol, Gadoleylalkohol, Behenylalkohol, Erucylalkohol und Brassidylalkohol sowie deren technische Mischungen, die z.B. bei der Hochdruckhydrierung von technischen Methylestern auf Basis von Fetten und Ölen oder Aldehyden aus der Roelenschen Oxosynthese sowie als Monomerfraktion bei der Dimerisierung von ungesättigten Fettalkoholen anfallen. Bevorzugt sind technische Fettalkohole mit 8 bis 18 Kohlenstoff atomen, wie beispielsweise Kokos-, Palm-, Palmkern- oder Taigfettalkohol.
Säurebehandlunqin which R 1 represents an aliphatic, linear or branched hydrocarbon radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds. Typical examples are capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolenyl alcohol, linolyl alcohol, linoleyl alcohol, linoleyl alcohol Technical mixtures which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols. Technical fatty alcohols with 8 to 18 carbon atoms, such as coconut, palm, palm kernel or tallow fatty alcohol, are preferred. Acid treatment
Zur Behandlung des Fettalkohol-Gemisches werden Säuren in Mengen von 0,1 bis 10, vorzugsweise 0,5 bis 5 und insbesondere 1 Gew.-%, bezogen auf den Fettalkohol, eingesetzt. Vorzugsweise verwendet man organische Säuren wie beispielsweise Sulfobemsteinsäure oder Alkylbenzolsulfonsäuren, wobei der Alkylrest für 1 bis 14, vorzugsweise für 1 oder 12 Kohlenstoffatome steht. Bevozugt ist der Einsatz von Dodecylbenzolsulfonsäure oder p- Toluolsulfonsäure. Die Säurebehandlung erfolgt üblicherweise unter Rühren bei Drücken von 1 bis 200, vorzugsweise 20 bis 30 mbar und bei Temperaturen von 50 bis 120, vorzugsweise um 105 °C. Die Reaktionsdauer beträgt in der Regel 30 min bis 2 Stunden. Vorhandenes oder gebildetes Wasser wird unter den oben genannten Bedingungen abdestilliert.To treat the fatty alcohol mixture, acids are used in amounts of 0.1 to 10, preferably 0.5 to 5 and in particular 1% by weight, based on the fatty alcohol. Organic acids such as, for example, sulfosuccinic acid or alkylbenzenesulfonic acids are preferably used, the alkyl radical representing 1 to 14, preferably 1 or 12, carbon atoms. The use of dodecylbenzenesulfonic acid or p-toluenesulfonic acid is preferred. The acid treatment is usually carried out with stirring at pressures from 1 to 200, preferably 20 to 30 mbar and at temperatures from 50 to 120, preferably around 105 ° C. The reaction time is usually 30 minutes to 2 hours. Existing or formed water is distilled off under the conditions mentioned above.
Destillationdistillation
Nach der Säurebehandlung erfolgt die Destillation des gereinigten Fettalkohols vom Rückstand in der Regel bei einem Druck von 1 bis 50 mbar, vorzugsweise 10 mbar und in einem Temperaturbereich von 50 bis 250, vorzugsweise 150 °C. In der Blase verbleibt ein Rückstand von 1 bis 10 %.
After the acid treatment, the purified fatty alcohol is generally distilled from the residue at a pressure of 1 to 50 mbar, preferably 10 mbar and in a temperature range of 50 to 250, preferably 150 ° C. A residue of 1 to 10% remains in the bladder.
BeispieleExamples
Glucose wurde mit technischem C._.ι4-Kokosfettfalkohol im molaren Verhältnis von 1 : 4 und unter Zusatz von 1 Gew.-% Dodecylbenzolsulfonsäure bei 112 °C und 20 mbar zum Alkyloligoglycokosid acetalisiert. Zur Verlagerung des Reaktion in Richtung der gewünschten Produkte entfernte man kontinuierlich das Kondensationswasser aus dem Gleichgewicht. Nach 6,5 Stunden war die Reaktion beendet, und der im Überschuß zugesetzte Fettalkohol wurde in einer Kombination aus einem Fallfilm- und einem Dünnschichtverdampfer vom Reaktionsprodukt abgetrennt. Die Aufarbeitung des Fettalkohols erfolgte separat.Glucose was acetalized with technical C. 4 4 coconut fatty alcohol in a molar ratio of 1: 4 and with the addition of 1% by weight of dodecylbenzenesulfonic acid at 112 ° C. and 20 mbar to the alkyl oligoglycocoside. In order to shift the reaction towards the desired products, the water of condensation was continuously removed from the equilibrium. After 6.5 hours the reaction was complete and the excess fatty alcohol was separated from the reaction product in a combination of a falling film and a thin film evaporator. The fatty alcohol was worked up separately.
Vergleichsbeispiel V1Comparative Example V1
Der aus der Acetalisierung abgetrennte Alkohol wurde, wie in der EP 0387912 B1 beschrieben, mit einer wäßrigen Lösung aus 42 Gew.-% NaOH und 12 Gew.-% Natriumborhydrid gewaschen, destilliert und anschließend in die Reaktionsmischung zurückgeführt. Bei Rückführung in die Acetalisierung verlängerte sich die Reaktionszeit von 6,5 auf 7,5 Stunden.The alcohol separated from the acetalization was, as described in EP 0387912 B1, washed with an aqueous solution of 42% by weight NaOH and 12% by weight sodium borohydride, distilled and then returned to the reaction mixture. When returned to the acetalization, the reaction time increased from 6.5 to 7.5 hours.
Beispiel 1example 1
Der aus der Reaktionsmischung abgetrennte Fettalkohol wurde mit 1 Gew.-% Dodecylbenzolsulfonsäure versetzt und 1 Stunde bei 105 °C und 30 mbar gerührt. Anschließend wurde der Druck auf 1 mbar reduziert und die Temperatur auf 150 °C gesteigert, so daß der Fettalkohol in die Vorlage überdestillierte. In der Blase verblieb ein Rückstand von 5 %. Bei Rückführung in die Acetalisierung verkürzte sich die Reaktionszeit von 6,5 auf 5,1 Stunden.
The fatty alcohol separated from the reaction mixture was mixed with 1% by weight of dodecylbenzenesulfonic acid and stirred at 105 ° C. and 30 mbar for 1 hour. The pressure was then reduced to 1 mbar and the temperature increased to 150 ° C., so that the fatty alcohol distilled over into the receiver. A 5% residue remained in the bladder. When returned to the acetalization, the reaction time was reduced from 6.5 to 5.1 hours.
Claims
1. Verfahren zur Aufarbeitung verunreinigter Fettalkohol-Gemische, bei dem man (a) das Gemisch mit einer Säure behandelt,1. Process for working up contaminated fatty alcohol mixtures, in which (a) the mixture is treated with an acid,
(c) und anschließend den Fettalkohol vom Rückstand destilliert.(c) and then distilled the fatty alcohol from the residue.
2. Verfahren nach Anspruch 1 , dadurch gekennzeichnet, daß man Fettalkohol-Gemische einsetzt, die bei der Alkyloligoglycosid-Herstellung anfallen.2. The method according to claim 1, characterized in that one uses fatty alcohol mixtures which are obtained in the alkyl oligoglycoside production.
3. Verfahren nach den Ansprüchen 1 und/oder 2, dadurch gekennzeichnet, daß man Fettalkohole der Formel (I) einsetzt,3. Process according to claims 1 and / or 2, characterized in that fatty alcohols of the formula (I) are used,
in der R1 für einen linearen oder verzweigten Kohlenwasserstoffrest mit 6 bis 22 Kohlenstoffatomen und 0 und/oder 1 , 2 oder 3 Doppelbindungen steht.in which R 1 represents a linear or branched hydrocarbon radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds.
4. Verfahren nach mindestens einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß man Fettalkohole der Formel (I) einsetzt, in der R1 für einen linearen Alkylrest mit 8 bis 18 Kohlenstoffatomen steht.4. The method according to at least one of claims 1 to 3, characterized in that fatty alcohols of the formula (I) are used in which R 1 is a linear alkyl radical having 8 to 18 carbon atoms.
5. Verfahren nach mindestens einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß man organische Säuren einsetzt.5. The method according to at least one of claims 1 to 4, characterized in that one uses organic acids.
6. Verfahren nach mindestens einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß man Sulfonsäuren einsetzt.6. The method according to at least one of claims 1 to 5, characterized in that sulfonic acids are used.
7. Verfahren nach mindestens einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, daß man Alkylbenzolsulfonsäuren einsetzt.7. The method according to at least one of claims 1 to 6, characterized in that alkylbenzenesulfonic acids are used.
8. Verfahren nach mindestens einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, daß man 0,1 bis 10 Gew.-% der Säure bezogen auf den Fettalkohol einsetzt.8. The method according to at least one of claims 1 to 7, characterized in that 0.1 to 10 wt .-% of the acid is used based on the fatty alcohol.
9. Verfahren nach mindestens einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, daß man die Behandlung des Fettalkohols mit Säuren bei einem Druck von 1 bis 200 mbar und in einem Temperaturbereich von 50 bis 120 °C durchführt. Verfahren nach mindestens einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, daß man den Fettalkohoi bei einem Druck von 1 bis 50 mbar und in einem Temperaturbereich von 50 bis 250 °C abdestilliert. 9. The method according to at least one of claims 1 to 8, characterized in that one carries out the treatment of the fatty alcohol with acids at a pressure of 1 to 200 mbar and in a temperature range of 50 to 120 ° C. Process according to at least one of Claims 1 to 9, characterized in that the fatty alcohol is distilled off at a pressure of 1 to 50 mbar and in a temperature range of 50 to 250 ° C.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19848548A DE19848548C2 (en) | 1998-10-21 | 1998-10-21 | Process for processing contaminated fatty alcohol mixtures |
| DE19848548 | 1998-10-21 | ||
| PCT/EP1999/007657 WO2000023406A1 (en) | 1998-10-21 | 1999-10-12 | Processing of contaminated fatty alcohol mixtures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1123263A1 true EP1123263A1 (en) | 2001-08-16 |
Family
ID=7885205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP99953786A Withdrawn EP1123263A1 (en) | 1998-10-21 | 1999-10-12 | Processing of contaminated fatty alcohol mixtures |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1123263A1 (en) |
| JP (1) | JP2002527495A (en) |
| KR (1) | KR20010080232A (en) |
| CN (1) | CN1324339A (en) |
| AU (1) | AU1035800A (en) |
| DE (1) | DE19848548C2 (en) |
| WO (1) | WO2000023406A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI2964598T1 (en) * | 2013-03-07 | 2020-12-31 | Genomatica, Inc. | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| EP3743772A1 (en) | 2018-01-25 | 2020-12-02 | Merck Patent GmbH | Photoresist remover compositions |
| CN111690021B (en) * | 2020-06-24 | 2023-03-14 | 江苏万淇生物科技股份有限公司 | Method for removing fatty alcohol in alkyl glycoside |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1113449B (en) * | 1958-05-13 | 1961-09-07 | Union Carbide Corp | Process for the purification of synthetically produced alcohols |
| DE3010510A1 (en) * | 1979-03-23 | 1980-10-02 | Basf Wyandotte Corp | Purifying diol by treatment with sulphonic acid - for prodn. of polyester poly:ol(s) etc. of better colour |
| JPH0684390B2 (en) * | 1989-03-17 | 1994-10-26 | 花王株式会社 | Method for producing alkyl glycoside |
-
1998
- 1998-10-21 DE DE19848548A patent/DE19848548C2/en not_active Expired - Lifetime
-
1999
- 1999-10-12 KR KR1020017004882A patent/KR20010080232A/en not_active Application Discontinuation
- 1999-10-12 EP EP99953786A patent/EP1123263A1/en not_active Withdrawn
- 1999-10-12 AU AU10358/00A patent/AU1035800A/en not_active Abandoned
- 1999-10-12 CN CN99812424A patent/CN1324339A/en active Pending
- 1999-10-12 JP JP2000577135A patent/JP2002527495A/en active Pending
- 1999-10-12 WO PCT/EP1999/007657 patent/WO2000023406A1/en not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO0023406A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1324339A (en) | 2001-11-28 |
| AU1035800A (en) | 2000-05-08 |
| DE19848548C2 (en) | 2001-06-13 |
| KR20010080232A (en) | 2001-08-22 |
| DE19848548A1 (en) | 2000-04-27 |
| JP2002527495A (en) | 2002-08-27 |
| WO2000023406A1 (en) | 2000-04-27 |
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