DE19831705A1 - Preparation of symmetric dialkyl ethers useful e.g. as oil component in cosmetics - Google Patents
Preparation of symmetric dialkyl ethers useful e.g. as oil component in cosmeticsInfo
- Publication number
- DE19831705A1 DE19831705A1 DE19831705A DE19831705A DE19831705A1 DE 19831705 A1 DE19831705 A1 DE 19831705A1 DE 19831705 A DE19831705 A DE 19831705A DE 19831705 A DE19831705 A DE 19831705A DE 19831705 A1 DE19831705 A1 DE 19831705A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dialkyl ethers
- alcohol
- preparation
- cosmetics
- 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- Withdrawn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
- 150000001983 dialkylethers Chemical class 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000002537 cosmetic Substances 0.000 title description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000009833 condensation Methods 0.000 claims abstract description 7
- 230000005494 condensation Effects 0.000 claims abstract description 7
- 150000001298 alcohols Chemical class 0.000 claims abstract description 6
- 239000003426 co-catalyst Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- AGGIJOLULBJGTQ-UHFFFAOYSA-N sulfoacetic acid Chemical compound OC(=O)CS(O)(=O)=O AGGIJOLULBJGTQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000002191 fatty alcohols Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- -1 di-n-octyl ether Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- CFOQKXQWGLAKSK-KTKRTIGZSA-N (13Z)-docosen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCO CFOQKXQWGLAKSK-KTKRTIGZSA-N 0.000 description 1
- DJYWKXYRGAMLRE-QXMHVHEDSA-N (z)-icos-9-en-1-ol Chemical compound CCCCCCCCCC\C=C/CCCCCCCCO DJYWKXYRGAMLRE-QXMHVHEDSA-N 0.000 description 1
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- CFOQKXQWGLAKSK-UHFFFAOYSA-N 13-docosen-1-ol Natural products CCCCCCCCC=CCCCCCCCCCCCCO CFOQKXQWGLAKSK-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von symmetrischen Dialkylethern durch säure katalysierte Kondensation von Fettalkoholen unter Einsatz ausgewählter Co-Katalysatoren.The invention relates to a process for the preparation of symmetrical dialkyl ethers by acid catalyzed condensation of fatty alcohols using selected co-catalysts.
Symmetrische Dialkylether, wie beispielsweise Di-n-octylether werden beispielsweise in kosmetischen Zubereitungen als Ölkomponenten eingesetzt. Zu ihrer Herstellung geht man vorzugsweise von Fettalkoholen aus, die in Gegenwart saurer Katalysatoren, wie beispielsweise Trifluormethansulfon säure, unter Wasserabspaltung kondensiert werden [vgl. DE-A1 195 11 668 (Henkel)]. Problematisch hierbei sind jedoch die langen Reaktionszeiten und der dadurch bedingte Ausbeuteverlust infolge von Olefinbildung.Symmetrical dialkyl ethers, such as di-n-octyl ether, are used, for example, in cosmetics Preparations used as oil components. They are preferably made from Fatty alcohols in the presence of acidic catalysts, such as trifluoromethanesulfone acid, condensed with elimination of water [cf. DE-A1 195 11 668 (Henkel)]. Problematic however, the long reaction times and the resulting loss of yield due to Olefin formation.
Die Aufgabe der vorliegenden Erfindung hat somit darin bestanden, ein neues Verfahren zur Herstellung von hellfarbigen, symmetrischen Dialkylethern zur Verfügung zu stellen, welches sich durch eine signifikante Verringerung der Reaktionszeiten, durch eine Minimierung der Nebenproduktmenge und durch Ausbeuten oberhalb von 90% der Theorie auszeichnet.The object of the present invention was therefore to develop a new method for Production of light colored, symmetrical dialkyl ethers available, which is characterized by a significant reduction in response times by minimizing the amount of by-products and characterized by yields above 90% of theory.
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Dialkylethern der Formel (I),
The invention relates to a process for the preparation of dialkyl ethers of the formula (I),
R1-O-R1 (I)
R 1 -OR 1 (I)
in der R1 für lineare oder verzweigte Alkyl- und/oder Alkenylreste mit 6 bis 22 Kohlenstoffatomen steht,
durch säurekatalysierte Kondensation von Alkoholen der Formel (II),
in which R 1 represents linear or branched alkyl and / or alkenyl radicals having 6 to 22 carbon atoms, by acid-catalyzed condensation of alcohols of the formula (II),
R1OH (II)
R 1 OH (II)
in der R1 die obige Bedeutung hat, welches sich dadurch auszeichnet, daß man als Co-Katalysator Phosphinsäure einsetzt.in which R 1 has the above meaning, which is characterized in that phosphinic acid is used as the cocatalyst.
Überraschenderweise wurde gefunden, daß durch die Mitverwendung von Phosphinsäure die Reak tionszeiten bei der Veretherung von Fettalkoholen zu Dialkylethern um 25 bis 50% verkürzt werden können. Trotz kürzerer Reaktionszeiten werden dabei dennoch Ausbeuten von über 90% erreicht. Ein weiterer Vorteil des neuen Verfahrens besteht darin, daß die Olefinbildung begrenzt wird und die Einsatzmenge insbesondere teurer Katalysatoren wie Trifluormethansulfonsäure durch die deutlich preiswertere Phosphinsäure ersetzt werden kann. Die Erfindung schließt ferner die Erkenntnis mit ein, daß die Reaktionsprodukte besonders hellfarbig sind.Surprisingly, it was found that the reac tion times in the etherification of fatty alcohols to dialkyl ethers can be reduced by 25 to 50% can. Despite shorter reaction times, yields of over 90% are achieved. A Another advantage of the new process is that the olefin formation is limited and the Amount used, in particular, expensive catalysts such as trifluoromethanesulfonic acid through the clearly cheaper phosphinic acid can be replaced. The invention also includes the knowledge that the reaction products are particularly light colored.
Als Ausgangsstoffe für die Herstellung der Dialkylether kommen Fettalkohole in Frage, wie beispiels weise Capronalkohol, Caprylalkohol, 2-Ethylhexylalkohol, Caprinalkohol, Laurylalkohol, Isotridecylalko hol, Myristylalkohol, Cetylalkohol, Palmoleylalkohol, Stearylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselinylalkohol, Linolylalkohol, Linolenylalkohol, Elaeostearylalkohol, Arachylalkohol, Gadoleylalkohol, Behenylalkohol, Erucylalkohol und Brassidylalkohol sowie deren technische Mi schungen. Vorzugsweise setzt man Alkohole der Formel (II) ein, in der R1 für einen linearen Alkylrest mit 6 bis 18, insbesondere 8 bis 18 Kohlenstoffatomen steht.Suitable starting materials for the preparation of the dialkyl ethers are fatty alcohols, such as, for example, capronalcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, elaalol alcohol, oleyl alcohol, oleyl alcohol, oleyl alcohol Elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical mixtures. Alcohols of the formula (II) in which R 1 is a linear alkyl radical having 6 to 18, in particular 8 to 18, carbon atoms are preferably used.
Die Kondensation verläuft in Gegenwart saurer Katalysatoren, wie beispielsweise Schwefelsäure oder organischen Säuren, wie z. B. Methansulfonsäure, p-Toluolsulfonsäure oder Dodecylbenzolsulfonsäure. Vorzugsweise werden jedoch halogenierte Säuren und/oder Sulfonsäuren, wie beispielsweise Tri fluormethansulfonsäure oder Sulfoessigsäure eingesetzt. Die Einsatzmenge der sauren Katalysatoren liegt dabei in der Regel bei 10 ppm bis 5 Gew.-%, vorzugsweise 0,01 bis i Gew.-% - bezogen auf die Einsatzstoffe. The condensation takes place in the presence of acidic catalysts, such as sulfuric acid or organic acids such as B. methanesulfonic acid, p-toluenesulfonic acid or dodecylbenzenesulfonic acid. However, halogenated acids and / or sulfonic acids, such as tri fluoromethanesulfonic acid or sulfoacetic acid used. The amount of acid catalysts used is usually 10 ppm to 5 wt .-%, preferably 0.01 to i wt .-% - based on the Feedstocks.
Üblicherweise beträgt die Einsatzmenge der Phosphinsäure ebenfalls 10 ppm bis 5 Gew.-% und vor zugsweise 0,1 bis 1 Gew.-% - bezogen auf die Einsatzstoffe.The amount of phosphinic acid used is also usually from 10 ppm to 5% by weight and above preferably 0.1 to 1 wt .-% - based on the starting materials.
Die Kondensationsreaktion kann in an sich bekannter Weise in der Siedehitze, d. h. bei Temperaturen im Bereich von 180 bis 220°C durchgeführt werden. Zur Verlagerung des Reaktionsgleichgewichtes auf die Produktseite empfiehlt es sich, das Kondensationswasser über einen Abscheider kontinuierlich zu entfernen. Der Verlauf der Reaktion kann durch Probenentnahme und gaschromatographische Analyse kontinuierlich verfolgt werden. Es hat sich als vorteilhaft erwiesen, die Reaktion bei einer Ausbeute an Dialkylether von 93 bis 95 Gew.-% abzubrechen, da eine weitere Umsetzung des Fettalkohols ab diesem Punkt mehrheitlich zur Bildung unerwünschter Olefine führt. Die Reaktionszeit ist von der Kata lysatormenge abhängig und kann zwischen 0,5 und 5 h liegen. Im Anschluß an die Kondensation wird die Katalysatormischung durch Zugabe einer äquimolaren Menge Base neutralisiert. Der Dialkylether kann dann durch Waschen und Destillation aufgereinigt werden. The condensation reaction can be carried out in a manner known per se at the boiling point, i.e. H. at temperatures in the range of 180 to 220 ° C. To shift the reaction equilibrium to the product side recommends that the condensation water is continuously added via a separator remove. The course of the reaction can be determined by sampling and gas chromatographic analysis be tracked continuously. It has proven advantageous to start the reaction in a yield Abort dialkyl ether from 93 to 95 wt .-%, since a further reaction of the fatty alcohol at this point the majority leads to the formation of undesired olefins. The response time is from the kata amount of analyzer and can be between 0.5 and 5 h. Following the condensation neutralize the catalyst mixture by adding an equimolar amount of base. The dialkyl ether can then be purified by washing and distillation.
In einem 1-l-Vierhalskolben mit Kühler und Wasserabscheider wurden 520,9 g (4 mol) n-Octanol, 0,52 g (0,0035 mol) Trifluormethansulfonsäure und 1,04 g (0,0079 mol) Phosphinsäure (50 Gew.-%ige wäßrige Lösung) vorgelegt und unter Stickstoffabdeckung zum Sieden erhitzt. Ab einer Temperatur von 192°C setzte die Wasserabscheidung ein. In regelmäßigem Abstand wurden Proben entnommen und gaschromatographisch analysiert. In Tabelle 1 sind als Funktion der Reaktionszeit die Wasserabscheidung, sowie die Zunahme an gebildetem Ether, die Abnahme an Alkohol und die Bildung von n-Octen als Nebenprodukt zusammengefaßt. Nach Abschluß der Reaktion wurde der Katalysator durch Zugabe einer äquimolaren Menge Natriumhydroxid neu tralisiert, der rohe Ether mit Wasser gewaschen und durch Destillation gereinigt. Zu Vergleichszwecken wurde Beispiel 1 wiederholt, jedoch auf den Zusatz von Phosphinsäure als Co-Katalysator verzichtet.In a 1 liter four-necked flask with cooler and water separator 520.9 g (4 mol) of n-octanol, 0.52 g (0.0035 mol) of trifluoromethanesulfonic acid and 1.04 g (0.0079 mol) of phosphinic acid (50% by weight aqueous solution) and under nitrogen blanket for Boiling heated. Water separation started at a temperature of 192 ° C. In regular Samples were taken at a distance and analyzed by gas chromatography. In Table 1 are as Function of the reaction time is the water separation, as well as the increase in ether formed Decrease in alcohol and the formation of n-octene as a by-product. After graduation the reaction became new by adding an equimolar amount of sodium hydroxide The raw ether was washed with water and purified by distillation. For comparison purposes Example 1 was repeated, but the addition of phosphinic acid as cocatalyst was omitted.
Beispiel 1 wurde unter Einsatz von 520,9 g (4 mol) n-Octanol, 0,16 g (0,0011 mol) Trifluormethansulfonsäure und 5,21 g (0,039 mol) Phosphinsäure wiederholt.Example 1 was carried out using 520.9 g (4 mol) of n-octanol, 0.16 g (0.0011 mol) Trifluoromethanesulfonic acid and 5.21 g (0.039 mol) of phosphinic acid repeated.
Beispiel 1 wurde unter Einsatz von 520,9 g (4 mol) n-Octanol, 15,6 g (0,111 mol) Sulfoessigsäure und 1,04 g (0,0079 mol) Phosphinsäure wiederholt.Example 1 was carried out using 520.9 g (4 mol) of n-octanol, 15.6 g (0.111 mol) Repeated sulfoacetic acid and 1.04 g (0.0079 mol) of phosphinic acid.
Beispiel 1 wurde unter Einsatz von 608,6 g (2,25 mol) Stearylalkohol, 0,608 g (0,004 mol) Trifluormethansulfonsäure und 0,61 g (0,009 mol) Phosphinsäure wiederholt. Ab einer Temperatur von 219 'C setzte die Wasserabscheidung ein. Zu Vergleichszwecken wurde Beispiel 4 wiederholt, jedoch auf den Zusatz von Phosphinsäure als Co-Katalysator verzichtet. Example 1 was made using 608.6 g (2.25 mol) Stearyl alcohol, 0.608 g (0.004 mol) trifluoromethanesulfonic acid and 0.61 g (0.009 mol) phosphinic acid repeated. Water separation started at a temperature of 219 ° C. For comparison purposes Example 4 was repeated, but the addition of phosphinic acid as cocatalyst was omitted.
Claims (6)
R1-O-R1 (I)
in der R1 für lineare oder verzweigte Alkyl- und/oder Alkenylreste mit 6 bis 22 Kohlenstoffatomen steht, durch säurekatalysierte Kondensation von Alkoholen der Formel (II),
R1OH (II)
in der R1 die obige Bedeutung hat, dadurch gekennzeichnet, daß man als Co-Katalysator Phosphinsäure einsetzt.1. Process for the preparation of dialkyl ethers of the formula (I),
R 1 -OR 1 (I)
in which R 1 represents linear or branched alkyl and / or alkenyl radicals having 6 to 22 carbon atoms, by acid-catalyzed condensation of alcohols of the formula (II),
R 1 OH (II)
in which R 1 has the above meaning, characterized in that phosphinic acid is used as co-catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19831705A DE19831705A1 (en) | 1997-09-15 | 1998-07-15 | Preparation of symmetric dialkyl ethers useful e.g. as oil component in cosmetics |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19740451 | 1997-09-15 | ||
| DE19831705A DE19831705A1 (en) | 1997-09-15 | 1998-07-15 | Preparation of symmetric dialkyl ethers useful e.g. as oil component in cosmetics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19831705A1 true DE19831705A1 (en) | 1999-03-18 |
Family
ID=7842349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19831705A Withdrawn DE19831705A1 (en) | 1997-09-15 | 1998-07-15 | Preparation of symmetric dialkyl ethers useful e.g. as oil component in cosmetics |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE19831705A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19943585A1 (en) * | 1999-09-11 | 2001-03-15 | Cognis Deutschland Gmbh | Oil body mixture obtained by partial etherification of higher alcohol by acid-catalyzed condensation and esterification of remaining alcohol with carboxylic acid, is used in cosmetic or pharmaceutical compositions |
| EP1695686A1 (en) | 2001-07-13 | 2006-08-30 | Cognis IP Management GmbH | Wax based composition and use as personal care article |
| US7799333B2 (en) | 2001-07-27 | 2010-09-21 | Cognis Ip Management Gmbh | Emulsifier mixture containing fatty alcohols, ethoxylated fatty alcohols and oil and wax components |
| US8658812B2 (en) | 2003-01-08 | 2014-02-25 | Cognis Ip Management Gmbh | Wax dispersions |
-
1998
- 1998-07-15 DE DE19831705A patent/DE19831705A1/en not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19943585A1 (en) * | 1999-09-11 | 2001-03-15 | Cognis Deutschland Gmbh | Oil body mixture obtained by partial etherification of higher alcohol by acid-catalyzed condensation and esterification of remaining alcohol with carboxylic acid, is used in cosmetic or pharmaceutical compositions |
| DE19943585B4 (en) * | 1999-09-11 | 2004-08-12 | Cognis Deutschland Gmbh & Co. Kg | Oil body mixture |
| EP1695686A1 (en) | 2001-07-13 | 2006-08-30 | Cognis IP Management GmbH | Wax based composition and use as personal care article |
| US8716336B2 (en) | 2001-07-13 | 2014-05-06 | Cognis Ip Management Gmbh | Smooth-feeling wax-based compositions for personal care preparations |
| US7799333B2 (en) | 2001-07-27 | 2010-09-21 | Cognis Ip Management Gmbh | Emulsifier mixture containing fatty alcohols, ethoxylated fatty alcohols and oil and wax components |
| US8658812B2 (en) | 2003-01-08 | 2014-02-25 | Cognis Ip Management Gmbh | Wax dispersions |
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