DD249384A3 - METHOD FOR PRODUCING FLUORAROMATIC NON-ATIONOGENIC BORDER-ACTIVE SUBSTANCES - Google Patents
METHOD FOR PRODUCING FLUORAROMATIC NON-ATIONOGENIC BORDER-ACTIVE SUBSTANCES Download PDFInfo
- Publication number
- DD249384A3 DD249384A3 DD27520185A DD27520185A DD249384A3 DD 249384 A3 DD249384 A3 DD 249384A3 DD 27520185 A DD27520185 A DD 27520185A DD 27520185 A DD27520185 A DD 27520185A DD 249384 A3 DD249384 A3 DD 249384A3
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- och
- active substances
- fluoroaromatic
- oxide adducts
- compounds
- Prior art date
Links
- 239000013543 active substance Substances 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 4
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- -1 Na or K and B Chemical class 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 239000007864 aqueous solution Substances 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000012459 cleaning agent Substances 0.000 abstract description 2
- 238000009736 wetting Methods 0.000 abstract description 2
- 239000000080 wetting agent Substances 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical group [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- USPWUOFNOTUBAD-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F USPWUOFNOTUBAD-UHFFFAOYSA-N 0.000 description 1
- IHKQBQOJQGQFLU-UHFFFAOYSA-N 1-[difluoro-(2,3,4,5,6-pentafluorophenyl)methyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C(F)(F)C1=C(F)C(F)=C(F)C(F)=C1F IHKQBQOJQGQFLU-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- RGPBQGGBWIMGMA-BJMVGYQFSA-N 5-[(e)-[5-(4-bromophenyl)-6-hydroxy-3,6-dihydro-1,3,4-oxadiazin-2-ylidene]methyl]-1h-pyrimidine-2,4-dione Chemical compound OC1O\C(=C\C=2C(NC(=O)NC=2)=O)NN=C1C1=CC=C(Br)C=C1 RGPBQGGBWIMGMA-BJMVGYQFSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- WUKAGODEPQXRMH-UHFFFAOYSA-N FC1=C(F)C(F)=C(C(F)(F)C(F)(C(F)(F)F)C(F)(F)F)C(F)=C1F Chemical compound FC1=C(F)C(F)=C(C(F)(F)C(F)(C(F)(F)F)C(F)(F)F)C(F)=C1F WUKAGODEPQXRMH-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 238000011165 process development Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (AREA)
Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von fluoraromatischen nichtionogenen grenzflaechenaktiven Stoffen aus Perfluorphenylverbindungen und Alkylenoxidaddukten. Das erfindungsgemaesse Verfahren beruht darauf, dass fuer die Herstellung grenzflaechenaktiver Stoffe erstmals eine neue Stoffklasse, die der Fluoraromaten, zugaenglich gemacht wird. Die erfindungsgemaessen fluoraromatischen nichtionogenen grenzflaechenaktiven Stoffe finden aufgrund ihrer guenstigen Eigenschaften - insbesondere bewirken sie eine bedeutende Erniedrigung der Oberflaechenspannung waessriger Loesungen - vielfaeltige Verwendung in Netz- und Reinigungsmitteln oder in Feuerloeschmitteln.The invention relates to a process for the preparation of fluoroaromatic nonionic surface-active substances from perfluorophenyl compounds and alkylene oxide adducts. The process according to the invention is based on the fact that for the first time a new class of compounds, the fluoroaromatics, is made available for the production of surface-active substances. The fluoroaromatic nonionic surfactants according to the invention are widely used in wetting and cleaning agents or in fire-extinguishing agents due to their favorable properties - in particular they cause a significant reduction in the surface tension of aqueous solutions.
Description
Anwendungsgebiet der ErfindungField of application of the invention
Die Erfindung betrifft ein Verfahren zur Herstellung von fluoraromatischen nichtionogenen grenzflächenaktiven Verbindungen, die als hochwirksame Komponente in Netz- und Reinigungsmitteln oder in Feuerlöschmitteln verwendet werden können.The invention relates to a process for the preparation of fluoroaromatic nonionic surface-active compounds which can be used as a highly effective component in wetting and cleaning agents or in fire-extinguishing agents.
Charakteristik der bekannten technischen LösungenCharacteristic of the known technical solutions
Es ist bekannt, daß Fluortenside gegenüber Kohlenwasserstofftensiden vorteilhafte Eigenschaften besitzen, so daß durch ihre Anwendung neue Produkte und Verfahrensentwicklungen auf verschiedenen Gebieten der Industrie möglich werden.It is known that fluorosurfactants possess advantageous properties over hydrocarbon surfactants, so that by their application new products and process developments in various fields of industry become possible.
Diese Fluortenside werden grundsätzlich aus fluorierten aliphatischen Verbindungen synthetisiert. Geeignete Wege dafür sind die Elektrofluorierung aliphatischer Säurehalogenide/Ind. Eng. Chem. 43, 2332 (1951)/, die Telomerisation von Tetrafluorethylen /J.These fluorosurfactants are basically synthesized from fluorinated aliphatic compounds. Suitable routes for this are the electrofluorination of aliphatic acid halides / Ind. Closely. Chem. 43, 2332 (1951) /, the telomerization of tetrafluoroethylene / J.
Chem. Soc. (London) 60(1951) und 3671 (1953)/, die Oligomerisierung von Tetrafluorethylen/J. Org. Chem. 31, (1966)/und der strahlenchemische Abbau von Polytetrafluorethylen (DD-PS 131 555).Chem. Soc. (London) 60 (1951) and 3671 (1953) /, the oligomerization of tetrafluoroethylene / J. Org. Chem. 31, (1966) / and the radiation-chemical degradation of polytetrafluoroethylene (DD-PS 131 555).
Es zeigte sich aber, daß eine breitere Palette von Tensiden unterschiedlicher Strukturformeln notwendig ist, um auf den verschiedenen Anwendungsgebieten jeweils optimale Wirkungen zu erzielen.However, it has been found that a wider range of surfactants of different structural formulas is necessary to achieve optimal effects in the various fields of application.
Synthesen grenzflächenaktiver Verbindungen unter Verwendung von Fluoraromaten sind nicht bekannt.Syntheses of surface-active compounds using fluoroaromatics are not known.
Ziel der ErfindungObject of the invention
Das Ziel der Erfindung besteht darin, ein Verfahren zur Herstellung von Fluortensiden auf Basis von Fluoraromaten zu entwickeln, bei denen der spezifische Einfluß der fluoraromatischen Gruppierung innerhalb des Gebietes der Tensidchemie anwendungstechnisch wirksam werden kann.The object of the invention is to develop a process for the preparation of fluorinated aromatic fluorosurfactants in which the specific influence of the fluoroaromatic grouping within the field of surfactant chemistry can be effective in terms of application.
Darlegung des Wesens der ErfindungExplanation of the essence of the invention
Das Ziel der Erfindung wird erreicht durch ein Verfahren zur Herstellung fluoraromatischer nichtionogener grenzflächenaktiver Stoffe der allgemeinen FormelThe object of the invention is achieved by a process for the preparation of fluoroaromatic nonionic surfactants of the general formula
A - C6F4 - (OCH - CH2)a - (0CH2CH2)b I CH,A - C 6 F 4 - (OCH - CH 2 ) a - (OCH 2 CH 2 ) b I CH,
A CnF2n + 1, CnF2n + 1CH2O, H^F21nCH2O1C6F51C6F5CF2, C6F5CH2, F, B OH, OCpH2p + 1 und a die Werte O bis 10,AC n F 2n + 1 , C n F 2n + 1 CH 2 O, H ^ F 21n CH 2 O 1 C 6 F 51 C 6 F 5 CF 2 , C 6 F 5 CH 2 , F, B OH, OCpH 2p + 1 and a the values O to 10,
m 2, 4, 6 und 8 sowiem 2, 4, 6 and 8 as well
indem erfindungsgemäß Perfluorphenylverbindungen des Typs A-C6F5, worin A die obengenannte Bedeutung besitzt, unter intensivem Rühren bei Normaldruck und einer Temperatur zwischen 20 und 130°C mit Gemischen von Alkylenoxidaddukten der M- (OCH -' CH2)a - (0CH2-CH2)b - Bby according to the invention perfluorophenyl compounds of the type AC 6 F 5 , wherein A has the abovementioned meaning, with vigorous stirring at normal pressure and a temperature between 20 and 130 ° C with mixtures of Alkylenoxidaddukten the M- (OCH - 'CH 2 ) a - (0CH 2 -CH 2 ) b - B
worin M ein Alkalimetall wie Na oder K ist und B, a und b die obengenannten Bedeutungen haben, und Alkalihydroxid oder metallischem Natrium umgesetzt werden.wherein M is an alkali metal such as Na or K and B, a and b have the abovementioned meanings, and alkali metal hydroxide or metallic sodium are reacted.
A - C6F5 + M - (OCH - CH2)a - (OCH2 - CH2)b - BA - C 6 F 5 + M - (OCH - CH 2 ) a - (OCH 2 - CH 2 ) b - B
CH3 CH 3
> A - C6F4 - (OCH - CH2)a - (OCH2 - CH2)b - B + MF > A - C 6 F 4 - (OCH - CH 2 ) a - (OCH 2 - CH 2 ) b - B + MF
CH3 CH 3
Die Umsetzung erfolgt durch Kombinieren der beiden Reaktanten miteinander, wobei auch ein Lösungsmittel wie Acetonitril, Pyridin oder Dimethylsulfoxid zugegen sein kann.The reaction is carried out by combining the two reactants with each other, whereby a solvent such as acetonitrile, pyridine or dimethyl sulfoxide may be present.
Als Alkylenoxidaddukte eignen sich sowohl reine Ethylenoxidaddukte als auch gemischte Propylenoxid/Ethylenoxid-Addukte mit ein oder zwei Hydroxygruppen am Ende. Sie werden in mindestens molaren Mengen — bezogen auf die Perfluorphenylverbindung — eingesetzt.Suitable alkylene oxide adducts are both pure ethylene oxide adducts and mixed propylene oxide / ethylene oxide adducts having one or two hydroxyl groups at the end. They are used in at least molar amounts - based on the perfluorophenyl compound.
Die erfindungsgemäß erhaltenen Verbindungen sind als Tenside einsetzbar. Sie reduzieren die Oberflächenspannung des Wassers maximal bis in den Bereich von 26 bis 20 mN/m.The compounds obtained according to the invention can be used as surfactants. They reduce the surface tension of the water to a maximum of 26 to 20 mN / m.
Ausführungsbeispieleembodiments
93 g (0,5 mol) Hexafluorbenzen werden bei Raumtemperatur langsam unter Rühren zu einer Lösung von 11,5 g Natrium in 900 g Polyethylenglycol (MG450) zugetropft. Nach beendeter Zugabe wird das Reaktionsgemisch 16 Stunden lang bei 80 bis 100°C erwärmt. Anschließend wird das Reaktionsprodukt durch multiplikative Verteilung mit dem Lösungsmittelsystem gesättigte Natriumchloridlösung/Essigsäureethylester von den übrigen Verbindungen abgetrennt. Nach Abdampfen des Essigsäureethylesters werden 210 g (71 %d. Th.) der Verbindung C6Fs-(OCH2-CH2)Io-OH erhalten, deren Struktur IR- und 19F-NMR-Spektren bestätigen und deren wäßrige Lösungen folgende Oberflächenspannung besitzen: Konz. (Gew.-%): 1 0,1 0,0193 g (0.5 mol) of hexafluorobenzene are slowly added dropwise at room temperature with stirring to a solution of 11.5 g of sodium in 900 g of polyethylene glycol (MG450). After completion of the addition, the reaction mixture is heated at 80 to 100 ° C for 16 hours. Subsequently, the reaction product is separated by multiplicative distribution with the solvent system saturated sodium chloride solution / ethyl acetate from the remaining compounds. After evaporation of the ethyl acetate, 210 g (71% of theory) of the compound C 6 Fs- (OCH 2 -CH 2 ) Io-OH are obtained, the structure of which is confirmed by IR and 19 F-NMR spectra and their aqueous solutions following Have surface tension: Conc. (Wt.%): 1 0.1 0.01
σ (mN/m): 26 34σ (mN / m): 26 34
23 g (0,1 mol) Octafluortoluen werden mit 88 g (0,1 mol) der Natriumverbindung des Ethylenoxid/Propylenoxid-Polymeren23 g (0.1 mol) of octafluorotoluene are mixed with 88 g (0.1 mol) of the sodium compound of the ethylene oxide / propylene oxide polymer
H(OCH-CH2)4-(OCH2CH2)14-0CH3 CH3 H (OCH-CH 2 ) 4 - (OCH 2 CH 2 ) 14 -OCH 3 CH 3
langsam auf 80 bis 1000C erwärmt und für 8 Stunden bei dieser Temperatur gerührt. Anschließend wird das Reaktionsgemisch in 500 ml Wasser gegossen. Die nichtreagierende Menge des Fluoraromaten (8 g) scheidet sich als untere Phase ab. Dann wird das Reaktionsprodukt mit Essigsäureethylester extrahiert. Nach dem Abdestillieren des Extraktionsmittels werden 70,5 g (64 %) der Verbindungheated slowly to 80 to 100 0 C and stirred for 8 hours at this temperature. Then the reaction mixture is poured into 500 ml of water. The non-reactive amount of the fluoroaromatic (8 g) separates out as the lower phase. Then the reaction product is extracted with ethyl acetate. After distilling off the extractant 70.5 g (64%) of the compound
CF3-C6F4-(OCH-CH2J4-(OCH2CH2)14-0CH3 CH3 CF 3 -C 6 F 4 - (OCH-CH 2 J 4 - (OCH 2 CH 2 ) 14 -OCH 3 CH 3
erhalten. '9F-NMR- und IR-Spektrum bestätigen die Struktur der grenzflächenaktiven Verbindung. Konz. (Gew.-%): 1 0,1 0,01receive. The 9 F NMR and IR spectra confirm the structure of the surfactant compound. Conc. (Wt .-%): 1 0.1 0.01
σ (mN/m): 24 29σ (mN / m): 24 29
Ein Gemisch von 39 g (0,1 mol) Perfluor-isobutylbenzen und 185 g (0,2 mol) Polyethylenglycol-monoethylester (20 Ethylenoxideinheiten), in dem zuvor 2,3 g (0,1 mol) Natrium gelöst werden, wird bei einer Temperatur von 90 bis 1000C für 9 Stunden gerührt. Anschließend werden 9 g nichtumgesetzten Fluoraromats abdestilliert und der Rückstand in eine wäßrige Natriumchlorid-Lösung gegossen. Daraus läßt sich das gebildete Fluortensid mit Chloroform extrahieren. Nach Abdestillieren des Lösungsmittels verbleiben 77,5 g (60%) der Verbindung (CF3)2CF-CF2-C6F4-{OCH2CH2)20-OC2H5. Die Struktur der Verbindung konnte durch IR- und 19F-NMR-Spektren sowie durch die Fluor-Elementaranalyse bestätigt werden. In wäßriger Lösung liegt folgende Oberflächenspannung vor: Konz. (Gew.-%): 1 0,1 0,01A mixture of 39 g (0.1 mol) of perfluoroisobutylbenzene and 185 g (0.2 mol) of polyethylene glycol monoethyl ester (20 ethylene oxide units), in which previously dissolved 2.3 g (0.1 mol) of sodium, is at stirred at a temperature of 90 to 100 0 C for 9 hours. Subsequently, 9 g of unreacted fluoroaromatic are distilled off and the residue poured into an aqueous sodium chloride solution. From this, the fluorosurfactant formed can be extracted with chloroform. After distilling off the solvent remain 77.5 g (60%) of the compound (CF 3 ) 2 CF-CF 2 -C 6 F 4 - {OCH 2 CH 2 ) 20 -OC 2 H 5 . The structure of the compound was confirmed by IR and 19 F NMR spectroscopy and by elemental fluorine analysis. The following surface tension is present in aqueous solution: Conc. (Wt .-%): 1 0.1 0.01
σ (mN/m): 23 27 29σ (mN / m): 23 27 29
Eine äquimolare Menge Kaliumhydroxid wird in 22 g (0,02 mol) Polyethylenglycol-monomethylether (MG 1100) gelöst. Dazu werden 100 ml Acetonitril gegeben, darauf 11,3 g (0,02 mol) ΙΗ,ΙΗ-Perfluoroctyl-pentafluorphenyl-ether. Unter Rühren wird 14 Stunden bei 80 bis 900C erwärmt. Nach Abdestillieren des Acetonitrils und Abscheiden der fluorhaltigen Ausgangsverbindung (5 g) aus dem in Wasser gegossenen Reaktionsgemisch wird durch multiplikative Verteilung mit dem System gesättigte Natriumchlorid-Lösung/Essigsäureethylester das Zielprodukt C7F15CH2O-C6F4-(OCH2CH2I24-OCH3 erhalten (18 g, 55% d. Th.). 1H- und I9F-NMR-Spektren bestätigen die Struktur der grenzflächenaktiven Verbindung, deren wäßrige Lösung folgende Oberflächenspannung besitzt: Konz. (Gew.-%): 1 0,1 0,01An equimolar amount of potassium hydroxide is dissolved in 22 g (0.02 mol) of polyethylene glycol monomethyl ether (MW 1100). 100 ml of acetonitrile are added, followed by 11.3 g (0.02 mol) of ΙΗ, ΙΗ-perfluorooctyl-pentafluorophenyl ether. While stirring, heated at 80 to 90 0 C for 14 hours. After distilling off the acetonitrile and depositing the fluorine-containing starting compound (5 g) from the water-poured reaction mixture by multiplicative distribution with the system saturated sodium chloride solution / ethyl acetate, the target product C 7 F 15 CH 2 OC 6 F 4 - (OCH 2 CH 2 I 24 -OCH 3 (18 g, 55% of theory). 1 H and 19 F-NMR spectra confirm the structure of the surface-active compound whose aqueous solution has the following surface tension: conc. : 1 0.1 0.01
σ (mN/m): 21 22 26σ (mN / m): 21 22 26
5,6 g (0,1 mol) Kaliumhydroxid werden in 0,5 mol Polyethylenglycol (MG722) gelöst. Dazu werden langsam 49;6 g (0,1 mol) 1 H,1 H,7H-Perfluorheptyl-pentafluorphenyl-ether und 50 ml Pyridin gegeben. Die Reaktion erfolgt unter Abscheidung von Kaliumfluorid innerhalb von 14 Stunden bei einer Temperatur von 90 bis 100°C. Durch Eintragen des Reaktionsgemisches in Wasser (400 ml) nach Abdestillieren des Pyridins im Vakuum wird der Anteil an nichtumgesetztem Fluoraromat abgetrennt. Aus dem verbleibenden Produkt wird nach Zugabe von 50 g Natriumchlorid und 200 ml Essigsäureethylester die Verbindung H(CF2)6CH2O-C6F4-(OCH2CH2)16-OH extrahiert. Ausbeute 72 g (60% d. Th.).5.6 g (0.1 mol) of potassium hydroxide are dissolved in 0.5 mol of polyethylene glycol (MG722). To this are added slowly 49, 6 g (0.1 mol) of 1H, 1H, 7H-perfluoroheptyl-pentafluorophenyl ether and 50 ml of pyridine. The reaction is carried out with deposition of potassium fluoride within 14 hours at a temperature of 90 to 100 ° C. By adding the reaction mixture in water (400 ml) after distilling off the pyridine in vacuo, the proportion of unreacted fluorine is separated. From the remaining product, after addition of 50 g of sodium chloride and 200 ml of ethyl acetate, the compound H (CF 2 ) 6 CH 2 OC 6 F 4 - (OCH 2 CH 2 ) 16 -OH is extracted. Yield 72 g (60% of theory).
19F-, 1H-NMR sowie IR-Spektren bestätigen die Struktur. Bei 40 °C zeigen wäßrige Lösungen der Verbindung folgende Oberflächenspannung: 19 F, 1 H-NMR and IR spectra confirm the structure. At 40 ° C., aqueous solutions of the compound show the following surface tension:
Konz. (Gew.-%): 1 0,1 0,01Conc. (Wt .-%): 1 0.1 0.01
σ (mN/m): 22 24 28σ (mN / m): 22 24 28
2,3 g (0,1 mol) Natrium werden in 109 g (0,2 mol) Polyethylenglycol (MG528) gelöst und dazu anschließend 38,4 g (0,1 mol) Perfluor-diphenylmethan getropft. Das Reaktionsgemisch wird für 8 Stunden bei 90 bis 100°C unter Rühren erwärmt. Nach Eintragen des Reaktionsproduktes in 500 ml gesättigte Natriumchlorid-Lösung wird daraus mit Essigsäureethylester das gebildete nichtionogene Tensid in einer Menge von 48 g (53 % d. Th.) extrahiert. Das 19F-NMR-Spektrum bestätigt die Struktur folgender Verbindung:2.3 g (0.1 mol) of sodium are dissolved in 109 g (0.2 mol) of polyethylene glycol (MG528) and then added dropwise 38.4 g (0.1 mol) of perfluorodiphenylmethane. The reaction mixture is heated for 8 hours at 90 to 100 ° C with stirring. After the reaction product has been introduced into 500 ml of saturated sodium chloride solution, the nonionic surfactant formed is extracted with ethyl acetate in an amount of 48 g (53% of theory). The 19 F-NMR spectrum confirms the structure of the following compound:
C6F5-CF2-CeF4(OCH2CH2)12-OH. Geringe Mengen an disubstituiertem Produkt beeinträchtigen die Grenzflächenaktivität nicht negativ:C 6 F 5 -CF 2 -C e F 4 (OCH 2 CH 2 ) 12 -OH. Small amounts of disubstituted product do not adversely affect interfacial activity:
Konz. (Gew.-%): 1 0,1 0,01Conc. (Wt .-%): 1 0.1 0.01
σ (mN/m): 20 21 25σ (mN / m): 20 21 25
Claims (2)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD27520185A DD249384A3 (en) | 1985-04-16 | 1985-04-16 | METHOD FOR PRODUCING FLUORAROMATIC NON-ATIONOGENIC BORDER-ACTIVE SUBSTANCES |
| SU867774084A SU1694595A1 (en) | 1985-04-16 | 1986-01-28 | Method for preparation of polyalkyleneoxide derivatives of perfluorobenzene with surface-active properties |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD27520185A DD249384A3 (en) | 1985-04-16 | 1985-04-16 | METHOD FOR PRODUCING FLUORAROMATIC NON-ATIONOGENIC BORDER-ACTIVE SUBSTANCES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD249384A3 true DD249384A3 (en) | 1987-09-09 |
Family
ID=5566891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD27520185A DD249384A3 (en) | 1985-04-16 | 1985-04-16 | METHOD FOR PRODUCING FLUORAROMATIC NON-ATIONOGENIC BORDER-ACTIVE SUBSTANCES |
Country Status (2)
| Country | Link |
|---|---|
| DD (1) | DD249384A3 (en) |
| SU (1) | SU1694595A1 (en) |
-
1985
- 1985-04-16 DD DD27520185A patent/DD249384A3/en not_active IP Right Cessation
-
1986
- 1986-01-28 SU SU867774084A patent/SU1694595A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| SU1694595A1 (en) | 1991-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69618020T2 (en) | METHOD FOR PRODUCING HYDROFLUORETHERS | |
| EP0571832A2 (en) | Imides and their salts and their use as surface active agents | |
| DE102005000858A1 (en) | Use of trifluoromethoxy- or pentafluorosulfuranyl terminal groups as hydrophobic terminal groups in surface active compounds, which are useful as e.g. surfactants, hydrophobic agents, foam stabilizers and emulsifying agents | |
| DE69113695T2 (en) | Process for the preparation of perfluoroalkoxysulfone compounds. | |
| DE1593229A1 (en) | Perfluorovinyla ethers and process for their preparation | |
| EP0601418B1 (en) | Fluorinated carbonic esters from phosphono and phosphino carboxylic acids and their use | |
| DE1942264C3 (en) | Polyfluorosulfonic acids and their sulfonates, processes for the preparation of the polyfluorosulfonates, and the use of the compounds mentioned as surface-active agents | |
| EP0370391A2 (en) | Process for the preparation of 4,5-dichloro-6-ethyl pyrimidine | |
| DE2212604B2 (en) | PROCESS FOR THE PREPARATION OF 2-HALOGENAETHYLPHOSPHONE ACIDS | |
| DE69912353T2 (en) | METHOD FOR PRODUCING (PER) FLUOROPOLYETHERS SUBSITUATED BY ONE HALOGEN ATOM ON ONE OR BOTH TERMINALS | |
| DE1768449A1 (en) | alpha, omega-bis (fluoroperhalogenisopropoxy) -perfluoroalkanes | |
| EP0047948A2 (en) | Process for the production of polyfluorocarbonyl compounds and some representatives of this family | |
| DE69115758T2 (en) | Process for the preparation of 3,5-difluoroaniline and its derivative | |
| DE2651531A1 (en) | Process for the preparation of a fluorinated acylfluoride with an ester group | |
| EP0023293B1 (en) | Process for preparing 2.3-perfluoro-1.4-dioxanes and trifluoro methyl-1,4-dioxanes | |
| DE3817626A1 (en) | FLUORINATED TO ARYLOXY-SUBSTITUTED ALKENES, METHOD FOR THE PRODUCTION AND USE THEREOF | |
| DE3121766A1 (en) | METHOD FOR PRODUCING BASICLY SUBSTITUTED PHENYL ACETONITRILE | |
| DE3836149A1 (en) | NEW 4-TRIFLUORMETHYLMERCAPTO AND 4-TRIFLUORMETHYLSULFONYL PHENOLS AND THEIR PRODUCTION | |
| DE2239800C3 (en) | Tertiary perfluoroamino ethers and processes for their preparation | |
| DE2834169C2 (en) | Process for the preparation of 2- (2-hydroxyethoxy) ethyl-N- (alpha, alpha, alpha -trifluoro-m-tolyl) anthranilate | |
| DE60222835T2 (en) | PROCESS FOR THE PREPARATION OF 1,3-BIS (3-AMINOPHENOXY) BENZOLE | |
| DE1793160A1 (en) | Polyfluoroalkoxyisopropanols and processes for their preparation | |
| DE68908511T2 (en) | Branched perfluoroalkyl halides and process for their preparation. | |
| DE2742685A1 (en) | Hydro-per:fluoro-alkenyl carboxylic acid derivs. - prepd. by reacting di:hydro-per:fluoroalkyl carboxylic acid derivs. with nucleophilic cpds. | |
| EP0317888B1 (en) | Fluorinated nitroalkyl compounds, and process for the preparation of fluorinated nitroalkyl compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RPI | Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act) | ||
| RPI | Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act) | ||
| ENJ | Ceased due to non-payment of renewal fee |