DE646339C - Process for the production of quaternary ammonium bases - Google Patents
Process for the production of quaternary ammonium basesInfo
- Publication number
- DE646339C DE646339C DEI52259D DEI0052259D DE646339C DE 646339 C DE646339 C DE 646339C DE I52259 D DEI52259 D DE I52259D DE I0052259 D DEI0052259 D DE I0052259D DE 646339 C DE646339 C DE 646339C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- water
- ethylene oxide
- quaternary ammonium
- weight
- 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
Links
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- -1 Trim @ ethylamine Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XXDOQKYPCLBTQD-UHFFFAOYSA-N [OH-].COC(C[NH2+]CCCCCCCCCCCC)OC Chemical compound [OH-].COC(C[NH2+]CCCCCCCCCCCC)OC XXDOQKYPCLBTQD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/12—Bis-chlorophenols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Materials Engineering (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung quaternärer Ammoniumbasen Es wurde gefunden, daß man quaternäre Ammoniumbasen in sehr vorteilhafter Weise herstellen kann, wenn man Äthylenoxyd in Gegenwart von Wasser auf wasserunlösliche, tertiäre Amine, de einen hochmolekularen Rest enthalten, einwirken läßt. Hierfür sind beispielsweise tertiäre Amine mit einem aliphatischen Rest, der mindestens acht, vorteilhaft mindestens zehn Kohlenstoffatome enthält, geeignet. Die quatennären Basen können sich unter Umständen mit weiteren Mengen Äthylenoxyd unter Bildung- von Kondensationsprodukten umsetzen.Process for the production of quaternary ammonium bases It has been found that you can produce quaternary ammonium bases in a very advantageous manner if one ethylene oxide in the presence of water on water-insoluble, tertiary amines, de contain a high molecular weight residue, can act. For this, for example tertiary amines with one aliphatic radical of at least eight, advantageously at least contains ten carbon atoms is suitable. The quatennary bases can be found under Certain cases with further amounts of ethylene oxide with the formation of condensation products realize.
In manchen Fällen ist es erforderlich, einen überschuß an Äthylenoxyd anzuwenden oder mehrmals Äthylenoxyd einwirken zu lassen, um völlige Umwandlung des tertiären Amins in die leicht wasserlöslichen quaternären Ammoniumbasen bzw. deren Kondensationspro,dukte mit Äthylenoxyd zu erzielen.In some cases it is necessary to use an excess of ethylene oxide apply or let ethylene oxide act several times to achieve complete transformation of the tertiary amine into the easily water-soluble quaternary ammonium bases or to achieve their condensation products with ethylene oxide.
Die bei dem Verfahren entstehenden Produkte sind wasserlöslich und reagieren alkalisch. Sie besitzen. ;großes Schaum- und Netzvermögen und sind wertvolle Hilfsprodukte für die Textilindustrie und verwandte Gebiete. Auch für Desinfektionszwecke können sie verwendet werden.The products resulting from the process are water-soluble and react alkaline. You own. ; great foam and wetting power and are valuable Auxiliary products for the textile industry and related fields. Also for disinfection purposes can they be used.
Män hat schon niedrigmolekulare, wasserlösliche, tertiäre Amine, wie Trim@ethylamin, mit Äthylenoxyd zu quaternären Ammoniumverbindungen umgesetzt. Hieraus war aber nicht zu entnehmen, daß wasserunlösliche, tertiäre Amine mit einem hochmolekularen Rest durch - Einwirkung von Äthylenoxyd in Gegenwart von Wasser in glatter Umsetzung in .quaternäre Ammoniumbasen übergeführt werden können, zumal sich das wasserunlösliche Tributylamin, das keinen hochmolekularen Rest enthält, nicht in entsprechender Weise umwandeln läßt.Mann already has low molecular weight, water-soluble, tertiary amines, such as Trim @ ethylamine, reacted with ethylene oxide to form quaternary ammonium compounds. From this but was not to be found that water-insoluble, tertiary amines with a high molecular weight Remainder by - exposure to ethylene oxide in the presence of water in smooth implementation Can be converted into .quaternary ammonium bases, especially since the water-insoluble Tributylamine, which does not contain a high molecular weight residue, does not in a corresponding manner can convert.
Beispiel i In eine Aufschlämmung von 213 Teilen Dimethyldodecylamin in 64o Teilen Wasser leitet man unter starkem Rühren bei 5o bis 6o° 5o Teile Äthylenoxyd ein. Man erhält eine klare, viscose Lösung von Dimethyloxyäthyldodecylammoniumhydroxyd, die stark alkalisch reagiert. Auch eine alkoholische Lösung des Produktes reagiert alkalisch gegen Phenolphthalein, während der Ausgangsstoff in Alkohol neutral reagiert.Example i Into a slurry of 213 parts of dimethyldodecylamine 50 parts of ethylene oxide are passed into 64o parts of water with vigorous stirring at 50 to 60 ° a. A clear, viscous solution of dimethyloxyethyldodecylammonium hydroxide is obtained, which reacts strongly alkaline. An alcoholic solution of the product also reacts alkaline to phenolphthalein, while the starting material reacts neutrally in alcohol.
Beispiel 2 iooo Teile eines Gemisches von Aminen, die je zwei: Methylgruppen und einen Alkylrest enthalten, der den durch Reduktion der Palmkernfettsäurenerhältlichen Alkoholen entspricht, werden in 2ooo Teilen Wasser verteilt. In die verhaltene Aufschlämmung leitet man bei 5o bis 60° Zoo Teile Äthylenoxyd ein, läßt absitzen und trennt die wässerige Lösung von den nicht umgesetzten Anteilen des wasserunlöslichen Amins ab. Man erhält so 23oo Teile einer viscosen Löswg r von 2_ i'ä (worin R dem oben gekennzeichneten Alkylrest :entspricht), und zwar sind etwa 43°/a des angewandten Amins in die quaternäre Base übergeführt worden. Der nicht veränderte Teil des Amins kann durch wiederholte Behandlung mit Äthylenoxyd in die quaternäre Base umgewandelt werden.EXAMPLE 2 1,000 parts of a mixture of amines, each containing two: methyl groups and one alkyl radical, which corresponds to the alcohols obtainable by reducing the palm kernel fatty acids, are distributed in 2,000 parts of water. Parts of ethylene oxide are passed into the restrained suspension at 50 to 60 °, allowed to settle and the aqueous solution is separated off from the unreacted portions of the water-insoluble amine. This gives 2,300 parts of a viscous solution of 2_ i'ä (in which R corresponds to the above-identified alkyl radical:), namely about 43% / a of the amine used has been converted into the quaternary base. The unchanged part of the amine can be converted into the quaternary base by repeated treatment with ethylene oxide.
Beispiel 3 75 Teile DinlethyIoctodecylamin «erden in i 5o Teilen Wasser aufgeschlämmt und mit I5 Teilen Äth@lenoxyd bei 5o bis 6o° umgesetzt. Hierauf werden nochmals i oo Teile Wasser und i 5 Teile Äthylenoxyd zugegeben. Es entsteht eine gallertartige bis feste Masse, die mit weiteren Zoo Teilen Wasser eine opaleszierende Lösung bildet.Example 3 75 parts of dimethyl octodecylamine ground in 15 parts of water slurried and implemented with 15 parts of Äth @ lenoxyd at 5o to 6o °. Be on it a further 100 parts of water and 5 parts of ethylene oxide were added. It creates a Gelatinous to solid mass that becomes opalescent with other zoo parts of water Solution forms.
Beispiel 4 107 Teile Dimethyldodecylamin werden in 25o Teilen Wasser -erteilt. Man leitet nun bei 5o bis 6o° iooTeile Äthylenoxyd ein. Die klare Lösung erstarrt beim Erkalten zu einer gelatineartigen Masse, die leicht in Wasser löslich ist. Aus der stark alkalischen Lösung wird das Produkt weder durch Säure noch durch Alkali abgeschieden.Example 4 107 parts of dimethyldodecylamine are dissolved in 250 parts of water - shared. Ethylene oxide is now introduced at 50 to 60 ° 100 parts. The clear solution solidifies to a gelatinous mass on cooling, which is easily soluble in water is. The product is not transformed from the strongly alkaline solution by acid or by Alkali deposited.
Beispiel 5 5oo Teile des in Beispiel 2 genannten Aüsgangsstof-fes werden mit ioooTeilen Wasser und 5oo Teilen Äthylenoxyd im Autoklaven auf 70-bis 8o" erwärmt. Die noch heiß aus dem Autoklaven entfernte Masse erstarrt zu einer bräunlichen, leicht in Wasser löslichen Gallerte.Example 5 500 parts of the starting material mentioned in Example 2 are with 100 parts of water and 500 parts of ethylene oxide in an autoclave to 70-bis 8o ". The mass removed from the autoclave while still hot solidifies to form a brownish jelly, easily soluble in water.
Beispiel 6 25oTeile des in Beispie12 genannten Ausgangsstoffes werden mit 5ooTeilen Wasserund 45oTeilen Äthylenoxyd bei o bis 5° in einen Autoklaven eingebracht und ohne äußere Wärmezufuhr gerührt. Die Temperatur steigt langsam auf go°. Das entstandene Produkt ist eine dicke, bräunliche, sirupartige, stark alkalisch reagierende, leicht in Wasser lösliche Masse.Example 6 25o parts of the starting material mentioned in Beispie12 placed in an autoclave with 500 parts of water and 45o parts of ethylene oxide at 0 to 5 ° and stirred without external heat supply. The temperature rises slowly to go °. That The resulting product is a thick, brownish, syrupy, strongly alkaline reacting, Easily soluble in water.
Beispiel 7 i o8 Gewichtsteile Dimethyldodecylamin werden in 3.15 Gewichtsteilen Methanol gelöst.' und nach Zugabe von 17 Gewichtsteilen Wasser mit 3o Gewichtsteilen Athylenoxyd irn ;-- eschlossenen Gefäß auf 9o° erhitzt. Nach i i is 2 Stunden ist alles Athylenoxyd aufge-;nommen. Nach dem Abdampfen des Methanols (iili Vakuum bei 4o°) hinterbleibt 88 prozentiges Diäthyloxyäthyldodecylammoniumhydroxyd als leicht wasserlösliche, bräunliche, sirupartige Masse.Example 7 10 8 parts by weight of dimethyldodecylamine are converted into 3.15 parts by weight Dissolved methanol. ' and after adding 17 parts by weight of water with 3o parts by weight Ethylene oxide heated to 90 ° in a closed vessel. After i i is 2 hours all ethylene oxide taken up. After evaporation of the methanol (iili vacuum at 40 °) 88 percent diethyloxyethyldodecylammonium hydroxide remains as light water-soluble, brownish, syrupy mass.
Beispiel 8 25o Gewichtsteile Dimethylpalmkernfettamin werden in einem Gemisch von 5oo Gewichtsteilen Methanol und 2o Gewichtsteilen Wasser mit 5o Gewichtsteilen Äthylenoxyd im Autoklaven auf go bis ioo° erhitzt. Nach Beendigung der Umsetzung wird das Methanol im Vakuum bei 6o° verdampft. Man erhält in quantitativer Ausbeute Dimethyläthanolpaimkernfettainmoniumhydroxyd als 78prozentige, leicht wasserlösliche, sirupartige Lösung.Example 8 250 parts by weight of dimethyl palm kernel fatty amine are in one Mixture of 500 parts by weight of methanol and 20 parts by weight of water with 50 parts by weight Ethylene oxide heated to 100 ° in the autoclave. After completion of the implementation the methanol is evaporated in vacuo at 6o °. It is obtained in quantitative yield Dimethylethanolpaimkernfettainmoniumhydroxyd as 78 percent, easily water-soluble, syrupy solution.
Beispiel 9 In eine Aufschlämmung von i 57 Gewichtsteilen Dim@ethyloctylamin in 72o Gewichtsteilen Wasser werden unter kräftigem Rühren bei 6o bis 70° 25o Gewichtsteile Äthylenoxyd eingeleitet. Nach Abtrennung des unlöslichen, nicht umgesetzten Dimethyloctylamins erhält man eine Lösung von Polyoxyäthyldimethyloctylammoniumhydroxyd. Man kann die Umsetzung auch im geschlossenen Gefäß durchführen.Example 9 Into a slurry of 57 parts by weight of dim @ ethyloctylamine in 72o parts by weight of water with vigorous stirring at 6o to 70 ° 25o parts by weight Ethylene oxide initiated. After separating off the insoluble, unreacted dimethyloctylamine a solution of polyoxyethyldimethyloctylammonium hydroxide is obtained. You can Implementation also in a closed vessel.
Beispiel io go Gewichtsteile Dimethyldecylamin werden in 3oo Gewichtsteilen Wasser fein verteilt. Nach dem Erwärmen des Gemisches auf 70° leitet man 125 Gewichtsteile Äthylenoxyd ein, die vollständig aufgenommen werden. Nach Abtrennung des nicht umgesetzten Amins, das einer erneuten Behandlung mit Äthylenoxyd unterworfen werden kann, erhält man 485 Gewichtsteile einer Lösung des Polyoxyäthyldimethyldecylammoniumhydroxyds: 66 % des angewandten Amins sind in die quaternäre Ammoniumbase umgewandelt worden.Example 10 parts by weight of dimethyldecylamine are finely divided in 300 parts by weight of water. After the mixture has been heated to 70 °, 125 parts by weight of ethylene oxide are introduced, which are completely absorbed. After separating off the unreacted amine, which can be subjected to renewed treatment with ethylene oxide, 485 parts by weight of a solution of polyoxyethyldimethyldecylammonium hydroxide are obtained: 66% of the amine used has been converted into the quaternary ammonium base.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI52259D DE646339C (en) | 1935-05-05 | 1935-05-05 | Process for the production of quaternary ammonium bases |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI52259D DE646339C (en) | 1935-05-05 | 1935-05-05 | Process for the production of quaternary ammonium bases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE646339C true DE646339C (en) | 1937-06-11 |
Family
ID=7193303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI52259D Expired DE646339C (en) | 1935-05-05 | 1935-05-05 | Process for the production of quaternary ammonium bases |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE646339C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10139963A1 (en) * | 2001-08-14 | 2003-03-06 | Wacker Chemie Gmbh | Organopolysiloxanes containing quaternary ammonium groups and process for their preparation |
-
1935
- 1935-05-05 DE DEI52259D patent/DE646339C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10139963A1 (en) * | 2001-08-14 | 2003-03-06 | Wacker Chemie Gmbh | Organopolysiloxanes containing quaternary ammonium groups and process for their preparation |
| US6730766B2 (en) | 2001-08-14 | 2004-05-04 | Wacker-Chemie Gmbh | Organopolysiloxanes having quaternary ammonium groups and processes for the preparation thereof |
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