DE669541C - Process for the preparation of sulfonation products of unsaturated or hydroxylated compounds of the aliphatic series - Google Patents
Process for the preparation of sulfonation products of unsaturated or hydroxylated compounds of the aliphatic seriesInfo
- Publication number
- DE669541C DE669541C DEB145809D DEB0145809D DE669541C DE 669541 C DE669541 C DE 669541C DE B145809 D DEB145809 D DE B145809D DE B0145809 D DEB0145809 D DE B0145809D DE 669541 C DE669541 C DE 669541C
- Authority
- DE
- Germany
- Prior art keywords
- unsaturated
- aliphatic series
- preparation
- sulfonation products
- hydroxylated compounds
- 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
- 238000006277 sulfonation reaction Methods 0.000 title claims description 10
- 125000001931 aliphatic group Chemical group 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical class O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- -1 wool sweat Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- 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
- C09K23/04—Sulfonates or sulfuric acid ester salts derived from polyhydric alcohols or amino alcohols or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/20—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
Verfahren zur Herstellung von Sulfonierungsprodukten ungesättigter oder hydroxylierter Verbindungen der aliphatischen Reihe Es ist bekannt, die Sulfonierungsprodukte von Fettsäuren und Fettsäurederivaten aas Mittel zur Erhöhung der netzenden, reinigenden, dispergierenden und Schaumwirkung von Flüssigkeiten zu verwenden..Process for the preparation of sulfonation products of unsaturated or hydroxylated compounds of the aliphatic series It is known the sulfonation products of fatty acids and fatty acid derivatives as a means to increase the wetting, cleansing, to use dispersing and foaming effect of liquids.
Es ist auch schon vorgeschlagen worden, eine Reihe verschiedener Substanzgemische, wie Wollschweiß, Erdöldestil'.!ate, Lanolin, Gemische von Ölsäure mit Benzol oder von Mineralöl und- Propylallkohol usw., der Sulfonierung mittels Chlorsulfonsäure zu unterwerfen, wobei infolge der besonders energischen Wirkung der Chlorsulfonsäure zugleich mit der Sulfonierung eire Kondensation der heterogenen Bestandteile der Ge.-mische stattfinden soll. Weiter ist es auch bekannt, Derivate von Kohlenwasserstoffen, als welche insbesondere die Fetts.äunen genannt sind, mit sehr energischen Sulfonier ungsmitteln, wie z. B. Schwefels,äure@aahydrid oder Chlors,ulfons.äure, zu behandeln.. Diese Verfahren ergeben jedoch durchweg ungleichmäßige, sehr dunkel ;gefärbte Produkte, die einer besonderen Reinigung bedürfen, um überhaupt für die Textilindustrie verwendbar zu sein.It has also been proposed to use a number of different substance mixtures, like wool sweat, petroleum style.! ate, lanolin, mixtures of oleic acid with benzene or of mineral oil and propyl alcohol, etc., sulfonation using chlorosulfonic acid subject to, being due to the particularly vigorous action of chlorosulfonic acid Simultaneously with the sulfonation eire condensation of the heterogeneous components of the Mixing should take place. It is also known to use derivatives of hydrocarbons, as which especially the Fetts.äunen are named, with very energetic sulfonians ungsmittel, such as. B. sulfur, acid @ aahydride or chlorine, sulfonic acid, to treat .. However, these processes consistently result in uneven, very dark; colored products, which require special cleaning in order to be used at all for the textile industry to be.
Man hat auch schon an Stelle der Fettsäuren oder Fettsäureglyceride die diesen Fettsäuren entsprechenden Alkohole mit der gleichen Anzahl Kohlenstoffatome als Ausgangsmaterial für die Herstellung von Sulfonierun;gsprodukten verwandt.One has already in place of the fatty acids or fatty acid glycerides the alcohols corresponding to these fatty acids with the same number of carbon atoms used as a starting material for the production of sulfonation products.
Schließlich ist .es .auch bereits bekannt, Aminoäthylalkohol durch Einwirkung von. Sulfonierungsmitteln in den Schwefelsäureesber überzuführen, indem man in den mittels Kältemischung auf tiefe Temperatur abgekühlten Aminojäthylalkohol tropfenweise rauchende Schwefelsäure einträgt. Für höher molekulare Körper der Reihe der Oxyamine, deren Schmelzpunkt oberhalb o° liegt, ist diese Arbeitsweise nichtanwendbar.Finally, it is already known to use aminoethyl alcohol Exposure to. To convert sulfonating agents into sulfuric acid by one in the amino ethyl alcohol cooled to a low temperature by means of a cold mixture introduces fuming sulfuric acid drop by drop. For higher molecular bodies of the series the oxyamines, the melting point of which is above 0 °, this procedure cannot be used.
Es wurde nun gefunden, daß man bei der Einwirkung von Sulfonierung.smitteln
bei Temperaturen über o° auf in ;geeigneter Weise dispergierte .oder verflüssigte
höhere aliphatische ungesättigte Amine und höhere Oxyamine mit mehr als 8 Kohlenstoffatomen
in der Kette, deren Schmelzpunkt oberhalb o° liegt, wasserlösliche Produkte erhält,
welche sich .als solche oder in Förm ihrer Salze für die oben angegebenen Zwecke
vorzüglich eignen. Je nach den bei der Sulfonierung angewendeten Bedingungen erhält
man Produkte, welche ihrer Konstitution nach entweder vorwiegend Schwefelsäureester
oder vorwiegend echte Sulfonsäuren von aliphatischen Oxyanunen bzw. ungesättigten
Aminen sind.
Die Herstellung -der-,. Produkte kann, beispielsweise
folgendermaßen vorgenommen werden.
2. 38o kg Octadecanolaminchlorhydrat werden in 2ookg -Trichloräthylen eingetragen und bei i o' mit i 2o kg Chlorsulfonsävxe sulfoniert. Das Produkt wird auf Eis gedrückt und mit gesättigter Glaubersalzlösung zur Entfernung der überschüssigen Schwefelsäure und Salzsäure .gewaschen. Man neutralisiert dann mit Natronlauge und destilliert das Trichloräthylen ab.2. 38o kg of octadecanolamine chlorohydrate are dissolved in 2ookg trichlorethylene entered and sulfonated at i o 'with i 2o kg of chlorosulfonic acid. The product will pressed on ice and with saturated Glauber's salt solution to remove the excess Sulfuric acid and hydrochloric acid .washed. It is then neutralized with sodium hydroxide solution and the trichlorethylene distills off.
3. 325 kg Octadecenylamin werden bei 25° mit 325 kg konzentrierter Schwefelsäure und i i o kg Essigs;äureanhydrid sulfoniert. Das Produkt wird.auf Eis ,gedrückt, mit gesättigter Glaubersalzlösung zur Entfernung der überschüssigen Schwefelsäure und Essigsäure ,gewaschen und mit Natronlauge neutralisiert.3. 325 kg of octadecenylamine are more concentrated at 25 ° with 325 kg Sulfuric acid and 10 kg of acetic acid anhydride sulfonated. The product will.on Ice, pressed, with saturated Glauber's salt solution to remove the excess Sulfuric acid and acetic acid, washed and neutralized with sodium hydroxide solution.
4. i4o g 41-Amino-4-äthylheptadien-(i, 6)-C., Hl ; N, Strukturformel werden mit i oo g Äthyläther versetzt und bei Temperaturen von o bis io° mit 232 kg Chlorsulfons,äure behandelt, bis .eine Probe sich nach Abdampfen des Äthers als vflllig was:s:erlöslich erweist. Das Produkt wird auf Eis gedrückt, mit gesättigter Glaubersalzlösung zur Entfernung der überschüssigen Schwefelsäure und Salzsäure ausgewaschen und schließlich mit Natronlauge neutralisiert. Die so erhaltenen Produkte sind leicht wasserlösliche, stark netzende und schäumende Körper, welche eine hervorragende Bieständigkeit gegen hartes Wasser, Säuren, Laugen und konzentrierte Salzlösungen aufweisen. Insbesondere die Produkte, welche die Konstitution echter Sulfonsäuren haben, sind auch gegen das Kochen mit Säuren und .gegen trockenes Erhitzen. auf höhere Temperaturen so beständig, da.ß sie dabei die gebundene Schwefelsäure nicht abspalten.4. 14o g of 41-amino-4-ethylheptadiene- (1.6) -C., Hl; N, structural formula are mixed with 100 g of ethyl ether and treated with 232 kg of chlorosulfonic acid at temperatures of 0 to 10 ° until a sample proves to be completely soluble after evaporation of the ether. The product is pressed onto ice, washed out with saturated Glauber's salt solution to remove the excess sulfuric acid and hydrochloric acid and finally neutralized with sodium hydroxide solution. The products obtained in this way are easily water-soluble, strongly wetting and foaming bodies, which have excellent resistance to hard water, acids, alkalis and concentrated salt solutions. In particular, the products, which have the constitution of real sulfonic acids, are also against cooking with acids and against dry heating. so resistant to higher temperatures that they do not split off the bound sulfuric acid.
Die Sulfonierungsprodukte der höheren aliphatischen ungesättigten und Oxyamine sind, daher überall da mit Vorteil zu verwenden, wo es auf Netzurig, Reinigung, Schaumerzeugung, Dispergieren und Lösen oder Transport wirksamer Bestandteile ankommt. Sie können für sich ,allein oder mit anderen Zusätzen, wie z. B. .aromatischen Sulfonsäuren und deren Salzen, sulfonierten Ölen, Seifen, organischen Lösungsmitteln (Kohlenwasserstoffen, Halogenkohlenwasserstoffen, höheren Alkoholen, Keton.en usw.), Anwendung finden. Als. Hauptverwendungsgebiete seien die Textil- und Lederindustrie, die Fettspaltung, ph rmazeutische Industrie, Herstellung von Schädlingsbekämpfungsmitteln sowie von Behandlungsflüssigkeiten für die Metallbearbeitung, wie z. B. von Bohrölen, erwähnt.The sulfonation products of the higher aliphatic unsaturated and oxyamines, therefore to be used with advantage wherever Netzurig, Cleaning, foam generation, dispersing and dissolving or transporting active ingredients arrives. They can be used on their own, or with other additives such as B. aromatic Sulphonic acids and their salts, sulphonated oils, soaps, organic solvents (Hydrocarbons, halogenated hydrocarbons, higher alcohols, ketones, etc.), Find application. As. The main areas of application are the textile and leather industry, lipolysis, pharmaceutical industry, manufacture of pesticides as well as treatment fluids for metalworking, such as. B. of drilling oils, mentioned.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB145809D DE669541C (en) | 1929-09-21 | 1929-09-22 | Process for the preparation of sulfonation products of unsaturated or hydroxylated compounds of the aliphatic series |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE698380X | 1929-09-21 | ||
| DEB145809D DE669541C (en) | 1929-09-21 | 1929-09-22 | Process for the preparation of sulfonation products of unsaturated or hydroxylated compounds of the aliphatic series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE669541C true DE669541C (en) | 1938-12-29 |
Family
ID=25946477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB145809D Expired DE669541C (en) | 1929-09-21 | 1929-09-22 | Process for the preparation of sulfonation products of unsaturated or hydroxylated compounds of the aliphatic series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE669541C (en) |
-
1929
- 1929-09-22 DE DEB145809D patent/DE669541C/en not_active Expired
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