CH193227A - Process for the preparation of a mixture of the sodium salts of the sulfonic acids of α-alkylindoles, which can be prepared from the o-toluidides of the fatty acids of the hydrogenated fish oil by ring closure. - Google Patents
Process for the preparation of a mixture of the sodium salts of the sulfonic acids of α-alkylindoles, which can be prepared from the o-toluidides of the fatty acids of the hydrogenated fish oil by ring closure.Info
- Publication number
- CH193227A CH193227A CH193227DA CH193227A CH 193227 A CH193227 A CH 193227A CH 193227D A CH193227D A CH 193227DA CH 193227 A CH193227 A CH 193227A
- Authority
- CH
- Switzerland
- Prior art keywords
- mixture
- alkylindoles
- toluidides
- fish oil
- ring closure
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 8
- 159000000000 sodium salts Chemical class 0.000 title claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 5
- 239000000194 fatty acid Substances 0.000 title claims description 5
- 229930195729 fatty acid Natural products 0.000 title claims description 5
- 150000004665 fatty acids Chemical class 0.000 title claims description 5
- 235000021323 fish oil Nutrition 0.000 title claims description 5
- 238000006798 ring closing metathesis reaction Methods 0.000 title claims description 5
- 150000003460 sulfonic acids Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 2
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 239000005457 ice water Substances 0.000 claims description 2
- 239000004571 lime Substances 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims 1
- 238000005187 foaming Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 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 1
- 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 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pyrrole Compounds (AREA)
Description
Verfahren zur Herstellung eines Gemisches der Natriumsalze der Sulfonsänren von a-Alkylindolen, die aus den o-Toluididen der Fettsäuren des hydrierten Fischtranes durch Ringschluss darstellbar sind.
Es wurde gefunden, dass man ein Ge misch der Natriumsalze der Sulfonsäuren von a-Alkylindolen, die aus den o-Toluididen der hydrierten Fischtranfettsäuren durch Ringschluss, beispielsweise mit Natriumalko- holat nach Madelung (Ber. 45, Seite 1l28), oder mit Natriumamid nach Verley (Bul. de la Soc. Chim. 1924, S. l039/40 und 1925., S.
189/91 herstellbar sind, erhält, wenn man diese a-Alkylindole unter milden Be dingungen so lange mit sulfonierenden Mit teln behandelt, bis Wasserlöslichkeit erreicht. ist und durch Neutralisieren mit Natronlauge die durch Ausgiessen in Eiswasser und Koch salzzusatz abgeschiedenen Sulfonsäuren in die Natriumsalze überführt. Diese werden nach dem Neutralisieren als weisses Pulver erhalten, das in Wasser sehr leicht löslich ist, dessen Lösungen stark schäumen und gute kapillaraktive Eigenschaften aufweisen.
Es soll insbesondere als Netz-, Dispergier-, Emulgier-. Durchdringungs- und Wasehmit- tel, insbesondere als Kalkseifenemulgator die nen; es kann aber auch Verwendung finden als Mittel zum Weiehmachen und Appre tieren.
Beispiel: In 90 Teile Oleum 10%ig werden unter Rühren zwischen 10 bis 20 C 60 Teile eines a-Alkylindols, hergestellt aus dem o-Toluidid von hydrierten Fischtranfettsäuren durch Ringschluss, allmählich eingetragen, darauf auf 5 C abgekühlt und langsam 120 Teile Oleum (26 %) zutropfen gelassen. Nach vier stündigem Rühren unter 5 C erweist sich eine in Wasser gegebene Probe beim Neu tralisieren vollständig wasserlöslich.
Sobald dies der Fall ist, wird die Reaktionsmasse auf Eis gegossen, das mit Kochsalz ausge schiedene Gemisch der freien Sulfonsäure ab getrennt und durch Zusatz von Natronlauge neutralisiert. Durch Eindampfen gewinnt man das Natronsalz als helles Pulver, das in Wasser sehr leicht löslich ist und dessen Lö sungen stark schäumen.
Zu einem Enderzeugnis mit ähnlichen Eigenschaften gelangt man, wenn man auf 60 Teile des gleichen a-Alkylindols unter obigen Bedingungen 120 Teile Monohydrat und 60 Teile Oleum 66 % ig einwirken lässt oder in 10 Teile eines Gemisches aus gleichen Teilen Monohydrat und Chlorsulfonsäure bei <B>10'</B> C einen Teil des gleichen Indols ein trägt, 14 Stunden rührt und wie oben an gegeben aufarbeitet.
Process for the preparation of a mixture of the sodium salts of the sulfonic acids of α-alkylindoles, which can be prepared from the o-toluidides of the fatty acids of the hydrogenated fish oil by ring closure.
It has been found that a mixture of the sodium salts of the sulfonic acids of α-alkylindoles obtained from the o-toluidides of the hydrogenated fish oil fatty acids by ring closure, for example with sodium alcoholate according to Madelung (Ber. 45, page 1128), or with sodium amide according to Verley (Bul. De la Soc. Chim. 1924, p. L039 / 40 and 1925., p.
189/91 can be produced, if these a-alkylindoles are treated with sulfonating agents under mild conditions until water solubility is reached. and by neutralizing with sodium hydroxide solution, the sulphonic acids separated by pouring into ice water and the addition of cooking salt are converted into the sodium salts. After neutralization, these are obtained as a white powder that is very easily soluble in water, the solutions of which foam strongly and have good capillary-active properties.
It should be used in particular as a wetting, dispersing, emulsifying. Penetrants and detergents, in particular as lime soap emulsifiers; but it can also be used as a means of whitewashing and apprecia- tion.
Example: 60 parts of an α-alkylindole, produced from the o-toluidide of hydrogenated fish oil fatty acids by ring closure, are gradually introduced into 90 parts of 10% oleum with stirring, then cooled to 5 ° C. and slowly 120 parts of oleum ( 26%) added dropwise. After four hours of stirring below 5 C, a sample placed in water proves to be completely water-soluble on neutralization.
As soon as this is the case, the reaction mass is poured onto ice, the mixture of free sulfonic acid separated out with common salt is separated and neutralized by adding sodium hydroxide solution. The sodium salt is obtained by evaporation as a light powder, which is very easily soluble in water and the solutions of which foam strongly.
An end product with similar properties is obtained if 120 parts of monohydrate and 60 parts of 66% oleum are allowed to act on 60 parts of the same α-alkylindole under the above conditions or in 10 parts of a mixture of equal parts of monohydrate and chlorosulfonic acid at <B> 10 'C enters part of the same indole, stirs for 14 hours and worked up as stated above.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191011T | 1936-05-14 | ||
| CH193227T | 1936-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH193227A true CH193227A (en) | 1937-09-30 |
Family
ID=25722074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH193227D CH193227A (en) | 1936-05-14 | 1936-05-14 | Process for the preparation of a mixture of the sodium salts of the sulfonic acids of α-alkylindoles, which can be prepared from the o-toluidides of the fatty acids of the hydrogenated fish oil by ring closure. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH193227A (en) |
-
1936
- 1936-05-14 CH CH193227D patent/CH193227A/en unknown
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